CN115974805A - Anthracene compound - Google Patents
Anthracene compound Download PDFInfo
- Publication number
- CN115974805A CN115974805A CN202111188684.9A CN202111188684A CN115974805A CN 115974805 A CN115974805 A CN 115974805A CN 202111188684 A CN202111188684 A CN 202111188684A CN 115974805 A CN115974805 A CN 115974805A
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- CN
- China
- Prior art keywords
- reaction
- added
- water
- organic electroluminescent
- compound
- Prior art date
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- -1 Anthracene compound Chemical class 0.000 title claims description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title description 6
- 239000000463 material Substances 0.000 claims abstract description 81
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 36
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 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 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005556 thienylene group Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 239000007787 solid Substances 0.000 abstract description 44
- 238000002347 injection Methods 0.000 abstract description 36
- 239000007924 injection Substances 0.000 abstract description 36
- 230000002349 favourable effect Effects 0.000 abstract description 4
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 97
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 54
- 229910000027 potassium carbonate Inorganic materials 0.000 description 27
- 239000000843 powder Substances 0.000 description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
- 238000001704 evaporation Methods 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 19
- 230000005525 hole transport Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 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 18
- 239000000243 solution Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- 239000002019 doping agent Substances 0.000 description 15
- BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 238000002386 leaching Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000010907 mechanical stirring Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- RSGRRCWDCXLEHS-UHFFFAOYSA-N 1-bromo-3-chloro-5-iodobenzene Chemical compound ClC1=CC(Br)=CC(I)=C1 RSGRRCWDCXLEHS-UHFFFAOYSA-N 0.000 description 2
- JOXBFDPBVQGJOJ-UHFFFAOYSA-N 2,5-dichloro-1,3-benzoxazole Chemical compound ClC1=CC=C2OC(Cl)=NC2=C1 JOXBFDPBVQGJOJ-UHFFFAOYSA-N 0.000 description 2
- BPRGLVVFWRNXEP-UHFFFAOYSA-N 2,6-dibromoanthracene Chemical compound C1=C(Br)C=CC2=CC3=CC(Br)=CC=C3C=C21 BPRGLVVFWRNXEP-UHFFFAOYSA-N 0.000 description 2
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 2
- LLKRSJVPTKFSLS-UHFFFAOYSA-N 2-bromo-5-iodopyridine Chemical compound BrC1=CC=C(I)C=N1 LLKRSJVPTKFSLS-UHFFFAOYSA-N 0.000 description 2
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 2
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- VHHDLIWHHXBLBK-UHFFFAOYSA-N anthracen-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=C(C=CC=C3)C3=CC2=C1 VHHDLIWHHXBLBK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 1
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- WKHDVHMRMDBUMZ-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)-1,3-benzoxazole Chemical compound C1=CC=C2OC(C=3OC4=CC=CC=C4N=3)=NC2=C1 WKHDVHMRMDBUMZ-UHFFFAOYSA-N 0.000 description 1
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 1
- GPOMKCKAJSZACG-UHFFFAOYSA-N 2-phenylanthracene Chemical compound C1=CC=CC=C1C1=CC=C(C=C2C(C=CC=C2)=C2)C2=C1 GPOMKCKAJSZACG-UHFFFAOYSA-N 0.000 description 1
- VOIZNVUXCQLQHS-UHFFFAOYSA-N 3-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC(Br)=C1 VOIZNVUXCQLQHS-UHFFFAOYSA-N 0.000 description 1
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000007740 vapor deposition Methods 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
Images
Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
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Abstract
The present application provides a compound of formula (I) having high interatomic bond energy, good thermal stability, and favorable intermolecular solid state stacking, having an appropriate energy level between adjacent layers, and favorable exciton injection and transfer. When the organic electroluminescent material is used as an electron transport material, the driving voltage of an organic electroluminescent device can be effectively reduced, the luminous efficiency of the organic electroluminescent device is improved, and the service life of the organic electroluminescent device is prolonged. The present application also provides an organic electroluminescent device and a display device comprising the compound of formula (I).
Description
Technical Field
The application relates to the technical field of organic light-emitting display, in particular to an anthracene compound.
Background
Electroluminescence (EL) refers to a phenomenon in which a light-emitting material emits light when excited by current and voltage under the action of an electric field, and is a light-emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage dc driving, full curing, wide viewing angle, light weight, simple composition and process, etc., and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, and has a large viewing angle, low power, a response speed 1000 times that of the liquid crystal display, and a manufacturing cost lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
With the continuous advance of OLED technology in both lighting and display fields, people pay more attention to the research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.
Organic electroluminescent materials have many advantages over inorganic luminescent materials, such as: the processing performance is good, a film can be formed on any substrate by a vapor deposition or spin coating method, flexible display and large-area display can be realized, the optical performance, the electrical performance, the stability and the like of the material can be adjusted by changing the structure of molecules, and the selection of the material has a large space. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (including host materials and guest materials), and the like. At present, as an important functional material, an electron transport material has a direct influence on the mobility of electrons, and ultimately influences the luminous efficiency of an OLED. The problem of low mobility of the currently commercially available electron transport materials is an important limiting factor in the development of device performance, and more researches are worth to be made for developing materials with higher mobility.
Disclosure of Invention
An object of the present application is to provide an anthracene compound which, when used as an electron transport material, can realize an improvement in the operating efficiency and an extension in the service life of an organic electroluminescent device.
A first aspect of the present application provides a compound of formula (I):
wherein,
L 1 and L 2 Each independently selected from a bond, C unsubstituted or substituted by Rc 6 -C 30 Arylene, C unsubstituted or substituted by Rc 3 -C 30 A heteroarylene group;
R 1 -R 8 each independently selected from hydrogen, deuterium, C 1 -C 10 Alkyl, C unsubstituted or substituted by Rc 6 -C 30 Aryl, C unsubstituted or substituted by Rc 3 -C 30 Heteroaryl radical, R 1 -R 8 Wherein two adjacent groups can be connected to form a ring;
each X is independently selected from O or S;
Y 1 -Y 8 each independently selected from hydrogen, C unsubstituted or substituted by Rc 6 -C 30 Aryl, C unsubstituted or substituted by Rc 3 -C 30 Heteroaryl radical, Y 1 -Y 8 Wherein two adjacent groups can be connected to form a ring;
each heteroatom on the heteroaryl or heteroarylene is independently selected from O, S or N;
the substituents Rc of each group are each independently selected from deuterium, halogen, nitro, cyano, C 1 -C 4 Alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
A second aspect of the present application provides an electron transport material comprising at least one of the compounds provided in the first aspect of the present application.
In a third aspect, the present application provides an organic electroluminescent device comprising at least one of the electron transport materials provided in the second aspect of the present application.
A fourth aspect of the present application provides a display apparatus comprising the organic electroluminescent device provided in the third aspect of the present application.
The compound has a parent structure of anthracene bibenzoxazole, has high bond energy among atoms, has good thermal stability, is favorable for intermolecular solid-state accumulation, has a proper energy level with adjacent layers when used as an electron transport material, is favorable for exciton injection and migration, can effectively reduce driving voltage, has high electron transfer rate, and can realize good luminous efficiency and service life in an organic electroluminescent device. The compound has a large conjugated plane, is beneficial to molecular accumulation, shows good thermodynamic stability and shows long service life in a device. The organic electroluminescent device comprises the compound as an electron transport material, so that the driving voltage can be effectively reduced, the luminous efficiency can be improved, and the service life of the organic electroluminescent device can be prolonged. The display device provided by the application has an excellent display effect.
Of course, not all advantages described above need to be achieved at the same time in the practice of any one product or method of the present application.
Drawings
In order to more clearly illustrate the technical solutions in the present application or the prior art, the drawings needed for describing the embodiments or the prior art are briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present application, and other embodiments can be obtained by those skilled in the art according to the drawings.
Fig. 1 is a schematic view of a typical organic electroluminescent device.
Detailed Description
The technical solutions in the present application will be described clearly and completely with reference to the accompanying drawings in the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments obtained by a person of ordinary skill in the art based on the embodiments in the present application are within the scope of protection of the present application.
The present application provides in a first aspect a compound of formula (I):
wherein,
L 1 and L 2 Each independently selected from a bond, C unsubstituted or substituted by Rc 6 -C 30 Arylene, C unsubstituted or substituted by Rc 3 -C 30 A heteroarylene group;
R 1 -R 8 each independently selected from hydrogen, deuterium, C 1 -C 10 Alkyl, C unsubstituted or substituted by Rc 6 -C 30 Aryl, C unsubstituted or substituted by Rc 3 -C 30 Heteroaryl radical, R 1 -R 8 Wherein two adjacent groups can be connected to form a ring;
each X is independently selected from O or S;
Y 1 -Y 8 each independently selected from hydrogen, C unsubstituted or substituted by Rc 6 -C 30 Aryl, C unsubstituted or substituted by Rc 3 -C 30 Heteroaryl radical, Y 1 -Y 8 Wherein two adjacent groups can be connected to form a ring;
each heteroatom on the heteroaryl or the heteroarylene is independently selected from O, S or N;
the substituents Rc of each group are each independently selected from deuterium, halogen, nitro, cyano, C 1 -C 4 Alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
Preferably, L 1 And L 2 Each independently selected from a bond, C unsubstituted or substituted by Rc 6 -C 18 Arylene, C unsubstituted or substituted by Rc 3 -C 18 A heteroarylene group.
More preferably, said L 1 And L 2 Each independently selected from a bond, a subunit of the following compound unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene.
For example, the compound of formula (I) may be selected from the following compounds represented by A1 to a 25:
the compound of formula (I) provided by the application has high bond energy between atoms, has good thermal stability and is beneficial to solid-state accumulation between molecules. In addition, the preparation process of the compound of the formula (I) is simple and easy to implement, raw materials are easy to obtain, and the compound is suitable for industrial production.
A second aspect of the present application provides an electron transport material comprising at least one of the compounds provided in the first aspect of the present application.
When the compound is used as an electron transport material, the compound has a matched energy level with the adjacent layers, so that the injection and the migration of electrons are facilitated, and the driving voltage can be effectively reduced. Meanwhile, the organic electroluminescent device has higher electron transfer rate, and can realize good luminous efficiency and service life in the organic electroluminescent device. The organic electroluminescent material has a large conjugated plane, is beneficial to molecular accumulation, shows good thermodynamic stability, and can prolong the service life when being used in an organic electroluminescent device.
A third aspect of the present application provides an organic electroluminescent device comprising at least one of the electron transport materials provided in the second aspect of the present application. Therefore, the organic electroluminescent device provided by the application has low driving voltage, high luminous efficiency and long service life.
In the present application, there is no particular limitation on the kind and structure of the organic electroluminescent device, and there may be different types and structures of organic electroluminescent devices known in the art as long as the electron transport material provided herein can be used.
The organic electroluminescent device of the present application may be a light-emitting device having a top emission structure, and examples thereof include a light-emitting device comprising an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or translucent cathode in this order on a substrate.
The organic electroluminescent device of the present application may be a light-emitting device having a bottom emission structure, and may include a structure in which a transparent or translucent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially provided on a substrate.
The organic electroluminescent device of the present application may be a light-emitting device having a double-sided light-emitting structure, and may include a structure in which a transparent or translucent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or translucent cathode are sequentially provided on a substrate.
In addition, an electron blocking layer may be provided between the hole transport layer and the light emitting layer, a hole blocking layer may be provided between the light emitting layer and the electron transport layer, and a light extraction layer may be provided on the transparent electrode on the light outgoing side. However, the structure of the organic electroluminescent device of the present application is not limited to the above-described specific structure, and the above-described layers may be omitted or added if necessary. The thickness of each layer is not particularly limited as long as the object of the present invention can be achieved. For example, the organic electroluminescent device may include an anode made of metal, a hole injection layer (5 nm to 20 nm), a hole transport layer (80 nm to 140 nm), an electron blocking layer (5 nm to 20 nm), a light emitting layer (150 nm to 400 nm), a hole blocking layer (5 nm to 20 nm), an electron transport layer (300 nm to 800 nm), an electron injection layer (5 nm to 20 nm), a transparent or semitransparent cathode, and a light extraction layer (50 nm to 90 nm) in this order on a substrate.
Fig. 1 shows a schematic diagram of a typical organic electroluminescent device, in which a substrate 1, a reflective anode electrode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode electrode 8 are sequentially disposed from bottom to top.
It is to be understood that fig. 1 schematically illustrates the structure of a typical organic electroluminescent device, and the present application is not limited to this structure, and the electron transport material of the present application may be used in any type of organic electroluminescent device.
For convenience, the organic electroluminescent device of the present application is described below with reference to fig. 1, but this is not meant to limit the scope of the present application in any way. It is understood that all organic electroluminescent devices capable of using the electron transport materials of the present application are within the scope of the present application.
In the present application, the substrate 1 is not particularly limited, and conventional substrates used in organic electroluminescent devices in the related art, such as glass, polymer materials, and glass and polymer materials with Thin Film Transistor (TFT) components, etc., may be used.
In the present application, the reflective anode material 2 is not particularly limited, and may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) known in the art 2 ) The transparent conductive material such as zinc oxide (ZnO), may be selected from metal materials such as silver and its alloy, aluminum and its alloy, organic conductive materials such as poly-3,4-ethylenedioxythiophene (PEDOT), or the above materialsMultilayer structure of the material, etc.
In the present application, the material of the hole injection layer 3 is not particularly limited, and may be made of a hole injection layer material known in the art. For example, at least one of known Hole Transport Materials (HTM) is selected as the hole injection material.
In the present application, the hole injection layer 3 may further include a p-type dopant, the kind of which is not particularly limited, and various p-type dopants known in the art may be used. For example, the p-type dopant may be selected from, but is not limited to, at least one of the following p-1 to p-3 compounds:
in the present application, the amount of the p-type dopant is not particularly limited and may be an amount well known to those skilled in the art.
In the present application, the material of the hole transport layer 4 is not particularly limited, and may be made using a Hole Transport Material (HTM) known in the art. The number of layers of the hole transport layer 4 is not particularly limited, and may be adjusted as needed as long as it satisfies the object of the present application, for example, 1 layer, 2 layers, 3 layers, 4 layers, or more.
For example, the HTM for the hole injection layer material and the HTM for the hole transport layer material may be selected from, but not limited to, at least one of the following HT-1 to HT-31 compounds:
in the present application, the light emitting layer 5 may include a blue light emitting layer, a green light emitting layer, or a red light emitting layer, the light emitting material in the light emitting layer 5 is not particularly limited, and various light emitting materials known to those skilled in the art may be used, for example, the material of the light emitting layer 5 may include a host material and a guest material.
In the present application, the host material may be selected from, but is not limited to, at least one of the following BH-1 to BH-10 compounds:
in the present application, the guest material is not particularly limited, and at least one of light-emitting layer guest materials known in the art may be used. For example, the light-emitting layer guest material may be selected from, but is not limited to, at least one of the following BD-1 to BD-9 compounds:
in the present application, the amount of the guest material of the light-emitting layer is not particularly limited and may be an amount well known to those skilled in the art.
In the present application, the electron transport layer 6 comprises at least one of the electron transport materials of the present application, and the electron transport layer 6 may also comprise a combination of at least one of the electron transport materials of the present application and at least one of the known electron transport materials. The number of the electron transport layers 6 is not particularly limited, and may be adjusted according to actual needs as long as the object of the present application is satisfied, for example, 1, 2, 3,4 or more layers.
For example, known electron transport materials may be selected from, but are not limited to, at least one of the following ET-1 to ET-57 compounds:
in the present application, the electron transport layer 6 may further include an n-type dopant, the kind of the n-type dopant is not particularly limited, and various n-type dopants known in the art may be employed, for example, the following n-type dopants may be employed:
in the present application, the amount of the n-type dopant is not particularly limited and may be an amount well known to those skilled in the art.
In the present application, the material of the electron injection layer 7 is not particularly limited, and electron injection materials known in the art may be used, and for example, may include, but are not limited to, liQ, liF, naCl, csF, li in the prior art 2 O、Cs 2 CO 3 And at least one of BaO, na, li, ca and the like.
In the present application, the material of the cathode electrode 8 is not particularly limited, and may be selected from, but not limited to, magnesium silver mixture, metal such as LiF/Al, ITO, al, etc., metal mixture, oxide, etc.
A fourth aspect of the present application provides a display apparatus comprising the organic electroluminescent device provided in the third aspect of the present application. The display device includes, but is not limited to, a display, a television, a tablet computer, a mobile communication terminal, etc.
The method for preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art may be used, for example, the present application may be prepared by the following preparation method:
(1) Cleaning a reflective anode electrode 2 on an OLED device substrate 1 for top emission, respectively performing steps of medicine washing, water washing, hair brushing, high-pressure water washing, air knife and the like in a cleaning machine, and then performing heat treatment;
(2) Vacuum evaporating a hole injection material on the reflecting anode electrode 2 to form a hole injection layer 3;
(3) Vacuum evaporating a hole transport material on the hole injection layer 3 to form a hole transport layer 4;
(4) A luminescent layer 5 is evaporated on the hole transport layer 4 in vacuum, and the luminescent layer 5 comprises a host material and a guest material;
(5) Vacuum evaporating an electron transport material on the luminescent layer 5 to form an electron transport layer 6;
(6) Vacuum evaporating an electron injection material on the electron transport layer 6 to form an electron injection layer 7;
(7) A cathode material was vacuum-deposited on the electron injection layer 7 as a cathode electrode 8.
Only the structure of a typical organic electroluminescent device and a method for fabricating the same are described above, and it should be understood that the present application is not limited to this structure. The electron transport material of the present application can be used for an organic electroluminescent device of any structure, and the organic electroluminescent device can be manufactured by any manufacturing method known in the art.
The method for synthesizing the compound of the present application is not particularly limited, and the synthesis can be performed by any method known to those skilled in the art. The following illustrates the synthesis of the compounds of the present application.
Synthesis example 1 Synthesis of Compound A1:
to a reaction flask were added 100mmol of p-bromophenylboronic acid, 100mmol of 2-chlorobenzoxazole, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ) And reacting at 60 ℃ for 12h. Stopping reaction after reaction, cooling the reactant to room temperature, adding water, filtering, washing with water, and re-coagulating the obtained solid with tolueneThe crystals were purified to give white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the p-bromophenylboronic acid.
N 2 Under protection, adding M1 (250mmol, 2.5eq.) and tetrahydrofuran 1L into a 10L three-neck flask provided with a mechanical stirring and low-temperature thermometer, cooling to-90 ℃ to-80 ℃ by liquid nitrogen, dropwise adding n-butyl lithium (250mmol, 2.5eq.) and preserving heat (from-90 ℃ to-80 ℃) for 30min after the dropwise adding is finished, adding 9,10-dianthraquinone (100mmol, 1eq.) and naturally heating to zero after the addition is finished, and continuously stirring for 8 hours. After the reaction, 1000mL of 10wt% aqueous ammonium chloride solution was added, the solution was separated, the organic phase was washed with 300mL of 10wt% aqueous ammonium chloride solution each time, the filtrate was concentrated to obtain a black solid, and the black solid was crystallized from toluene to obtain a pale yellow sandy solid M2.
N 2 Adding acetic acid 1L into the reaction kettle under protection, stirring, heating, adding intermediate M1 100mmol, KI 300mmol and NaHPO into the reaction solution when the temperature of the reaction solution is raised to about 60 deg.C 2 ·H 2 O300 mmol, refluxing (about 120 ℃) to react for 5 hours, and stopping heating. And (3) cooling, carrying out suction filtration, sequentially leaching with acetic acid and absolute ethyl alcohol, draining, repeatedly leaching with water, finally leaching with acetone, and draining to obtain a yellow solid compound A1.
1 H NMR(400MHz,Chloroform)8.21(s,2H),7.96-7.74(m,8H),7.52(d,J＝10.0Hz,8H),7.43-7.25(m,6H).
Synthesis example 2 Synthesis of Compound A2:
into a reaction flask were charged 100mmol of 2-bromo-5-iodopyridine, 100mmol of pinacol diboron, 41.4g of potassium carbonate (300 mmol) and 800ml of toluene, and 1mol% of tris (dibenzylideneacetone) dipalladium (Pd) 2 (dba) 3 ) And reacting at 100 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized from toluene to purify it to obtain white powder M1. Wherein, pd 2 (dba) 3 Is added withThe amount of the added 2-bromo-5-iodopyridine is 1mol percent.
To a reaction flask was added 100mmol M1, 100mmol of 2-chlorobenzoxazole, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ) And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized and purified with toluene to obtain white powder M2. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M1.
N 2 Under protection, adding M2 (250mmol, 2.5eq.) and tetrahydrofuran 1L into a 10L three-neck flask provided with a mechanical stirring and low-temperature thermometer, cooling to-90 ℃ to-80 ℃ by liquid nitrogen, dropwise adding n-butyl lithium (250mmol, 2.5eq.) and preserving heat (from-90 ℃ to-80 ℃) for 30min after the dropwise adding is finished, adding 9,10-dianthraquinone (100mmol, 1eq.) and naturally heating to zero after the addition is finished, and continuously stirring for 8 hours. After the reaction, 1000mL of 10wt% aqueous ammonium chloride solution was added, the solution was separated, the organic phase was washed with 300mL of 10wt% aqueous ammonium chloride solution each time, the filtrate was concentrated to obtain a black solid, and the black solid was crystallized from toluene to obtain a pale yellow sandy solid M3.
N 2 Adding 1L of acetic acid into the reaction kettle under protection, stirring, heating, adding the intermediate M3 100mmol, KI 300mmol and NaHPO into the reaction solution when the temperature of the reaction solution is raised to about 60 DEG C 2 ·H 2 O300 mmol, refluxing (about 120 deg.C) and reacting for 5 hours, and stopping heating. And after cooling, carrying out suction filtration, sequentially eluting with acetic acid and absolute ethyl alcohol and pumping to dry, then repeatedly eluting with water, and finally eluting with acetone and pumping to dry to obtain a yellow solid compound A2.
1 H NMR(400MHz,Chloroform)9.11(s,2H),8.28(s,2H),8.19(d,J＝8.0Hz,4H),7.74(s,-7.53(m,8H),7.38-7.23(m,6H).
Synthesis example 3 Synthesis of Compound A3:
in a reaction flaskTo this was added 100mmol of p-bromobenzeneboronic acid, 100mmol of 2-chlorobenzothiazole, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ) And reacting for 12h at 60 ℃. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the p-bromophenylboronic acid.
N 2 Under protection, adding M1 (250mmol, 2.5eq.) and tetrahydrofuran 1L into a 10L three-neck flask provided with a mechanical stirring and low-temperature thermometer, cooling to-90 ℃ to-80 ℃ by liquid nitrogen, dropwise adding n-butyl lithium (250mmol, 2.5eq.) and preserving heat (from-90 ℃ to-80 ℃) for 30min after the dropwise adding is finished, adding 9,10-dianthraquinone (100mmol, 1eq.) and naturally heating to zero after the addition is finished, and continuously stirring for 8 hours. After the reaction, 1000mL of 10wt% ammonium chloride aqueous solution was added, the solution was separated, the organic phase was washed with 300mL of 10wt% ammonium chloride aqueous solution each time, the filtrate was concentrated to obtain a black solid, and the black solid was crystallized from toluene to obtain a pale yellow sandy solid M2.
N 2 Adding acetic acid 1L into the reaction kettle under protection, stirring, heating, adding intermediate M1 100mmol, KI 300mmol and NaHPO into the reaction solution when the temperature of the reaction solution is raised to about 60 deg.C 2 ·H 2 O300 mmol, refluxing (about 120 deg.C) and reacting for 5 hours, and stopping heating. And (3) cooling, carrying out suction filtration, sequentially leaching with acetic acid and absolute ethyl alcohol, draining, repeatedly leaching with water, finally leaching with acetone, and draining to obtain a yellow solid compound A3.
1 H NMR(400MHz,Chloroform)8.20(d,J＝12.0Hz,4H),8.04(t,J＝7.2Hz,4H),7.99(d,J＝10.0Hz,8H),7.52(d,J＝10.0Hz,4H),7.43-7.25(m,4H).
Synthesis example 4 Synthesis of Compound A4:
100mmol of 2-phenylanthracene and 500ml of dichloromethane are added into a single-mouth bottle, the temperature is reduced to 0 ℃, 200mmol of N-bromosuccinimide (NBS) is added in batches, the temperature is kept at 0 ℃ for 1h, the reaction is carried out for 3h, and the disappearance of the raw materials is monitored by Thin Layer Chromatography (TLC). Water is added into the reaction solution, ethyl acetate is used for extraction, and the organic phase is concentrated to obtain brown solid M1.
Into a reaction flask were charged 100mmol of M1, 200mmol of pinacol diboron, 41.4g of potassium carbonate (300 mmol) and 800ml of toluene, and 2mol% of tris (dibenzylideneacetone) dipalladium (Pd) 2 (dba) 3 ) And reacting at 100 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M2. Wherein, pd 2 (dba) 3 Is added in an amount of 2mol% based on M1.
Into a reaction flask were charged 100mmol of 2-chlorobenzoxazole, 100mmol of p-bromobenzoic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ) And reacting for 12h at 60 ℃. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M3. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the 2-chlorobenzoxazole.
Into a reaction flask were charged 100mmol of M2, 200mmol of M3, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% Pd (PPh) was added 3 ) 4 And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain compound A4 as a yellow powder. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 2mol% based on M2.
1 H NMR(400MHz,Chloroform)8.96(s,1H),8.34(s,1H),7.96-7.82(m,4H),7.74(d,J＝8.0Hz,4H),7.62-7.49(m,6H),7.39(d,J＝12.0Hz,6H),7.33-7.15(m,6H).
Synthesis example 5 Synthesis of Compound A5:
100mmol of 2,6-dibromoanthracene, 200mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water are added to a reaction flask, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) is added 3 ) 4 ) And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M1. Wherein, pd (PPh) 3 ) 4 The amount of (A) added was 1mol% of 2,6-dibromoanthracene.
Adding 100mmol of M1 and 500ml of dichloromethane into a single-mouth bottle, cooling to 0 ℃, adding 200mmol of N-bromosuccinimide (NBS) in batches, keeping the temperature at 0 ℃ for 1h, reacting for 3h, and monitoring the disappearance of the raw materials by thin-layer chromatography (TLC). Adding water into the reaction solution, extracting by ethyl acetate, and concentrating the organic phase to obtain brown solid M2.
Into a reaction flask were charged 100mmol of M2, 200mmol of pinacol diboron, 41.4g of potassium carbonate (300 mmol) and 800ml of toluene, and 2mol% of tris (dibenzylideneacetone) dipalladium (Pd) 2 (dba) 3 ) And reacting at 100 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M3. Wherein, pd 2 (dba) 3 Is added in an amount of 2mol% based on M2.
Into a reaction flask were charged 100mmol of 2-chlorobenzoxazole, 100mmol of p-bromobenzoic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) was added 3 ) 4 And reacting for 12h at 60 ℃. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder M4. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the 2-chlorobenzoxazole.
100mmol of M3 and 200mmol of M3 are added into a reaction flaskM4, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% Pd (PPh) are added 3 ) 4 And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized and purified with toluene to obtain compound A5 as a yellow powder. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 2mol% based on M2.
1 H NMR(400MHz,Chloroform)8.97(s,2H),8.35(s,2H),7.74(d,J＝8.0Hz,8H),7.50(d,J＝12.0Hz,6H),7.39(d,J＝10.0Hz,12H),7.25(s,2H).
Synthesis example 6 Synthesis of Compound A7:
to a reaction flask were added 100mmol of 2-chlorobenzoxazole, 100mmol of p-bromophenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ) And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized from toluene to purify it to obtain white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the 2-chlorobenzoxazole.
Into a reaction flask were charged 100mmol of M1, 100mmol of 9-anthraceneboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) was added 3 ) 4 And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized and purified with toluene to obtain white powder M2. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M1.
Adding 100mmol of M2 and 500ml of dichloromethane into a single-mouth bottle, cooling to 0 ℃, adding 200mmol of N-bromosuccinimide (NBS) in batches, keeping the temperature at 0 ℃ for 1h, reacting for 3h, and monitoring the disappearance of the raw materials by thin-layer chromatography (TLC). Adding water into the reaction solution, extracting by ethyl acetate, and concentrating the organic phase to obtain brown solid M3.
Into a reaction flask were added 100mmol of 2-chlorobenzoxazole, 100mmol of m-bromobenzoic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ) And reacting for 12h at 60 ℃. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder M4. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the 2-chlorobenzoxazole.
100mmol of M4, 100mmol of pinacol diborate, 29.4g of potassium carbonate (300 mmol), 800ml of dioxane and 1mol% of palladium acetate were charged in a reaction flask and reacted at 100 ℃ for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain compound M5 as a yellow powder. Wherein the adding amount of the palladium acetate is 2mol percent of the M4.
Into a reaction flask were charged 100mmol of M3, 100mmol of M5, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% Pd (PPh) was added 3 ) 4 And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized from toluene to purify it, and a yellow powder of compound A7 was obtained. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 2mol% based on M3.
1 H NMR(400MHz,Chloroform)8.22(d,J＝8.0Hz,2H),8.15-7.96(m,4H),7.72(d,J＝10.0Hz,4H),7.69(s,1H),7.61-7.43(m,7H),7.38-7.25(m,6H).
Synthesis example 7 Synthesis of Compound A15:
100mmol of 2-chlorobenzoxazole and 100m are added into a reaction bottlemol of p-bromophenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ) And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized from toluene to purify it to obtain white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the 2-chlorobenzoxazole.
Into a reaction flask were charged 100mmol of M1, 100mmol of 9-anthraceneboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) was added 3 ) 4 And reacting for 12h at 60 ℃. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M2. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M1.
Adding 100mmol of M2 and 500ml of dichloromethane into a single-mouth bottle, cooling to 0 ℃, adding 200mmol of N-bromosuccinimide (NBS) in batches, keeping the temperature at 0 ℃ for 1h, reacting for 3h, and monitoring the disappearance of the raw materials by thin-layer chromatography (TLC). Water is added into the reaction liquid, ethyl acetate is used for extraction, and the organic phase is concentrated to obtain brown solid M3.
Into a reaction flask were charged 100mmol of 3-bromo-5-chloroiodobenzene, 100mmol of 4-cyanophenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) was added 3 ) 4 And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder M4. Wherein, pd (PPh) 3 ) 4 The amount of the compound (b) added is 1mol% of 3-bromo-5-chloroiodobenzene.
100mmol of M4, 100mmol of pinacol diboron, 29.4g of potassium carbonate (300 mmol), 800ml of dioxane and 1mol% of palladium acetate were charged into a reaction flask and reacted at 100 ℃ for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain compound M5 as a yellow powder. Wherein the adding amount of the palladium acetate is 2mol percent of the M4.
Into a reaction flask were charged 100mmol of M5, 100mmol of 2-chlorobenzoxazole, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) was added 3 ) 4 And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M6. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M5.
100mmol of M6, 100mmol of pinacol diborate, 29.4g of potassium carbonate (300 mmol), 800ml of dioxane and 1mol% of palladium acetate were charged in a reaction flask and reacted at 100 ℃ for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain compound M7 as a yellow powder. Wherein, the adding amount of palladium acetate is 2mol percent of M6.
Into a reaction flask were added 100mmol of M3, 200mmol of M7, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) was added 3 ) 4 And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized from toluene to purify it, to obtain compound a15 as a yellow powder. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 2mol% based on M3.
1 H NMR(400MHz,Chloroform)8.34(d,J＝8.8Hz,4H),8.26(s,1H),8.09–7.81(m,5H),7.74-7.56(m,4H),7.46(d,J＝6.8Hz,4H),7.43-7.32(m,5H),7.21(t,J＝10.0Hz,4H).
Synthesis example 8 Synthesis of Compound A24:
Into a reaction flask were charged 100mmol of M1, 100mmol of 4-pyridineboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) was added 3 ) 4 And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M2. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M1.
100mmol of M2, 100mmol of pinacol diboron, 29.4g of potassium carbonate (300 mmol), 800ml of dioxane and 1mol% of palladium acetate were charged into a reaction flask and reacted at 100 ℃ for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain compound M3 as a yellow powder. Wherein, the adding amount of palladium acetate is 2mol percent of M2.
Into a reaction flask were charged 200mmol of M3, 100mmol of 9,10-dibromoanthracene, 41.4g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh) was added 3 ) 4 And reacting at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized from toluene to purify it to obtain compound a24 as a yellow powder. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M3.
1 H NMR(400MHz,Chloroform)8.71(s,2H),8.21(s,2H),7.93(d,J＝10.0Hz,4H),7.85(s,2H),7.79(d,J＝10.0Hz,6H),7.43-7.25(m,14H).
Other compounds of the present application can be synthesized by selecting appropriate starting materials according to the ideas of the above synthesis examples 1 to 8, and also by selecting any other appropriate methods and starting materials.
Example 1
Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing in deionized water, carrying out ultrasonic degreasing in an acetone-ethanol mixed solvent, baking in a clean environment until water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy solar ion beams;
then, the glass substrate with the anode is placed in a vacuum chamber and is vacuumized to be less than 10 DEG -5 In the torr state, a hole injection layer is evaporated on the anode layer film in vacuum, the material of the hole injection layer comprises a hole injection layer material HT-11 and a p-type dopant p-1, and evaporation is carried out by utilizing a multi-source co-evaporation method, wherein the evaporation rate of the hole injection layer material HT-11 is adjusted to be 0.1nm/s, the evaporation rate of the p-type dopant p-1 is 3 percent of the evaporation rate of the hole injection layer material HT-11, and the thickness of the evaporation film is 10nm; the hole injection layer material HT-11 and the p-type dopant p-1 are as follows:
and then, vacuum evaporating a hole transport material HT-5 on the hole injection layer to form the hole transport layer, wherein the evaporation rate is 0.1nm/s, the evaporation film thickness is 80nm, and the hole transport material HT-5 is as follows:
then, a light-emitting layer is evaporated on the hole transport layer in vacuum, the light-emitting layer comprises a main material BH-2 and a fluorescent dopant BD-1, evaporation is carried out by using a multi-source co-evaporation method, wherein the evaporation rate of the main material BH-2 is adjusted to be 0.1nm/s, the evaporation rate of the fluorescent dopant BD-1 is 3% of the evaporation rate of the main material BH-2, and the thickness of the evaporation film is 30nm; the host material BH-2 and the fluorescent dopant BD-1 are as follows:
then, an electron transport layer is vacuum-evaporated on the luminescent layer, wherein the electron transport material is a compound A1, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 30nm; the electron transport material A1 was as follows:
then, carrying out vacuum evaporation on the LiF with the thickness of 0.5nm on the electron transport layer to serve as an electron injection layer, wherein the evaporation rate is 0.1nm/s;
and finally, performing vacuum evaporation on the electron injection layer to form an Al layer with the thickness of 150nm as a cathode electrode of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s.
Examples 2 to 8
The same as example 1 except that the electron transporting material was A2, A3, A4, A5, A6, a10 or a13, respectively, instead of A1. See table 1 for details.
Comparative example 1
The same as example 1 except that ET-32 was used as the electron transporting material; ET-32 is as follows:
the organic electroluminescent device prepared by the above process was subjected to the following property measurements:
the organic electroluminescent devices prepared in examples 1 to 8 and comparative example 1 were measured for driving voltage, current efficiency and lifetime at the same luminance using a digital source meter and a luminance meter, and specifically, the luminance of the organic electroluminescent device was measured to reach 1000cd/m at a rate of 0.1V/sec by increasing the voltage 2 The current voltage is the driving voltage, and the current density at the moment is measured; the ratio of the brightness to the current density is the current efficiency; life test of LT95The following test runs were made: using a luminance meter at 1000cd/m 2 The luminance drop of the organic electroluminescent device was measured to 950cd/m by maintaining a constant current at luminance 2 Time in hours. The results are shown in Table 1.
Table 1 performance results of organic electroluminescent devices
As can be seen from table 1, the compounds A1, A2, A3, A4, A5, A7, a15, and a24 prepared in the present application as electron transport materials for organic electroluminescent devices can effectively reduce driving voltage, improve current efficiency, and prolong the service life of the devices, and are electron transport materials with good performance.
The above description is only for the preferred embodiment of the present application, and is not intended to limit the scope of the present application. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present application are included in the protection scope of the present application.
Claims (7)
1. A compound of formula (I):
wherein,
L 1 and L 2 Each independently selected from a bond, C unsubstituted or substituted by Rc 6 -C 30 Arylene, C unsubstituted or substituted by Rc 3 -C 30 A heteroarylene group;
R 1 -R 8 each independently selected from hydrogen, deuterium, C 1 -C 10 Alkyl, C unsubstituted or substituted by Rc 6 -C 30 Aryl, C unsubstituted or substituted by Rc 3 -C 30 Heteroaryl radical, R 1 -R 8 Wherein two adjacent groups can be connected to form a ring;
each X is independently selected from O or S;
Y 1 -Y 8 each independently selected from hydrogen, C unsubstituted or substituted by Rc 6 -C 30 Aryl, C unsubstituted or substituted by Rc 3 -C 30 Heteroaryl radical, Y 1 -Y 8 Wherein two adjacent groups can be connected to form a ring;
each heteroatom on the heteroaryl or heteroarylene is independently selected from O, S or N;
the substituents Rc of each group are each independently selected from deuterium, halogen, nitro, cyano, C 1 -C 4 Alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
2. The compound of claim 1, wherein L 1 And L 2 Each independently selected from a bond, C unsubstituted or substituted by Rc 6 -C 18 Arylene, C unsubstituted or substituted by Rc 3 -C 18 A heteroarylene group.
3. The compound of claim 1, wherein said L 1 And L 2 Each independently selected from the group consisting of a bond, a subunit of the following compound unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene.
4. The compound of claim 1, wherein the compound is selected from the following compounds A1 to a 25:
5. an electron transport material comprising at least one of the compounds of any one of claims 1-4.
6. An organic electroluminescent device comprising at least one of the electron transport materials of claim 5.
7. A display device comprising the organic electroluminescent device according to claim 6.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007258362A (en) * | 2006-03-22 | 2007-10-04 | Sanyo Electric Co Ltd | Organic electroluminescent element |
| CN101784634A (en) * | 2007-03-28 | 2010-07-21 | 葛来西雅帝史派有限公司 | Thiazole system organic electroluminescent compounds and organic light emitting diode using the same |
| US20130105777A1 (en) * | 2011-11-01 | 2013-05-02 | Universal Display Corporation | Reducing oled device efficiency at low luminance |
| CN104835921A (en) * | 2014-02-07 | 2015-08-12 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent device |
| CN105051019A (en) * | 2013-04-04 | 2015-11-11 | 捷恩智株式会社 | Electron transport material and organic electroluminescent device using same |
| CN108276342A (en) * | 2018-04-04 | 2018-07-13 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device of the structure containing anthracene |
| CN110615782A (en) * | 2018-06-20 | 2019-12-27 | 北京鼎材科技有限公司 | Organic compound and organic electroluminescent device containing the same |
| CN112500397A (en) * | 2020-12-18 | 2021-03-16 | 武汉尚赛光电科技有限公司 | Organic electroluminescent material with dibenzofuran-connected anthracene core structure and preparation method and device thereof |
| CN113264911A (en) * | 2021-04-30 | 2021-08-17 | 烟台显华化工科技有限公司 | Compound, organic light-emitting material and organic electroluminescent device |
-
2021
- 2021-10-12 CN CN202111188684.9A patent/CN115974805A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007258362A (en) * | 2006-03-22 | 2007-10-04 | Sanyo Electric Co Ltd | Organic electroluminescent element |
| CN101784634A (en) * | 2007-03-28 | 2010-07-21 | 葛来西雅帝史派有限公司 | Thiazole system organic electroluminescent compounds and organic light emitting diode using the same |
| US20130105777A1 (en) * | 2011-11-01 | 2013-05-02 | Universal Display Corporation | Reducing oled device efficiency at low luminance |
| CN105051019A (en) * | 2013-04-04 | 2015-11-11 | 捷恩智株式会社 | Electron transport material and organic electroluminescent device using same |
| CN104835921A (en) * | 2014-02-07 | 2015-08-12 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent device |
| CN108276342A (en) * | 2018-04-04 | 2018-07-13 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device of the structure containing anthracene |
| CN110615782A (en) * | 2018-06-20 | 2019-12-27 | 北京鼎材科技有限公司 | Organic compound and organic electroluminescent device containing the same |
| CN112500397A (en) * | 2020-12-18 | 2021-03-16 | 武汉尚赛光电科技有限公司 | Organic electroluminescent material with dibenzofuran-connected anthracene core structure and preparation method and device thereof |
| CN113264911A (en) * | 2021-04-30 | 2021-08-17 | 烟台显华化工科技有限公司 | Compound, organic light-emitting material and organic electroluminescent device |
Non-Patent Citations (2)
| Title |
|---|
| KENJI OKUMOTO ET AL.: "Green fluorescent organic light-emitting device with external quantum efficiency of nearly 10%", APPLIED PHYSICS LETTERS, vol. 89, pages 1 - 3 * |
| RONGZHEN CUI ET AL.: "Highly efficient green and white fluorescent organic electroluminescent devices with co-doped electron transport material as both supplementary host and blue emitter", JOURNAL OF LUMINESCENCE, vol. 204, pages 668 - 675 * |
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