CN101065389B - 过渡金属卡宾配合物在有机发光二极管(oleds)中的用途 - Google Patents
过渡金属卡宾配合物在有机发光二极管(oleds)中的用途 Download PDFInfo
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- CN101065389B CN101065389B CN2005800404714A CN200580040471A CN101065389B CN 101065389 B CN101065389 B CN 101065389B CN 2005800404714 A CN2005800404714 A CN 2005800404714A CN 200580040471 A CN200580040471 A CN 200580040471A CN 101065389 B CN101065389 B CN 101065389B
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- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
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- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
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- 235000011009 potassium phosphates Nutrition 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- 235000011091 sodium acetates Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- 238000004154 testing of material Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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Abstract
本发明涉及过渡金属-卡宾配合物在有机发光二极管(OLED)中的应用,涉及含有这些过渡金属-卡宾配合物的发光层,电子或激子的阻挡层或空穴的阻挡层,涉及包含这些过渡金属-卡宾配合物的OLED,涉及包含本发明OLED的器件以及涉及过渡金属-卡宾配合物。
Description
本发明涉及过渡金属-卡宾配合物在有机发光二极管(OLED)中的用途,各自包含这些过渡金属-卡宾配合物的发光层、电子或激子的阻挡层或空穴阻挡层,包含这些过渡金属-卡宾配合物的OLED,包含本发明的OLED的器件以及过渡金属-卡宾配合物。
在有机发光二极管(OLED)中,利用材料在借助电流激发时的发光性能。OLED作为用于生产平板可视显示单元的阴极射线管和液晶显示器的替代品特别令人感兴趣。包含OLED的器件由于非常紧凑的结构和固有的低能耗,它们特别适于移动应用,例如用于移动电话、便携式电脑等中。
已经提出了许多借助电流激发而发光的材料。
WO 02/15645涉及具有包含磷光过渡金属化合物的发光层的OLED。这些过渡金属化合物尤其在可见电磁光谱的蓝色区域显示电致磷光。然而,由WO 02/15645中所公开的配合物发出的蓝光的颜色座标需要改进。
WO 01/41512涉及具有包含通式L2MX的分子的发光层的OLED,其中M更优选为铱且L选自2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、7,8-苯并喹啉、香豆素、噻吩基吡啶、苯基吡啶、苯并噻吩基吡啶、3-甲氧基-2-苯基吡啶和甲苯基吡啶,且X选自乙酰丙酮根、六氟乙酰丙酮根、亚水杨基、甲基吡啶根和8-羟基喹啉根。
WO 00/70655涉及包含磷光有机金属铱化合物或锇化合物作为发光物质的电致发光层。优选使用三(2-苯基吡啶)铱作为发光化合物。
尽管在电磁光谱的蓝色、红色和绿色区域显示电致发光的化合物是已知的,但需要提供工业上有用的更有效化合物。电致发光指电致荧光和电致磷光。此外,提供用作阻挡电子、激子或空穴的材料的其他化合物也令人感兴趣。
因此,本申请的目的是提供适合在电磁光谱的可见区中电致发光的化合物。本申请的另一目的是提供用作阻挡电子、激子或空穴的材料的化合物。
这些目的通过使用不带电的通式I的过渡金属配合物而实现:
其中各变量如下所定义:
M为选自Co、Rh、Ir、Nb、Pd、Pt、Fe、Ru、Os、Cr、Mo、W、Mn、Re、Cu、Ag和Au的金属原子,对于特定金属原子呈任何可能的氧化态;
L为可以是单齿或二齿的单阴离子或双阴离子配体;
K为选自如下的不带电的单齿或二齿配体:膦;膦酸酯及其衍生物,砷酸酯及其衍生物;亚磷酸酯;CO;吡啶类;腈类,与M形成π-配合物的单烯烃和共轭二烯;
n为卡宾配体数目,其中n至少为1且式I配合物中的卡宾配体在n>1时可以相同或不同;
m为配体L的数目,其中m可以为0或≥1且配体L在m>1时可以相同或不同;
q为配体K的数目,其中q可以为0或≥1且配体K在q>1时可以相同或不同;
其中n+m+q之和取决于所用金属原子的氧化态和配位数以及配体的齿数(denticity)和电荷,条件是n至少为1;
Do为选自N、O和S的配位原子;
r在Do为N时为1且在Do为O或S时为0;
Y1、Y2各自独立地为氢、烷基、链烯基、炔基、芳基或杂芳基;
或
Y1和Y2与它们所键合的碳原子一起形成可以包含1个或2个氮原子并且任选稠合于另一环的6员芳族环,其中所述另一环任选稠合并且任选包含杂原子;
Y3为氢或烷基;
或
Y3和Y2与配位原子Do和与Y2所键合的碳原子一起形成5或6员环,该环除了配位原子Do外还可以另外包含选自N、O和S的杂原子;
A为具有3或4个原子的桥键,其中一个或两个原子可以为杂原子且剩余原子为碳原子,从而使如下基团
形成5员杂芳族环或6员芳族或杂芳族环,所述环各自任选被选自如下的取代基取代:烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、卤素、CN、CHO、烷基羰基、芳基羰基、羧基、烷氧羰基、芳氧羰基、羟基磺酰基、烷氧基磺酰基、芳氧基磺酰基、NO2和NO,并任选与另一任选稠合且任选包含杂原子的环稠合,
其中Y1与选自化学单键、C(Y4)2、C(O)、O、S、S(O)、SO2和NY5的基团一起可以任选形成2员桥键B,该桥键B连接于桥键A中位于与卡宾配体的卡宾单元的氮原子键合的碳原子的α位的碳原子或杂原子;
Y4、Y5各自独立地为氢、烷基、芳基或杂芳基,且C(Y4)2桥中的两个Y4 基团可以相互独立地变化。
式I的过渡金属配合物可以用于OLED的任何层中,并且配体骨架或中心金属可以变化以调节为所需的金属配合物性能。例如可以在OLED的电子阻挡层、激子阻挡层、空穴阻挡层、空穴传输层、电子传输层或发光层中使用式I的过渡金属配合物。优选将式I化合物在OLED中用作发光剂分子。
二齿配体是指在两个位置与过渡金属原子M配位的配体。单齿配体指在该配体上的一个位置与过渡金属原子M配位的配体。
取决于所用金属M的配位数、所用配体L和K的性质和类型以及卡宾配体的数目,对于相同金属M、相同类型和数目的所用配体K和L以及相同数目的卡宾配体可以存在相应金属配合物的不同异构体。例如在配合物具有的金属M的配位数为6(即八面体配合物)的情况下,例如对于Ir(III)配合物,当该配合物的通用组成为MA2B4时可能存在顺式/反式异构 体,而当该配合物的通用组成为MA3B3时可能存在面-经异构体(面式/经式异构体)。在正方平面配合物具有的金属M的配位数为4的情况下,例如对于Pt(II)配合物,在该配合物具有通用组成MA2B2时可能存在顺式/反式异构体。变量A和B各自为配体的结合点,并且不仅可以存在单齿配体,而且可以存在二齿配体。根据上述通用组成,不对称二齿配体具有一个A基团和一个B基团,而对称配体具有两个A基团或两个B基团。
本领域熟练技术人员应理解顺式/反式和面-经异构体的意义。在八面体配合物中,顺式异构是指在组成为MA2B4的配合物中两个A基团占据八面体的相邻角,而在反式异构中两个A基团互相占据八面体的相对角。在组成为MA3B3的配合物情况下,相同类型的三个基团可以占据一个八面体面的角(面式异构体)或者占据经线,即三个配体的结合点中的两个相互呈反式(经式异构体)。对于八面体金属配合物中顺式/反式异构体和面-经异构体的定义,例如参见J.Huheey,E.Keiter,R.Keiter,AnorganischeChemie:Prinzipien von Struktur und [无机化学:结构和反应性原理],第2版,新修订版,被翻译成德文并且由Ralf Steudel扩展,Berlin;New York:de Gruyter,1995,第575、576页。
在正方平面配合物中,顺式异构是指在组成为MA2B2的配合物中,两个A基团和两个B基团均占据正方形的相邻角,而在反式异构的情况下,两个A基团和两个B基团各自占据正方形的两个对角。对于正方平面金属配合物中顺式/反式异构体的定义,例如参见J.Huheey,E.Keiter,R,Keiter,Anorganische Chemie:Prinzipien von Struktur und 第2版,新修订版,被翻译成德文并且由Ralf Steudel扩展,Berlin;NewYork:de Gruyter,1995,第557-559页。
此外,卡宾配体还可以按照下式键合于金属中心上:
条件是基团:
包含适于金属环化且与双键相邻的CH键。此外,在其中n>1的式I配合物中,一个卡宾配体可能具有如上所示与金属中心M结合的键且至少一个另外的卡宾配体可以具有如式I所示与金属中心M结合的键。
通常而言,式I的金属配合物的不同异构体可以通过本领域熟练技术人员已知的方法,例如通过色谱法、升华或结晶而提纯和/或分离。
本发明因此涉及式I的过渡金属-卡宾配合物的单个异构体以及不同异构体以任何混合比的混合物。
包含卡宾配体的过渡金属配合物在现有技术中是已知的。例如,Gründemann等,J.Am.Chem.Soc.,2002,124,10473-10481和Danapoulos等,J.Chem.Soc.,Dalton Trans.,2002,3090-3091涉及包含具有如下结构单元的卡宾配体的铱配合物:
Hitchcock等,J.Organomet.Chem.,1982,239,C 26-C 30公开了具有三个单阴离子卡宾配体且具有下列结构式的铱(III)配合物:
然而,所述文献没有一篇公开了所公开化合物的发光性能,尤其是电致发光性能,或其在OLED中的应用。
Yam等,Chem.Commun.1989,2261-2262和Yam等,J.Chem.Soc.Dalton Trans.,2001,1911-1919公开了具有卡宾配体的钌配合物。在所述文献中研究了这些卡宾配体的光物理性能,包括配合物的光致发光。然而,没有涉及这些配合物的用途也没有涉及所研究化合物的电致发光。
Che等,Organometallics 1998,17,1622-1630涉及阳离子型Re配合物,其带有具有如下结构单元的卡宾配体:
这些配合物呈现光致发光。然而,并没有公开Re配合物的应用和配合物的电致发光行为的研究。
US 6,160,267和US 6,338,977涉及取决于周围的蒸气而变色的分子发光二极管。该电极具有包含中性铂配合物的传感器-发光剂层,其中铂与两个带负电的配体配位,其中所述配体选自CN-、NO2 -、NCO-、NCS-、Cl-、Br-、I-和草酸根,且两个另外的配体选自至少一个和至多两个芳基异腈基团和具有式=C(Y)-NH-C6H4-烷基的Fischer卡宾配合物,其中Y为O-烷基、NH-烷基或N(烷基)2。US 6,160,267和US 6,338,977中所公开的Pt配合物的基本特征是存在至少一个芳基异腈基团。
上述文献均未提到本发明式I的过渡金属-卡宾配合物在OLED中的适用性,尤其是作为OLED中的发光物质的适用性,其中具有式I的这种结构的物质适合在电磁光谱的可见区中的电致发光。
因此已经发现在OLED中,尤其是在OLED中作为发光物质的本申请式I的过渡金属配合物适合生产显示器。
本发明通式I的过渡金属-卡宾配合物优选具有选自如下的金属原子M:Rh、Ir、Pd、Pt、Ru和Os,优选Rh(III)、Ir(III)、Pd(II)、Pt(II)、Ru(III)、Ru(IV)和Os(IV)。特别优选使用的金属原子是Rh、Ir、Pt和Ru,优选Rh(III)、Ir(III)、Pt(II)、Ru(III)和Ru(IV)。非常特别优选使用Ir或Pt作为金属原子M,优选Ir(III)或Pt(II),最优选Ir(III).
可以为单齿或二齿的合适单阴离子或双阴离子配体L(优选单阴离子配体L)是任何常用作单齿或二齿单阴离子或双阴离子配体的配体。
合适的单阴离子单齿配体例如为卤化物,尤其是Cl-和Br-,拟卤化物,尤其是CN-,环戊二烯基(Cp-),经由σ键键接于过渡金属M上的烷基,例如CH3,经由σ键键接于过渡金属M上的烷基芳基,例如苄基。
合适的单阴离子二齿配体例如为乙酰丙酮化物及其衍生物、甲基吡啶化物、席夫碱、氨基酸和四(1-吡唑基)硼酸盐,以及WO 02/15645中所述的二齿单阴离子配体,其中优选乙酰丙酮化物和甲基吡啶化物.
合适的不带电单齿或二齿配体已经如上所述。优选的不带电单齿配体选自PPh3、P(OPh)3、AsPh3、CO、任选取代的吡啶类、腈类及其衍生物。合适的不带电单齿或二齿配体优选为1,4-二苯基-1,3-丁二烯、1-苯基-1,3-戊二烯、2,4-己二烯、环辛烯、η4-环辛二烯和η2-环辛二烯(在每种情况下为1,3和1,5)以及还有任选取代的菲咯啉。
在按照本发明使用的式I过渡金属-卡宾配合物中,优选n至少为2,此时该卡宾配体可以相同或不同,并且优选m和q各自为0或≥1,并且配体L和K在m>1或q>1时各自可以相同或不同。变量M、L、K、Do、r、Y1-Y5和A各自如上所定义。
在按照本发明使用的式I过渡金属-卡宾配合物中,还优选n至少为2,此时该卡宾配体可以相同或不同,并且优选m和q各自为0。变量M、L、 K、Do、r、Y1-Y5和A在这里也各自如上所定义。
此外,在按照本发明使用的式I过渡金属-卡宾配合物中优选n至少为2,并且优选该卡宾配体相同且m和q各自为0。变量M、L、K、Do、r、Y1-Y5和A再次各自如上所定义。
其中例如过渡金属原子Ir(III)、Rh(III)或Ru(III)具有的配位数为6的不带电过渡金属配合物中卡宾配体的数目n为1-3,优选2或3,更优选3。当n>1时,卡宾配体可以相同或不同,优选相同。
当不存在不带电配体K时,考虑到Ir(III)、Rh(III)或Ru(III)的配位数,上述情形下单阴离子配体L的数目m相应地为4、2或0,优选2或0,更优选0。当m>1时,配体L可以相同或不同,优选相同。
其中例如过渡金属原子Pt(II)或Pd(II)具有的配位数为4的过渡金属配合物中卡宾配体的数目n为1或2,优选2。当n>1时,卡宾配体可以相同或不同,优选相同。
当不存在不带电配体K时,考虑到Pt(II)或Pd(II)的配位数,上述情形下单阴离子配体L的数目m相应地为2或0,更优选0。当m>1时,配体L可以相同或不同,优选相同。
不带电配体K的数目q取决于借助卡宾配体和配体L是否得到配位数6(例如对于Ir(III)、Rh(III)或Ru(III))或4(例如对于Pt(II)或Pd(II))。当在使用Ir(III)、Rh(III)或Ru(III)的情况下n等于3时,q的取值为0。当在使用Pt(II)或Pd(II)的情况下n等于2时,q的取值同样为0。
在本申请上下文中,术语芳基、杂芳基、烷基、链烯基和炔基各自如下所定义:
芳基为具有6-30个碳原子,优选6-18个碳原子的基本骨架的基团,其由芳族环或多个稠合的芳族环形成。合适的基本骨架例如为苯基、萘基、蒽基或菲基。该基本骨架可以未被取代(即所有可取代的碳原子带有氢原子),或可以在该基本骨架的一个、多个或所有可取代位置被取代。合适的取代基例如为烷基,优选具有1-8个碳原子的烷基,更优选甲基、乙基或异丙基,芳基,优选C6芳基,该芳基又可以被取代或未被取代,杂芳基,优选包含至少一个氮原子的杂芳基,更优选吡啶基,链烯基,优选带有一 个双键的链烯基,更优选具有一个双键和1-8个碳原子的链烯基,或具有供体或受体作用的基团。具有供体作用的基团包括具有+I和/或+M效应的基团,而具有受体作用的基团包括具有-I和/或-M效应的基团。具有供体或受体作用的合适基团是卤素基团,优选F、Cl、Br,更优选F,烷氧基,芳氧基,羰基,酯基,胺基,例如烷基胺、二烷基胺、芳基胺、二芳基胺基团或具有桥连芳基的二芳基胺基团如1-咔唑基,酰胺基团,CH2F基团,CHF2基团,CF3基团,CN基团,硫代基团或SCN基团。当芳基被取代时,它们最优选带有选自甲基、F、Cl、芳氧基和烷氧基的取代基。芳基优选为C6-C18芳基,更优选C6芳基,其任选被至少一个上述取代基取代。更优选C6-C18芳基,优选C6芳基不带、带有1个或2个上述取代基,且在一个取代基的情况下,该取代基排列在该芳基的另一键合点的邻位、间位或对位;在两个取代基团的情况下,它们可以各自排列在该芳基的另一键合点的间位或邻位,或者一个基团排列在邻位且一个基团排列在间位,或者一个基团排列在邻位或间位且另一基团排列在对位。
杂芳基指与上述芳基不同的基团,不同之处在于基本芳基骨架中至少一个碳原子已经被杂原子替换。优选的杂原子是N、O和S。最优选基本芳基骨架的一个或两个碳原子已经被杂原子替换。尤其优选该基本骨架选自诸如吡啶和诸如吡咯或呋喃的5员杂芳族的体系。该基本骨架可以在其一个、多个或所有可取代位置被取代。合适的取代基与已经在芳基定义下提到的那些相同。
烷基指具有1-20个碳原子,优选1-10个碳原子,更优选1-8个碳原子的基团。烷基可以是支化或未支化的且任选可以被一个或多个杂原子,优选Si、N、O或S,更优选N、O或S间隔。此外,烷基可以被一个或多个在芳基的定义下所述的取代基取代。烷基同样可以带有一个或多个芳基。就此而言,所有上述芳基都是合适的。更优选烷基选自甲基、乙基、正丙基、异丙基和叔丁基。
链烯基指对应于具有至少2个碳原子的上述烷基的基团,其中不同之处在于烷基的至少一个C-C单键可能的话已经被C-C双键替换。链烯基优选具有一个或两个双键。
炔基因此指对应于具有至少2个碳原子的上述烷基的基团,其中不同之处在于烷基的至少一个C-C单键可能的话已经被C-C叁键替换。炔基优选具有一个或两个叁键。
变量Y1和Y2各自独立地为氢、烷基、芳基、杂芳基或链烯基。
Y1优选为氢。Y2优选为氢或烷基,更优选氢、甲基、乙基、正丙基、异丙基或叔丁基。
在另一优选情形中,Y1和Y2与它们所键合的碳原子一起形成可以包含1或2个氮原子的6员芳族环。该环可以与另一任选稠合且任选含杂原子的环稠合。此时杂原子可以为该环的一部分或可以键合于该环上(在“外挂位置”)。
卡宾配体的对应稠合亚结构的实例如下所示:
X=CR2、C(O)、O、S、NR;R=氢、烷基、芳基
此外,例如通过苯并稠合而衍生于上述亚结构的更高度稠合的亚结构也是可能的。
卡宾配体的更高度稠合的亚结构的其他实例还有:
X=CH、N X′=CR2、C(O)、O、S、NR
(R=氢、烷基、芳基)
卡宾配体的优选亚结构为:
R=氢、烷基、芳基
此外,Y3和Y2与配位原子Do和Y2所键合的碳原子一起可以形成5或6员环,该环除了配位原子Do外还可以另外包含一个选自N、O和S的杂原子。在该环中,Y2(与Y1一起)可能已经为任选(更高度)稠合的芳族环的一部分,例如在卡宾配体的上述亚结构中,或Y2为(形式上)独立的基团,其与Y3一起形成卡宾配体的其他亚结构。
因为在上述情况下Y3基团的(形式)存在是必须的,所以唯一可能的配位原子是氮原子。在该卡宾配体中对应的亚结构实例为:
X=CR2、O、S、NR(R=氢、烷基、芳基)
优选的亚结构为:
其中X为CH2基团或氧原子。
当Y1和Y2如上所详述的那样额外形成任选更高度稠合的芳族环时,这例如导致如下所示的卡宾配体的亚结构:
X′=O、S
X=CR2、O、S、NR(R=氢、烷基、芳基)
其中符号:
表示上面所详述的苯环的可能稠合。该符号优选定义为下列片段之一:
优选的亚结构为:
其中符号:
优选如上所定义且X为CH2基团或氧原子。
式I中的变量A为具有3或4个原子的桥键,其中一个或两个原子可以为杂原子且剩余原子为碳原子,从而使以下基团(下文也称为“G”):
形成5或6员杂芳族环或苯环。可能的杂原子尤其是O、N和S。
在基团G的定义中合适的5员杂芳族环如下所示:
其中R如上所定义为氢、烷基、链烯基、炔基、芳基或杂芳基,且当R为 杂芳基时,环氮原子经由该杂芳基的碳原子或任选经由适于该目的的该杂芳族基的杂原子键合。
在基团G的定义中合适的6员杂芳族环是:
对于基团G,优选:
基团G可以被选自如下的取代基取代:烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、卤素、CN、CHO、烷基羰基、芳基羰基、羧基、烷氧羰基、芳氧羰基、羟基磺酰基、烷氧基磺酰基、芳氧基磺酰基、NO2和NO。当所述取代基包含杂原子时,它们通常经由基团G的碳原子与基团G键合。然而,该键合还可以经由基团G的合适杂原子进行。
优选的取代基团G为:
其中R″为CN、CHO、烷基羰基、芳基羰基、羧基、烷氧羰基、芳氧羰基、羟基磺酰基、烷氧基磺酰基、芳氧基磺酰基、NO2或NO,k″的取值为0或1,R和R′各自独立地为烷基或卤素,尤其是氟,以及k和k′的取值为0或1,条件是在基团(Ga)中,k和k′之和为1或2且在基团(Gb)中,当k″的取值为0时,k和k′之和为1或2,而当k″的取值为1时,k和k″ 之和为0、1或2。在k″的取值为0时,k和k′之和优选为2;在k″的取值为1时,k和k″之和优选为0或2。对k、k′或k″而言,取值为0在本文中是指在该环的对应位置上不存在R、R′或R″取代基且因此存在的是氢原子。当k和k′各自取值为1时,取代基优选相同。
对于R和R′,烷基尤其为甲基、乙基、正丙基、异丙基和叔丁基。存在于R″的定义的对应基团中的烷基和芳基分别尤其为甲基、乙基、正丙基、异丙基和叔丁基以及苯基、萘基、蒽基或菲基,它们各自可以被选自甲基、F、Cl、苯氧基、甲氧基、乙氧基、正丙氧基、异丙氧基和叔丁氧基的取代基取代,并且优选任选取代的苯基。
该类取代的基团尤其包括:
此外,基团G还可以与另一任选含杂原子的环稠合,此时后一环本身可以再次稠合。
该类更高度稠合的基团G的实例是:
其中X为O、S或NR,其中R为氢、烷基或芳基,且两个X′各自独立地为羰基、CR2基团、O、S或NR,其中R为氢、烷基或芳基。
优选的稠合基团G为:
其中X的定义为O、S或NR,其中R为氢、烷基或芳基,优选氢或烷基。
此外,Y1与选自化学单键、C(Y4)2、C(O)、O、S、S(O)、SO2和NY5的基团一起可以形成2员桥键B,该桥键B连接于桥键A中的碳原子或杂原子,其中所述桥键A中的碳原子或杂原子位于与卡宾配体的卡宾单元的氮原子键合的碳原子的α位。Y4和Y5各自独立地为各自如上所定义的烷基、芳基或杂芳基,或氢。桥键C(Y4)2中的两个Y4可以相互独立地变化,但优选它们相同。更优选两个R4基团为两个氢原子或两个甲基。
形式上讲,该类亚结构可以如下所示:
其中星号表示位于桥键A中的N键合的乙烯碳原子的α位上的碳原子或合适的杂原子,且B表示由Y1和化学单键、C(Y4)2、C(O)、O、S、S(O)、SO2或NY5组成的桥键。
该类亚结构的实例为:
在式(Ba)和(Bb)中,桥键B在每种情况下由亚乙烯基单元组成,而在式(Bc)和(Bd)中,桥键B在每种情况下由-CH2-X-单元组成,其中X的定义为C(Y4)2、C(O)、O、S、S(O)、SO2或NY5。
当Y1和Y2额外形成任选稠合的芳族环,例如苯环时,这例如导致如下所示的亚结构:
其中桥键B在某些情况下为苯环的一部分。X又为化学单键、C(Y4)2、C(O)、O、S、S(O)、SO2或NY5,且符号:
如前所述为苯环的稠合。
这里还优选该符号具有如下片段的定义:
R=氢、烷基、芳基
优选的亚结构为:
其中X尤其为O、S、C(CH3)2或SO2基团。
在本发明上下文中,还要求保护通式I的不带电过渡金属-卡宾配合物:
其中各变量如下所定义:
M为选自Co、Rh、Ir、Nb、Pd、Pt、Fe、Ru、Os、Cr、Mo、W、Mn、Re、Cu、Ag和Au的金属原子,对于特定金属原子呈任何可能的氧化态;
L为可以是单齿或二齿的单阴离子或双阴离子配体;
K为选自如下的不带电单齿或二齿配体:膦;膦酸酯及其衍生物,砷酸酯及其衍生物;亚磷酸酯;CO;吡啶类;腈类,与M形成π-配合物的单烯烃和共轭二烯;
n为卡宾配体数目,其中n至少为1且式I配合物中的卡宾配体在n>1时可以相同或不同;
m为配体L的数目,其中m可以为0或≥1且配体L在m>1时可以相同或不同;
q为配体K的数目,其中q可以为0或≥1且配体K在q>1时可以相同或不同;
其中n+m+q之和取决于所用金属原子的氧化态和配位数以及配体的齿数和电荷,条件是n至少为1;
Do为选自N、O和S的配位原子;
r在Do为N时为1且在Do为O或S时为0;
Y1、Y2各自独立地为氢、烷基、链烯基、炔基、芳基或杂芳基;
或
Y1和Y2与它们所键合的碳原子一起形成可以包含1个或2个氮原子并且任选稠合于另一环的6员芳族环,其中所述另一环任选稠合并且任选包含杂原子;
Y3为氢或烷基;
或
Y3和Y2与配位原子Do和键于Y2的碳原子一起形成5或6员环,该环除了配位原子Do外还可以另外包含选自N、O和S的杂原子;
A为具有3或4个原子的桥键,其中一个或两个原子可以为杂原子且剩余原子为碳原子,从而使如下基团
形成5或6员杂芳族环或苯环,所述环各自任选被选自如下的取代基取代:烷基、烷氧基、烷硫基、芳基、芳氧基、芳硫基、卤素、CN、CHO、烷基羰基、芳基羰基、羧基、烷氧羰基、芳氧羰基、羟基磺酰基、烷氧基磺酰基、芳氧基磺酰基、NO2和NO,并任选与另一任选稠合且任选包含杂原子的环稠合,
其中Y1与选自化学单键、C(Y4)2、C(O)、O、S、S(O)、SO2和NY5的基团一起可以任选形成2员桥键B,该桥键B连接于桥键A中位于与卡宾配体的卡宾单元的氮原子键合的碳原子的α位的碳原子或杂原子;
Y4、Y5各自独立地为氢、烷基、芳基或杂芳基,且C(Y4)2桥键中的两个Y4基团可以相互独立地变化。
对于在OLED中的应用,该配合物的优选结构特征和各变量的优选定义还适用于按照本发明所要求保护的配合物。
优选的本发明式I的配合物包含一个或多个通过将选自如下的亚结构:
Y1、Y2=氢、烷基 X=O,S
R=氢、烷基、芳基
与选自如下的亚结构结合而得到的卡宾配体:
X=O、S、NR;R=氢或烷基
其中配位原子Do优选为S或N-Y3,以及Y3优选为甲基、乙基、正丙基、异丙基或叔丁基。
特别优选的本发明式I的配合物包含一个或多个通过将选自如下的亚结构:
Y1、Y2=氢、烷基
与选自如下的亚结构结合而得到的卡宾配体:
其中配位原子Do优选为S或N-Y3且Y3优选为甲基、乙基、正丙基、异丙基或叔丁基。
对于该组合尤其应提到仅具有卡宾配体的下列配合物:
其中M为Ru(III)、Rh(III)、Ir(III)、Pd(II)或Pt(II),n对Ru(III)、Rh(III)和Ir(III)时为3且对Pd(II)和Pt(II)时为2,以及Y2和Y3各自为氢、甲基、乙基、正丙基、异丙基或叔丁基。M优选为Ir(III),其中n=3。Y3优选为甲基、乙基、正丙基、异丙基或叔丁基。示出上面所列的某些异构化合物以说明开头对式I的卡宾配合物的异构化所作的解释。
其他特别优选的本发明式I的配合物包含一个或多个通过将选自如下的亚结构:
与选自如下的亚结构结合而得到的卡宾配体:
其中配位原子Do优选为S或N-Y3且Y3优选为甲基、乙基、正丙基、异丙基或叔丁基。
对于该组合尤其应提到仅具有卡宾配体的下列配合物:
其中M为Ru(III)、Rh(III)、Ir(III)、Pd(II)或Pt(II),n对Ru(III)、Rh(III)和Ir(III)时为3且对Pd(II)和Pt(II)时为2,以及Y3为氢、甲基、乙基、正丙基、异丙基或叔丁基。M优选为Ir(III)其中n=3。Y3优选为甲基、乙基、正丙基、异丙基或叔丁基。
其他特别优选的本发明式I的配合物包含一个或多个含有选自如下的亚结构的卡宾配体:
其中Do的定义为S或N-Y3且Y的定义为O、S、C(CH3)2或SO2,Y2的定义为氢、甲基、乙基、正丙基、异丙基或叔丁基,以及Y3的定义为甲基、乙基、正丙基、异丙基或叔丁基。
尤其应提到的对应配合物是:
其中M为Ru(III)、Rh(III)、Ir(III)、Pd(II)或Pt(II),n对Ru(III)、Rh(III)和Ir(III)时为3且对Pd(II)和Pt(II)时为2,Y的定义为O、S、C(CH3)2 或SO2,Do的定义为S或N-Y3,Y2的定义为氢、甲基、乙基、正丙基、异丙基或叔丁基,且Y3的定义为甲基、乙基、正丙基、异丙基或叔丁基。M优选为Ir(III),其中n=3。
应提到的实例是:
其中M为Ru(III)、Rh(III)和尤其是Ir(III)、Pd(II)或Pt(II),n对Ru(III)、Rh(III)和Ir(III)时为3且对Pd(II)和Pt(II)时为2。
其他优选的本发明式I的配合物包含一个或多个通过将选自如下的亚结构:
(其中X为CH2基团或氧原子且Y1为氢、甲基、乙基、异丙基或叔丁基)与选自如下的亚结构结合而得到的卡宾配体:
对于该组合尤其应提到仅具有卡宾配体的下列配合物:
其中M为Ru(III)、Rh(III)以及尤其是Ir(III)、Pd(II)或Pt(II),n的取值对Ru(III)、Rh(III)和Ir(III)时为3且对Pd(II)和Pt(II)时为2。
尽管在前面的评述中已直接涉及具有相同卡宾配体的配合物,这里应注意的是具有不同卡宾配体和/或具有配体L和/或K(对应的配体L和K已经在开头定义)的配合物当然也可以按照本发明使用。
参照下表,示意性地说明具有三价金属中心和两个不同的卡宾配体L′和L″的配合物ML′(L″)2:
L′ | L″ | L′ | L″ | L′ | L″ | L′ | L″ |
L1 | L2 | L3 | L4 | L7 | L5 | L5 | L3 |
L1 | L3 | L3 | L5 | L7 | L4 | L5 | L2 |
L1 | L4 | L3 | L6 | L7 | L3 | L5 | L1 |
L1 | L5 | L3 | L7 | L7 | L2 | L4 | L3 |
L1 | L6 | L4 | L5 | L7 | L1 | L4 | L2 |
L1 | L7 | L4 | L6 | L6 | L5 | L4 | L1 |
L2 | L3 | L4 | L7 | L6 | L4 | L3 | L2 |
L2 | L4 | L5 | L6 | L6 | L3 | L3 | L1 |
L2 | L5 | L5 | L7 | L6 | L2 | L2 | L1 |
L2 | L6 | L6 | L7 | L6 | L1 | ||
L2 | L7 | L7 | L6 | L5 | L4 |
其中M例如为Ru(III)、Rh(III)或Ir(III),尤其是Ir(III),且L′和L″例如为选自配体L1-L7的配体:
Y2为氢、甲基、乙基、正丙基、异丙基或叔丁基,以及Y3为甲基、乙基、正丙基、异丙基或叔丁基。
具有不同卡宾配体(L′=L4,其中Y2=氢且Y3=甲基;L″=L2,其中Y2=氢且Y3=甲基)的这些配合物的一个代表例如为:
应理解的是按照本发明使用的三价金属中心(例如在Ru(III)、Rh(III)或Ir(III)的情况下)的配合物中的所有三个卡宾配体也可以相互不同。
具有配体L(这里为单阴离子二齿配体)作为“旁观者配体(spectatorligand)”的三价金属中心M的配合物的实例是LML′L″、LM(L′)2和L2ML′,其中M例如为Ru(III)、Rh(III)或Ir(III),尤其是Ir(III),以及L′和L″各自如上所定义。对于配合物LML′L″中L′和L″的组合,得到如下结果:
L′ | L″ | L′ | L″ |
L1 | L2 | L3 | L4 |
L1 | L3 | L3 | L5 |
L1 | L4 | L3 | L6 |
L1 | L5 | L3 | L7 |
L1 | L6 | L4 | L5 |
L1 | L7 | L4 | L6 |
L2 | L3 | L4 | L7 |
L2 | L4 | L5 | L6 |
L2 | L5 | L5 | L7 |
L2 | L6 | L6 | L7 |
L2 | L7 |
可能的配体L尤其为乙酰丙酮化物及其衍生物,甲基吡啶化物,席夫碱,氨基酸,四(1-吡唑基)硼酸盐以及WO 02/15645中所述的二齿单阴离子配体;乙酰丙酮化物和甲基吡啶化物尤其令人感兴趣。在配合物L2ML′的情况下,配体L可以相同或不同。
具有不同卡宾配体(L′=L4,其中Y2=氢且Y3=甲基;L″=L2,其中Y2=氢且Y3=甲基)的这些配合物的一个代表例如为:
其中在如下符号中的z1和z2:
表示配体L的两个“齿”。Y3为氢、甲基、乙基、正丙基、异丙基或叔丁基,尤其是甲基、乙基、正丙基或异丙基。
上述不带电的过渡金属配合物特别适合作为有机发光二极管(OLED)中的发光剂分子。配体或中心金属的简单改变可以提供在电磁光谱的红色、绿色且尤其是蓝色区域中呈现电致发光的过渡金属配合物。按照本发明使用的不带电过渡金属配合物因此适合用于工业上可用的全色显示器。
此外,上述不带电的过渡金属配合物适合作为OLED中的电子、激子或空穴阻挡剂,这取决于所用配体和所用中心金属。
本发明式I的过渡金属-卡宾配合物可以类似于本领域熟练技术人员已知的方法制备。合适的制备方法例如详述于综述文章W.A.Hermann等,Advances in Organometallic Chemistry,第48卷,第1-69页,W.A.Hermann等,Angew.Chem.1997,109,第2256-2282页和G.Bertrand等,Chem.Rev.2000,100,第39-91页以及其中所引用的文献中。
本申请进一步提供了一种制备式I的卡宾配合物的方法。
在本发明方法中,本发明式I的过渡金属配合物通过使对应于特定卡宾配体的配体前体脱去质子并随后或同时与包含所需金属的合适金属配合物反应而制备。
此外,可以通过直接使用Wanzlick烯烃而制备本发明的过渡金属配合物。
合适的配体前体对本领域熟练技术人员是已知的。它们优选为具有带负电的抗衡离子的阳离子前体。
在一个实施方案中,使阳离子前体与碱反应并且形成的中间体可能取决于该前体而不同。取决于该反应,例如形成烷氧基化物衍生物、二聚Wanzlick烯烃或游离N-杂环卡宾。烷氧基化物衍生物和Wanzlick烯烃通常在合适的金属前体存在下热激发,以消除醇或使二聚体裂解,并且在合适的金属配合物存在下形成金属-卡宾化合物。这些反应通常在本领域熟练技术人员已知或者可以通过简单的初步试验确定的合适溶剂中进行,并且在两步方案的情况下对于两个步骤可以使用相同的溶剂或不同的溶剂。可供选择的可能溶剂例如为芳族和脂族溶剂或醚类,如甲苯、四氢呋喃,此外还有醇类或氯代烃类如二氯甲烷,液氨,合适的话与四氢呋喃混合,以及极性非质子溶剂,如二甲基甲酰胺、N-甲基吡咯烷酮或乙腈。通常仅在反应中不形成游离卡宾时使用醇和卤代烃。
用于与配体前体反应的碱可以存在于包含式I的配合物的所需金属M的金属化合物中。可能的金属化合物是金属乙酸盐,金属乙酰丙酮化物,金属氨化物或金属醇盐。此外,该反应可以使用外部碱如KOtBu、NaOtBu、LiOtBu、NaH、二硅烷基氨化物和磷腈碱进行。还可以使用包含碱的金属化合物与外部碱结合而进行与配体前体的反应。
本发明通式I的过渡金属-卡宾配合物优选由相应的阳离子前体开始通过与外部碱,优选KOtBu或二硅烷基氨化物,尤其是例如二(三甲基甲硅烷基)氨化钾反应并使所得中间体随后或原位地与所需金属的配合物反应而得到,其中所述阳离子前体选自唑鎓(azolium)盐,尤其是咪唑鎓盐,苯并咪唑鎓盐;三唑鎓盐和唑烷鎓(azolidinium)盐,尤其是咪唑烷鎓盐。
所需金属的合适配合物对本领域熟练技术人员而言是已知的。在所用 金属配合物中的所需金属和由其制备的过渡金属-卡宾配合物I的对应金属不必具有相同的氧化态。
在根据本申请特别优选的通式I的铱(III)配合物的制备中,例如可以使用下列铱(III)配合物:[(μ-Cl)Ir(η4-1,5-cod)]2,[(μ-Cl)Ir(η2-1,5-coe)2]2,Ir(acac)3,IrCl3·n H2O,(tht)3IrCl3,其中cod为环辛二烯,coe为环辛烯,acac为乙酰丙酮化物且tht为四氢噻吩。
醇盐衍生物或Wanzlick烯烃通常在室温下加入合适的金属前体中并随后热激发,在此过程中在醇盐衍生物的情况下消除对应的醇,或裂解二聚的Wanzlick烯烃,并且形成金属-卡宾化合物。通常而言,这些反应在20-160℃的温度下进行。当所用中间体是游离卡宾(例如咪唑啉-2-亚基)时,它们通常在冷却下加入金属前体中,然后温热至室温(20-25℃)和/或合适的话甚至温热至更高的温度。通常而言,该反应在-78℃至+160℃的温度范围内进行。
所用金属配合物与所用配体前体的比例取决于带有至少两个卡宾配体的所需配合物。当金属原子为特别优选的Ir(III)且所需过渡金属配合物包含三个同样特别优选的卡宾配体时,配体前体的摩尔量必须大到约金属配合物中的金属摩尔量的三倍,并且可以使用稍微过量的配体前体。金属配合物中金属与配体前体摩尔量的摩尔比通常为1∶3-1∶6。
所用碱与所用配体前体的摩尔比通常为3∶1-1∶1,优选2∶1-1∶1。当使用强碱如LiOtBu、NaOtBu、KOtBu或双(三甲基甲硅烷基)氨化钾(KHMDS)时,碱与配体前体的摩尔比为1∶1通常是足够的。
两种本发明的具有N-杂环卡宾配体的铱配合物的制备例举如下:
咪唑啉亚基配合物:
X-为阴离子基团,优选卤离子基团、拟卤离子基团或另一单阴离子基团,例如Cl-、Br-、I-、BF4 -、PF6 -、CN-、SCN-,更优选BF4 -、PF6 -。
苯并咪唑啉亚基配合物:
X-已经如上所定义。
按照本发明使用的过渡金属-卡宾配合物尤其适合作为发光剂物质,因为它们在电磁光谱的可见区发光(电致发光)。借助按照本发明使用的作为发光剂物质的过渡金属-卡宾配合物,可以提供在电磁光谱的红色、绿色和蓝色区域具有电致发光的化合物。因此可以借助按照本发明作为发光剂物质使用的过渡金属-卡宾配合物来提供工业上可用的全色显示器。
不同取代的卡宾配体及不同过渡金属的可得性可以制备在电磁光谱的不同区域发光的发光剂物质。对于这些物质而言,量子产率高且过渡金属-卡宾配合物,尤其是具有N-杂环卡宾配体的那些在器件中具有高稳定性。
此外,上述不带电的过渡金属配合物适合在OLED中作为电子、激子或空穴阻挡剂,这取决于所用配体和所用中心金属。
有机发光二极管原则上由几层组成:
1.阳极
2.空穴传输层
3.发光层
4.电子传输层
5.阴极
然而,OLED还可以不具有所有所述层;例如具有层(1)(阳极)、(3)(发 光层)和(5)(阴极)的OLED同样是合适的,此时层(2)(空穴传输层)和(4)(电子传输层)的功能由相邻层承担。具有层(1)、(2)、(3)和(5)或层(1)、(3)、(4)和(5)的OLED同样是合适的。
根据本申请的过渡金属-卡宾配合物可以用于OLED的各层中。本发明因此进一步提供了包含至少一种本申请的过渡金属-卡宾配合物的OLED。该过渡金属-卡宾配合物优选在发光层中用作发光剂分子。本发明因此进一步提供了包含至少一种过渡金属-卡宾配合物作为发光剂分子的发光层。优选的过渡金属-卡宾配合物,尤其是具有N-杂环卡宾配体的过渡金属-卡宾配合物如上所述。
本发明的过渡金属-卡宾配合物,或者按照本发明使用的那些可以直接,即没有其他添加剂,存在于OLED的发光层或另一层中,优选存在于发光层中。然而,同样可能的是除了按照本发明使用的过渡金属-卡宾配合物外,其他化合物可以存在于包含至少一种本申请的过渡金属-卡宾配合物的层中,优选存在于发光层中。例如,发光层中可以存在荧光染料以改变用作发光剂分子的过渡金属-卡宾配合物的发光颜色。此外,可以使用稀释剂材料。该稀释剂材料可以是聚合物,例如聚(N-乙烯基咔唑)或聚硅烷。然而,稀释剂材料同样可以是小分子,例如4,4’-N,N’-二咔唑基联苯(CDP=CBP)或叔芳族胺。若使用稀释剂材料,则按照本发明使用的过渡金属-卡宾配合物在发光层中的比例通常低于60重量%,优选低于50重量%,更优选为5-40重量%。
OLED的上述各层可以由两层或更多层组成。例如,空穴传输层可以由将空穴从电极注入其中的层和将空穴从空穴注入层传输到发光层的层组成。电子传输层同样可以由多层组成,例如由通过电极将电子注入其中的层和从电子注入层接收电子并将它们传输到发光层中的层组成。这些特定层各自根据诸如能级、耐热性和电荷载体迁移性的因素以及所述层与有机层或金属电极之间的能量差选择。本领域熟练技术人员能够选择OLED的结构以使其最佳地与根据本发明用作发光剂物质的过渡金属-卡宾配合物匹配。
为了得到特别有效的OLED,应使空穴传输层的HOMO(最高被占分 子轨道)与阳极的功函匹配并使电子传输层的LUMO(最低未占分子轨道)与阴极的功函匹配。
本申请还提供了一种包含至少一种本发明的发光层的OLED。该OLED中的其他层可以由任何常用于该类层中且为本领域熟练技术人员已知的材料组成。
阳极(1)是提供正电荷载体的电极。它例如可以由包含金属、不同金属的混合物、金属合金、金属氧化物或不同金属氧化物的混合物的材料制成。或者,阳极可以是导电聚合物。合适的金属包括元素周期表第11、4、5和6族金属以及第8-10族过渡金属。当阳极要透明时,则通常使用元素周期表第12、13和14族的混合金属氧化物,例如铟-锡氧化物(ITO)。阳极(1)同样可以包含有机材料,如聚苯胺,例如如Nature,第357卷,第477-479页(1992年6月11日)所述。阳极或阴极中的至少一种应至少部分透明以使所产生的光能被辐射。
用于本发明OLED的层(2)的合适空穴传输材料例如公开于Kirk-Othmer Encyclopedia of Chemical Technology,第4版,第18卷,第837-860页,1996中。空穴传输分子或聚合物可以用作空穴传输材料。通常使用的空穴传输分子选自4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)、N,N’-二苯基-N,N’-双(3-甲基苯基)[1,1’-联苯基]-4,4’-二胺(TPD)、1,1-双[(二-4-甲苯基氨基)苯基]环己烷(TAPC)、N,N’-双(4-甲基苯基)-N,N’-双(4-乙基苯基)-[1,1’-(3,3’-二甲基)联苯基]-4,4’-二胺(ETPD)、四(3-甲基苯基)-N,N,N’,N’-2,5-苯二胺(PDA)、α-苯基-4-N,N-二苯基氨基苯乙烯(TPS)、对-(二乙氨基)苯甲醛二苯基腙(DEH)、三苯基胺(TPA)、双[4-(N,N-二乙氨基)-2-甲基苯基](4-甲基苯基)甲烷(MPMP)、1-苯基-3-[对-(二乙氨基)苯乙烯基]-5-[对-(二乙氨基)苯基]吡唑啉(PPR或DEASP)、1,2-反式-双(9H-咔唑-9-基)环丁烷(DCZB)、N,N,N’,N’-四(4-甲基苯基)-(1,1’-联苯基)-4,4’-二胺(TTB)、4’,4’,4”-三(N,N-二苯基氨基)三苯基胺(TDTA)和卟啉化合物,以及酞菁如酞菁铜。常用的空穴传输聚合物选自聚乙烯基咔唑、(苯基甲基)聚硅氧烷,PEDoT(聚(3,4-亚乙二氧基噻吩)),优选掺杂有PSS(聚苯乙烯磺酸盐)的PEDoT,以及聚苯胺。同样可以通过将空穴传输分子掺杂到聚合物 如聚苯乙烯和聚碳酸酯中而得到空穴传输聚合物。合适的空穴传输分子是上述分子。
用于本发明OLED的层(4)的合适电子传输材料包括与oxynoid化合物如三(8-羟基喹啉根合)铝(Alq3)、基于菲咯啉的化合物如2,9-二甲基-4,7-二苯基-1,10-菲咯啉(DDPA=BCP)或4,7-二苯基-1,10-菲咯啉(DPA)以及唑类化合物如2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑(PBD)和3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1,2,4-三唑(TAZ)螯合的金属。层(4)可以同时用于促进电子传输和用作缓冲层或阻挡层以防止激子在OLED各层的界面处的猝灭。该层(4)优选改进电子的迁移性并降低的猝灭。
在上述作为空穴传输材料和电子传输材料的材料中,某些可以满足多种功能。例如,导电材料中的一些在具有低位HOMO时同时为空穴阻挡材料。
还可以将电荷传输层进行电子掺杂以改善所用材料的传输性能,首先使层厚更大(避免针孔/短路),其次使器件的操作电压降至最小。例如,空穴传输材料可以掺杂电子受体;例如,酞菁或芳基胺如TPD或TDTA可以掺杂有四氟四氰基醌二甲烷(F4-TCNQ)。电子传输材料例如可以掺杂碱金属,例如用锂掺杂Alq3。电子掺杂对本领域熟练技术人员是已知的且例如公开于W.Gao,A.Kahn,J.Appl.Phys.,第94卷,第1期,2003年7月1日(p-掺杂的有机层);A.G.Werner,F.Li,K.Harada,M.Pfeiffer,T.Fritz,K.Leo,Appl.Phys.Lett.,第82卷,第25期,2003年6月23日和Pfeiffer等,Organic Electronics 2003,4,89-103。
阴极(5)是用于引入电子或负电荷载体的电极。合适的阴极材料选自元素周期表第1族碱金属,如Li、Cs,第2族碱土金属,例如钙、钡或镁,第12族金属,其包括镧系和锕系金属,例如钐。此外,还可以使用诸如铝或铟的金属以及所有所述金属的组合。此外,还可以在有机层和阴极之间施加含锂的有机金属化合物或LiF以降低操作电压。
本发明的OLED可以额外包含本领域熟练技术人员已知的其他层。例如,可以在层(2)和发光层(3)之间施加促进传输正电荷和/或使各层的带隙相互匹配的层。或者,该其他层可以用作保护层。以类似方式可以在发光 层(3)和层(4)之间存在额外层,以促进传输负电荷和/或使各层的带隙相互匹配。或者,该层可以用作保护层。
在优选实施方案中,本发明的OLED除了层(1)-(5)外还包含至少一个下述其他层:
-在阳极(1)和空穴传输层(2)之间的空穴注入层;
-在空穴传输层(2)和发光层(3)之间的电子和/或激子阻挡层;
-在发光层(3)和电子传输层(4)之间的空穴和/或激子阻挡层;
-在电子传输层(4)和阴极(5)之间的电子注入层。
然而,还可能的是OLED不具有所有的所述层(1)-(5);例如,具有层(1)(阳极)、(3)(发光层)和(5)(阴极)的OLED同样是合适的,此时层(2)(空穴传输层)和(4)(电子传输层)的功能由相邻层承担。具有层(1)、(2)、(3)和(5)或层(1)、(3)、(4)和(5)的OLED同样是合适的。
本领域熟练技术人员知道如何选择合适的材料(例如基于电化学研究)。用于各层的合适材料对本领域熟练技术人员是已知的且例如公开于WO 00/70655中。
此外,本发明OLED的上述各层可以由两层或更多层组成。此外,层(1)、(2)、(3)、(4)和(5)中的一些或所有可以进行表面处理以增加电荷载体的传输效率。所述各层的材料选择优选应通过得到具有高效率和长运行时间的OLED而确定。
本发明的OLED可以通过本领域熟练技术人员已知的方法生产。通常通过在合适的基材上依次气相沉积各层而生产OLED。合适的基材例如包括玻璃或聚合物膜。对于气相沉积,可以使用常规技术如热蒸发、化学气相沉积和其他技术。在替换方法中,可以由在合适溶剂中的溶液或分散体而施涂有机层,此时使用本领域熟练技术人员已知的涂敷技术。在OLED的各层之一,优选发光层中通常将除了至少一种本发明的过渡金属-卡宾配合物外还具有聚合材料的组合物借助溶液调节方法作为层施用。
通常而言,不同层具有如下厚度:阳极(1) 优选 空穴传输层(2) 优选 发光层(3) 优选 电子传输层(4) 优选 阴 极(5) 优选 在本发明的OLED中空穴和电子的复合区的位置以及因此OLED的发光光谱可能受各层的相对厚度的影响。这意味着电子传输层的厚度的选择优选应使电子/空穴复合区位于发光层中。OLED中各层的层厚之比取决于所用材料。任何所用额外层的层厚对本领域熟练技术人员是已知的。
根据本发明使用的过渡金属-卡宾配合物在OLED的至少一层中的使用,优选在本发明OLED的发光层中作为发光剂分子的使用使得可以得到具有高效率的OLED。此外,本发明OLED的效率可以通过优化其他层而得以额外改进。例如,可以使用高效的阴极如Ca或Ba,合适的话与LiF的中间层组合。同样可以在本发明OLED中使用降低操作电压或增加量子效率的成型基材和新型空穴传输材料。此外,在OLED中可以存在额外层以调节不同层的能级并促进电致发光。
本发明的OLED可以用于所有使用电致发光的器件中。合适的器件优选选自固定和移动可视显示单元(VDU)。固定VDU例如为计算机、电视的VDU,打印机、厨房用具和广告张贴板、照明和信息板中的VDU。移动VDU例如为移动电话、便携式电脑、数字照相机、车辆以及公共汽车和火车中的目的地显示中的VDU。
此外,根据本发明使用的过渡金属-卡宾配合物可以用于具有反转结构的OLED中。在这些反转OLED中,这些反转OLED中的过渡金属-卡宾配合物再次优选用于发光层中。反转OLED的结构和常用于其中的材料对本领域熟练技术人员是已知的。
上述本发明的过渡金属配合物或按照本发明使用的那些除了用于OLED中外还可以用作着色剂,其在光辐照时在电磁光谱的可见区发光(光致发光)。该类着色剂优选在聚合材料中用作着色剂。
本申请因此进一步提供了上述本发明的过渡金属-卡宾配合物或按照本发明使用的那些在聚合物材料整体着色中的用途。
合适的聚合物材料是聚氯乙烯、乙酸纤维素、聚碳酸酯、聚酰胺、聚氨酯、聚酰亚胺、聚苯并咪唑、蜜胺树脂、聚硅氧烷、聚酯、聚醚、聚苯乙烯、聚甲基丙烯酸甲酯、聚乙烯、聚丙烯、聚乙酸乙烯酯、聚丙烯腈、 聚丁二烯、聚氯丁二烯、聚异戊二烯以及所列单体的共聚物。
此外,上述本发明过渡金属配合物或按照本发明使用的那些可以用于下列应用中:
●该过渡金属配合物作为翁染料或在翁染料中的用途,例如用于对天然材料着色;实例是纸张、木材、稻草、皮革、毛皮或天然纤维材料如棉花、羊毛、丝、黄麻、剑麻、大麻、亚麻或动物毛发(例如马毛)及其转化产品如粘胶纤维、硝化丝或铜氨螺萦。
●该过渡金属配合物作为着色剂的用途,例如用于对油漆、清漆和其他表面涂料组合物、纸张油墨、印刷油墨、其他油墨以及用于绘画和书写目的的着色剂的着色。
●该过渡金属配合物作为颜料的用途,例如用于对油漆、清漆和其他表面涂料组合物、纸张着色剂、印刷油墨、用于绘画和书写目的的油墨和其他着色剂的着色。
●该过渡金属配合物在静电复印中作为颜料的用途:例如用于干式复印系统(Xerox方法)和激光打印机。
●该过渡金属配合物在安全标记目的中的用途,对该目的而言物质的高化学和光化学稳定性以及合适的话还有发光性是重要的。这优选用于检查、检查卡片、支票、联票、文件、识别纸等,其中必需实现特殊的不会弄错的颜色印记。例如还可以用于对抗商标剽窃。
●该过渡金属配合物作为其他着色剂的添加剂的用途,其中需要实现特殊色调;优选特别亮的着色剂。
●该过渡金属配合物在使用发光的标记制品在机器识别这些制品中的用途,优选机器识别用于分类的制品,包括例如用于塑料再循环的制品。
●该过渡金属配合物作为机器可读标记的发光染料的用途;优选字母数字标记或条形码。
●该过渡金属配合物在调节光频率中的用途,例如将短波长光转化成更长波长的可见光。
●该过渡金属配合物在任何种类的显示、信息和标记目的的显示元件中的用途,例如用于无源显示元件、信息信号和交通信号如交通灯。
●该过渡金属配合物在喷墨打印机中的用途,优选作为发光油墨用于均相溶液中。
●该过渡金属配合物作为超导有机材料的原料的用途。
●该过渡金属配合物在固态发光标记中的用途。
●该过渡金属配合物在装饰性目的中的用途。
●该过渡金属配合物在示踪剂目的中的用途,例如用于生物化学、药物、工程和自然科学中。在该用途中,染料可以共价键合于基材上或经由次级价键如氢键或疏水性相互作用(吸附)而键合。
●该过渡金属配合物在闪烁器件中作为发光染料的用途。
●该过渡金属配合物在光学光聚集系统中作为染料或发光染料的用途。
●该过渡金属配合物在发光太阳能聚光器中作为染料或发光染料的用途(参见Langhals,Nachr.Chem.Tech.Lab.28(1980)716)。
●该过渡金属配合物在发光活化的显示中作为染料或发光染料的用途(参见W.Greubel和G.Baur,Elektronik 26(1977)6)。
●该过渡金属配合物在用于光诱导聚合以生产塑料的冷光源中作为染料或发光染料的用途。
●该过渡金属配合物作为材料测试用染料或发光染料的用途,例如在半导体电路的生产中。
●该过渡金属配合物作为集成半导体组件的微结构研究用染料或发光染料的用途。
●该过渡金属配合物在光电导体中作为染料或发光染料的用途。
●该过渡金属配合物在照相工艺中作为染料或发光染料的用途。
●该过渡金属配合物在显示、照明或图象转换系统中作为染料或发光染料的用途,其中借助电子、离子或UV辐射激发,例如在发光显示器、Braun管或荧光管中。
●该过渡金属配合物作为染料或发光染料用作集成半导体电路的一部分 的用途,其中染料直接使用或与其他半导体结合使用,例如以外延形式。
●该过渡金属配合物在化学发光系统中作为染料或发光染料的用途,例如在化学发光照明棒、发光免疫分析或其他发光检测方法中。
●该过渡金属配合物作为染料或发光染料用作信号着色剂的用途,优选用于题词和图画或其他图形产品的光学强调,用于个性化信号和其中需要实现特殊光学颜色印记的其他制品。
●该过渡金属配合物在染料激光中作为染料或发光染料的用途,优选作为产生激光光束的发光染料。
●该过渡金属配合物作为非线性镜片的有源物质的用途,例如用于激光的频率倍增和频率三倍增。
●该过渡金属配合物作为流变改进剂的用途。
●该过渡金属配合物在将电磁辐射转化成电能的光伏应用中作为染料的用途。
下列实施例对本发明提供额外说明。
实施例:
除非另有说明,下文中的百分数总是为重量%。
实施例1:制备过渡金属-卡宾配合物
制备卡宾前体化合物
a)
在氮气保护下,首先将1500ml干二甲基甲酰胺(DMF)加入1000ml四颈烧瓶中并加入72.67g(0.6mol)4-氟氰基苯和61.2g(0.9mol)咪唑,最后加 入21.6g(0.9mol)氢化钠。将反应混合物加热到100℃,在该温度下搅拌4小时,最后在室温下搅拌过夜。然后将反应混合物倾入水上并将所得混合物用二氯甲烷重复萃取。将有机相干燥,在旋转蒸发器上浓缩并最后在60℃和减压下干燥。产量为94g(对应于理论值的93%)。
1H NMR(400MHz,CDCl3):δ=7.27(s,1H);7.35(s,1H);7.54(d,J=8.8Hz,2H);7.81(d,J=8.8Hz,2H);7.95(s,1H)。
b)
在带有冷凝器的2000ml单颈烧瓶中将56g(0.33mol)由a)得到的4-N-咪唑基苄腈溶于560ml无水四氢呋喃中,与234.2g(1.65mol)碘甲烷混合,简单搅拌并在不进一步搅拌下放置48小时。然后用乙醇将固体烧瓶内容物淤浆化,吸滤并用乙醇洗涤至流出液基本无色。将残余物在70℃和减压下干燥。产量为81.54g(对应于理论值的79.7%)。
1H NMR(400MHz,DMSO):δ=3.97(s,3H);8.00-8.04(m,3H);8.22(d,J=9.0Hz,2H);8.40(dd,J=1.8,1.8Hz,1H);9.91(s,1H)。
元素分析(对经验式C11H10IN3的计算值):
计算值(重量%) 实测值(重量%)
碘 40 40.9
碳 42.4 42.6
氮 13.5 13.6
氢 3.3 2.93
c)
首先向500升三颈烧瓶中加入10g(32mmol)在150ml甲苯中的碘化咪唑鎓并在室温下在30分钟内加入64.3ml双(三甲基甲硅烷基)氨化钾(0.5M,在甲苯中,32mmol)。将该混合物在室温下搅拌30分钟。然后将2.16g(3.2mmol)[(μ-Cl)(η4-1,5-cod)Ir]2溶于200ml甲苯中并在室温下通过滴加与该盐混合物混合。将反应混合物在室温下搅拌1小时,在70℃下搅拌2小时,然后回流过夜。然后将该混合物浓缩至干并将残余物用二氯甲烷萃取。在再次浓缩至干后,通过柱色谱提纯棕色残余物。得到1.15g黄色粉末(理论值的24%)。
1H NMR(CD2Cl2,500MHz):δ=7.42(m,2H),7.35(m,1H),7.20-7.00(m,6H),6.95,6.90,(各为s,1H),6.77,6.76,6.74 6.69(各为m,1H)(各自为CHPh或NCHCHN),2.94(m,6H,CH3),2.87(s,3H,CH3)。
13C NMR(CD2Cl2,125MHz):δ=173.3,171.8,170.8(NCN),150.8,150.1,149.7,149.4,148.8,147.0(Cq),141.4,141.2,139.5,125.1,125.0,124.8,121.6,121.3,121.1,114.3,114.2,114.1,110.0,109.9,109.5(CHPh,NCHCHN),119.9,119.8,119.7,107.5,107.1,106.9(Cq,CN),36.5(强度x2),35.3(CH3)。
光谱法:λ=459nm,436nm(在聚甲基丙烯酸甲酯(PMMA)中的最大发光波长,肩峰)
量子产率:57%(在PMMA中)
元素分析(对经验式IrC33H24N9的计算值):
计算值(重量%) 实测值(重量%)
碳 53.7 54.0
氮 17.1 16.2
氢 3.3 3.7
热重分析法/差示热分析(加热速率:5K/min):
在约100℃-160℃下失去溶剂
从约370℃开始分解
HPLC:>99面积%(柱:Purospher Si 80,洗脱剂:庚烷/异丙醇=70/30(体积%))
实施例2:OLED的生产
a)
用作阳极的ITO基材首先用LCD生产用市售洗涤剂(Deconex20NS和25ORGAN-ACID中和剂)清洁,然后在超声浴中在丙酮/异丙醇混合物中清洁。为了除去可能的有机残余物,再在臭氧箱中将基材暴露于连续的臭氧流25分钟。该处理也改善了该ITO的空穴注入。
然后通过在约2nm/min的速率和约10-7毫巴下的气相沉积将下述有机材料施用于已清洁的基材上。作为空穴导体,首先将1-TNATA(4,4’,4”-三(N-(萘-1-基)-N-苯基氨基)三苯基胺)以17.5nm的层厚施用于基材上。然后通过气相沉积施用9.5nm厚的化合物C1的激子阻挡层:
(对于制备,参见申请PCT/EP/04/09269中的Ir配合物(7))。
然后通过气相沉积以20nm的厚度施用34重量%来自实施例1c)的化合物1c):
和66重量%化合物C2:
(1,3-亚苯基-10,10′-二(吩噻嗪)5,5′-二氧化物)的混合物,前一化合物用作发光剂,后一化合物用作基体材料。然后通过气相沉积施用厚度为47.5nm的2,9-二甲基-4,7-二苯基-1,10-菲咯啉(BCP)的空穴阻挡剂和电子传导剂层,0.75nm厚的氟化锂层,最后是110nm厚的Al电极。
为了表征该OLED,在各种电流和电压下记录电致发光光谱。此外,结合发光输出测量电流-电压特性。通过用光度计校准可以将光输出转化为光度参数。
对于所述OLED,得到下列电光数据:
最大发光波长 | 466nm |
CIE(x,y) | 0.17;0.21 |
光度效率 | 11.7cd/A |
功率系数 | 9.9lm/W |
外部量子产率 | 7.3% |
在100cd/m2发光密度下的光度效率 | 10.3cd/A |
最大发光密度 | 2700cd/m2 |
化合物C2按如下制备:
i)根据K.Okada等,J.Am.Chem.Soc.1996,118,第3047-3048页制备1,3-亚苯基-10,10′-二(吩噻嗪)。
将18.5g(91.9mmol)吩噻嗪、15.6g(46.3mmol)98%1,3-二碘代苯、 19.4g(140mmol)碳酸钾和1.16g(18.3mmol)活化的铜粉加热到200℃并在该温度下搅拌24小时。将反应混合物冷却到140℃,然后与200ml乙酸乙酯混合。将悬浮液加热到在回流下沸腾1小时,然后热过滤。将滤液用300ml甲醇稀释,沉淀出固体并吸滤,用甲醇洗涤并在80℃和减压下干燥。得到8.91g熔点为186-188℃的粉红色固体。
ii)1,3-亚苯基-10,10′-二(吩噻嗪)5,5′-二氧化物(C2)的制备
将6.28g(13.3mmol)1,3-亚苯基-10,10′-二(吩噻嗪)溶于220ml二氯甲烷中。在室温下搅拌15分钟后,分批加入17.9g(79.9mmol)77%间氯过苯甲酸。将反应溶液在室温下搅拌24小时,在此过程中沉淀出固体。过滤该溶液,将残余物用二氯甲烷洗涤并吸干。将固体悬浮于热水中。用5%氢氧化钾溶液将含水悬浮液调节至pH为11,然后热过滤。残余物用热水洗涤并在80℃和减压下干燥。固体(5.07g)由二甲基甲酰胺中重结晶。以分析纯形式得到3.72g熔点为412℃的无色微晶体,其甲苯溶液在λ=375nm(S)处发荧光。
b)
ITO基材如a)所述进行预处理。
然后通过在约2nm/min的速率和约10-7毫巴下的气相沉积将下述有机材料施用于已清洁的基材上。作为空穴导体,首先将1-TNATA(4,4’,4”-三(N-(萘-1-基)-N-苯基氨基)三苯基胺)以15nm的层厚施用于基材上。然后通过气相沉积施用9nm厚的化合物C1的激子阻挡层。然后通过气相沉积以16nm的厚度施用55重量%化合物1c)和45重量%1,3-二(N-咔唑基)苯的混合物,前一化合物用作发光剂,后一化合物用作基体材料。然后通过气相沉积施用厚度为45nm的BCP的空穴阻挡剂和电子传导剂层,0.75nm厚的氟化锂层,最后是110nm厚的Al电极。
为了表征该OLED,在各种电流和电压下记录电致发光光谱。此外,结合发光输出测量电流-电压特性。通过用光度计校准可以将光输出转化为光度参数。
实施例3-13
由相应的咪唑鎓盐和[(μ-Cl)Ir(η4-1,5-cod)]2制备实施例3-13的铱-卡宾 配合物的通用方法:
将1当量在二噁烷或甲苯中的相应咪唑鎓盐的悬浮液与1当量双(三甲基甲硅烷基)氨化钾(0.5M,在甲苯中)在氩气下缓慢混合,将混合物在室温下搅拌30分钟。将该混合物与0.1当量[(μ-Cl)Ir(η4-1,5-cod)]2混合并在回流下搅拌16小时。在冷却至室温后,过滤沉淀并用二噁烷洗涤。将合并的滤液浓缩至干并通过柱色谱提纯粗产物。
实施例3:制备经式-三[1-(4’-氰基苯基)-3-甲基苯并咪唑-2-亚基-C2,C2′]铱(III)
(″Ir(cn-pmbic)3″)
a)制备1-(4-氰基苯基)苯并咪唑(根据K.Nishiura,Y.Urawa,S.Soda,Adv.Synth.Catal.2004,346,1679)
首先将氢化钠(60%,在矿物油中;24.0g;0.60mol)装入烧瓶中并与N,N-二甲基甲酰胺(80ml)混合。将苯并咪唑(73.3g,0.60mol)在N,N-二甲基甲酰胺(250ml)中的溶液经1小时滴加入所述悬浮液中。在H2放出结束之后,加入4-氯苄腈(55.6g,0.40mol),然后将混合物加热至130℃并维持10.5小时。在冷却至室温之后,将反应混合物加入水(4L)中并吸滤所形成的残留物,将其用水洗涤并在减压下干燥。得到90.6g仍包含矿物油杂质的1-(4-氰基苯基)苯并咪唑。
1H NMR(400MHz,CD2Cl2):δ=7.35-7.41(m,2H),7.59-7.63(m,1H),7.70(d,J=8.5Hz,2H),7.83-7.86(m,1H),7.90(d,J=8.5Hz,2H),8.15(s,1H)。
b)制备碘化1-(4-氰基苯基)-3-甲基苯并咪唑鎓
首先将1-(4-氰基苯基)苯并咪唑(90g,略微污染有矿物油)装入四氢呋喃(250ml)中并与碘甲烷(116g,0.82mol)混合,在40℃下放置25.5小时。过滤所形成的残留物,将其用乙醇洗涤并在减压下干燥。得到123g碘化 1-(4-氰基苯基)-3-甲基苯并咪唑鎓。
1H NMR(400MHz,DMSO):δ=4.20(s,3H),7.74-7.84(m,2H),7.93(d,J=8.4Hz,1H),8.07(d,J=8.8Hz,2H),8.18(d,J=8.4Hz,1H),8.30(d,J=8.8Hz,2H),10.24(s,1H)。
c)制备经式-三[1-(4’-氰基苯基)-3-甲基苯并咪唑-2-亚基-C2,C2′]铱(III)
卡宾配合物通过使步骤b)中得到的咪唑鎓盐与[(μ-Cl)(η4-1,5-cod)Ir]2 根据上述通用方法反应而制备。在用2∶1乙酸乙酯/甲醇洗脱之后,以理论产率的24%得到作为浅黄色粉末的产物。
1H NMR(d6-DMSO,500MHz):δ=3.18(s,3H),3.22(s,3H),3.29(s,3H),6.81(d,J 2.0,1H),7.03(d,J 2.0,1H),7.10(d,J 2.0,1H),7.30-7.47(m,12H),7.94(d,J 8.0,1H),7.95(d,J 3.5,1H),7.97(d,J 3.5,1H),8.15(d,J 8.0,1H),8.16(d,J 3.5,1H),8.17(d,J 3.5,1H)。
13C NMR(CD2Cl2,125MHz):δ=187.0,185.0,183.7(NCN),153.4,152.6,151.8,150.5,149.7,147.5(Cq或CN),141.9,141.7,139.9(CHPh),137.10,137.07,136.7,132.63(2),132.59(Cq或CN),127.1,127.0,126.7,124.3,124.2(2),123.71,123.66,123.5,(CHPh),120.68,120.66,120.65(Cq或CN),113.1,112.9,112.5,112.2,112.1,111.9,111.1,110.9(2)(CHPh),108.6,108.3,108.2(Cq或CN),34.3,34.2,33.5(NCH3)。
实施例4:制备三[1-苯基-3-甲基-5-氮杂苯并咪唑-2-亚基-C2,C2′]铱(III)
(″Ir(pmabic)3″)
a)制备4-(N-苯基氨基)-3-硝基吡啶
将苯胺(2.2ml,24mmol,1.2当量)和三乙胺(3.7ml,27mmol,1.3当量)在氯仿(6ml)中的溶液在0℃和氩气下滴加入4-氯-3-硝基吡啶(3.2g,20mmol,1当量)在氯仿(12ml)中的悬浮液中。随后将混合物在回流下搅拌16小时。在冷却至室温之后,将有机相用水洗涤、经硫酸钠干燥并浓缩至 干。通过柱色谱(硅胶,9∶1乙酸乙酯/环己烷)分离粗产物。产量:3.4g(16mmol,80%)。
1H NMR(CDCl3,400MHz):δ=6.95(d,J 6.0,1H),7.29(d,J 7.5,2H),7.35(t,J 7.5,1H),7.48(dd,J 8.0,7.5,2H),8.26(br s,1H),9.31(brs,1H),9.67(s,1H)。
b)制备4-(N-苯基氨基)-3-氨基吡啶
将4-(N-苯基氨基)-3-硝基吡啶(5.6g,25mmol)在四氢呋喃(25ml)中的溶液在室温下与活性炭(2.5g)上的钯和丙酸(3滴)混合。在混合物中通入氢气3小时。随后,通过Celite过滤悬浮液并将滤液浓缩至干。产量:4.3g(23mmol,93%)。
1H NMR(CDCl3,400MHz):δ=3.40(br s,2H),6.37(br s,1H),6.99(d,J 5.5,1H),7.06-7.19(m,3H),7.34(dd,J 8.0,7.5,2H),7.88(d,J 5.5,1H),8.07(s,1H)。
c)制备4-(N-苯基氨基)-3-(N-甲酰氨基)吡啶
将4-(N-苯基氨基)-3-氨基吡啶(4.0g,22mmol,1当量)在甲酸(9.9g,216mmol,10当量)中的溶液在0℃下与乙酸酐(2.6g,26mmol,1.2当量)小心地混合。将混合物在室温下搅拌16小时,用水小心地稀释并用乙醚萃取。将有机相用水和饱和碳酸氢钠溶液洗涤,经硫酸钠干燥并浓缩至干。通过柱色谱(硅胶,9∶1乙酸乙酯/环己烷)提纯粗产物。产量:3.3g(15mmol,71%)。
1H NMR(CDCl3,400MHz):δ=6.42(br s,1H),7.04(d,J 5.5,1H),7.07-7.21(m,3H),7.36(dd,J 8.0,7.5,2H),7.91(d,J 5.5,1H),8.11(s,1H),8.54(br s,1H),10.05(s,1H)。
d)制备4-(N-苯基氨基)-3-(N-甲基氨基)吡啶
将4-(N-苯基氨基)-3-(N-甲酰氨基)吡啶(3.0g,14mmol,1当量)在无水四氢呋喃(20ml)中的溶液在0℃下与氢化铝锂(0.5g,14mmol,1当量)小心地混合。将混合物在回流下搅拌6小时。在冷却至室温后,将混合物水解,通过Celite过滤并浓缩至干。用二氯甲烷萃取残留物并在旋转蒸发器上除去溶剂。通过柱色谱(硅胶,9∶1乙酸乙酯/环己烷)分离粗产物。产量: 1.0g(5mmol,35%)。
1H NMR(CDCl3,400MHz):δ=2.73(d,J 5.0,3H),5.44(br d,J 4.0,1H),6.36(br s,1H),6.97(d,J 5.5,1H),7.06-7.19(m,3H),7.34(dd,J8.0,7.5,2H),7.86(d,J 5.5,1H),8.04(s,1H)。
e)制备1-苯基-3-甲基-5-氮杂苯并咪唑鎓四氟硼酸盐
将4-(N-苯基氨基)-3-(N-甲基氨基)吡啶(0.90g,4.5mmol,1当量)和四氟硼酸铵(0.47g,4.5mmol,1当量)与原甲酸三乙酯(9.37g,63.2mmol,14当量)混合并将混合物在回流下搅拌8小时。在冷却至室温之后,将混合物浓缩并与乙醇混合,过滤沉淀产物。产量:0.70g(2.3mmol,52%)。
1H NMR(CD2Cl2,400MHz):δ=4.03(s,3H),7.12(d,J 5.5,1H),7.20-7.32(m,3H),7.44(dd,J 8.0,7.5,2H),7.98(d,J 5.5,1H),8.12(s,1H),9.60(s,1H)。
f)制备三[1-苯基-3-甲基-5-氮杂苯并咪唑-2-亚基-C2,C2′]铱(III)
卡宾配合物通过使在步骤e)中得到的咪唑鎓盐与[(μ-Cl)(η4-1,5-cod)Ir]2根据上述通用方法反应而制备。在用9∶1乙酸乙酯/甲醇洗脱之后,以理论产率的10%得到作为异构体混合物的产物。
ESI-MS(MeCN/H2O 8∶2):m/z=817.9552(M+H+,校正同位素谱图,计算:817.9569)。
实施例5:制备经式-三[1-(4’-氰基-3’,5’-二甲基苯基)-3-甲基咪唑-2-亚基-C2,C2′]铱(III)
(″Ir(me2-cn-pmic)3″)
a)制备1-(4-氰基-3,5-二甲基苯基)咪唑
将4-氯-2,6-二甲基苄腈(5.15g,32mmol)溶于N-甲基吡咯烷酮(50ml)中并在冷却下与咪唑(3.27g,48mmol)和碳酸钠(5.09g,48mmol)混合,加 热至133℃并搅拌14小时。然后,将混合物逐步加热至170℃,并且总共经14小时加入另外的3.50g(32.2mmol)碳酸钠和1.3g(13.6mmol)咪唑,然后将混合物在170℃下再搅拌7小时。随后将反应混合物冷却至室温并加入水(400ml)中。将固体产物吸滤并用甲醇洗涤。得到3.12g 1-(4-氰基-3,5-二甲基苯基)咪唑。
1H NMR(400MHz,CD2Cl2):δ=2.63(s,6H),7.17(s,1H),7.21(s,2H),7.35(dd,J=1.4,1.4Hz,1H),7.90(s,1H)。
b)制备碘化1-(4-氰基-3,5-二甲基苯基)-3-甲基咪唑鎓
将1-(4-氰基-3,5-二甲基苯基)咪唑(3.10g,19.3mmol)和碘甲烷(13.7g,96.7mmol)在四氢呋喃(50ml)中搅拌并在室温下静置2天。将所形成的残留物过滤,用四氢呋喃洗涤并在减压下干燥。
1H NMR(400MHz,DMSO):δ=2.58(s,6H),3.96(s,3H),7.80(s,2H),7.99(dd,J=1.7,1.7Hz,1H),8.36(dd,J=1.7,1.7Hz,1H),9.89(s,1H)。
c)制备经式-三[1-(4’-氰基-3’,5’-二甲基苯基)-3-甲基咪唑-2-亚基-C2,C2′]铱(III)
卡宾配合物通过使在步骤b)中得到的咪唑鎓盐与[(μ-Cl)(η4-1,5-cod)Ir]2根据上述通用方法反应而制备。在用梯度的甲基叔丁基醚/乙酸乙酯洗脱之后,以理论产率的9%得到产物。
1H NMR(CD2Cl2,400MHz):δ=1.58(s,3H),1.60(s,3H),1.70(s,3H),2.43(s,6H),2.44(s,3H),2.71(s,3H),2.82(s,3H),2.88(s,3H),6.69(d,J 2.0,1H),6.73(d,J 2.0,1H),6.75(d,J 2.0,1H),6.94(s,1H),6.96(s,1H),6.97(s,1H),7.38(d,J 2.0,1H),7.42(d,J 2.0,1H),7.45(d,J 2.0,1H)。
ESI-MS(MeCN/H2O 8∶2):m/z=824.2803(M+H+,校正同位素谱图,计算:824.2796)。
实施例6:制备三[1-(2’-苯并[b]噻吩基)-3-甲基苯并咪唑-2-亚基-C2,C2′]铱(III)
(″Ir(btmbic)3″)
a)制备2-溴苯并[b]噻吩(根据G.W.Stacy等,J.Org.Chem.1965,30,4074;b)R.M.Acheson,D.R.Harrison,J.Chem.Soc.C 1970,1764)
将苯并[b]噻吩(75.1g,0.56mol,1当量)在无水乙醚(300ml)中的溶液在氮气和-78℃下与正丁基锂(2.5M,在正己烷中,271ml,0.68mol,1.2当量)缓慢混合。将溶液在-78℃下搅拌30分钟,然后在0℃下小心地滴加入溴(34.4ml,0.68mol,1.2当量)。将混合物在室温下搅拌30分钟并与5%硫代硫酸钠溶液混合。在加入水之后,将有机相移出并用水、5%氢氧化钠溶液、1M盐酸、饱和碳酸氢钠溶液和水洗涤。将有机相经硫酸钠干燥并在旋转蒸发器上浓缩。通过真空蒸馏提纯粗产物。产量:84.7g(0.40mol,71%)。
1H NMR(CD2Cl2,400MHz):δ=7.25-7.33(m,2H),7.28(s,1H),7.62-7.72(m,2H)。
b)制备1-(2’-苯并[b]噻吩基)苯并咪唑
将2-溴苯并[b]噻吩(50.0g,235mmol,1当量)、苯并咪唑(33.3g,282mmol,1.2当量)、磷酸钾(96.6g,470mmol,2当量)、碘化亚铜(I)(4.5g,24mmol,10mol%)和反式-1,2-二氨基环己烷(5.7ml,47mmol,20mol%)在无水二噁烷(450ml)中的混合物在回流和氩气下搅拌16小时。在冷却至室温之后,过滤混合物并将滤液浓缩至干。通过柱色谱(硅胶,乙酸乙酯)提纯粗产物。产量:4.9g(20mmol,8%)。
1H NMR(CD2Cl2,400MHz):δ=7.33-7.48(m,5H),7.71-7.74(m,1H),7.80-7.88(m,3H),8.16(s,1H)。
c)制备碘化1-(2’-苯并[b]噻吩基)-3-甲基苯并咪唑鎓
将1-(2’-苯并[b]噻吩基)苯并咪唑(4.7g,12mmol,1当量)在四氢呋喃 (40ml)中的溶液与碘甲烷(3.7ml,59mmol,5当量)在氮气下混合并在室温下静置16小时。将混合物悬浮在少量乙醇中并将产物过滤。产量:4.45g(11mmol,95%)。
1H NMR(d6-DMSO,400MHz):δ=4.19(s,3H),7.56-7.61(m,2H),7.76-7.86(m,2H),8.02-8.10(m,2H),8.06(s,1H),8.16-8.22(m,2H),10.27(s,1H)。
d)制备三[1-(2’-苯并[b]噻吩基)-3-甲基苯并咪唑-2-亚基-C2,C2′]铱(III)
卡宾配合物通过使在步骤c)中得到的咪唑鎓盐与[(μ-Cl)(η4-1,5-cod)Ir]2根据上述通用方法反应而制备。在用9∶1乙酸乙酯/环己烷洗脱之后,以10%的面式异构体和68%的异构体混合物(其中面式/经式异构体之比约为1∶1)的产率得到产物。
面式异构体分析:
1H NMR(d6-DMSO,400MHz):δ=3.22(s,9H),6.28(d,J 8.0,3H),6.53(ddd,J 7.5,7.5,1.0,3H),6.91(ddd,J 7.5,7.5,1.0,3H),7.32(ddd,J 8.0,8.0,1.0,3H),7.40(ddd,J 8.0,8.0,1.0,3H),7.57(d,J 8.0,3H),7.82(d,J 8.0,3H),7.94(d,J 8.0,3H)。
APCI-MS(MeCN):m/z=981.1556(M+,校正同位素谱图,计算:981.1613)。
实施例7:制备经式-三[1-(4’-吡啶基)-3-甲基咪唑-2-亚基-C2,C2′]铱(III)
(″Ir(pymic)3″)
a)制备氯化1-(4’-吡啶基)-3-甲基咪唑鎓
将4-氯吡啶盐酸盐(91.6g,0.61mol)与饱和碳酸氢钠溶液混合并用二氯甲烷萃取4次。将合并的有机相经硫酸钠干燥、过滤并浓缩至干。将所得油(52.7g,0.46mol)与甲基咪唑(38.1g,0.46mol)混合并在130℃下搅拌6小时。在冷却至室温之后,将混合物溶解在乙醇中并通过加入正己烷沉淀产 物。产量:56.7g(0.29mol,63%)。
1H NMR(d6-DMSO,400MHz):δ=4.00(s,3H),7.98(dd,J 4.5,1.5,2H),8.07(m,1H),8.58(m,1H),8.86(dd,J 4.5,1.5,2H),10.42(s,1H)。
b)制备经式-三[1-(4’-吡啶基)-3-甲基咪唑-2-亚基-C2,C2′]铱(III)
卡宾配合物通过使在步骤a)中得到的咪唑鎓盐与[(μ-Cl)(η4-1,5-cod)Ir]2根据上述通用方法反应而制备。在用异丁醇洗脱之后,以理论产率的8%得到产物。
1H NMR(CD2Cl2,400MHz):δ=3.03(s,3H),3.07(s,3H),3.10(s,3H),6.82-6.86(m,3H),7.02-7.06(m,3H),7.45(d,J 2.0,1H),7.51(d,J 2.0,1H),7.54(d,J 2.0,1H),7.66(d,J 0.5,1H),7.80(d,J 0.5,1H),7.89(d,J 0.5,1H),8.04(d,J 5.0,1H),8.07(d,J 5.0,1H),8.08(d,J 5.0,1H)。
ESI-MS(MeCN/H2O 8∶2):m/z=666.1844(M+H+,校正同位素谱图,计算:666.1839)
实施例8:制备经式-三[1-(4’-氯苯基)-3-甲基咪唑-2-亚基-C2,C2′]铱(III)
(″Ir(cl-pmic)3″)
a)制备1-(4-氯苯基)咪唑(根据S.U.Son,I.K.Park,J.Park,T.Hyeon,Chem.Commun.2004,778)
将1-氯-4-氟苯(16.3g,124mmol)和咪唑(5.0g,73.4mmol)溶于N,N-二甲基甲酰胺(30ml)中并与氢化钠(60%,在矿物油中;3.82g,95.4mmol)在搅拌下混合,然后加热至130℃并维持5小时。在冷却之后,将反应混合物缓慢加入水中。然后将所形成的沉淀过滤,用石油醚洗涤,然后在减压下干燥。得到10.3g 1-(4-氯苯基)咪唑。
1H NMR(400MHz,CD2Cl2):δ=7.16(brs,1H),7.30(dd,J=1.2,1.2Hz,1H),7.38(d,J=7.7Hz,2H),7.48(d,J=7.7Hz,2H),7.82(brs,1H)。
b)制备碘化1-(4-氯苯基)-3-甲基咪唑鎓
将1-(4-氯苯基)咪唑(0.37g,2.07mmol)溶于四氢呋喃(5ml)中,然后与碘甲烷(1.47g,10.4mmol)混合并静置20小时。随后将所形成的沉淀过滤并用乙醇和石油醚洗涤,然后在减压下干燥。得到0.46g碘化1-(4-氯苯基)-3-甲基咪唑鎓。
1H NMR(400MHz,DMSO):δ=3.96(s,3H),7.76-7.84(m,4H),7.97(dd,J=1.8,1.8Hz,1H),8.30(dd,J=1.8,1.8Hz,1H),9.80(brs,1H)。
c)制备经式-三[1-(4’-氯苯基)-3-甲基咪唑-2-亚基-C2,C2′]-铱(III)
卡宾配合物通过使在步骤b)中得到的咪唑鎓盐与[(μ-Cl)(η4-1,5-cod)Ir]2根据上述通用方法反应而制备。在进行柱色谱提纯之后,以理论产率的30%得到作为白色粉末的产物。
1H NMR(CD2Cl2,500MHz):δ=7.43(m,2H),7.38(m,1H),7.08(m,3H),6.90-6.75(m,6H),6.67(m,2H),6.42(m,1H)(各CHPh或NCHCHN),3.06(s,3H,NCH3),3.02(s,3H,NCH3),2.99(s,3H,NCH3)。
13C NMR(CD2Cl2,125MHz):δ=173.9,172.1,171.3(NCN),153.9,152.7,151.2,147.1,146.4,145.7(Cq),138.5,138.1,136.6(CHPh或NCHCHN),130.5,130.3,130.2(Cq),121.8,121.6,121.3,120.5,120.3,120.1,115.04,114.99,114.9,112.00,111.97,111.5(CHPh或NCHCHN),37.4(强度加倍),36.2(NCH3)。
实施例9:制备经式-三[1-(4’-氰基苯基)-3-(2’-丙基)苯并咪唑-2-亚基-C2,C2′]铱(III)
(″Ir(cn-pibic)3″)
a)制备N-(2-丙基)-2-硝基苯胺(根据H.J.Altenbach等,TetrahedronAsymmetry 2002,13,137-144)
将2-硝基苯胺(10.0g,72.4mmol)溶于二氯甲烷(60ml)和冰醋酸(10ml)的混合物中。滴加入丙酮(16ml,218mmol)并搅拌所得溶液,在加料结束之后,再搅拌5分钟。然后,在0℃和搅拌下,经40分钟滴加入硼烷-甲硫醚的配合物(8.6ml,10M,86mmol)。然后除去冰浴并将混合物搅拌1小时。随后通过缓慢加入氨溶液(约16ml)将反应混合物的pH调至8。移出有机相并用二氯甲烷将水相萃取两次。将有机相合并并经硫酸钠干燥,然后在减压下除去溶剂。以这种方式得到具有良好纯度的N-(2-丙基)-2-硝基苯胺目标化合物并且无需进一步提纯而进一步反应。
1H NMR(400MHz,CD2Cl2):δ=1.30(d,J=6.4Hz,6H),3.82(hept,J=6.4Hz,1H),6.58(ddd,J=8.5,7.0,1.5Hz,1H),6.87(d,J=8.5Hz,1H),7.41(ddd,J=8.5,7.0,1.5Hz),7.97(brs,1H),8.10(dd,J=8.5,1.8Hz,1H)。
b)制备N-(2-丙基)-1,2-苯二胺(根据H.J.Altenbach等,TetrahedronAsymmetry 2002,13,137-144)
将2-硝基-N-异丙基苯胺(83.5g,463mmol)溶于甲醇(675ml)中并与在活性炭上的钯(11.0g,5-10%Pd,水含量53%)混合。氢化在1巴的H2气氛下以及在25-38℃的内部温度和快速搅拌下进行。反应混合物在2.5小时内由黄色变为无色,然后又在氢气气氛下搅拌过夜。随后,在除去过量的氢气之后,过滤钯催化剂并借助短柱过滤(硅胶、甲醇)提纯粗产物。在减压下除去溶剂之后,以黑色油得到产物(69.55g,463mmol)。
1H NMR(CDCl3,400MHz):δ=1.20(d,J=6.0Hz,6H),3.29(brs,3H),3.57(hept,J=6.0Hz,1H),6.62-6.70(m,3H),6.78-6.82(m,1H)。
c)制备N-(4-氰基苯基)-N′-(2-丙基)苯二胺
将N-(2-丙基)-1,2-苯二胺(1.50g,10mmol)和4-溴苄腈(1.82g,10mmol)溶于甲苯(200ml)中并在约70℃下与三(二亚苄基丙酮)二钯(0)(92mg,1mol%)、9,9-二甲基-4,5-二-(二苯基膦基)呫吨(177mg,3mol%)、叔丁醇钠 (964mg,10mmol)和水(130μl)搅拌混合,然后将混合物在80℃下搅拌16小时。在冷却之后,将反应混合物用水稀释,用乙酸乙酯萃取,在干燥有机相之后,在减压下除去溶剂。在色谱法(环己烷∶乙酸乙酯)之后,得到1.46gN-(4-氰基苯基)-N′-(2-丙基)苯二胺。
1H NMR(400MHz,CD2Cl2):δ=1.55(d,6H,J=6.4Hz),3.64(sept,1H,J=6.3Hz),3.86(s,宽峰,1H),5.60(s,宽峰,1H),6.63-6.67(m,3H),6.74(d,1H,J=8.2Hz),7.07(d,1H,J=6.4Hz),7.42(d,2H,J=6.7Hz)。
d)制备1-(4-氰基苯基)-3-(2-丙基)苯并咪唑鎓四氟硼酸盐
将N-(4-氰基苯基)-N′-(2-丙基)苯二胺(1.07g,4.25mmol)和四氟硼酸铵(0.46g,4.25mmol)与原甲酸三乙酯(8.83g,59.5mmol)混合,将所得混合物在回流下加热8小时。在将反应混合物冷却并在减压下除去部分溶剂之后,将溶液与乙醇混合,将沉淀的固体过滤并在减压下干燥。得到0.35g 1-(4-氰基苯基)-3-(2-丙基)苯并咪唑鎓四氟硼酸盐。
1H NMR(400MHz,CD2Cl2):δ=1.84(d,6H,J=6.7Hz),5.09(sept,1H,J=6.7Hz),7.72-7.81(m,3H),7.92-7.95(m,3H),8.00(d,2H,J=8.1Hz),9.60(s,1H)。
e)制备经式-三[1-(4’-氰基苯基)-3-(2’-丙基)苯并咪唑-2-亚基-C2,C2′]铱(III)
卡宾配合物通过使在步骤d)中得到的咪唑鎓盐与[(μ-Cl)(η4-1,5-cod)Ir]2根据上述通用方法反应而制备。在进行柱色谱提纯之后,以理论产率的28%得到作为亮黄色粉末的产物。
1H NMR(CD2Cl2,500MHz):δ=8.16(m,3H,CHPh),7.96(m,2H,CHPh),7.90(d,3JH,H=8.3Hz,1H,CHPh),7.54(m,3H,CHPh),7.36(m,8H,CHPh),7.18(s,1H,CHPh),6.96(s,1H,CHPh),6.90(s,1H,CHPh),6.85(s,1H,CHPh),4.60(m,2H,CHiPr),4.46(m,1H,CHiPr),1.64(d, 3JH,H=7.1Hz,3H,CH3),1.36(d,3JH,H=7.1Hz,3H,CH3),1.31(d,3JH,H=7.1Hz,3H,CH3),0.84(d,3JH,H=7.1Hz,3H,CH3),0.65(d,3JH,H=6.9Hz,3H,CH3),0.59(d,3JH,H=7.1Hz,3H,CH3)。
13C NMR(CD2Cl2,125MHz):δ=186.9,184.5,183.0(NCN),153.2, 152.6,152.0,150.5,150.4,148.4(Cq),141.5,140.3,140.0(CHPh),133.9,133.88,133.83,133.77,133.71,133.6(Cq),127.1,127.0,126.6,125.8,124.1,124.0,123.3,123.25,123.0(CHPh),120.7,120.5,120.47(Cq),113.3,113.27,113.2,113.12,113.08,112.7,112.67,112.4,112.0(CHPh),108.6,108.2,108.1(Cq),54.4,52.6,52.4(CHiPr),21.5,20.7,20.5,20.4,20.3,20.1(CH3)。
实施例10:制备经式-三[1-(4’-氰基苯基)-3-甲基-4-叔丁基咪唑-2-亚基-C2,C2′]铱(III)
(″Ir(tbu-cn-pmic)3″)
a)制备1-(4-氰基苯基)-4-(1,1-二甲基乙基)咪唑
将4-(1,1-二甲基乙基)咪唑(根据Chem.Ber.1997,130,1201-1212制备)(40.6g,327mmol)和4-氟苄腈溶于N,N-二甲基甲酰胺(700ml)中,随后将溶液与氢化钠(60%,在矿物油中,16.4g,409mmol)混合并用冰冷却。然后将反应溶液在室温下搅拌16小时,然后加热至100℃并搅拌4小时。在冷却后,将反应混合物加入冰水中并用二氯甲烷萃取3次。除去溶剂,再次将残留物溶于少量二氯甲烷中并用石油醚沉淀。将残留物过滤并在减压下干燥。得到48.5g 1-(4-氰基苯基)-4-(1,1-二甲基乙基)咪唑。
1H NMR(400MHz,CDCl3):δ=1.34(s,9H),7.03(s,1H),7.51(d,J=8.5Hz,2H),7.79(d,J=8.5z,2H),7.88(s,1H)。
b)制备碘化1-(4-氰基苯基)-3-甲基-4-(1,1-二甲基乙基)咪唑鎓
将48.5g 1-(4-氰基苯基)-4-(1,1-二甲基乙基)咪唑溶于四氢呋喃(300ml)中并与碘甲烷(152.6g,1.08mol)混合。使溶液在室温下反应2天。随后将所形成的沉淀过滤,用乙醇洗涤并在减压下干燥。得到59.9g碘化1-(4-氰 基苯基)-3-甲基-4-(1,1-二甲基乙基)咪唑鎓。
1H NMR(400MHz,DMSO):δ=1.42(s,9H),4.04(s,3H),8.03(d,J=8.8Hz,2H),8.18(d,J=2.2Hz,1H),8.21(d,J=8.8Hz,2H),9.84(d,J=2.2Hz,1H)。
c)制备经式-三[1-(4’-氰基苯基)-3-甲基-4-叔丁基咪唑-2-亚基-C2,C2′]铱(III)
卡宾配合物通过使在步骤b)中得到的咪唑鎓盐与[(μ-Cl)(η4-1,5-cod)Ir]2根据上述通用方法反应而制备。在进行柱色谱提纯之后,以理论产率的57%得到作为黄色粉末的产物。
1H NMR(CD2Cl2,500MHz):δ=7.18-7.00(m,9H),6.82(m,2H),6.54(m,1H)(各CHPh或NCHCN),3.11(s,3H,NCH3),3.08(s,3H,NCH3),3.03(s,3H,NCH3),1.30(s,9H,CH3,tBu),1.29(s,9H,CH3,tBu),1.25(s,9H,CH3,tBu)。
13C NMR(CD2Cl2,125MHz):δ=175.2,174.7,172.8(NCN),150.9,150.2,149.6,149.5,149.4,147.9,141.8,141.7,141.1(Cq),140.8,140.7,139.0,125.0,124.8,124.6(CHPh或NCHCN),120.0,119.92,119.86(Cq或CN),110.41,110.39,110.0,109.7,109.6,109.2(CHPh或NCHCN),107.2,106.8,106.4(Cq或CN),36.4,36.3,34.4(NCH3),30.5,30.42,30.39(Cq,tBu),28.4(CH3,tBu)。
实施例11:制备经式-三[1-苯基-3-(2’-丙基)苯并咪唑-2-亚基-C2,C2′]铱(III)
(″Ir(pibic)3″)
a)制备N-苯基-N′-(2-丙基)苯二胺
首先在具有磁力搅拌棒和冷却器的四颈烧瓶中在氮气下装入在乙醚中的1当量,3.00g(16.4mmol)2-氨基二苯基胺(约1M)。用冰浴冷却微红色溶 液,然后在10℃下基于每摩尔2-氨基二苯基胺滴加入180ml浓盐酸。在此过程中,沉淀出白色固体。通过吸滤器吸滤混合物。用乙醚洗涤残留物并在50℃和减压下干燥过夜。不经进一步提纯而使用所得盐酸盐。在具有磁力搅拌棒的50ml烧瓶中,将4.19g(19.2mmol)2-氨基二苯基胺盐酸盐溶于25ml甲醇中。将1.66g(28.7mmol)丙酮和2.17g(57.5mmol)硼氢化钠加入用冰浴冷却的所述微红色溶液中。在此过程中,溶液猛烈发泡并变成浅绿色悬浮液。将其在室温下搅拌过周末。将混合物加入水中并用二氯甲烷萃取。将有机相经硫酸钠干燥并在减压下除去溶剂。通过柱色谱(石油醚∶乙酸乙酯)提纯产物。
1H NMR(400MHz,CDCl3):δ=1.18(d,6H,J=6.4Hz),3.64(sept.,1H,J=6.5Hz),3.96(s,宽峰,1H),5.01(s,宽峰,1H),6.65(dt,1H,J=7.5Hz,J=1.0Hz),6.69-6.74(m,3H),6.81(t,1H,J=7.4Hz),7.10(t,2H,J=7.9Hz),7.19(t,2H,J=7.4Hz)。
b)制备1-苯基-3-(2-丙基)苯并咪唑鎓四氟硼酸盐
将N-苯基-N′-(2-丙基)苯二胺(1.82g,8.0mmol)溶于原甲酸三乙酯(16.6g,112mmol)中并与四氟硼酸铵(0.84g,8.0mmol)混合,并在回流下加热8小时。在冷却至室温之后,将所得残留物过滤、用原甲酸三乙酯洗涤并在减压下干燥。得到1.95g 1-苯基-3-(2-丙基)苯并咪唑鎓四氟硼酸盐。
1H NMR(CDCl3,400MHz):δ=1.86(d,6H,J=6.8Hz),5.14(sept,1H,J=6.6Hz),7.63-7.77(m,8H),7.84(d,1H,J=9.4Hz),9.63(s,1H)。
c)制备经式-三[1-苯基-3-(2’-丙基)苯并咪唑-2-亚基-C2,C2′]-铱(III)
卡宾配合物通过使在步骤b)中得到的咪唑鎓盐与[(μ-Cl)(η4-1,5-cod)Ir]2根据上述通用方法反应而制备。在进行柱色谱提纯之后,以理论产率的83%得到作为白色粉末的产物。
1H NMR(CD2Cl2,500MHz):δ=8.16(m,3H,CHPh),7.86(d, 3JH,H=7.9Hz,1H,CHPh),7.79(d,3JH,H=8.0Hz,2H,CHPh),7.45(m,3H,CHPh),7.28(m,3H,CHPh),7.18(m,3H,CHPh),6.95(m,4H,CHPh),6.67(m,1H,CHPh),6.60(m,4H,CHPh),4.81(m,1H,CHiPr),4.75(m,1H,CHiPr),4.67(m,1H,CHiPr),1.60(d,3JH,H=7.0Hz,3H,CH3),1.30(d, 3JH,H=7.0Hz,3H,CH3),1.22(d,3JH,H=7.2Hz,3H,CH3),0.82(d,3JH,H=7.0Hz,3H,CH3),0.61(d,3JH,H=7.0Hz,3H,CH3),0.55(d,3JH,H=7.3Hz,3H,CH3)。
13C NMR(CD2Cl2,125MHz):δ=189.1,185.8,184.7(NCN),151.7,150.7,149.8,149.1,148.5,148.4(Cq),139.1,137.5,137.1(CHPh),134.0,133.87,133.86,133.79,133.77,133.32(Cq),124.8,124.5,124.2,122.64,122.59,122.58,121.59,121.56,121.4,120.9,120.5,120.3,112.9,112.7,112.4,112.3,112.1(强度加倍),111.8,111.7,111.4(CHPh),53.5,51.7,51.6(CHiPr),21.0,20.5,20.2,20.1,20.0,19.9(CH3)。
实施例12:制备铱-卡宾配合物
(″Ir(pombic)3″)
a)制备2-[(2,6-二硝基苯基)氨基]苯酚(根据F.Ullmann,G.Engi,N.Wosnessenky,E.Kuhn和E.Herre,Liebigs Ann.365(1909)79,110)
将17.30g(157mmol)99%2-氨基苯酚和17.15g(209mmol)无水乙酸钠在氮气和搅拌下加入25.0g(121mmol)98%2,6-二硝基氯苯在185ml无水乙醇中的溶液中。将反应溶液加热至沸腾并回流2小时,然后冷却至室温。借助黑带过滤器(black-band filter)移出红紫色针状晶体,并用水洗涤直至流出液无色并在50℃和减压下干燥。得到27.90g(理论值的84%)黑色光泽的针状体,其在189-192℃(文献:191℃)熔融。
b)制备4-硝基吩噁嗪(根据F.Ullmann,G.Engi,N.Wosnessenky,E.Kuhn和E.Herre,Liebigs Ann.365(1909)79,110)
将27.70g(101mmol)2-[(2,6-二硝基苯基)氨基]苯酚在回流和搅拌下在666ml 1%NaOH中加热30分钟。在冷却至室温之后,吸滤固体并用热水洗涤至中性并在80℃和减压下干燥。得到21.2g(理论值的92%)黑色晶体,其在168-171℃(文献:166℃)熔融。
将21.20g(92.9mmol)1-硝基吩噁嗪悬浮在177ml无水乙醇中并与83.84g(372mmol)氯化锡(II)·2H2O在101ml浓HCl中的溶液混合。将反应混合物加热至沸腾并回流1小时。在将反应混合物冷却至室温之后,将沉淀吸滤,总共用430ml 10%HCl洗涤4次,然后用冷水洗涤并在70℃和减压下干燥。得到18.45g灰色针状体。
d)制备2,10b-二氮杂-6-氧杂醋蒽烯(咪唑[4,5,1-k,l]吩噁嗪;基于H.Shirai和T.Hayazaki,Yakugaku Zasshi 90(1970)588-593和A.N.Gritsenko,Z.I.Ermakova,V.S.Troitskaya和S.V.Zhuravlev.,Chem.Heterocycl.Compd.1971,715-717)
将18.45g(78.6mmol)1-氨基吩噁嗪氯化物悬浮于85ml 85%甲酸中。在加入5.38g(78.6mmol)甲酸钠之后,将反应混合物加热至沸腾并回流3.5小时。在冷却至室温之后,将反应混合物在700g 10%NaOH中沉淀并再搅拌30分钟。借助黑带过滤器吸滤固体,并用水洗涤并在70℃和减压下干燥。将粗产物(16.35g)在160ml甲醇中搅拌2小时,然后吸滤,用甲醇洗涤并在70℃干燥。得到13.09g(理论值的80%)灰色针状体,其在177-181℃(文 献:177-178℃)熔融。
e)制备10b-氮杂-2-氮鎓-2-甲基-6-氧杂醋蒽烯碘化物(碘化2-甲基咪唑[4,5,1-k,l]吩噁嗪鎓;基于H.Shirai和T.Hayazaki,Yakugaku Zasshi90(1970)588-593)
将5.48g(26.3mmol)2,10b-二氮杂-6-氧杂醋蒽烯和18.42g(130mmol)碘甲烷在75ml二氯甲烷中的溶液加热至沸腾并回流26小时。在将反应混合物冷却至室温之后,将固体吸滤,用二氯甲烷洗涤并在75℃和减压下干燥。得到8.35g(理论值的91%)分析纯的灰色微晶,其在284-291℃(文献:295-297℃)熔融。
f)制备10b-氮杂-2-氮鎓-2-甲基-6-氧杂醋蒽烯四氟硼酸盐(2-甲基咪唑[4,5,1-k,l]吩噁嗪鎓四氟硼酸盐)
将7.55g(50.0mmol)98%三甲基氧鎓四氟硼酸盐加入10.41g(50.0mmol)2,10b-二氮杂-6-氧杂醋蒽烯在620ml无水二氯甲烷中的溶液中,其中所述溶液用冰浴冷却至0-3℃。然后将反应混合物温热至室温并搅拌过夜。然后加入0.755g(5.0mmol)98%三甲基氧鎓四氟硼酸盐。在室温下搅拌4小时之后,将沉淀吸滤,用二氯甲烷洗涤并在40℃和减压下干燥(粗产量:11.35g)。将固体在氮气下从1000ml甲醇中再结晶。得到8.90g熔点为230-238℃的分析纯的深灰色微晶。将滤液浓缩至干。将固体(3.39g)从132ml甲醇中再结晶。得到1.42g深灰色微晶,即总共10.32g(理论值的67%)。
1H NMR(500MHz,DMSO):δ=4.10(s,3H),7.18(d,1H),7.37-7.61(m,5H),7.93(d,1H),10.25(s,1H)。
g)制备Ir(pombic)3
卡宾配合物通过使在步骤f)中得到的咪唑鎓盐与 [(μ-Cl)(η4-1,5-cod)Ir]2根据上述通用方法反应而制备。在进行柱色谱提纯之后,以理论产率的21%得到作为淡黄色粉末的经式异构体。
1H NMR(CD2Cl2,500MHz):δ=6.99(m,3H,CHPh),6.78(m,3H,CHPh),6.63(m,8H,CHPh),6.52(m,3H,CHPh),6.41(m,1H,CHPh),3.47(s,3H,CH3),3.45(s,3H,CH3),3.33(s,3H,CH3)。
13C NMR(CD2Cl2,125MHz):δ=170.18,168.16,166.87(NCN),145.08,144.61,144.42,144.34,144.01,143.49,143.45,143.44,142.31,136.29(Cq),136.25(CHPh),136.18,135.98(Cq),135.79,133.76(CHPh),131.92,131.24,130.51(Cq),126.61,126.48,126.43,125.51,125.34,125.28(CHPh),124.03,124.01,123.92(Cq),109.86,109.79,109.47,106.46,106.32,106.27,105.50,105.49,105.46(CHPh),33.98,33.64,33.55(CH3)。
实施例13:制备铱-卡宾配合物
(″Ir(psmbic)3″)
a)制备1-硝基吩噻嗪(除所用溶剂外,根据H.L.Sharma等,Tetrahedron Lett.1657-1662,1967)
将19.2g(0.15mol)98%2-巯基苯胺和41.0g(0.50mol)无水乙酸钠在氮气下加入20.7g(0.10mol)98%2,6-二硝基氯苯在300ml无水二甲基甲酰胺中的溶液中。将反应溶液加热至沸腾并回流12小时,然后冷却至室温。将所形成的沉淀吸滤,用水10%HCl和50%冰冷的乙醇洗涤并在40℃和减压下干燥。得到4.09g固体。将母液浓缩至干。将残留物用水洗涤并在减压下干燥(19.50g)。根据薄层色谱法,两种固体以高纯度包含所需产物,因而将两种固体合并。粗产量:23.6g(理论值的97%)。
b)制备1-铵基吩噻嗪氯化物(类似于在F.Kehrmann和L. Ber.dtsch.chem.Ges.44(1911)3006-3011中制备1-氨基吩噁嗪)
将23.6g(96.6mmol)1-硝基吩噻嗪悬浮于200ml无水乙醇中并与87.2g(387mmol)氯化锡(II)·2H2O在100ml浓HCl中的溶液混合。将反应混合物在回流下加热至沸腾直至硝基化合物固体消失,相反浅色的沉淀已沉积。在将反应混合物冷却之后,将沉淀吸滤,用水洗涤并在减压下干燥。粗产量:18.3g(理论值的76%)。
c)制备6-硫杂-2,10b-二氮杂醋蒽烯(咪唑[4,5,1-k,l]吩噻嗪;基于A.N.Gritsenko等,Chem.Heterocycl.Compd.1971,715-717.)
将18.3g(73.0mmol)1-氨基吩噻嗪氯化物悬浮于80ml 85%甲酸中,在加入5.81g(85mmol)甲酸钠之后,将反应混合物加热至沸腾并回流4小时。在冷却至室温之后,将沉淀吸滤,用水洗涤并在减压下干燥。粗产量:14.1g(理论值的86%)。
d)制备2-甲基-6-硫杂-10b-氮杂-2-氮鎓醋蒽烯四氟硼酸盐
6-硫杂-2,10b-二氮杂醋蒽烯与碘甲烷的甲基化反应已由Z.I.Ermakova等,Chem.Heterocycl.Compd.1974,324-326描述。
将8.41g(55.0mmol)98%三甲基氧鎓四氟硼酸盐加入12.43g(55.0mmol)6-硫杂-2,10b-二氮杂醋蒽烯在800ml无水二氯甲烷中的溶液中,所述溶液用冰浴冷却至3℃。使所述反应混合物温热至室温并搅拌过夜。将沉淀吸滤并用二氯甲烷洗涤并在40℃和减压下干燥(粗产量:12.37g)。将固体分别从200ml和175ml乙酸中再结晶两次。得到7.24g(理 论值的40%)熔点为223-224℃的浅褐色微晶。
e)制备Ir(psmbic)3
卡宾配合物通过使在步骤d)中得到的咪唑鎓盐与[(μ-Cl)(η4-1,5-cod)Ir]2根据上述通用方法反应而制备。在进行柱色谱提纯之后,以理论产率的29%得到作为浅黄色粉末的经式异构体。
1H NMR(CD2Cl2,500MHz):δ=6.99(m,3H,CHPh),6.78-6.52(m,14H,CHPh),6.42(m,1H,CHPh),3.36(s,3H,CH3),3.29(s,3H,CH3),3.25(s,3H,CH3)。
13C NMR(CD2Cl2,125MHz):δ=177.7,175.3,174.6(NCN),147.4,145.7,144.1(Cq),139.0(Cq),138.5(CH),138.3(Cq),138.2(CH),137.5(Cq),136.3(CH),134.5,134.4,133.9,129.5,129.4,129.3(Cq),125.0,124.9,124.8(CH),120.3,120.29,120.1(Cq),119.2,118.9,118.7(CH),117.1,116.7,116.4(Cq),116.4,116.38,116.31,107.05,107.03,106.99(CH),33.8,33.6,33.0(CH3)。
实施例14:制备[1-(4’-氰基苯基)-3-甲基咪唑-2-亚基-C2,C2′]铂(II)乙酰丙酮化物
(″Pt(cn-pmic)(acac)″)
a)制备1-(2-溴-4-氰基苯基)咪唑
将3-溴-4-氟苄腈(10.0g,50mmol,1当量)和咪唑(5.1g,75mmol,1.5当量)溶于二甲基甲酰胺(100ml)中并在氮气和室温下与氢化钠(60%,在矿物油中,3.0g,75mmol,1.5当量)小心混合。将混合物在100℃下搅拌4小时。在冷却至室温之后,加入水(10ml)并将混合物浓缩至干。将残留物用水和石油醚洗涤并通过柱色谱(硅胶,梯度的甲基叔丁基醚-乙酸乙酯)提纯。产量:5.4g(22mmol,44%)。
1H NMR(CD2Cl2,400MHz):δ=7.15(mc,1H),7.52(mc,1H),7.74(d, J 8.0,1H),7.99(mc,1H),8.06(dd,J 8.0,2.0,1H),8.48(d,J 2.0,1H)。
b)制备碘化1-(2-溴-4-氰基苯基)-3-甲基咪唑鎓
将1-(2-溴-4-氰基苯基)咪唑(5.4g,22mmol,1当量)和碘甲烷(15.4g,109.0mmol,5当量)溶于四氢呋喃(50ml)中并在室温下搅拌16小时。将所形成的沉淀过滤并用乙醇洗涤。产量:6.7g(17mmol,78%)
1H NMR(d6-DMSO/CD2Cl2 1∶1,400MHz):δ=4.17(s,3H),7.77(t,J2.0,1H),7.90(t,J 2.0,1H),7.96(dd,J 8.0,2.0,1H),8.16(d,J 8.0,1H),8.20(d,J 2.0,1H),9.96(s,1H)。
c)制备Pt(cn-pmic)(acac)
将1当量碘化1-(2-溴-4-氰基苯基)-3-甲基咪唑鎓在二噁烷中的悬浮液在氩气下与1当量双(三甲基甲硅烷基)氨化钾(0.5M,在甲苯中)缓慢混合,并且室温下搅拌30分钟。将混合物与1当量1,5-环辛二烯铂(II)二氯化物混合并在回流下搅拌16小时。在冷却至室温之后,将混合物浓缩至干。将残留物在二甲基甲酰胺中处理并与4当量2,4-戊二酮和4当量叔丁醇钾混合。将混合物在室温下搅拌16小时并在100℃下搅拌6小时。在冷却至室温后,将混合物浓缩至干并用水洗涤残留物。在柱色谱提纯之后,以理论产率的53%得到作为浅黄色粉末的产物。
1H NMR(d6-DMSO,400MHz):δ=1.97(s,3H),2.04(s,3H),4.01(s,3H),5.64(s,1H),7.45(d,J 2.0,1H),7.48(s,1H),7.51(d,J 1.5,1H),7.78(d,J 1.5,1H),8.06(d,J 2.0,1H)。
CI-MS(MeCN/H2O 8∶2):m/z=476(M+H+,校正同位素谱图)。
实施例15:制备三[1-(4’-氰基苯基)-3-甲基咪唑-2-亚基-C2,C2′]-铑(III)
(″Rh(cn-pmic)3″)
首先将6.31g(20.3mmol)碘化咪唑鎓(根据实施例1b制备))装入100ml 甲苯中。在室温下,经30分钟加入40.6ml双(三甲基甲硅烷基)氨化钾(0.5M,在甲苯中,20.3mmol)并将混合物搅拌1小时。将1.00g(2.0mmol)[(μ-Cl)Rh(η4-1,5-cod)]2溶于50ml甲苯中,并将混合物在室温下在30分钟内与盐混合物滴加混合。将反应混合物在室温下搅拌1小时,在70℃下搅拌2小时,然后在回流下搅拌过夜。将混合物浓缩至干。用二氯甲烷萃取残留物并通过柱色谱提纯萃取物。得到0.26g浅黄色粉末(10%)。
1H NMR(CD2Cl2,500MHz):δ=7.56(d,J=1.9Hz,1H),7.55(d,J=2.0Hz,1H),7.49(d,J=1.9Hz,1H),7.27-7.11(m,6H),6.97,6.93(各为s,1H),6.89(d,J=1.8Hz,1H),6.86(d,J=1.7Hz,2H),6.71(s,1H),3.03(s,6H,CH3),2.96(s,3H,CH3)。
13C NMR(CD2Cl2,125MHz):δ=190.3(d,1JC,Rh=38.4Hz,NCN),189.5(d,1JC,Rh=38.1Hz,NCN),188.2(d,1JC,Rh=38.3Hz,NCN),166.7(d, 1JC,Rh=27.5Hz,Cq),166.0(d,1JC,Rh=24.5Hz,Cq),164.5(d,1JC,Rh=24.4Hz,Cq),150.5,150.0,149.3(Cq),142.4,142.2,140.4,126.5,126.4,126.3,123.0,122.8,122.5,114.72,114.68,114.6,110.9,110.7,110.4(CHPh,NCHCHN),120.9(强度加倍,Cq),120.8(Cq),107.6(d,J=1.8Hz,Cq),107.2(d,J=1.9Hz,Cq),107.2(d,J=1.6Hz,Cq),37.3,37.2,36.1(CH3)。
实施例16:制备面式-三[1-(4’-氰基苯基)-3-甲基咪唑-2-亚基-C2,C2′]铱(III)
在实施例1中得到的面式/经式异构体混合物可通过柱色谱在硅胶上并用9∶1的乙酸乙酯/环己烷或者通过从乙腈中分级沉淀而分离成面式-和经式异构体。此处通常观察到约1∶19的面式/经式异构体比例。
将纯的经式-三[1-(4’-氰基苯基)-3-甲基亚咪唑基-C2,C2′]-铱(III)(20mg,27μmol)在丙酮(9.75ml)中的溶液在室温下与0.1M盐酸(0.25ml)混合。将混合物在回流下搅拌4小时。随后,在旋转蒸发器上除去挥发性组分以得到面式/经式异构体比例为约3∶1的异构体混合物,可将其如上所述分离。
面式-异构体分析:
1H NMR(d6-DMSO/CD2Cl2 4∶1,500MHz):δ=3.06(s,9H),6.66(d,J2.0,3H),7.11(d,J 2.0,3H),7.28(dd,J 8.0,2.0,3H),7.49(d,J 8.0, 3H),7.87(d,J 2.0,3H)。
13C NMR(d6-DMSO/CD2Cl2 4∶1,500MHz):δ=36.2,107.0,111.1,115.5,120.7,122.4,125.9,139.7,149.2,151.5,174.6。
ESI-MS(MeCN/H2O 8∶2):m/z=737.1751(M+,校正同位素谱图,计算:737.1755),755(M+NH4 +,校正同位素谱图)。
实施例17:生产OLED
用作阳极的ITO基材首先用LCD生产用市售洗涤剂(Deconex20NS和25ORGAN-ACID中和剂)清洁,然后在超声浴中在丙酮/异丙醇混合物中清洁。为了除去可能的有机残余物,再在臭氧箱中将基材暴露于连续的臭氧流25分钟。该处理也改善了该ITO的空穴注入。
然后通过在约2nm/min的速率和约10-7毫巴下的气相沉积将下述有机材料施用于已清洁的基材上。作为空穴导体和激子阻挡层,首先以30nm的层厚将化合物C1施用至基材。
然后通过气相沉积以20nm的厚度施用30重量%来自实施例3的化合物Ir(cn-pmbic)3:
和70重量%化合物C3的混合物:
(C3通过本领域技术人员已知的酯合成方法制备;关于该主题,还参见在先德国专利申请10 2005 014284.2),Ir(cn-pmbic)3用作发光剂,C3用作基体材料。然后通过气相沉积施用厚度为4nm的C2空穴阻挡剂层。
然后通过气相沉积施用厚度为30nm的TPBI[2,2’,2”-(1,3,5-苯三基)三(1-苯基苯并咪唑)]电子传导剂层,1nm厚的氟化锂层,最后是110nm厚的Al电极。
为了表征该OLED,在各种电流和电压下记录电致发光光谱。此外,结合发光输出测量电流-电压特性。通过用光度计校准可以将光输出转化为光度参数。
对于所述OLED,得到下列电光数据:
最大发光波长 | 460nm |
CIE(x,y) | 0.150;0.126 |
光度效率 | 11.2cd/A(在4V下) |
功率系数 | 9.0lm/W |
外部量子产率 | 10.5% |
最大发光密度 | 900cd/m2 |
在甲苯中的PL测量在石英比色皿(10×10mm)中使用2mg/l的发光剂浓度进行。激发波长为325nm(HeCd激光)且在90°角下借助在二极管阵列分光光度计中的纤维镜片检测发光。
在PMMA中的PL测量使用2%的发光剂掺杂进行。它们按如下生产:将2mg/l发光剂溶于10%的PMMA二氯甲烷溶液(Mw 120kD)中并用60μm的刮刀刀涂于显微镜载玻片上。激发波长为325nm(HeCd激光);激发与显微镜载玻片呈直角且在45°角下借助在二极管阵列分光光度计中的纤维镜片检测发光。
对于所述OLED,得到下列电光数据:
最大发光波长 | 476nm |
CIE(x,y) | 0.21;0.30 |
光度效率 | 10.0cd/A |
功率系数 | 11.6lm/W |
外部量子产率 | 5.0% |
在100cd/m2发光密度下的光度效率 | 4.0cd/A |
最大发光密度 | 3500cd/m2 |
c)
ITO基材如a)所述进行预处理。
然后以46nm的厚度将PEDT:PSS(聚(3,4-亚乙二氧基噻吩)聚(苯乙烯磺酸盐))(BaytronP VP AI 4083)由水溶液旋涂于基材上并以约48nm的厚度由溶于氯苯中的PMMA(16.5mg PMMA/1ml氯苯)和发光剂物质1c)施用发光剂层。发光剂的浓度对应于PMMA的30重量%掺杂。然后通过气相沉积施用厚度为52.5nm的BCP的空穴阻挡剂和电子传导剂层,0.75nm厚的氟化锂层,最后是110nm厚的Al电极。
为了表征该OLED,在各种电流和电压下记录电致发光光谱。此外,结合发光输出测量电流-电压特性。通过用光度计校准可以将光输出转化为光度参数。
对于所述OLED,得到下列电光数据:
最大发光波长 | 460nm |
光度效率 | 4.3cd/A |
功率系数 | 1.1lm/W |
外部量子产率 | 3.5% |
在100cd/m2发光密度下的光度效率 | 1.2cd/A |
最大发光密度 | 150cd/m2 |
Claims (7)
1.通式I的不带电过渡金属-卡宾配合物在有机发光二极管中的用途:
其中各变量如下所定义:
M为选自Ir的金属原子,且Ir为具有配位数为6的Ir(III);
n为卡宾配体数目,其中n为3且式I配合物中的卡宾配体可以相同或不同;
Do为选自N的配位原子;
r为1;
Y1、Y2各自独立地为氢或烷基;
或
Y1和Y2与它们所键合的碳原子一起形成可以包含1个氮原子的6员芳族环;
Y3为氢或烷基;
A为具有3或4个原子的桥键,其中一个或两个原子可以为杂原子且剩余原子为碳原子,从而使基团
形成5或6员杂芳族环或苯环,所述环各自任选被选自如下的取代基取代:烷基、卤素、CN,
其中Y1与选自化学单键、C(Y4)2、C(O)、O、S、S(O)、SO2和NY5的基团一起可以任选形成2员桥键B,该桥键B连接于桥键A中位于与卡宾配体的卡宾单元的氮原子键合的碳原子的α位的碳原子或杂原子;Y4、Y5各自独立地为氢、烷基、芳基或杂芳基,且C(Y4)2桥中的两个Y4基团可以相互独立地变化。
2.根据权利要求1的式I的配合物的用途,其中
卡宾配体相同;
其中变量各自如权利要求1所定义。
3.一种制备根据权利要求1或2的式I的过渡金属-卡宾配合物的方法,其包括使对应于特定卡宾配体的配体前体脱去质子,然后或同时与包含所需金属的合适金属配合物反应。
4.一种OLED,其包含至少一种根据权利要求1或2的式I的过渡金属-卡宾配合物。
5.一种发光层,其包含至少一种根据权利要求1或2的式I的过渡金属-卡宾配合物。
6.一种包含根据权利要求5的发光层的OLED。
7.一种包含根据权利要求4或6的OLED的固定可视显示单元。
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DE102004057072A DE102004057072A1 (de) | 2004-11-25 | 2004-11-25 | Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs) |
PCT/EP2005/012529 WO2006056418A2 (de) | 2004-11-25 | 2005-11-23 | Verwendung von übergangsmetall-carbenkomplexen in organischen licht-emittierenden dioden (oleds) |
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CN (1) | CN101065389B (zh) |
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2004
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- 2005-11-23 DE DE502005007675T patent/DE502005007675D1/de active Active
- 2005-11-23 JP JP2007541832A patent/JP5001851B2/ja active Active
- 2005-11-23 US US11/720,291 patent/US20080018221A1/en not_active Abandoned
- 2005-11-23 KR KR1020077014428A patent/KR101290967B1/ko active IP Right Grant
- 2005-11-23 WO PCT/EP2005/012529 patent/WO2006056418A2/de active Application Filing
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2014
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US20240074302A1 (en) | 2024-02-29 |
DE102004057072A1 (de) | 2006-06-01 |
US20140309428A1 (en) | 2014-10-16 |
CN101065389A (zh) | 2007-10-31 |
WO2006056418A3 (de) | 2007-01-11 |
KR101290967B1 (ko) | 2013-08-20 |
DE502005007675D1 (de) | 2009-08-20 |
US20080018221A1 (en) | 2008-01-24 |
KR20070090953A (ko) | 2007-09-06 |
US11980086B2 (en) | 2024-05-07 |
US20200136064A1 (en) | 2020-04-30 |
ATE435867T1 (de) | 2009-07-15 |
EP1819717A2 (de) | 2007-08-22 |
WO2006056418A2 (de) | 2006-06-01 |
JP2008521946A (ja) | 2008-06-26 |
EP1819717B1 (de) | 2009-07-08 |
JP5001851B2 (ja) | 2012-08-15 |
US10522768B2 (en) | 2019-12-31 |
WO2006056418A8 (de) | 2007-03-01 |
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