CN109206431B - Organic electroluminescent compound, application thereof and organic electroluminescent device - Google Patents
Organic electroluminescent compound, application thereof and organic electroluminescent device Download PDFInfo
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- CN109206431B CN109206431B CN201810866667.8A CN201810866667A CN109206431B CN 109206431 B CN109206431 B CN 109206431B CN 201810866667 A CN201810866667 A CN 201810866667A CN 109206431 B CN109206431 B CN 109206431B
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- organic electroluminescent
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 122
- -1 diphenylamino group Chemical group 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000000463 material Substances 0.000 abstract description 36
- 239000010410 layer Substances 0.000 description 102
- 239000000543 intermediate Substances 0.000 description 65
- 238000006243 chemical reaction Methods 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 39
- 238000002360 preparation method Methods 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 238000010438 heat treatment Methods 0.000 description 29
- 238000003756 stirring Methods 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
- 238000004440 column chromatography Methods 0.000 description 28
- 239000002994 raw material Substances 0.000 description 26
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 26
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 26
- 239000012295 chemical reaction liquid Substances 0.000 description 24
- 238000010992 reflux Methods 0.000 description 24
- 238000001035 drying Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 229960002645 boric acid Drugs 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 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 7
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- PFMTUGNLBQSHQC-UHFFFAOYSA-N 4,5-diazafluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CN=C3C2=N1 PFMTUGNLBQSHQC-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-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
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-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
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 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 5
- 239000007818 Grignard reagent Substances 0.000 description 4
- 150000001454 anthracenes Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 125000005580 triphenylene group Chemical group 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 3
- GIMVCZMZRZGDTL-UHFFFAOYSA-N 1-bromo-3-chloro-2-iodobenzene Chemical compound ClC1=CC=CC(Br)=C1I GIMVCZMZRZGDTL-UHFFFAOYSA-N 0.000 description 3
- 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 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
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- 230000007547 defect Effects 0.000 description 3
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- 238000005516 engineering process Methods 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
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 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 3
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- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
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- 150000003220 pyrenes Chemical class 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
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- 238000007740 vapor deposition Methods 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
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- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 2
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
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- 238000004132 cross linking Methods 0.000 description 2
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- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
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- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
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- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
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- 150000002894 organic compounds Chemical class 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
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- 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
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- 235000011056 potassium acetate Nutrition 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- 238000007650 screen-printing Methods 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
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- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Abstract
The invention relates to the field of organic electroluminescent devices, and discloses an organic electroluminescent compound, application thereof and an organic electroluminescent device, wherein the compound has a structure shown in a formula (I). The organic electroluminescent compound provided by the invention can improve the utilization rate of excitons of a light-emitting layer of an organic electroluminescent device when being used in the organic electroluminescent device, particularly as a light-emitting layer material. In particular, the organic electroluminescent compounds according to the invention are capable of emitting blue light in organic electroluminescent devices.
Description
Technical Field
The invention relates to the field of organic electroluminescent devices, in particular to an organic electroluminescent compound, application of the organic electroluminescent compound in an organic electroluminescent device, and an organic electroluminescent device containing one or more than two compounds in the organic electroluminescent compound.
Background
Compared with the traditional liquid crystal technology, the organic electroluminescence (OLED) technology does not need backlight source irradiation and a color filter, pixels can emit light to be displayed on a color display panel, and the OLED technology has the characteristics of ultrahigh contrast, ultra-wide visual angle, high reaction speed, low energy consumption, curved surface, thinness and the like.
Organic electroluminescence is a double-injection type light-emitting device, and electric energy is directly converted into light energy of organic semiconductor material molecules.
The organic light emitting element generally includes a structure of an organic layer between a cathode and an anode, and the organic layer generally includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied to the anode and the cathode, holes are injected from the anode side to the light-emitting layer, electrons are injected from the cathode side to the light-emitting layer, the injected holes and electrons combine in the light-emitting layer to form excitons, and the excitons emit light when returning to the ground state.
The performance of the OLED is improved, and the light emitting efficiency and stability are improved mainly. The properties of OLEDs are influenced, in particular, by the materials forming the individual layers of the OLED, which have a very important influence on the properties of the OLED, such as substrate materials, hole-blocking materials, electron-transporting materials, hole-transporting materials and electron-or exciton-blocking materials, light-emitting materials, etc.
The currently used materials for forming the layers of the OLED still have the defects of high driving voltage, short service life, low current efficiency and low brightness, especially the defects of efficiency and life of the blue organic electroluminescent material.
Disclosure of Invention
The present invention aims to overcome the aforementioned defects in the prior art, and provides an organic electroluminescent compound capable of adjusting the HOMO level and the LUMO level of an organic electroluminescent material, and at the same time, the organic electroluminescent material containing the organic electroluminescent compound has high electron mobility and hole mobility, thereby improving the luminous efficiency and brightness, and reducing the driving voltage.
The inventor of the present invention finds in research that the organic electroluminescent compound having the structure shown in formula (I) provided by the present invention has good thermodynamic stability, good film-forming property, and appropriate triplet state energy level and energy gap when used as an organic electroluminescent material, and can significantly improve the luminous efficiency and prolong the service life of the material. Accordingly, the inventors have completed the technical solution of the present invention.
In order to achieve the above object, a first aspect of the present invention provides an organic electroluminescent compound having a structure represented by formula (I),
in the structure shown in the formula (I),
x is O or S;
z is Si or C;
Y1、Y2、Y3、Y4、Y5、Y6、Y7and Y8Two of the atoms are N atoms, the remaining six atoms are C atoms, and the two N atoms are not adjacent;
R1and R2Each independently selected from at least one of H, a substituted or unsubstituted nitrogen-containing aromatic heterocyclic group, a substituted or unsubstituted diphenylamine group and a substituted phenyl group;
R1and R2Wherein the substituents optionally present are each independently selected from C1-4At least one of an alkyl group, a phenyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a carbazolyl group, a dianilino group, and a phenyl-substituted carbazolyl group.
A second aspect of the present invention provides the use of an organic electroluminescent compound as described in the first aspect above in an organic electroluminescent device.
A third aspect of the present invention provides an organic electroluminescent device comprising one or two or more of the organic electroluminescent compounds described in the first aspect.
When the organic electroluminescent compound provided by the invention is used in an organic light-emitting device, particularly as a light-emitting layer material, the utilization rate of excitons of a light-emitting layer of the organic electroluminescent device can be improved. In particular, the organic electroluminescent compounds according to the invention are capable of emitting blue light in organic electroluminescent devices.
The technical scheme of the invention also has the following beneficial technical effects: the organic electronic luminescent device adopting the organic electroluminescent compound can reduce the driving voltage, improve the luminous efficiency and prolong the service life.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
As described above, the first aspect of the present invention provides an organic electroluminescent compound having a structure represented by the formula (I),
in the structure shown in the formula (I),
x is O or S;
z is Si or C;
Y1、Y2、Y3、Y4、Y5、Y6、Y7and Y8Two of the atoms are N atoms, the remaining six atoms are C atoms, and the two N atoms are not adjacent;
R1and R2Each independently selected from at least one of H, a substituted or unsubstituted nitrogen-containing aromatic heterocyclic group, a substituted or unsubstituted diphenylamine group and a substituted phenyl group;
R1and R2Wherein the substituents optionally present are each independently selected from C1-4At least one of an alkyl group, a phenyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a carbazolyl group, a dianilino group, and a phenyl-substituted carbazolyl group.
In the present invention, "C1-4The "alkyl group of (1)" includes methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl.
Preferably, the nitrogen-containing heteroaromatic tricyclic ring in the substituted or unsubstituted nitrogen-containing heteroaromatic tricyclic group is a tricyclic ring represented by formula (a1) or formula (a2), and any position in the tricyclic ring represented by formula (a1) or formula (a2) which can be bonded is connected with the mother nucleus in formula (I) through a C-C bond or a C-N bond;
wherein Y in formula (a2) is O, S, C or N atom;
and the C atom and/or the N atom in the tricyclic ring represented by the formula (a1) and the formula (a2) is optionally substituted by a group selected from C1-4Substituted with at least one group selected from the group consisting of alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, dianilinyl, and phenyl-substituted carbazolyl;
preferably, the nitrogen-containing aromatic heterocyclic ring in the substituted or unsubstituted nitrogen-containing aromatic heterocyclic ring group of the present invention is selected from tetracyclic rings represented by the formula (b1) and/or the formula (b2),
and the C atom in the tetracyclic ring represented by formula (b1) and formula (b2) is optionally substituted by a group selected from C1-4Is substituted with at least one of alkyl, phenyl and biphenyl.
Preferably, the nitrogen-containing heteroaromatic pentacyclic ring in the substituted or unsubstituted nitrogen-containing heteroaromatic pentacyclic group is selected from pentacycles represented by formulas (c1) to (c12),
and X in the formulae (c1) to (c12)1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11And X12Each independently selected from O, S, C and an N atom;
and the C atom and/or the N atom in the pentacyclic ring represented by the formulae (C1) to (C2) is optionally substituted by a group selected from C1-4At least one of alkyl and phenyl of (a);
according to a preferred embodiment, the structure of formula (I) is at least one of the following structures of formulae (I1) to (I5):
and, in the structures represented by the formulae (I1) to (I5), R1、R2The definitions of X and Z can correspond to the same definitions as in the preceding summary of the invention.
Several preferred embodiments of the present invention are provided below.
Embodiment mode 1:
the structure shown in the formula (I) is a compound shown in a formula (I1):
and, in the structure represented by the formula (I1), R1、R2The definitions of X and Z can correspond to the same definitions as in the preceding summary of the invention.
Embodiment mode 2:
the structure shown in the formula (I) is any one of the following specific compounds:
embodiment mode 3:
the structure shown in the formula (I) is a compound shown in a formula (I2):
and, in the structure represented by the formula (I2), R1、R2The definitions of X and Z can correspond to the same definitions as in the preceding summary of the invention.
Embodiment 4:
the structure shown in the formula (I) is any one of the following specific compounds:
embodiment 5:
the structure shown in the formula (I) is a compound shown in a formula (I3):
and, in the structure represented by the formula (I3), R1、R2The definitions of X and Z can correspond to the same definitions as in the preceding summary of the invention.
Embodiment 6:
the structure shown in the formula (I) is any one of the following specific compounds:
embodiment 7:
the structure shown in the formula (I) is a compound shown in a formula (I4):
and, in the structure represented by the formula (I4), R1、R2The definitions of X and Z can correspond to the same definitions as in the preceding summary of the invention.
Embodiment mode 8:
the structure shown in the formula (I) is any one of the following specific compounds:
embodiment mode 9:
the structure shown in the formula (I) is a compound shown in a formula (I5):
and, in the structure represented by the formula (I5), R1、R2The definitions of X and Z can correspond to the same definitions as in the preceding summary of the invention.
Embodiment 10:
the structure shown in the formula (I) is any one of the following specific compounds:
embodiment mode 11:
the structure shown in the formula (I) is any one of the following specific compounds:
preferably, the first and second electrodes are formed of a metal,
the structure shown in the formula (I) is any one of the following specific compounds:
the synthesis method of the organic electroluminescent compound provided by the present invention is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the structural formula of the organic electroluminescent compound provided by the present invention in combination with the preparation method of the preparation example.
Further, some preparation methods of the organic electroluminescent compounds are exemplarily given in the preparation examples of the present invention, and those skilled in the art can obtain the organic electroluminescent compounds provided by the present invention according to the preparation methods of these exemplary preparation examples. The present invention will not be described in detail herein with respect to specific methods of preparing the various compounds of the present invention, which should not be construed as limiting the invention to those skilled in the art.
A second aspect of the present invention provides the use of an organic electroluminescent compound as described in the first aspect above in an organic electroluminescent device.
A third aspect of the present invention provides an organic electroluminescent device comprising one or two or more of the organic electroluminescent compounds described in the first aspect.
Preferably, the organic electroluminescent compound is present in at least one of an electron transport layer, a light emitting layer and a hole blocking layer of the organic electroluminescent device.
Preferably, the organic electroluminescent compound is present in a light-emitting layer of the organic electroluminescent device.
Preferably, the organic electroluminescent compound serves as a light emitting layer of the organic electroluminescent device.
Preferably, the organic electroluminescent compound is used as a host material in the light-emitting layer.
Preferably, in the light-emitting layer, the host material further contains at least one compound selected from the group consisting of anthracene derivatives, carbazole derivatives, fluorene derivatives, arylamine derivatives, organosilicon derivatives, carbazole-triazine derivatives, and phosphoxy derivatives.
Preferably, the anthracene derivative has the general formula shown below:
preferably, the phosphorus oxy derivative has the following general formula:
in the general formulae of the above anthracene derivatives and phosphonoxy derivatives, R11、R12、R13、R14、R15And R16Each independently selected from the group consisting of a single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine, and substitutions thereof.
Preferably, a guest material, which is an emissive compound generated via at least one of phosphorescence, fluorescence, TADF (thermally activated delayed fluorescence), MLCT (metal to ligand charge transfer), HLCT (with hybrid CT state), and triplet-triplet annihilation method, is further contained in the light emitting layer.
Preferably, the guest material is selected from at least one of perylene derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, distyrylaryl derivatives, arylamine derivatives, silicone derivatives, organoboron derivatives, carbazole-triazine derivatives, acridine derivatives, ketone-containing derivatives, sulfone-based derivatives, cyano derivatives, and xanthene derivatives.
Preferably, the pyrene derivative has the following general formula:
preferably, the sulfone-based derivative has a general formula as shown below:
preferably, the ketone-based derivative has a general formula shown below:
in the general formulae of the foregoing pyrene derivatives, sulfone-based derivatives and ketone-based derivatives, R17、R18、R19、R20、R21、R22And R23Each independently selected from the group consisting of a single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine, and substitutions thereof.
According to a preferred embodiment, the organic electroluminescent device comprises a substrate, an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an optional electron blocking layer, an emission layer (EML), an optional hole blocking layer, an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and a cathode, which are sequentially stacked.
Preferably, the organic electroluminescent device further comprises a first cover layer and/or a second cover layer, wherein the first cover layer is arranged on the outer surface of the anode, and the second cover layer is arranged on the outer surface of the cathode.
For example, the organic electroluminescent device may sequentially stack a first capping layer, an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), an emission layer (EML), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), a cathode, and a second capping layer.
Preferably, the first capping layer and the second capping layer each independently contain the organic compound according to the first aspect of the present invention.
The substrate of the present invention may use a glass substrate, a plastic substrate, or a metal substrate.
Preferably, the anode material forming the anode is selected from one or more of indium tin oxide, indium zinc oxide and tin dioxide. The thickness of the anode active layer formed by the anode material can be, for example, 100-1700 angstroms.
Preferably, the material forming the hole injection layer is a hole injection material, and the material forming the hole transport layer is a hole transport material, and the hole injection material and hole transport material are selected from aromatic amine derivatives (e.g. NPB, SqMA1), hexaazatriphenylene derivatives (e.g. HACTN), indolocarbazole derivatives, conductive polymers (e.g. PEDOT/PSS), phthalocyanine or porphyrin derivatives, dibenzoindenofluorenamine, spirobifluorenylamine.
The Hole Injection Layer (HIL) and the Hole Transport Layer (HTL) can be formed, for example, using an aromatic amine derivative of the following general formula:
the groups R1 to R9 in the above general formula are each independently selected from a single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, dimethylfluorene, spirobifluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine.
Preferably, the hole injection layer has a thickness of 100-2000 angstroms, more preferably 200-600 angstroms.
Preferably, the hole transport layer has a thickness of 100-1000 angstroms, more preferably 200-400 angstroms.
Preferably, the material forming the electron transport layer can also be selected from at least one of a metal complex, a benzimidazole derivative, a pyrimidine derivative, a pyridine derivative, a quinoline derivative, and a quinoxaline derivative. Preferably, the thickness of the electron transport layer is 100-600 angstroms.
The material for forming the electron blocking layer is not particularly limited, and in general, any compound capable of satisfying the following conditions 1 and/or 2 can be considered:
1, the method comprises the following steps: the luminescent layer has a higher LUMO energy level, and the purpose of the luminescent layer is to reduce the number of electrons leaving the luminescent layer, so that the recombination probability of the electrons and holes in the luminescent layer is improved.
And 2, a step of: the light emitting layer has larger triplet energy, and the purpose of the light emitting layer is to reduce the number of excitons which leave the light emitting layer, thereby improving the efficiency of exciton conversion and light emission.
Materials forming the electron blocking layer include, but are not limited to, aromatic amine derivatives (e.g., NPB), spirobifluorene amines (e.g., SpMA2), in which the structures of a portion of the electron blocking material and the hole injecting material and the hole transporting material are similar. The electron blocking layer preferably has a thickness of 50 to 600 angstroms.
The material forming the hole blocking layer is preferably a compound having the following conditions 1 and/or 2:
1, the method comprises the following steps: the organic electroluminescent device has a higher HOMO energy level, and the purpose of the organic electroluminescent device is to reduce the number of holes leaving a light-emitting layer, so that the recombination probability of electrons and holes in the light-emitting layer is improved.
And 2, a step of: the light emitting layer has larger triplet energy, and the purpose of the light emitting layer is to reduce the number of excitons which leave the light emitting layer, thereby improving the efficiency of exciton conversion and light emission.
The material forming the hole blocking layer may further contain, for example, phenanthroline derivatives (e.g., Bphen, BCP), triphenylene derivatives, benzimidazole derivatives. Preferably, the hole blocking layer has a thickness of 50 to 600 angstroms.
Preferably, the material of the electron injection layer is LiF or Al2O3MnO, etc. Preferably, the electron injection layer has a thickness of 1 to 50 angstroms.
Preferably, the cathode material is one or more of Al, Mg and Ag. Preferably, the cathode layer has a thickness of 800-.
The organic electroluminescent device of the invention is preferably coated in one layer or in a plurality of layers by means of a sublimation process. In this case, in the vacuum sublimation system, the temperature is less than 10 DEG-3Pa, preferably less than 10-6The compound provided by the present invention is applied by vapor deposition at an initial pressure of Pa.
The organic electroluminescent device of the invention is preferably coated with one layer or a plurality of layers by an organic vapor deposition method or sublimation with the aid of a carrier gas. In this case, 10-6The material is applied under a pressure of Pa to 100 Pa. A particular example of such a process is an organic vapor deposition jet printing process, wherein the compounds provided by the present invention are applied directly through a nozzle and form a device structure.
The organic electroluminescent device of the present invention is preferably formed into one or more layers by photo-induced thermal imaging or thermal transfer.
The organic electroluminescent device according to the invention is preferably prepared by formulating the compounds according to the invention in solution and forming the layer or the layer structure by spin coating or by means of any printing means, such as screen printing, flexographic printing, ink-jet printing, lithographic printing, more preferably ink-jet printing. However, when a plurality of layers are formed by this method, the layers are easily damaged, that is, when one layer is formed and another layer is formed by using a solution, the formed layer is damaged by a solvent in the solution, which is not favorable for device formation. The compound provided by the invention can be substituted by structural modification, so that the compound provided by the invention can generate crosslinking action under the condition of heating or ultraviolet exposure, and an integral layer can be kept without being damaged. The compounds according to the invention can additionally be applied from solution and fixed in the respective layer by subsequent crosslinking in the polymer network.
Preferably, the organic electroluminescent device of the invention is manufactured by applying one or more layers from a solution and one or more layers by a sublimation method.
Preferred solvents for the preparation of organic electroluminescent devices according to the invention are selected from the group consisting of toluene, anisole, o-xylene, m-xylene, p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, phenoxytoluene, in particular 3-phenoxytoluene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, benzothiazole, butyl benzoate, isopropanol, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, cyclohexanol, Methyl benzoate, NMP, p-methylisobenzene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dibutyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, 2-heptanol, 3-heptanol, or a mixture of these solvents.
Preferably, in the preparation of the organic electroluminescent device according to the invention, the compound according to the invention and the further compound are first mixed thoroughly and then applied by the above-described application method to form a layer or layers. More preferably, in the vacuum sublimation system, less than 10-3Pa, preferably less than 10-6Pa, to form a layer or layers by applying the respective compounds by vapour deposition.
The technical solution of the present invention is described in detail by specific examples below.
The various starting materials used are all commercially available, unless otherwise specified.
Preparation example 1: preparation of Compound 1-1
Synthesis of intermediate 1-1-1: adding 165ml of dioxane solvent and 5ml of water into a three-necked bottle, sequentially adding 0.1mol of benzofuran-3-boric acid, 0.1mol of o-bromoiodobenzene, 0.25mol of potassium carbonate and 0.001mol of ferrocene palladium dichloride, stirring, heating to reflux, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying reaction liquid, and carrying out column chromatography to obtain an intermediate 1-1-1 (yield is 71%).
Synthesis of intermediate 1-1-2: 0.071mol of intermediate 1-1-1 was dissolved in 200ml of tetrahydrofuran in a three-necked flask, the temperature was reduced to-78 ℃, then 40ml of n-BuLi (2.5M) was added dropwise thereto, after 30 minutes, 0.071mol of 4, 5-diazafluoren-9-one was placed therein, the temperature was raised to room temperature, and then the resulting mixture was stirred for 1 hour. After 200ml of HCl (1N) was put thereto and the resulting mixture was stirred for 30 minutes, the layers were separated to remove the solvent, and then the residue was recrystallized from ethyl acetate to give intermediate 1-1-2 (yield 50%).
Synthesis of intermediates 1-1-3: adding 0.035mol of intermediate 1-1-2 into 130ml of THF, stirring, cooling to-78 ℃, then dropwise adding 40ml of n-BuLi (2.5M), keeping the temperature for 30 minutes, then heating to room temperature, then keeping the temperature for 2 hours at room temperature, cooling to-78 ℃, then adding 0.035mol of Br2, and after the dropwise adding is finished, heating to room temperature again. After 5h, the reaction of the raw materials is detected to be finished, 250ml of water is dripped into the reaction liquid, the organic phase obtained by extraction is dried by spinning, and the intermediate 1-1-3 is obtained by column chromatography (yield is 48%).
Synthesis of Compound 1-1: dissolving 0.017mol of intermediate 1-3 in 80ml of toluene solvent, sequentially adding 0.017mol of carbazole, 0.0425mol of sodium tert-butoxide, 0.00017mol of tri-tert-butylphosphine and 0.00017mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring, heating to reflux reaction, detecting that the reaction of the raw materials is finished after 4 hours, performing reduced pressure spin drying on reaction liquid, and performing column chromatography to obtain 0.012mol of compound 1-1 (yield 70%).
Calcd for C37H21N 3O: 523.58 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.81 (2H, m), 7.25-7.33 (7H, m), 7.48-7.49 (4H, m), 7.63-7.67 (2H, m), 7.89-7.94 (2H, m), 8.12-8.13 (1H, m), 8.51-8.55 (3H, m).
Preparation example 2: preparation of Compounds 1-6
Synthesis of intermediate 1-6-1: adding 165ml of dioxane solvent and 5ml of water into a three-necked bottle, sequentially adding 0.1mol of 3-boracic acid benzofuran, 0.1mol of 1-bromo-3-chloro-2-iodobenzene, 0.25mol of potassium carbonate and 0.001mol of ferrocene palladium dichloride, stirring and heating to reflux, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying reaction liquid, and carrying out column chromatography to obtain an intermediate 1-6-1 (the yield is 71%).
Synthesis of intermediates 1-6-2: 0.071mol of intermediate 1-6-1 was dissolved in 200ml of tetrahydrofuran in a three-necked flask, the temperature was reduced to-78 ℃, then 40ml of n-BuLi (2.5M) was added dropwise thereto, after 30 minutes, 0.071mol of 4, 5-diazafluoren-9-one was placed therein, the temperature was raised to room temperature, and then the resulting mixture was stirred for 1 hour. After 200ml of HCl (1N) was added thereto and the resulting mixture was stirred for 30 minutes, the layers were separated to remove the solvent, and then the residue was recrystallized from ethyl acetate to obtain intermediate 1-6-2 (yield 50%).
Synthesis of Compounds 1-6: dissolving 0.017mol of intermediate 6-2 in 80ml of toluene solvent, sequentially adding 0.017mol of carbazole, 0.0425mol of sodium tert-butoxide, 0.00017mol of tri-tert-butylphosphine and 0.00017mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring, heating to reflux reaction, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying reaction liquid, and obtaining the compound 1-6 (yield is 70%) through column chromatography.
Calcd for C37H21N 3O: 523.58 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.81 (2H, m), 7.20-7.48 (10H, m), 7.63-7.66 (2H, m), 7.89-7.97 (3H, m), 8.12-8.12 (1H, m), 8.51-8.55 (3H, m).
Preparation example 3: preparation of Compounds 1-17
Synthesis of intermediate 1-17-1: dissolving 0.01mol of 2-bromocarbazole in 20ml of dioxane solvent, sequentially adding 0.01mol of 9-phenylcarbazole-3-boric acid, 0.025mol of potassium acetate and 0.0001mol of 1, 1' -bis (diphenylphosphino) ferrocene palladium dichloride under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, carrying out decompression and spin drying on reaction liquid, and carrying out column chromatography to obtain an intermediate 1-17-1 (yield is 80%).
Synthesis of Compounds 1-17: synthesis method Synthesis of Compound 1-1 gave Compound 1-17 (yield 70%).
Calcd for C55H32N 4O: 764.87 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta 7.00-7.60 (28H, m), 7.77-7.78 (2H, m), 8.57-8.58 (2H, m).
Preparation example 4: preparation of Compounds 1-22
Synthesis of intermediate 1-22-1: adding 165ml of dioxane solvent and 5ml of water into a three-necked flask, sequentially adding 0.1mol of 3-boracic acid benzofuran, 0.1mol of 2-bromo-4-chloro-1 iodobenzene, 0.25mol of potassium carbonate and 0.001mol of ferrocene palladium dichloride, stirring and heating to reflux, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying reaction liquid, and performing column chromatography to obtain the compound 1-22-1 (the yield is 75%).
Synthesis of intermediates 1-22-2: 0.075mol of intermediate 1-22-1 is dissolved in 200ml of tetrahydrofuran in a three-necked flask, the temperature is reduced to-78 ℃ and then 40ml of n-BuLi (2.5M) are added dropwise thereto, after 30 minutes 0.075mol of 4, 5-dinitrofluorene-9-one is added thereto, the temperature is raised to room temperature and the mixture is stirred for 1 hour. After 200ml of HCl (1N) was added thereto and the resulting mixture was stirred for 30 minutes, the layers were separated to remove the solvent, and then the residue was recrystallized from ethyl acetate to give intermediate 1-22-2 (yield 53%).
Synthesis of Compounds 1-22: dissolving 0.04mol of intermediate 1-22-2 in 80ml of toluene solvent, sequentially adding 0.04mol of 11H-benzocarbazole, 0.1mol of sodium tert-butoxide, 0.004mol of tri-tert-butylphosphine and 0.004mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-22 (yield is 62.5%).
Calcd for C41H23N 3O: 573.64 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.81 (2H, m), 7.25-7.38 (4H, m), 7.48-7.67 (9H, m), 7.89-7.94 (2H, m), 8.12-8.16 (2H, m), 8.51-8.55 (4H, m).
Preparation example 5: preparation of Compounds 1-31
Synthesis of Compounds 1-31: dissolving 0.01mol of intermediate 1-1-3 in 70ml of toluene solvent, sequentially adding 0.01mol of phenothiazine, 0.025mol of sodium tert-butoxide, 0.0001mol of tri-tert-butylphosphine and 0.0001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying the reaction liquid, and obtaining the compound 1-31 (yield is 68%) by column chromatography.
Calcd for C37H21N3 OS: 555.65 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.4-6.41 (1H, m), 6.68-6.75 (4H, m), 6.8-7.13 (11H, m), 7.36-7.37 (1H, m), 7.60-7.61 (2H, m), 8.57-8.58 (2H, m).
Preparation example 6: preparation of Compounds 1-39
Synthesis of Compounds 1-39: dissolving 0.017mol of intermediate 1-1-3 in 80ml of toluene solvent, sequentially adding 0.017mol of 11-phenyl-11, 12-indolino [2,3-a ] carbazole, 0.0425mol of sodium tert-butoxide, 0.00017mol of tri-tert-butylphosphine and 0.00017mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-39 (yield is 70%).
Calcd for C49H28N 4O: 688.77 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.81 (2H, m), 7.25-7.33 (8H, m), 7.45-7.67 (10H, m), 7.89-7.94 (3H, m), 8.12-8.12 (1H, d), 8.51-8.55 (4H, m).
Preparation example 7: preparation of Compounds 1-42
Synthesis of intermediate 1-42-1: adding 165ml of dioxane solvent and 5ml of water into a three-necked bottle, sequentially adding 0.1mol of 3-boracic acid benzofuran, 0.01mol of 1-bromo-3-chloro-2-iodobenzene, 0.025mol of potassium carbonate and 0.0001mol of ferrocene palladium dichloride, stirring and heating to reflux, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying reaction liquid, and carrying out column chromatography to obtain an intermediate 1-42-1 (the yield is 71%).
Synthesis of intermediates 1-42-2: 0.071mol of intermediate 1-42-1 was dissolved in 200ml of tetrahydrofuran in a three-necked flask, the temperature was reduced to-78 ℃, then 40ml of n-BuLi (2.5M) was added dropwise thereto, after 30 minutes, 0.071mol of 4, 5-diazafluoren-9-one was placed therein, the temperature was raised to room temperature, and then the resulting mixture was stirred for 1 hour. After 200ml of HCl (1N) was added thereto and the resulting mixture was stirred for 30 minutes, the layers were separated to remove the solvent, and then the residue was recrystallized from ethyl acetate to obtain intermediate 1-42-2 (yield 50%).
Synthesis of Compounds 1-42: dissolving 0.017mol of intermediate 1-42-2 in 80ml of toluene solvent, sequentially adding 0.017mol of 11-phenyl-11, 12-indoline [2,3-a ] carbazole, 0.0425mol of sodium tert-butoxide, 0.00017mol of tri-tert-butylphosphine and 0.00017mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4h, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-42 (yield is 70%).
Calcd for C49H28N 4O: 688.77 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.81 (2H, m), 7.25-7.66 (18H, m), 7.89-7.94 (3H, m), 8.12-8.12 (1H, d), 8.51-8.55 (4H, m).
Preparation example 8: preparation of Compounds 1-46
Synthesis of Compounds 1-46: dissolving 0.017mol of intermediate 1-1-3 in 80ml of toluene solvent, sequentially adding 0.017mol of 5-phenyl-5, 12-indoline [3,2-a ] carbazole, 0.0425mol of sodium tert-butoxide, 0.00017mol of tri-tert-butylphosphine and 0.00017mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain 0.012mol of compound 1-46 (yield 70%).
Calcd for C49H28N 4O: 688.77 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.81 (2H, m), 7.23-7.33 (9H, m), 7.45-7.67 (9H, m), 7.89-7.94 (3H, m), 8.12-8.12 (1H, d), 8.51-8.55 (4H, m).
Preparation example 9: preparation of Compounds 1-47
Synthesis of intermediate 1-47-1: adding 165ml of dioxane solvent and 5ml of water into a three-necked bottle, sequentially adding 0.1mol of 3-boracic acid benzofuran, 0.01mol of 1-bromo-3-chloro-2-iodobenzene, 0.025mol of potassium carbonate and 0.0001mol of ferrocene palladium dichloride, stirring and heating to reflux, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying reaction liquid, and carrying out column chromatography to obtain an intermediate 1-47-1 (the yield is 71%).
Synthesis of intermediates 1-47-2: 0.071mol of intermediate 1-47-1 was dissolved in 200ml of tetrahydrofuran in a three-necked flask, the temperature was reduced to-78 ℃, then 40ml of n-BuLi (2.5M) was added dropwise thereto, after 30 minutes, 0.071mol of 4, 5-diazafluoren-9-one was placed therein, the temperature was raised to room temperature, and then the resulting mixture was stirred for 1 hour. After 200ml of HCl (1N) was added thereto and the resulting mixture was stirred for 30 minutes, the layers were separated to remove the solvent, and then the residue was recrystallized from ethyl acetate to obtain intermediate 1-47-2 (yield 50%).
Synthesis of Compounds 1-47: dissolving 0.017mol of intermediate 1-47-2 in 80ml of toluene solvent, sequentially adding 0.017mol of 12-phenyl-5, 12-indoline [3,2-a ] carbazole, 0.0425mol of sodium tert-butoxide, 0.00017mol of tri-tert-butylphosphine and 0.00017mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4h, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-47 (yield is 70%).
Calculated value C49H28N4O：688.77±1。1H-NMR(400MHz，CDCl3)(ppm)δ＝6.81～6.81(2H，m)，7.23～7.66(18H，m)，7.89～7.94(3H，m)，8.12～8.12(1H，d)，8.51～8.55(4H，m)。
Preparation example 10: preparation of Compounds 1-50
Synthesis of intermediates 1-50-1: adding 165ml of dioxane solvent and 5ml of water into a three-necked bottle, sequentially adding 0.1mol of 3-boracic acid benzofuran, 0.01mol of o-bromoiodobenzene, 0.025mol of potassium carbonate and 0.0001mol of ferrocene palladium dichloride, stirring, heating to reflux, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying reaction liquid, and carrying out column chromatography to obtain an intermediate 1-50-1 (the yield is 71%).
Synthesis of intermediates 1-50-2: 0.071mol of intermediate 1-50-1 was dissolved in 200ml of tetrahydrofuran in a three-necked flask, the temperature was reduced to-78 ℃, then 40ml of n-BuLi (2.5M) was added dropwise thereto, after 30 minutes, 0.071mol of 4, 5-diazafluoren-9-one was placed therein, the temperature was raised to room temperature, and then the resulting mixture was stirred for 1 hour. After 200ml of HCl (1N) was put thereto and the resulting mixture was stirred for 30 minutes, the layers were separated to remove the solvent, and then the residue was recrystallized from ethyl acetate to obtain intermediate 1-50-2 (yield 50%).
Synthesis of intermediates 1-50-3: adding 0.035mol of intermediate 1-50-2 into 130ml of THF, stirring, cooling to-78 deg.C, then adding 40ml of n-BuLi (2.5M) dropwise, keeping the temperature for 30 minutes, then heating to room temperature, then keeping the temperature for 2 hours at room temperature, cooling to-78 deg.C, then adding 0.035mol of Br2, and heating to room temperature again after the completion of the dropwise addition. After 5h, the reaction of the raw materials is detected to be finished, 250ml of water is added into the reaction liquid dropwise, a large amount of solid is separated out, the mixture is stirred for half an hour and filtered, and the residue is subjected to column chromatography to obtain an intermediate 1-50-3 (the yield is 48%).
Synthesis of Compounds 1-50: dissolving 0.017mol of intermediate 1-50-3 in 80ml of toluene solvent, sequentially adding 0.017mol of 8H- [1] benzothieno [2,3-c ] carbazole, 0.0425mol of sodium tert-butoxide, 0.00017mol of tri-tert-butylphosphine and 0.00017mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-50 (yield is 70%).
Calculated value C43H23N3OS：629.73±1。1H-NMR(400MHz，CDCl3)(ppm)δ＝6.81～6.81(2H，m)，7.25～7.33(6H，m)，7.44～7.67(6H，m)，7.73～7.98(5H，m)，8.51～8.55(4H，m)。
Preparation example 11: preparation of Compounds 1-56
Synthesis of intermediates 1 to 56: adding 165ml of dioxane solvent and 5ml of water into a three-necked bottle, sequentially adding 0.1mol of 3-boracic acid benzofuran, 0.01mol of o-bromoiodobenzene, 0.025mol of potassium carbonate and 0.0001mol of ferrocene palladium dichloride, stirring, heating to reflux, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying reaction liquid, and carrying out column chromatography to obtain the intermediate 1-56 (the yield is 71%).
Synthesis of intermediates 1-56-2: 0.071mol of intermediate 1-56-1 was dissolved in 200ml of tetrahydrofuran in a three-necked flask, the temperature was reduced to-78 ℃, then 40ml of n-BuLi (2.5M) was added dropwise thereto, after 30 minutes, 0.071mol of 4, 5-diazafluoren-9-one was placed therein, the temperature was raised to room temperature, and then the resulting mixture was stirred for 1 hour. After 200ml of HCl (1N) was put thereto and the resulting mixture was stirred for 30 minutes, the layers were separated to remove the solvent, and then the residue was recrystallized from ethyl acetate to obtain intermediate 1-56-2 (yield 50%).
Synthesis of intermediates 1-56-3: adding 0.035mol of intermediate 1-56-2 into 130ml of THF, stirring, cooling to-78 deg.C, then adding 40ml of n-BuLi (2.5M) dropwise, keeping the temperature for 30 minutes, then heating to room temperature, then keeping the temperature for 2 hours at room temperature, cooling to-78 deg.C, then adding 0.035mol of Br2, and heating to room temperature again after the completion of the dropwise addition. After 5h, the reaction of the raw materials is detected to be finished, 250ml of water is added into the reaction liquid dropwise, a large amount of solid is separated out, the mixture is stirred for half an hour and filtered, and the residue is subjected to column chromatography to obtain the intermediate 1-56-3 (the yield is 8%).
Synthesis of Compounds 1-56: dissolving 0.017mol of intermediate 1-56-3 in 80ml of toluene solvent, sequentially adding 0.017mol of 5H- [1] benzothieno [3,2-c ] carbazole, 0.0425mol of sodium tert-butoxide, 0.00017mol of tri-tert-butylphosphine and 0.00017mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-56 (yield is 70%).
Calcd for C43H23N3 OS: 629.73 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.03-7.13 (8H, m), 7.31-7.60 (10H, m), 7.78-7.86 (3H, m), 8.57-8.58 (2H, m).
Preparation example 12: preparation of Compounds 1-61
Synthesis of Compounds 1-61: dissolving 0.017mol of intermediate 117-3 in 80ml of toluene solvent, sequentially adding 0.017mol of 5H- [1] benzofuro [3,2-c ] carbazole, 0.0425mol of sodium tert-butoxide, 0.00017mol of tri-tert-butylphosphine and 0.00017mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4H, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-61 (the yield is 70%).
Calcd for C43H23N3O 2: 613.66 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta 7.03-7.20 (12H, m), 7.36-7.60 (9H, m), 8.57-8.58 (2H, m).
Preparation example 13: preparation of Compounds 1-65
Synthesis of Compounds 1-65: dissolving 0.01mol of intermediate 1-1-3 in 70ml of toluene solvent, sequentially adding 0.01mol of 5, 7-dihydro-7, 7-dimethyl-indeno [2,1-b ] carbazole, 0.025mol of sodium tert-butoxide, 0.0001mol of tri-tert-butylphosphine and 0.0001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-65 (yield is 68%).
Calcd for C46H29N 3O: 639.74 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.67-1.68 (6H, d), 7.00-7.24 (10H, m) 7.36-7.61 (9H, m), 7.69-7.69 (1H, s), 8.06-8.07 (1H, m), 8.57-8.58 (2H, m).
Preparation example 14: preparation of Compounds 2-73
Synthesis of intermediate 2-73-1: preparing a Grignard reagent, adding 0.01mol of 3,3 '-2, 2' -bipyridine and 0.4mol of magnesium into 30ml of tetrahydrofuran, heating until a reflux reaction is initiated, slowly dropping the residual 0.09mol of 3,3 '-2, 2' -bipyridine tetrahydrofuran saturated solution, preserving heat and refluxing for about 1h, and keeping under nitrogen protection for later use. Adding 0.1mol of silicon tetrachloride and tetrahydrofuran into another three-necked bottle, uniformly stirring, carrying out nitrogen protection, cooling to-5 ℃, transferring the prepared Grignard reagent into a dropping funnel, slowly dropwise adding, keeping the temperature of the system not to exceed 10 ℃, stirring for 30min after dropwise adding, slowly raising the temperature to room temperature, detecting that the reaction of the raw materials is finished after 5h, dropwise adding a saturated ammonium chloride aqueous solution into the reaction solution, stirring for 5min, adding dichloromethane for extraction, taking organic phase, carrying out vacuum spin drying, and carrying out column chromatography on the residue to obtain an intermediate 2-73-1 (the yield is 40%).
Synthesis of intermediate 2-73-2: adding 0.1mol of 6-methoxybenzothiophene into 170ml of dichloromethane, stirring, and dropwise adding 0.1mol of Br2After the dropwise addition, the solution was heated to reflux. Detecting that the reaction of the raw materials is finished after 5h, dropwise adding 500ml of water into the reaction solution to separate out a large amount of solid, stirring for half an hour, filtering to obtain a residue, and performing column chromatography to obtain the final productIntermediate 2-73-2 (yield 62%).
Synthesis of intermediates 2-73-3: grignard reagent was prepared and synthesized by the same method as that for the intermediate 2-73-1 to obtain the intermediate 2-73-3 (yield 40%).
Synthesis of intermediates 2-73-4: grignard reagent was prepared and synthesized by the same method as that for the intermediate 2-73-1 to obtain the intermediate 2-73-4 (yield 40%).
Synthesis of intermediates 2-73-5: 0.01mol of intermediate 2-73-4 is dissolved in 50ml of dichloromethane, 0.01mol of boron tribromide is reacted for 2h at room temperature, organic phase is taken out, spinning-dried under reduced pressure, and the residue is subjected to column chromatography to obtain intermediate 2-73-5 (yield 70%).
Synthesis of intermediates 2-73-6: 0.007mol of the intermediate 2-73-5 is dissolved in 30ml of dichloromethane, trifluoromethanesulfonic anhydride is added dropwise, the mixture is reacted for 5 hours at room temperature, the organic phase is removed and dried by spinning under reduced pressure, and the residue is subjected to column chromatography to obtain the intermediate 2-73-6 (yield is 90%).
Synthesis of Compounds 2-73: dissolving 0.0063mol of intermediate 2-73-6 in 30ml of toluene solvent, sequentially adding 0.0063mol of carbazole, 0.016mol of sodium tert-butoxide, 0.000063mol of tri-tert-butylphosphine and 0.000063mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring, heating to reflux reaction, detecting that the reaction of the raw materials is finished after 4h, decompressing and spin-drying the reaction liquid, and performing column chromatography to obtain the compound 2-73 (yield 80%).
Calcd for C36H21N3 SSi: 555.72 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.23-7.33 (7H, m), 7.49-7.51 (3H, m), 7.63-7.64 (1H, m), 7.79-7.80 (1H, m), 7.94-7.95 (3H, m), 8.02-8.12 (3H, m), 8.55-8.63 (3H, m).
Example 1: preparation of organic light emitting device
After ultrasonically washing a glass substrate having an Indium Tin Oxide (ITO) electrode (first electrode, anode) with a thickness of about 1500 angstroms with distilled water and methanol in sequence, the washed glass substrate was dried, moved to a plasma cleaning system, and then cleaned using an oxygen plasma for about 5 minutes. The glass substrate is then loaded into a vacuum deposition apparatus.
Vacuum depositing HAT-CN onto the ITO electrode of the glass substrate to form a HIL having a thickness of about 100 angstroms; vacuum deposition of TAPC onto the hole injection layer formed an HTL having a thickness of about 400 angstroms.
Compound 1-1 was deposited on the hole transport region to form an EML having a thickness of about 300 angstroms.
TPBi is then vacuum deposited on the EML to form an ETL having a thickness of about 300 angstroms. Then, LiF was deposited on the ETL to form an EIL having a thickness of about 5 angstroms, and Al was deposited on the EIL to a thickness of about 1000 angstroms to form a second electrode (cathode), thereby completing the fabrication of the organic light emitting device.
Other embodiments
Organic light-emitting devices of the remaining examples were prepared in a similar manner to example 1, except that the compounds shown in table 1 were used instead of compound 1-1 in example 1.
Comparative example 1
An organic light-emitting device was produced in a similar manner to that in example 1, except that compound BD-1 was used instead of compound 1-1 in example 1.
Comparative example 2
An organic light-emitting device was produced in a similar manner to that in example 1, except that the compound BD-2 was used instead of the compound 1-1 in example 1.
Evaluation: evaluation of characteristics of organic light-emitting device
The driving voltage, emission efficiency and lifetime of the organic light emitting devices in examples and comparative examples were measured using a current-voltage source meter (Keithley 2400) and a Minolta CS-1000A spectroradiometer. The results are shown in table 1 below.
(1) Measurement of current density change with respect to voltage change
A current value flowing through each of the organic light emitting devices was measured while increasing a voltage from 0 volt (V) to about 10V by using a current-voltage source meter (Keithley 2400), and then divided by an area of the corresponding light emitting device to obtain a current density.
(2) Measurement of brightness variation with respect to voltage variation
The brightness of the organic light emitting device was measured while increasing the voltage from about 0V to about 10V by using a Minolta CS-1000A spectroradiometer.
(3) Measurement of emission efficiency
The organic light emitting device was calculated at 20 milliamperes per square centimeter (mA/cm) based on the current density, voltage, and luminance obtained from the measurements (1) and (2) described above2) Current efficiency at a certain current density.
(4) Measurement of lifetime
Hold 5000cd/m2Luminance (cd/m)2) And the time for the current efficiency (cd/A) to decrease to 50% was measured.
TABLE 1
| Luminescent layer | Drive voltage (V) | Efficiency (cd/A) | Half life (hrs) | |
| Example 1 | 1-1 | 3.65 | 4.64 | 470 |
| Example 2 | 1-6 | 3.62 | 4.69 | 471 |
| Example 3 | 1-17 | 3.38 | 4.99 | 491 |
| Example 4 | 1-22 | 3.47 | 4.88 | 481 |
| Example 5 | 1-31 | 3.32 | 5.03 | 497 |
| Example 6 | 1-39 | 3.59 | 4.71 | 472 |
| Example 7 | 1-42 | 3.58 | 4.78 | 475 |
| Example 8 | 1-46 | 3.39 | 4.95 | 487 |
| Example 9 | 1-47 | 3.45 | 4.91 | 482 |
| Example 10 | 1-50 | 3.51 | 4.83 | 478 |
| Example 11 | 1-56 | 3.54 | 4.79 | 476 |
| Example 12 | 1-61 | 3.63 | 4.74 | 473 |
| Example 13 | 1-65 | 3.48 | 4.87 | 479 |
| Example 14 | 1-2 | 3.42 | 4.93 | 484 |
| Example 15 | 1-85 | 3.52 | 4.81 | 477 |
| Example 16 | 1-101 | 3.66 | 4.65 | 466 |
| Example 17 | 2-26 | 3.65 | 4.75 | 473 |
| Example 18 | 2-53 | 3.47 | 4.89 | 479 |
| Example 19 | 2-73 | 3.72 | 4.57 | 462 |
| Example 20 | 2-85 | 3.53 | 4.73 | 482 |
| Comparative example 1 | BD-1 | 4.32 | 3.46 | 337 |
| Comparative example 2 | BD-2 | 4.58 | 3.24 | 328 |
As can be seen from the experimental results shown in table 1, the organic electroluminescent device formed by the compound of the present invention has a low driving voltage and a significantly higher lifetime and luminous efficiency than the prior art.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (20)
1. An organic electroluminescent compound having a structure represented by formula (I),
in the structure shown in the formula (I),
x is O or S;
z is Si or C;
Y1、Y2、Y3、Y4、Y5、Y6、Y7and Y8Each independently selected from CH and N, and wherein two non-adjacent N atoms must be present;
R1and R2Each independently selected from at least one of H, nitrogen-containing aromatic heterocyclic tricyclic group, nitrogen-containing aromatic heterocyclic tetracyclic group, nitrogen-containing aromatic heterocyclic pentacyclic group, substituted or unsubstituted diphenylamine group and substituted phenyl;
wherein the substituents optionally present in the substituted or unsubstituted diphenylamino group and the substituted phenyl group are each independently selected from C1-4At least one of an alkyl group, a phenyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a carbazolyl group, a dianilino group, and a phenyl-substituted carbazolyl group of (a);
wherein the nitrogen-containing aromatic heterocyclic tricyclic in the nitrogen-containing aromatic heterocyclic tricyclic group is a tricyclic shown in a formula (a1) or a formula (a2), and any position in the tricyclic shown in the formula (a1) and the formula (a2) which can be connected in a bonding manner is connected with the mother nucleus in the formula (I) through a C-C bond or a C-N bond;
wherein Y in formula (a2) is CH or N when used as the connecting site of the group; when Y is not the attachment site of the group, it is O, S, CH2Or NH;
and the H atom linked to the C atom and/or N atom in the tricyclic ring of formula (a1) and formula (a2) is optionally substituted by a group selected from C1-4Substituted with at least one group selected from the group consisting of alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, dianilinyl, and phenyl-substituted carbazolyl;
wherein the nitrogen-containing aromatic heterocyclic ring in the nitrogen-containing aromatic heterocyclic ring group is selected from tetracyclic rings shown in a formula (b1) and/or a formula (b2),
and formulae (b1) andthe H atom attached to the C atom in the tetracyclic ring of formula (b2) is optionally substituted by a group selected from C1-4Substituted with at least one of alkyl, phenyl and biphenyl groups;
wherein the nitrogen-containing aromatic heterocyclic pentacyclic ring in the nitrogen-containing aromatic heterocyclic pentacyclic group is selected from pentacycles shown in formulas (c1) to (c12),
and X in the formulae (c1) to (c12)1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11And X12Each independently selected from O, S, CH2And NH;
and the H atom connected to the C atom and/or the N atom in the pentacyclic ring of formulae (C1) to (C12) is optionally substituted by a group selected from C1-4At least one of alkyl and phenyl of (a);
2. the compound of claim 1, wherein the structure of formula (I) is at least one of the following structures of formulae (I1) to (I5):
and, in the structures represented by the formulae (I1) to (I5), R1、R2X and Z are correspondingly as defined in claim 1.
3. The compound of claim 1, wherein the structure of formula (I) is a compound of formula (I1):
and, in the structure represented by the formula (I1), R1、R2X and Z are correspondingly as defined in claim 1.
4. The compound of claim 1, wherein the structure of formula (I) is any one of the following compounds:
5. the compound of claim 1, wherein the structure of formula (I) is a compound of formula (I2):
and, a junction represented by the formula (I2)In the structure of, R1、R2X and Z are correspondingly as defined in claim 1.
6. The compound of claim 1, wherein the structure of formula (I) is any one of the following compounds:
7. the compound of claim 1, wherein the structure of formula (I) is a compound of formula (I3):
and, in the structure represented by the formula (I3), R1、R2X and Z are correspondingly as defined in claim 1.
8. The compound of claim 1, wherein the structure of formula (I) is any one of the following compounds:
9. the compound of claim 1, wherein the structure of formula (I) is a compound of formula (I4):
and, in the structure represented by the formula (I4), R1、R2X and Z are correspondingly as defined in claim 1.
10. The compound of claim 1, wherein the structure of formula (I) is any one of the following compounds:
11. the compound of claim 1, wherein the structure of formula (I) is a compound of formula (I5):
and, in the structure represented by the formula (I5), R1、R2X and Z are correspondingly as defined in claim 1.
12. The compound of claim 1, wherein the structure of formula (I) is any one of the following compounds:
13. the compound of claim 1, wherein the structure of formula (I) is any one of the following specific compounds:
14. the compound of claim 1, wherein the structure of formula (I) is any one of the following specific compounds:
15. use of the organic electroluminescent compounds as claimed in any of claims 1 to 14 in organic electroluminescent devices.
16. An organic electroluminescent device comprising one or more compounds of the organic electroluminescent compounds as claimed in any one of claims 1 to 14.
17. The organic electroluminescent device according to claim 16, wherein the organic electroluminescent compound is present in at least one of an electron transport layer, a light emitting layer and a hole blocking layer of the organic electroluminescent device.
18. The organic electroluminescent device according to claim 17, wherein the organic electroluminescent compound is present in a light-emitting layer of the organic electroluminescent device.
19. The organic electroluminescent device according to claim 17, wherein the organic electroluminescent compound serves as the light-emitting layer.
20. The organic electroluminescent device according to any one of claims 16 to 19, wherein the organic electroluminescent device comprises a substrate, an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer and a cathode, which are sequentially stacked.
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| CN112645960B (en) * | 2020-12-22 | 2022-03-15 | 吉林奥来德光电材料股份有限公司 | Electron transport material, preparation method thereof and organic electroluminescent device |
| CN112812123B (en) * | 2020-12-30 | 2023-12-01 | 吉林奥来德光电材料股份有限公司 | Hole compound, preparation method thereof and organic electroluminescent device |
| CN115490624A (en) * | 2021-06-18 | 2022-12-20 | 北京绿人科技有限责任公司 | Organic compound containing azetidine and organic electroluminescent device |
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| CN107614493A (en) * | 2015-10-06 | 2018-01-19 | 株式会社Lg化学 | Spiro-compound and the organic luminescent device for including it |
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