CN103857673A - 新有机电致发光化合物和使用该化合物的有机电致发光器件 - Google Patents
新有机电致发光化合物和使用该化合物的有机电致发光器件 Download PDFInfo
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- CN103857673A CN103857673A CN201280049556.9A CN201280049556A CN103857673A CN 103857673 A CN103857673 A CN 103857673A CN 201280049556 A CN201280049556 A CN 201280049556A CN 103857673 A CN103857673 A CN 103857673A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 78
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- 125000005104 aryl silyl group Chemical group 0.000 claims description 17
- -1 carbazyl Chemical group 0.000 claims description 17
- 238000005401 electroluminescence Methods 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000005605 benzo group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 3
- 239000000463 material Substances 0.000 abstract description 40
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 43
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- 239000002019 doping agent Substances 0.000 description 13
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 150000004646 arylidenes Chemical group 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 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
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
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- 229910052741 iridium Inorganic materials 0.000 description 3
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- 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
- 238000000034 method Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
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- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 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
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 2
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- 0 CC*(C)=Cc(cc1)cc(*2)c1-c1c2cc(C)cc1 Chemical compound CC*(C)=Cc(cc1)cc(*2)c1-c1c2cc(C)cc1 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 229910052782 aluminium Inorganic materials 0.000 description 2
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- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
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- 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
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
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- 238000004821 distillation Methods 0.000 description 2
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- 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
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- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
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- 238000000746 purification Methods 0.000 description 2
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- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
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- SSABEFIRGJISFH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)pyridine Chemical compound FC1=CC(F)=CC=C1C1=CC=CC=N1 SSABEFIRGJISFH-UHFFFAOYSA-N 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical class C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
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- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- FYJHZWMNFAGEER-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(cccc2)c2c2cc(-c(cc3c4c5cccc4)ccc3[n]5-c(cc3)ccc3-c3ccc-4c5c3cccc5-c3cc(-c5cc6ccccc6cc5)ccc-43)ccc12 Chemical compound c(cc1)ccc1-[n]1c(cccc2)c2c2cc(-c(cc3c4c5cccc4)ccc3[n]5-c(cc3)ccc3-c3ccc-4c5c3cccc5-c3cc(-c5cc6ccccc6cc5)ccc-43)ccc12 FYJHZWMNFAGEER-UHFFFAOYSA-N 0.000 description 1
- ZMWCHRRHBLRTOD-UHFFFAOYSA-N c(cc1-2)ccc1-c1ccc(-c(cc3)ccc3-c3cc(-[n](c4ccccc4c4c5)c4ccc5-[n]4c(cccc5)c5c5c4cccc5)ccc3)c3c1c-2ccc3 Chemical compound c(cc1-2)ccc1-c1ccc(-c(cc3)ccc3-c3cc(-[n](c4ccccc4c4c5)c4ccc5-[n]4c(cccc5)c5c5c4cccc5)ccc3)c3c1c-2ccc3 ZMWCHRRHBLRTOD-UHFFFAOYSA-N 0.000 description 1
- YRFKLLWMUCDIAX-UHFFFAOYSA-N c(cc1-2)ccc1-c1ccc(-c(cc3)ccc3-c3cccc(-[n]4c(ccc(-c5ccc6[o]c7ccccc7c6c5)c5)c5c5ccccc45)c3)c3c1c-2ccc3 Chemical compound c(cc1-2)ccc1-c1ccc(-c(cc3)ccc3-c3cccc(-[n]4c(ccc(-c5ccc6[o]c7ccccc7c6c5)c5)c5c5ccccc45)c3)c3c1c-2ccc3 YRFKLLWMUCDIAX-UHFFFAOYSA-N 0.000 description 1
- UQLHZYDASGHVOP-UHFFFAOYSA-N c(cc1-2)ccc1-c1ccc(-c3cccc(-c(c4c5cccc4)ccc5-[n](c(cccc4)c4c4c5)c4ccc5-c(cc4)cc5c4[s]c4ccccc54)c3)c3c1c-2ccc3 Chemical compound c(cc1-2)ccc1-c1ccc(-c3cccc(-c(c4c5cccc4)ccc5-[n](c(cccc4)c4c4c5)c4ccc5-c(cc4)cc5c4[s]c4ccccc54)c3)c3c1c-2ccc3 UQLHZYDASGHVOP-UHFFFAOYSA-N 0.000 description 1
- 150000004770 chalcogenides Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
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- 230000000052 comparative effect Effects 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
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- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000005563 perylenylene group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Abstract
本发明涉及新颖的化合物以及包含该化合物的有机电致发光器件。由于本发明的化合物在传输电子方面具有高效率,因此可防止在制造器件时化合物的结晶,且由于该化合物适用于层的形成,可改善该器件的现有特性,最终该化合物可以制造出一种有机电致发光器件,其与含有常规材料的器件相比,具有降低的驱动电压、改进的功率效率、和改进的发光效率和寿命特性。
Description
技术领域
本发明涉及新颖的有机电致发光化合物以及使用该化合物的有机电致发光器件。
背景技术
电致发光(EL)器件是一种自发光器件,其相对于其他类型的显示器件的优势在于提供了更宽的可视角、更高的对比度并具有更快速的响应时间。伊斯曼柯达公司(Eastman Kodak)通过使用小分子(芳族二胺)和铝配合物作为形成发光层的材料,首先开发了一种有机EL器件[Appl.Phys.Lett.51,913,1987]。
有机EL器件中决定发光效率的最重要的因素是发光材料。迄今为止,荧光材料被广泛地用作发光材料。然而,从电致发光的机理来看,研制磷光材料是理论上将发光效率提高4倍的最好的方法之一。铱(III)络合物是众所周知的磷光材料,包括二(2-(2′-苯并噻吩基)-吡啶根合-N,C3′)(乙酰丙酮酸根合)铱((acac)Ir(btp)2)、三(2-苯基吡啶)铱(Ir(ppy)3)和二(4,6-二氟苯基吡啶根合-N,C2)吡啶甲酸根合(picolinate)铱(Firpic),分别作为红色、绿色和蓝色材料。特别是近来在日本、欧洲和美国,人们正在对大量磷光材料进行研究。
迄今为止,已知4,4′-N,N′-二咔唑-联苯(CBP)是最广泛用作磷光物质的基质材料。此外,已知有机EL器件使用浴铜灵(BCP)和二(2-甲基-8-羟基喹啉合(quinolinate))(4-苯基苯酚)铝(III)(BAlq)用于空穴阻挡层;日本先锋公司(Pioneer)等开发了一种高性能有机EL器件,其采用了BAlq的衍生物作为基质材料。
虽然这些材料提供了良好的发光特性,但它们具有以下一些不足。由于它们较低的玻璃化转变温度和较差的热稳定性,当它们在真空中处于高温沉积过程时可发生降解。因为有机EL器件的功率效率是由[(π/电压)×电流效率]确定的,功率效率与电压成反比,因此必须提高功率效率从而降低功耗。虽然含有磷光材料的有机EL器件提供了比含有荧光材料的有机EL器件更高的电流效率(cd/A),但与采用荧光材料的有机EL器件相比,采用常规磷光材料(如BAlq或CBP)的有机EL器件具有更高的驱动电压。因此,采用常规磷光材料的EL器件在功率效率(lm/w)上没有优势。此外,该有机EL器件的工作寿命短。因此,需研究具有更好性能的红色基质材料。
日本专利申请特开第1999-149987号公开了一种器件,其含有N-咔唑基与荧蒽结构键合的化合物、且用卢比烯(lublene)作为发光层材料,该发光层同样作为空穴注入和传输层。不过,该器件发射黄光。所述专利申请中同样公开了发射绿光的荧光电致发光器件,其含有作为空穴注入和传输层基质材料的N-咔唑基与荧蒽结构键合的化合物。
不过,所述专利中并没有公开发射红光的磷光电致发光器件,其含有作为发光层基质材料的N-咔唑基与荧蒽结构键合的化合物。
发明内容
技术问题
本发明的目的是提供一种有机电致发光化合物,该化合物使得器件具有高发光效率和长工作寿命,且该化合物发射红光;本发明还提供了一种采用所述化合物作为发光材料的有机电致发光器件,其具有高效率和长寿命。
解决问题的方法
本发明的发明人发现可以通过如下通式1表示的有机电致发光化合物来实现上述目的:
其中
L1表示单键、取代或未取代的3元至30元杂亚芳基、或取代或未取代的(C6-C30)亚芳基;
X表示-O-、-S-、-CR11R12-或–NR13-;
R11至R13各自独立地表示取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或者取代或未取代的3元至30元杂芳基;
R1至R6各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基、取代或未取代的(C3-C30)环烷基、取代或未取代的5元至7元杂环烷基、取代或未取代的(C6-C30)芳基(C1-C30)烷基、与至少一个(C3-C30)环烷基稠和的取代或未取代的(C6-C30)芳基、与至少一个取代或未取代的芳环稠和的5元至7元杂环烷基、与至少一个取代或未取代的芳环稠和的(C3-C30)环烷基、-NR14R15、-SiR16R17R18、-SR19、-OR20、(C2-C30)烯基、(C2-C30)炔基、氰基或硝基;
R14至R20各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基;或者它们与相邻取代基相连以形成单环或多环的(C5-C30)脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子替代;
a、d和e各自独立地表示1-4的整数,其中当a、d或e是大于或等于2的整数时,每一个R1、每一个R4和每一个R5是相同或不同的;
b和f各自独立地表示1-3的整数,其中当b或f是大于或等于2的整数时,每一个R2和每一个R6是相同或不同的;
c表示1-5的整数;其中当c是等于或大于2的整数时,每一个R3是相同或不同的;
m表示1、2或3;以及
所述杂环烷基和杂(亚)芳基含有至少一个选自B、N、O、S、P(=O)、Si和P的杂原子。
发明的有益效果
由于本发明的有机电致发光化合物具有高传输电子效率,因而在制备器件时可以防止结晶。此外,所述化合物具有良好的成层性,可改善器件的电流特性。因此,它们可制备出具有较低的驱动电压和提高的功率效率的有机电致发光器件。
本发明的实施方式
下面将详细描述本发明。但是,以下描述是用于解释本发明,而不是为了以任意方式限制本发明的范围。
本发明涉及用上述通式1表示的有机电致发光化合物,包括所述化合物的有机电致发光材料,以及包括所述材料的有机电致发光器件。
本文中,“烷基”包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基等;“烯基”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;“炔基”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;“环烷基”包括环丙基、环丁基、环戊基、环己基等;“5元至7元杂环烷基”是具有至少一个杂原子和5-7个环骨架原子的环烷基,所述杂原子选自B、N、O、S、P(=O)、Si和P,优选选自O、S和N,并且包括四氢呋喃、吡咯烷、四氢噻吩(thiolan)、四氢吡喃等;“(亚)芳基”是衍生自芳烃的单环或稠环,其包括苯基、联苯基、三联苯基、萘基、芴基、菲基、蒽基、茚基、苯并[9,10]菲基、芘基、并四苯基(tetracenyl)、苝基(perylenyl)、基(chrysenyl)、萘并萘基(naphthacenyl)、荧蒽基(fluoranthenyl)等;“3元至30元杂(亚)芳基”是具有至少一个杂原子(优选为1-4个杂原子)和2-30个环骨架原子的芳基,所述杂原子选自B、N、O、S、P(=O)、Si和P;其是单环,或与至少一个苯环稠和的稠环;其可部分饱和;其可通过单键将至少一个杂芳基或芳基与杂芳基相连而形成;并且包括单环的环形杂芳基和稠和的环形杂芳基,所述单环的环形杂芳基包括呋喃基、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、***基、四唑基、呋咱基(furazanyl)、吡啶基、吡嗪基、嘧啶基、哒嗪基等;所述稠和的环形杂芳基包括苯并呋喃基、苯并噻吩基(benzothiophenyl)、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基(dibenzothiophenyl)、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(cinnolinyl)、喹唑啉基、喹喔啉基(quinoxalinyl)、咔唑基、吩噁嗪基、菲啶基(phenanthridinyl)、苯并间二氧杂环戊烯基(benzodioxolyl)等。此外,“卤素”包括F、Cl、Br和I。
本文中,(C1-C30)烷基优选为(C1-C20)烷基,更优选为(C1-C6)烷基;(C6-C30)芳基优选为(C6-C21)芳基;3元至30元杂芳基优选为3元至21元杂芳基;(C3-C30)环烷基优选为(C3-C20)环烷基,更优选为(C3-C7)环烷基。
本文所用术语“取代或未取代的”中的“取代”指的是某个官能团中的氢原子被另一个原子或基团(即取代基)取代。
通式1的L1、R1至R6以及R11至R20基团中所述取代的烷基、取代的烯基、取代的炔基、取代的(亚)芳基、取代的杂(亚)芳基、取代的环(亚)烷基、取代的杂环烷基、和取代的芳烷基的取代基各自独立地是至少一种选自下组的基团:氘、卤素、未取代的或被卤素取代的(C1-C30)烷基、(C6-C30)芳基、未取代的或被(C6-C30)芳基取代的3元至30元杂芳基、5元至7元杂环烷基、(C3-C30)环烷基、三(C1-C30)烷基甲硅烷基、三(C6-C30)芳基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基、(C1-C30)烷基二(C6-C30)芳基甲硅烷基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、苯并咔唑基、二苯并咔唑基、二(C1-C30)烷基氨基、二(C6-C30)芳基氨基、(C1-C30)烷基(C6-C30)芳基氨基、二(C6-C30)芳基硼基、二(C1-C30)烷基硼基、(C1-C30)烷基(C6-C30)芳基硼基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基和羟基;优选是至少一种选自下组的基团:氘、卤素、取代或未取代的(C1-C6)烷基、取代或未取代的(C6-C21)芳基、取代或未取代的3元至21元杂芳基、三(C6-C12)芳基甲硅烷基;更优选是至少一种选自下组的基团:氘、卤素、未取代的(C1-C6)烷基、未取代的(C6-C21)芳基、未取代的3元至21元杂芳基和三(C6-C12)芳基甲硅烷基。
根据本文的一个实施方式,在通式1中,L1表示单键、3-至30-元杂亚芳基或(C6-C30)亚芳基;X表示-O-、-S-、-CR11R12-或–NR13-;R11-R13各自独立地表示(C1-C30)烷基、(C6-C30)芳基、或3元至30元杂芳基;R1-R6各自独立地表示氢、氘、卤素、(C1-C30)烷基、(C6-C30)芳基、3元至30元杂芳基、或咔唑基;m表示1或2;L1中的杂亚芳基和亚芳基,R1-R6和R11-R13中的烷基、芳基、杂芳基和咔唑基可用至少一种选自下组的基团取代:氘、卤素、未取代或被卤素取代的(C1-C30)烷基、(C6-C30)芳基、3元至30元杂芳基、三(C1-C30)烷基甲硅烷基、三(C6-C30)芳基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基、(C1-C30)烷基二(C6-C30)芳基甲硅烷基、咔唑基、苯并咔唑基、和二苯并咔唑基。
优选地,L1表示单键、亚苯基、亚萘基、亚联苯基、亚三联苯基、亚蒽基、亚茚基、亚芴基、亚菲基、亚苯并[9,10]菲基、亚芘基(pyrenylene)、亚苝基(perylenylene)、亚基(chrysenylene)、亚并四苯基(naphthacenylene)、亚荧蒽基(fluoranthenylene)、亚苯基-亚萘基(phenylene-naphthylene)、亚呋喃基、亚噻吩基、亚吡咯基、亚咪唑基、亚吡唑基、亚噻唑基、亚噻二唑基、亚异噻唑基、亚异噁唑基、亚噁唑基、亚噁二唑基、亚三嗪基、亚四嗪基、亚***基、亚呋咱基(furazanylene)、亚吡啶基、亚吡嗪基、亚嘧啶基、亚哒嗪基、亚苯并呋喃基、亚苯并噻吩基(benzothiophenylene)、亚异苯并呋喃基、亚苯并咪唑基、亚苯并噻唑基、亚苯并异噻唑基、亚苯并异噁唑基、亚苯并噁唑基、亚异吲哚基、亚吲哚基、亚吲唑基、亚苯并噻二唑基、亚喹啉基、亚异喹啉基、亚噌啉基(cinnolinylene)、亚喹唑啉基、亚喹喔啉基(quinoxalinylene)、亚咔唑基、亚菲啶基(phenanthridinylene)、亚苯并间二氧杂环戊烯基(benzodioxolylene)、亚二苯并呋喃基或亚二苯并噻吩基(dibenzothiophenylene)。
在上述通式1中,L1优选为单键、或取代或未取代的(C6-C21)亚芳基,更优选为单键、或未取代的或被(C1-C6)烷基取代的(C6-C21)亚芳基。
R1-R6各自独立地表示氢、卤素、取代或未取代的(C6-C21)芳基、取代或未取代的3元至21元杂芳基,更优选为氢;卤素;未取代或被氘、(C1-C6)烷基、(C6-C21)芳基、3元至21元杂芳基或三(C6-C12)芳基甲硅烷基取代的(C6-C21)芳基;或未取代的3元至21元杂芳基。
优选地,R11-R13各自独立地的是取代或未取代的(C1-C6)烷基、取代或未取代的(C6-C21)芳基;或取代或未取代的3元至21元杂芳基,更优选的是未取代的(C1-C6)烷基;未取代的或被卤素、氘或(C1-C6)烷基取代的(C6-C21)芳基;或被(C6-C21)芳基取代的3元至21元杂芳基。
本发明的代表性化合物包括以下化合物:
本发明的有机电致发光化合物可通过以下反应方案来制备。
[反应方案1]
其中,L1、Z、R1至R4、m、a、b、c和d如上通式1所定义,Hal表示卤素。
此外,本发明提供包括通式1的有机电致发光化合物的有机电致发光材料,以及包括所述材料的有机电致发光器件。上述材料可只包括本发明的有机电致发光化合物,或者还可包括通常用于有机电致发光材料的常规材料。所述有机电致发光器件包括第一电极、第二电极以及所述第一电极和第二电极之间的至少一层有机层。所述有机层包含至少一种本发明通式1的化合物。此外,所述有机层包括发光层,在该层中包含通式1的有机电致发光化合物作为基质材料。
当通式1的有机电致发光化合物用作发光层的基质材料时,可同时使用一种或多种磷光掺杂剂。用于本发明的电致发光器件的磷光掺杂剂并没有具体限制,但可优选自如下化学式2所表示的化合物:
M1L101L102L103---------------------(2)
其中M1选自Ir、Pt、Pd和Os;L101、L102和L103各自独立地选自如下结构:
R201,至R203各自独立地表示氢、氘、未取代的或被卤素取代的(C1-C30)烷基、未取代的或被(C1-C30)烷基取代的(C6-C30)芳基、或者卤素;
R204至R219各自独立地表示氢、氘、取代或未取代的(Cl-C30)烷基、取代或未取代的(C1-C30)烷氧基、取代或未取代的(C3-C30)环烷基、取代或未取代的(C2-C30)烯基、取代或未取代的(C6-C30)芳基、取代或未取代的单-或二-(C1-C30)烷基氨基、取代或未取代的单-或二-(C6-C30)芳基氨基、SF5、取代或未取代的三(C1-C30)烷基甲硅烷基、取代或未取代的二(C1-C30)烷基(C6-C30)芳基甲硅烷基、取代或未取代的三(C6-C30)芳基甲硅烷基、氰基或者卤素;
R220至R223各自独立地表示氢、氘、未取代的或被卤素取代的(C1-C30)烷基、或者未取代的或被(C1-C30)烷基取代的(C6-C30)芳基;
R224和R225各自独立地表示氢、氘、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或卤素,或者R224和R225可以与相邻取代基相连形成单环或多环的(C5-C30)脂环或芳环;
R226表示取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基或者卤素;
R227至R229各自独立地表示氢、氘、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基或者卤素;
Q表示或R231至R242各自独立地表示氢、氘、未取代的或被卤素取代的(C1-C30)烷基、(C1-C30)烷氧基、卤素、取代或未取代的(C6-C30)芳基、氰基或者取代或未取代的(C5-C30)环烷基,或者R231至R242中的每一个可通过亚烷基或亚烯基与相邻取代基相连以形成螺环或稠环,或者可通过亚烷基或亚烯基与R207或R208相连以形成饱和或不饱和的稠环。
通式2的掺杂剂包括以下这些,但不限于此:
除了通式1表示的有机电致发光化合物之外,本发明的有机电致发光器件还可包括至少一种选自基于芳胺的化合物和基于苯乙烯基芳胺的化合物的化合物。
在本发明的有机电致发光器件中,所述有机层还可包含至少一种选自元素周期表第1族金属、第2族金属、第四周期过渡金属、第五周期过渡金属、镧系金属和d-过渡元素的有机金属的金属,或者至少一种包含所述金属的络合物。所述有机层可包括发光层和电荷产生层。
此外,除了本发明的有机电致发光化合物之外,所述有机电致发光器件可通过进一步包含至少一层发光层来发射白光,所述发光层包含蓝光电致发光化合物、红光电致发光化合物或者绿光电致发光化合物。
优选地,在本发明的有机电致发光器件中,可以在一个或两个电极的内表面上放置至少一层选自硫属化物层、金属卤化物层和金属氧化物层的层(以下称为“表面层”)。具体地,优选将硅或铝的硫属化物(包括氧化物)层放置在电致发光介质层的阳极表面上,将金属卤化物层或金属氧化物层放置在电致发光介质层的阴极表面上。所述表面层为有机电致发光器件提供了工作稳定性。优选地,所述硫属化物包括SiOX(1≤X≤2)、AlOX(1≤X≤1.5)、SiON、SiAlON等;所述金属卤化物包括LiF、MgF2、CaF2、稀土金属氟化物等;所述金属氧化物包括Cs2O、Li2O、MgO、SrO、BaO、CaO等。
优选地,在本发明的有机电致发光器件中,电子传输化合物和还原性掺杂剂的混合区或者空穴传输化合物和氧化性掺杂剂的混合区可放置在电极对中的至少一个表面上。在这种情况下,电子传输化合物被还原成阴离子,这样电子从混合区注入并传输到电致发光介质中变得更加容易。此外,空穴传输化合物被氧化成阳离子,从而空穴从混合区注入并传输到电致发光介质中变得更加容易。优选地,所述氧化性掺杂剂包括各种路易斯酸和受体化合物,所述还原性掺杂剂包括碱金属、碱金属化合物、碱土金属、稀土金属及其混合物。可以采用还原性掺杂剂层作为电荷产生层来制备具有两层或更多层电致发光层并发射白光的电致发光器件。
下文参照以下实施例详细描述所述有机电致发光化合物、所述化合物的制备方法、以及包含本发明化合物的器件的发光性质:
实施例1:化合物C-35的制备
化合物1-2的制备
化合物1-1(50g,247.2mmol)溶解在MeCN(50mL)中并加入N-溴代琥珀酰亚胺(NBS)(44g,247.2mmol)后,将反应混合物在室温下搅拌1天。反应终止后,用乙酸乙酯(EA)萃取反应混合物,对有机层进行浓缩并通过二氧化硅柱进行纯化,得到化合物1-2(55.6g,80%)。
化合物1-3的制备
化合物1-2(7.7g,27.5mmol)溶于四氢呋喃(THF)(250mL)后,将反应混合物冷却至-78℃。将在己烷中的2.5M n-BuLi(17.6mL,44mmol)加入到该反应混合物中,并将该反应混合物搅拌1小时。在相同的温度下,缓慢加入B(Oi-Pr)3(12.6mL,55mmol),然后将该混合物搅拌2小时。搅拌后,通过添加2M HCl来淬灭该反应混合物,用蒸馏水和EA萃取,并浓缩有机层。用二氯甲烷(MC)和己烷对所述有机层进行重结晶,得到化合物1-3(4.0克,60%)。
化合物1-4的制备
将化合物1-3(4.5g,18.3mol)、4-溴碘代苯(6.73g,23.8mol)、Pd(PPh3)4(634mg,0.55mmol)和Na2CO3(5.8g,54.9mol)加入甲苯(110mL)和纯化水(27mL)中,将反应混合物在75℃下搅拌3小时。反应终止后,去除水层,将有机层浓缩并通过二氧化硅柱纯化,得到化合物1-4(3.9g,60%)。
化合物1-7的制备
将化合物1-5(14g,48.76mmol)、化合物1-6(10g,40.63mmol)、K2CO3(13.5g,97.52mmol)和Pd(PPh3)4(2.35g,2.03mmol)加入甲苯(200mL)、乙醇(50mL)和纯化水(50mL)中,将反应混合物在95℃下搅拌3小时。反应终止后,将反应混合物冷却至室温。去除水层,对有机层进行浓缩,并用MC研磨,然后进行过滤,得到化合物1-7(12克,72%)。
化合物C-35的制备
将化合物1-4(3.3g,9.2mmol)、化合物1-7(3.4g,8.4mmol)、Cs2CO3(8.2g,25.2mmol)、CuI(880mg,4.62mmol)和乙二胺(EDA)(0.6mL,8.4mmol)加入甲苯(50mL),将该反应混合物回流搅拌1天。用EA萃取反应混合物,并对该反应混合物进行减压蒸馏,然后通过柱(MC和己烷)进行过滤,得到化合物C-35(1.7g,29.8%)。
MS/FAB的实测值684.82;计算值684.26
实施例2:化合物C-56的制备
化合物2-1的制备
将化合物1-3(10g,40.6mol)、4,4′-二溴联苯(38g,121.9mol)、Pd(PPh3)4(2.3g,2.03mmol)和Na2CO3(12.9g,121.9mol)加入甲苯(244mL)和纯化水(60mL)中,将反应混合物在75℃下搅拌3小时。反应终止后,去除水层,将有机层浓缩并通过二氧化硅柱纯化,得到化合物2-1(9.5g,54%)。
化合物C-42的制备
将化合物2-1(5.0g,11.5mmol)、化合物1-7(4.7g,11.5mmol)、Pd(OAc)2(129mg,0.575mmol)、50%P(t-Bu)3(0.54mL,2.3mmol)和Cs2CO3(11.2g,34.5mmol)加入甲苯(50mL)中,将该反应混合物回流搅拌1天。用EA萃取反应混合物,并对该反应混合物进行减压蒸馏,然后通过柱(MC和己烷)进行过滤,得到化合物C-42(3.5g,40%)。
MS/FAB的实测值760.92;计算值760.29
器件实施例1:使用本发明化合物的OLED器件的制造
使用本发明的化合物来制造OLED器件。用三氯乙烯、丙酮、乙醇和蒸馏水依次对用于有机发光二极管(OLED)器件的玻璃基材上的透明电极氧化铟锡(ITO)薄膜(15Ω/sq)(韩国三星康宁公司(Samsung Corning,Republic ofKorea))进行超声清洗,然后储存在异丙醇中。接着,将ITO基材安装在真空气相沉积设备的基材夹具(holder)上。将N1,N1’-([1,1’-联苯基]-4,4’-二基)二(N1-(萘-1-基)-N4,N4-二苯基苯-1,4-二胺)引入所述真空气相沉积设备的室中,然后对所述设备的室压进行控制以达到10-6托。接着,向所述室施加电流以蒸发上述引入的物质,从而在ITO基材上形成厚度为60nm的空穴注入层。然后,将N,N’-二(4-联苯基)-N,N’-二(4-联苯基)-4,4’-二氨基联苯引入所述真空气相沉积设备的另一个室中,通过向该室施加电流以进行蒸发,从而在所述空穴注入层上形成厚度为20nm的空穴传输层。之后,将化合物C-42引入真空气相沉积设备的一个室中作为基质材料,并将化合物D-7引入另一个室中作为掺杂剂。将两种材料以不同的速率进行蒸发,并以4重量%掺杂剂(以基质材料和掺杂剂的总重量为基准计)的掺杂量进行沉积,从而在空穴传输层上形成厚度为30nm的发光层。然后,将2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑引入一个室中,并将8-羟基喹啉合锂(lithium quinolate)引入另一个室中。将两种物质分别以相同的速率进行蒸发,并以50重量%的掺杂量进行沉积,以在发光层上形成厚度为30nm的电子传输层。然后,在电子传输层上沉积了厚度为2nm的8-羟基喹啉合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。从而,制备了OLED器件。制备OLED器件所用的所有材料,在使用前通过在10-6托条件下的真空升华进行纯化。
制备的OLED器件在3.9V的驱动电压下发射出亮度为1,060cd/m2的红光且电流密度为7.7mA/cm2。此外,在5,000尼特的亮度下降至该亮度的90%的时间至少为130小时。
器件实施例2:使用本发明化合物的OLED器件的制造
使用与器件实施例1相同的方法制备OLED器件,不同之处在于使用化合物C-35作为基质材料,使用化合物D-7作为掺杂剂。
制备的OLED器件在3.8V的驱动电压下发射出亮度为1,020cd/m2的红光且电流密度为7.5mA/cm2。此外,在5,000尼特的亮度下降至该亮度的90%的时间至少为130小时。
比较例1:使用常规电致发光化合物制造OLED器件
使用与器件实施例1相同的方法制备OLED器件,不同之处在于使用4,4′-N,N′-二咔唑-联苯作为基质材料,使用化合物D-11作为掺杂剂,以沉积发光层,并且通过使用二(2-甲基-8-羟基喹啉合(quinolinato))4-苯基苯酚铝(III),将厚度为10nm的空穴阻挡层沉积在发光层和电子传输层之间。
制备的OLED器件在8.2V的驱动电压下发射出亮度为1,000cd/m2的红光且电流密度为20.4mA/cm2。此外,在5,000尼特的亮度下降至该亮度的90%的时间至少为10小时。
本发明的有机电致发光化合物比常规材料具有更为优异的发光特性。此外,采用本发明化合物作为发光基质材料的器件通过降低驱动电压提高了功率效率,且具有优异的发光效率和寿命的特性。
Claims (6)
1.一种由以下通式1表示的有机电致发光化合物:
其中
L1表示单键、取代或未取代的3元至30元杂亚芳基、或取代或未取代的(C6-C30)亚芳基;
X表示-O-、-S-、-CR11R12-或–NR13-;
R11至R13各自独立地表示取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或者取代或未取代的3元至30元杂芳基;
R1至R6各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基、取代或未取代的(C3-C30)环烷基、取代或未取代的5元至7元杂环烷基、取代或未取代的(C6-C30)芳基(C1-C30)烷基、与至少一个(C3-C30)环烷基稠和的取代或未取代的(C6-C30)芳基、与至少一个取代或未取代的芳环稠和的5元至7元杂环烷基、与至少一个取代或未取代的芳环稠和的(C3-C30)环烷基、-NR14R15、-SiR16R17R18、-SR19、-OR20、(C2-C30)烯基、(C2-C30)炔基、氰基、或硝基;
R14至R20各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基;或者它们与相邻取代基相连以形成单环或多环的(C5-C30)脂环或芳环,其碳原子可以被至少一个选自氮、氧和硫的杂原子替代;
a、d和e各自独立地表示1-4的整数,其中当a、d或e是大于或等于2的整数时,每一个R1、每一个R4和每一个R5是相同或不同的;
b和f各自独立地表示1-3的整数,其中当b或f是大于或等于2的整数时,每一个R2和每一个R6是相同或不同的;
c表示1-5的整数;其中当c是等于或大于2的整数时,每一个R3是相同或不同的;
m表示1、2或3;以及
所述杂环烷基和杂(亚)芳基含有至少一个选自B、N、O、S、P(=O)、Si和P的杂原子。
2.如权利要求1所述的化合物,其特征在于,所述L1、R1至R6以及R11至R20基团中所述取代的烷基、取代的烯基、取代的炔基、取代的(亚)芳基、取代的(亚)杂芳基、取代的环(亚)烷基、取代的杂环烷基和取代的芳烷基的取代基各自独立地是至少一种选自下组的基团:氘、卤素、未取代的或被卤素取代的(C1-C30)烷基、(C6-C30)芳基、未取代的或被(C6-C30)芳基取代的3元至30元杂芳基、5元至7元杂环烷基、(C3-C30)环烷基、三(C1-C30)烷基甲硅烷基、三(C6-C30)芳基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基、(C1-C30)烷基二(C6-C30)芳基甲硅烷基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、苯并咔唑基、二苯并咔唑基、二(C1-C30)烷基氨基、二(C6-C30)芳基氨基、(C1-C30)烷基(C6-C30)芳基氨基、二(C6-C30)芳基硼基、二(C1-C30)烷基硼基、(C1-C30)烷基(C6-C30)芳基硼基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基和羟基。
3.如权利要求1所述的化合物,其特征在于,
L1表示单键、3元至30元杂亚芳基或(C6-C30)亚芳基;
X表示-O-、-S-、-CR11R12-或–NR13-;
R11至R13各自独立地表示(C1-C30)烷基、(C6-C30)芳基、或3元至30元杂芳基;
R1至R6各自独立地表示氢、氘、卤素、(C1-C30)烷基、(C6-C30)芳基、3元至30元杂芳基、或咔唑基;
m表示1或2;以及
L1中的杂亚芳基和亚芳基、R1至R6和R11至R13中的烷基、芳基、杂芳基和咔唑基可被至少一种选自下组的基团取代:氘、卤素、未取代或被卤素取代的(C1-C30)烷基、(C6-C30)芳基、3元至30元杂芳基、三(C1-C30)烷基甲硅烷基、三(C6-C30)芳基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基、(C1-C30)烷基二(C6-C30)芳基甲硅烷基、咔唑基、苯并咔唑基、和二苯并咔唑基。
4.如权利要求3所述的化合物,其特征在于,
L1表示单键、亚苯基、亚萘基、亚联苯基、亚三联苯基、亚蒽基、亚茚基、亚芴基、亚菲基、亚苯并[9,10]菲基、亚芘基、亚苝基、亚基、亚并四苯基、亚荧蒽基、亚苯基-亚萘基、亚呋喃基、亚噻吩基、亚吡咯基、亚咪唑基、亚吡唑基、亚噻唑基、亚噻二唑基、亚异噻唑基、亚异噁唑基、亚噁唑基、亚噁二唑基、亚三嗪基、亚四嗪基、亚***基、亚呋咱基、亚吡啶基、亚吡嗪基、亚嘧啶基、亚哒嗪基、亚苯并呋喃基、亚苯并噻吩基、亚异苯并呋喃基、亚苯并咪唑基、亚苯并噻唑基、亚苯并异噻唑基、亚苯并异噁唑基、亚苯并噁唑基、亚异吲哚基、亚吲哚基、亚吲唑基、亚苯并噻二唑基、亚喹啉基、亚异喹啉基、亚噌啉基、亚喹唑啉基、亚喹喔啉基、亚咔唑基、亚菲啶基、亚苯并间二氧杂环戊烯基、亚二苯并呋喃基或亚二苯并噻吩基。
6.一种包含如权利要求1所述的化合物的有机电致发光器件。
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JP2014531419A (ja) | 2014-11-27 |
WO2013032278A1 (en) | 2013-03-07 |
TW201326359A (zh) | 2013-07-01 |
KR20130025087A (ko) | 2013-03-11 |
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