CN103502223A - 用于发光装置的苯并咪唑衍生物 - Google Patents
用于发光装置的苯并咪唑衍生物 Download PDFInfo
- Publication number
- CN103502223A CN103502223A CN201180060609.2A CN201180060609A CN103502223A CN 103502223 A CN103502223 A CN 103502223A CN 201180060609 A CN201180060609 A CN 201180060609A CN 103502223 A CN103502223 A CN 103502223A
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- Prior art keywords
- iridium
- phenyl
- iii
- bis
- light
- Prior art date
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 230000005525 hole transport Effects 0.000 claims description 11
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 7
- 239000010410 layer Substances 0.000 description 78
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 76
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 35
- 239000000463 material Substances 0.000 description 33
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 229910052741 iridium Inorganic materials 0.000 description 29
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 29
- 239000007787 solid Substances 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- UNRQTHVKJQUDDF-UHFFFAOYSA-N acetylpyruvic acid Chemical compound CC(=O)CC(=O)C(O)=O UNRQTHVKJQUDDF-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- -1 methyl cyclobutyl Chemical group 0.000 description 17
- 229960001866 silicon dioxide Drugs 0.000 description 16
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 241000208340 Araliaceae Species 0.000 description 13
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 13
- 235000003140 Panax quinquefolius Nutrition 0.000 description 13
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 11
- 239000007983 Tris buffer Substances 0.000 description 11
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 11
- 238000004020 luminiscence type Methods 0.000 description 11
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 235000015320 potassium carbonate Nutrition 0.000 description 8
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 8
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
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- 239000012266 salt solution Substances 0.000 description 7
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- 230000000930 thermomechanical effect Effects 0.000 description 7
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 6
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 6
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- ZZPNDIHOQDQVNU-UHFFFAOYSA-N 2-hydroxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(O)OC1(C)C ZZPNDIHOQDQVNU-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- 239000000956 alloy Substances 0.000 description 4
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- 125000003118 aryl group Chemical group 0.000 description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
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- 229940126214 compound 3 Drugs 0.000 description 4
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- 238000011049 filling Methods 0.000 description 4
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- 150000002367 halogens Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- JYAVHXABZQYLTH-UHFFFAOYSA-N n-[4-(4-bromophenyl)phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 JYAVHXABZQYLTH-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
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- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
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- VDULMXJUOWIPGE-UHFFFAOYSA-N 1-phenylisoquinoline quinoline Chemical compound N1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 VDULMXJUOWIPGE-UHFFFAOYSA-N 0.000 description 3
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Abstract
可作为发光装置中的主体的化合物，其包括视情况取代的环系统1-4。
Description
本申请主张于2010年12月22日提交的第61/426,259号美国临时专利申请以及2011年2月23日提交的第13/033,473号美国专利申请的优先权，以上两篇美国专利申请作为参考全部纳入到本文中。
技术领域
本发明的实施例包括用于发光装置的化合物。
背景技术
有机发光装置被广泛地开发作为平板显示器，且快速地朝固态发光(solidstate lighting，SSL)的应用发展。为实现此装置的完全商业潜力，必需要持续地开发新的化合物作为改善此装置的效率及/或使用寿命。
发明内容
本发明的一些实施例包括化合物，其包含一选择性地取代的环系统(ringsystem)，选自于由：
(环系统1)、
本发明一些实施例包括发光装置，其包含一于此描述的化合物。
附图说明
图1为本发明装置的一实施例的示意图。
图2为发光装置的实施例的电激发光光谱。
图3为发光装置的实施例的电流密度/亮度vs.电压的曲线。
图4为发光装置的实施例的外部量子效率(external quantum efficiency，EQE)。
图5为发光装置的实施例的电流效率/功率效率vs.电流密度的图标。
图6为发光装置的实施例的功率输出vs.电压的图标。
图7为发光装置的实施例的电激发光光谱。
图8为发光装置的实施例的电流密度/亮度vs.电压的曲线。
图9为发光装置的实施例的亮度(cd/m2)的功率效率及电激发光效率。
图10为发光装置的实施例的电流密度/亮度vs.电压的曲线。
图11为发光装置的实施例的亮度(cd/m2)的功率效率及电激发光效率。
具体实施方式
除非另有说明，当一化学结构特征例如芳香基被称为“选择性地被取代”，其意思为可以不具有”取代基”(亦即，尚未取代)或可以具有一个或多个取代基。“被取代的”特征具有一个或多个取代基。该技术领域中的普通技术人员已知“取代基”一词通常的意涵。在一些实施例中，该取代基为一卤素，或具有1个至20个碳原子，1至10个碳原子，或具有分子量低于大约500，大约300，或大约200。在一些实施例中，该取代基具有至少1个碳原子或至少1个杂原子(heteroatom)，且具有大约0个至10个碳原子及大约0个至5个杂原子独立地选自于由：氮、氧、硫、氟、氯、溴、碘及其任一组合。在一些实施例中，各取代基由大约0个至20个碳原子，大约0个至47个氢原子，大约0个至5个氧原子，大约0个至2个硫原子，大约0个至3个氮原子，大约0个至1个硅原子，大约0个至7个氟原子，大约0个至3个氯原子，大约0个至3个溴原子，及大约0个至3个碘原子所组成。例子包括但不局限于：烷基(alkyl)、烯基(alkenyl)、炔基(alkynyl)、咔唑基(carbazolyl)、环烷基(cycloalkyl)、环烯基(cycloalkenyl)、环炔基(cycloalkynyl)、芳香基(aryl)、双芳胺基(diarylamino)、杂芳基(heteroaryl)、杂脂环基(heteroalicyclyl)、芳烷基(aralkyl)、杂芳烷基(heteroaralkyl)、(杂脂环基)烷基((heteroalicyclyl)alkyl)、羟基(hydroxyl)、有保护基的羟基(protected hydroxyl)、烷氧基(alkoxy)、芳氧基(aryloxy)、酰基(acyl)、酯(ester)、巯基(mercapto)、烷硫基(alkylthio)、芳硫基(arylthio)、氰基(cyano)、卤素(halogen)、羰基(carbonyl)、硫羰基(thiocarbonyl)、O-胺甲酰基(O-carbamyl)、N-胺甲酰基(N-carbamyl)、O-胺硫甲酰基(O-thiocarbamyl)、N-胺硫甲酰基(N-thiocarbamyl)、C-酰胺基(C-amido)、N-酰胺基(N-amido)、S-磺酰胺基(S-sulfonamido)、N-磺酰胺基(N-sulfonamido)、C-羧基(C-carboxy)、有保护基的C-羧基(protected C-carboxy)、O-羧基(O-carboxy)、异氰酸基(isocyanato)、硫氰酸基(thiocyanato)、异硫氰酸基(isothiocyanato)、硝基(nitro)、硅烷基(silyl)、次磺酰基(sulfenyl)、亚磺酰基(sulfinyl)、磺酰基(sulfonyl)、卤烷基(haloalkyl)、卤烷氧基(haloalkoxyl)、三卤甲烷磺酰基(trihalomethanesulfonyl)、三卤甲烷磺酰胺基(trihalomethanesulfonamido)及胺基(包括单取代和双取代的胺基)及其有保护基的衍生物。
在一些实施例中，取代基可包括(但不局限于)C1-10烷基(例如：甲基、乙基、丙基异构物(例如是正丙基及异丙基)、环丙基、丁基异构物、环丁基异构物(例如是环丁基、甲基环丁基等)、戊基异构物、环戊基异构物、己基异构物、环己基异构物、庚基异构物、环庚基异构物等；烷氧基(例如：-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13、-OC7H15等)；卤基(例如：氟、氯、溴、碘等)；C1-10卤烷基，其包括过氟化烷基(perfluoroalkyl)(例如：-CF3、-C2F5、-C3F7、-C4F9等)；C1-10酰基(例如：甲酰基、乙酰基、苯甲酰基等)；C1-10酰胺(与其羰基或氮原子相接，例如：-NCOCH3、-CONHCH2等)；C1-10酯(与其羰基或氧原子相接，例如：-OCOCH3、-CO2CH2等)；C1-10胺基甲酸酯(carbamate，与其氮原子或氧原子相接)；氰基；氰酸酯；异氰酸酯；硝基等。
在一些实施例中，取代基可选择自氟、氯、C1-6烷基、-O-C1-6烷基、CN、NO2以及CF3。
在一些实施例中，该化合物主要可由各不含取代基的环系统1、环系统2、环系统3或环系统4所组成，或是由各环系统上含有一个或多个取代基的环系统1、环系统2、环系统3或环系统4所组成。在一些实施例中，环系统1、环系统2、环系统3或环系统4可各具有1、2、3、4、5、6、7、8、9或10个取代基。
本发明所描述的化合物及组合物可用多种方式并入发光装置中。举例而言，一实施例提供设置于阳极及阴极之间的一有机组件(component)。在一些实施例中，该装置可经配置使得电洞可自阳极传输至该有机组件。在一些实施例中，该装置可经配置使得电子可自阴极传输至该有机组件。该有机组件可包括于此所述的化合物及/或组合物。
该阳极可为包含现有材料，例如：金属、混合金属、合金、金属氧化物或混合金属氧化物、导电聚合物及/或无机材料，例如：纳米碳管(carbonnanotube，CNT)的膜层。合适的金属的例子包括第1族金属、第4、5、6族金属及第8-10族的过渡金属。若该阳极层需为透光(light-transmitting)，则可使用第10族及第11族金属，例如：金、铂及银、或其合金；或是第12、13及14族金属的混合金属氧化物，例如：铟锡氧化物(indium-tin-oxide，ITO)、铟锌氧化物(indium-zinc-oxide，IZO)及类似物。在一些实施例中，该阳极层可为有机材料，例如：聚苯胺(polyaniline)。聚苯胺的使用是描述于“由可溶性导电聚合物所制造的可挠式发光二极管”(“Flexible light-emitting diodesmade from soluble conducting polymer”)(自然(Nature)，第357卷，第477-479页(1992年6月11日))中。合适的高功函数金属及金属氧化物的例子包括但不限于，金、铂或其合金；ITO；IZO以及类似物。在一些实施例中，该阳极层的厚度为约1纳米至约1000纳米的范围。
该阴极层可以是包括具有低于该阳极层的功函数材料的膜层。用于该阴极层的合适材料包括选择自第1族的碱金属、第2族金属、第12族金属，包括稀土元素(rare earth elements)、镧系元素(lanthanides)及锕系元素(actinides)、例如：铝、铟、钙、钡、钐及锰的材料以及其组合。也可在该有机层与该阴极层之间置入含锂的有机金属化合物、LiF以及LiO2以降低操作电压。合适的低功函数金属包括但不局限于，Al、Ag、Mg、Ca、Cu、Mg/Ag、LiF/Al、CsF、CsF/Al或其合金。在一些实施例中，该阴极层的厚度为约1奈米至约1000纳米的范围。
在一些实施例中，该有机组件可包括至少一个发光层，其包括发光组件，以及视情况而言，包括一主体(host)。主体可包括本文所述的一化合物、一电洞传输材料、一电子传输材料及/或一双载子(ambipolar)材料。在一些实施例中，该装置可经配置使得电洞可自阳极传输至发光层。在一些实施例中，该装置可经配置使得电子可自阴极传输至发光层。若主体存在，则发光层中的主体的量可以改变。在一个实施例中，该发光层中的主体的量可在约1%至约99%的发光层重量的范围中。在另一实施例中，该发光层中的主体的量可在约90%至约99%的发光层重量的范围中。在另一实施例中，该发光层中的主体的量可占发光层重量的约97%。
在一些实施例中，该发光组件的质量可为该发光层质量的约0.1%至约10%、约1%至约5%、或约3%。在一些实施例中，该发光层可为单纯(neat)发光层，其表示此发光组件占发光层重量的约100%，或者说，发光层主要是由发光组件所组成。该发光组件可以是荧光及/或磷光化合物。在一些实施例中，该发光组件包括磷光材料。
该发光组件或化合物可经选择以用来改变该发光装置所发出的光的颜色。举例而言，一蓝色发光组件可发出一可见光子的组合，使得对观察者而言此光看起来具有一蓝色的性质。在一些实施例中，一蓝色发光组件可发出平均波长在约440纳米或约460纳米至约490纳米或约500纳米的范围中的可见光子。当提到化合物的可见光谱(visible emission spectrum)时，该可见光子的“平均波长”可包括在具有低于该平均波长的波长的可见光谱的部分曲线下的面积约等于在具有高于平均波长的波长的可见光谱的部分曲线下的面积的波长。可形成一蓝色发光组件的部分或全部的化合物的一些非限定实例包括含铱配位化合物(iridium coordination compound)，例如：吡啶甲酸双{2-[3,5-双(三氟甲基)苯基]吡啶根基-N,C2’}铱(III)(bis-{2-[3,5-bis(trifluoromethyl)phenyl]pyridinato-N,C2’}iridium(III)-picolinate)、吡啶甲酸双(2-[4,6-二氟苯基]吡啶根基-N,C2’)铱(III)(bis(2-[4,6-difluorophenyl]pyridinato-N,C2’)iridium(III)picolinate)、(乙酰丙酮酸)双(2-[4,6-二氟苯基]吡啶根基-N,C2’)铱(bis(2-[4,6-difluorophenyl]pyridinato-N,C2’)iridium(acetylacetonate))、双(4,6-二氟苯基吡啶根基)-3-(三氟甲基)-5-(吡啶-2-基)-1,2,4-三唑铱(III)(Iridium(III)bis(4,6-difluorophenylpyridinato)-3-(trifluoromethyl)-5-(pyridine-2-yl)-1,2,4-triazolate)、双(4,6-二氟苯基吡啶根基)-5-(吡啶-2-基)-1H-四唑铱(III)(Iridium(III)bis(4,6-difluorophenylpyridinato)-5-(pyridine-2-yl)-1H-tetrazolate)、四(1-吡唑基)硼酸双[2-(4,6-二氟苯基)吡啶根基-N,C2’]铱(III)(bis[2-(4,6-difluorophenyl)pyridinato-N,C2’]iridium(III)tetra(1-pyrazolyl)borate)等。
一红色发光组件可发出一可见光子的组合使得对于观察者而言此光看起来具有红色性质。在一些实施例中，一红色发光组件可发出平均波长在约600纳米、约620纳米或约651纳米至约780纳米或约800纳米的范围中的可见光子。可形成一红色发光组件的部分或全部的化合物的一些非限定实例包括含铱配位化合物，例如：(乙酰丙酮酸)双[2-(2’-苯并噻吩基)-吡啶根基-N,C3’]铱(III)(Bis[2-(2’-benzothienyl)-pyridinato-N,C3’]iridium(III)(acetylacetonate))、(乙酰丙酮酸)双[2-苯基喹啉基-N,C2’]铱(III)(Bis[(2-phenylquinolyl)-N,C2’]iridium(III)(acetylacetonate))、(乙酰丙酮酸)双[(1-苯基异喹啉根基-N,C2’)]铱(III)(Bis[(1-phenylisoquinolinato-N,C2’)]iridium(III)(acetylacetonate))、(乙酰丙酮酸)双[(二苯并[f,h]喹喏啉根基-N,C2’)铱(III)(Bis[(dibenzo[f,h]quinoxalino-N,C2’)]iridium(III)(acetylacetonate))、参(2,5-双-2’-(9’,9’-二己基茀)吡啶)铱(III)(Tris(2,5-bis-2’-(9’,9’-dihexylfluorene)pyridine)iridium(III))、参[1-苯基异喹啉根基-N,C2’]铱(III)(Tris[1-phenylisoquinolinato-N,C2’]iridium(III))、参-[2-(2’-苯并噻吩基)-吡啶根基-N,C3’]铱(III)(Tris-[2-(2’-benzothienyl)-pyridinato-N,C3’]iridium(III))、参[1-噻吩-2-基异喹啉根基-N,C3’]铱(III)(Tris[1-thiophen-2-ylisoquinolinato-N,C3’]iridium(III))以及参[1-(9,9-二甲基-9H-茀-2-基)异喹啉根基-(N,C3’)]铱(III)(Tris[1-(9,9-dimethyl-9H-fluoren-2-yl)isoquinolinato-(N,C3’)]iridium(III))等。
1.(Btp)2Ir(III)(acac)；(乙酰丙酮酸)双[2-(2’-苯并噻吩基)-吡啶根基-N,C3’]铱(III)。
2.(Pq)2Ir(III)(acac)；(乙酰丙酮酸)双[2-苯基喹啉基-N,C2’]铱(III)。
3.(Piq)2Ir(III)(acac)；(乙酰丙酮酸)双[(1-苯基异喹啉根基-N,C2’)]铱(III)。
4.(DBQ)2Ir(acac)；(乙酰丙酮酸)双[(二苯并[f,h]喹喏啉根基-N,C2’)铱(III)。
5.[Ir(HFP)3]，参(2,5-双-2’-(9’,9’-二己基茀)吡啶)铱(III)。
6.Ir(piq)3；参[1-苯基异喹啉根基-N,C2’]铱(III)。
7.Ir(btp)3；参-[2-(2’-苯并噻吩基)-吡啶根基-N,C3’]铱(III)。
8.Ir(tiq)3，参[1-噻吩-2-基异喹啉根基-N,C3’]铱(III)。
9.Ir(fliq)3；参[1-(9,9-二甲基-9H-茀-2-基)异喹啉根基-(N,C3’)]铱(III)。
一绿色发光组件可发出一可见光子的组合使得对于观察者而言此光看起来具有绿色性质。在一些实施例中，一绿色发光组件可发出平均波长在约490纳米、约500纳米或约501纳米至约570纳米或约600纳米的范围中的可见光子。可形成绿色发光组件的部分或全部的化合物的一些非限定实例包括含铱配位化合物，例如：(乙酰丙酮酸)双(2-苯基吡啶根基-N,C2’)铱(III)(Bis(2-phenylpyridinato-N,C2’)iridium(III)(acetylacetonate)，[Ir(ppy)2(acac)])、(乙酰丙酮酸)双(2-(4-甲苯基)吡啶根基-N,C2’)铱(III)(Bis(2-(4-tolyl)pyridinato-N,C2’)iridium(III)(acetylacetonate)，[Ir(mppy)2(acac)])、(乙酰丙酮酸)双[2-(4-第三丁基)吡啶根基-N,C2’]铱(III)(Bis(2-(4-tert-butyl)pyridinato-N,C2’)iridium(III)(acetylacetonate)，[Ir(t-Buppy)2(acac)])、参(2-苯基吡啶根基-N,C2’)铱(III)(Tris(2-phenylpyridinato-N,C2’)iridium(III)，[Ir(ppy)3])、(乙酰丙酮酸)双(2-苯基恶唑啉根基-N,C2’)铱(III)(Bis(2-phenyloxazolinato-N,C2’)iridium(III)(acetylacetonate)，[Ir(op)2(acac)])、参(2-(4-甲苯基)吡啶根基-N,C2’)铱(III)(Tris(2-(4-tolyl)pyridinato-N,C2’)iridium(III)，[Ir(mppy)3])等。
一橙色发光组件可发出一可见光子的组合使得对于观察者而言此光看起来具有橙色性质。在一些实施例中，一橙色发光组件可发出平均波长在约570纳米、约585纳米或约601纳米至约620纳米或约650纳米的范围中的可见光子。可形成一橙色发光组件的部分或全部的化合物的一些非限定实例包括含铱配位化合物，例如：(乙酰丙酮酸)双[2-苯基苯并噻唑根基-N,C2’]铱(III)(Bis[2-phenylbenzothiazolato-N,C2’]iridium(III)(acetylacetonate))、(乙酰丙酮酸)双[2-(4-第三丁基苯基)苯并噻唑根基-N,C2’]铱(III)(Bis[2-(4-tert-butylphenyl)benzothiazolato-N,C2’]iridium(III)(acetylacetonate))、(乙酰丙酮酸)双[(2-(2’-噻吩基)吡啶根基-N,C3’)]铱(III)(Bis[(2-(2’-thienyl)pyridinato-N,C3’)]iridium(III)(acetylacetonate))、参[2-(9.9-二甲基茀-2-基)吡啶根基-(N,C3’)]铱(III)(Tris[2-(9.9-dimethylfluoren-2-yl)pyridinato-(N,C3’)]iridium(III))、参[2-(9.9-二甲基茀-2-基)吡啶根基-(N,C3')]铱(III)(Tris[2-(9.9-dimethylfluoren-2-yl)pyridinato-(N,C3’)]iridium(III))、(乙酰丙酮酸)双[5-三氟甲基-2-[3-(N-苯基咔唑基)吡啶根基-N,C2’]]铱(III)(Bis[5-trifluoromethyl-2-[3-(N-phenylcarbzolyl)pyridinato-N,C2’]]iridium(III)(acetylacetonate))、(2-PhPyCz)2Ir(III)(acac)等。
该发光层的厚度可改变。在一个实施例中，一发光层的厚度可具有在约1纳米至约150纳米或约200纳米的范围。
在一些实施例中，该发光装置可发出白光。一发光层可经配置以发出白光，藉由包括一白光发射体(emitter)或包括一结合后的发光看起来为白色的有色发射体的组合。另外，一不同的有色发光层的组合可用以发出白光。
在一些实施例中，该有机组件可更包括置于该阳极与该发光层之间的一电洞传输层。该电洞传输层可包括至少一种电洞传输材料。在一些实施例中，该电洞传输材料包括经芳香族取代(aromatic-substituted)的胺、咔唑、聚乙烯咔唑(polyvinylcarbazole，PVK)(例如聚(9-乙烯咔唑))；聚茀树脂(polyfluorene)；聚茀树脂共聚物；聚(9,9-二-正-辛基茀-交替-苯并噻二唑)(poly(9,9-di-n-octylfluorene-alt-benzothiadiazole)；聚对苯(poly(paraphenylene))；聚[2-(5-氰基-5-甲基己基氧基)-1,4-伸苯基](poly[2-(5-cyano-5-methylhexyloxy)-1,4-phenylene])；联苯胺(benzidine)；苯二胺(phenylenediamine)；酞青金属错合物(phthalocyanine metal complex)；一聚乙炔(polyacetylene)；聚噻吩(polythiophene)；三苯胺(triphenylamine)；酞青铜(copper phthalocyanine)；1,1-双(4-双(4-甲基苯基)胺基苯基)环己烷(1,1-Bis(4-bis(4-methylphenyl)aminophenyl)cyclohexane)；2,9-二甲基-4,7-二苯基-1,10-啡啉(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline)；3,5-双(4-第三丁基-苯基)-4-苯基[1,2,4]三唑(3,5-Bis(4-tert-butyl-phenyl)-4-phenyl[1,2,4]triazole)；3,4,5-三苯基-1,2,3-三唑(3,4,5-Triphenyl-1,2,3-triazole)；4,4’,4’-参(3-甲基苯基苯基胺基)三苯胺(4,4’,4’-tris(3-methylphenylphenylamino)triphenylamine，MTDATA)；N,N’-双(3-甲基苯基)N,N’-二苯基-[1,1’-联苯]-4,4’-二胺(N,N’-bis(3-methylphenyl)N,N’-diphenyl-[1,1’-biphenyl]-4,4’-diamine，TPD)；4,4’-双[N-(萘基)-N-苯基-胺基]联苯(4,4’-bis[N-(naphthyl)-N-phenyl-amino]biphenyl，α-NPB)；4,4’,4”-三(咔唑-9-基)三苯胺(4,4’,4”-tris(carbazol-9-yl)-triphenylamine，TCTA)；4,4’-双[N,N’-(3-甲苯基)胺基]-3,3’-二甲基联苯(4,4’-bis[N,N’-(3-tolyl)amino]-3,3’-dimethylbiphenyl，HMTPD)；4,4’-N,N’-二咔唑-联苯(4,4’-N,N’-dicarbazole-biphenyl，CBP)；1,3-N,N-二咔唑-苯(1,3-N,N-dicarbazole-benzene，mCP)；双[4-(p,p’-二甲苯基-胺基)苯基]二苯基硅烷(Bis[4-(p,p’-ditolyl-amino)phenyl]diphenylsilane，DTASi)；2,2’-双(4-咔唑基苯基)-1,1’-联苯(2,2’-bis(4-carbazolylphenyl)-1,1’-biphenyl，4CzPBP)；N,N’,N”-1,3,5-三咔唑基苯(N,N’N”-1,3,5-tricarbazoloyl benzene，tCP)；N,N’-双(4-丁基苯基)-N,N’-双(苯基)联苯胺(N,N’-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine)；或类似物。
在一些实施例中，该有机组件可更包括一置于该阴极与该发光层之间的电子传输层。在一些实施例中，该电子传输层可包括本文所述的化合物，并可包括其它电子传输材料，例如：2-(4-联苯基)-5-(4-第三丁基苯基)-1,3,4-恶二唑(2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole，PBD)；1,3-双(N,N-第三丁基-苯基)-1,3,4-恶二唑(1,3-bis(N,N-t-butyl-phenyl)-1,3,4-oxadiazole，OXD-7)；1,3-双[2-(2,2’-联吡啶-6-基)-1,3,4-恶二唑-5-基]苯(1,3-bis[2-(2,2’-bipyridine-6-yl)-1,3,4-oxadiazo-5-yl]benzene)；3-苯基-4-(1’-萘基)-5-苯基-1,2,4-三唑(3-phenyl-4-(1’-naphthyl)-5-phenyl-1,2,4-triazole，TAZ)；2,9-二甲基-4,7-二苯基-啡啉(2,9-dimethyl-4,7-diphenyl-phenanthroline，浴铜灵(bathocuproine)或BCP)；参(8-羟基喹啉基)铝(aluminumtris(8-hydroxyquinolate)，Alq3)以及1,3,5-参(2-N-苯基苯并咪唑基)苯(1,3,5-tris(2-N-phenylbenzimidazolyl)benzene)；1,3-双[2-(2,2’-联吡啶-6-基)-1,3,4-恶二唑-5-基]苯(1,3-bis[2-(2,2’-bipyridine-6-yl)-1,3,4-oxadiazo-5-yl]benzene，BPY-OXD)；3-苯基-4-(1’-萘基)-5-苯基-1,2,4-三唑(3-phenyl-4-(1’-naphthyl)-5-phenyl-1,2,4-triazole，TAZ)，2,9-二甲基-4,7-二苯基-啡啉(2,9-dimethyl-4,7-diphenyl-phenanthroline，浴铜灵或BCP)以及1,3,5-参[2-N-苯基苯并咪唑-z-基]苯(1,3,5-tris[2-N-phenylbenzimidazol-z-yl]benzene，TPBI)。在一些实施例中，电子传输层可以是喹啉铝(Alq3)、2-(4-联苯基)-5-(4-第三丁基苯基)-1,3,4-恶二唑(PBD)、啡啉、喹喏啉(quinoxaline)、1,3,5-参[N-苯基苯并咪唑-z-基]苯(TPBI)或一衍生物或其组合。
若需要，发光装置中可包括额外的膜层。这些额外的膜层可包括一电子注入层(electron injection layer，EIL)、一电洞阻挡层(hole-blocking layer，HBL)、一激子阻挡层(exciton-blocking layer，EBL)及/或一电洞注入层(hole-injectionlayer，HIL)。除了分离的膜层之外，这些材料中有些可结合至单一膜层中。
在一些实施例中，该发光装置可包括在该阴极与该发光层之间的一电子注入层。在一些实施例中，该电子注入材料的最低未填满分子轨域(lowestunoccupied molecular orbital，LUMO)的能阶高到足以阻止其接收来自于该发光层的电子。在其它实施例中，该电子注入材料的LUMO与该阴极层的功函数之间的能量差异小到足以使该电子注入层能够有效地将电子从该阴极注入至该发光层中。若干合适的电子注入材料为该技术领域中普通技术人员所已知的。合适的电子注入材料的实例包括但不局限于一种视情况取代的化合物，选择自如下：掺杂至上述电子传输材料的LiF、CsF、Cs或其一衍生物或其组合。
在一些实施例中，该装置可包括例如在该阴极与该发光层之间的一电洞阻挡层。可包括于该电洞阻挡层中各种合适的电洞阻断材料为该技术领域中普通技术人员所已知。合适的电洞阻断材料包括但不局限于一种视情况取代的化合物，选择自如下：浴铜灵(BCP)、3,4,5-三苯基-1,2,4-三唑(3,4,5-triphenyl-1,2,4-triazole)、3,5-双(4-第三丁基-苯基)-4-苯基-[1,2,4]三唑(3,5-bis(4-tert-butyl-phenyl)-4-phenyl-[1,2,4]triazole)、2,9-二甲基-4,7-二苯基-1,10-啡啉(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)以及1,1-双(4-双(4-甲基苯基)胺基苯基)-环己烷(1,1-bis(4-bis(4-methylphenyl)aminophenyl)-cyclohexane)。
在一些实施例中，该发光装置可包括一激子阻挡层，其例如是在该发光层与该阳极之间。在一实施例中，该包括激子阻挡层的材料的能带间隙(bandgap energy)可大到足以实质上阻止激子的扩散。若干合适的可包括于该激子阻挡层中的激子阻断材料为该技术领域中普通技术人员所已知。可组成一激子阻挡层的材料的实例包括视情况取代的化合物，选择自如下：喹啉铝(Alq3)、4,4’-双[N-(萘基)-N-苯基-胺基]联苯(α-NPB)、4,4’-N,N’-二咔唑-联苯(CBP)以及浴铜灵(BCP)，以及任何其它具有大到足以实质上阻止激子扩散的能带间隙的材料。
在一些实施例中，该发光装置可包括在发光层与阳极之间的一电洞注入层。可包括于该电洞注入层中的各种合适的电洞注入材料为该技术领域中普通技术人员所已知。例示性电洞注入材料包括视情况取代的化合物，选择自如下：聚噻吩衍生物(例如：聚(3,4-伸乙基二氧基噻吩)(poly(3,4-ethylenedioxythiophene)，PEDOT)/聚苯乙烯磺酸(polystyrenesulphonic acid，PSS))、联苯胺衍生物(例如：N,N,N’,N’-四苯基联苯胺(N,N,N’,N’-tetraphenylbenzidine))、聚(N,N’-双(4-丁基苯基)-N,N’-双(苯基)联苯胺)(poly(N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine))、三苯基胺(triphenylamine)或苯二胺衍生物(例如：N,N’-双(4-甲基苯基)-N,N’-双(苯基)-1,4-苯二胺(N,N'-bis(4-methylphenyl)-N,N'-bis(phenyl)-1,4-phenylenediamine)、4,4’,4”-参(N-(伸萘-2-基)-N-苯基胺基)三苯胺(4,4’,4”-tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine))、恶二唑衍生物(例如：1,3-双(5-(4-二苯基胺基)苯基-1,3,4-恶二唑-2-基)苯(1,3-bis(5-(4-diphenylamino)phenyl-1,3,4-oxadiazol-2-yl)benzene))、聚乙炔衍生物(例如：聚(1,2-双-苯甲基硫基-乙炔)(poly(1,2-bis-benzylthio-acetylene)))以及酞青金属错合物衍生物(例如：酞青铜(CuPc))。在一些实施例中，虽然仍能够传输电洞，但电洞传输材料可具有实质上少于现有电洞传输材料的电洞迁移率(mobility)的电洞迁移率。
如本文提供的指南(guidance)所告知，可使用所属领域所公知的技术来制造包括本文所述的化合物的发光装置。举例而言，一玻璃基板可以一高功函数金属(例如：可作为阳极的ITO)来涂布。在图案化阳极层后，可在阳极上按照顺序沉积一电洞注入层及/或电洞传输层。包括一发光组件的一发光层可被沉积在该阳极、该电洞传输层或该电洞注入层上。该发光层可包括本文所述的化合物，及/或本文所述按照顺序沉积的一化合物可以是一电子传输层及/或一电子注入层的部分，或可以是一电子注入层及一电子传输层的部分。可接着沉积(例如：藉由气体沉积或溅镀)阴极层(包括一低功函数金属，例如：Mg:Ag)。该装置也可包括一激子阻挡层、一电子阻挡层、一电洞阻挡层、一第二发光层或其它可以使用合适的技术来添加至此装置的膜层。
图1所示为装置的一配置实例，该装置包括本文所述的化合物。该装置包括按照给定顺序的下述膜层：ITO/玻璃阳极5、PEDOT/PSS电洞注入层10、电洞传输层(NPB)15、发光层20、电子传输层(TPBI)30以及LiF/Al阴极35。
在一些实施例中，可藉由湿制程例如：包括喷涂法(spraying)、旋转涂布法(spin coating)、滴落涂布法(drop casting)、喷墨印刷法(inkjet printing)、网版印刷法(screen printing)等至少其中之一的制程来制作该OLED。一些实施例提供可适用于基板上沉积的液体的组合物。该液体可以为单一相或可包括分散于液体中的一或多个额外固相或液相。该液体一般而言包括一发光化合物、一本文所述的主体材料以及一溶剂。
下述为可用来制备本文所述的化合物的一些方法的实例。
实施例1有机合成
实施例1.1
实施例1.1.1
4-溴-N-(2-(苯基胺)苯基)苯甲酰胺(4-Bromo-N-(2-(phenylamino)phenyl)benzamide)(1)：将N-苯基苯-1,2-二胺(N-phenylbenzene-1,2-diamine)(10.2克，55毫莫耳)添加至含4-溴-苯酰氯(4-bromo-benzoyl chloride)(11克，50毫莫耳)的无水二氯甲烷(dichloromethane，DCM)(100毫升)溶液中，接着缓慢地添加三乙基胺(triethylamine，TEA)(17毫升，122毫莫耳)。于室温(room temperature，RT)搅拌此溶液过夜。过滤得到白色固体1(6.5克)。以水(300毫升)回溶过滤液，接着以DCM(300毫升)萃取三次。收集有机相以及以MgSO4干燥、浓缩以及于DCM/己烷中再结晶以得到另一部分白色固体1(10.6克)。产物1的总量为17.1克，产率为93%。
实施例1.1.2
2-(4-溴苯基)-1-苯基-1H-苯并咪唑(2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazole)(2)：缓慢地将氧氯化磷(phosphorus oxychloride，POCl3)(9.2毫升，100毫莫耳)添加至含酰胺1(9.6克，26毫莫耳)的无水1,4-二恶烷(1,4-dioxane)(100毫升)的悬浮液中。接着于100℃加热此溶液过夜。在冷却至室温(RT)后，将混合物以搅拌方式倒入至冰块(200克)中。过滤，随后于DCM/己烷中再结晶而得到灰白色固体2(8.2克，产率为90%)。
实施例1.1.3
1-苯基-2-(4-(4,4,5,5-四甲基-1,3,2-二氧杂硼戊环-2-基)苯基)-1H-苯并[d]咪唑(1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole)(3)：将含化合物2(0.70克，2毫莫耳)、联硼酸频那醇酯(bis(pinacolate)diborane)(0.533克，2.1毫莫耳)、[双(二苯基膦基)二茂铁]二氯化钯[bis(diphenylphosphino)ferrocene]dichloropalladium(Pd(dppf)Cl2)(0.060克，0.08毫莫耳)以及无水乙酸钾(potassium acetate)(KOAc)(0.393克，4毫莫耳)的1,4-二恶烷(20毫升)的混合物在氩气下于80℃加热过夜。在冷却至室温后，以乙酸乙酯(ethyl acetate)(80毫升)稀释此溶液接然后过滤。在硅胶(silica gel)上吸收此溶液，接着以管柱层析法(己烷/乙酸乙酯5：1到3：1)来纯化而得到白色固体3(0.64克，产率为81%)。
实施例1.1.4
N-(4’-溴-[1,1’-二苯基]-4-基)-N-苯基萘-1-胺(N-(4’-bromo-[1,1’-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine)(4)：将含N-苯基萘-1-胺(N-phenylnaphthalen-1-amine)(4.41克，20毫莫耳)、4,4’-二溴-1,1’-二苯基(4,4’-dibromo-1,1’-biphenyl)(15克，48毫莫耳)、第三丁氧化钠(sodiumtert-butoxide)(4.8克，50毫莫耳)以及Pd(dppf)Cl2(0.44克，0.6毫莫耳)的无水甲苯(toluene)(100毫升)的混合物脱气(degas)，且于80℃加热10小时。在冷却至室温后，将混合物倒进二氯甲烷(400毫升)中并搅拌30分钟，接着以盐水(brine)(100毫升)润洗。收集有机相且以Na2SO4干燥、装填至硅胶上以及以快速管柱(flash column)(己烷比己烷/乙酸乙酯90：1)来纯化以得到固体，此固体经甲醇润洗且在空气下干燥而得到白色固体4(5.58克，产率为62%)。
实施例1.1.5
主体-1(Host-1)：将含化合物3(0.80克，2毫莫耳)、化合物4(0.90，2毫莫耳)、肆(三苯基膦)钯(0)(tetrakis(triphenylphosphine)-palladium(0)，Pd(PPh3)4)(0.115克，0.1毫莫耳)以及碳酸钾(0.69克，5毫莫耳)的二恶烷/水(25毫升/5毫升)的混合物脱气且于100℃加热过夜。在冷却至室温后，以水及乙酸乙酯(150毫升×3)回溶混合物。收集有机相且以Na2SO4干燥、装填至硅胶上、以快速管柱(己烷/乙酸乙酯8：1到6：1)来纯化以得到白色固体(主体-1)(0.90克，产率为70%)。液相层析质谱仪(Liquid Chromatography MassSpectrometry，LCMS)数据：经计算C47H34N3(M+H)=640.3；发现：m/e=640。
实施例1.2
实施例1.2.1
N-苯基-N-(4’-(4,4,5,5-四甲基-1,3,2-二氧杂硼戊环-2-基)-[1,1’-二苯基]-4-基)萘-1-胺(N-phenyl-N-(4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-y1)-[1,1’-biphenyl]-4-yl)naphthalen-1-amine)(5)：将含化合物4(5.5克，12.2毫莫耳)、联硼酸频那醇酯(3.10克，12.2毫莫耳)、Pd(dppf)Cl2(0.446毫克，0.6毫莫耳)以及KOAc(5.5克，56毫莫耳)的无水二恶烷(60毫升)的混合物脱气且于80℃加热过夜。在冷却至室温后，将混合物倒进乙酸乙酯(200毫升)中，以盐水(150毫升)润洗。以Na2SO4干燥此有机溶液、装填至硅胶上以及以快速管柱(己烷比己烷/乙酸乙酯30:1)来纯化以收集主要部分。在溶剂移除后，此固体经甲醇润洗、过滤以及于空气中干燥而得到白色固体5(5.50克，产率为90%)。
实施例1.2.2
N-(4”-溴-[1,1’:4’,1”-三联苯基]-4-基)-N-苯基萘-1-胺(N-(4”-bromo-[1,1’:4’,1”-terphenyｌ]-4-yｌ)-N-phenyｌnaphthalen-1-amine)(6)：将含化合物5(4.5克，9.0毫莫耳)、1-溴-4-碘化苯(1-bromo-4-iodobenzene)(5.12克，18毫莫耳)、Pd(PPh3)4(0.52克，0.45毫莫耳)以及碳酸钾(4.436克，32毫莫耳)的二恶烷/水(150毫升/30毫升)的混合物脱气且于95℃加热过夜。在冷却至室温后，将混合物倒进二氯甲烷(300毫升)中，以盐水(150毫升)润洗。以Na2SO4干燥此有机溶液、接着装填至硅胶上以及以快速管柱(己烷比己烷/乙酸乙酯20：1)来纯化以得到亮黄色固体(4.30克，产率为90.7%)。
实施例123
主体-2：将含化合物6(4.21克，8.0毫莫耳)、化合物3(3.166克，8.0毫莫耳)、Pd(PPh3)4以及碳酸钾(3.31克，24毫莫耳)的二恶烷/水(150毫升/30毫升)的混合物脱气且于85℃加热18小时。在冷却至室温后，过滤此混合物。分别收集固体及过滤液。以二氯甲烷(250毫升)稀释过滤液且以盐水润洗。以Na2SO4干燥此有机相、装填至硅胶上以及以快速管柱(己烷比己烷/乙酸乙酯10：1到5：1到4：1)来纯化。收集主要所需的蓝色荧光部分，且其经浓缩而得到白色固体(0.55克，对应于目标分子量的m/e=716)。将来自第一次过滤的固体再溶解(redissolve)于二氯甲烷(200毫升)中、装填至硅胶上以及以快速管柱(己烷比己烷/乙酸乙酯4：1到二氯甲烷比己烷/乙酸乙酯3：1)来纯化以收集所需部分，其经浓缩至200毫升且于-10℃保存过夜。过滤白色沉淀物且于空气中干燥以得到松软白色固体(主体-2)(3.65克)。总产率为73%。LCMS数据：经计算C53H38N3(M+H)：716.3；发现m/e=716。
实施例1.3
实施例1.3.1
4’-溴-N,N-二对甲苯基联苯基-4-胺(4’-bromo-N,N-dip-tolylbiphenyl-4-amine)(7)：将二对甲苯基胺(di-p-tolylamine)(6.0克，30.4毫莫耳)、4,4’-二溴联苯(4,4’-dibromobiphenyl)(23.7克，76.0毫莫耳)、第三丁氧化钠(sodiumtert-butoxide)(7.26克，91.2毫莫耳)以及1,1-双(二苯基膦基)二茂铁二氯化钯(II)(Pd(dppf)Cl2)(666毫克，0.912毫莫耳，3莫耳%)添加至无水甲苯(约250毫升)以及于氩气中脱气，约30分钟。加热所产生的混合物至约80℃(约6小时)，之后经TLC分析指出已消耗大部分的二对甲苯基胺。在冷却至室温后，将混合物倒进饱和碳酸氢钠(sodium bicarbonate)水溶液中，且以两部分的乙酸乙酯萃取。汇集有机层并以水及盐水润洗，接着以MgSO4干燥。在过滤后，以旋转式蒸发器(rotary evaporator)将萃取物浓缩至干燥(dryness)，然后装填至硅胶上。快速管柱(100%己烷到含1%二氯甲烷(methylene chloride)的己烷的梯度)产生9.4克(72%)的白色固体化合物7，其是以三氯氘甲烷(CDCl3)之1H核磁共振(NMR)确认。
实施例1.3.2
4’-(4,4,5,5-四甲基-1,3,2-二氧杂硼戊环-2-基)-N,N-二对甲苯基-[1,1’-联苯基]-4-胺(4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N,N-di-p-toly1-[1,1'-biphenyl]-4-amine)(8)：将含化合物7(2.0克，4.67毫莫耳)、联硼酸频那醇酯(1.27克，5毫莫耳)、Pd(dppf)Cl2(0.18克，0.25毫莫耳)以及乙酸钾(0.98克，10毫莫耳)的无水二恶烷(50毫升)的混合物脱气以及于80℃加热16小时。在冷却至室温后，将溶液倒进乙酸乙酯(100毫升)中并过滤掉固体。将有机溶液装填至硅胶上，且以快速管柱(己烷/乙酸乙酯6：1)来纯化而得到白色固体8(1.5克，产率为68%)。
实施例1.3.3
4”-溴-N,N-二对甲苯基-[1,1’:4’,1’-三联苯基]-4-胺(4”-bromo-N,N-di-p-tolyl-[1,1’:4’,1”-terphenyl]-4-amine)(9)：将含化合物8(3.0克，6.3毫莫耳)、1-溴-4-碘化苯(3.57克，12.6毫莫耳)、Pd(PPh3)4以及碳酸钾(1.74克，12.6毫莫耳)的二恶烷/水(40毫升/8毫升)的混合物脱气以及于95℃加热24小时。在冷却至室温后，黄色固体经沉淀且藉由过滤收集。于二氯甲烷/甲醇中再结晶固体以得到灰黄色固体(2.22克)。将滤液装填至硅胶上，且以快速管柱来纯化而得到额外量的黄色固体9(0.42克)。总量为2.64克，产率为83%。
实施例1.3.4
主体-3：将含化合物9(1.5克，3毫莫耳)、化合物3(1.18克，3毫莫耳)、Pd(PPh3)4(0.173克，0.15毫莫耳)以及碳酸钾(1.38克，10毫莫耳)的二恶烷/水(40毫升/11毫升)的混合物脱气以及于100℃加热过夜。在冷却至室温后，将混合物倒进二氯甲烷(200毫升)中，然后以水(150毫升x2)润洗。以Na2SO4干燥有机溶剂、装填至硅胶上且以快速管柱(己烷/二氯甲烷2：1到己烷/乙酸乙酯9：1到5：1)来纯化以得到白色固体主体-3(1.1克，产率为52%)。LCMS数据：经计算C51H40N3(M+H)=694.3；发现m/e=694。
实施例1.4
实施例1.4.1
9-(4’-溴联苯基-4-基)-9H-咔唑(9-(4’-bromobiphenyl-4-yl)-9H-carbazole)(10)：将咔唑(300毫克，1.81毫莫耳)、4,4’-二溴联苯(4,4’-dibromobiphenyl)(846毫克，2.71毫莫耳)、铜(344毫克，5.43毫莫耳)、18-冠醚-6(18-crown-6)(187毫克，0.71毫莫耳)、碳酸钾(750毫克，5.43毫莫耳)以及无水N,N-二甲基甲酰胺(N,N-dimethylformamide)(10毫升)的混合物脱气30分钟。在氩气下于约155℃加热混合物66小时。在冷却至室温后，将混合物倒进二氯甲烷(400毫升)中及过滤后续混合物。将过滤液装填至硅胶上。快速管柱(二氧化硅，己烷中有10%二氯甲烷)以及于二氯甲烷/己烷中再沉淀(reprecipitation)产生304毫克(产率为42%)之纯产物10；经核磁共振氢谱(HNMR)确认。
实施例1.4.2
9-(4’-(4,4,5,5-四甲基-1,3,2-二氧杂硼戊环-2-基)-[1,1’-联苯基]-4-基)-9H-咔唑(9-(4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1’-biphenyl]-4-yl)-9H-carbazole)(11)：将含化合物10(2.0克，5.02毫莫耳)、联硼酸频那醇酯(1.276克，5.02毫莫耳)、Pd(dppf)Cl2(150毫克，0.20毫莫耳)以及乙酸钾(4.0克，41毫莫耳)的无水二恶烷(50毫升)的混合物脱气且于80℃加热过夜。在冷却室温后，将混合物倒进盐水，并以乙酸乙酯(200毫升)来萃取。有机相经收集并以Na2SO4干燥，接着装填至硅胶上，以快速管柱(己烷比己烷/二氯甲烷5：1到己烷比己烷/乙酸乙酯8：1)以提供白色固体11(1.50克，产率为67%)。
实施例1.4.3
2-(4’-溴-[1,1’-联苯基]-4-基)-1-苯基-1H-苯并[d]咪唑(2-(4’-bromo-[1,1’-biphenyl]-4-yl)-1-phenyl-1H-benzo[d]imidazole)(12)：将含化合物3(4.01克，10.1毫莫耳)、1-溴-4-碘化苯(5.73克，20.2毫莫耳)、Pd(PPh3)4(0.58克，0.5毫莫耳)以及碳酸钾(4.2克，30毫莫耳)的二恶烷/水(60毫升/10毫升)的混合物脱气且于95℃加热过夜。在冷却至室温后，过滤混合物以收集沉淀物，于热二氯甲烷中再溶解沉淀物。过滤二氯甲烷溶液并在甲醇存在的状况下浓缩，直到大量白色沉淀物形成为止。过滤及于空气中干燥而得到白色固体12(2.58克，产率为60%)。
实施例1.4.4
主体-4：将含化合物11(1.34克，3.01毫莫耳)、化合物12(1.28克，3.01毫莫耳)、肆(三苯基膦)钯(0)(Pd(PPh3)4)(0.173克，0.15毫莫耳)以及碳酸钾(1.38克，10毫莫耳)的二恶烷/水(80毫升/16毫升)的混合物脱气且于85℃加热过夜。在冷却至室温后，将混合物倒进二氯甲烷(30毫升)中，接着以盐水润洗两次。有机相经收集且经浓缩以产生沉淀。过滤悬浮液且分别收集固体以及过滤液并装填至硅胶上且以快速管柱(二氯甲烷比二氯甲烷/乙酸乙酯10：1)来纯化以得到白色固体主体-4(1.40克，总产率为70%)。LCMS数据：经计算
C49H34N3(M+H)：664.3；发现：m/e=664。
实施例2：OLED装置配置以及效能
实施例2.1(装置-A)
发光装置的制造：
以类似于下述的方式来制造一种装置(装置A)。依序以洗涤剂、水、丙酮然后异丙醇(isopropyl alcohol，IPA)来超音波清洗具有14奥姆/平方单位(ohm/sq)的片电阻(sheet resistance)的ITO基板；接着在大气环境下于80℃烘箱内干燥30分钟。接着在大气环境中以约200℃烘烤基板1小时，然后紫外线-臭氧(UV-ozone)处理约30分钟。接着以4000每分钟转速(rpm)将PEDOT：PSS(电洞注入材料)旋转涂布于退火的基板上约30秒。接着在大气环境下以约100℃烘烤涂布层30分钟，随后在手套箱(N2环境)内于200℃烘烤30分钟。接着将基板移至真空腔室内，其中在真空腔室内于2×10-7托耳的基本压力(base pressure)下以约0.1纳米/秒的速度来真空沉积4,4’-双[N-(萘基)-N-苯基-胺基]联苯(NPB)。分别以约0.01纳米/秒及约0.10纳米/秒共同沉积(co-deposite)双(1-苯基异喹啉)(乙酰丙酮酸)铱(III)(Bis(1-phenylisoquinoline)(acetylacetonate)iridium(III)，“Ir(piq)2acac”)(10重量百分比(wt%))与主体-2材料以作为发射层，以制作适当的厚度比。
接着以约0.1纳米/秒的速率将1,3,5-参(1-苯基-1H-苯并咪唑基)2-基)苯(TPBI)沉积于发射层上。以约0.005纳米/秒的速率沉积氟化锂(LiF)(电子注入材料)的膜层，随后以约0.3纳米/秒的速度沉积阴极(如：铝(Al))。代表性的装置结构为：ITO(约150纳米厚)/PEDOT：PSS(约30纳米厚)/NPB(约40纳米厚)/主体-2：Ir(piq)2acac(约30纳米厚)/TPBI(约30纳米厚)/LiF(约0.5纳米厚)/Al(约120纳米厚)。接着以附有吸气器(getter)的玻璃盖来封装此装置以覆盖OLED装置的发射区域(area)，以免受到潮湿、氧化或机械性损伤。
各个装置具有约12平方毫米的面积。
实施例2.2(装置-B以及-C)
除了使用双(苯基喹啉)乙酰丙酮酸铱(bis(phenylquinoline)iridiumacetylacetonate(Ir(PQ)2acac))(6wt%)与各主体材料取代Ir(piq)2acac来作为发光错合物(complex)之外，根据实例2.1建构其它装置，其中Ir(PQ)2acac发出600纳米的峰值波长；而ITO厚度为55纳米而非150纳米。发射体及主体的沉积速率分别为0.006纳米/秒以及0.1纳米/秒。
装置B及C的代表性装置结构为：ITO(约55纳米厚)/PEDOT：PSS(约30纳米厚)/NPB(约40纳米厚)/主体-2或主体-1：Ir(PQ)2acac(约30纳米厚)/TPBI(约40纳米厚)/LiF(约0.5纳米厚)/Al(约120纳米厚)。在无封装的状况下，于充填氮气的手套箱内量测各个装置。
各个装置具有约9平方毫米的面积。
实施例2.3
除了分别于NPB的顶面上共同沉积化合物主体-3(94%)以及双(2-苯基喹啉-N,C2’)乙酰丙酮酸铱(III)(Ir(PQ)2acac)的混合物、化合物主体-4(94%)以及双(2-苯基喹啉-N,C2’)乙酰丙酮酸铱(III)(Ir(PQ)2acac)的混合物、比较化合物X(4”-(1-苯基-1H-苯并[d]咪唑-2-基)-N,N-二对甲苯基-[1,1’:4’,1”-三联苯基]-4-胺(4”-(1-phenyl-1H-benzo[d]imidazol-2-yl)-N,N-di-p-tolyl-[1,1’:4’,1”-terphenyl]-4-amine)(94%)、以及双(2-苯基喹啉-N,C2’)乙酰丙酮酸铱(III)(Ir(PQ)2acac)(6%)的混合物、以及比较化合物Y(4,4’-双[N-(萘基)-N-苯基-胺基]联苯(NPB)(94%)、以及双(2-苯基喹啉-N,C2’)乙酰丙酮酸铱(III)(Ir(PQ)2acac)(6%)的混合物来取代化合物主体-1(94%)以及双(2-苯基喹啉-N,C2’)乙酰丙酮酸铱(III)(bis(2-phenyl quinolyl-N,C2’)acetylacetonateiridium(III)(Ir(PQ)2acac))(6%)的混合物之外，根据实例2.2建构其它装置(装置D[主体-3]、装置E[主体-4]、比较装置X[主体-X]以及比较装置Y[NPB])，以形成厚度30纳米的发光层20。
各个装置具有约9平方毫米的面积。
实施例3：装置效能
实施例3.1
以PR670来量测所有光谱，以及以吉时利(Keithley)2400电源测定装置(SourceMeter)(吉时利仪器公司，美国俄亥俄州，克利夫兰)来获得I-V-L特性。于填充氮气的手套箱内执行所有装置操作。
如图2至图6所示，藉由检查为驱动电压的函数的电流密度及亮度来测试装置A(红色发光装置，其包括主体-2：Ir(piq)2acac且是根据实例1及2所制作)，以决定装置的发旋光性质。装置的开启电压约为2.5伏特，而在约8V时的最大亮度约为39,700烛光/平方公尺(面积12平方毫公尺的装置)。于1000烛光/平方公尺时的装置的EQE(external quantum efficiency，外部量子效率)、发光效率以及功率效率在630纳米的发光下约为15.5%、12.6烛光/安培以及10.4流明/瓦。装置B及C(红色发光装置)分别包括主体-2：Ir(PQ)2acac及主体-1：Ir(PQ)2acac，且是根据实例1及2所制作。图7为装置B的电激发光(electroluminescence)光谱。如图8至图13所示，检查为驱动电压函数的电流密度及亮度来测试装置B及C，以确认装置的发旋光性质。面积9平方毫米的装置的开启电压约为2.5伏特。对于含有主体-2：Ir(PQ)2acac(6wt%)的发光层的装置，装置B在1000烛光/平方米的EQE(外部量子效率)、发光效率以及功率效率约为16.2%、30.3烛光/安培以及26.6流明/瓦，而对于含有主体-1：Ir(PQ)2acac(6wt%)的发光层的装置(装置C)则为EQE=15.4%、LE=27.8烛光/安培、PE=24流明/瓦。表1表示根据实例2.1、2.2以及2.3所制作的装置的各装置的功率效率以及发光效率。
表1
| 装置 | PE(流明/瓦) | LE(烛光/安培) |
| 装置A | 10.4 | 12.3 |
| 装置B | 24 | 27.8 |
| 装置C | 26.6 | 30.3 |
| 装置D | 32.8 | 35.6 |
| 装置E | 5.83 | 9.29 |
| 装置X | 28 | 30.9 |
| 装置Y | 4.44 | 5.51 |
因此化合物主体-1及主体-2已证明其在有机发光装置中可作为有效主体材料。
实施例3.2
测试装置B及C(分别包括主体-2:Ir(PQ)2acac及主体-1:Ir(PQ)2acac，且根据实例2.2所制造的发光装置)以决定装置寿命(于5000尼特(nit)下的T50(h))。以PR670来量测所有光谱，且以吉时利2400电源测定装置(吉时利仪器公司，美国俄亥俄州，克利夫兰)来获得I-V-L特性。在无封装的状况下，于填充氮气的手套箱内执行所有装置操作。
表2表示根据实例2.1、2.2以及2.3所制作的装置的装置寿命。
表2
| 装置 | 于500尼特的T50(h) |
| 装置A | 1150 |
| 装置B | 1000 |
| 装置C | 700 |
| 装置D | 80 |
| 装置E | 200 |
| 比较装置X | 36 |
| 比较装置Y | 1.3 |
故，至少主体-1及主体-2已证明其作为发光有机发光装置中的一持久性化合物的效果。
该技术领域普通技术人员应理解到，可在不背离本发明的精神下来制造各种不同修饰。因此，应清楚理解到本发明的形式仅供说明而不意欲限制本发明的范畴。
Claims (10)
1.一种化合物，选自于由：
所组成的群组。
2.如权利要求1所述的化合物，以下式表示：
3.如权利要求1所述的化合物，以下式表示：
4.如权利要求1所述的化合物，以下式表示：
5.如权利要求1所述的化合物，以下式表示：
6.一种发光装置，包含如权利要求1至5中任一项所述的化合物。
7.如权利要求6所述的发光装置，其中该化合物是在一发光层中的一主体。
8.如权利要求7所述的发光装置，其中该发光层更进一步包含：
及
9.如权利要求7所述的发光装置，更进一步包含一电洞传输层，置于该发光层与一阳极之间。
10.如权利要求7所述的发光装置，更进一步包含一电子传输层，置于该发光层与一阴极之间。
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| JP5970475B2 (ja) * | 2011-01-27 | 2016-08-17 | 日東電工株式会社 | 場合によっては置換されているテルフェニルおよびクアテルフェニル化合物を含有する光線療法装置および方法 |
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Also Published As
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|---|---|
| US20130146856A1 (en) | 2013-06-13 |
| TW201231458A (en) | 2012-08-01 |
| EP2655338A1 (en) | 2013-10-30 |
| CN103502223B (zh) | 2015-09-30 |
| US9373797B2 (en) | 2016-06-21 |
| US8426040B2 (en) | 2013-04-23 |
| KR20140035316A (ko) | 2014-03-21 |
| US20110140093A1 (en) | 2011-06-16 |
| WO2012088294A1 (en) | 2012-06-28 |
| EP2655338B1 (en) | 2016-02-24 |
| TWI557114B (zh) | 2016-11-11 |
| JP5805209B2 (ja) | 2015-11-04 |
| JP2014502966A (ja) | 2014-02-06 |
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