CN100505376C - 发光器件和显示装置 - Google Patents
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Abstract
一种发光器件,包括阴极,阳极和排列在电极之间的一层或多层有机薄膜,其特征在于至少一层是发光层,所述发光层包括金属配合物的发光分子,该金属配合物具有由下式(1)表示的基本结构并且在至少一个在主体材料中作为客体的环状基团A和B上具有取代基,其浓度为8wt%或更高,并且高于具有上述类似结构但不具有取代基的化合物的发光分子显示出最大发光效率时的浓度。该发光器件不易引起浓度衰减,甚至当在主体材料中以高浓度使用且因此显示高效率时。
Description
[技术领域]
本发明涉及在平面光源、平面显示器等中使用的有机薄膜发光器件。
本发明涉及使用有机化合物的发光器件,更特别地涉及在其发光层中含有发光材料的高效发光器件,所述发光材料包括不易引起浓度衰减(extinction)的金属配位化合物,即使当在高浓度下使用时。
[背景技术]
有机发光器件的一个古老实例是,例如使用真空沉积的蒽薄膜的器件(Thin Solid Films,94(1982)171)。然而,近年来,考虑到下述优点,例如与无机发光器件相比,容易提供大面积器件,和通过开发各种新材料可实现所需的发光颜色的可能性以及在低压下的可驱动性,在作为高速应答和高效率的发光器件的器件形成方面,紧接着已进行了深入的研究。
如Macromol.Symp.,125,1-48(1997)中所详述,有机EL器件的结构通常包括上部和下部两个电极以及在电极(其是在透明衬底上形成的)之间的多个有机薄膜层。图1(a)和1(b)示出了其基本结构。
如图1所示,有机EL器件的结构通常包括透明电极14、金属电极11和在透明衬底15上在所述电极之间的多个有机薄膜层。
在图1(a)的器件中,有机层包括发光层12和空穴迁移层13。对于透明电极14来说,使用具有大的功函的ITO等,为了从透明电极14向空穴迁移层13提供良好的空穴-注入特征。对于金属电极11来说,使用具有小的功函的金属,如铝、镁或这些金属的合金,为了提供良好的电子注入特征。这些电极的厚度为50-200纳米。
对于发光层12来说,使用具有电子迁移特征和发光特征的羟基喹啉铝络合物(其代表性实例是其后所示的Alq3)等。对于空穴迁移层来说,使用具有供电子特征的联苯二胺衍生物(其代表性实例是其后所示的α-NPD)等。
上述结构的器件具有整流特征,并且当在作为阴极的金属电极11与作为阳极的透明电极14之间施加电场时,电子从金属电极11注入到发光层12内,而空穴从透明电极15注入。注入的空穴和电子在发光层12内重组合,形成激子并引起发光。此刻,空穴迁移层13充当电子阻断层,以增加在发光层12与空穴迁移层13之间的边界处的重组合效率,从而增加发光效率。
此外,在图1(b)的结构中,电子迁移层16排列在金属电极11与发光层12之间。通过隔开发光与电子和空穴迁移,提供更有效的载流子阻断结构,可进行有效的发光。对于电子迁移层16来说,使用电子迁移材料,如噁二唑(oxidiazole)衍生物。
因此迄今为止在有机EL器件中使用的已知发光工艺包括利用激发单重态的工艺和利用激发三重态的工艺。从前一状态向基态的跃迁称为“荧光”,而从后一状态向基态的跃迁称为“磷光”。在这些受激态中的物质分别称为单重态激子和三重态激子。
在迄今为止所研究的大多数有机发光器件中,已利用从激发单重态向基态的跃迁所引起的荧光。另一方面,近年来,已研究利用借助三重态所引起的磷光的器件。
代表性的公开的文献可包括:
文章1:Improved energy transfer in electrophosphorescent device(D.F.O’Brien等,Applied Physics Letters,Vol.74,No.3,p.422(1999));和
文章2:Very high-efficiency green organic light-emitting devicesbased on electrophosphorescence(M.A.Baldo等,Applied PhysicsLetters,Vol.75,No.1,p.4(1999))。
在这些文章中,主要使用如图1(c)所示的含四层有机层的器件的结构体,该结构体从阳极一侧起包括空穴迁移层13、发光层12、激子扩散阻止层17和电子迁移层11。其中所使用的材料包括载流子迁移材料和磷光材料,下面描述其名称和结构以及它们的缩写。
Alq3:羟基喹啉铝络合物
α-NPD:N4,N4’-二萘-1-基-N4,N4’-二苯基联苯-4,4’-二胺
CBP:2,9-二甲基-4,7-二苯基-1,10-菲咯啉
PtOEP:八乙基卟啉铂络合物
Ir(ppy)3:苯基嘧啶铱络合物
上述文章1和2均报道了这些结构体,该结构体显示出高的效率,且包括含α-NPD的空穴迁移层13、含Alq3的电子迁移层16、含BCP的激子扩散阻止层17和含CBP的发光层12(其作为主体)以及分散在混合物中的作为磷光材料的约6%八乙基卟啉铂络合物(PtOEP)或苯基嘧啶铱络合物(Ir(ppy)3)。
这一磷光材料在目前是尤其引人注意的,因为由于下述理由,原则上预计它会提供高的发光效率。更具体地说,通过载流子重组合形成的激子包括概率比为1:3的单重态激子和三重态激子。常规的有机EL器件利用荧光,其发光效率限制为最多25%。另一方面,若利用三重态激子产生的磷光,则预计效率至少为3倍,甚至100%的效率,即原则上可预计4倍,若考虑到由于从高能的单重态向三重态的系间窜越引起的跃迁。
然而,如同荧光型器件,利用磷光的这种有机发光器件在发光效率的劣化和器件的稳定性方面通常要求进一步改进。
劣化的原因尚不完全清楚,但基于磷光机理,本发明者认为如下。
在发光层包括具有载流子迁移功能的主体材料和磷光客体材料的情况下,借助三重态激子的磷光过程可包括如下的单位过程:
1.电子和空穴在发光层内的迁移,
2.主体激子的形成,
3.主体分子之间的激发能传递,
4.从主体向客体的激发能传递,
5.客体三重态激子的形成,和
6.客体三重态激子向基态的跃迁和磷光。
在与各种能量失活过程竞争中引起在各单元过程中所需的能量传递和发光。
特别地,在磷光材料中,这可归因于三重态激子的寿命,它比单重态激子的寿命长三或更高的倍数(digits)。更具体地说,由于它在高能激发态下保持较长的时间段,所以容易与周围的材料反应,并在激子当中引起聚合物的形成,于是招致失活过程的较高概率,这导致材料变化或寿命劣化,正如我们所认为的。
毋庸置疑,通过增加发光中心材料的发光量子产率,可增加有机发光器件的发光效率,但为了增加器件的发光强度,增加发光层内发光材料的浓度也是重要的因素。
在发光层内低浓度的发光材料(最多数wt%)的情况下,发光强度随发光层内发光材料的浓度成正比例增加。然而,高于数%或7%时,观察到偏离正比例关系,发光强度反而降低,导致更差的效率。在日本专利申请JP-A 05-078655、JP-A 05-320633等中报道了这一现象,且被称为浓度衰减或浓度失活。
实际上,在CBP中使用Ir(pPy)3作为主体材料的情况下,在约6-7%的浓度下达到最佳的发光效率,而高于该浓度,发光效率反而降低,在12%的浓度下降低到约一半,在100%的浓度下降低到1/10或更低(Applied Physics Letters,4,Vol.75,1999)。
在具有三重态激子寿命比单重态激子寿命长3或更高倍数的磷光物质情况下,该现象是通过在三重激发态中大量存在等待发光的分子引起的。在这一状态下,容易发生由于三重态激子的相互作用引起的能耗的热失活。这称为三重态-三重态消失,与在高电流密度下发光效率的降低有关。此外,也认为由于在高能状态下长的保留时间引起激子具有增加的与周围材料反应和形成激子聚合物(这引起失活)的概率,或甚至导致材料变化或寿命劣化。
[发明公开]
本发明的目的是通过抑制上述浓度衰减现象和提供在较高浓度下使用发光材料的环境,从而提供更高发光强度的有机发光器件。
更具体地说,本发明的目的是通过在例如发光材料这样的金属配位化合物内引入取代基,从而提供不易引起浓度衰减的发光材料,即使相对于发光层内的主体材料,以高的浓度使用发光材料时。
本发明更具体的目的是提供能使发光强度大的有机发光器件,即下述的有机发光器件,其包括各自排列在衬底上的一对电极和排列在电极之间且包括有机化合物的至少一层发光层;其中发光层包括不发光的第一有机化合物和下式(1)表示的发磷光的第二有机化合物,且第二有机化合物以至少8wt%的浓度存在于发光层内:
MLmL’n (1)
其中M是Ir,Pt,Rh或Pd的金属原子;L和L’彼此为不同的双齿配体;m是1,2或3,n是0,1或2,前提是m+n为2或3;用以下所示的式(2)表示部分结构MLm,和用以下所示的式(3),(4)或(5)表示部分结构ML’n:
其中N和C分别是氮和碳原子;A和A’分别是能具有取代基且通过碳原子键合到金属原子M上的环状基团;B,B’和B”分别是以下所示的式(6)-(14)表示的环状基团,其能具有取代基且通过氮原子连接到金属原子M上:
根据另一方面,本发明的有机发光器件是含一层或多层有机薄膜的发光器件,所述有机薄膜排列在阴极和阳极之间,且包括至少一层发光层,其特征在于它含有式(1)的发光分子,该发光分子具有取代基,且在比类似结构但不具有取代基的发光分子显示出最大发光效率时的浓度高的浓度下,显示出最大的发光特征。
更具体地说,在含一层或多层有机薄膜(所述有机薄膜在阴极和阳极之间,且包括至少一层发光层)的发光器件中,优选以比类似结构的发光分子显示出比最大发光效率的浓度高的浓度下,包括含至少一个环状取代基的式(1)的发光分子。
[附图的简要说明]
图1例举了本发明的发光器件的实施方案。
图2例举了根据实施例28的简单矩阵型有机EL器件。
图3例举了实施例28中使用的驱动信号。
图4图解了包括EL器件和驱动方法的壁板式结构体。
图5例举了像素(pixel)电路的实例。
图6是显示TFT衬底的横截面结构实例的示意图。
[实施发明的最佳模式]
本发明的基本器件结构类似于图1(a),(b)和(c)中所示的那些。
更具体地说,如图1所示,有机发光器件通常包括在透明电极15上形成的50-200纳米厚的透明电极14、多层有机薄膜层和10-500纳米厚的金属电极11,以便把有机层夹在当中。
图1(a)示出了其中有机发光器件包括发光层12和空穴迁移层13的实施方案。透明电极14可包括具有大的功函的ITO等,以便促进空穴从透明电极14向空穴迁移层13的注入。金属电极11包括具有小的功函的金属材料,如铝、镁或这些元素的合金,以便促进电子注入到有机发光器件内。
发光层12包括本发明的化合物。空穴迁移层13可包括例如三苯基二胺衍生物,如以上所示的α-NPD所表示的,并且如所需地也包括具有供电子性能的材料。
以上组织起来的器件显示出电流整流特征,并且当在作为阴极的金属电极11与作为阳极的透明电极14之间施加电场时,电子从金属电极11注入到发光层12内,而空穴从透明电极15注入。注入的空穴和电子在发光层12内重组合,形成激子,从而引起发光。在该例子中,空穴迁移层13充当电子阻断层,增加在发光层12与空穴迁移层13之间的界面处的重组合效率,从而提供增加的发光效率。
此外,在图1(b)的结构中,电子迁移层16排列在图1(a)的金属电极11与发光层12之间。结果发光功能与电子迁移和空穴迁移功能相分离,提供显示更有效的载流子阻断的结构体,于是增加发光效率。电子迁移层16可包括例如噁二唑衍生物。
图1(c)示出了四层结构体的另一所需的形式,其从作为阳极的透明电极14一侧起按顺序包括空穴迁移层13、发光层12、激子扩散阻止层17和电子迁移层16。
以最多200纳米的厚度形成各有机薄膜层12,13,16和17,特别地以5-200纳米的厚度形成发光层12。
本发明者已了解到,包括取代的环状基团且用上述式(1)表示的金属配位化合物的使用,由于抑制了分子内的相互作用,使得可能高效发光和提供不易浓度衰减的倾向,即使在比常规含量高的浓度下。
也已发现,抑制浓度衰减是基于金属配位化合物所拥有的取代基的作用,和浓度衰减不易发生,这不是与配体的配位数无关,而是因为在至少一个配体上存在取代基。
特别地,结果在常规的磷光型有机EL器件中,在发光层中可以以8%或更高的浓度使用发光材料,从而提供显示出高发光亮度的有机EL器件。
本发明所使用的金属配位化合物发出磷光,并且认为在三重态中,其最低激发态是MLCT*(金属-向-配体的电荷转移)激发态或π-π*激发态,而在这一状态向基态跃迁的时刻引起磷光。
据说,MLCT*态下的磷光寿命一般短于π-π*态下的磷光寿命,但在本发明中使用的抑制浓度衰减的分子结构对作为最低激发态的MLCT*和π-π*二者均有效,和在任一种情况下,在发光层中可高浓度地掺入分子。
本发明的发光材料显示出0.1-0.9的高磷光产率,和0.1-30微秒的短磷光寿命。此处所指的磷光产率是相对的量子产率,即目标样品的量子产率Φ(样品)与标准样品的量子产率Φ(标准)之比,其根据下式测定:
Φ(样品)/Φ(标准)=[Sem(样品)/Iabs(样品)]/[Sem(标准)/Iabs(标准)]其中Iabs(标准)表示在标准样品的激发波长处的吸收系数;Sem(标准)表示当在相同波长处激发时,发光光谱的面积(areal)强度;Iabs(样品)表示在目标样品的激发波长处的吸收系数;和Sem(样品)表示当在相同波长处激发时,发光光谱的面积强度。
此处所述的磷光产率值是相对于作为标准样品的Ir(ppy)3的磷光产率Φ=1的相对值。
此外,此处所指的发光(磷光)寿命是基于根据下述方法所测量的值。
<<寿命的测量方法>>
将样品化合物溶解在氯仿中,并旋涂在约0.1微米厚的石英衬底上,且通过使用发光寿命计量仪(Hamamatsu Photonics K.K.制造),在室温下,在337nm的激发波长处,将其暴露于脉动氮气激光下。在完成激发脉冲之后,测量发光强度的衰变特征。
当用I0表示起始的发光强度时,在参考发光寿命τ(秒)的基础上,根据下式表达t(秒)之后的发光强度:
I=I0·exp(-t/τ)
因此,发光寿命τ是发光强度I衰减到起始强度I的1/e处时的时间段(I/I0=e-1,e是天然对数的底数)。
短的磷光寿命是提供高发光效率的EL器件的条件。更具体地说,长的磷光寿命是指存在大量等待发光的三重激发态分子,从而导致尤其在高电流密度下发光效率降低的问题。本发明的材料是合适的EL器件用发光材料,因为其具有高磷光产率和短的磷光寿命。此外,认为由于短的磷光寿命,所以在三重态下的持续时间缩短,以便抑制浓度衰减。本发明发光材料的高度稳定性也在真实器件的实际电流传导试验中得到证实。
在磷光材料的情况下,其发光特征严重地受到其分子环境的影响。在荧光器件的情况下,基于光致发光检测发光材料的基本性能。然而,在磷光的情况下,光致发光性能并不直接导致EL器件的发光性能,因为它常受到主体分子、温度和固体/液体状态的影响。结果,不可能由光致发光结果估计EL器件的性能(其部分性能除外)。
在本发明配体具有含一个或更多个氟原子的环状基团的情况下,因为能隙的变化,可能使发光波长向更短的一侧或更长的一侧位移。若为了方便起见,认为可独立地考虑金属电子轨道的HOMO/LUMO和配体电子轨道的HOMO/LUMO,则应理解为配体电子轨道的HOMO/LUMO能级被具有大的电负性的氟原子改变,使金属的HOMO能级与配体的LUMO能级之间的能隙改变,从而使发光从作为最低激发态的MCLT态位移到更短波长的一侧或更长波长的一侧。因此,尽管尚未发现在宽的波长范围内(从蓝到红)显示出稳定地高量子产率的发光材料,但因此可意识到本发明的发光材料能在所需的发射波长处在宽的波长范围内(从蓝到红)提供显示出高效率的发光材料。
当形成器件时,由于氟原子大的电负性,分子间相互作用受到抑制,以致于物理地导致抑制的结晶度,这有利于均匀的薄膜形成,和物理地抑制二聚反应,以禁止能量失活,这导致改进的发光效率,从而导致改进的电性能和改进的器件稳定性。
此外,在使用含有多个氟原子或多氟烷基作为取代基的配体情况下,认为由于通过它们的电效应引起的电排斥或由于空间位阻,使发光分子之间的直接相互作用受到抑制,从而防止能量失活和浓度衰减。
此外,考虑到器件的制备,具有取代基,特别是氟化取代基的发光材料使得更可能容易地真空沉积,这是因为通过真空沉积在薄膜形成过程中降低了升华温度,因此在这一方面也提供很大的优势。
结果,如其后所示的实施例中所述,通过使用本发明具有取代基的发光材料,可预计在抑制的浓度衰减下稳定数小时的发光。此外,可在-20℃至60℃(这是有机发光器件的实际操作温度)的温度范围内达到高的磷光产率。另外,相对于发光层内的主体材料,以8wt%或更高的浓度,或在比不具有取代基的化合物高的浓度下使用化合物的情况下,可能提供显示出优良发光性能,同时抑制浓度衰减的EL器件。在发光层内,本发明的发光材料的浓度可以至少8wt%,优选10wt%或更高,但潜在地甚至可能以100%的浓度使用发光材料,而没有引起显著的浓度衰减。
此处的术语“发光性能”是指基于最大发光效率的特征,它可用任何最大亮度、最大亮度/电流、最大光通量/能耗或最大外部量子产率的形式来表达。
本发明的高效发光器件应用于要求能量节约或高亮度的产品。更具体地说,该发光器件应用于显示装置、照明装置、打印机光源或发光层显示装置用的后照光。至于显示装置,它允许质轻且在低能耗下提供高度可识别显示的平板显示器。至于打印机光源,可使用本发明的发光器件替代激光束打印机的激光光源。以阵列形式排列独立地可寻址的器件,在光敏鼓上进行所需的暴露,从而形成图象。通过使用本发明的器件可显著降低装置体积。对于发光装置或后照光来说,可预期本发明的节能效应。
至于在显示器上的应用,可使用根据有源矩阵图案(active matrix-scheme)的薄膜晶体管(简称为TFT)驱动电路的驱动系统。通过在发光层中使用本发明的发光材料驱动显示板,使得可能在良好的图象质量下长时间地稳定显示。
在下文中,在以下出现的表1中示出了本发明所使用的式(1)表示的金属配位化合物的一些具体的结构分子式,然而它们仅是例举而不是穷举。表1所使用的Ph至P9表示以下所示的部分结构,在表1中,其中的取代基R1,R2…当包含在分子式(1)中的环状基团A内时表示为A-R1,A-R2,…,而当包含在环状基团B内时表示为B-R1,B-R2,…。
表1-1
表1-2
No | M | A | B | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 | ||
61 | Ir | 3 | 0 | Ph | P1 | H | H | H | H | H | H | H | C4H9 |
62 | Ir | 3 | 0 | Ph | P1 | H | H | H | H | C8H17 | H | H | H |
63 | Ir | 3 | 0 | Ph | P1 | H | H | H | H | H | C8H17 | H | H |
64 | Ir | 3 | 0 | Ph | P1 | H | H | H | H | H | H | C8H17 | H |
65 | Ir | 3 | 0 | Ph | P1 | H | H | H | H | H | H | H | C8H17 |
66 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | CH3 | H | H | H |
67 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | H | CH3 | H | H |
68 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | H | H | CH3 | H |
69 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | H | H | H | CH3 |
70 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | CH3 | H | H | H |
71 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | H | CH3 | H | H |
72 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | H | H | CH3 | H |
73 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | H | H | H | CH3 |
74 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | CH3 | H | H | H |
75 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | H | CH3 | H | H |
76 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | H | H | CH3 | H |
77 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | H | H | H | CH3 |
78 | Ir | 3 | 0 | Ph | P1 | H | H | H | CH3 | H | H | CH3 | H |
79 | Ir | 3 | 0 | Ph | P1 | C2H5 | H | H | H | H | CH3 | H | H |
80 | Ir | 3 | 0 | Ph | P1 | C2H5 | H | H | H | H | H | CH3 | H |
81 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | CH3 | H | H | H |
82 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | H | CH3 | H | H |
83 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | H | H | CH3 | H |
84 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | H | H | H | CH3 |
85 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | CH3 | H | H | H |
86 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | H | CH3 | H | H |
87 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | H | H | CH3 | H |
88 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | H | H | H | CH3 |
89 | Ir | 3 | 0 | Ph | P1 | H | H | H | C2H5 | H | CH3 | H | H |
90 | Ir | 3 | 0 | Ph | P1 | H | H | H | C2H5 | H | H | CH3 | H |
91 | Ir | 3 | 0 | Ph | P1 | C4H9 | H | H | H | H | CH3 | H | H |
92 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | CH3 | H | H | H |
93 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | H | CH3 | H | H |
94 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | H | H | CH3 | H |
95 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | H | H | H | CH3 |
96 | Ir | 3 | 0 | Ph | P1 | H | H | C4H9 | H | H | CH3 | H | H |
97 | Ir | 3 | 0 | Ph | P1 | H | H | C4H9 | H | H | H | CH3 | H |
98 | Ir | 3 | 0 | Ph | P1 | H | H | H | C4H9 | H | CH3 | H | H |
99 | Ir | 3 | 0 | Ph | P1 | H | H | H | C4H9 | H | CH3 | H | H |
100 | Ir | 3 | 0 | Ph | P1 | C6H13 | H | H | H | H | CH3 | H | H |
101 | Ir | 3 | 0 | Ph | P1 | H | C6H13 | H | H | CH3 | H | H | H |
102 | Ir | 3 | 0 | Ph | P1 | H | C6H13 | H | H | H | CH3 | H | H |
103 | Ir | 3 | 0 | Ph | P1 | H | C6H13 | H | H | H | H | CH3 | H |
104 | Ir | 3 | 0 | Ph | P1 | H | C6H13 | H | H | H | H | H | CH3 |
105 | Ir | 3 | 0 | Ph | P1 | H | H | C6H13 | H | H | CH3 | H | H |
106 | Ir | 3 | 0 | Ph | P1 | H | H | C6H13 | H | H | H | CH3 | H |
107 | Ir | 3 | 0 | Ph | P1 | H | H | H | C6H13 | H | CH3 | H | H |
108 | Ir | 3 | 0 | Ph | P1 | H | H | H | C6H13 | H | CH3 | H | H |
109 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | CF3 | H | H | H |
110 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | CF3 | H | H | H |
111 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | CF3 | H | H | H |
112 | Ir | 3 | 0 | Ph | P1 | H | H | H | CH3 | CF3 | H | H | H |
113 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | H | CF3 | H | H |
114 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | H | CF3 | H | H |
115 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | H | CF3 | H | H |
116 | Ir | 3 | 0 | Ph | P1 | H | H | H | CH3 | H | CF3 | H | H |
117 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | H | H | CF3 | H |
118 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | H | H | CF3 | H |
119 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | H | H | CF3 | H |
120 | Ir | 3 | 0 | Ph | P1 | H | H | H | CH3 | H | H | CF3 | H |
表1-3
No | M | m | n | A | B | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
121 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | H | H | H | CF3 |
122 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | H | H | H | CF3 |
123 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | H | H | H | CF3 |
124 | Ir | 3 | 0 | Ph | P1 | H | H | H | CH3 | H | H | H | CF3 |
125 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | F | H | H | H |
126 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | F | H | H | H |
127 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | F | H | H | H |
128 | Ir | 3 | 0 | Ph | P1 | H | H | H | CH3 | F | H | H | H |
129 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | H | F | H | H |
130 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | H | F | H | H |
131 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | H | F | H | H |
132 | Ir | 3 | 0 | Ph | P1 | H | H | H | CH3 | H | F | H | H |
133 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | H | H | F | H |
134 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | H | H | F | H |
135 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | H | H | F | H |
136 | Ir | 3 | 0 | Ph | P1 | H | H | H | CH3 | H | H | F | H |
137 | Ir | 3 | 0 | Ph | P1 | CH3 | H | H | H | H | H | H | F |
138 | Ir | 3 | 0 | Ph | P1 | H | CH3 | H | H | H | H | H | F |
139 | Ir | 3 | 0 | Ph | P1 | H | H | CH3 | H | H | H | H | F |
140 | Ir | 3 | 0 | Ph | P1 | H | H | H | CH3 | H | H | H | F |
141 | Ir | 3 | 0 | Ph | P1 | C2H5 | H | H | H | CF3 | H | H | H |
142 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | CF3 | H | H | H |
143 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | CF3 | H | H | H |
144 | Ir | 3 | 0 | Ph | P1 | H | H | H | C2H5 | CF3 | H | H | H |
145 | Ir | 3 | 0 | Ph | P1 | C2H5 | H | H | H | H | CF3 | H | H |
146 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | H | CF3 | H | H |
147 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | H | CF3 | H | H |
148 | Ir | 3 | 0 | Ph | P1 | H | H | H | C2H5 | H | CF3 | H | H |
149 | Ir | 3 | 0 | Ph | P1 | C2H5 | H | H | H | H | H | CF3 | H |
150 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | H | H | CF3 | H |
151 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | H | H | CF3 | H |
152 | Ir | 3 | 0 | Ph | P1 | H | H | H | C2H5 | H | H | CF3 | H |
153 | Ir | 3 | 0 | Ph | P1 | C2H5 | H | H | H | H | H | H | CF3 |
154 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | H | H | H | CF3 |
155 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | H | H | H | CF3 |
156 | Ir | 3 | 0 | Ph | P1 | H | H | H | C2H5 | H | H | H | CF3 |
157 | Ir | 3 | 0 | Ph | P1 | C2H5 | H | H | H | F | H | H | H |
158 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | F | H | H | H |
159 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | F | H | H | H |
160 | Ir | 3 | 0 | Ph | P1 | H | H | H | C2H5 | F | H | H | H |
161 | Ir | 3 | 0 | Ph | P1 | C2H5 | H | H | H | H | F | H | H |
162 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | H | F | H | H |
163 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | H | F | H | H |
164 | Ir | 3 | 0 | Ph | P1 | H | H | H | C2H5 | H | F | H | H |
165 | Ir | 3 | 0 | Ph | P1 | C2H5 | H | H | H | H | H | F | H |
166 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | H | H | F | H |
167 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | H | H | F | H |
166 | Ir | 3 | 0 | Ph | P1 | H | H | H | C2H5 | H | H | F | H |
169 | Ir | 3 | 0 | Ph | P1 | C2H5 | H | H | H | H | H | H | F |
170 | Ir | 3 | 0 | Ph | P1 | H | C2H5 | H | H | H | H | H | F |
171 | Ir | 3 | 0 | Ph | P1 | H | H | C2H5 | H | H | H | H | F |
172 | Ir | 3 | 0 | Ph | P1 | H | H | H | C2H5 | H | H | H | F |
173 | Ir | 3 | 0 | Ph | P1 | C4H9 | H | H | H | F | H | H | H |
174 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | F | H | H | H |
175 | Ir | 3 | 0 | Ph | P1 | H | H | C4H9 | H | F | H | H | H |
176 | Ir | 3 | 0 | Ph | P1 | H | H | H | C4H9 | F | H | H | H |
177 | Ir | 3 | 0 | Ph | P1 | C4H9 | H | H | H | H | F | H | H |
178 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | H | F | H | H |
179 | Ir | 3 | 0 | Ph | P1 | H | H | C4H9 | H | H | F | H | H |
180 | Ir | 3 | 0 | Ph | P1 | H | H | H | C4H9 | H | F | H | H |
表1-4
No | M | m | n | A | B | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
181 | Ir | 3 | 0 | Ph | P1 | C4H9 | H | H | H | H | H | F | H |
182 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | H | H | F | H |
183 | Ir | 3 | 0 | Ph | P1 | H | H | C4H9 | H | H | H | F | H |
184 | Ir | 3 | 0 | Ph | P1 | H | H | H | C4H9 | H | H | F | H |
185 | Ir | 3 | 0 | Ph | P1 | C4H9 | H | H | H | H | H | H | F |
186 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | H | H | H | F |
187 | Ir | 3 | 0 | Ph | P1 | H | H | C4H9 | H | H | H | H | F |
188 | Ir | 3 | 0 | Ph | P1 | H | H | H | C4H9 | H | H | H | F |
189 | Ir | 3 | 0 | Ph | P1 | C4H9 | H | H | H | CF3 | H | H | H |
190 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | CF3 | H | H | H |
191 | Ir | 3 | 0 | Ph | P1 | H | H | C4H9 | H | CF3 | H | H | H |
192 | Ir | 3 | 0 | Ph | P1 | H | H | H | C4H9 | CF3 | H | H | H |
193 | Ir | 3 | 0 | Ph | P1 | C4H9 | H | H | H | H | CF3 | H | H |
194 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | H | CF3 | H | H |
195 | Ir | 3 | 0 | Ph | P1 | H | H | C4H9 | H | H | CF3 | H | H |
196 | Ir | 3 | 0 | Ph | P1 | H | H | H | C4H9 | H | CF3 | H | H |
197 | Ir | 3 | 0 | Ph | P1 | C4H9 | H | H | H | H | H | CF3 | H |
198 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | H | H | CF3 | H |
199 | Ir | 3 | 0 | Ph | P1 | H | H | C4H9 | H | H | H | CF3 | H |
200 | Ir | 3 | 0 | Ph | P1 | H | H | H | C4H9 | H | H | CF3 | H |
201 | Ir | 3 | 0 | Ph | P1 | C4H9 | H | H | H | H | H | H | CF3 |
202 | Ir | 3 | 0 | Ph | P1 | H | C4H9 | H | H | H | H | H | CF3 |
203 | Ir | 3 | 0 | Ph | P1 | H | H | C4H9 | H | H | H | H | CF3 |
204 | Ir | 3 | 0 | Ph | P1 | H | H | H | C4H9 | H | H | H | CF3 |
205 | Ir | 3 | 0 | Ph | P1 | C8H17 | H | H | H | F | H | H | H |
206 | Ir | 3 | 0 | Ph | P1 | H | C8H17 | H | H | F | H | H | H |
207 | Ir | 3 | 0 | Ph | P1 | H | H | C8H17 | H | F | H | H | H |
208 | Ir | 3 | 0 | Ph | P1 | H | H | H | C8H17 | F | H | H | H |
209 | Ir | 3 | 0 | Ph | P1 | C8H17 | H | H | H | H | F | H | H |
210 | Ir | 3 | 0 | Ph | P1 | H | C8H17 | H | H | H | F | H | H |
211 | Ir | 3 | 0 | Ph | P1 | H | H | C8H17 | H | H | F | H | H |
212 | Ir | 3 | 0 | Ph | P1 | H | H | H | C8H17 | H | F | H | H |
213 | Ir | 3 | 0 | Ph | P1 | C8H17 | H | H | H | H | H | F | H |
214 | Ir | 3 | 0 | Ph | P1 | H | C8H17 | H | H | H | H | F | H |
215 | Ir | 3 | 0 | Ph | P1 | H | H | C8H17 | H | H | H | F | H |
216 | Ir | 3 | 0 | Ph | P1 | H | H | H | C8H17 | H | H | F | H |
217 | Ir | 3 | 0 | Ph | P1 | C8H17 | H | H | H | H | H | H | F |
218 | Ir | 3 | 0 | Ph | P1 | H | C8H17 | H | H | H | H | H | F |
219 | Ir | 3 | 0 | Ph | P1 | H | H | C8H17 | H | H | H | H | F |
220 | Ir | 3 | 0 | Ph | P1 | H | H | H | C8H17 | H | H | H | F |
221 | Ir | 3 | 0 | Ph | P1 | C8H17 | H | H | H | CF3 | H | H | H |
222 | Ir | 3 | 0 | Ph | P1 | H | C8H17 | H | H | CF3 | H | H | H |
223 | Ir | 3 | 0 | Ph | P1 | H | H | C8H17 | H | CF3 | H | H | H |
224 | Ir | 3 | 0 | Ph | P1 | H | H | H | C8H17 | CF3 | H | H | H |
225 | Ir | 3 | 0 | Ph | P1 | C8H17 | H | H | H | H | CF3 | H | H |
226 | Ir | 3 | 0 | Ph | P1 | H | C8H17 | H | H | H | CF3 | H | H |
227 | Ir | 3 | 0 | Ph | P1 | H | H | C8H17 | H | H | CF3 | H | H |
228 | Ir | 3 | 0 | Ph | P1 | H | H | H | C8H17 | H | CF3 | H | H |
229 | Ir | 3 | 0 | Ph | P1 | C8H17 | H | H | H | H | H | CF3 | H |
230 | Ir | 3 | 0 | Ph | P1 | H | C8H17 | H | H | H | H | CF3 | H |
231 | Ir | 3 | 0 | Ph | P1 | H | H | C8H17 | H | H | H | CF3 | H |
232 | Ir | 3 | 0 | Ph | P1 | H | H | H | C8H17 | H | H | CF3 | H |
233 | Ir | 3 | 0 | Ph | P1 | C8H17 | H | H | H | H | H | H | CF3 |
234 | Ir | 3 | 0 | Ph | P1 | H | C8H17 | H | H | H | H | H | CF3 |
235 | Ir | 3 | 0 | Ph | P1 | H | H | C8H17 | H | H | H | H | CF3 |
236 | Ir | 3 | 0 | Ph | P1 | H | H | H | C8H17 | H | H | H | CF3 |
237 | Ir | 3 | 0 | Ph | P1 | F | H | H | H | H | H | H | H |
238 | Ir | 3 | 0 | Ph | P1 | H | F | H | H | H | H | H | H |
239 | Ir | 3 | 0 | Ph | P1 | H | H | F | H | H | H | H | H |
240 | Ir | 3 | 0 | Ph | P1 | H | H | H | F | H | H | H | H |
表1-5
No | M | m | n | A | B | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
241 | Ir | 3 | 0 | Ph | P1 | F | F | H | H | H | H | H | H |
242 | Ir | 3 | 0 | Ph | P1 | F | H | F | H | H | H | H | H |
243 | Ir | 3 | 0 | Ph | P1 | H | F | H | F | H | H | H | H |
244 | Ir | 3 | 0 | Ph | P1 | H | F | F | H | H | H | H | H |
245 | Ir | 3 | 0 | Ph | P1 | H | F | H | H | H | H | H | H |
246 | Ir | 3 | 0 | Ph | P1 | H | H | H | F | H | H | H | H |
247 | Ir | 3 | 0 | Ph | P1 | H | H | F | F | H | H | H | H |
248 | Ir | 3 | 0 | Ph | P1 | F | H | F | F | H | H | H | H |
249 | Ir | 3 | 0 | Ph | P1 | F | F | F | H | H | H | H | H |
250 | Ir | 3 | 0 | Ph | P1 | H | F | F | F | H | H | H | H |
251 | Ir | 3 | 0 | Ph | P1 | F | F | F | H | H | H | H | H |
252 | Ir | 3 | 0 | Ph | P1 | F | F | F | F | H | H | H | H |
253 | Ir | 3 | 0 | Ph | P1 | F | H | H | H | CH3 | H | H | H |
254 | Ir | 3 | 0 | Ph | P1 | F | H | H | H | H | CH3 | H | H |
255 | Ir | 3 | 0 | Ph | P1 | F | H | H | H | H | H | CH3 | H |
256 | Ir | 3 | 0 | Ph | P1 | F | H | H | H | H | H | H | CH3 |
257 | Ir | 3 | 0 | Ph | P1 | H | F | H | H | CH3 | H | H | H |
258 | Ir | 3 | 0 | Ph | P1 | H | F | H | H | H | CH3 | H | H |
259 | Ir | 3 | 0 | Ph | P1 | H | F | H | H | H | H | CH3 | H |
260 | Ir | 3 | 0 | Ph | P1 | H | F | H | H | H | H | H | CH3 |
261 | Ir | 3 | 0 | Ph | P1 | H | H | F | H | CH3 | H | H | H |
262 | Ir | 3 | 0 | Ph | P1 | H | H | F | H | H | CH3 | H | H |
263 | Ir | 3 | 0 | Ph | P1 | H | H | F | H | H | H | CH3 | H |
264 | Ir | 3 | 0 | Ph | P1 | H | H | F | H | H | H | H | CH3 |
265 | Ir | 3 | 0 | Ph | P1 | H | H | H | F | CH3 | H | H | H |
266 | Ir | 3 | 0 | Ph | P1 | H | H | H | F | H | CH3 | H | H |
267 | Ir | 3 | 0 | Ph | P1 | H | H | H | F | H | H | CH3 | H |
268 | Ir | 3 | 0 | Ph | P1 | H | H | H | F | H | H | H | CH3 |
269 | Ir | 3 | 0 | Ph | P1 | F | F | H | H | CH3 | H | H | H |
270 | Ir | 3 | 0 | Ph | P1 | F | F | H | H | H | CH3 | H | H |
271 | Ir | 3 | 0 | Ph | P1 | F | F | H | H | H | H | CH3 | H |
272 | Ir | 3 | 0 | Ph | P1 | F | F | H | H | H | H | H | CH3 |
273 | Ir | 3 | 0 | Ph | P1 | F | H | F | H | CH3 | H | H | H |
274 | Ir | 3 | 0 | Ph | P1 | F | H | F | H | H | CH3 | H | H |
275 | Ir | 3 | 0 | Ph | P1 | F | H | F | H | H | H | CH3 | H |
276 | Ir | 3 | 0 | Ph | P1 | F | H | F | H | H | H | H | CH3 |
277 | Ir | 3 | 0 | Ph | P1 | F | H | H | F | CH3 | H | H | H |
278 | Ir | 3 | 0 | Ph | P1 | F | H | H | F | H | CH3 | H | H |
279 | Ir | 3 | 0 | Ph | P1 | F | H | H | F | H | H | CH3 | H |
280 | Ir | 3 | 0 | Ph | P1 | F | H | H | F | H | H | H | CH3 |
281 | Ir | 3 | 0 | Ph | P1 | H | F | F | H | CH3 | H | H | H |
282 | Ir | 3 | 0 | Ph | P1 | H | F | F | H | H | CH3 | H | H |
283 | Ir | 3 | 0 | Ph | P1 | H | F | F | H | H | H | CH3 | H |
284 | Ir | 3 | 0 | Ph | P1 | H | F | F | H | H | H | H | CH3 |
285 | Ir | 3 | 0 | Ph | P1 | H | F | H | F | CH3 | H | H | H |
286 | Ir | 3 | 0 | Ph | P1 | H | F | H | F | H | CH3 | H | H |
287 | Ir | 3 | 0 | Ph | P1 | H | F | H | F | H | H | CH3 | H |
288 | Ir | 3 | 0 | Ph | P1 | H | F | H | F | H | H | H | CH3 |
289 | Ir | 3 | 0 | Ph | P1 | H | H | F | F | CH3 | H | H | H |
290 | Ir | 3 | 0 | Ph | P1 | H | H | F | F | H | CH3 | H | H |
291 | Ir | 3 | 0 | Ph | P1 | H | H | F | F | H | H | CH3 | H |
292 | Ir | 3 | 0 | Ph | P1 | H | H | F | F | H | H | H | CH3 |
293 | Ir | 3 | 0 | Ph | P1 | F | F | F | H | CH3 | H | H | H |
294 | Ir | 3 | 0 | Ph | P1 | F | F | F | H | H | CH3 | H | H |
295 | Ir | 3 | 0 | Ph | P1 | F | F | F | H | H | H | CH3 | H |
296 | Ir | 3 | 0 | Ph | P1 | F | F | F | H | H | H | H | CH3 |
297 | Ir | 3 | 0 | Ph | P1 | F | F | H | F | CH3 | H | H | H |
298 | Ir | 3 | 0 | Ph | P1 | F | F | H | F | H | CH3 | H | H |
299 | Ir | 3 | 0 | Ph | P1 | F | F | H | F | H | H | CH3 | H |
300 | Ir | 3 | 0 | Ph | P1 | F | F | H | F | H | H | H | CH3 |
表1-6
No | M | m | n | A | B | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 | |
301 | Ir | 3 | 0 | Ph | P1 | F | H | F | F | CH3 | H | H | H | |
302 | Ir | 3 | 0 | Ph | P1 | F | H | F | F | H | CH3 | H | H | |
303 | Ir | 3 | 0 | Ph | P1 | F | H | F | F | H | H | CH3 | H | |
304 | Ir | 3 | 0 | Ph | P1 | F | H | F | F | H | H | H | CH3 | |
305 | Ir | 3 | 0 | Ph | P1 | F | F | F | F | CH3 | H | H | H | |
306 | Ir | 3 | 0 | Ph | P1 | F | F | F | F | H | CH3 | H | H | |
307 | Ir | 3 | 0 | Ph | P1 | F | F | F | F | H | H | CH3 | H | |
308 | Ir | 3 | 0 | Ph | P1 | F | F | F | F | H | H | H | CH3 | |
309 | Ir | 3 | 0 | Ph | P1 | CF3 | H | H | H | H | H | H | H | |
310 | Ir | 3 | 0 | Ph | P1 | H | CF3 | H | H | H | H | H | H | |
311 | Ir | 3 | 0 | Ph | P1 | H | H | CF3 | H | H | H | H | H | |
312 | Ir | 3 | 0 | Ph | P1 | H | CF3 | H | CF3 | H | H | H | H | |
3 | 3 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | H | H | H | H | H | H |
3 | 4 | Ir | 3 | 0 | Ph | P1 | CF3 | H | CF3 | H | H | H | H | H |
315 | Ir | 3 | 0 | Ph | P1 | CF3 | H | H | CF3 | H | H | H | H | |
3 | 6 | Ir | 3 | 0 | Ph | P1 | H | CF3 | CF3 | H | H | H | H | H |
317 | Ir | 3 | 0 | Ph | P1 | H | H | C3F7C2H4 | H | H | H | H | H | |
3 | 8 | Ir | 3 | 0 | Ph | P1 | H | H | C7F15 | H | H | H | H | H |
319 | Ir | 3 | 0 | Ph | P1 | H | H | CF3 | CF3 | H | H | H | H | |
320 | Ir | 3 | 0 | Ph | P1 | CF3 | H | CF3 | CF3 | H | H | H | H | |
321 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | H | H | H | H | H | |
322 | Ir | 3 | 0 | Ph | P1 | H | CF3 | CF3 | CF3 | H | H | H | H | |
323 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | H | H | H | H | H | |
324 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | CF3 | H | H | H | H | |
325 | Ir | 3 | 0 | Ph | P1 | CF3 | H | H | H | CH3 | H | H | H | |
326 | Ir | 3 | 0 | Ph | P1 | CF3 | H | H | H | H | CH3 | H | H | |
327 | Ir | 3 | 0 | Ph | P1 | CF3 | H | H | H | H | H | CH3 | H | |
328 | Ir | 3 | 0 | Ph | P1 | CF3 | H | H | H | H | H | H | CH3 | |
329 | Ir | 3 | 0 | Ph | P1 | H | CF3 | H | H | CH3 | H | H | H | |
330 | Ir | 3 | 0 | Ph | P1 | H | CF3 | H | H | H | CH3 | H | H | |
331 | Ir | 3 | 0 | Ph | P1 | H | CF3 | H | H | H | H | CH3 | H | |
332 | Ir | 3 | 0 | Ph | P1 | H | CF3 | H | H | H | H | H | CH3 | |
333 | Ir | 3 | 0 | Ph | P1 | H | H | CF3 | H | CH3 | H | H | H | |
334 | Ir | 3 | 0 | Ph | P1 | H | H | CF3 | H | H | CH3 | H | H | |
335 | Ir | 3 | 0 | Ph | P1 | H | H | CF3 | H | H | H | CH3 | H | |
336 | Ir | 3 | 0 | Ph | P1 | H | H | CF3 | H | H | H | H | CH3 | |
337 | Ir | 3 | 0 | Ph | P1 | H | H | H | CF3 | CH3 | H | H | H | |
338 | Ir | 3 | 0 | Ph | P1 | H | H | H | CF3 | H | CH3 | H | H | |
339 | Ir | 3 | 0 | Ph | P1 | H | H | H | CF3 | H | H | CH3 | H | |
340 | Ir | 3 | 0 | Ph | P1 | H | H | H | CF3 | H | H | H | CH3 | |
341 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | H | H | CH3 | H | H | H | |
342 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | H | H | H | CH3 | H | H | |
343 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | H | H | H | H | CH3 | H | |
344 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | H | H | H | H | H | CH3 | |
345 | Ir | 3 | 0 | Ph | P1 | CF3 | H | CF3 | H | CH3 | H | H | H | |
346 | Ir | 3 | 0 | Ph | P1 | CF3 | H | CF3 | H | H | CH3 | H | H | |
347 | Ir | 3 | 0 | Ph | P1 | CF3 | H | CF3 | H | H | H | CH3 | H | |
348 | Ir | 3 | 0 | Ph | P1 | CF3 | H | CF3 | H | H | H | H | CH3 | |
349 | Ir | 3 | 0 | Ph | P1 | CF3 | H | H | CF3 | CH3 | H | H | H | |
350 | Ir | 3 | 0 | Ph | P1 | CF3 | H | H | CF3 | H | CH3 | H | H | |
351 | Ir | 3 | 0 | Ph | P1 | CF3 | H | H | CF3 | H | H | CH3 | H | |
352 | Ir | 3 | 0 | Ph | P1 | CF3 | H | H | CF3 | H | H | H | CH3 | |
353 | Ir | 3 | 0 | Ph | P1 | H | CF3 | CF3 | H | CH3 | H | H | H | |
354 | Ir | 3 | 0 | Ph | P1 | H | CF3 | CF3 | H | H | CH3 | H | H | |
355 | Ir | 3 | 0 | Ph | P1 | H | CF3 | CF3 | H | H | H | CH3 | H | |
356 | Ir | 3 | 0 | Ph | P1 | H | CF3 | CF3 | H | H | H | H | CH3 | |
357 | Ir | 3 | 0 | Ph | P1 | H | CF3 | H | CF3 | CH3 | H | H | H | |
358 | Ir | 3 | 0 | Ph | P1 | H | CF3 | H | CF3 | H | CH3 | H | H | |
359 | Ir | 3 | 0 | Ph | P1 | H | CF3 | H | CF3 | H | H | CH3 | H | |
360 | Ir | 3 | 0 | Ph | P1 | H | CF3 | H | CF3 | H | H | H | CH3 |
表1-7
No | M | m | n | A | B | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
361 | Ir | 3 | 0 | Ph | P1 | H | H | CF3 | CF3 | CH3 | H | H | H |
362 | Ir | 3 | 0 | Ph | P1 | H | H | CF3 | CF3 | H | CH3 | H | H |
363 | Ir | 3 | 0 | Ph | P1 | H | H | CF3 | CF3 | H | H | CH3 | H |
364 | Ir | 3 | 0 | Ph | P1 | H | H | CF3 | CF3 | H | H | H | CH3 |
365 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | H | CH3 | H | H | H |
366 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | H | H | CH3 | H | H |
367 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | H | H | H | CH3 | H |
368 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | H | H | H | H | CH3 |
369 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | H | CF3 | CH3 | H | H | H |
370 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | H | CF3 | H | CH3 | H | H |
371 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | H | CF3 | H | H | CH3 | H |
372 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | H | CF3 | H | H | H | CH3 |
373 | Ir | 3 | 0 | Ph | P1 | CF3 | H | CF3 | CF3 | CH3 | H | H | H |
374 | Ir | 3 | 0 | Ph | P1 | CF3 | H | CF3 | CF3 | H | CH3 | H | H |
375 | Ir | 3 | 0 | Ph | P1 | CF3 | H | CF3 | CF3 | H | H | CH3 | H |
376 | Ir | 3 | 0 | Ph | P1 | CF3 | H | CF3 | CF3 | H | H | H | CH3 |
377 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | CF3 | CH3 | H | H | H |
378 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | CF3 | H | CH3 | H | H |
379 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | CF3 | H | H | CH3 | H |
380 | Ir | 3 | 0 | Ph | P1 | CF3 | CF3 | CF3 | CF3 | H | H | H | CH3 |
381 | Ir | 3 | 0 | Ph | P1 | F | CF3 | H | H | H | H | H | H |
382 | Ir | 3 | 0 | Ph | P1 | F | CF3 | H | CF3 | H | H | H | H |
383 | Ir | 3 | 0 | Ph | P1 | F | H | H | CF3 | H | H | H | H |
384 | Ir | 3 | 0 | Ph | P1 | H | CF3 | F | H | H | H | H | H |
385 | Ir | 3 | 0 | Ph | P1 | H | CF3 | F | CF3 | H | H | H | H |
386 | Ir | 3 | 0 | Ph | P1 | H | H | F | CF3 | H | H | H | H |
387 | Ir | 3 | 0 | Ph | P1 | F | CF3 | F | H | H | H | H | H |
388 | Ir | 3 | 0 | Ph | P1 | F | H | F | CF3 | H | H | H | H |
389 | Ir | 3 | 0 | Ph | P1 | H | CH3 | F | H | H | H | H | H |
390 | Ir | 3 | 0 | Ph | P1 | H | CH3 | CF3 | H | H | H | H | H |
391 | Ir | 3 | 0 | Ph | P1 | F | CF3 | H | CF3 | H | H | H | H |
392 | Ir | 3 | 0 | Ph | P1 | CF3 | H | F | H | H | H | H | H |
393 | Ir | 3 | 0 | Ph | P1 | H | CF3 | F | H | H | CH3 | H | H |
394 | Ir | 3 | 0 | Ph | P1 | H | CF3 | F | CF3 | H | CH3 | H | H |
395 | Ir | 3 | 0 | Ph | P1 | H | H | F | CF3 | H | CH3 | H | H |
396 | Ir | 3 | 0 | Ph | P1 | F | CF3 | F | H | H | CH3 | H | H |
397 | Ir | 3 | 0 | Ph | P1 | F | H | F | CF3 | H | CH3 | H | H |
398 | Ir | 3 | 0 | Ph | P1 | F | CF3 | F | CF3 | H | CH3 | H | H |
399 | Ir | 3 | 0 | Ph | P1 | F | CF3 | H | H | H | H | CH3 | H |
400 | Ir | 3 | 0 | Ph | P1 | F | CF3 | H | CF3 | H | H | CH3 | H |
401 | Ir | 3 | 0 | Ph | P1 | F | H | H | CF3 | H | H | CH3 | H |
402 | Ir | 3 | 0 | Ph | P1 | H | CF3 | F | H | H | H | CH3 | H |
403 | Ir | 3 | 0 | Ph | P1 | H | CF3 | F | CF3 | H | H | CH3 | H |
404 | Ir | 3 | 0 | Ph | P1 | H | H | F | CF3 | H | H | CH3 | H |
405 | Ir | 3 | 0 | Ph | P1 | F | CF3 | F | H | H | H | CH3 | H |
406 | Ir | 3 | 0 | Ph | P1 | F | H | F | CF3 | H | H | CH3 | H |
407 | Ir | 3 | 0 | Ph | P1 | F | CF3 | F | CF3 | H | H | CH3 | H |
408 | Ir | 3 | 0 | Ph | P1 | F | H | H | H | H | CF3 | H | H |
409 | Ir | 3 | 0 | Ph | P1 | H | F | H | H | H | CF3 | H | H |
410 | Ir | 3 | 0 | Ph | P1 | H | H | F | H | H | CF3 | H | H |
411 | Ir | 3 | 0 | Ph | P1 | H | H | H | F | H | CF3 | H | H |
412 | Ir | 3 | 0 | Ph | P1 | F | H | H | H | H | H | CF3 | H |
413 | Ir | 3 | 0 | Ph | P1 | H | F | H | H | H | H | CF3 | H |
414 | Ir | 3 | 0 | Ph | P1 | H | H | F | H | H | H | CF3 | H |
415 | Ir | 3 | 0 | Ph | P1 | H | H | H | F | H | H | CF3 | H |
416 | Ir | 3 | 0 | Ph | P1 | H | F | H | F | H | CF3 | H | H |
417 | Ir | 3 | 0 | Ph | P1 | H | F | H | F | H | CF3 | H | H |
418 | Ir | 3 | 0 | Ph | P1 | H | F | H | F | H | CF3 | H | H |
419 | Ir | 3 | 0 | Ph | P1 | H | F | H | F | H | CF3 | H | H |
420 | Ir | 3 | 0 | Ph | P1 | H | F | H | F | H | H | CF3 | H |
表1-8
No | M | A | B | E | J | G | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 | ||
421 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | F | H | F | H | H | CF3 | H |
422 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | F | H | F | H | H | CF3 | H |
423 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | F | H | F | H | H | CF3 | H |
424 | Ir | 3 | 0 | Ph | P1 | - | - | - | CF3 | H | H | H | H | CF3 | H | H |
425 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | CF3 | H | H | H | CF3 | H | H |
426 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | H | CF3 | H | H | CF3 | H | H |
427 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | H | H | CF3 | H | CF3 | H | H |
428 | Ir | 3 | 0 | Ph | P1 | - | - | - | CF3 | H | H | H | H | H | CF3 | H |
429 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | CF3 | H | H | H | H | CF3 | H |
430 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | H | CF3 | H | H | H | CF3 | H |
431 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | H | H | CF3 | H | H | CF3 | H |
432 | Ir | 3 | 0 | Ph | P1 | - | - | - | CF3 | H | CF3 | H | H | CF3 | H | H |
433 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | F | CF3 | H | H | CF3 | H | H |
434 | Ir | 3 | 0 | Ph | P1 | - | - | - | CF3 | H | CF3 | H | H | CF3 | H | H |
435 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | H | H | CF3 | H | CF3 | H | H |
436 | Ir | 3 | 0 | Ph | P1 | - | - | - | CF3 | H | CF3 | H | H | H | CF3 | H |
437 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | F | CF3 | H | H | H | CF3 | H |
438 | Ir | 3 | 0 | Ph | P1 | - | - | - | CF3 | H | CF3 | H | H | H | CF3 | H |
439 | Ir | 3 | 0 | Ph | P1 | - | - | - | H | H | H | CF3 | H | H | CF3 | H |
440 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | CH3 | H | H | H | H | H | H | H |
441 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | CH3 | H | H | H | H | H | H |
442 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | CH3 | H | H | H | H | H |
443 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | H | CH3 | H | H | H | H |
444 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | C2H5 | H | H | H | H | H | H | H |
445 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | C2H5 | H | H | H | H | H | H |
446 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | C2H5 | H | H | H | H | H |
447 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | H | C2H5 | H | H | H | H |
448 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | C3H7 | H | H | H | H | H | H | H |
449 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | C3H7 | H | H | H | H | H | H |
450 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | C3H7 | H | H | H | H | H |
451 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | H | C3H7 | H | H | H | H |
452 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | C4H9 | H | H | H | H | H | H | H |
453 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | C4H9 | H | H | H | H | H | H |
454 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | C4H9 | H | H | H | H | H |
455 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | H | C4H9 | H | H | H | H |
456 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | C6H13 | H | H | H | H | H | H | H |
457 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | - | C6H13 | H | H | H | H | H | H |
458 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | C6H13 | H | H | H | H | H |
459 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | H | C6H13 | H | H | H | H |
460 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | C8H17 | H | H | H | H | H | H | H |
461 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | C8H17 | H | H | H | H | H | H |
462 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | C8H17 | H | H | H | H | H |
463 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | H | C8H17 | H | H | H | H |
464 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | C12H25 | H | H | H | H | H | H | H |
465 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | C12H25 | H | H | H | H | H | H |
466 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | C12H25 | H | H | H | H | H |
467 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | H | C12H25 | H | H | H | H |
468 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | C15H3 | H | H | H | H | H | H | H |
469 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | C15H3 | H | H | H | H | H | H |
470 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | C15H31 | H | H | H | H | H |
471 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | H | C15H31 | H | H | H | H |
472 | Ir | 2 | 1 | Ph | P1 | CH3 | CH3 | CH3 | H | H | H | H | H | H | H | H |
473 | Ir | 2 | 1 | Ph | P1 | CH3 | F | CH3 | H | H | H | H | H | H | H | H |
474 | Ir | 2 | 1 | Ph | P1 | CF3 | CH3 | CF3 | H | H | H | H | H | H | H | H |
475 | Ir | 2 | 1 | Ph | P1 | CF3 | F | CF3 | H | H | H | H | H | H | H | H |
476 | Ir | 2 | 1 | Ph | P1 | CH3 | CF3 | CH3 | H | H | H | H | H | H | H | H |
477 | Ir | 2 | 1 | Ph | P1 | C4H9 | F | C4H9 | H | H | H | H | H | H | H | H |
478 | Ir | 2 | 1 | Ph | P1 | CH3 | C2H5 | CH3 | H | H | H | H | H | H | H | H |
479 | Ir | 2 | 1 | Ph | P1 | CH3 | C4H9 | CH3 | H | H | H | H | H | H | H | H |
480 | Ir | 2 | 1 | Ph | P1 | CH3 | CH3 | CH3 | H | CH3 | H | H | H | H | H | H |
表1-9
No | M | m | n | A | B | E | J | G | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
481 | Ir | 2 | 1 | Ph | P1 | CH3 | F | CH3 | H | CH3 | H | H | H | H | H | H |
482 | Ir | 2 | 1 | Ph | P1 | CF3 | CH3 | CF3 | H | CH3 | H | H | H | H | H | H |
483 | Ir | 2 | 1 | Ph | P1 | CF3 | F | CF3 | H | CH3 | H | H | H | H | H | H |
484 | Ir | 2 | 1 | Ph | P1 | CH3 | CF3 | CH3 | H | CH3 | H | H | H | H | H | H |
485 | Ir | 2 | 1 | Ph | P1 | C4H9 | F | C4H9 | H | CH3 | H | H | H | H | H | H |
486 | Ir | 2 | 1 | Ph | P1 | CH3 | C2H5 | CH3 | H | CH3 | H | H | H | H | H | H |
487 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | F | H | H | H | H | H | H |
488 | Ir | 2 | 1 | Ph | P1 | CH3 | CH3 | CH3 | H | F | H | H | H | H | H | H |
489 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | F | H | H | H | H | H |
490 | Ir | 2 | 1 | Ph | P1 | CF3 | CH3 | CF3 | H | F | H | H | H | H | H | H |
491 | Ir | 2 | 1 | Ph | P1 | CF3 | F | CF3 | H | F | H | H | H | H | H | H |
492 | Ir | 2 | 1 | Ph | P1 | CH3 | CF3 | CH3 | H | F | H | H | H | H | H | H |
493 | Ir | 2 | 1 | Ph | P1 | C4H9 | F | C4H9 | H | F | H | H | H | H | H | H |
494 | Ir | 2 | 1 | Ph | P1 | CH3 | C2H5 | CH3 | H | F | H | H | H | H | H | H |
495 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | CF3 | H | H | H | H | H | H |
496 | Ir | 2 | 1 | Ph | P1 | CH3 | CH3 | CH3 | H | CF3 | H | H | H | H | H | H |
497 | Ir | 2 | 1 | Ph | P1 | CH3 | F | CH3 | H | CF3 | H | H | H | H | H | H |
498 | Ir | 2 | 1 | Ph | P1 | CF3 | CH3 | CF3 | H | CF3 | H | H | H | H | H | H |
499 | Ir | 2 | 1 | Ph | P1 | CF3 | F | CF3 | H | CF3 | H | H | H | H | H | H |
500 | Ir | 2 | 1 | Ph | P1 | CH3 | CF3 | CH3 | H | CF3 | H | H | H | H | H | H |
501 | Ir | 2 | 1 | Ph | P1 | C4H9 | F | C4H9 | H | CF3 | H | H | H | H | H | H |
502 | Ir | 2 | 1 | Ph | P1 | CH3 | C2H5 | CH3 | H | CF3 | H | H | H | H | H | H |
503 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | H | H | H | CH3 | H | H |
504 | Ir | 2 | 1 | Ph | P1 | CH3 | CH3 | CH3 | H | H | H | H | H | CH3 | H | H |
505 | Ir | 2 | 1 | Ph | P1 | CH3 | F | CH3 | H | H | H | H | H | CH3 | H | H |
506 | Ir | 2 | 1 | Ph | P1 | CF3 | CH3 | CF3 | H | H | H | H | H | CH3 | H | H |
507 | Ir | 2 | 1 | Ph | P1 | CF3 | F | CF3 | H | H | H | H | H | CH3 | H | H |
508 | Ir | 2 | 1 | Ph | P1 | CH3 | CF3 | CH3 | H | H | H | H | H | CH3 | H | H |
509 | Ir | 2 | 1 | Ph | P1 | C4H9 | F | C4H9 | H | H | H | H | H | CH3 | H | H |
510 | Ir | 2 | 1 | Ph | P1 | CH3 | C2H5 | CH3 | H | H | H | H | H | CH3 | H | H |
511 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | H | H | H | H | H | CH3 | H |
512 | Ir | 2 | 1 | Ph | P1 | CH3 | CH3 | CH3 | H | H | H | H | H | H | CH3 | H |
513 | Ir | 2 | 1 | Ph | P1 | CH3 | F | CH3 | H | H | H | H | H | H | CH3 | H |
514 | Ir | 2 | 1 | Ph | P1 | CF3 | CH3 | CF3 | H | H | H | H | H | H | CH3 | H |
515 | Ir | 2 | 1 | Ph | P1 | CF3 | F | CF3 | H | H | H | H | H | H | CH3 | H |
516 | Ir | 2 | 1 | Ph | P1 | CH3 | CF3 | CH3 | H | H | H | H | H | H | CH3 | H |
517 | Ir | 2 | 1 | Ph | P1 | C4H9 | F | C4H9 | H | H | H | H | H | H | CH3 | H |
518 | Ir | 2 | 1 | Ph | P1 | CH3 | C2H5 | CH3 | H | H | H | H | H | H | CH3 | H |
519 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | CF3 | F | H | H | CH3 | H | H |
520 | Ir | 2 | 1 | Ph | P1 | CH3 | CH3 | CH3 | H | CF3 | F | H | H | CH3 | H | H |
521 | Ir | 2 | 1 | Ph | P1 | CH3 | F | CH3 | H | CF3 | F | H | H | CH3 | H | H |
522 | Ir | 2 | 1 | Ph | P1 | CF3 | CH3 | CF3 | H | CF3 | F | H | H | CH3 | H | H |
523 | Ir | 2 | 1 | Ph | P1 | CF3 | F | CF3 | H | CF3 | F | H | H | CH3 | H | H |
524 | Ir | 2 | 1 | Ph | P1 | CH3 | CF3 | CH3 | H | CF3 | F | H | H | CH3 | H | H |
525 | Ir | 2 | 1 | Ph | P1 | C4H19 | F | C4H9 | H | CF3 | F | H | H | CH3 | H | H |
526 | Ir | 2 | 1 | Ph | P1 | CH3 | C2H5 | CH3 | H | CF3 | F | H | H | CH3 | H | H |
527 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | F | H | F | H | H | H | CH3 | H |
528 | Ir | 2 | 1 | Ph | P1 | CH3 | CH3 | CH3 | F | H | F | H | H | H | CH3 | H |
529 | Ir | 2 | 1 | Ph | P1 | CH3 | F | CH3 | F | H | F | H | H | H | CH3 | H |
530 | Ir | 2 | 1 | Ph | P1 | CF3 | CH3 | CF3 | F | H | F | H | H | H | CH3 | H |
531 | Ir | 2 | 1 | Ph | P1 | CF3 | F | CF3 | F | H | F | H | H | H | CH3 | H |
532 | Ir | 2 | 1 | Ph | P1 | CH3 | CF3 | CH3 | F | H | F | H | H | H | CH3 | H |
533 | Ir | 2 | 1 | Ph | P1 | C4H9 | F | C4H9 | F | H | F | H | H | H | CH3 | H |
534 | Ir | 2 | 1 | Ph | P1 | CH3 | C2H5 | CH3 | F | H | F | H | H | H | CH3 | H |
535 | Ir | 2 | 1 | Ph | P1 | CH3 | H | CH3 | H | F | H | F | H | H | H | H |
536 | Ir | 2 | 1 | Ph | P1 | CH3 | CH3 | CH3 | H | F | H | F | H | H | H | H |
537 | Ir | 2 | 1 | Ph | P1 | CH3 | F | CH3 | H | F | H | F | H | H | H | H |
538 | Ir | 2 | 1 | Ph | P1 | CF3 | CH3 | CF3 | H | F | H | F | H | H | CH3 | H |
539 | Ir | 2 | 1 | Ph | P1 | CF3 | F | CF3 | H | H | F | H | H | H | CF3 | H |
540 | Ir | 2 | 1 | Ph | P1 | CH3 | CF3 | CH3 | H | H | F | H | H | H | CF3 | H |
表1-10
No | M | m | n | A | B | 3′orB | E | J | G | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
541 | Ir | 2 | 1 | Ph | P1 | - | C4H9 | F | C4H9 | H | H | F | H | H | H | CF3 | H |
542 | Ir | 2 | 1 | Ph | P1 | - | CH3 | C2H5 | CH3 | H | H | F | H | H | H | CF3 | H |
543 | Ir | 2 | 1 | Ph | P1 | - | CH3 | H | CH3 | H | H | F | H | H | CF3 | H | H |
544 | Ir | 2 | 1 | Ph | P1 | - | CH3 | CH3 | CH3 | H | H | F | H | H | CF3 | H | H |
545 | Ir | 2 | 1 | Ph | P1 | - | CH3 | F | CH3 | H | H | F | H | H | CF3 | H | H |
546 | Ir | 2 | 1 | Ph | P1 | - | CF3 | CH3 | CF3 | H | H | F | H | H | CF3 | H | H |
547 | Ir | 2 | 1 | Ph | P1 | - | CF3 | F | CF3 | H | H | F | H | H | CF3 | H | H |
548 | Ir | 2 | 1 | Ph | P1 | - | CH3 | CF3 | CH3 | H | H | F | H | H | CF3 | H | H |
549 | Ir | 2 | 1 | Ph | P1 | - | C4H9 | F | C4H9 | H | H | F | H | H | CF3 | H | H |
550 | Ir | 2 | 1 | Ph | P1 | - | CH3 | C2H5 | CH3 | H | H | F | H | H | CF3 | H | H |
551 | Ir | 2 | 1 | Ph | P1 | - | CH3 | H | CH3 | H | CF3 | F | H | H | H | H | H |
552 | Ir | 2 | 1 | Ph | P1 | - | CH3 | CH3 | CH3 | H | CF3 | F | H | H | H | H | H |
553 | Ir | 2 | 1 | Ph | P1 | - | CH3 | F | CH3 | H | CF3 | F | H | H | H | H | H |
554 | Ir | 2 | 1 | Ph | P1 | - | CF3 | CH3 | CF3 | H | CF3 | F | H | H | H | H | H |
555 | Ir | 2 | 1 | Ph | P1 | - | CF3 | F | CF3 | H | CF3 | F | H | H | H | H | H |
556 | Ir | 2 | 1 | Ph | P1 | - | CH3 | CF3 | CH3 | H | CF3 | F | H | H | H | H | H |
557 | Ir | 2 | 1 | Ph | P1 | - | C4H9 | F | C4H9 | H | CF3 | F | H | H | H | H | H |
558 | Ir | 2 | 1 | Ph | P1 | - | CH3 | C2H5 | CH3 | H | CF3 | F | H | H | H | H | H |
559 | Ir | 2 | 1 | Ph | P1 | - | CH3 | H | CH3 | H | CF3 | F | H | H | H | CH3 | H |
560 | Ir | 2 | 1 | Ph | P1 | - | CH3 | CH3 | CH3 | H | CF3 | F | H | H | H | CH3 | H |
561 | Ir | 2 | 1 | Ph | P1 | - | CH3 | F | CH3 | H | CF3 | F | H | H | H | CH3 | H |
562 | Ir | 2 | 1 | Ph | P1 | - | CF3 | CH3 | CF3 | H | CF3 | F | H | H | H | CH3 | H |
563 | Ir | 2 | 1 | Ph | P1 | - | CF3 | F | CF3 | H | CF3 | F | H | H | H | CH3 | H |
564 | Ir | 2 | 1 | Ph | P1 | - | CH3 | CF3 | CH3 | H | CF3 | F | H | H | H | CH3 | H |
565 | Ir | 2 | 1 | Ph | P1 | - | C4H9 | F | C4H9 | H | CF3 | F | H | H | H | CH3 | H |
566 | Ir | 2 | 1 | Ph | P1 | - | CH3 | C2H5 | CH3 | H | CF3 | F | H | H | H | CH3 | H |
567 | Ir | 2 | 1 | Ph | P1 | - | CH3 | H | CH3 | H | CF3 | H | CF3 | H | H | H | H |
568 | Ir | 2 | 1 | Ph | P1 | - | CH3 | CH3 | CH3 | H | CF3 | H | CF3 | H | H | H | H |
569 | Ir | 2 | 1 | Ph | P1 | - | CH3 | F | CH3 | H | CF3 | H | CF3 | H | H | H | H |
570 | Ir | 2 | 1 | Ph | P1 | - | CF3 | CH3 | CF3 | H | CF3 | H | CF3 | H | H | H | H |
571 | Ir | 2 | 1 | Ph | P1 | - | CF3 | F | CF3 | H | CF3 | H | CF3 | H | H | H | H |
572 | Ir | 2 | 1 | Ph | P1 | - | CH3 | CF3 | CH3 | H | CF3 | H | CF3 | H | H | H | H |
573 | Ir | 2 | 1 | Ph | P1 | - | C4H9 | F | C4H9 | H | CF3 | H | CF3 | H | H | H | H |
574 | Ir | 2 | 1 | Ph | P1 | - | CH3 | C2H5 | CH3 | H | CF3 | H | CF3 | H | H | H | H |
575 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | H | H | H | H | H | C4H9 | H |
576 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | F | H | H | H | H | H | C4H9 | H |
577 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | F | H | H | H | H | C4H9 | H |
578 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | H | F | H | H | H | C4H9 | H |
579 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | H | H | F | H | H | C4H9 | H |
580 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | F | H | F | H | H | H | C4H9 | H |
581 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | F | H | F | H | H | C4H9 | H |
582 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | F | F | H | H | H | C4H9 | H |
583 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | F | H | H | F | H | H | C4H9 | H |
584 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | F | F | F | F | H | H | C4H9 | H |
585 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | CF3 | H | H | H | H | C4H9 | H |
586 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | H | H | CF3 | H | H | C4H9 | H |
587 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | CF3 | H | CF3 | H | H | C4H9 | H |
588 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | CF3 | F | H | H | H | C4H9 | H |
589 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | F | CF3 | F | H | H | H | C4H9 | H |
590 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | F | CF3 | H | H | H | H | C4H9 | H |
591 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | H | F | CF3 | H | H | C4H9 | H |
592 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | F | H | H | CF3 | H | H | C4H9 | H |
593 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | F | H | F | CF3 | H | H | C4H9 | H |
594 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | CH3 | H | H | H | H | C4H9 | H |
595 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | H | CH3 | H | H | H | C4H9 | H |
596 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | C2H5 | H | H | H | H | C4H9 | H |
597 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | H | C2H5 | H | H | H | C4H9 | H |
598 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | C4H9 | H | H | H | H | C4H9 | H |
599 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | H | H | C4H9 | H | H | H | C4H9 | H |
600 | Ir | 2 | 1 | Ph | P1 | P1 | - | - | - | F | H | H | H | H | H | H | H |
表1-11
No | M | m | n | A | B | B′orB" | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
601 | Ir | 2 | 1 | Ph | P1 | P1 | H | F | H | H | H | H | H | H |
602 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | F | H | H | H | H | H |
603 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | H | F | H | H | H | H |
604 | Ir | 2 | 1 | Ph | P1 | P1 | H | F | H | F | H | H | H | H |
605 | Ir | 2 | 1 | Ph | P1 | P1 | H | F | F | H | H | H | H | H |
606 | Ir | 2 | 1 | Ph | P1 | P1 | F | H | H | F | H | H | H | H |
607 | Ir | 2 | 1 | Ph | P1 | P1 | F | F | F | F | H | H | H | H |
608 | Ir | 2 | 1 | Ph | P1 | P1 | H | CF3 | H | H | H | H | H | H |
609 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | H | CF3 | H | H | H | H |
610 | Ir | 2 | 1 | Ph | P1 | P1 | H | CF3 | H | CF3 | H | H | H | H |
611 | Ir | 2 | 1 | Ph | P1 | P1 | H | CF3 | F | H | H | H | H | H |
612 | Ir | 2 | 1 | Ph | P1 | P1 | F | CF3 | F | H | H | H | H | H |
613 | Ir | 2 | 1 | Ph | P1 | P1 | F | CF3 | H | H | H | H | H | H |
614 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | F | CF3 | H | H | H | H |
615 | Ir | 2 | 1 | Ph | P1 | P1 | F | H | H | CF3 | H | H | H | H |
616 | Ir | 2 | 1 | Ph | P1 | P1 | F | H | F | CF3 | H | H | H | H |
617 | Ir | 2 | 1 | Ph | P1 | P1 | H | CH3 | H | H | H | H | H | H |
618 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | CH3 | H | H | H | H | H |
619 | Ir | 2 | 1 | Ph | P1 | P1 | H | C2H5 | H | H | H | H | H | H |
620 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | C2H5 | H | H | H | H | H |
621 | Ir | 2 | 1 | Ph | P1 | P1 | H | C4H9 | H | H | H | H | H | H |
622 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | C4H9 | H | H | H | H | H |
623 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | H | H | H | H | H | CH3 |
624 | Ir | 2 | 1 | Ph | P1 | P1 | F | H | H | H | H | H | H | CH3 |
625 | Ir | 2 | 1 | Ph | P1 | P1 | H | F | H | H | H | H | H | CH3 |
626 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | F | H | H | H | H | CH3 |
627 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | H | F | H | H | H | CH3 |
628 | Ir | 2 | 1 | Ph | P1 | P1 | F | H | F | H | H | H | H | CH3 |
629 | Ir | 2 | 1 | Ph | P1 | P1 | H | F | H | F | H | H | H | CH3 |
630 | Ir | 2 | 1 | Ph | P1 | P1 | H | F | F | H | H | H | H | CH3 |
631 | Ir | 2 | 1 | Ph | P1 | P1 | F | H | H | F | H | H | H | CH3 |
632 | Ir | 2 | 1 | Ph | P1 | P1 | F | F | F | F | H | H | H | CH3 |
633 | Ir | 2 | 1 | Ph | P1 | P1 | H | CF3 | H | H | H | H | H | CH3 |
634 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | H | CF3 | H | H | H | CH3 |
635 | Ir | 2 | 1 | Ph | P1 | P1 | H | CF3 | H | CF3 | H | H | H | CH3 |
636 | Ir | 2 | 1 | Ph | P1 | P1 | H | CF3 | F | H | H | H | H | CH3 |
637 | Ir | 2 | 1 | Ph | P1 | P1 | F | CF3 | F | H | H | H | H | CH3 |
638 | Ir | 2 | 1 | Ph | P1 | P1 | F | CF3 | H | H | H | H | H | CH3 |
639 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | F | CF3 | H | H | H | CH3 |
640 | Ir | 2 | 1 | Ph | P1 | P1 | F | H | H | CF3 | H | H | H | CH3 |
641 | Ir | 2 | 1 | Ph | P1 | P1 | F | H | F | CF3 | H | H | H | CH3 |
642 | Ir | 2 | 1 | Ph | P1 | P1 | H | CH3 | H | H | H | H | H | CH3 |
643 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | CH3 | H | H | H | H | CH3 |
644 | Ir | 2 | 1 | Ph | P1 | P1 | H | C2H5 | H | H | H | H | H | CH3 |
645 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | C2H5 | H | H | H | H | CH3 |
646 | Ir | 2 | 1 | Ph | P1 | P1 | H | C4H9 | H | H | H | H | H | CH3 |
647 | Ir | 2 | 1 | Ph | P1 | P1 | H | H | C4H9 | H | H | H | H | CH3 |
648 | Ir | 3 | 0 | Ph | P2 | - | H | H | CH3 | H | H | H | H | - |
649 | Ir | 3 | 0 | Ph | P2 | - | H | H | C4H9 | H | H | H | H | - |
650 | Ir | 3 | 0 | Ph | P2 | - | F | H | F | H | H | H | H | - |
651 | Ir | 3 | 0 | Ph | P2 | - | H | H | F | H | H | H | H | - |
652 | Ir | 3 | 0 | Ph | P2 | - | H | CF3 | H | H | H | H | H | - |
653 | Ir | 3 | 0 | Ph | P2 | - | H | H | H | H | H | H | H | - |
654 | Ir | 3 | 0 | Ph | P2 | - | H | H | H | H | H | H | H | - |
655 | Ir | 3 | 0 | Ph | P2 | - | H | H | H | H | H | H | H | - |
656 | Ir | 3 | 0 | Ph | P2 | - | H | H | H | H | H | H | CH3 | - |
657 | Ir | 3 | 0 | Ph | P2 | - | H | H | H | H | H | CH3 | H | - |
658 | Ir | 3 | 0 | Ph | P3 | - | H | H | CH3 | H | H | H | H | - |
659 | Ir | 3 | 0 | Ph | P3 | - | H | H | C4H9 | H | H | H | H | - |
660 | Ir | 3 | 0 | Ph | P3 | - | F | H | F | H | H | H | H | - |
表1-12
No | M | m | n | A | B | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
661 | Ir | 3 | 0 | Ph | P3 | H | H | F | H | H | H | H | - |
662 | Ir | 3 | 0 | Ph | P3 | H | CF3 | H | H | H | H | H | - |
663 | Ir | 3 | 0 | Ph | P3 | H | H | H | H | H | H | H | - |
664 | Ir | 3 | 0 | Ph | P3 | H | H | H | H | H | H | H | - |
665 | Ir | 3 | 0 | Ph | P3 | H | H | H | H | H | H | H | - |
666 | Ir | 3 | 0 | Ph | P3 | H | H | H | H | CH3 | H | H | - |
667 | Ir | 3 | 0 | Ph | P3 | H | H | H | H | H | CH3 | H | - |
668 | Ir | 3 | 0 | Ph | P4 | H | H | CH3 | H | H | H | H | - |
669 | Ir | 3 | 0 | Ph | P4 | H | H | C4H9 | H | H | H | H | - |
670 | Ir | 3 | 0 | Ph | P4 | F | H | F | H | H | H | H | - |
671 | Ir | 3 | 0 | Ph | P4 | H | H | F | H | H | H | H | - |
672 | Ir | 3 | 0 | Ph | P4 | H | CF3 | H | H | H | H | H | - |
673 | Ir | 3 | 0 | Ph | P4 | H | H | H | H | H | H | H | - |
674 | Ir | 3 | 0 | Ph | P4 | H | H | H | H | H | H | H | - |
675 | Ir | 3 | 0 | Ph | P4 | H | H | H | H | H | H | H | - |
676 | Ir | 3 | 0 | Ph | P4 | H | H | H | H | CH3 | H | H | - |
677 | Ir | 3 | 0 | Ph | P4 | H | H | H | H | H | CH3 | H | - |
678 | Ir | 3 | 0 | Ph | P5 | H | H | CH3 | H | H | H | H | - |
679 | Ir | 3 | 0 | Ph | P5 | H | H | C4H9 | H | H | H | H | - |
680 | Ir | 3 | 0 | Ph | P5 | H | H | F | H | H | H | H | - |
681 | Ir | 3 | 0 | Ph | P5 | H | CF3 | H | H | H | H | H | - |
682 | Ir | 3 | 0 | Ph | P5 | H | H | H | H | H | CH3 | H | - |
683 | Ir | 3 | 0 | Ph | P6 | H | H | CH3 | H | H | H | H | H |
684 | Ir | 3 | 0 | Ph | P6 | H | H | C4H9 | H | H | H | H | H |
685 | Ir | 3 | 0 | Ph | P6 | H | H | F | H | H | H | H | H |
686 | Ir | 3 | 0 | Ph | P6 | H | CF3 | H | H | H | H | H | H |
687 | Ir | 3 | 0 | Ph | P6 | H | H | H | H | H | CH3 | H | H |
688 | Ir | 3 | 0 | Ph | P7 | H | H | CH3 | H | H | H | H | H |
689 | Ir | 3 | 0 | Ph | P7 | H | H | C4H9 | H | H | H | H | H |
690 | Ir | 3 | 0 | Ph | P7 | H | H | F | H | H | H | H | H |
691 | Ir | 3 | 0 | Ph | P7 | H | CF3 | H | H | H | H | H | H |
692 | Ir | 3 | 0 | Ph | P7 | H | H | H | H | H | CH3 | H | H |
693 | Ir | 3 | 0 | Ph | P8 | H | H | CH3 | H | H | H | H | H |
694 | Ir | 3 | 0 | Ph | P8 | H | H | C4H9 | H | H | H | H | H |
695 | Ir | 3 | 0 | Ph | P8 | H | H | F | H | H | H | H | H |
696 | Ir | 3 | 0 | Ph | P8 | H | H | H | H | H | H | CH3 | H |
697 | Ir | 3 | 0 | Ph | P8 | H | H | H | H | H | CH3 | H | H |
698 | Ir | 3 | 0 | Ph | P9 | H | H | CH3 | H | H | H | H | H |
699 | Ir | 3 | 0 | Ph | P9 | H | H | C4H9 | H | H | H | H | H |
700 | Ir | 3 | 0 | Ph | P9 | H | H | F | H | H | H | H | H |
701 | Ir | 3 | 0 | Ph | P9 | H | H | H | H | H | H | CH3 | H |
702 | Ir | 3 | 0 | Ph | P9 | H | H | H | H | H | CH3 | H | H |
在下文中,基于实施例更具体地描述本发明。
沿着以下所示的合成路线合成实施例中所使用的铱金属配位化合物(在Inorg.Chem.,1994,33,p.545中公开了类似的反应)。
<<铱金属配位化合物的合成>>
以下示出了合成本发明所使用的铱络合物的工艺路线。
或
(实施例1)实施例化合物No.729的合成
在100ml的三颈烧瓶中,放置3.18g(24.9mmol)噻吩基硼酸、5.65g(25.0mmol)1-溴-4-三氟甲基吡啶、25ml甲苯、12.5ml乙醇和25ml的2M的碳酸钠水溶液,并在氮气流和室温下搅拌,接着加入0.98g(0.85mmol)四(三苯基膦)钯(O)。此后,在搅拌和氮气流下回流体系8小时。在反应完成之后,冷却反应产物,并通过加入冷水和甲苯进行萃取。用盐水洗涤有机层和用硫酸镁干燥,接着在减压下除去溶剂,得到干燥固体。通过硅胶柱色谱(洗脱剂:氯仿/甲醇=10/1)纯化残渣,获得4.20g(产率=74%)化合物A。
在100ml的四颈烧瓶中,放置50ml甘油,并在搅拌和用氮气鼓泡下,在130-140℃下加热2小时。将甘油冷却到室温并倾入到300ml的1N的盐酸中,然后过滤掉沉淀并用水洗涤。然后通过硅胶色谱,采用氯仿作为洗脱剂,纯化沉淀,获得0.33g(产率:38%)红色粉状实施例化合物No.729。
该化合物的甲苯溶液显示出表明λmax=563nm的发光光谱。通过使用装置(Bruker Co.制造的“REFLEX-III”),对该化合物进行MALDI-TOF(底物辅助激光解吸离子化飞行时间质谱)测定。在该方法中,对通过从样品物质中除去一个电子获得的离子进行其质量测量,由此所测量的质量表示为M+。该方法经常用于物质鉴定。所测量的M+值为877.0,据此证明为其目标产物。
为了证明磷光型发光,将该实施例化合物溶解在氯仿中,并独立地用氧气或氮气对该溶液充气,为了比较光致发光,各自接着进行光辐照(photoirradiation)。结果,对于充氧的溶液,基本上没有识别到归因于铱络合物的发光,而对于充氮的溶液证明了光致发光。根据这些结果,证明本发明的化合物是磷光化合物。作为参考,在荧光材料的情况下,归因于该化合物的发光甚至在充氧的溶液中也不会消失。
此外,与通常显示数纳秒到数十纳秒发光寿命的荧光材料相反,包括在下述实施例中获得的那些化合物在内的本发明的化合物,都显示出100纳秒或更长的磷光。
(实施例2)
通过与实施例1相类似的方法合成实施例化合物No.310。
甲苯溶液的发光:λmax=489nm
MALDI-TOF MS:M+=859.1
(实施例3)
通过与实施例1相类似的方法合成实施例化合物No.238。
甲苯溶液的发光:λmax=515nm
MALDI-TOF MS:M+=709.1
(实施例4)
通过与实施例1相类似的方法合成实施例化合物No.242。
甲苯溶液的发光:λmax=471nm
MALDI-TOF MS:M+=763.1
(实施例5)
通过与实施例1相类似的方法合成实施例化合物No.384。
甲苯溶液的发光:λmax=466nm
MALDI-TOF MS:M+=913.1
(实施例6)
通过与实施例1相类似的方法合成实施例化合物No.777。
甲苯溶液的发光:λmax=696nm
MALDI-TOF MS:M+=1231.1
(实施例7)
合成实施例化合物No.472。
在100ml的两颈烧瓶中,放置60ml乙氧基乙醇和20ml水,并在用氮气鼓泡之下搅拌1小时。然后,加入0.51g(4.4mmol)化合物C和0.71g(2.0mmol)三氯化铱(III)水合物,并在搅拌与氮气流下,在约100℃下加热该体系16小时。将反应产物冷却到室温并倾入到100ml水中,接着过滤回收并用水洗涤沉淀。接着将沉淀倾入到60ml乙醇中并搅拌1小时,接着过滤出并用丙酮洗涤,获得0.95g(产率:89%)黄色粉状化合物D。
在100ml的两颈烧瓶中,放置50ml乙氧基乙醇,并在用氮气鼓泡之下搅拌1小时。然后,加入0.536g(0.5mmol)化合物D、0.17g(1.4mmol)化合物E和0.75g碳酸钠Na2CO3,并在搅拌与氮气流下,在约100℃下加热该体系16小时。将反应产物冷却到室温并倾入到100ml水中,接着过滤出沉淀并用水洗涤沉淀。将沉淀倾入到70ml乙醇中,并在搅拌1小时之后,过滤出沉淀并溶解在氯仿中,接着过滤。缩合所得滤液,和用氯仿作为洗脱剂,通过硅胶柱色谱纯化,获得0.45g(产率:73%)黄色粉状实施例化合物No.472。该化合物的甲苯溶液显示出表明λmax=526nm的发光光谱。根据MALDI-TOF MS,该化合物显示出M+=614.2,和证明其为目标产物。
(实施例8)
在该实施例中,制备器件(有效显示面积=3mm2),其具有图1(c)所示的包括4层有机层的器件结构。使用无碱玻璃片材作为透明衬底15和通过喷镀形成100nm厚的氧化铟锡(ITO)膜并以透明电极14形式构图。此外,在其上以40nm的层厚真空沉积上述结构分子式表示的α-NPD,作为空穴迁移层13。然后,以30nm的层厚共同真空沉积作为基质材料的上述CBP和提供8wt%用量的实施例化合物No.729(金属配位化合物)作为有机发光层12。此外,以10nm的层厚真空沉积BCP作为激子扩散阻止层17。然后,在10-4Pa的真空下对上述的Alq3进行耐热真空沉积,形成30nm厚的有机膜,作为电子迁移层16。
在上述中,以15nm的厚度沉积AlLi合金膜作为金属电极层11的下层,和在其上真空沉积100nm厚的Al膜,形成图饰的金属电极11,该电极位于透明电极14的对面且具有3mm2的电极面积。
通过使用用于电流-电压特征的微电流仪表(“4104B”,由Hewlett-Packard Corp.制造)和用于发光的“BM7”(由Topcon K.K.制造),测量由此获得的EL器件的性能。
(实施例9)
以与实施例8相同的方式制备器件,所不同的是以7wt%的重量比使用金属配位化合物(实施例化合物No.729)。
(对比实施例1)
以与实施例8相同的方式制备器件,所不同的是以8wt%的重量比使用表2所示的金属配位化合物(729R)(其中平行地示出了与其进行比较的本发明的取代化合物)。
表2
No. | M | N | m | A | B | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
729R | Ir | 3 | 0 | Tn1 | P1 | H | H | - | - | H | H | H | H |
729 | Ir | 3 | 0 | Tn1 | P1 | H | H | - | - | H | H | CF<sub>3</sub> | H |
(对比实施例2)
以与实施例8相同的方式制备器件,所不同的是以3wt%的重量比使用表2所示的金属配位化合物(729R)。
(对比实施例3)
以与实施例8相同的方式制备器件,所不同的是以1wt%的重量比使用表2所示的金属配位化合物(729R)。
采用ITO侧作为阳极和Al侧作为阴极,对各器件施加12V/100nm的电场,测量亮度。
为了消除由于氧气或水导致的器件劣化的因素,在从真空室中取出器件之后,在干燥的氮气流下进行上述测量。
表3示出了使用各化合物的器件的结果。从表3所示的结果看出,对比实施例729R的最大发光浓度显然为1%至8%,而提供有取代基的实施例化合物No.729在8%下显示出比7%更高的亮度,和在8%下可显示出比不具有取代基的729R显著更高的亮度。
表3<亮度比较>
实施例 | 化合物No. | 浓度(wt%) | 亮度(cd/m<sup>2</sup>) |
8 | 729 | 8 | 4500 |
9 | 729 | 7 | 4250 |
对比实施例1 | 729R | 8 | 1620 |
对比实施例2 | 729R | 3 | 4000 |
对比实施例3 | 729R | 1 | 1290 |
(实施例10)
以与实施例8相同的方式制备器件,所不同的是以3wt%的重量比使用实施例2合成的金属配位化合物(310)。
(实施例11)
以与实施例8相同的方式制备器件,所不同的是以6wt%的重量比使用实施例2合成的金属配位化合物(310)。
(实施例12)
以与实施例8相同的方式制备器件,所不同的是以8wt%的重量比使用实施例2合成的金属配位化合物(310)。
(实施例13)
以与实施例8相同的方式制备器件,所不同的是以3wt%的重量比使用实施例3合成的金属配位化合物(238)。
(实施例14)
以与实施例8相同的方式制备器件,所不同的是以6wt%的重量比使用实施例3合成的金属配位化合物(238)。
(实施例15)
以与实施例8相同的方式制备器件,所不同的是以8wt%的重量比使用实施例3合成的金属配位化合物(238)。
(实施例15A)
以与实施例8相同的方式制备器件,所不同的是以11wt%的重量比使用实施例3合成的金属配位化合物(238)。
(实施例15B)
以与实施例8相同的方式制备器件,所不同的是以13wt%的重量比使用实施例3合成的金属配位化合物(238)。
(实施例16)
以与实施例8相同的方式制备器件,所不同的是以3wt%的重量比使用实施例4合成的金属配位化合物(242)。
(实施例17)
以与实施例8相同的方式制备器件,所不同的是以6wt%的重量比使用实施例4合成的金属配位化合物(242)。
(实施例18)
以与实施例8相同的方式制备器件,所不同的是以8wt%的重量比使用实施例4合成的金属配位化合物(242)。
(实施例19)
以与实施例8相同的方式制备器件,所不同的是以3wt%的重量比使用实施例5合成的金属配位化合物(384)。
(实施例20)
以与实施例8相同的方式制备器件,所不同的是以6wt%的重量比使用实施例5合成的金属配位化合物(384)。
(实施例21)
以与实施例8相同的方式制备器件,所不同的是以8wt%的重量比使用实施例5合成的金属配位化合物(384)。
(对比实施例4)
以与实施例8相同的方式制备器件,所不同的是以3wt%的重量比使用表4所示的金属配位化合物(1R)(其中平行地示出了相应实施例化合物Nos.310、238、242和384的结构)。
表4
No. | M | m | n | A | B | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
1R | Ir | 3 | 0 | Ph | P1 | H | H | H | H | H | H | H | H |
310 | Ir | 3 | 0 | Ph | P1 | H | CF<sub>3</sub> | H | H | H | H | H | H |
238 | Ir | 3 | 0 | Ph | P1 | H | F | H | H | H | H | H | H |
242 | Ir | 3 | 0 | Ph | P1 | F | H | F | H | H | H | H | H |
384 | Ir | 3 | 0 | Ph | P1 | H | CF<sub>3</sub> | F | H | H | H | H | H |
(对比实施例5)
以与实施例8相同的方式制备器件,所不同的是以6wt%的重量比使用表4所示的金属配位化合物(1R)。
(对比实施例6)
以与实施例8相同的方式制备器件,所不同的是以8wt%的重量比使用表4所示的金属配位化合物(1R)。
采用ITO侧作为阳极和AI侧作为阴极,对实施例10-12和对比实施例4-6中的各器件施加12V/100nm的电场,测量电流效率。
表5示出了使用各化合物的器件的结果。从表5所示的结果看出,得到对比化合物1R的最大电流效率的浓度显然为3%至8%,而提供有取代基的实施例化合物No.310甚至在8%下显示出电流效率的增加。
表5<电流效率的比较>
实施例 | 化合物No. | 浓度(wt%) | 电流效率(cd/A) |
10 | 310 | 3 | 2 |
11 | 310 | 6 | 2.4 |
12 | 310 | 8 | 2.7 |
对比实施例4 | 1R | 3 | 15 |
对比实施例5 | 1R | 6 | 19 |
对比实施例6 | 1R | 8 | 17 |
采用ITO侧作为阳极和Al侧作为阴极,对实施例13-15和对比实施例4-6中的各器件施加12V/100nm的电场,测量(电)功率。
表6示出了使用各化合物的器件的结果。从表6所示的结果看出,得到对比化合物1R的最大功率的浓度为3%至8%,而提供有取代基的实施例化合物(238)甚至在8%的浓度下显示出最大效率的增加。
表6<功率的比较>
实施例 | 化合物No. | 浓度(wt%) | 功率(lm/W) |
13 | 238 | 3 | 5.4 |
14 | 238 | 6 | 6 |
15 | 238 | 8 | 6.2 |
15A | 238 | 11 | 6.5 |
15B | 238 | 13 | 6.3 |
对比实施例4 | 1R | 3 | 5.7 |
对比实施例5 | 1R | 6 | 6.2 |
对比实施例6 | 1R | 8 | 6 |
采用ITO侧作为阳极和Al侧作为阴极,对实施例16-18和对比实施例4-6中的各器件施加12V/100nm的电场,测量外量子效率,这是根据基于流过器件的电流值和亮度值的亮度(Im)/电流(mA)之比来评价,其中通过采用微电流仪表(“4104B”,由Hewlett-PachardCorp.制造),使用流过器件的微电流测量流过器件的电流值和通过“BM7”(由Topcon K.K.制造)测量亮度值。
表7示出了使用各化合物的器件的结果。从表7所示的结果看出,得到对比化合物1R的最大外量子效率的浓度为3%至8%,而提供有取代基的实施例化合物(242)甚至在8%的浓度下显示出最大效率的增加。
表7<外量子效率的比较>
实施例 | 化合物No. | 浓度(wt%) | 外量子效率 |
16 | 242 | 3 | 3 |
17 | 242 | 6 | 4 |
18 | 242 | 8 | 4.2 |
对比实施例4 | 1R | 3 | 7 |
对比实施例5 | 1R | 6 | 8 |
对比实施例6 | 1R | 8 | 7.6 |
采用ITO侧作为阳极和Al侧作为阴极,对实施例19-21和对比实施例4-6中的各器件施加12V/100nm的电场,测量(电)功率。
表8示出了使用各化合物的器件的结果。从表8所示的结果看出,得到对比化合物1R的最大功率的浓度为3%至8%,而提供有取代基的实施例化合物(384)甚至在8%的浓度下显示出最大效率的增加。
表8<功率的比较>
实施例 | 化合物No. | 浓度(wt%) | 功率(lm/W) |
19 | 384 | 3 | 2 |
20 | 384 | 6 | 2.3 |
21 | 384 | 8 | 2.6 |
对比实施例4 | 1R | 3 | 5.7 |
对比实施例5 | 1R | 6 | 6.2 |
对比实施例6 | 1R | 8 | 6 |
(实施例22)
以与实施例8相同的方式制备器件,所不同的是以1wt%的重量比使用实施例6合成的金属配位化合物(777)。
(实施例23)
以与实施例8相同的方式制备器件,所不同的是以6wt%的重量比使用实施例6合成的金属配位化合物(777)。
(实施例24)
以与实施例8相同的方式制备器件,所不同的是以8wt%的重量比使用实施例6合成的金属配位化合物(777)。
(对比实施例7)
以与实施例8相同的方式制备器件,所不同的是以1wt%的重量比使用下表9所示的金属配位化合物(777R)。
表9
No. | M | m | n | A | B | A-R1 | A-R2 | A-R3 | A-R4 | B-R5 | B-R6 | B-R7 | B-R8 |
777R | Ir | 3 | 0 | Pe | P1 | H | H | H | H | H | H | H | H |
777 | Ir | 3 | 0 | Pe | P1 | H | H | H | H | H | H | CF<sub>3</sub> | H |
(对比实施例8)
以与实施例8相同的方式制备器件,所不同的是以6wt%的重量比使用表9所示的金属配位化合物(777R)。
(对比实施例9)
以与实施例8相同的方式制备器件,所不同的是以8wt%的重量比使用表9所示的金属配位化合物(777R)。
采用ITO侧作为阳极和Al侧作为阴极,对实施例22-24和对比实施例7-9中的各器件施加12V/100nm的电场,测量(电)功率。
表10示出了使用各化合物的器件的结果。从表10所示的结果看出,得到对比化合物777R的最大功率的浓度为1%至8%,而提供有取代基的实施例化合物(777)在最多8%的浓度下显示出最大效率的增加。
表10<最大功率的比较>
实施例 | 化合物No. | 浓度(wt%) | 功率(lm/W) |
22 | 777 | 1 | 0.04 |
23 | 777 | 6 | 0.12 |
24 | 777 | 8 | 0.15 |
对比实施例7 | 777R | 1 | 0.08 |
对比实施例8 | 777R | 6 | 0.15 |
对比实施例9 | 777R | 8 | 0.13 |
(实施例25)
以与实施例8相同的方式制备器件,所不同的是以3wt%的重量比使用实施例7合成的金属配位化合物(472)。
(实施例26)
以与实施例1相同的方式制备器件,所不同的是以6wt%的重量比使用实施例7合成的金属配位化合物(472)。
(对比实施例10)
以与实施例1相同的方式制备器件,所不同的是以3wt%的重量比使用以下所示的金属配位化合物(472R)。
(对比实施例11)
以与实施例1相同的方式制备器件,所不同的是以6wt%的重量比使用上述金属配位化合物(472R)。
(对比实施例12)
以与实施例1相同的方式制备器件,所不同的是以8wt%的重量比使用上述金属配位化合物(472R)。
采用ITO侧作为阳极和Al侧作为阴极,对实施例25-27和对比实施例10-12中的各器件施加12V/100nm的电场,测量功率。
为了消除由于氧气或水导致的器件劣化的因素,在从真空室中取出器件之后,在干燥的氮气流下进行上述测量。
表11示出了使用各化合物的器件的结果。从表11所示的结果看出,得到对比化合物472R的最大功率的浓度显然为3%至8%,而提供有取代基的实施例化合物(384)甚至在最多8%的浓度下显示出功率的增加。
表11<最大功率的比较>
实施例 | 化合物No. | 浓度(wt%) | 功率(lm/W) |
25 | 472 | 3 | 5.6 |
26 | 472 | 6 | 6.3 |
27 | 472 | 8 | 6.5 |
对比实施例10 | 472R | 3 | 5.4 |
对比实施例11 | 472R | 6 | 6 |
对比实施例12 | 472R | 8 | 5.8 |
(实施例28)
在200ml的三颈烧瓶中,放置3.50g(25.0mmol)4-氟苯基硼酸、3.95g(25.0mmol)1-溴吡啶、25ml甲苯、12.5ml乙醇和25ml的2M的碳酸钠水溶液,并在氮气流和室温下搅拌,接着加入0.98g(0.85mmol)四(三苯基膦)钯(O)。此后,在搅拌和氮气流下回流体系8小时。在反应完成之后,冷却反应产物并通过加入冷水和甲苯进行萃取。用盐水洗涤有机层和用硫酸镁干燥,接着在减压下除去溶剂,得到干燥固体。通过硅胶柱色谱(洗脱剂:氯仿/甲醇=10/1)纯化残渣,获得3.24g(产率=75%)化合物G。
在200ml的三颈烧瓶中,放置0.881g(2.5mmol)三水合氯化铱(III)、0.953g(5.5mmol)化合物G、75ml乙氧基乙醇和25ml水,并在室温下,在氮气流中搅拌30分钟,接着在搅拌下回流24小时。将反应产物冷却到室温,和通过沉淀回收沉淀物并按顺序用水、乙醇和丙酮洗涤。在减压下,在室温下干燥之后,获得1.32g(产率:92%)黄色粉状化合物H。
在200ml的三颈烧瓶中,放置70ml乙氧基乙醇、0.80g(0.7mmol)化合物H、0.22g(2.10mmol)乙酰丙酮和1.04g(9.91mmol)碳酸钠,并在室温下,在氮气流中搅拌1小时,接着在搅拌下回流15小时。用冰冷却反应产物,过滤出沉淀并用水洗涤。通过硅胶色谱纯化(洗脱剂:氯仿/甲醇=30/1),获得0.63g(产率:71%)黄色粉状化合物I(实施例化合物No.489)。该化合物的甲苯溶液显示出表明λmax=499nm的发光光谱。此外,根据MALDI-TOF MS,证明化合物的M+=638.7。
在100ml的三颈烧瓶中,放置0.21g(1.2mmol)化合物G、0.32g(0.5mmol)化合物I和25ml甘油,并在氮气流下在约180℃下搅拌8小时。将反应产物冷却到室温并倾入到170ml的1N的盐酸中。过滤出沉淀并用水洗涤,接着在100℃下减压干燥5小时。用氯仿作为洗脱剂,通过硅胶柱色谱纯化沉淀,获得0.22g(产率:63%)黄色粉状实施例化合物No.239。该化合物的甲苯溶液显示出表明λmax=490nm的发光光谱,和通过MALDI-TOF MS,证明化合物的M+=708.8。
(实施例29)
通过与实施例7相类似的方法合成实施例化合物No.535。
甲苯溶液的发光:λmax=525nm
MALDI-TOF MS:M+=671.1
(实施例30)
通过与实施例28相类似的方法合成实施例化合物No.243。
甲苯溶液的发光:λmax=518nm
MALDI-TOF MS:M+=762.7
(实施例31)
通过与实施例7相类似的方法合成实施例化合物No.511。
甲苯溶液的发光:λmax=514nm
MALDI-TOF MS:M+=628.1
(实施例32)
通过与实施例28相类似的方法合成实施例化合物No.56。
甲苯溶液的发光:λmax=505nm
MALDI-TOF MS:M+=697.2
(实施例33)
通过与实施例1相类似的方法合成实施例化合物No.389。
甲苯溶液的发光:λmax=503nm
(实施例34)
通过与实施例1相类似的方法合成实施例化合物No.390。
甲苯溶液的发光:λmax=507nm
(实施例35)
通过与实施例1相类似的方法合成实施例化合物No.312。
甲苯溶液的发光在458nm和488nm处显示出双峰
(实施例36)
通过与实施例1相类似的方法合成实施例化合物No.312。
(实施例37)
通过与实施例1相类似的方法合成实施例化合物No.314。
(实施例38)
通过与实施例1相类似的方法合成实施例化合物No.388。
(实施例39)
通过与实施例1相类似的方法合成实施例化合物No.392。
(实施例40)
可通过类似的方法合成实施例化合物Nos.274、346、358、393和396,所不同的是变化起始材料。
(实施例41)
在下文中,公开了显示装置的两种实例。首先,参考图2公开了具有XY-矩阵结构的图象显示装置的制备实例。
在150mm长、150mm宽和1.1mm厚的玻璃衬底21上,通过喷镀形成约100nm厚的ITO膜并构图成为100条100微米宽的透明矩阵电极(阳极侧)作为简单的矩阵电极,其间隔为40微米。然后在其上形成四层的有机化合物层23,该层中包括发光层12,而发光层12含有作为客体化合物的实施例1-7合成的化合物之一。
然后,通过掩膜真空沉积,以40微米的间隔形成100条100微米宽的金属电极24,以便其垂直于透明电极,而透明电极是在2×10-5Torr的真空下通过真空沉积得到的。随着层压10nm厚的Al/Li合金层(Li:1.3wt%),然后150nm厚的Al层,形成金属电极。
如图3所示,通过使用10V的扫描信号和±3V的数据信号,在7V到13V的电压下,在用氮气填充的手套式操作箱内,对由此获得的100×100-简单矩阵型有机EL器件进行简单的矩阵驱动。作为在30Hz的帧频下交错驱动的结果,证明各器件的发光图象。
作为图象显示装置,本发明的高效发光器件使得轻质的平板显示器具有经济的能耗和高的可识别度。作为打印机光源,可以直线排列本发明的发光器件并靠近感光鼓布置,从而提供线光闸(lineshutter)。其中各器件彼此独立地驱动,以在感光鼓上进行限定的暴光。另一方面,在作为照明器件或液晶显示装置用的后照光中的应用上,预计有能耗经济的效果。
至于在图象显示装置上的另一应用,特别有利地形成有源矩阵型图象显示装置器件,该器件配有薄膜晶体管(TFT),而不是上述XY-矩阵布线。在下文中,参考图4-6将描述本发明的有源矩阵型图象显示装置器件。
图4是这一面板的平面示意图,在面板外部四周排列着包括电源设备的驱动电路和扫描信号驱动器以及作为显示信号输入设备的数据信号驱动器(称为图象数据供给装置,其分别与电源线、称为栅极(gate)线的X-方向扫描线和称为数据线的Y-方向扫描线相连)。扫描信号驱动器循序地选择栅极扫描线,与此同时,由数据信号驱动器供给图象信号。在栅极扫描线与数据线的交叉处排列显示像素。
接下来,参考等价电路,描述像素电路操作。当将选择信号施加到栅极选择线上时,接通TFT1,以便数据信号从数据信号线传输到电容器Cadd中,从而决定TFT2的栅极电势,因此,取决于TFT2的栅极电势,电流通过电流传输线被传输到排列在各像素处的有机发光器件(EL)上。在一个帧频时间段内,TFT2的栅极电势在Cadd处得到保持,以便在这一时间段内电流连续地从电流传输线流动到EL器件上。结果,在一个帧频时间段内,保持发光。
图6是表示在该实施例中使用的TFT的截面结构简图。在玻璃衬底上,形成聚硅氧烷p-Si层,和用必须的杂质分别对沟道、漏极区和源区掺杂。此后通过栅极绝缘膜形成栅极电极,并分别形成与漏极区和源区相连接的漏极与源电极。在这一例子中,漏极与透明像素电极(ITO)通过在隔离绝缘膜内的钻孔连接。
本发明所使用的有源器件不需要特别限制,其也可以是单晶硅TFT、无定形硅α-Si TFT等。
在像素电极上,可排列多层或单层有机发光层,并按顺序层压作为阴极的金属电极,以提供有源型有机发光器件。
[工业实用性]
如上所述,相对于主体材料,可以高浓度地在发光层中使用具有高磷光效率和短磷光寿命的取代的金属配位化合物,同时防止浓度衰减。结果,根据本发明,可获得显示出高发光效率的优异的发光器件。本发明的发光器件作为显示器件也是优异的。
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KR100533556B1 (ko) | 2005-12-06 |
EP1349435A1 (en) | 2003-10-01 |
CN1478372A (zh) | 2004-02-25 |
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