CN104755462A - 新颖有机电致发光化合物和含有所述化合物的有机电致发光装置 - Google Patents
新颖有机电致发光化合物和含有所述化合物的有机电致发光装置 Download PDFInfo
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- CN104755462A CN104755462A CN201380052310.1A CN201380052310A CN104755462A CN 104755462 A CN104755462 A CN 104755462A CN 201380052310 A CN201380052310 A CN 201380052310A CN 104755462 A CN104755462 A CN 104755462A
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- unsubstituted
- aryl
- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 90
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 18
- -1 nitro, hydroxyl Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 229910052796 boron Inorganic materials 0.000 claims description 11
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910000077 silane Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000006073 displacement reaction Methods 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 150000001343 alkyl silanes Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 238000006884 silylation reaction Methods 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 4
- 239000000463 material Substances 0.000 description 57
- 239000010410 layer Substances 0.000 description 52
- 239000002585 base Substances 0.000 description 31
- 239000002019 doping agent Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000005540 biological transmission Effects 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000000151 deposition Methods 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 150000004646 arylidenes Chemical group 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
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- 230000003245 working effect Effects 0.000 description 3
- 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 2
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- XZVNKEAPHZSYCJ-UHFFFAOYSA-N 4-[4-amino-4-(4-phenylphenyl)cyclohexa-1,5-dien-1-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=CCC(N)(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 XZVNKEAPHZSYCJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
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- 230000004888 barrier function Effects 0.000 description 2
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- 239000004327 boric acid Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
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- 230000005525 hole transport Effects 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- ANYCDYKKVZQRMR-UHFFFAOYSA-N lithium;quinoline Chemical compound [Li].N1=CC=CC2=CC=CC=C21 ANYCDYKKVZQRMR-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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Abstract
本发明涉及一种新颖的有机电致发光化合物和一种含有所述化合物的有机电致发光装置。通过使用根据本发明的有机电致发光化合物,有机电致发光装置可具有高发光效率、长寿命和高电流效率。
Description
技术领域
本发明涉及新颖有机电致发光化合物和含有所述化合物的有机电致发光装置。
背景技术
电致发光(EL)装置是自动发光装置,其优点在于其提供较宽的视角、较大的对比率和较快的响应时间。有机EL装置最初由伊士曼柯达(Eastman Kodak)通过使用小芳香族二胺分子和铝络合物作为用于形成发光层的材料而开发[应用物理学报(Appl.Phys.Lett.)51,913,1987]。
决定有机EL装置中的发光效率的最重要因素是发光材料。迄今为止,荧光材料已经广泛用作发光材料。然而,鉴于电致发光机制,由于磷光材料在理论上与荧光材料相比使发光效率增强四(4)倍,磷光发光材料的开发得到广泛研究。铱(III)错合物已广泛地被称为磷光材料,包括分别作为发红光、绿光和蓝光的材料的双(2-(2′-苯并噻吩基)-吡啶根-N,C3′)铱(乙酰基丙酮酸盐)((acac)Ir(btp)2)、三(2-苯基吡啶)铱(Ir(ppy)3)和双(4,6-二氟苯基吡啶根-N,C2)吡啶甲酸铱(Firpic)。
发光材料可以主体材料和掺杂剂的组合形式使用来改进色纯度、发光效率和稳定性。当使用主体材料/掺杂剂系统作为发光材料时,主体材料极大地影响EL装置的效率和性能,且因此其选择是至关重要的。目前,4,4′-N,N′-二咔唑-联二苯(CBP)是关于磷光材料最广泛已知的主体材料。最近,先锋(Pioneer)(日本)等人开发了使用浴铜灵(BCP)和铝(III)双(2-甲基-8-喹啉盐)(4-苯基苯酚盐)(BAlq)等作为主体材料的高性能有机EL装置,所述主体材料被称为空穴阻挡材料。
尽管这些磷光主体材料提供良好发光特征,但其具有以下缺点:(1)归因于其低玻璃转化温度和不良热稳定性,其降解可在真空中在高温沉积工艺期间出现。(2)所述有机EL装置的功率效率是通过[(π/电压)×电流效率]给出,且所述功率效率与电压成反比。尽管包含磷光主体材料的有机EL装置提供高于包含荧光材料的有机EL装置的电流效率(cd/A),但显著高驱动电压是必需的。因此,不存在关于功率效率(lm/W)的优点。(3)此外,所述有机EL装置的使用寿命很短,且仍需要改进发光效率。
同时,铜酞菁(CuPc)、4,4′-双[N-(1-萘基)-N-苯基氨基]联二苯(NPB)、N,N′-二苯基-N,N′-双(3-甲基苯基)-(1,1′-联苯基)-4,4′-二胺(TPD)、4,4′,4″-三(3-甲基苯基苯基氨基)三苯胺(MTDATA)等用作空穴注入和传输材料。然而,使用这些材料的有机EL装置在量子效率和使用寿命方面是有问题。这是因为,当所述有机EL装置在高电流下驱动时,在阳极和空穴注入层之间出现热应力。热应力显著减少所述装置的使用寿命。此外,由于用于空穴注入层的有机材料具有极高空穴迁移率,空穴-电子电荷平衡可被打破且量子产率(cd/A)可降低。
韩国专利申请案特许公开第2011-0117168号揭露用于有机EL装置的基于胺的化合物,其具有连接到两个或更多个选自二苯并呋喃基、咔唑基和噻吩基(经由芳基)的杂芳基环的取代基。然而,以上参考文献未能具体地揭露具有其中咔唑基的氮原子连接到二苯并噻吩基或芴基(经由芳基或杂芳基)的取代基的基于胺的化合物。
发明内容
技术问题
本发明的目标是提供一种有机电致发光化合物,其可提供与常规装置相比具有较高发光效率和较长寿命的有机电致发光装置,且提供包含所述化合物的有机电致发光装置,其具有高效率和长寿命。
问题的解决方案
本发明人发现以上目标可通过由下式1表示的化合物实现:
其中
L1和L2各自独立地表示单键、被取代或未被取代的(C6-C30)亚芳基或被取代或未被取代的5到30元亚杂芳基;
Ar1和Ar2各自独立地表示被取代或未被取代的(C6-C30)芳基或被取代或未被取代的5到30元杂芳基;
Ar1和L2可与其上键结的氮原子键联在一起以形成含氮5或30元杂芳基;
X表示-S-或-C(R5)(R6)-;
R1到R6各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、被取代或未被取代的(C1-C30)烷基、被取代或未被取代的(C2-C30)烯基、被取代或未被取代的(C2-C30)炔基、被取代或未被取代的(C1-C30)烷氧基、被取代或未被取代的(C3-C30)环烷基、被取代或未被取代的(C3-C30)环烯基、被取代或未被取代的3到7元杂环烷基、被取代或未被取代的(C6-C30)芳基、被取代或未被取代的5到30元杂芳基、-NR11R12、-SiR13R14R15、-SR16、-OR17、-COR18或-B(OR19)(OR20);或可键联到相邻取代基以形成单环或多环、3到30元脂环或芳环,所述环的碳原子可用至少一个选自氮、氧和硫的杂原子置换;
R11到R20各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、被取代或未被取代的(C1-C30)烷基、被取代或未被取代的(C2-C30)烯基、被取代或未被取代的(C2-C30)炔基、被取代或未被取代的(C1-C30)烷氧基、被取代或未被取代的(C3-C30)环烷基、被取代或未被取代的(C3-C30)环烯基、被取代或未被取代的3到7元杂环烷基、被取代或未被取代的(C6-C30)芳基或被取代或未被取代的5到30元杂芳基;或可键联到相邻取代基以形成单环或多环、3到30元脂环或芳环,所述环的碳原子可用至少一个选自氮、氧和硫的杂原子置换;
a和c各自独立地表示1到4的整数,其中a或c是2或大于2的整数,各R1或各R3是相同或不同的;
b和d各自独立地表示1到3的整数,其中b或d是2或大于2的整数,各R2或各R4是相同或不同的;
所述(亚)杂芳基含有至少一个选自B、N、O、S、P(=O)、Si和P的杂原子;
所述杂环烷基含有至少一个选自O、S和N的杂原子;且
其条件是在X为-C(R5)(R6)-的情况下,通过Ar1和L2的键联所形成的杂芳基不是咔唑环。
本发明的有利作用
根据本发明的有机电致发光化合物显示高发光效率和长寿命。通过使用根据本发明的化合物,电致发光装置可在低驱动电压下操作且具有电流效率和寿命的改进。
具体实施方式
在下文中,将对本发明进行详细描述。然而,以下描述旨在解释本发明,并且不打算以任何方式限制本发明的范围。
本发明提供以上式1的有机电致发光化合物、包含所述化合物的有机电致发光材料和包含所述材料的有机电致发光装置。
具体来说,本发明的式1化合物如下。
在以上式1中,优选地,L1和L2各自独立地表示单键、被取代或未被取代的(C6-C20)亚芳基或被取代或未被取代的5到21元亚杂芳基;Ar1和Ar2各自独立地表示被取代或未被取代的(C6-C20)芳基或被取代或未被取代的5到21元杂芳基;R1到R6各自独立地表示氢、卤素、被取代或未被取代的(C1-C15)烷基、被取代或未被取代的(C6-C30)芳基、被取代或未被取代的5到30元杂芳基、-NR11R12或SiR13R14R15;R11和R12各自独立地表示被取代或未被取代的(C6-C15)芳基;且R13到R15各自独立地表示被取代或未被取代的(C1-C10)烷基。
在以上式1中,更优选地,L1和L2各自独立地表示单键、未被取代的(C6-C18)亚芳基、被(C1-C6)烷基取代的(C6-C18)亚芳基或未被取代的5到10元亚杂芳基;Ar1和Ar2各自独立地表示未被取代的(C6-C18)芳基、被(C1-C6)烷基取代的(C6-C18)芳基、(C6-C20)芳基、(C1-C6)烷基(C6-C20)芳基、二(C6-C20)芳基氨基、(C6-C20)芳基(5到21元)杂芳基氨基或5到21元杂芳基、未被取代的5到15元杂芳基或被(C1-C6)烷基取代的5到15元杂芳基、(C6-C20)芳基、(C1-C6)烷基(C6-C20)芳基或二(C6-C20)芳基氨基;且R1到R6各自独立地表示氢、卤素、未被取代的(C1-C6)烷基、被(C1-C6)烷基取代的硅烷基、未被取代或被(C1-C6)烷基取代的(C6-C20)芳基或未被取代的5到21元杂芳基。
在本文中,“(C1-C30)烷基”指示具有1到30个、优选地1到10个碳原子的直链或分支链烷基且包括甲基、乙基、正丙基、异丙基、正丁基、异丁基叔丁基等。“(C2-C30)烯基”指示具有2到30个、优选地2到20个或更优选地2到10个碳原子的直链或分支链烯基且包括乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等。“(C2-C30)炔基”指示具有2到30个、优选地2到20个或更优选地2到10个碳原子的直链或分支链炔基且包括乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等。“(C3-C30)环烷基”指示具有3到30个、优选地3到20个或更优选地3到7个碳原子的单环或多环烃且包括环丙基、环丁基、环戊基、环己基等。“3到7元杂环烷基”指示具有3到7个环主链原子(包括至少一个选自B、N、O、S、P(=O)、Si和P,优选地O、S和N的杂原子)的环烷基,且包括四氢呋喃、吡咯烷、硫杂环戊烷、四氢吡喃等。此外,“(亚)(C6-C30)芳基”指示源自芳香族烃且具有6到30个、优选地6到15个环主链碳原子的单环或稠环,且包括苯基、联苯基、三联苯、萘基、芴基、菲基、蒽基、茚基、三亚苯基、芘基、并四苯基、苝基、屈基、稠四苯基、荧蒽基等。“5到30元(亚)杂芳基”指示具有5到30个、优选地5到15个环主链原子(包括至少一个、优选地1到4个选自由B、N、O、S、P(=O)、Si和P组成的群组的杂原子)的芳基;可为单环或与至少一个苯环稠合的稠环;可为部分饱和的;可为通过使至少一个杂芳基或芳基经由单键键联到杂芳基所形成的基团;并且包括单环型杂芳基,如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋吖基、吡啶基、吡嗪基、嘧啶基、哒嗪基等,和稠环型杂芳基,如苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喔啉基、咔唑基、啡噁嗪基、啡啶基、苯并间二氧杂环戊烯基等。此外,“卤素”包括F、Cl、Br和I。
本文中,表述“被取代或未被取代的”中的“被取代的”意指某一官能团中的氢原子被另一个原子或基团(即取代基)置换。以上式1中的被取代的烷基、被取代的烯基、被取代的炔基、被取代的烷氧基、被取代的环烷基、被取代的环烯基、被取代的杂环烷基、被取代的(亚)芳基和被取代的(亚)杂芳基的取代基各自独立地优选地为选自由以下组成的群组的至少一者:氘、卤素、氰基、羧基、硝基、羟基、(C1-C30)烷基、卤基(C1-C30)烷基、(C2-C30)烯基、(C2-C30)炔基、(C1-C30)烷氧基、(C1-C30)烷硫基、(C3-C30)环烷基、(C3-C30)环烯基、3到7元杂环烷基、(C6-C30)芳氧基、(C6-C30)芳基硫基、未被取代或被(C6-C30)芳基取代的5到30元杂芳基、未被取代或被5到30元杂芳基取代的(C6-C30)芳基、三(C1-C30)烷基硅烷基、三(C6-C30)芳基硅烷基、二(C1-C30)烷基(C6-C30)芳基硅烷基、(C1-C30)烷基二(C6-C30)芳基硅烷基、氨基、单或二(C1-C30)烷基氨基、单或二(C6-C30)芳基氨基、(C1-C30)烷基(C6-C30)芳基氨基、(C6-C30)芳基(5到30元)杂芳基氨基、(C1-C30)烷基羰基、(C1-C30)烷氧羰基、(C6-C30)芳基羰基、二(C6-C30)芳基硼羰基、二(C1-C30)烷基硼羰基、(C1-C30)烷基(C6-C30)芳基硼羰基、(C6-C30)芳基(C1-C30)烷基和(C1-C30)烷基(C6-C30)芳基。
本发明化合物包括以下(但不限于此):
本发明化合物可通过所属领域的技术人员已知的合成方法制备。例如,其可根据以下反应方案1或2制备。
[反应方案1]
[反应方案2]
在以上反应方案1和2中,X、L1、L2、Ar1、Ar2、R1到R4、a、b、c和d是如以上式1中定义,且Hal表示卤素。
此外,本发明提供包含式1的有机电致发光化合物的有机电致发光材料,和包含所述材料的有机电致发光装置。所述材料可由式1的有机电致发光化合物组成。另外,所述材料可进一步包含除式1化合物之外有机电致发光装置还已经包含的常规化合物。所述有机电致发光装置可包含第一电极、第二电极和至少一个安置于所述第一和第二电极之间的有机层。所述有机层可包含至少一种式1化合物。
第一和第二电极中的一者可为阳极,且另一者可为阴极。所述有机层可包含发光层,且可进一步包含至少一个选自空穴注入层、空穴传输层、电子传输层、电子注入层、夹层、空穴阻挡层和电子阻挡层的层。
式1化合物可包含于发光层和空穴传输层中的至少一者中。当用于空穴传输层中时,式1化合物可作为空穴传输材料包含在内。当用于发光层中时,式1化合物可作为主体材料包含在内;优选地,发光层可进一步包含至少一种掺杂剂,且必要时,除式1化合物外的化合物可另外作为第二主体材料包含在内。
第二主体材料可来自任何已知磷光主体材料。具体来说,鉴于发光效率,选自由以下式2到4的化合物组成的群组的材料优选作为第二主体材料。
H-(Cz-L4)h-M ----------(2)
H-(Cz)i-L4-M ----------(3)
其中,Cz表示以下结构:
R21到R24各自独立地表示氢、氘、卤素、被取代或未被取代的(C1-C30)烷基、被取代或未被取代的(C6-C30)芳基、被取代或未被取代的5到30元杂芳基或R25R26R27Si-;R25到R27各自独立地表示被取代或未被取代的(C1-C30)烷基或被取代或未被取代的(C6-C30)芳基;L4表示单键、被取代或未被取代的(C6-C30)亚芳基或被取代或未被取代的5到30元亚杂芳基;M表示被取代或未被取代的(C6-C30)芳基或被取代或未被取代的5到30元杂芳基;Y1和Y2表示-O-、-S-、-N(R31)-或-C(R32)(R33)-,其条件是Y1和Y2并不同时存在;R31到R33各自独立地表示被取代或未被取代的(C1-C30)烷基、被取代或未被取代的(C6-C30)芳基或被取代或未被取代的5到30元杂芳基,且R32和R33可相同或不同;h和i各自独立地表示1到3的整数;j、k、l和m各自独立地表示0到4的整数,且其中h、i、j、k、l或m是2或大于2的整数,各(Cz-L4)、各(Cz)、各R21、各R22、各R23或各R24可相同或不同。
具体来说,第二主体材料包括以下:
用于本发明的有机电致发光装置的掺杂剂优选地是至少一种磷光掺杂剂。用于本发明的有机电致发光装置的磷光掺杂剂不受限制,但可优选地选自铱(Ir)、锇(Os)、铜(Cu)和铂(Pt)的金属化错合物化合物,更优选地选自铱(Ir)、锇(Os)、铜(Cu)和铂(Pt)的邻位金属化错合物化合物,且甚至更优选地为邻位金属化铱错合物化合物。
磷光掺杂剂可优选地选自由以下式5到7表示的化合物。
其中L是选自以下:
R100表示氢或被取代或未被取代的(C1-C30)烷基;R101到R109和R111到R123各自独立地表示氢、氘、卤素、未被取代或被卤素取代的(C1-C30)烷基、氰基或被取代或未被取代的(C1-C30)烷氧基;或R120到R123可与相邻取代基键联以形成稠环,例如喹啉;R124到R127各自独立地表示氢、氘、卤素、被取代或未被取代的(C1-C30)烷基或被取代或未被取代的(C6-C30)芳基;在R124到R127为芳基的情况下,其可与相邻取代基键联以形成稠环,例如芴;R201到R211各自独立地表示氢、氘、卤素或未被取代或被卤素取代的(C1-C30)烷基;f和g各自独立地表示1到3的整数;在f或g为2或大于2的整数的情况下,各R100可相同或不同;且n是1到3的整数。
具体来说,磷光掺杂剂材料包括以下:
此外,本发明提供用于制备有机电致发光装置的材料。所述材料包含本发明化合物作为主体材料或空穴传输材料。当本发明化合物作为主体材料包含在内时,用于制备有机电致发光装置的材料可进一步包含第二主体材料,其中第一主体材料与第二主体材料的比率可在1∶99到99∶1范围内。
此外,本发明的有机电致发光装置包含第一电极、第二电极和至少一个安置于所述第一和第二电极之间的有机层。所述有机层包含用于制备本发明的有机电致发光装置的材料。
本发明的有机电致发光装置的有机层除式1化合物之外可进一步包含至少一种选自由基于芳基胺的化合物和基于苯乙烯基芳基胺的化合物组成的群组的化合物。
在本发明的有机电致发光装置中,所述有机层除式1化合物之外可进一步包含至少一种选自由以下组成的群组的金属:周期表的第1族金属、第2族金属、第4周期过渡金属、第5周期过渡金属、镧系元素和d-过渡元素的有机金属,或包含所述金属的至少一种错合物化合物。所述有机层可包含发光层和电荷产生层。
此外,本发明的有机电致发光装置可通过进一步包含至少一个发光层而发射白光,所述发光层除本发明化合物以外还包含所属领域中已知的蓝光电致发光化合物、红光电致发光化合物或绿光电致发光化合物。此外,必要时,所述装置中可包含发黄光或橙光层。
根据本发明,至少一个层(下文中,“表面层”)可位于一个或两个电极的内表面上,选自硫族化物层、金属卤化物层和金属氧化物层。具体来说,硅或铝的硫族化物(包括氧化物)层优选地位于电致发光中间层的阳极表面上,且金属卤化物层或金属氧化物优选地位于电致发光中间层的阴极表面上。此类表面层针对有机电致发光装置提供操作稳定性。优选地,硫族化物包括SiOX(1≤X≤2)、AlOX(1≤X≤1.5)、SiON、SiAlON等;金属卤化物包括LiF、MgF2、CaF2、稀土金属氟化物等;且金属氧化物包括Cs2O、Li2O、MgO、SrO、BaO、CaO等。
在本发明的有机电致发光装置中,电子传输化合物和还原性掺杂剂的混合区域、或空穴传输化合物和氧化性掺杂剂的混合区域可位于一对电极的至少一个表面上。在这种情况下,电子传输化合物被还原为阴离子,并且因此变得更容易从混合区域喷射并且传输电子到电致发光媒介。此外,空穴传输化合物被氧化为阳离子,并且因此变得更容易从混合区域喷射并且传输空穴到电致发光媒介。优选地,氧化性掺杂剂包括各种路易斯酸(Lewis acid)和受体化合物;并且还原性掺杂剂包括碱金属、碱金属化合物、碱土金属、稀土金属和其混合物。还原性掺杂剂层可用作电荷产生层以制备具有两个或更多个电致发光层并且发射白光的电致发光装置。
为了形成本发明的有机电致发光装置的每一层,可使用干式成膜方法,如真空蒸发、溅射、等离子体和离子电镀方法;或湿式成膜方法,如旋涂、浸涂和流涂方法。
下文中,将参考以下实例详细地解释本发明化合物、所述化合物的制备方法和所述装置的发光特性。
实例1:制备化合物C-37
制备化合物1-1
3-溴咔唑(10.6g,178mmol)、三苯基胺-4-硼酸(15g,52mmol)、四(三苯基膦)钯(0)[Pd(PPh3)4](2.5g,2.2mmol)、K2CO3(14g,104mmol)、甲苯(150mL)、乙醇(50mL)和水(50mL)的混合物在圆底烧瓶中搅拌且回流持续4小时。在用乙酸乙酯(EA)/H2O处理之后,反应混合物用MgSO4干燥且在减压下蒸馏。粗产物用柱色谱法使用二氯甲烷(MC):己烷(Hx)纯化以获得化合物1-1(白色固体,11g,62%)。
制备化合物1-2
化合物1-1[4-(9H-咔唑-3-基)-N,N-二苯基苯胺](10g,24.4mmol)、碘-4-溴苯(13.8g,48.8mmol)、CuI(2.3g,12.2mmol)、乙二胺(1.6mL,24.4mmol)、K3PO4(13g,61mmol)和甲苯(150mL)的混合物在圆底烧瓶中搅拌且回流过夜。反应混合物用EA/H2O萃取,用MgSO4干燥,且在减压下蒸馏。粗产物用柱色谱法使用MC:Hx纯化以获得化合物1-2(11g,80%)。
制备化合物C-37
化合物1-2[4-(9-(4-溴苯基)-9H-咔唑-3-基)-N,N-二苯基苯胺](6g,10.6mmol)、二苯并噻吩-4-硼酸(2.9g,12.7mmol)、Pd(PPh3)4(0.6g,0.53mmol)、K2CO3(3.6g,26.5mmol)、甲苯(45mL)、乙醇(15mL)和水(15mL)的混合物在圆底烧瓶中搅拌且回流持续4小时。反应混合物用EA/H2O萃取,用MgSO4干燥,且在减压下蒸馏。粗产物用柱色谱法使用MC:Hx纯化以获得化合物C-37(白色固体,5.2g,73%)。
MS/EIMS实验值668.8;计算值668.23
实例2:制备化合物C-83
制备化合物2-1
二苯并[b,d]噻吩-4-基硼酸(30g,0.13mol)、1-溴-4-碘苯(93g,0.33mol)、Pd(PPh3)4(7.6g,0.0065mol)、Na2CO3(28g,0.26mol)、甲苯(400mL)和H2O(130mL)的混合物在圆底烧瓶中在120℃下搅拌12小时。在完成反应之后,混合物用乙酸乙酯萃取。有机层用MgSO4干燥且过滤。在减压下去除溶剂之后,剩余产物用柱色谱法纯化以获得化合物2-1(白色固体,24g,54%)。
制备化合物C-83
化合物2-1(6.00g,17.7mmol)、9-苯基-9H,9′H-3,3′-联咔唑(7.59g,18.6mmol)、CuI(1.68g,8.84mmol)、K3PO4(11.3g,53.0mmol)和二甲苯(120mL)的混合物在圆底烧瓶中在160℃下搅拌12小时。在完成反应之后,混合物过滤,用甲醇洗涤且经由硅石过滤。在减压下去除溶剂之后,剩余产物用再结晶纯化以获得化合物C-83(白色固体,5.5g,47%)。
MS/EIMS实验值666.8;计算值666.21
实例3:制备化合物C-88
制备化合物3-1
二苯并[b,d]噻吩(70g,0.37mol)、溴(17.6mL,0.34mol)和氯仿(2000mL)的混合物在圆底烧瓶中在室温下搅拌48小时。在完成反应之后,混合物用二氯甲烷萃取。有机层用MgSO4干燥且过滤。在减压下去除溶剂之后,剩余产物用再结晶纯化以获得化合物3-1(白色固体,43g,43%)。
制备化合物3-2
n-BuLi(95mL,己烷中的2.25M溶液)在-78℃下在无水条件和氮气氛围下缓慢添加到圆底烧瓶中的无水四氢呋喃(THF)(1200mL)和化合物3-1(25g,0.095mol)的混合物中。所述混合物在-78℃下搅拌1小时,且随后三异丙醇硼[B(O-iPr)3](110mL,0.47mol)在-78℃下缓慢添加到所述混合物中。所述混合物升温到室温且静置反应12小时。在完成反应之后,混合物用乙酸乙酯萃取。有机层用MgSO4干燥且过滤。在减压下去除溶剂之后,剩余产物用再结晶纯化以获得化合物3-2(白色固体,20g,92%)。
制备化合物3-3
9-苯基-9H,9′H-3,3′-联咔唑(20g,0.49mol)、1-溴-4-碘苯(28g,0.98mol)、CuI(9.3g,0.49mol)、K3PO4(26g,0.12mol)、乙二胺(EDA)(3.3mL,0.05mmol)和甲苯(300mL)的混合物在圆底烧瓶中在120℃下搅拌12小时。在完成反应之后,混合物过滤,用甲醇洗涤,且进行柱色谱法。在减压下去除溶剂之后,剩余产物用再结晶纯化以获得化合物3-3(白色固体,17g,62%)。
制备化合物C-88
化合物3-3(6.2g,11.0mmol)、化合物3-2(3.3g,14.4mol)、Pd(PPh3)4(0.64g,0.55mol)、Na2CO3(2.33g,0.022mol)、甲苯(70mL)和H2O(10mL)的混合物在圆底烧瓶中在120℃下搅拌12小时。在完成反应之后,混合物过滤,用甲醇洗涤,且进行柱色谱法。在减压下去除溶剂之后,剩余产物用再结晶纯化以获得化合物C-88(白色固体,3g,41%)。
MS/EIMS实验值666.8;计算值666.21
装置实例1:通过使用本发明的有机电致发光化合物制造OLED装置
OLED装置使用本发明的材料制造。用于有机发光二极管(OLED)装置(三星康宁(Samsung Corning),大韩民国(Republic of Korea))的在玻璃衬底上的透明电极氧化铟锡(ITO)薄膜(15Ω/sq)依序用三氯乙烯、丙酮、乙醇和蒸馏水进行超声波洗涤,并且随后存储于异丙醇中。接着,ITO衬底安装在真空气相沉积设备的衬底夹持器上。将N1,N1′-([1,1′-联苯基]-4,4′-二基)双(N1-(萘-1-基)-N4,N4-二苯基苯-1,4-二胺)引入到真空气相沉积设备的单元中,且随后将所述设备的腔室中的压力控制在10-6托。此后,将电流施加到所述单元以蒸发以上引入的材料,由此在ITO衬底上形成厚度为60nm的空穴注入层。接着,将化合物C-37引入到真空气相沉积设备的另一单元中,且通过向所述单元施加电流使其蒸发,由此在空穴注入层上形成厚度为20nm的空穴传输层。此后,9-(4-([1,1′:3′,1″-三联苯]-4-基)嘧啶-2-基)-3-(二苯并[b,d]噻吩-4-基)-9H-咔唑作为主体材料引入到真空气相沉积设备的一个单元中,且化合物D-1作为掺杂剂引入到另一单元中。所述两种材料以不同比率蒸发,使得所述掺杂剂以基于主体和掺杂剂的总量15wt%的掺杂量沉积以在空穴传输层上形成厚度为30nm的发光层。随后,将2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑引入到一个单元中,并且将喹啉锂引入到另一单元中。所述两种材料以相同比率蒸发,使得其分别以50wt%的掺杂量沉积以在发光层上形成厚度为30nm的电子传输层。接着,在电子传输层上沉积厚度为2nm的喹啉锂作为电子注入层之后,通过另一真空气相沉积设备在电子注入层上沉积厚度为150nm的Al阴极。因此,制造OLED装置。用于制造OLED装置的所有材料在使用之前都通过在10-6托下真空升华而纯化。所制造的OLED装置显示亮度为4300cd/m2且电流密度为10.5mA/cm2的绿光发射。
装置实例2:通过使用本发明的有机电致发光化合物制造OLED装置
以与装置实例1相同的方式制造OLED装置,除了使用化合物C-83来形成厚度为20nm的空穴传输层,且在真空气相沉积设备的一个单元中作为主体材料的9-(4-([1,1′-联苯基]-4-基)喹唑啉-2-基)-9′-苯基-9H,9′H-3,3′-联咔唑以及在另一单元中作为掺杂剂的化合物D-78以不同比率蒸发,使得所述掺杂剂以基于主体和掺杂剂的总量为3wt%的掺杂量沉积以在空穴传输层上形成厚度为30nm的发光层。所制造的OLED装置显示亮度为1480cd/m2且电流密度为10.0mA/cm2的红光发射。
比较装置实例1:通过使用常规有机电致发光材料制造OLED装置
以与装置实例1相同的方式制造OLED装置,除了使用N,N′-二(4-联苯基)-N,N′-二(4-联苯基)-4,4′-二氨基联苯来形成厚度为20nm的空穴传输层;使用作为主体材料的4,4′-N,N′-二咔唑-联苯和作为掺杂剂的化合物D-15在空穴传输层上形成厚度为30nm的发光层;且使用铝(III)双(2-甲基-8-喹啉根)-4-苯基苯酚盐来形成厚度为10nm的空穴阻挡层。所制造的OLED装置显示亮度为4750cd/m2且电流密度为15.30mA/cm2的绿光发射。
比较装置实例2:通过使用常规有机电致发光材料制造OLED装置
以与装置实例1相同的方式制造OLED装置,除了使用N,N′-二(4-联苯基)-N,N′-二(4-联苯基)-4,4′-二氨基联苯来形成厚度为20nm的空穴传输层;使用作为主体材料的CBP和作为掺杂剂的D-50在空穴传输层上形成厚度为30nm的发光层;且使用铝(III)双(2-甲基-8-喹啉根)-4-苯基苯酚盐来形成厚度为10nm的空穴阻挡层。所制造的OLED装置显示亮度为3480cd/m2且电流密度为27.2mA/cm2的红光发射。
如上文所示,本发明的有机电致发光化合物具有比常规材料优良的特征,并且因此使用本发明的有机电致发光化合物的装置呈现优良发光特征和电流效率。
Claims (6)
1.一种由下式1表示的有机电致发光化合物,
其中
L1和L2各自独立地表示单键、被取代或未被取代的(C6-C30)亚芳基或被取代或未被取代的5到30元亚杂芳基;
Ar1和Ar2各自独立地表示被取代或未被取代的(C6-C30)芳基或被取代或未被取代的5到30元杂芳基;
Ar1和L2可与其上键结的氮原子键联在一起以形成含氮5或30元杂芳基;
X表示-S-或-C(R5)(R6)-;
R1到R6各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、被取代或未被取代的(C1-C30)烷基、被取代或未被取代的(C2-C30)烯基、被取代或未被取代的(C2-C30)炔基、被取代或未被取代的(C1-C30)烷氧基、被取代或未被取代的(C3-C30)环烷基、被取代或未被取代的(C3-C30)环烯基、被取代或未被取代的3到7元杂环烷基、被取代或未被取代的(C6-C30)芳基、被取代或未被取代的5到30元杂芳基、-NR11R12、-SiR13R14R15、-SR16、-OR17、-COR18或-B(OR19)(OR20);或可键联到相邻取代基以形成单环或多环、3到30元脂环或芳环,所述环的碳原子可用至少一个选自氮、氧和硫的杂原子置换;
R11到R20各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、被取代或未被取代的(C1-C30)烷基、被取代或未被取代的(C2-C30)烯基、被取代或未被取代的(C2-C30)炔基、被取代或未被取代的(C1-C30)烷氧基、被取代或未被取代的(C3-C30)环烷基、被取代或未被取代的(C3-C30)环烯基、被取代或未被取代的3到7元杂环烷基、被取代或未被取代的(C6-C30)芳基或被取代或未被取代的5到30元杂芳基;或可键联到相邻取代基以形成单环或多环、3到30元脂环或芳环,所述环的碳原子可用至少一个选自氮、氧和硫的杂原子置换;
a和c各自独立地表示1到4的整数,其中a或c是2或大于2的整数,各R1或各R3是相同或不同的;
b和d各自独立地表示1到3的整数,其中b或d是2或大于2的整数,各R2或各R4是相同或不同的;
所述(亚)杂芳基含有至少一个选自B、N、O、S、P(=O)、Si和P的杂原子;
所述杂环烷基含有至少一个选自O、S和N的杂原子;且
其条件是在X为-C(R5)(R6)-的情况下,通过Ar1和L2的键联所形成的杂芳基不是咔唑环。
2.根据权利要求1所述的有机电致发光化合物,其中L1和L2各自独立地表示单键、被取代或未被取代的(C6-C20)亚芳基或被取代或未被取代的5到21元亚杂芳基;
Ar1和Ar2各自独立地表示被取代或未被取代的(C6-C20)芳基或被取代或未被取代的5到21元杂芳基;
R1到R6各自独立地表示氢、卤素、被取代或未被取代的(C1-C15)烷基、被取代或未被取代的(C6-C30)芳基、被取代或未被取代的5到30元杂芳基、-NR11R12或-SiR13R14R15;
R11和R12各自独立地表示被取代或未被取代的(C6-C15)芳基;且
R13到R15各自独立地表示被取代或未被取代的(C1-C10)烷基。
3.根据权利要求1所述的有机电致发光化合物,其中L1和L2各自独立地表示单键、未被取代的(C6-C18)亚芳基、被(C1-C6)烷基取代的(C6-C18)亚芳基或未被取代的5到10元亚杂芳基;
Ar1和Ar2各自独立地表示未被取代的(C6-C18)芳基、被(C1-C6)烷基取代的(C6-C18)芳基、(C6-C20)芳基、(C1-C6)烷基(C6-C20)芳基、二(C6-C20)芳基氨基、(C6-C20)芳基(5到21元)杂芳基氨基或5到21元杂芳基、未被取代的5到15元杂芳基或被(C1-C6)烷基取代的5到15元杂芳基、(C6-C20)芳基、(C1-C6)烷基(C6-C20)芳基或二(C6-C20)芳基氨基;且
R1到R6各自独立地表示氢、卤素、未被取代的(C1-C6)烷基、被(C1-C6)烷基取代的硅烷基、未被取代或被(C1-C6)烷基取代的(C6-C20)芳基或未被取代的5到21元杂芳基。
4.根据权利要求1所述的有机电致发光化合物,其中在L1、L2、Ar1、Ar2、R1到R6和R11到R20中的所述被取代的烷基、所述被取代的烯基、所述被取代的炔基、所述被取代的烷氧基、所述被取代的环烷基、所述被取代的环烯基、所述被取代的杂环烷基、所述被取代的(亚)芳基和所述被取代的(亚)杂芳基的取代基各自独立地为选自由以下组成的群组的至少一者:氘、卤素、氰基、羧基、硝基、羟基、(C1-C30)烷基、卤基(C1-C30)烷基、(C2-C30)烯基、(C2-C30)炔基、(C1-C30)烷氧基、(C1-C30)烷硫基、(C3-C30)环烷基、(C3-C30)环烯基、3到7元杂环烷基、(C6-C30)芳氧基、(C6-C30)芳基硫基、未被取代或被(C6-C30)芳基取代的5到30元杂芳基、未被取代或被5到30元杂芳基取代的(C6-C30)芳基、三(C1-C30)烷基硅烷基、三(C6-C30)芳基硅烷基、二(C1-C30)烷基(C6-C30)芳基硅烷基、(C1-C30)烷基二(C6-C30)芳基硅烷基、氨基、单或二(C1-C30)烷基氨基、单或二(C6-C30)芳基氨基、(C1-C30)烷基(C6-C30)芳基氨基、(C1-C30)烷基羰基、(C1-C30)烷氧羰基、(C6-C30)芳基羰基、二(C6-C30)芳基硼羰基、二(C1-C30)烷基硼羰基、(C1-C30)烷基(C6-C30)芳基硼羰基、(C6-C30)芳基(C1-C30)烷基和(C1-C30)烷基(C6-C30)芳基。
5.根据权利要求1所述的有机电致发光化合物,其中所述由式1表示的化合物是选自由以下组成的群组:
6.一种有机电致发光装置,其包含根据权利要求1所述的化合物。
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PCT/KR2013/009246 WO2014061991A1 (en) | 2012-10-17 | 2013-10-16 | Novel organic electroluminescent compounds and organic electroluminescent device containing the same |
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KR101483933B1 (ko) | 2015-01-19 |
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