CN103746080B - 发射磷光的二极管中的苯并[9，10]菲基质 - Google Patents
发射磷光的二极管中的苯并[9，10]菲基质 Download PDFInfo
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- CN103746080B CN103746080B CN201410037481.3A CN201410037481A CN103746080B CN 103746080 B CN103746080 B CN 103746080B CN 201410037481 A CN201410037481 A CN 201410037481A CN 103746080 B CN103746080 B CN 103746080B
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- Prior art keywords
- benzo
- emission layer
- phenanthrene compound
- phenanthrene
- phosphorus
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- 125000005605 benzo group Chemical group 0.000 title claims abstract description 151
- 125000005561 phenanthryl group Chemical group 0.000 title claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims abstract description 154
- -1 phenanthrene compound Chemical class 0.000 claims abstract description 83
- 239000003205 fragrance Substances 0.000 claims abstract description 77
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 24
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims description 101
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 36
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 35
- 229910052698 phosphorus Inorganic materials 0.000 claims description 33
- 239000011574 phosphorus Substances 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 31
- 229940049706 benzodiazepine Drugs 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 16
- 239000002131 composite material Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 239000000126 substance Substances 0.000 abstract description 14
- 230000003252 repetitive effect Effects 0.000 abstract description 11
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- 239000010410 layer Substances 0.000 description 146
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 229910052751 metal Inorganic materials 0.000 description 24
- 239000002184 metal Substances 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 239000000758 substrate Substances 0.000 description 24
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 22
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- 125000004429 atom Chemical group 0.000 description 6
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
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- 230000000694 effects Effects 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
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- 125000000623 heterocyclic group Chemical group 0.000 description 4
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- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 150000005360 2-phenylpyridines Chemical class 0.000 description 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- SCZWJXTUYYSKGF-UHFFFAOYSA-N 5,12-dimethylquinolino[2,3-b]acridine-7,14-dione Chemical compound CN1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3N(C)C1=C2 SCZWJXTUYYSKGF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
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- 201000001366 familial temporal lobe epilepsy 2 Diseases 0.000 description 3
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- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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- CKZBRKLFMRHHMA-UHFFFAOYSA-N 1,3-dimethoxy-2-phenylbenzene Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1 CKZBRKLFMRHHMA-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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- 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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- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
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- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K2019/328—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems containing a triphenylene ring system
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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Abstract
本发明提供了一种有机发射层。还被提供的是一种器件，其中所述有机发射层布置在阳极和阴极之间。所述有机发射层包括磷光性物质和苯并[9，10]菲化合物或具有含有苯并[9，10]菲部分的重复单元的化合物。苯并[9，10]菲是任选取代的。取代基可以相同或不同，各自选自由烷基、芳基、稠合芳基、取代的芳基、烯基、炔基和杂烷基组成的组。本发明也提供了苯并[9，10]菲化合物。
Description
发明领域
本发明涉及有机发光器件(OLED)，具体地说，涉及用于这样的器件中的磷光性有机材料。更具体地说，本发明涉及结合进OLED中的苯并[9，10]菲化合物。
背景技术
利用有机材料的光电器件由于许多理由越来越为人们所需求。用于制造此类器件的许多材料是相对便宜的，因此有机光电器件具有在成本上比无机器件有优势的可能。另外，有机材料的固有性能如它们的柔性可以使得它们非常适合于特殊应用，如在柔性基材上制造。有机光电器件的实例包括有机发光器件(OLED)、有机光敏晶体管、有机光生伏打电池和有机光检测器。对于OLED，有机材料可以比常规材料有性能优势。例如，有机发射层发光的波长一般可以容易地用合适的掺杂剂调节。
在这里使用的术语“有机”包括可用来制造有机光电器件的聚合物材料以及小分子有机材料。“小分子”指不是聚合物的任何有机材料，并且“小分子”实际上可以是相当大的。在一些情况下小分子可以包括重复单元。例如，使用长链烷基作为取代基不会将一个分子从“小分子”类型中排除。小分子也可以被引入聚合物中，例如作为在聚合物骨架上的侧基或作为骨架的一部分。小分子也可以用作树状分子的芯结构部分，该树状分子由在芯结构部分上构建的一系列化学壳组成。树状分子的芯结构部分可以是荧光或磷光小分子发射体。树状分子可以是“小分子”，并且据信目前在OLED领域中使用的所有树状分子是小分子。通常，小分子具有明确定义的、有单一分子量的化学式，而聚合物的化学式和分子量在分子与分子之间可以不同。
OLED利用薄的有机膜，当对器件施加电压时所述有机膜会发光。OLED正在成为人们越来越感兴趣的技术，用于诸如平板显示器、照明和逆光照明之类的应用中。几种OLED材料和构造已被描述在美国专利5,844,363、6,303,238和5,707,745中，它们的全部内容通过引用结合在本文中。
OLED器件一般(但并不总是)意图通过电极中的至少一个发光，并且一个或多个透明电极可能被用于有机光电器件。例如，透明电极材料，如氧化铟锡(ITO)，可以被用作底部电极。还可以使用透明顶部电极，如在美国专利5,703,436和5,707,745中公开的透明顶部电极，所述美国专利的全部内容通过引用结合在本文中。对于打算仅通过底部电极发光的器件，顶部电极不需要是透明的，并且可以由具有高导电性的、厚的并且反射性的金属层组成。类似地，对于打算仅通过顶部电极发光的器件，底部电极可以是不透明的和／或反射性的。当一个电极不需要是透明的时，使用较厚的层可提供更好的导电性，并且使用反射性电极可以通过将光反射回透明电极来增加通过所述另一电极发射的光的量。也可以制造完全透明的器件，其中两个电极都是透明的。还可以制造侧边发射的OLED，并且在此类器件中一个或两个电极可以是不透明的或反射性的。
在这里使用的“顶部”指最远离基材，而“底部”指最接近基材。例如，对于具有两个电极的器件，底部电极是最接近基材的电极，并且一般是所制造的第一个电极。底部电极有两个表面，即最接近基材的底面和远离基材的顶面。当第一层被描述为“布置在”第二层上，所述第一层远离基材来设置。在所述第一和第二层之间还可以有其它层，除非规定所述第一层与所述第二层“物理接触”。例如，阴极可以被描述为“布置在”阳极上，即使在两者之间有各种有机层。
在这里使用的“可溶液处理的”是指能够在液体介质中溶解、分散或输送和／或从液体介质中沉积，无论呈溶液或悬浮液的形式。
如本领域技术人员通常理解的，在这里使用时，第一“最高已占分子轨道”(HOMO)或“最低未占分子轨道”(LUMO)能级“大于”或“高于”第二HOMO或LUMO能级，如果所述第一能级更接近于真空能级。因为电离电位(IP)是作为相对于真空能级的负能量来测量的，较高的HOMO能级对应于具有较小绝对值的IP(较小负性的IP)。类似地，较高的LUMO能级对应于具有较小绝对值的电子亲合势(EA)(较小负性的EA)。在真空能级在顶部的普通的能级图上，材料的LUMO能级高于同一材料的HOMO能级。“较高的”HOMO或LUMO能级比“较低的”HOMO或LUMO能级更接近于这样的图的顶部。
发明概述
本发明涉及可用于磷光性有机发光二极管中的苯并[9，10]菲化合物。具体的实例包括多芳基取代的苯并[9，10]菲，例如六芳基苯并[9，10]菲，1，1-联苯并[9，10]菲，2，2-联苯并[9，10]菲，1，12-稠合的二苯并[9，10]菲，2，3-稠合的四苯并[9，10]菲，和亚芳基苯并[9，10]菲苯并[9，10]菲。优点是高三重态能量，还有高π-共轭作用。证实了具有苯并[9，10]菲基质的、高效率和稳定性的PHOLED。某些高三重态能量的类似物预计可以与深蓝色磷光掺杂剂一起使用。
提供了有机发光器件中的发射层。该发射层包括磷光物质和苯并[9，10]菲化合物。优选地，所述苯并[9，10]菲化合物具有比磷光物质的HOMO和LUMO能级之间的能隙大的HOMO和LUMO能级之间的能隙。
在一个优选实施方案中，发射层中的苯并[9，10]菲化合物具有至少大约1.8eV的其HOMO能级和其LUMO能级之间的能隙。
在另一个实施方案中，所述苯并[9，10]菲化合物具有比磷光物质的最高已占分子轨道低的最高已占分子轨道。
在另一个实施方案中，所述苯并[9，10]菲化合物具有比磷光物质的最低未占分子轨道高的最低未占分子轨道。
在一个实施方案中，所述发射层包括磷光物质和苯并[9，10]菲化合物，其中所述苯并[9，10]菲化合物具有下式：
其中各R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12独立地是H或选自由如下基团组成的组的取代基：芳基，取代的芳基，杂芳基，取代的杂芳基，烷基，芳烷基(arylkyl)杂烷基，烯基和炔基，并且其中所述苯并[9，10]菲化合物具有至少两个取代基。优选地，所述苯并[9，10]菲化合物具有小于1400的分子量。在一些优选实施方案中，R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12中的至少一个选自芳基和取代的芳基。在另一个实施方案中，R2、R3、R6、R7、R10和R11中的每一个选自芳基和取代的芳基；在又一个实施方案中，R2、R3、R6、R7、R10和R11中的每一个选自芳基和取代的芳基，并且R2、R3、R6、R7、R10和R11全部相同。
在另一个实施方案中，发射层包括磷光物质和具有重复单元的化合物，所述重复单元含有苯并[9，10]菲部分。
在另一个实施方案中，发射层包括磷光物质和具有苯并苯并[9，10]菲结构的苯并[9，10]菲化合物。
在另一个实施方案中，发射层包括磷光物质和具有稠合的苯并[9，10]菲结构的苯并[9，10]菲化合物。
还提供了有机场致发光器件。该器件包括阳极、阴极和在阳极和阴极之间的发射层，该发射层包括苯并[9，10]菲物质和磷光物质。所述苯并[9，10]菲物质可以是稠合的苯并[9，10]菲、苯并苯并[9，10]菲或具有下式的苯并[9，10]菲化合物：
其中R1-R3各自独立地是H或选自由下列基团组成的组的取代基：芳基，取代的芳基，杂芳基，取代的杂芳基，烷基，芳烷基，杂烷基，烯基和炔基。优选地，所述苯并[9，10]菲化合物具有至少两个取代基和小于1400的分子量。
还提供的是有机场致发光器件，该器件包括阳极、阴极和在阳极和阴极之间的发射层，该发射层包括磷光物质和具有重复单元的化合物，所述重复单元含有苯并[9，10]菲部分。
附图的简要说明
图1显示了一种具有单独的电子传输层、空穴传输层和发射层以及其它层的有机发光器件。
图2显示了一种颠倒的有机发光器件，其不具有单独的电子传输层。
图3显示了HPT：Ir(3-Mepq)2(acac)器件的发光效率与发光度的关系。
图4显示了HPT：Ir(3-Mepq)2(acac)器件的电流密度与电压的关系。
图5显示了HPT：Ir(3-Mepq)2(acac)器件的寿命。
图6显示了HPT：Ir(1-piq)3的发光效率与发光度的关系。
图7显示了HPT：Ir(1-piq)3器件的电流密度与电压的关系。
图8显示了HPT：Ir(1-piq)3器件的寿命。
图9显示了Ir(5-Phppy)3器件的发光效率与发光度的关系。
图10显示了Ir(5-Phppy)3器件的电流密度与电压的关系。
图11显示了2，2-联苯并[9，10]菲(2，2-BT)Ir(3-Mepq)2(acac)器件的发光效率与发光度的关系。
图12显示了2，2-BT：Ir(3-Mepq)2(acac)的电流密度与电压的关系。
图13显示了2，2-BT：Ir(3-Mepq)2(acac)器件的寿命。
图14显示了2，2-BT：Ir(1-piq)3器件的发光效率与发光度的关系。
图15显示了2，2-BT：Ir(1-piq)3器件的电流密度与电压的关系。
图16显示了2，2-BT：Ir(1-piq)3器件的寿命。
图17显示了HPT、2，2-BT、1，1-BT、1，1-稠合的BT、1，12-稠合的TT、2-乙烯基苯并[9，10]菲和4-叔丁基-HPT的化学结构。
图18显示了2，2-BT：Ir(pq)2(acac)器件的组成。
图19显示了2，2-BT：Ir(pq)2(acac)器件的发光效率与发光度的关系。
图20显示了2，2-BT：Ir(pq)2(acac)器件的电流密度与电压的关系。
图21显示了在10mA／cm2条件下2，2-BT：Ir(pq)2(acac)器件的EL和CIE。
图22显示了2，2-BT：Ir(pq)2(acac)器件的寿命。
图23显示了2，2-BT：Ir(5-Phppy)3器件的发光效率与发光度的关系。
图24显示了2，2-BT：Ir(5-Phppy)3器件的电流密度与电压的关系。
图25显示了在10mA／cm2条件下2，2-BT：Ir(5-Phppy)3器件的EL和CIE。
图26显示了2，2-BT：Ir(5-Phppy)3器件的寿命。
图27显示了H1NT：Ir(pq)2(acac)和H2BT：Ir(3-Meppy)3器件的组成。
图28显示了H1NT：Ir(pq)2(acac)和H2BT：Ir(3-Meppy)3器件的发光效率与发光度的关系。
图29显示了H1NT：Ir(pq)2(acac)和H2BT：Ir(3-Meppy)3器件的电流密度与电压的关系。
图30显示了在10mA／cm2条件下H1NT：Ir(pq)2(acac)和H2BT：Ir(3-Meppy)3器件的EL和CIE。
图31显示了H1NT：Ir(pq)2(acac)和H2BT：Ir(3-Meppy)3器件的寿命。
详细说明
一般地，OLED包括布置在阳极和阴极之间并且电连接到阳极和阴极上的至少一个有机层。当施加电流时，阳极注入空穴和阴极注入电子到所述有机层中。注入的空穴和电子各自向着带相反电荷的电极迁移。当电子和空穴定域在同一分子上时，形成了“激子”，所述激子是具有激发能态的定域的电子-空穴对。当激子通过光发射机理松驰时，光被发射。在一些情况下，所述激子可以定域在受激准分子或激态复合物上。非辐射机理如热弛豫也可能发生，但一般被认为是不希望的。
最初的OLED采用从发射分子的单线态发光(“荧光”)的发射分子，被公开在例如美国专利No.4,769,292中，该专利全部内容通过引用结合到本文中。荧光发射通常在小于10毫微秒的时间范围内发生。
最近，已经证实了具有从三重态发光(“磷光”)的发射材料的OLED。Baldo等人，“Highly Efficient Phosphorescent Emission from Organic ElectroluminescentDevices”，Nature，395卷，151-154，1998(“Baldo-I”)；和Baldo等人，“Very high-efficiency green organic light-emitting devices based on electrophosphorescence”，Appl.Phys.Lett.，75卷，No.3，4-6(1999)(“Baldo-II”)，它们的全部内容通过引用结合在本文中。磷光可以被称为“受禁”跃迁，因为该跃迁要求自旋状态的改变，并且量子力学指出这样的跃迁不是有利的。结果，磷光一般在超过至少10毫微秒，典型地大于100毫微秒的时间范围内发生。如果磷光的自然辐射寿命太长，则三重态可能通过非辐射机理衰减，这样没有光被发射。在非常低的温度下，在含有具有未共享电子对的杂原子的分子中也常常观察到有机磷光。2，2’-联吡啶是这样的分子。非辐射衰减机理典型地是温度依赖性的，这样在液态氮温度下显示磷光的有机材料典型地在室温下不显示磷光。但是，如Baldo所证明的，这一问题可以通过选择在室温下发磷光的磷光化合物来解决。代表性的发射层包括掺杂或未掺杂的磷光有机金属材料，例如在美国专利6,303,238和6,310,360；美国专利申请出版物2002-0034656；2002-0182441；2003-0072964；和WO-02／074015中所公开的。
一般地，在OLED中的激子被认为是以约3：1的比率产生，即大约75％三重态和25％单线态。参见Adachi等人，“Nearly100％Internal Phosphorescent Efficiency In AnOrganic Liht Emitting Device”，J.Appl.Phys.，90，5048(2001)，它的全部内容通过引用结合在本文中。在很多情况下，单线态激子可以容易地通过“系统间穿越(intersystemcrossing)”将它们的能量转移到三重激发态，而三重态激子不能够容易地将它们的能量转移到单线激发态。结果，采用磷光OLED，100％的内量子效率在理论上是可能的。在荧光器件中，三重态激子的能量一般损失到加热该器件的无辐射衰变过程，导致低得多的内量子效率。利用从三重激发态发射的磷光材料的OLED被公开在例如美国专利6,303,238中，它的全部内容通过引用结合在本文中。
从三重激发态到中间的非三重态的跃迁可以先于磷光发射，从所述非三重态发生发射衰减。例如，配位于镧系元素上的有机分子常常从定域在镧系金属上的激发态发射磷光。然而，这样的材料不直接从三重激发态发射磷光，而是从以镧系金属离子为中心的原子激发态发射。铕二酮化物络合物举例说明了一组这些类型的物质。
相对于荧光来说，通过将有机分子束缚(优选通过键接)在高原子序数的原子近处可以增强来自三重态的磷光。这一被称作重原子效应的现象是通过被称为自旋轨道耦合的机理产生的。这样的磷光跃迁可以从有机金属分子如三(2-苯基吡啶)铱(III)的已激发的金属到配位体电荷转移(MLCT)状态观察到。
在这里使用的术语“三重态能量”是指与在给定材料的磷光光谱中可辩别的最高能量特征相对应的能量。所述最高能量特征不必是在磷光光谱中具有最大强度的峰，并且它例如可以是在这样的峰的高能量侧的清楚肩部的局部最大值。
在这里使用的术语“有机金属”如本领域普通技术人员一般所理解的那样，并且如例如在“Inorganic Chemistry”(第二版)，Gary L.Miessler and Donald A.Tarr，Prentice Hall(1998)中所给出的含义。因此，所述术语有机金属指具有通过碳-金属键键接到金属上的有机基团的化合物。这一类型本质上不包括配位化合物，配位化合物是仅具有来自杂原子的给体键的物质，例如胺、卤化物、拟卤化物(CN等)和类似物的金属络合物。在实践中，除连接到有机物质上的一个或多个碳-金属键之外，有机金属化合物通常包括一个或多个来自杂原子的给体键。连接到有机物质上的碳-金属键指在金属和有机基团如苯基、烷基、烯基等的碳原子之间的直接的键，但不指连接到“无机碳”如CN或CO的碳上的金属键。
图1显示了有机发光器件100。这些图不一定按比例画出。器件100可包括基材110，阳极115，空穴注入层120，空穴传输层125，电子封闭层130，发射层135，空穴封闭层140，电子传输层145，电子注入层150，保护层155，和阴极160。阴极160是具有第一导电层162和第二导电层164的复合阴极。器件100可以通过按照顺序沉积所述层来制造的。
基材110可以是提供所需的结构性能的任何合适基材。基材110可以是柔性或刚性的。基材110可以是透明、半透明的或不透明的。塑料和玻璃是优选的刚性基材材料的例子。塑料和金属箔是优选的柔性基材材料的例子。基材110可以是半导体材料，以帮助电路的制造。例如，基材110可以是硅晶片(在它之上制造电路)，能够控制随后沉积在基材上的OLED。可以使用其它基材。可以选择基材110的材料和厚度，以获得所需的结构和光学性质。
阳极115可以是有足够的导电性以输送空穴到有机层中的任何合适阳极。阳极115的材料优选具有高于约4eV的功函数(“高功函数材料”)。优选的阳极材料包括导电性金属氧化物，如氧化铟锡(ITO)和氧化铟锌(IZO)，氧化锌铝(AlZnO)，和金属。阳极115(和基材110)可以是足够透明的，以制造底部发光的器件。一种优选的透明基材和阳极组合是可商购的、沉积在玻璃或塑料(基材)上的ITO(阳极)。柔性和透明的基材-阳极组合公开在美国专利No5,844,363和6,602,540B2中，它们的全部内容通过引用结合在本文中。阳极115可以是不透明的和／或反射性的。反射性阳极115对于一些顶部发光型器件可能是优选的，以增加从器件的顶部发射出的光量。可以选择阳极115的材料和厚度，以获得所需的导电性和光学性质。当阳极115是透明的时，对于一种具体的材料可能有一定的厚度范围，即厚度要足够厚以提供所需的导电性，同时要足够薄以提供所需的透明度。可以使用其它阳极材料和结构。
空穴传输层125可以包括能够传输空穴的材料。空穴传输层130可以是本征的(未掺杂的)，或者掺杂的。掺杂可以用于增强导电性。α-NPD和TPD是本征空穴传输层的例子。p-掺杂的空穴传输层的一个例子是按照50：1的摩尔比率掺杂了F4-TCNQ的m-MTDATA，如在Forrest等人的美国专利申请出版物No.2003-0230980中所公开的，该文献的全部内容通过引用结合在本文中。可以使用其它空穴传输层。
发射层135可以包括当有电流在阳极115和阴极160之间通过时能够发射光的有机材料。优选地，发射层135含有磷光发光材料，虽然荧光发光材料也可以使用。磷光材料因为与此类材料有关的更高发光效率而是优选的。发射层135还可以包括能够传输电子和／或空穴、掺杂了发光材料的基质材料，该发光材料可以捕获电子、空穴和／或激子，使得激子经由光发射机理从发光材料松驰。发射层135可以包括兼有传输和发光性能的单一材料。不论发光材料是掺杂剂或主要成分，发射层135可以包括其它材料，如调节发光材料的发射的掺杂剂。发射层135可以包括能够在组合时发射所需光谱的光线的多种发光材料。磷光发光材料的例子包括Ir(ppy)3。荧光发光材料的例子包括DCM和DMQA。OLED中的基质材料的例子包括Alq3，CBP和mCP。OLED中的发光和基质材料的例子公开在Thompson等人的美国专利No.6,303,238中，该专利的全部内容通过引用结合在本文中。在本发明中，优选的基质材料包括苯并[9，10]菲复合物。苯并[9，10]菲化合物在OLED的其它应用中是有用的材料，例如电子传输材料，如US US20050025993中所述。可以以许多方式将发光材料包括在发射层135中。例如，发光小分子可以被引入聚合物中。这可以通过几种方式来实现：通过将小分子作为单独的和不同的分子物种掺杂到聚合物中；或通过将小分子引入到聚合物的骨架中，以形成共聚物；或通过将小分子作为侧基键接在聚合物上。可以使用其它发射层材料和结构。例如，小分子发光材料可以作为树状分子的芯存在。
许多有用的发光材料包括键接于金属中心上的一个或多个配位体。如果配位体直接对有机金属发光材料的发光性能有贡献，配位体可以被称为“光活性的”。“光活性的”配位体与金属一起可以提供能级，在发射光子时电子从所述能级出来或进入所述能级。其它配位体可以被称为“辅助的”。辅助的配位体可以改变分子的光活性性能，例如通过使光活性配位体的能级发生位移，但是辅助的配位体不直接提供在光发射中直接牵涉到的能级。在一个分子中是光活性的的配位体在另一个分子中可以是辅助的。这些“光活性的”和“辅助的”的定义并不是限制性的理论。
电子传输层145可以包括能够传输电子的材料。电子传输层145可以是本征的(未掺杂的)，或者掺杂的。掺杂可以被用于增强导电性。Alq3是本征电子传输层的一个例子。n-掺杂的电子传输层的一个例子是按照1：1的摩尔比率掺杂了Li的BPhen，如在Forrest等人的美国专利申请出版物No.2003-0230980中所公开的，该文献的全部内容通过引用结合在本文者。可以使用其它电子传输层。
可以选择电子传输层的电荷携带组分，使得电子能够有效地从阴极注入到电子传输层的LUMO(最低未占分子轨道)能级。“电荷携带组分”是提供实际上传输电子的LUMO能级的材料。这一组分可以是基础材料，或者它可以是掺杂剂。有机材料的LUMO能级一般可以由该材料的电子亲合势来表征，而阴极的相对电子注入效率一般可以由阴极材料的功函数来表征。这意味着电子传输层和相邻的阴极的优选性能可以根据ETL的电荷携带组分的电子亲合势和阴极材料的功函数来确定。特别地，为了实现高的电子注入效率，阴极材料的功函数优选不比电子传输层的电荷携带组分的电子亲合势大大约0.75eV以上，更优选地，不比电子传输层的电荷携带组分的电子亲合势大大约0.5eV以上。类似的考虑适用于有电子注入其中的任何层。
阴极160可以是现有技术中已知的任何合适的材料或材料组合，使得阴极160能够传导电子和将电子注入器件100的有机层中。阴极160可以是透明的或不透明的，并且可以是反射性的。金属和金属氧化物是合适的阴极材料的例子。阴极160可以是单个层，或可以具有复合结构。图1显示了具有薄的金属层162和厚的导电性金属氧化物层164的复合阴极160。在复合阴极中，用于所述较厚层164的优选材料包括ITO，IZO和现有技术中已知的其它材料。美国专利No5,703,436，5,707,745，6,548,956B2和6,576,134B2(它们的全部内容通过引用结合在本文中)公开了包括复合阴极在内的阴极的例子，所述复合阴极具有金属如Mg：Ag的薄层，在所述金属薄层上具有层叠的透明的、导电的、溅射沉积的ITO层。阴极160的与下面的有机层接触的部分(不论它是单层阴极160、复合阴极的薄金属层162或一些其它部分)优选由具有小于约4eV的功函数的材料(“低功函数材料”)制成。可以使用其它阴极材料和结构。
封闭层可以用于减少离开发射层的电荷载流子(电子或空穴)和／或激子的数量。电子封闭层130可以布置在发射层135和空穴传输层125之间，以在空穴传输层125的方向上阻断电子离开发射层135。类似地，空穴封闭层140可以布置在发射层135和电子传输层145之间，以在电子传输层145的方向上阻断空穴离开发射层135。封闭层还可以用来阻断激子从发射层中扩散出来。封闭层的理论和使用更详细地描述在美国专利No.6,097,147和美国专利申请出版物No.2003-0230980(Forrest等人)，它们的全部内容通过引用结合在本文中。
在这里使用并且如本领域技术人员理解的，术语“封闭层”是指提供显著地抑制电荷载流子和／或激子传输通过器件的阻隔性层，但并不暗示该层必须完全地阻断电荷载流子和／或激子。这样的封闭层在器件中的存在可以导致比没有封闭层的类似器件明显更高的效率。同时，封闭层可以用来将发射限制到OLED的希望的区域中。
一般地，注入层是由可以改进电荷载流子从一层(如电极或有机层)注入到相邻有机层中的材料组成的。注入层也可以发挥电荷传输功能。在器件100中，空穴注入层120可以是改进空穴从阳极115注入空穴传输层125中的任何层。CuPc是可用作从ITO阳极115和其它阳极注射空穴的空穴注入层的材料的一个实例。在器件100中，电子注入层150可以是改进电子向电子传输层145中的注入的任何层。LiF／Al是可用作从相邻层中注射电子到电子传输层中的电子注入层的材料的一个实例。其它材料或材料组合可以用于注入层。取决于具体器件的构型，注入层可以被布置在与在器件100中所示的那些位置不同的位置。在美国专利申请序列号No.09／931,948(Lu等人)中提供了注入层的更多实例，所述文献的全部内容通过引用结合在本文中。空穴注入层可以包括溶液沉积的材料，如旋涂的聚合物，例如PEDOT：PSS，或者它可以是蒸气沉积的小分子材料，例如CuPc或MTDATA。
空穴注入层(HIL)可以平面化或润湿阳极表面，以提供从阳极到空穴注射材料中的有效的空穴注入。空穴注入层还可以含有电荷携带组分，该电荷携带组分具有的HOMO(最高已占分子轨道)能级有利地与在HIL的一侧上的相邻阳极层和在HIL的相对侧上的空穴传输层相匹配，如由它们的在这里所述的相对电离电位(IP)能量所定义的。该“电荷携带组分”是提供实际上传输空穴的HOMO能级的材料。这一组分可以是HIL的基础材料，或者它可以是掺杂剂。使用掺杂的HIL允许因为掺杂剂的电性能而选择掺杂剂，并且允许因为形态特性如润湿性、柔性、韧性等而选择基质。HIL材料的优选性能使得空穴能够高效地从阳极注入到HIL材料中。特别地，HIL的电荷携带组分的IP优选不比阳极材料的IP大大约0.7eV以上。更优选地，所述电荷携带组分的IP不比阳极材料的IP大大约0.5eV以上。类似的考虑适用于空穴注入其中的任何层。HIL材料还不同于通常用于OLED的空穴传输层中的普通空穴传输材料，因为这样的HIL材料可以具有明显低于普通空穴传输材料的空穴传导率的空穴传导率。本发明的HIL的厚度可以足够厚，以帮助平面化或润湿阳极层的表面。例如，对于非常光滑的阳极表面来说，小至10nm的HIL厚度可以是可接受的。然而，因为阳极表面往往是非常粗糙的，在一些情况下高达50nm的HIL厚度可能是希望的。
保护层可以被用来在后续制造过程中保护底层。例如，用于制造金属或金属氧化物顶部电极的过程可能损伤有机层，而保护层可用于减少或消除此类损伤。在器件100中，保护层155可以在阴极160的制造过程中减少对底下的有机层的损伤。优选地，保护层对于它所传输的载流子类型(在器件100中的电子)来说具有高的载流子迁移率，使得它不显著地增加器件100的工作电压。CuPc、BCP和各种金属酞菁是可用于保护层中的材料的实例。可以使用其它材料或材料组合。保护层155的厚度优选是足够厚的，使得有很少或没有因在有机保护层160沉积之后进行的制造工艺所导致的对底下的层的损伤；然而保护层155的厚度不应该厚到显著增加器件100的工作电压的程度。保护层155可以被掺杂，以提高它的传导性。例如，CuPc或BCP保护层160可以掺杂Li。保护层的更详细的描述可以在Lu等人的美国专利申请序列号No.09／931,948中找到，它的全部内容通过引用结合在本文中。
图2显示了颠倒的OLED200。该器件包括基材210，阴极215，发射层220，空穴传输层225，和阳极230。器件200可以通过按照顺序沉积所述层来制造。因为最常见的OLED构型具有布置在阳极上的阴极，并且器件200具有布置在阳极230下的阴极215，因此器件200可以被称为“颠倒的”OLED。与讨论器件100时所描述的那些材料类似的材料可用于器件200的相应层中。图2提供了如何从器件100的结构中省略掉一些层的一个实例。
在图1和2中示出的简单层状结构是作为非限制性例子提供的，并且可以理解，本发明的实施方案可以与各种其它结构相结合使用。所述的特定材料和结构是举例性质的，并且其它材料和结构可以被使用。功能化的OLED可以通过以不同的方式组合所述的各种层来实现，或者某些层可以被完全省略，基于设计、性能和成本因素。没有具体描述的其它层也可以被包括。可以使用除了具体描述的那些材料之外的材料。虽然在这里提供的许多实施例将各种层描述为包括单一一种材料，但是可以理解，可以使用材料的组合，如基质和掺杂剂的混合物，或更一般地混合物。同时，这些层可具有各种亚层。在这里给予各种层的名称并不是意图严格限制的。例如，在器件200中，空穴传输层225传输空穴并将空穴注入到发射层220中，因此可以被描述为空穴传输层或空穴注入层。在一个实施方案中，OLED可以被描述为具有设置在阴极和阳极之间的“有机层”。该有机层可以包括单个层，或者可以进一步包括例如讨论图1和2时所述的不同有机材料的多个层。
没有具体描述的结构和材料也可以使用，例如由聚合物材料组成的OLED(PLED)，如公开在美国专利No.5,247,190(Friend等人)中的PLED，该专利的全部内容通过引用结合在本文中。作为另一个例子，可以使用具有单个有机层的OLED。OLED可以堆叠，例如如在美国专利No.5,707,745(Forrest等人)中所述，该专利的全部内容通过引用结合在本文中。OLED结构可以背离在图1和2中图示说明的简单层状结构。例如，基材可以包括有角度的反射面以改进输出耦合(out-coupling)，如在Forrest等人的美国专利No.6,091,195中所述的台式结构，和／或在Bulovic等人的美国专利No.5,834,893中描述的坑形结构，所述专利的全部内容通过引用结合在本文中。
除非另作说明，各种实施方案的这些层中的任何一层可以通过任何合适的方法沉积。对于有机层，优选的方法包括热蒸发，墨喷(如在美国专利No.6,013,982和6,087,196中所述的，所述专利的全部内容通过引用结合在本文中)，有机气相沉积(OVPD)(如在Forrest等人的美国专利No.6,337,102中所述的，该专利的全部内容通过引用结合在本文中)，和通过有机蒸气喷印(OVJP)的沉积(如在美国专利申请No.10／233,470中所述的，该专利申请的全部内容通过引用结合在本文中)。其它合适的沉积方法包括旋涂和其它溶液型工艺。溶液型工艺优选在氮或惰性气氛中进行。对于其它层，优选的方法包括热蒸发。优选的图案化方法包括通过掩模的沉积，冷焊(如在美国专利No.6,294,398和6,468,819中描述的方法，所述专利的全部内容通过引用结合在本文中)，和与某些沉积方法如墨喷和OVJD联合的图案化。其它方法也可以使用。被沉积的材料可以被改性，以使得它们与具体的沉积方法相容。例如，取代基如支化或未支化的并优选含有至少3个碳的烷基和芳基可以用于小分子中，以提高它们经历溶液加工的能力。可以使用具有20个碳或更多个碳的取代基，而3-20个碳是优选的范围。具有不对称结构的材料可以比具有对称结构的那些材料有更好的溶液加工性，因为不对称材料可以有更低的重结晶倾向。树状分子取代基可用来提高小分子经历溶液加工的能力。
在不脱离本发明的范围的情况下，在这里公开的分子可以以许多不同的方式被取代。
根据本发明的实施方案制造的器件可以结合到各种各样的消费产品中，包括平板显示器，计算机显示器，电视，广告牌，内部或外部照明和／或发信号的光源，平视显示器(heads up display)，全透明显示器，柔性显示器，激光打印机，电话，移动电话，个人数字助理(PDA)，膝上型计算机，数字式摄象机，摄像放像机，取景器，微型显示器，车辆，大面积幕墙，戏院或露天运动场屏幕，或标牌。各种控制机构可用来控制根据本发明制造的器件，包括无源矩阵和有源矩阵。许多的器件意图在人感觉舒适的温度范围如18℃到30℃的范围中使用，更优选在室温(20-25℃)使用。
在这里描述的材料和结构可以应用在不同于OLED的器件中。例如，其它光电器件如有机太阳能电池和有机光检测器可以使用所述材料和结构。更一般地，有机器件如有机晶体管可以使用所述材料和结构。
本文中使用的术语“卤代”或“卤素”包括氟、氯、溴和碘。
本文中使用的术语“烷基”包括直链和支链烷基。优选的烷基是含有1到15个碳原子的那些烷基，并且包括甲基，乙基，丙基，异丙基，丁基，异丁基，叔丁基等。另外，所述烷基可以任选地被一个或多个取代基取代，所述取代基选自卤素，CN，CO2R，C(O)R，NR2，环状氨基，NO2和OR。
本文中使用的术语“环烷基”包括环状的烷基。优选的环烷基是含有3到7个碳原子的那些环烷基，并且包括环丙基、环戊基、环己基等。另外，所述环烷基可以任选地被一个或多个取代基取代，所述取代基选自卤素，CN，CO2R，C(O)R，NR2，环状氨基，NO2和OR。
本文中使用的术语“烯基”包括直链和支链烯烃基。优选的烯基是含有2到15个碳原子的那些烯基。另外，所述烯基可以任选被一个或多个取代基取代，所述取代基选自卤素，CN，CO2R，C(O)R，NR2，环状氨基，NO2和OR。
本文中使用的术语“炔基”包括直链和支链炔烃基。优选的烷基是含有2到15个碳原子的那些。另外，所述炔基可以任选被一个或多个取代基取代，所述取代基选自卤素，CN，CO2R，C(O)R，NR2，环状氨基，NO2和OR。
本文中使用的术语“杂环基”包括非芳族环状基团。优选的杂环基是含有包括至少一个杂原子在内的3或7个环原子的那些杂环基，并且包括环状胺如吗啉代、哌啶子基、吡咯烷基等，和环状醚如四氢呋喃、四氢吡喃等。
本文中使用的术语“芳基”或“芳族基团”包括单环基团和多环体系。所述多环可以具有两个或更多个环，其中两个原子被两个相邻的环共用(所述环是“稠合的”)，其中所述环中的至少一个是芳族的，例如，其它环可以是环烷基、环烯基、芳基、杂环和／或杂芳基。
本文中使用的术语“杂芳基”包括单环杂芳基，其可以包括1到4个杂原子，例如吡咯，呋喃，噻吩，咪唑，噁唑，噻唑，三唑，四唑，吡唑，吡啶，吡嗪和嘧啶，等等。所述术语杂芳基还包括具有两个或更多个环的多环杂芳族体系，其中两个原子被两个相邻的环共有(所述环是“稠合的”)，其中所述环中的至少一个是杂芳基，例如，其它环可以是环烷基、环烯基、芳基、杂环和／或杂芳基。
本发明涉及包含磷光物质和苯并[9，10]菲化合物的有机发射层，以及包括这样的发射层的器件。也提供了具体的苯并[9，10]菲化合物。在本发明的优选实施方案中，所述有机发射层包括磷光物质和任选被取代的苯并[9，10]菲化合物。所述取代基可以相同或不同，并且各自选自由如下基团组成的组：烷基、芳基、取代的芳基、烯基、炔基和杂烷基。尤其优选的是可以在不分解的情况下真空蒸发的、分子量小于1400的苯并[9，10]菲化合物。按照本发明制作的器件显示了高效率和寿命。苯并[9，10]菲的高三重态能量使得苯并[9，10]菲化合物特别适合作为与深蓝色磷光掺杂剂一起使用的基质或共基质。
苯并[9，10]菲是具有高三重态能量和相对小的第一单线态和第一三重态能级间的能量差的多芳香烃。这表明，与具有相似三重态能量的其它芳族化合物(例如联苯)相比，苯并[9，10]菲具有相对容易接近的HOMO和LUMO能级。使用苯并[9，10]菲和其衍生物作为基质的优点是，其可以容纳红色、绿色和甚至蓝色磷光掺杂剂，以给出高效率而不会有能量猝灭。
优选地，本发明中的所述苯并[9，10]菲化合物具有的HOMO和LUMO能级间的能隙大于磷光物质的HOMO和LUMO能级间的能隙。
在一个优选实施方案中，本发明中的所述苯并[9，10]菲化合物具有至少约1.8eV的其HOMO能级和其LUMO能级间的能隙。
在另一个实施方案中，所述苯并[9，10]菲化合物具有比磷光物质的最高已占分子轨道低的最高已占分子轨道。
在另一个实施方案中，所述苯并[9，10]菲化合物具有比磷光物质的最低未占分子轨道高的最低未占分子轨道。
在一个实施方案中，本发明提供了包括磷光物质和苯并[9，10]菲化合物的有机发射层，以及包括所述发射层的器件，其中所述苯并[9，10]菲化合物包括多芳基取代的苯并[9，10]菲，优选具有如下结构的2，3，6，7，10，11-六芳基苯并[9，10]菲：
其中R2、R3、R6、R7、R10和R11各自独立地是H或选自由下列基团组成的组的取代基：芳基，取代的芳基，杂芳基，取代的杂芳基，烷基，芳烷基，杂烷基，烯基和炔基；并且其中所述苯并[9，10]菲化合物具有至少两个取代基。
R2、R3、R6、R7、R10和R11可以都是相同的，或者它们可以不同。在一个实施方案中，R2、R3、R6、R7、R10和R11中的每一个都选自芳基和取代的芳基。优选地，R2、R3、R6、R7、R10和R11中的至少一个选自芳基和取代的芳基。优选的是任选取代的苯基、萘基和联苯基。
优选的多芳基取代的苯并[9，10]菲化合物是可以在不分解的情况下被真空蒸发的那些苯并[9，10]菲化合物。实例包括但不局限于如下列结构所示的、其中R2、R3、R6、R7、R10和R11是苯基、萘基和联苯基的化合物：
在另一个实例中，R2、R3、R6、R7、R10和R11都是取代的苯基。这样的实例包括但不局限于具有下列结构的化合物：
在另一个实施方案中，本发明提供了包括磷光物质和具有含有苯并[9，10]菲部分的重复单元的化合物的有机发射层，以及包括所述发射层的器件。
具有含有苯并[9，10]菲部分的重复单元的化合物包括具有如下结构的亚芳基苯并[9，10]菲：
其中
Ar选自芳基和取代的芳基，
X是1-3，
Y是1-3，和
n是1-3。
优选的亚芳基苯并[9，10]菲是具有如下结构的亚苯基苯并[9，10]菲：
其中
X是1-3，
Y是1-3，和
n是1-3。
更优选的亚芳基苯并[9，10]菲化合物是可以在不分解的情况下被真空蒸发的那些亚芳基苯并[9，10]菲化合物。实例包括但不局限于：
具有含有苯并[9，10]菲部分的重复单元的化合物还包括具有如下结构的联苯并[9，10]菲(triphenylenylene)：
优选的联苯并[9，10]菲化合物是低聚(亚苯并[9，10]菲基)，其中n≤5。更优选的是可以在不分解的情况下被真空蒸发的联苯并[9，10]菲化合物。实例包括但不局限于：
具有含有苯并[9，10]菲部分的重复单元的化合物还包括其中苯并[9，10]菲部分具有如下结构的那些化合物：
其
R1、R2和R3各自独立地选自由下列基团组成的组：H，芳基，取代的芳基，杂芳基，取代的杂芳基，烷基，芳烷基，杂烷基，烯基和炔基。
实例包括但不局限于其中苯并[9，10]菲部分具有下式的那些：
其中n>5
具有含有苯并[9，10]菲部分的重复单元的化合物还包括其中苯并[9，10]菲部分具有如下结构的那些化合物：
其中n>5，并且R1、R2、R3和R′各自独立地选自由下列基团组成的组：芳基，取代的芳基，杂芳基，取代的杂芳基，烷基，芳烷基，杂烷基，烯基和炔基。
实例包括但不局限于其中苯并[9，10]菲部分具有下式的那些：
在另一个实施方案中，本发明提供了包括磷光物质和苯并[9，10]菲化合物的有机发射层，以及包括所述发射层的器件，其中所述苯并[9，10]菲化合物具有多苯并苯并[9，10]菲结构。优选的多苯并苯并[9，10]菲是可以在不分解的情况下被真空蒸发的那些。实例包括但不局限于：
在另一个实施方案中，本发明提供了包括磷光物质和苯并[9，10]菲化合物的有机发射层，以及包括所述发射层的器件，其中所述苯并[9，10]菲化合物具有稠合的苯并[9，10]菲结构。优选的稠合的苯并[9，10]菲结构包括但不局限于：
应该理解，在这里描述的各种实施方案仅是作为实例，并且不是为了限制本发明的范围。例如，在不脱离本发明的精神的情况下，在这里描述的许多材料和结构可以被其它材料和结构取代。应该理解，关于本发明为什么发挥作用的各种理论并不是意图是限制性的。
材料定义
在这里使用的一些缩写是指如下材料：
CBP：4，4’-N，N-二咔唑-联苯
m-MTDATA4，4’，4”-三(3-甲基苯基苯基氨基)三苯基胺
Alq3：三(8-羟基喹啉)铝
Bphen：4，7-二苯基-1，10-菲咯啉
n-BPhen：n-掺杂的BPhen(用锂掺杂)
F4-TCNQ：四氟-四氰基-二甲基苯醌
p-MTDATA：p-掺杂的m-MTDATA(用F4-TCNQ掺杂)
Ir(ppy)3：三(2-苯基吡啶)合铱
Ir(ppz)3：三(1-苯基吡唑根，N，C(2’))合铱(III)
BCP：2，9-二甲基-4，7-二苯基-1，10-菲咯啉
TAZ：3-苯基-4-(1’-萘基)-5-苯基-1，2，4-三唑
CuPc：铜酞菁
ITO：氧化铟锡
NPD：N，N’-二苯基-N，N’-二(1-萘基)-联苯胺
TPD：N，N’-二苯基-N，N’-二(3-甲苯基)-联苯胺
BAlq：双(2-甲基-8-羟基喹啉根)·4-苯基苯酚根合铝(III)
mCP：1，3-N，N-二咔唑-苯
DCM：4-(二氰基亚乙基)-6-(4-二甲基氨基苯乙烯基-2-甲基)-4H-吡喃
DMQA：N，N’-二甲基喹吖啶酮
PEDOT：PSS：聚(3，4-亚乙基二氧基噻吩)与聚苯乙烯磺酸盐(PSS)的水性分散体
HPT：2，3，6，7，10，11-六苯基苯并[9，10]菲
2，7-DCP：2，7-N，N-二咔唑菲
3，3’-DC-o-TerP：3，3’-二咔唑-邻三联苯
4，4’-DC-o-TerP：4，4’-二咔唑-邻三联苯
2，6’-DCN：2，6-N，N-二咔唑萘
Ir(5-Phppy)3：三[5’-苯基(2-苯基吡啶)]合铱(III)
Ir(3-Meppy)3：三(3-甲基-2-苯基吡啶)合铱(III)
Ir(1-piq)3：三(1-苯基异喹啉)合铱(III)
Ir(3-Mepq)2(acac)：二[3-甲基-2-苯基喹啉]合铱(III)乙酰丙酮化物
Ir(5-Phppy)3：三[5-苯基(2-苯基吡啶)]合铱(III)
Ir(pq)2(acac)：二[2-苯基喹啉]合铱(III)乙酰丙酮化物
2，2-BT：2，2-联苯并[9，10]菲
HPT：2，3，6，7，10，11-六苯基苯并[9，10]菲
H1NT：2，3，6，7，10，11-六(1-萘基)苯并[9，10]菲
H2BT：2，3，6，7，10，11-六(2-联苯基)苯并[9，10]菲
现在将描述本发明的具体的代表性实施方案，包括这样的实施方案可以如何被制备。应该理解，所述的具体的方法、材料、条件、工艺参数、装置等不必然地限制本发明的范围。
多芳基取代的苯并[9，10]菲化合物的合成
2，3，6，7，10，11-六苯基苯并[9，10]菲(HPT)的合成
按照US20050025993合成2，3，6，7，10，11-六苯基苯并[9，10]菲。
2，3，6，7，10，11-六(4-叔丁基苯基)苯并[9，10]菲(4-叔丁基HPT)的合成
步骤1.2，3，6，7，10，11-六溴苯并[9，10]菲的制备
按照文献方法(Breslow等人，Tetrahedron，1982，38，863)制备2，3，6，7，10，11-六溴苯并[9，10]菲。将苯并[9，10]菲(3.0克，13.2mmol)溶于70毫升硝基苯中。添加0.27克Fe粉。通过滴液漏斗向该混合物中添加溴(18.6克，120mmol)在20毫升硝基苯中的溶液。将混合物在室温下搅拌12小时，并回流2小时。冷却后，过滤固体，用乙醇洗涤，并干燥。得到8.9克(96％)的粗产品。在沸腾1，2-二氯苯(～180℃)中的重结晶得到呈灰白色针状物的产物(8.64克，94％)。该产物通过质谱确认。
步骤2：2，3，6，7，10，11-六(4-叔丁基苯基)苯并[9，10]菲(化合物VII)的制备
将2，3，6，7，10，11-六溴苯并[9，10]菲(8.64克，12.3mmol)、4-叔丁基苯基硼酸(13.5克，111mmol)、三苯基膦(0.64克，2.46mmol)、Pd(OAc)2(0.14克，0.615mmol)、K2CO3(20.4克，147.6mmol)放入600毫升二甲苯和50毫升水中。将混合物用氮气吹扫5分钟，并在氮气氛下缓慢升温至回流。在几小时之内，TLC(CH2Cl2：己烷～1：2v／v，起始的六溴化合物不移动)显示新斑点的出现(二甲苯也显现在TLC上，但它比产物洗脱的更快)。将混合物回流12小时。冷却后，过滤固体，用乙醇洗涤，并干燥。粗品产率高于90％。在二甲苯中的重结晶(每3-4克产物～100毫升)得到白色晶体。真空升华得到产物(～4.5克)，该产物通过NMR和质谱确认。该物质在常见有机溶剂中极易溶，并且可以在溶液加工的器件中使用。例如，可以将4-叔丁基HPT在甲苯中的1％重量溶液在1000和2000rpm的速度下旋转涂布在硅晶片上，分别得到～60和～40nm厚的均匀薄膜。
2，3，6，7，10，11-六(2-萘基)苯并[9，10]菲(H2NT)的合成
将2.0克2，3，6，7，10，11-六溴苯并[9，10]菲(2.85mmol)、4.4克萘-2-基硼酸(25.6mmol)、0.15克三苯基膦(0.57mmol)、0.03克乙酸钯(0.14mmol)放在3颈1L圆底烧瓶中。然后添加250毫升二甲苯，接着添加250毫升0.1M的碳酸钾溶液。通过鼓入氮气30分钟，将混合物彻底脱气。然后将混合物在氮气氛中回流24小时。然后使反应自然冷却，并将内含物转入分液漏斗中。除去水层，将有机层用水洗涤。将有机层用硫酸镁干燥，而后真空除去溶剂。使用柱色谱纯化产物，用二氯甲烷／己烷(50／50)作为流动相。
2，3，6，7，10，11-六(1-萘基)苯并[9，10]菲(H1NT)的合成
将2.0克2，3，6，7，10，11-六溴苯并[9，10]菲(2.80mmol)、4.4克萘-1-基硼酸(25.6mmol)、0.22克二环己基(2’，6’-二甲氧基联苯-2-基)膦(0.5mmol)、0.14克三(二亚苄基丙酮)合钯(0)(0.15mmol)放在3颈1L圆底烧瓶中。然后添加250毫升二甲苯，接着添加250毫升0.1M的磷酸三钾溶液。通过鼓入氮气30分钟，将混合物彻底脱气。然后将混合物在氮气氛中回流24小时。然后使反应自然冷却，并将内含物转入分液漏斗中。除去水层，将有机层用水洗涤。将有机层用硫酸镁干燥，而后真空除去溶剂。使用柱色谱纯化产物，用二氯甲烷：己烷(50：50)作为流动相。
2，3，6，7，10，11-六(联苯-2-基)苯并[9，10]菲(H2BT)的合成
将1.0克2，3，6，7，10，11-六溴苯并[9，10]菲(1.4mmol)、2.5克联苯-2-基硼酸(25.6mmol)、0.11克二环己基(2’，6’-二甲氧基联苯-2-基)膦(0.26mmol)、0.07克三(二亚苄基丙酮)合钯(0)(0.076mmol)放在3-颈1L圆底烧瓶中。然后添加250毫升二甲苯，接着添加250毫升0.1M的磷酸三钾溶液。通过鼓入氮气30分钟，将混合物彻底脱气。然后将混合物在氮气氛中回流24小时。然后使反应自然冷却，并将内含物转入分液漏斗中。除去水层，将有机层用水洗涤。将有机层用硫酸镁干燥，而后真空除去溶剂。使用柱色谱纯化产物，用二氯甲烷：己烷(50：50)作为流动相。
通过Suzuki偶合，用相应的卤代苯并[9，10]菲和芳基硼酸，本领域技术人员可以合成其它多芳基取代的苯并[9，10]菲实例。
苯并[9，10]菲和2，3，6，7，10，11-六芳基苯并[9，10]菲的电化学概括在表1中。
表1
具有苯并[9，10]菲重复单元的化合物的合成
联苯并[9，10]菲化合物
2，2-联苯并[9，10]菲(2，2-BT)的合成
按照Organic Letters2001，3，811和UA20040076852A1合成2，2-联苯并[9，10]菲。
1，1-联苯并[9，10]菲(1，1-BT)的合成
可以按照Organometallics，2004，23，3079合成1，1-联苯并[9，10]菲。
亚芳基苯并[9，10]菲化合物
1，3-二(苯并[9，10]菲-2-基)苯的合成
步骤1：2-溴苯并[9，10]菲的合成
将3.2克(14mmol)苯并[9，10]菲溶于60毫升磷酸三甲酯中。在室温下，在N2氛围中，向该悬浮液中添加2.23克(14mmol)溴在10毫升磷酸三甲酯中的溶液。然后将混合物加热至80℃。通过HPLC监测反应。通过倾倒入冰水中来猝灭反应，然后用二氯甲烷提取，用饱和亚硫酸氢钠溶液洗涤。用硫酸镁干燥之后，蒸发溶剂。使粗产品流过短的硅胶柱，使用二氯甲烷。真空干燥之后，得到3.0克产物。产物含有苯并[9，10]菲、1-溴苯并[9，10]菲、2-溴苯并[9，10]菲和二溴苯并[9，10]菲异构体的混合物。
步骤2：4，4，5，5-四甲基-2-(苯并[9，10]菲-2-基)-1，3，2-二氧杂硼杂环戊烷的合成
在室温下，在N2气氛下，将3.0克所述溴代苯并[9，10]菲混合物、2.8克(11mmol)二(频哪醇)二硼、0.24克Pd(dppf)2Cl2、3.0克(30mmol)乙酸钾和60毫升DMSO混合。将混合物脱气，而后加热至80℃，保持14小时。冷却至室温后，将混合物倾倒入冰水中。然后过滤收集沉淀物。将固体溶于乙醚中，用硫酸镁干燥。将粗产品用柱纯化，使用己烷和二氯甲烷的混合物作为洗脱液。分离出1.3克纯产物。
步骤3：1，3-二(苯并[9，10]菲-2-基)苯的合成
将得自前述步骤的1.23克(3.5mmol)苯并[9，10]菲硼酸酯、0.5克(1.5mmol)1，3-二碘苯、1.0克(7.5mmol)碳酸钾、30毫升甲苯和10毫升水在250毫升三颈烧瓶中混合。用氮气吹扫所述系统10分钟，而后添加0.05克Pd(PPh3)4。然后将混合物加热至87℃，同时强烈搅拌。24小时之后，向混合物中添加200毫升甲醇。过滤收集沉淀物。将固体用大量甲醇洗涤，然后用己烷洗涤。然后用80毫升二甲苯将固体重结晶。所述产物的最后纯化包括使所述物质在250℃升华。收集0.35克产物，为白色针形结晶。
3，3’-二(苯并[9，10]菲-2-基)联苯的合成
步骤1：2-氨基苯并[9，10]菲的合成
将在大约100毫升乙醇中的3.1克(11.3mmol)1-和2-硝基苯并[9，10]菲的混合物(按照J.Chem.Soc，1955，4482合成)、600毫克(0.57mmol)Pd／C(10％，在活性炭上)和2.3克(45.2mmol)肼一水合物加入到250毫升圆底烧瓶中。在氮气氛下，将反应混合物加热至回流，保持2小时。然后过滤反应混合物，将滤液浓缩，并使其通过硅胶柱，使用25％的乙酸乙酯己烷溶液作为洗脱液。分离1-和2-氨基苯并[9，10]菲，并通过MS和NMR确认。反应产率为100％。
步骤2：2-溴苯并[9，10]菲的合成
将0.5克(2.05mmol)2-氨基苯并[9，10]菲和0.24克(1.02mmol)无水溴化铜(II)放在100毫升圆底烧瓶中。将烧瓶用氮气吹扫并排气数次。将25毫升无水乙腈添加到所述固体中。然后将烧瓶放入冰／盐浴(-5℃)中。通过隔膜向所述溶液中滴加0.27毫升亚硝酸异戊酯。在所有的亚硝酸异戊酯添加完毕之后，搅拌混合物两个小时。然后从冰浴中移开烧瓶，在室温下搅拌一小时，而后在55℃加热2小时。然后冷却混合物，真空除去溶剂，并使用己烷／二氯甲烷(10％／90％)对产物进行柱色谱分离，得到0.36克(60％)产物。
步骤3：3，3’-二(苯并[9，10]菲-2-基)联苯的合成
将0.1克(0.32mmol)3，3’-二溴联苯、0.24克(0.66mmol)4，4，5，5-四甲基-2-(苯并[9，10]菲-2-基)-1，3，2-二氧杂硼杂环戊烷、0.03克(0.07mmol)2-二环己基膦基-2’，6’-二甲氧基联苯(S-Phos)和0.01克(0.01mmol)三(二亚苄基丙酮)合钯(0)放在3-颈100毫升圆底烧瓶中。然后将20毫升二甲苯和20毫升3M磷酸三钾一水合物溶液添加到混合物中。将双相溶液用氮气彻底吹扫半小时。将混合物回流18小时。当冷却时，产物沉淀出来。将产物过滤，并用水洗涤。然后将产物溶于二氯甲烷中，并通过硅胶柱。真空除去溶剂，得到0.17克(89％产率)产物。
具有下列结构的亚芳基苯并[9，10]菲苯并[9，10]菲化合物的合成：
可以按照Angew.Chem.，Int.Ed.Engl.，1996，35，886合成具有上面结构的化合物。
其它联苯并[9，10]菲和亚芳基苯并[9，10]菲的实例可以由本领域技术人员通过1-或2-溴苯并[9，10]菲与4，4，5，5-四甲基-2-(1-或2-苯并[9，10]菲)-1，3，2-二氧杂硼杂环戊烷(可以按照上述的合成反应路线制备)的偶合来合成。
苯并[9，10]菲聚合物
聚(2-乙烯基苯并[9，10]菲)的制备
可以通过如下反应路线、基于本领域技术人员通常使用的合成化学来合成聚(2-乙烯基苯并[9，10]菲)。
聚[2-(4-乙烯基苯基)苯并[9，10]菲]的合成
可以按照如下反应路线、基于本领域技术人员通常使用的合成化学来合成聚[2-(4-乙烯基苯基)苯并[9，10]菲]。
聚(2，7-苯并[9，10]菲)的合成：
可以按照如下反应路线、基于本领域技术人员通常使用的合成化学来合成聚(2，7-苯并[9，10]菲)。
聚(2，7-亚苯并[9，10]菲基-1，4-亚苯基)的合成
可以按照如下反应路线、基于本领域技术人员通常使用的合成化学来合成聚(2，7-亚苯并[9，10]菲基-1，4-亚苯基)。
苯并亚苯并[9，10]菲基苯并[9，10]菲化合物的合成
具有下列结构的苯并亚苯并[9，10]菲基苯并[9，10]菲化合物的合成：
可以按照J.Org.Chem.，1996，61，7198合成具有上面结构的化合物。
具有下列结构的苯并亚苯并[9，10]菲基苯并[9，10]菲化合物的合成：
可以按照Org.Lett.，2000，2，1629合成具有上面结构的化合物。
稠合的苯并[9，10]菲化合物的合成
1，12-稠合的二苯并[9，10]菲(1，12-稠合的BT)的合成
可以按照Organometallics，2004，23，3079合成1，12-稠合的二苯并[9，10]菲。
1，12-稠合的四苯并[9，10]菲(1，12-稠合的TT)的合成
可以按照下列反应路线合成1，12-稠合的四苯并[9，10]菲。
本领域技术人员可以理解，取代的前体可用于合成取代的苯并[9，10]菲产物，它们可以提供与未取代的类似物不同的性能，例如更高的溶解性、更低的蒸发温度、更高／更低的HOMO／LUMO能级，这在具体器件的制作、构造和应用中可能是有利的。
器件制作和测定
所有的器件是通过高真空(<10-7托)热蒸发来制作的。阳极电极是～1200埃的氧化铟锡(ITO)。阴极由10埃的LiF和后面的1,000埃的Al组成。所有器件在制造之后马上在氮气手套箱(<1ppm的H2O和O2)中用玻璃盖子封装并用环氧树脂密封，并且在包装内引入吸湿气剂。
器件实施例1-23和对比例1-6
有机堆叠体从ITO表面开始按顺序包括作为空穴注入层(HIL)的100埃厚的铜酞菁(CuPc)、作为空穴传输层(HTL)的300埃的4，4’-二[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)、作为发射层(EML)的300埃的掺杂有6或12wt％掺杂发射体的苯并[9，10]菲化合物或对比化合物。器件实施例1、4、7、10、13、16和22及对比器件实施例1、2、3和4包括100-150埃的二(2-甲基-8-羟基喹啉根)·4-苯基苯酚根合铝(III)(BAlq)作为ETL2和400-500埃的三(8-羟基喹啉根)合铝(Alq3)作为ETL1。器件实施例2、5、8、11、14、19、20、21和23及对比器件实施例5和6包括50-150埃的HPT作为ETL2和400-500埃的Alq3作为ETL1。器件实施例3、6、9、12、15和18包括400-500埃的Alq3作为ETL2，没有ETL1。确切的ETL层厚度示于表2中。HPT、2，2-BT和适合作为基质材料的苯并[9，10]菲化合物的附加实例的结构示于图17中。
发红光器件在500cd／m2条件下的发光效率或发绿光器件在1000cd／m2条件下的发光效率概括在表2中。
作为基质材料，苯并[9，10]菲化合物显示了高的器件效率。与使用对比化合物CBP作为基质的那些器件相比较，使用HPT作为基质的器件显示了相当的或更高的效率。
测定选择的器件的电流-电压-发光度(IVL)特征和操作稳定性，并在图3-16和图18-31中画出。具有苯并[9，10]菲基质的器件的寿命与用对比化合物CBP作为基质的器件的寿命相当。
表2.
对于各种磷光掺杂剂，HPT、2，2-BT、H1NT和H2BT作为基质的器件结构和性能的总结。
具有很高器件效率的磷光器件在例如显示器、发光等的应用中是高度理想的。对于全色和发光应用，在红、绿和蓝色中高操作稳定性是必要的。由于蓝色磷光掺杂剂发射体的高三重态能量特性，需要高三重态能量的基质材料，以便可以获得高的器件效率。在OLED中，具有扩展的π-共轭作用的多芳香化合物通常显示相当长的寿命。然而，具有扩展的π-共轭作用的多芳香化合物通常也具有低的三重态能量。例如，蒽具有1.8eV的三重态能量，其比红色磷光掺杂剂例如Ir(1-piq)2(acac)的三重态能量低。结果，因为猝灭，用蒽化合物作为基质、用Ir(1-piq)2(acac)作为掺杂剂发射体的器件是非常低效率的。从蒽中减少一个稠合苯基环将得到萘，其是最小的稠合多芳香化合物。然而，它仍然具有2.6eV的三重态能量，该三重态能量比深蓝色磷光掺杂剂如Ir(4，6-F2-5CNppy)3的三重态能量低。然而，尽管苯并[9，10]菲具有四个稠合环的结构，其具有2.9eV的三重态能量，该三重态能量据信适合于深蓝色磷光掺杂剂如Ir(4，6-F2-5CNppy)3。苯并[9，10]菲可以用多种方式衍生化，例如添加烷基或芳基，通过不同位置连接多个苯并[9，10]菲或稠合苯并[9，10]菲，从而调节电子性能(例如共轭作用、三重态能量、HOMO／LUMO能级等)，结构性能(例如平面、非平面、手性)，和物理性能(例如升华温度、溶解性)。苯并[9，10]菲化合物提供了相对大的π-共轭程度但相对高的三重态能量的独特特性，使得它们非常适合于稳定和高效率的PHOLED。例如，六苯基苯并[9，10]菲(HPT)作为红色掺杂剂Ir(3-Mepq)2(acac)和Ir(1-piq)3的基质，给出有效的和高度稳定的器件，如图3-5和6-8中分别显示的。尽管具有2，2-联苯并[9，10]菲(2，2-BT)作为基质的器件显示了比具有对比化合物CBP作为基质的器件低的效率，但使用2，2-BT作为红色掺杂剂Ir(3-Mepq)2(acac)和Ir(1-piq)3的基质导致相对有效和高度稳定的器件，如图9-11(11-13)和12-14(14-16)中分别显示的。
Claims (23)
1.一种全色或蓝色发射层，包含磷光物质和由具有下式的苯并[9,10]菲化合物组成的主体材料：
其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12各自独立地是H或选自由下列基团组成的组的取代基：芳基，取代的芳基，杂芳基，取代的杂芳基，烷基，芳烷基，烯基和炔基；其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12中的至少一个选自芳基和取代的芳基，并且其中所述苯并[9,10]菲化合物具有至少两个取代基和小于1400的分子量，前提是所述苯并[9,10]菲化合物不是2,3,6,7,10,11-六苯基苯并[9,10]菲，并且前提是R1-R12中没一个基团是未取代或取代的2-(2-吡啶基)苯基。
2.权利要求1的发射层，其中R1、R4、R5、R8、R9和R12都是H，并且R2、R3、R6、R7、R10和R11中的每一个独立地选自芳基和取代的芳基。
3.权利要求2的发射层，其中R2、R3、R6、R7、R10和R11全都相同。
4.权利要求2的发射层，其中R2、R3、R6、R7、R10和R11选自苯基、萘基和联苯基。
5.权利要求3的发射层，其中R2、R3、R6、R7、R10和R11选自苯基、萘基和联苯基。
6.权利要求1的发射层，其中所述苯并[9,10]菲化合物选自由如下化合物组成的组：
7.权利要求1的发射层，其中所述苯并[9,10]菲化合物具有的其HOMO能级和LUMO能级间的能隙大于所述磷光物质的HOMO能级和LUMO能级间的能隙。
8.权利要求1的发射层，其中所述苯并[9,10]菲化合物具有至少1.8eV的其HOMO能级和其LUMO能级间的能隙。
9.权利要求1的发射层，其中所述苯并[9,10]菲化合物具有的最高已占分子轨道低于所述磷光物质的最高已占分子轨道。
10.权利要求1的发射层，其中所述苯并[9,10]菲化合物具有的最低未占分子轨道高于所述磷光物质的最低未占分子轨道。
11.一种全色或蓝色发射层，其包含磷光物质和由具有苯并苯并[9,10]菲结构的苯并[9,10]菲化合物组成的主体材料。
12.权利要求11的发射层，其中所述苯并[9,10]菲化合物具有下列结构：
13.权利要求11的发射层，其中所述苯并[9,10]菲化合物具有的其HOMO能级和LUMO能级之间的能隙大于所述磷光物质的HOMO能级和LUMO能级之间的能隙。
14.权利要求11的发射层，其中所述苯并[9,10]菲化合物具有至少1.8eV的其HOMO能级和其LUMO能级之间的能隙。
15.权利要求11的发射层，其中所述苯并[9,10]菲化合物具有的最高已占分子轨道低于所述磷光物质的最高已占分子轨道。
16.权利要求11的发射层，其中所述苯并[9,10]菲化合物具有的最低未占分子轨道高于所述磷光物质的最低未占分子轨道。
17.一种全色或蓝色发射层，其包含磷光物质和由具有稠合的亚苯并[9,10]菲基结构的苯并[9,10]菲化合物组成的主体材料。
18.权利要求17的发射层，其中所述苯并[9,10]菲化合物具有下列结构：
19.权利要求17的发射层，其中所述苯并[9,10]菲化合物具有的其HOMO能级和LUMO能级之间的能隙大于所述磷光物质的HOMO能级和LUMO能级之间的能隙。
20.权利要求17的发射层，其中所述苯并[9,10]菲化合物具有至少1.8eV的其HOMO能级和其LUMO能级之间的能隙。
21.权利要求17的发射层，其中所述苯并[9,10]菲化合物具有的最高已占分子轨道低于所述磷光物质的最高已占分子轨道。
22.权利要求17的发射层，其中所述苯并[9,10]菲化合物具有的最低未占分子轨道高于所述磷光物质的最低未占分子轨道。
23.有机场致发光器件，其包括∶
阳极，
阴极，和
在所述阳极和所述阴极之间的发射层，该发射层包含由苯并[9,10]菲化合物组成的主体材料和磷光物质，所述苯并[9,10]菲化合物具有下式：
其中R1-R3各自独立地是H或选自由下列基团组成的组的取代基：芳基，取代的芳基，杂芳基，取代的杂芳基，烷基，芳烷基，烯基和炔基，其中所述苯并[9,10]菲化合物具有至少两个取代基和小于1400的分子量，前提是所述苯并[9,10]菲化合物不是2,3,6,7,10,11-六苯基苯并[9,10]菲，并且前提是R1-R3中没一个基团是未取代或取代的2-(2-吡啶基)苯基。
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| EP1888708A2 (en) | 2008-02-20 |
| US20130001538A1 (en) | 2013-01-03 |
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| KR101357475B1 (ko) | 2014-02-03 |
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| CN103435436A (zh) | 2013-12-11 |
| EP2277978A2 (en) | 2011-01-26 |
| CN103746080A (zh) | 2014-04-23 |
| EP2277978A3 (en) | 2011-05-04 |
| US9139494B2 (en) | 2015-09-22 |
| JP5095612B2 (ja) | 2012-12-12 |
| JP5778046B2 (ja) | 2015-09-16 |
| JP2015109481A (ja) | 2015-06-11 |
| EP2277978B1 (en) | 2016-03-30 |
| EP3064563A1 (en) | 2016-09-07 |
| JP6077579B2 (ja) | 2017-02-08 |
| WO2006130598A3 (en) | 2007-07-05 |
| EP1888708B1 (en) | 2012-11-21 |
| JP2008543086A (ja) | 2008-11-27 |
| KR20140082808A (ko) | 2014-07-02 |
| WO2006130598A2 (en) | 2006-12-07 |
| CN101203583A (zh) | 2008-06-18 |
| KR20080013934A (ko) | 2008-02-13 |
| US8092924B2 (en) | 2012-01-10 |
| JP2012080130A (ja) | 2012-04-19 |
| KR101634423B1 (ko) | 2016-06-28 |
| US20060280965A1 (en) | 2006-12-14 |
| EP3064563B1 (en) | 2018-12-26 |
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