CN108409774A - 有机电致发光化合物及其应用和有机电致发光器件 - Google Patents
有机电致发光化合物及其应用和有机电致发光器件 Download PDFInfo
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- CN108409774A CN108409774A CN201711375428.4A CN201711375428A CN108409774A CN 108409774 A CN108409774 A CN 108409774A CN 201711375428 A CN201711375428 A CN 201711375428A CN 108409774 A CN108409774 A CN 108409774A
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- electroluminescence device
- compound
- phenyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 69
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 31
- 239000000463 material Substances 0.000 claims abstract description 40
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 238000006467 substitution reaction Methods 0.000 claims description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
- -1 xenyl Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 230000004888 barrier function Effects 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 230000000903 blocking effect Effects 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 230000005540 biological transmission Effects 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 239000009289 huang-lien-chieh-tu-tang Substances 0.000 claims description 2
- 230000037429 base substitution Effects 0.000 claims 1
- 230000003760 hair shine Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 25
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000010189 synthetic method Methods 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- 150000001454 anthracenes Chemical class 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- XKQMUXKUBYRKRX-UHFFFAOYSA-N 3-anilino-2-[2-[(1-benzylpyrazol-4-yl)amino]pyridin-4-yl]-6,6-dimethyl-5,7-dihydro-1H-indol-4-one Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C)C XKQMUXKUBYRKRX-UHFFFAOYSA-N 0.000 description 4
- MTBRQOGPXZHFAH-UHFFFAOYSA-N 3-anilino-2-pyridin-4-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one Chemical compound C1(=CC=CC=C1)NC1=C(NC2=C1C(NCC2)=O)C1=CC=NC=C1 MTBRQOGPXZHFAH-UHFFFAOYSA-N 0.000 description 4
- 0 CC(C)(*1)C(C)(C)O*1*1OC(C)(C)C(C)(C)O1 Chemical compound CC(C)(*1)C(C)(C)O*1*1OC(C)(C)C(C)(C)O1 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 150000002220 fluorenes Chemical class 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 150000002475 indoles Chemical class 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 150000004032 porphyrins Chemical class 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 description 3
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 3
- CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 150000002240 furans Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000003220 pyrenes Chemical class 0.000 description 3
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- PEDAETJPRCNYMH-UHFFFAOYSA-N 3-anilino-6,6-dimethyl-2-[2-[(1-methylpyrazol-4-yl)amino]pyridin-4-yl]-5,7-dihydro-1H-indol-4-one Chemical compound CC1(CC(C=2C(=C(NC=2C1)C1=CC(=NC=C1)NC=1C=NN(C=1)C)NC1=CC=CC=C1)=O)C PEDAETJPRCNYMH-UHFFFAOYSA-N 0.000 description 2
- QJTQKPNNQVLHHO-UHFFFAOYSA-N 9h-carbazole;1h-indole Chemical compound C1=CC=C2NC=CC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 QJTQKPNNQVLHHO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- ZISGLVMVAWKGRE-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3NC12.N1=NN=CC=C1 Chemical class C1=CC=CC=2C3=CC=CC=C3NC12.N1=NN=CC=C1 ZISGLVMVAWKGRE-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
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- 125000000468 ketone group Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical class [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 238000005092 sublimation method Methods 0.000 description 2
- GJVRUUHMZUPZBQ-UHFFFAOYSA-N tert-butyl 3-anilino-4-oxo-2-pyridin-4-yl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridine-5-carboxylate Chemical compound O=C1N(CCC2=C1C(=C(N2)C1=CC=NC=C1)NC1=CC=CC=C1)C(=O)OC(C)(C)C GJVRUUHMZUPZBQ-UHFFFAOYSA-N 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
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- 238000007740 vapor deposition Methods 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
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- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
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- KTSVVTQTKRGWGU-UHFFFAOYSA-N 1-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]butane Chemical class CCCCOCCOCCOCCOCCCC KTSVVTQTKRGWGU-UHFFFAOYSA-N 0.000 description 1
- SNAQINZKMQFYFV-UHFFFAOYSA-N 1-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOC SNAQINZKMQFYFV-UHFFFAOYSA-N 0.000 description 1
- JCHJBEZBHANKGA-UHFFFAOYSA-N 1-methoxy-3,5-dimethylbenzene Chemical class COC1=CC(C)=CC(C)=C1 JCHJBEZBHANKGA-UHFFFAOYSA-N 0.000 description 1
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical class CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 1
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical class C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 1
- ZNOVTXRBGFNYRX-UHFFFAOYSA-N 2-[[4-[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 ZNOVTXRBGFNYRX-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical class C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 1
- LVUBSVWMOWKPDJ-UHFFFAOYSA-N 4-methoxy-1,2-dimethylbenzene Chemical class COC1=CC=C(C)C(C)=C1 LVUBSVWMOWKPDJ-UHFFFAOYSA-N 0.000 description 1
- VKIWBMLWZKNBSO-UHFFFAOYSA-N Brc(cc1)ccc1[Si+](c1ccccc1)(c1ccccc1)c1ccccc1 Chemical compound Brc(cc1)ccc1[Si+](c1ccccc1)(c1ccccc1)c1ccccc1 VKIWBMLWZKNBSO-UHFFFAOYSA-N 0.000 description 1
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- LHJKCXCCVSLPST-UHFFFAOYSA-N CC1(C)OB(c(cc2)c(cccc3)c3c2-c(cc2)ccc2[Si+](c2ccccc2)(c2ccccc2)c2ccccc2)OC1(C)C Chemical compound CC1(C)OB(c(cc2)c(cccc3)c3c2-c(cc2)ccc2[Si+](c2ccccc2)(c2ccccc2)c2ccccc2)OC1(C)C LHJKCXCCVSLPST-UHFFFAOYSA-N 0.000 description 1
- DNGQJTJOZQDEJX-UHFFFAOYSA-N CC1(C)OB(c(cc2)ccc2[SiH-](c2ccccc2)(c2ccccc2)c2ccccc2)OC1(C)C Chemical compound CC1(C)OB(c(cc2)ccc2[SiH-](c2ccccc2)(c2ccccc2)c2ccccc2)OC1(C)C DNGQJTJOZQDEJX-UHFFFAOYSA-N 0.000 description 1
- ISIMDTFAKZHXNB-UHFFFAOYSA-N CC1(C)ON(c2ccc(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)OC1(C)C Chemical compound CC1(C)ON(c2ccc(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)OC1(C)C ISIMDTFAKZHXNB-UHFFFAOYSA-N 0.000 description 1
- MQFYUZCANYLWEI-UHFFFAOYSA-N Cc(c1ccccc11)ccc1N Chemical compound Cc(c1ccccc11)ccc1N MQFYUZCANYLWEI-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- RQQDJYROSYLPPK-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 Chemical compound N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 RQQDJYROSYLPPK-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
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- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- WLBDLIPAJOWHAX-UHFFFAOYSA-N c(cc1)ccc1-c1[n-]c(-c(cc2)c(cccc3)c3c2-c(cc2)ccc2[Si+](c2ccccc2)(c2ccccc2)c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1[n-]c(-c(cc2)c(cccc3)c3c2-c(cc2)ccc2[Si+](c2ccccc2)(c2ccccc2)c2ccccc2)nc(-c2ccccc2)n1 WLBDLIPAJOWHAX-UHFFFAOYSA-N 0.000 description 1
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- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
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- 239000003599 detergent Substances 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- SORXVYYPMXPIFD-UHFFFAOYSA-N iron palladium Chemical compound [Fe].[Pd] SORXVYYPMXPIFD-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GQKZBCPTCWJTAS-UHFFFAOYSA-N methoxymethylbenzene Chemical compound COCC1=CC=CC=C1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及有机电致发光器件领域,公开了有机电致发光化合物及其应用和有机电致发光器件,该化合物具有式(I)所示的结构,其中,在式(I)中,X为Si或C;R1、R2、R3和R4各自独立地选自H和C1‑6的烷基。本发明提供的前述有机电致发光化合物在用于有机发光器件中时,能够发蓝光;并且该有机电致发光化合物在用作蓝色有机电致发光材料中时能够显著提高发光效率以及延长材料的使用寿命。
Description
技术领域
本发明涉及有机电致发光器件领域,具体涉及一种有机电致发光化合物、该有机电致发光化合物在有机电致发光器件中的应用、一种含有该有机电致发光化合物中的一种或两种以上的化合物的有机电致发光器件。
背景技术
有机电致发光(OLED)技术相比于传统的液晶技术来说,其无需背光源照射和滤色器,像素可自身发光呈现在彩色显示板上,并且,拥有超高对比度、超广可视角度、曲面、薄型等特点。
OLED的性能不仅受到发光体的影响,特别是,形成OLED的各个层的材料都对OLED的性能具有非常重要的影响,例如基底材料、空穴阻挡材料、电子传输材料、空穴传输材料和电子或激子阻挡材料、发光材料等。
目前采用的形成OLED的各个层的材料仍然存在驱动电压高、使用寿命短、电流效率和亮度均低的缺陷,尤其是蓝色有机电致发光材料的效率和寿命缺陷,致使无法获得性能较好的有机电致发光器件。
发明内容
本发明的目的是为了克服现有技术存在的蓝色有机电致发光材料的发光效率不高以及使用寿命不长的缺陷,提供一种新的有机电致发光化合物,该有机电致发光化合物在用作蓝色有机电致发光材料中时能够显著提高发光效率以及延长材料的使用寿命。
为了实现上述目的,本发明的第一方面提供一种有机电致发光化合物,该化合物具有式(I)所示的结构,
其中,在式(I)中,
X为Si或C;
R1、R2、R3和R4各自独立地选自H和C1-6的烷基;
R为取代或未取代的含有或者不含有N原子的芳香环,且其中的取代基各自独立地选自苯基、联苯基、吡啶基、吡啶基取代的苯基、苯基取代的苯并咪唑基和苯基取代的三嗪基中的至少一种。
本发明的第二方面提供第一方面所述的有机电致发光化合物在有机电致发光器件中的应用。
本发明的第三方面提供一种含有第一方面所述的有机电致发光化合物中的一种或两种以上的化合物的有机电致发光器件。
本发明提供的前述有机电致发光化合物能够调控有机电致发光材料的HOMO能级和LUMO能级,同时能够使含有该有机电致发光化合物的有机电致发光材料具备较高的电子迁移率,从而提高发光效率。
本发明提供的前述有机电致发光化合物在用于有机发光器件中时,能够发蓝光;并且该有机电致发光化合物在用作蓝色有机电致发光材料中时能够显著提高发光效率以及延长材料的使用寿命。
具体实施方式
在本文中所披露的范围的端点和任何值都不限于该精确的范围或值,这些范围或值应当理解为包含接近这些范围或值的值。对于数值范围来说,各个范围的端点值之间、各个范围的端点值和单独的点值之间,以及单独的点值之间可以彼此组合而得到一个或多个新的数值范围,这些数值范围应被视为在本文中具体公开。
如前所述,本发明的第一方面提供了一种有机电致发光化合物,该化合物具有式(I)所示的结构,
其中,在式(I)中,
X为Si或C;
R1、R2、R3和R4各自独立地选自H和C1-6的烷基;
R为取代或未取代的含有或者不含有N原子的芳香环,且其中的取代基各自独立地选自苯基、联苯基、吡啶基、吡啶基取代的苯基、苯基取代的苯并咪唑基和苯基取代的三嗪基中的至少一种。
在所述式(I)中,R1、R2、R3和R4的取代位置在相应的芳香环上均可以是任意的。
根据一种优选的具体实施方式,在式(I)中,
R1、R2、R3和R4各自独立地选自H和C1-3的烷基;以及
形成R的所述取代或未取代的含有或者不含有N原子的芳香环中的芳香环为以下式1至式6中的任意一种,且所述芳香环任选由选自苯基、联苯基、吡啶基、吡啶基取代的苯基、苯基取代的苯并咪唑基和苯基取代的三嗪基中的至少一种取代基取代:
式4中的R11和R11`各自独立地为H、苯基或吡啶基,或者R11和R11`中的一个为单键且与式(I)中的萘基直接连接;
式5中的X1、X2、X3和X4为C或N,且X1、X2、X3和X4中的至少一个为N,以及式5中的R12为苯基或吡啶基,或者R12为单键且与式(I)中的萘基直接连接。
在前述优选的具体实施方式中,式1至式6所示的芳香环可以与本发明的式(I)中的萘基以任意的位置进行连接,并且,式1至式6所示的芳香环中可能含有的取代基的个数并没有特别的限定,例如可以为1-3个;以及对式1至式6所示的芳香环中可能含有的取代基的取代位置也没有特别的限定,可以是任意的能够被取代的位置。
根据另一种更优选的具体实施方式,在本发明中,在式(I)中,R1、R2、R3和R4均为H。
根据一种特别优选的具体实施方式,在本发明中,式(I)所示的结构的化合物选自权利要求4中所列举的具体化合物中的任意一种。
根据另一种更优选的具体实施方式,为了进一步提高有机发光器件的发光效率,在本发明中,式(I)所示的结构的化合物选自权利要求5中所列举的具体化合物中的任意一种。
本发明对制备前述有机电致发光化合物的具体方法没有特别的限定,本领域技术人员可以根据本发明提供的具体结构式以及本发明的具体实例部分列举的几个具体化合物的制备方法而获得本发明的全部有机电致发光化合物的制备方法。本发明在本文中没有具体列举全部有机电致发光化合物的制备方法,本领域技术人员不能理解为对本发明的限制。
如前所述,本发明的第二方面提供了前述第一方面所述的有机电致发光化合物在有机电致发光器件中的应用。
如前所述,本发明的第三方面提供了一种含有前述第一方面所述的有机电致发光化合物中的一种或两种以上的化合物的有机电致发光器件。
优选情况下,所述有机电致发光化合物存在于该有机电致发光器件的电子传输层、发光层和空穴阻挡层中的至少一层中。
根据一种优选的具体实施方式,所述有机电致发光化合物存在于该有机电致发光器件的发光层中,且作为所述发光层中的主体材料。
优选情况下,在所述发光层中,所述主体材料中还含有蒽类衍生物、咔唑类衍生物、芴类衍生物、芳胺类衍生物、有机硅类衍生物、咔唑-三嗪类衍生物、磷氧基类衍生物中的至少一种化合物。
优选地,所述蒽类衍生物具有如下所示的通式:
优选地,所述磷氧基类衍生物具有如下所示的通式:
在前述蒽类衍生物和磷氧基类衍生物的通式中,R11、R12、R13、R14、R15和R16各自独立地选自单键、氢、氘、烷基、苯、二联苯、三联苯、四联苯、萘、苯基萘、蒽、菲、苯并菲、芘、芴、咔唑、噻吩、苯并噻吩、二苯并噻吩、呋喃、苯并呋喃、二苯并呋喃、吲哚、吲哚咔唑、茚并咔唑、吡啶、嘧啶、咪唑、噻唑、喹啉、异喹啉、喹喔啉、喹唑啉、卟啉、咔啉、吡嗪、哒嗪或三嗪,以及它们的取代物。
优选地,所述发光层中还含有客体材料,所述客体材料为经由磷光、荧光、TADF(热激活延迟荧光)、MLCT(金属到配体电荷转移)、HLCT(具有杂化CT态)和三线态-三线态消灭方法中的至少一种方法产生的发射的化合物。
优选地,所述客体材料选自苝的衍生物、蒽的衍生物、芘的衍生物、芴类衍生物、二苯乙烯基芳类衍生物、芳胺类衍生物、有机硅类衍生物、有机硼类衍生物、咔唑-三嗪类衍生物、吖啶类衍生物、含有酮类衍生物、砜基类衍生物、氰基衍生物和氧杂蒽类衍生物中的至少一种。
优选地,所述芘类衍生物具有如下所示的通式:
优选地,所述砜基类衍生物具有如下所示的通式:
优选地,所述酮基类衍生物具有如下所示的通式:
在前述芘类衍生物、砜基类衍生物和酮基类衍生物的通式中,R17、R18、R19、R20、R21、R22和R23各自独立地选自单键、氢、氘、烷基、苯、二联苯、三联苯、四联苯、萘、苯基萘、蒽、菲、苯并菲、芘、芴、咔唑、噻吩、苯并噻吩、二苯并噻吩、呋喃、苯并呋喃、二苯并呋喃、吲哚、吲哚咔唑、茚并咔唑、吡啶、嘧啶、咪唑、噻唑、喹啉、异喹啉、喹喔啉、喹唑啉、卟啉、咔啉、吡嗪、哒嗪或三嗪,以及它们的取代物。
根据一种优选的具体实施方式,所述有机电致发光器件包括依次层叠设置的基板、阳极、空穴注入层(HIL)、空穴传输层(HTL)、任选的电子阻挡层、发光层(EML)、任选的空穴阻挡层、电子传输层(ETL)、电子注入层(EIL)和阴极。
优选地,该有机电致发光器件中还含有第一覆盖层和/或第二覆盖层,所述第一覆盖层设置在所述阳极的外表面,以及所述第二覆盖层设置在所述阴极的外表面。
例如所述有机电致发光器件可以依次层叠设置第一覆盖层、阳极、空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、发光层(EML)、空穴阻挡层(HBL)、电子传输层(ETL)、电子注入层(EIL)、阴极和第二覆盖层。
优选情况下,所述第一覆盖层和所述第二覆盖层中各自独立地含有本发明第一方面所述的有机电致发光化合物。
本发明的所述基板可以使用玻璃基板、塑料基板或金属基板。
优选地,形成所述阳极的阳极材料选自氧化铟锡、氧化铟锌和二氧化锡中的一种或多种。其中,该阳极材料形成的阳极活性层的厚度例如可以为100-1700埃。
优选地,形成所述空穴注入层的材料为空穴注入材料,以及形成所述空穴传输层的材料为空穴传输材料,以及所述空穴注入材料和空穴传输材料选自芳香族胺衍生物(例如NPB、SqMA1)、六氮杂苯并菲衍生物(例如HACTN)、吲哚并咔唑衍生物、导电聚合物(例如PEDOT/PSS),酞菁或卟啉衍生物、二苯并茚并芴胺、螺二芴胺。
所述空穴注入层(HIL)和空穴传输层(HTL)例如可采用如下通式的芳香族胺衍生物形成:
上述通式中的R1至R9的基团各自独立地选自单键、氢、氘、烷基、苯、二联苯、三联苯、萘、蒽、菲、苯并菲、芘、芴、二甲基芴、螺二芴、咔唑、噻吩、苯并噻吩、二苯并噻吩、呋喃、苯并呋喃、二苯并呋喃、吲哚、吲哚咔唑、茚并咔唑、吡啶、嘧啶、咪唑、噻唑、喹啉、异喹啉、喹喔啉、喹唑啉、卟啉、咔啉、吡嗪、哒嗪或三嗪。
优选地,空穴注入层厚度为100-2000埃,更优选为200-600埃。
优选地,空穴传输层厚度为100-1000埃,更优选为200-400埃。
优选地,形成所述电子传输层的材料还能够选自金属络合物、苯并咪唑衍生物、嘧啶衍生物、吡啶衍生物、喹啉衍生物和喹喔啉衍生物中的至少一种物质。优选地,所述电子传输层的厚度为100-600埃。
所述电子阻挡层的形成材料不受特别限制,一般情况下,能够具备如下第1或/和第2个条件的化合物均可考虑采用:
第1:具备较高的LUMO能级,其目的就是减少离开发光层的电子数目,从而提高电子和空穴在发光层的复合几率。
第2:具备较大的三线态能量,其目的就是减少离开发光层的激子数量,从而提高激子转换发光的效率。
形成所述电子阻挡层的材料包括但不限于芳香族胺衍生物(例如NPB)、螺二芴胺(例如SpMA2),其中部分电子阻挡材料和空穴注入材料和空穴传输材料的结构类似。优选电子阻挡层的厚度为50-600埃。
形成所述空穴阻挡层的材料优选为具备如下第1或/和第2个条件的化合物:
第1:具备较高的HOMO能级,其目的就是减少离开发光层的空穴数目,从而提高电子和空穴在发光层的复合几率。
第2:具备较大的三线态能量,其目的就是减少离开发光层的激子数量,从而提高激子转换发光的效率。
形成所述空穴阻挡层的材料例如还可以含有菲啰啉衍生物(例如Bphen,BCP),苯并菲衍生物,苯并咪唑衍生物。优选地,所述空穴阻挡层的厚度为50-600埃。
优选地,所述电子注入层材料为LiF、Al2O3、MnO等中的一种或多种。优选地,电子注入层的厚度为1-50埃。
优选地,所述阴极材料为Al、Mg和Ag中的一种或多种。优选地,阴极层的厚度为800-1500埃。
本发明的有机电致发光器件优选借助于升华方法涂布一个层或者多个层。在这种情况下,在真空升华系统中,在小于10-3Pa、优选小于10-6Pa的初始压力下通过气相沉积施加本发明提供的化合物。
本发明的有机电致发光器件优选通过有机气相沉积方法或者借助于载气升华来涂布一个层或者多个层。在这种情况下,在10-6Pa至100Pa的压力下施加所述材料。这种方法特别的例子是有机蒸镀喷印方法,其中本发明提供的化合物通过喷嘴直接施加并形成器件结构。
本发明的有机电致发光器件优选通过光引发热成像或热转印,来形成一层或者多层结构。
本发明的有机电致发光器件优选将本发明的化合物配制成溶液,通过旋涂或借助于任何印刷方式,例如丝网印刷、柔性版印刷、喷墨印刷、平版印刷,更优选的是喷墨印刷,来形成一个层或者多个层结构。但是,用这种方法来制作多个层时,容易出现层与层之间的破坏,即当制作完成一个层时,再用溶液制作另外一个层时,溶液中的溶剂会破坏掉已经形成的层,这不利于器件制作。本发明提供的化合物能够通过结构修饰取代,让本发明的化合物在加热或者紫外曝光的情况下发生交联作用,从而保持完整的层而不会被破坏。本发明的化合物另外可从溶液中施加,并且通过后续的在聚合物网络中的交联或者固定在相应的层中。
优选地,通过从溶液中施加一个或者多个层和通过升华方法施加一个或者多个层来制造本发明的有机电致发光器件。
本发明的制备有机电致发光器件的优选的溶剂选自甲苯、苯甲醚、邻二甲苯、间二甲苯、对二甲苯、苯甲酸甲酯、均三甲苯、萘满、邻二甲氧基苯、THF、甲基-THF、THP、氯苯、苯氧基甲苯,特别是3-苯氧基甲苯、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯烷酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、苯并噻唑、苯甲酸丁酯、异丙醇、异丙苯、环己醇、环己酮、环己基苯、十氢萘、十二烷基苯、苯甲酸甲酯、NMP、对甲基异并基苯、苯乙醚、1,4-二异丙基苯、二苄醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二丁基醚、二乙二醇单丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-异丙基萘、戊苯、己苯、庚苯、辛苯、1,1-双(3,4-二甲基苯基)乙烷、2-庚醇、3-庚醇,或这些溶剂的混合物。
优选地,在制备本发明的有机电致发光器件时,将本发明的化合物和其它化合物先充分混合,然后再通过上述施加方式,来形成一个层或者多个层。更加优选的是,在真空升华系统中,在小于10-3Pa、优选小于10-6Pa的初始压力下,通过气相沉积施加各化合物,来形成一个层或者多个层。
以下通过具体实例对本发明的技术方案进行详细描述。
在没有特别说明的情况下,使用的各种原料均来自商购。
制备例1:化合物1-1的合成
中间体1-1-1的合成:将0.0482mol的4-溴-四苯基硅烷溶于200ml的1,4-二氧六环溶剂中,通氮气下搅拌,加入0.0482mol的联硼酸频哪醇酯、0.1205mol乙酸钾、0.48mmol的二茂铁二氯化钯,升温至回流反应,4h后HPLC检测原料基本反应完毕,将反应液减压旋干,将残余物通过柱层析得到中间体1-1-1(收率:81%)。
计算值C30H31BO2Si:462.46±1。1H-NMR(400MHz,CDCl3)(ppm)δ=1.24~1.24(12H,s),7.34~7.46(14H,m),7.55~7.56(3H,m),7.85~7.86(2H,m)。
中间体1-1-2的合成:将0.043mol的中间体1-1-1溶于200ml的1,4-二氧六环溶剂中,通氮气下搅拌,加入0.043mol的1-溴-4-碘萘、0.129mol的K2CO3、0.43mmol四(三苯基膦)钯,升温至回流反应,5h后HPLC检测原料基本反应完毕,将反应液减压旋干,将残余物通过柱层析得到中间体1-1-2(收率:65%)。
计算值C34H25BrSi:541.55±1。1H-NMR(400MHz,CDCl3)(ppm)δ=7.37~7.55(17H,m),7.66~7.74(2H,m),7.86~7.89(3H,m),8.03~8.04(1H,m),8.59~8.60(2H,m)。
中间体1-1-3的合成:合成方法同中间体1-1-1的合成,得到中间体1-1-3(收率79%)。
计算值C40H37BO2Si:588.62±1。1H-NMR(400MHz,CDCl3)(ppm)δ=1.24~1.24(12H,s),7.34~7.55(19H,m),7.66~7.67(1H,m),7.89~7.95(3H,m),8.08~8.09(1H,m),8.55~8.56(1H,m)。
化合物1-1的合成:合成方法同中间体1-1-2的合成,得到化合物1-1(收率58%)。
计算值C49H35N3Si:693.91±1。1H-NMR(400MHz,CDCl3)(ppm)δ=7.37~7.55(25H,m),7.86~7.89(2H,d),8.01~8.01(2H,s),8.28~8.30(4H,m),8.55~8.57(2H,m)。
制备例2:化合物1-5的合成
化合物1-5的合成:合成方法同中间体1-1-2的合成,得到化合物1-5(收率60%)。
计算值C46H32N2Si:640.85±1。1H-NMR(400MHz,CDCl3)(ppm)δ=7.37~7.58(21H,m),7.81~7.82(1H,m),7.89~7.91(2H,m),8.04~8.10(3H,m),8.38~8.40(1H,m),8.52~8.55(3H,m),8.83~8.85(1H,m)。
制备例3:化合物1-10的合成
中间体1-10-1的合成:将0.1mol的4-硼酸频哪醇酯-四苯基硅烷溶于460ml的1,4-二氧六环溶剂中,通氮气下搅拌,加入0.11mol的1-溴-4-碘萘、0.25mol的K2CO3、0.001mol的二茂铁二氯化钯,升温至回流反应,5h后HPLC检测原料基本反应完毕,将反应液减压旋干,将残余物通过柱层析得到中间体1-10-1(收率:65%)。
计算值C34H25BrSi:541.55±1。1H-NMR(400MHz,CDCl3)(ppm)δ=7.37~7.55(17H,m),7.66~7.74(2H,m),7.86~7.89(3H,m),8.03~8.04(1H,d),8.59~8.60(2H,m)。
中间体1-10-2的合成:将0.065mol的中间体1-10-1溶于350ml的1,4-二氧六环溶剂中,通氮气下搅拌,加入0.065mol的联硼酸频哪醇酯、0.1625mol乙酸钾、0.00065mol的二茂铁二氯化钯,升温至回流反应,4h后HPLC检测原料基本反应完毕,将反应液减压旋干,将残余物通过柱层析得到中间体1-10-2(收率:68%)。
计算值C40H37BO2Si:588.62±1。1H-NMR(400MHz,CDCl3)(ppm)δ=1.24~1.24(12H,s),7.37~7.55(19H,m),7.66~7.67(1H,d),7.89~7.95(3H,m),8.08~8.09(1H,m),8.55~8.56(1H,m)。
化合物1-10的合成:合成方法同中间体1-10-1的合成,得到化合物1-10(收率69%)。
计算值C50H36N2Si:692.92±1。1H-NMR(400MHz,CDCl3)(ppm)δ=7.37~7.55(25H,m),7.79~7.80(4H,m),7.89~7.90(2H,m),8.01~8.01(2H,s),8.23~8.23(1H,s),8.55~8.56(2H,m)。
制备例4:化合物2-9的合成
中间体2-9-1的合成:合成方法同中间体1-13-1的合成,得到化合物2-9-1(收率57%)。
计算值C35H25Br:525.48±1。1H-NMR(400MHz,CDCl3)(ppm)δ=7.11~7.12(6H,m),7.26~7.33(13H,m),7.66~7.74(2H,m),7.86~7.87(1H,d),8.03~8.04(1H,d),8.59~8.60(2H,m)。
中间体2-9-2的合成:合成方法同中间体1-13-2的合成,得到化合物2-9-2(收率61%)。
计算值C41H37BO2:572.54±1。1H-NMR(400MHz,CDCl3)(ppm)δ=1.24~1.24(12H,s),7.11~7.12(6H,m),7.26~7.33(13H,m),7.55~7.56(2H,m),7.66~7.67(1H,m),7.95~7.96(1H,d),8.08~8.09(1H,m),8.55~8.56(1H,m)。
化合物2-9的合成:合成方法同中间体1-13-1的合成,得到化合物2-9(收率69%)。
计算值C54H38N2:714.89±1。1H-NMR(400MHz,CDCl3)(ppm)δ=7.11~7.12(6H,m),7.22~7.33(17H,m),7.45~7.59(8H,m),7.85~7.86(2H,d),8.01~8.01(2H,s),8.55~8.56(3H,m)。
实施例1:制备有机发光器件
依次用蒸馏水和甲醇超声洗涤具有约1500埃厚度的氧化铟锡(ITO)电极(第一电极,阳极)的玻璃衬底之后,将经洗涤的玻璃衬底干燥,移到等离子体清洁系统,然后使用氧等离子体清洁约5分钟。然后将所述玻璃衬底装载到真空沉积设备中。
将2-TNATA真空沉积到所述玻璃衬底的ITO电极上以形成具有约500埃厚度的HIL;将NPB真空沉积到空穴注入层上形成具有约200埃厚度的HTL。
将所述化合物1-1沉积在所述空穴传输区域上以形成具有约300埃厚度的EML。
随后,将ET-1真空沉积在所述EML上以形成具有约250埃厚度的ETL。然后,将LiF沉积在ETL上以形成具有约5埃厚度的EIL,并将Al沉积在所述EIL上至约1000埃的厚度以形成第二电极(阴极),由此完成有机发光器件的制造。
其余实施例
采用与实施例1相似的方法制备其余实施例的有机发光器件,所不同的是,采用表1所示的化合物替换实施例1中的化合物1-1。
对比例1
采用与实施例1中相似的方法制备有机发光器件,所不同的是,采用化合物BD-1替换实施例1中的化合物1-1。
评价:有机发光器件的特性评价
使用电流-电压源计(Keithley 2400)和Minolta CS-1000A分光辐射谱仪测量实施例和对比实施例中的有机发光器件的驱动电压、发射效率和寿命。结果示于下表1中。
(1)相对于电压变化的电流密度变化的测量
通过使用电流-电压源计(Keithley 2400)在使电压从0伏(V)增加到约10V的同时测量流动通过所述有机发光器件的每一个的电流值,然后将其除以相应发光器件的面积以获得电流密度。
(2)相对于电压变化的亮度变化的测量
通过使用Minolta CS-1000A分光辐射谱仪在使电压从约0V增加到约10V的同时测量所述有机发光器件的亮度。
(3)发射效率的测量
基于由以上描述的测量(1)和(2)获得的电流密度、电压和亮度计算所述有机发光器件在20毫安/平方厘米(mA/cm2)的一定电流密度下的电流效率。
(4)寿命的测量
保持5000cd/m2的亮度(cd/m2),并测量电流效率(cd/A)减小至50%的时间。
表1
通过表1中的数据可以看出,由本发明的新化合物形成的有机电致发光器件具有低的驱动电压和明显较现有技术高的寿命、电流效率及亮度。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于此。在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,包括各个技术特征以任何其它的合适方式进行组合,这些简单变型和组合同样应当视为本发明所公开的内容,均属于本发明的保护范围。
Claims (10)
1.一种有机电致发光化合物,该化合物具有式(I)所示的结构,
其中,在式(I)中,
X为Si或C;
R1、R2、R3和R4各自独立地选自H和C1-6的烷基;
R为取代或未取代的含有或者不含有N原子的芳香环,且其中的取代基各自独立地选自苯基、联苯基、吡啶基、吡啶基取代的苯基、苯基取代的苯并咪唑基和苯基取代的三嗪基中的至少一种。
2.根据权利要求1所述的化合物,其中,在式(I)中,
R1、R2、R3和R4各自独立地选自H和C1-3的烷基;以及
形成R的所述取代或未取代的含有或者不含有N原子的芳香环中的芳香环为以下式1至式6中的任意一种,且所述芳香环任选由选自苯基、联苯基、吡啶基、吡啶基取代的苯基、苯基取代的苯并咪唑基和苯基取代的三嗪基中的至少一种取代基取代:
式4中的R11和R11`各自独立地为H、苯基或吡啶基,或者R11和R11`中的一个为单键且与式(I)中的萘基直接连接;
式5中的X1、X2、X3和X4为C或N,且X1、X2、X3和X4中的至少一个为N,以及式5中的R12为苯基或吡啶基,或者R12为单键且与式(I)中的萘基直接连接。
3.根据权利要求2所述的化合物,其中,在式(I)中,R1、R2、R3和R4均为H。
4.根据权利要求3所述的化合物,其中,式(I)所示的结构的化合物选自以下化合物中的任意一种:
5.根据权利要求4所述的化合物,其中,式(I)所示的结构的化合物选自以下化合物中的任意一种:
6.权利要求1-5中任意一项所述的有机电致发光化合物在有机电致发光器件中的应用。
7.一种含有权利要求1-5中任意一项所述的有机电致发光化合物中的一种或两种以上的化合物的有机电致发光器件;优选地,
所述有机电致发光化合物存在于该有机电致发光器件的电子传输层、发光层和空穴阻挡层中的至少一层中。
8.根据权利要求7所述的有机电致发光器件,其中,所述有机电致发光化合物存在于该有机电致发光器件的发光层中,且作为所述发光层中的主体材料。
9.根据权利要求8所述的有机电致发光器件,其中,所述发光层中还含有客体材料,所述客体材料为经由磷光、荧光、TADF、MLCT、HLCT和三线态-三线态消灭方法中的至少一种方法产生的发射的化合物。
10.根据权利要求7-9中任意一项所述的有机电致发光器件,其中,所述有机电致发光器件包括依次层叠设置的基板、阳极、空穴注入层、空穴传输层、任选的电子阻挡层、发光层、任选的空穴阻挡层、电子传输层、电子注入层和阴极。
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