WO2022213854A1 - Carbazole derivative and use thereof - Google Patents
Carbazole derivative and use thereof Download PDFInfo
- Publication number
- WO2022213854A1 WO2022213854A1 PCT/CN2022/083968 CN2022083968W WO2022213854A1 WO 2022213854 A1 WO2022213854 A1 WO 2022213854A1 CN 2022083968 W CN2022083968 W CN 2022083968W WO 2022213854 A1 WO2022213854 A1 WO 2022213854A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- groups
- aromatic
- ring system
- substituted
- group
- Prior art date
Links
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract 15
- 239000000463 material Substances 0.000 claims abstract description 52
- 239000010410 layer Substances 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 238000005401 electroluminescence Methods 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- -1 NR 12 Inorganic materials 0.000 claims description 22
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 230000000903 blocking effect Effects 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002560 nitrile group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004431 deuterium atom Chemical group 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 7
- 150000001975 deuterium Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 238000005538 encapsulation Methods 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 102220060025 rs141586345 Human genes 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 34
- 150000001716 carbazoles Chemical class 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 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
- 238000007639 printing Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000000706 filtrate Substances 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
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- WUYYVOWEBMOELQ-UHFFFAOYSA-N 1-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2Br WUYYVOWEBMOELQ-UHFFFAOYSA-N 0.000 description 2
- UFOVULIWACVAAC-UHFFFAOYSA-N 1-ethynyl-2-methoxybenzene Chemical group COC1=CC=CC=C1C#C UFOVULIWACVAAC-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- FWAGYANFBMIHFQ-UHFFFAOYSA-N 1-ethynyl-2-nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C#C FWAGYANFBMIHFQ-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 1
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- CPDDXQJCPYHULE-UHFFFAOYSA-N 4,5,14,16-tetrazapentacyclo[9.7.1.12,6.015,19.010,20]icosa-1(18),2,4,6,8,10(20),11(19),12,14,16-decaene Chemical group C1=CC(C2=CC=CC=3C2=C2C=NN=3)=C3C2=CC=NC3=N1 CPDDXQJCPYHULE-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- IUKNPBPXZUWMNO-UHFFFAOYSA-N 5,12-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4,6,8(16),9,11,13-octaene Chemical compound N1=CC=C2C=CC3=NC=CC4=CC=C1C2=C43 IUKNPBPXZUWMNO-UHFFFAOYSA-N 0.000 description 1
- NHWJSCHQRMCCAD-UHFFFAOYSA-N 5,14-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4,6,8(16),9,11(15),12-octaene Chemical compound C1=CN=C2C=CC3=NC=CC4=CC=C1C2=C43 NHWJSCHQRMCCAD-UHFFFAOYSA-N 0.000 description 1
- PODJSIAAYWCBDV-UHFFFAOYSA-N 5,6-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4(16),5,7,9,11(15),12-octaene Chemical compound C1=NN=C2C=CC3=CC=CC4=CC=C1C2=C43 PODJSIAAYWCBDV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- ZPIPUFJBRZFYKJ-UHFFFAOYSA-N C1=NC=C2C=CC3=CN=CC4=CC=C1C2=C34 Chemical compound C1=NC=C2C=CC3=CN=CC4=CC=C1C2=C34 ZPIPUFJBRZFYKJ-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 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 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.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 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- BZHGXQBPJUHVFW-UHFFFAOYSA-N toluene;tritert-butylphosphane Chemical compound CC1=CC=CC=C1.CC(C)(C)P(C(C)(C)C)C(C)(C)C BZHGXQBPJUHVFW-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
Images
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
- C07D491/14—Ortho-condensed systems
- C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- 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
- C07D495/14—Ortho-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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the invention belongs to the technical field of materials for organic electroluminescence elements, and particularly relates to a carbazole derivative and its application.
- Organic electroluminescence is mainly divided into fluorescence and phosphorescence, but according to the theory of spin quantum statistics, the probability of singlet excitons and triplet excitons is 1:3, which is the theoretical limit of fluorescence from singlet exciton radiative transitions is 25%, and the theoretical limit of the fluorescence of triplet exciton radiative transitions is 75%. How to utilize the energy of 75% triplet excitons becomes a top priority.
- Forrest et al. found that the phenomenon of phosphorescent electroluminescence broke through the limit of 25% quantum efficiency of organic electroluminescent materials, which aroused extensive attention to metal complex phosphorescent materials. Since then, people have carried out a lot of research on phosphorescent materials.
- the present invention provides a novel carbazole derivative.
- the carbazole derivative of the present invention as a raw material for materials for organic electroluminescence elements, can provide reduced startup voltage and high luminous efficiency.
- a carbazole derivative the structural formula of the carbazole derivative is shown in formula (I):
- any two adjacent groups W 1 , W 2 , W 3 , W 4 represent groups of the following formula (II),
- Z represents, identically or differently, CR or N at each occurrence, and ⁇ indicates the corresponding adjacent groups W and W, W and W , or W and W in formula I ;
- T 1 , T 2 represent O, S, NAr 2 or CR 10 R 11 ;
- R 1 to R 11 are the same or different, and are selected from hydrogen, deuterium, straight chain alkyl with C 1 to C 40 , straight chain heteroalkyl with C 1 to C 40 , branched chain with C 3 to C 40 or Cyclic alkyl, branched or cyclic heteroalkyl with C3 - C40 , alkenyl or alkynyl with C2 - C40 , aromatic ring system or heteroalkyl with 5-60 carbon atoms
- An aromatic ring system in which each of R 1 to R 11 may be substituted with one or more groups R, and in which two or more adjacent substituted groups may be optionally joined or fused to form monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems;
- Ar 1 and Ar 2 are the same or different, and are selected from linear alkyl groups with C 1 to C 40 , linear heteroalkyl groups with C 1 to C 40 , branched or cyclic alkanes with C 3 to C 40 group, branched or cyclic heteroalkyl group with C3 - C40 , alkenyl or alkynyl group with C2 - C40 , aromatic ring system or heteroaromatic ring system with 5-60 carbon atoms , the ring system may be substituted by one or more groups R;
- Ar 3 is the same or different at each occurrence and is selected from aromatic or heteroaromatic ring systems having 5 to 30 carbon atoms, which may be substituted by one or more non-aromatic groups R 13 ; this The two groups Ar 3 bound to the same nitrogen or phosphorus atom can also be bridged to each other by a single bond or a bridging group selected from N(R 13 ), C(R 13 ) 2 , oxygen or sulfur;
- R 13 is selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, aliphatic hydrocarbon group with C 1 -C 20 , aromatic ring or heteroaromatic ring system with 5-30 carbon atoms, wherein one of R 13 or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms or nitrile groups, wherein two or more adjacent substituents R 13 may form with each other a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring Tie.
- An aromatic or heteroaromatic ring system in the sense of the present invention is intended to be taken to mean a system which does not necessarily have to contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups can also consist of non-aromatic units For example C, N, O or S atoms are attached.
- aryl or heteroaryl groups can also consist of non-aromatic units For example C, N, O or S atoms are attached.
- two or more aryl groups are linked by, for example, short alkyl groups, such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine
- Systems of diaryl ethers and the like are also taken to mean aromatic ring systems in the sense of the present invention.
- Aryl in the sense of the present invention contains 5 to 60 carbon atoms
- heteroaryl in the sense of the present invention contains 5 to 60 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5 ; the heteroatom is preferably selected from N, O or S.
- Aryl or heteroaryl here is taken to mean simple aromatic rings, i.e., benzene, naphthalene, etc., or simple heteroaromatic rings, such as pyridine, pyrimidine, thiophene, etc., or fused aryl or heteroaryl groups bases, such as anthracene, phenanthrene, quinoline, isoquinoline, etc.
- Aromatic rings connected to each other by single bonds, such as biphenyls, are on the contrary not referred to as aryl or heteroaryl groups, but as aromatic ring systems.
- aliphatic hydrocarbon radicals or alkyl radicals or alkenyl radicals or alkynyl radicals which contain from 1 to 40 carbon atoms in the sense of the present invention and in which individual hydrogen atoms or -CH 2 - radicals can also be substituted by the aforementioned radicals are preferably considered to be Refers to the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, hep
- the alkoxy group preferably has 1 to 40 carbon atoms and is considered to be methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy base, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-heptyloxy Octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.
- Heteroalkyl groups preferably have 1 to 40 carbon atoms, and refer to groups in which individual hydrogen atoms or -CH 2 - groups may be substituted by oxygen, sulfur, halogen atoms, and are considered to refer to alkoxy, Alkylthio, fluoroalkoxy, fluoroalkylthio, especially methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy Oxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio group, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoroe
- cycloalkyl, cycloalkenyl can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl , cycloheptenyl, wherein one or more -CH 2 - groups may be replaced by the above-mentioned groups; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms or nitrile groups.
- aromatic or heteroaromatic ring atoms according to the invention which in each case may also be substituted by the aforementioned radicals R 13 , are in particular radicals derived from benzene, Naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, benzene, terphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, trimerindene, heterotrimerindene, spirotrimerindene, spiroheterotrimerindene, furan, benzofuran, is
- formula (I) mainly includes the structures shown in the following formula (I)-A to formula (I)-F:
- R 1 to R 8 , T 1 , T 2 , Ar 1 and R are the same as those defined above.
- R 1 to R 8 are the same or different, and are selected from hydrogen, deuterium, an aromatic ring system or a heteroaromatic ring system with 5 to 60 carbon atoms, wherein each group may be composed of one or more The group R is substituted, wherein two or more adjacent substituted groups may be optionally joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system;
- T 1 and T 2 represent O or S
- the Ar 1 is selected from an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, and the ring system may be substituted by one or more groups R.
- carbazole derivatives mainly include the following CJHL239 ⁇ CJHL460:
- carbazole derivatives are materials for organic electroluminescence elements, materials for organic field effect transistors or materials for organic thin film solar cells.
- An organic electroluminescence element comprising a first electrode, a second electrode and a multilayer organic layer between the first electrode and the second electrode, at least one of the organic layers comprises the carbazole derivative .
- the organic electroluminescent element includes a cathode, an anode and at least one light-emitting layer. In addition to these layers, it may also contain other layers, for example in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, excitation layers Sub-blocking layer, electron blocking layer and/or charge generating layer. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that each of these layers does not have to be present.
- the organic electroluminescent device described herein may comprise one light-emitting layer, or it may comprise multiple light-emitting layers.
- various light-emitting compounds capable of emitting light are used in the light-emitting layer.
- Particular preference is given to systems having three emitting layers, wherein the three layers can exhibit blue, green and red emission. If more than one light-emitting layer is present, according to the present invention, at least one of these layers comprises the carbazole derivative of the present invention.
- organic electroluminescent elements in which one or more layers are applied by means of a sublimation method, in which the layer or layers are applied by vapor deposition in a vacuum sublimation device at an initial pressure of less than 10 ⁇ 5 Pa, preferably less than 10 ⁇ 6 Pa The material is applied.
- the initial pressure may also be even lower, eg below 10 ⁇ 7 Pa.
- a particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is thus structured.
- organic electroluminescent elements from solution, for example by spin coating, or by means of any desired printing method such as screen printing, flexographic printing, lithographic printing, photoinduced thermography, thermal transfer printing, spraying Ink printing or nozzle printing to create one or more layers.
- Soluble compounds are obtained, for example, by appropriately substituting compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers.
- hybrid methods in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapour deposition.
- the organic layer further includes one or more selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a light refraction layer.
- the organic electroluminescent element of the present invention may be either a top-emitting light-emitting element or a bottom-emitting light-emitting element.
- the structure and preparation method of the organic electroluminescence element of the present invention are not limited.
- the organic electroluminescent element prepared by using the compound of the present invention can reduce the start-up voltage and improve the luminous efficiency and brightness.
- a display device comprising the organic electroluminescence element.
- a lighting device comprising the organic electroluminescence element.
- the material for organic elements of the present invention contains the carbazole derivative of the present invention.
- the material for organic elements may be constituted using the compound of the present invention alone, or may contain other compounds together.
- the carbazole derivative of the present invention contained in the material for an organic electroluminescence element of the present invention can be used as a host material.
- the material for organic electroluminescence elements of the present invention may contain other compounds as dopant materials.
- the material for an organic electroluminescence element of the present invention can also be used as a material for a hole transport layer, an enhancement layer, a light emitting layer, an electron transport layer, a charge generation layer, an electron blocking layer, an encapsulation layer or a photorefractive layer.
- the beneficial effects of the present invention are as follows: the carbazole derivatives described in the present invention have higher triplet energy level and high glass transition temperature, are suitable for use as materials for organic electroluminescence elements, and contain
- the carbazole derivative-based material for an organic electroluminescent element has the characteristics of low startup voltage, high luminous efficiency and high brightness.
- the carbazole derivatives of the present invention have good thermal stability and film-forming properties, are used in materials for organic electroluminescence elements, organic electroluminescence elements, display devices, and lighting devices, and can prolong the service life, thereby enabling Reduce the manufacturing cost of materials for organic electroluminescence elements, organic electroluminescence elements, display devices, and lighting devices.
- FIG. 1 is a schematic diagram of a bottom emission example of the organic electroluminescence device of the present invention.
- FIG. 2 is a schematic diagram of a top emission example of the organic electroluminescent device of the present invention.
- test instruments and methods for performance testing of OLED materials and components in the following examples are as follows:
- Luminance and chromaticity coordinates tested with a spectral scanner PhotoResearch PR-715;
- Life Test Use LTS-1004AC Life Test Device.
- the preparation method of intermediate A1 comprises the steps:
- the following mixture of compounds A1 and A2 is used as the green light host material, wherein the mass ratio of A1 and A2 is 11:9, the following compound B is used as the green light doping material, the compound C is used as the hole injection material, and the compound D As a hole transport material, compound E is used as a red light material, compound F is used as a red light dopant material, compound G is used as an electron transport dopant material, and LiQ is used as an electron transport host material.
- the green light element was fabricated by successively using an EL vapor deposition machine manufactured by DOV Corporation to vapor-deposit on ITO glass, and an organic electroluminescent element as a green light was fabricated.
- the red light element was fabricated by successively using an EL vapor deposition machine manufactured by DOV Company to vapor-deposit on the ITO glass, and an organic electroluminescence element as a red light was fabricated.
- Compound A was replaced with compounds CJHL239 to CJHL460 of the present invention, and green light organic electroluminescence elements were prepared according to the method of Comparative Example 1.
- the performance test results of the obtained green light organic electroluminescent element are listed in Table 1, where the driving voltage (V), current efficiency (LE), color coordinate (CIE), and half-peak width (FWHM) are measured when the current density of the element is 10 mA/cm 2 and data normalized for voltage, LE, FWHM and LT90% compared to the reference element.
- the green light element prepared from the organic material of the present invention has lower driving voltage, higher current efficiency, and better color purity than the element prepared in Comparative Example 1, and the luminous brightness of the element is initially 2000cd/cm 2 . Under the initial conditions, the lifetime of the device using the compound of the present invention as the green host material is greatly improved.
- Table 1 only lists the properties of some compounds in CJHL239 ⁇ CJHL460.
- the properties of other compounds are basically the same as the structures of the compounds listed in the table. Due to the limited space, they will not be listed one by one.
- a red light element was prepared according to the method of Comparative Example 1, wherein the aforementioned compound E was replaced by the compounds CJHL239 to CJHL460 of the present invention, in addition, /[Compounds of the present invention
- the element prepared from the organic material of the present invention has significantly lower driving voltage, higher current efficiency and better luminous color purity than that of the red light element prepared in Comparative Example 1.
- the LT90% lifetime of the element using the compound of the present invention as the red light host material is 1.1 to 2.7 times that of the comparative element.
- Table 2 only lists the properties of some compounds in CJHL239 ⁇ CJHL460.
- the properties of other compounds are basically the same as the structures of the compounds listed in the table. Due to the limited space, they will not be listed one by one.
- 1 and 2 are respectively a schematic diagram of a bottom emission example of the organic electroluminescence device of the present invention and a schematic diagram of a top emission example of the organic electroluminescence device, the carbazole derivatives prepared by the present invention are included in the luminescence in layer 5.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electromagnetism (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a series of carbazole derivative and a use thereof. The structural formula of the carbazole derivative is as shown in formula (I). The present carbazole derivative has high stability and triplet energy levels, and is suitable for use as a material for an organic electroluminescent element. The material for the organic electroluminescent element containing said carbazole derivative has the characteristics of low starting voltage, high luminous efficiency and high brightness.
Description
本发明属于有机电致发光元件用材料技术领域，具体涉及一种咔唑衍生物及其应用。The invention belongs to the technical field of materials for organic electroluminescence elements, and particularly relates to a carbazole derivative and its application.
最近几年有机电致发光显示技术己趋于成熟，一些产品已进入市场，但在产业化时程中，仍有许多问题亟待解决，特别是用于制作元件的各种有机材料，其载流子注入、传输性能，材料电发光性能、使用寿命、色纯度、各种材料之间及与各电极之间的匹配等，尚有许多问题还未解决。尤其是发光元件在发光效率和使用寿命方面还达不到实用化要求，这大大限制了OLED技术的发展。In recent years, organic electroluminescence display technology has matured, and some products have entered the market. However, in the process of industrialization, there are still many problems to be solved urgently, especially the current-carrying properties of various organic materials used to make components. Sub-injection, transmission performance, material electroluminescence performance, service life, color purity, matching between various materials and between electrodes, etc., there are still many problems that have not been solved. In particular, the luminous efficiency and service life of light-emitting elements have not yet met the practical requirements, which greatly limits the development of OLED technology.
有机电致发光主要分为荧光和磷光，但根据自旋量子统计理论，单重态激子和三重态激子的概率为1:3，即来自单重态激子辐射跃迁的荧光的理论极限为25％，三重态激子辐射跃迁的荧光的理论极限为75％。如何利用75％的三线态激子的能量成为当务之急。1997年Forrest等发现磷光电致发光现象突破了有机电致发光材料量子效率25％效率的限制，引起人们对金属配合物磷光材料的广泛关注。从此，人们对磷光材料进行大量的研究。Organic electroluminescence is mainly divided into fluorescence and phosphorescence, but according to the theory of spin quantum statistics, the probability of singlet excitons and triplet excitons is 1:3, which is the theoretical limit of fluorescence from singlet exciton radiative transitions is 25%, and the theoretical limit of the fluorescence of triplet exciton radiative transitions is 75%. How to utilize the energy of 75% triplet excitons becomes a top priority. In 1997, Forrest et al. found that the phenomenon of phosphorescent electroluminescence broke through the limit of 25% quantum efficiency of organic electroluminescent materials, which aroused extensive attention to metal complex phosphorescent materials. Since then, people have carried out a lot of research on phosphorescent materials.
鉴于以上原因，特提出本发明。In view of the above reasons, the present invention is proposed.
发明内容SUMMARY OF THE INVENTION
为了解决现有技术存在的以上问题，本发明提供了一种新型的咔唑衍生物，本发明的咔唑衍生物作为有机电致发光元件用材料的原料，能够提供启动电压降低、发光效率高、亮度提高的有机电致发光元件用材料以及有机电致发光元件。In order to solve the above problems existing in the prior art, the present invention provides a novel carbazole derivative. The carbazole derivative of the present invention, as a raw material for materials for organic electroluminescence elements, can provide reduced startup voltage and high luminous efficiency. , A material for an organic electroluminescent element with improved brightness, and an organic electroluminescent element.
为了实现上述目的，本发明采用如下技术方案：In order to achieve the above object, the present invention adopts the following technical solutions:
一种咔唑衍生物，所述咔唑衍生物的结构式如式(I)所示：A carbazole derivative, the structural formula of the carbazole derivative is shown in formula (I):
其中，任意两个相邻的基团W
1、W
2、W
3、W
4代表下式(II)的基团，
Wherein, any two adjacent groups W 1 , W 2 , W 3 , W 4 represent groups of the following formula (II),
其中，Z在每次出现时相同或不同地代表CR
9或N，并且^指示式I中的相应的相邻基团W
1和W
2、W
2和W
3，或W
3和W
4；
wherein Z represents, identically or differently, CR or N at each occurrence, and ^ indicates the corresponding adjacent groups W and W, W and W , or W and W in formula I ;
T
1、T
2表示O、S、NAr
2或CR
10R
11；
T 1 , T 2 represent O, S, NAr 2 or CR 10 R 11 ;
R
1～R
11相同或者不同，选自氢、氘、具有C
1～C
40的直链烷基、具有C
1～C
40的直链杂烷基、具有C
3～C
40的支链或环状的烷基、具有C
3～C
40的支链或环状的杂烷基、具有C
2～C
40的烯基或炔基、具有5～60个碳原子的芳香族环系或杂芳族环系中的一种，R
1～R
11中的每个基团可被一个或多个基团R取代，且其中两个或更多个相邻的取代基团可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系；
R 1 to R 11 are the same or different, and are selected from hydrogen, deuterium, straight chain alkyl with C 1 to C 40 , straight chain heteroalkyl with C 1 to C 40 , branched chain with C 3 to C 40 or Cyclic alkyl, branched or cyclic heteroalkyl with C3 - C40 , alkenyl or alkynyl with C2 - C40 , aromatic ring system or heteroalkyl with 5-60 carbon atoms An aromatic ring system in which each of R 1 to R 11 may be substituted with one or more groups R, and in which two or more adjacent substituted groups may be optionally joined or fused to form monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems;
Ar
1、Ar
2相同或者不同，选自具有C
1～C
40的直链烷基、具有C
1～C
40的直链杂烷基、具有C
3～C
40的支链或环状的烷基、具有C
3～C
40的支链或环状的杂烷基、具有C
2～C
40的烯基或炔基、具有5～60个碳原子的芳香族环系或杂芳族环系，所述环系可被一个或多个基团R取代；
Ar 1 and Ar 2 are the same or different, and are selected from linear alkyl groups with C 1 to C 40 , linear heteroalkyl groups with C 1 to C 40 , branched or cyclic alkanes with C 3 to C 40 group, branched or cyclic heteroalkyl group with C3 - C40 , alkenyl or alkynyl group with C2 - C40 , aromatic ring system or heteroaromatic ring system with 5-60 carbon atoms , the ring system may be substituted by one or more groups R;
所述R每次出现时相同或不同，选自氢原子、氘原子、卤素原子、腈基、 硝基、N(Ar
3)
2、N(R
12)
2、C(＝O)Ar
3、C(＝O)R
12、P(＝O)(Ar
3)
2、具有C
1～C
40的直链烷基、具有C
1～C
40的直链杂烷基、具有C
3～C
40的支链或环状的烷基、具有C
3～C
40的支链或环状的杂烷基、具有C
2～C
40的烯基或炔基、具有5～80个碳原子的芳族环或杂芳族环系、具有5～60个碳原子的芳氧基或杂芳氧基中的一种，R基团中的每个基团可被一个或多个基团R
12取代，或这些体系的组合，其中一个或多个非相邻的-CH
2-基团可被R
12C＝CR
12、C≡C、Si(R
12)
2、Ge(R
12)
2、Sn(R
12)
2、C＝O、C＝S、C＝Se、C＝NR
12、P(＝O)(R
12)、SO、SO
2、NR
12、O、S或CONR
12代替，并且其中一个或多个氢原子或被氘原子、卤素原子、腈基或硝基代替，其中两个或更多个相邻的取代基R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系，所述环系可被一个或多个基团R
12取代；
Said R is the same or different at each occurrence, and is selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, nitro group, N(Ar 3 ) 2 , N(R 12 ) 2 , C(=O)Ar 3 , C(=O)R 12 , P(=O)(Ar 3 ) 2 , straight-chain alkyl having C 1 -C 40 , straight-chain heteroalkyl having C 1 -C 40 , C 3 -C 40 branched or cyclic alkyl groups, branched or cyclic heteroalkyl groups with C 3 -C 40 , alkenyl or alkynyl groups with C 2 -C 40 , aromatic groups with 5 to 80 carbon atoms one of a ring or heteroaromatic ring system, an aryloxy or heteroaryloxy group having 5 to 60 carbon atoms, each of the R groups may be substituted by one or more groups R 12 , or a combination of these systems in which one or more non-adjacent -CH 2 - groups may be replaced by R 12 C=CR 12 , C≡C, Si(R 12 ) 2 , Ge(R 12 ) 2 , Sn( R 12 ) 2 , C=O, C=S, C=Se, C=NR 12 , P(=O)(R 12 ), SO, SO 2 , NR 12 , O, S or CONR 12 instead, and wherein One or more hydrogen atoms are either replaced by deuterium atoms, halogen atoms, nitrile or nitro groups, wherein two or more adjacent substituents R can be optionally joined or fused to form monocyclic or polycyclic aliphatic an aromatic, aromatic or heteroaromatic ring system, which may be substituted by one or more groups R 12 ;
R
12每次出现时相同或不同，选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar
3)
2、N(R
13)
2、C(＝O)Ar
3、C(＝O)R
13、P(＝O)(Ar
3)
2、具有C
1～C
40的直链烷基、具有C
1～C
40的直链杂烷基、具有C
3～C
40的支链或环状的烷基、具有C
3～C
40的支链或环状的杂烷基、具有C
2～C
40的烯基或炔基、具有5～60个碳原子的芳族环或杂芳族环系、具有5～60个碳原子的芳氧基或杂芳氧基中的一种，R
12中的每个基团可被一个或多个基团R
13取代，或这些体系的组合，其中一个或多个非相邻的-CH
2-基团可被R
13C＝CR
13、C≡C、Si(R
13)
2、Ge(R
13)
2、Sn(R
13)
2、C＝O、C＝S、C＝Se、C＝NR
13、P(＝O)(R
13)、SO、SO
2、NR
13、O、S或CONR
13代替，并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替，其中两个或更多个相邻的取代基R
12可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系，所述环系可被一个或多个基团R
13取代；
R 12 is the same or different at each occurrence and is selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, nitro group, N(Ar 3 ) 2 , N(R 13 ) 2 , C(=O)Ar 3 , C (=O)R 13 , P(=O)(Ar 3 ) 2 , straight-chain alkyl having C 1 -C 40 , straight-chain heteroalkyl having C 1 -C 40 , straight-chain heteroalkyl having C 3 -C 40 Branched or cyclic alkyl, branched or cyclic heteroalkyl with C3 - C40 , alkenyl or alkynyl with C2 - C40 , aromatic ring with 5-60 carbon atoms or one of heteroaromatic ring systems, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, each group in R 12 may be substituted with one or more groups R 13 , or these Combinations of systems in which one or more non-adjacent -CH2- groups can be replaced by R13C = CR13 , C≡C, Si( R13 ) 2 , Ge( R13 ) 2 , Sn( R13 ) 2 , C=O, C=S, C=Se, C=NR 13 , P(=O)(R 13 ), SO, SO 2 , NR 13 , O, S or CONR 13 instead, and either or Multiple hydrogen atoms can be replaced by deuterium atoms, halogen atoms, nitrile or nitro groups, wherein two or more adjacent substituents R 12 can be optionally joined or fused to form a monocyclic or polycyclic aliphatic , aromatic or heteroaromatic ring systems, which may be substituted by one or more groups R 13 ;
Ar
3在每次出现时相同或不同，选自具有5～30个碳原子的芳族或杂芳族环系，所述环系可被一个或多个非芳族基团R
13取代；此处键合至同一氮原子或磷原子的两个基团Ar
3也可通过单键或选自N(R
13)、C(R
13)
2、氧或硫的桥连基彼此桥连；
Ar 3 is the same or different at each occurrence and is selected from aromatic or heteroaromatic ring systems having 5 to 30 carbon atoms, which may be substituted by one or more non-aromatic groups R 13 ; this The two groups Ar 3 bound to the same nitrogen or phosphorus atom can also be bridged to each other by a single bond or a bridging group selected from N(R 13 ), C(R 13 ) 2 , oxygen or sulfur;
R
13选自氢原子、氘原子、氟原子、腈基、具有C
1～C
20的脂族烃基、具有 5～30个碳原子的芳族环或杂芳族环系，其中R
13中一个或多个氢原子可被氘原子、卤素原子或腈基代替，其中两个或更多个相邻的取代基R
13可彼此形成单环或多环的脂族、芳族或杂芳族环系。
R 13 is selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, aliphatic hydrocarbon group with C 1 -C 20 , aromatic ring or heteroaromatic ring system with 5-30 carbon atoms, wherein one of R 13 or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms or nitrile groups, wherein two or more adjacent substituents R 13 may form with each other a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring Tie.
在本发明意义上的芳族或杂芳族环系旨在被认为是指不必仅含有芳基或杂芳基的体系，而是其中多个芳基或杂芳基还可以由非芳族单元例如C、N、O或S原子连接。因此，例如，和其中两个或更多个芳基被例如短的烷基连接的体系一样，诸如芴、9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚等的体系也被认为是指在本发明意义上的芳族环系。An aromatic or heteroaromatic ring system in the sense of the present invention is intended to be taken to mean a system which does not necessarily have to contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups can also consist of non-aromatic units For example C, N, O or S atoms are attached. Thus, for example, as in systems in which two or more aryl groups are linked by, for example, short alkyl groups, such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, Systems of diaryl ethers and the like are also taken to mean aromatic ring systems in the sense of the present invention.
本发明意义上的芳基含有5～60个碳原子，在本发明意义上的杂芳基含有5～60个碳原子和至少一个杂原子，其条件是碳原子和杂原子的总和至少是5；所述杂原子优选选自N、O或S。此处的芳基或杂芳基被认为是指简单的芳族环，即苯、萘等，或简单的杂芳族环，如吡啶、嘧啶、噻吩等，或稠合的芳基或杂芳基，如蒽、菲、喹啉、异喹啉等。通过单键彼此连接的芳族环，例如联苯，相反地不被称为芳基或杂芳基，而是称为芳族环系。Aryl in the sense of the present invention contains 5 to 60 carbon atoms, and heteroaryl in the sense of the present invention contains 5 to 60 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5 ; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl here is taken to mean simple aromatic rings, i.e., benzene, naphthalene, etc., or simple heteroaromatic rings, such as pyridine, pyrimidine, thiophene, etc., or fused aryl or heteroaryl groups bases, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings connected to each other by single bonds, such as biphenyls, are on the contrary not referred to as aryl or heteroaryl groups, but as aromatic ring systems.
对于本发明意义上的含有1～40个碳原子并且其中单独的氢原子或-CH
2-基团还可被上述基团取代的脂族烃基或者烷基或者烯基或炔基优选被认为是指如下基团：甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、新戊基、环戊基、正己基、新己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。烷氧基优选具有1～40个碳原子的烷氧基被认为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。杂烷基优选具有1～40个碳原子的烷基，是指其中单独的氢原子或-CH
2-基团可被氧、硫、卤素原子取代的基团，被认为是指烷氧基、烷硫基、氟代的烷 氧基、氟代的烷硫基，特别是指甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基、三氟甲氧基、五氟乙氧基、五氟乙硫基、2,2,2-三氟乙氧基、2,2,2-三氟乙硫基、乙烯氧基、乙烯硫基、丙烯氧基、丙烯硫基、丁烯硫基、丁烯氧基、戊烯氧基、戊烯硫基、环戊烯氧基、环戊烯硫基、己烯氧基、己烯硫基、环己烯氧基、环己烯硫基、乙炔氧基、乙炔硫基、丙炔氧基、丙炔硫基、丁炔氧基、丁炔硫基、戊炔氧基、戊炔硫基、己炔氧基、己炔硫基。
For aliphatic hydrocarbon radicals or alkyl radicals or alkenyl radicals or alkynyl radicals which contain from 1 to 40 carbon atoms in the sense of the present invention and in which individual hydrogen atoms or -CH 2 - radicals can also be substituted by the aforementioned radicals are preferably considered to be Refers to the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptyl Alkenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. The alkoxy group preferably has 1 to 40 carbon atoms and is considered to be methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy base, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-heptyloxy Octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy. Heteroalkyl groups preferably have 1 to 40 carbon atoms, and refer to groups in which individual hydrogen atoms or -CH 2 - groups may be substituted by oxygen, sulfur, halogen atoms, and are considered to refer to alkoxy, Alkylthio, fluoroalkoxy, fluoroalkylthio, especially methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy Oxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio group, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoroethylthio, vinyloxy, vinylthio radical, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio base, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio group, hexynyloxy, hexynylthio.
一般来说，根据本发明的环烷基、环烯基可为环丙基、环丁基、环戊基、环己基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基，其中一个或多个-CH
2-基团可被上述基团代替；此外，一个或多个氢原子还可被氘原子、卤素原子或腈基代替。
In general, cycloalkyl, cycloalkenyl according to the present invention can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl , cycloheptenyl, wherein one or more -CH 2 - groups may be replaced by the above-mentioned groups; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms or nitrile groups.
根据本发明的芳族或杂芳族环原子，在每种情况下还可被上述基团R
13取代的芳族或杂芳族环系，特别是指衍生自如下物质的基团：苯、萘、蒽、苯并蒽、菲、芘、
苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、顺式或反式茚并咔唑、顺式或反式吲哚并咔唑、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并[5,6]喹啉、苯并[6,7]喹啉、苯并[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂苯并菲、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘，4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、 1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑或者衍生自这些体系的组合的基团。
The aromatic or heteroaromatic ring atoms according to the invention, which in each case may also be substituted by the aforementioned radicals R 13 , are in particular radicals derived from benzene, Naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, benzene, terphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, trimerindene, heterotrimerindene, spirotrimerindene, spiroheterotrimerindene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline , acridine, phenanthridine, benzo[5,6]quinoline, benzo[6,7]quinoline, benzo[7,8]quinoline, phenothiazine, phenoxazine, pyrazole, indazole , imidazole, benzimidazole, naphthimidazole, phenanthroimidazole, pyridimidazole, pyrazinimidazole, quinoxalineimidazole, oxazole, benzoxazole, naphthoxazole, anthraxazole, phenanthroline oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazathene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene Pyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorochrome, naphthyridine, azacarbazole, benzocarboline, carboline, phenanthrene Roroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2, 5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3, 4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2 ,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole or groups derived from combinations of these systems.
进一步地，所述式(I)主要包括以下式(I)-A～式(I)-F所示的结构：Further, the formula (I) mainly includes the structures shown in the following formula (I)-A to formula (I)-F:
其中R
1～R
8、T
1、T
2、Ar
1和R的定义与上述的定义相同。
The definitions of R 1 to R 8 , T 1 , T 2 , Ar 1 and R are the same as those defined above.
进一步的，所述R
1～R
8相同或者不同，选自氢、氘、具有5～60个碳原子的 芳香族环系或杂芳族环系，其中每个基团可被一个或多个基团R取代，其中两个或更多个相邻的取代基团可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系；
Further, the R 1 to R 8 are the same or different, and are selected from hydrogen, deuterium, an aromatic ring system or a heteroaromatic ring system with 5 to 60 carbon atoms, wherein each group may be composed of one or more The group R is substituted, wherein two or more adjacent substituted groups may be optionally joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system;
进一步的，所述T
1、T
2表示O或S；
Further, the T 1 and T 2 represent O or S;
进一步的，所述Ar
1选自具有5～60个碳原子的芳香族环系或杂芳族环系，所述环系可被一个或多个基团R取代。
Further, the Ar 1 is selected from an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, and the ring system may be substituted by one or more groups R.
进一步的，所述咔唑衍生物主要包括如下CJHL239～CJHL460所示：Further, the carbazole derivatives mainly include the following CJHL239～CJHL460:
一种所述的咔唑衍生物在有机元件用材料中的应用。An application of the carbazole derivative in a material for organic components.
进一步的，所述咔唑衍生物为有机电致发光元件用材料、有机场效应晶体管用材料或有机薄膜太阳能电池用材料。Further, the carbazole derivatives are materials for organic electroluminescence elements, materials for organic field effect transistors or materials for organic thin film solar cells.
进一步的，所述咔唑衍生物在发光层材料、空穴输送/空穴阻挡层材料或封装层材料中的应用。Further, the application of the carbazole derivatives in light-emitting layer materials, hole transport/hole blocking layer materials or encapsulation layer materials.
一种有机电致发光元件，包括第一电极、第二电极和位于第一电极和第二电极之间的多层有机层，所述有机层中的至少一层包含所述的咔唑衍生物。An organic electroluminescence element, comprising a first electrode, a second electrode and a multilayer organic layer between the first electrode and the second electrode, at least one of the organic layers comprises the carbazole derivative .
所述有机电致发光元件包含阴极、阳极和至少一个发光层。除了这些层之外，它还可以包含其它的层，例如在每种情况下，包含一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。具有例如激子阻挡功能的中间层同样可引入两个发光层之间。然而，应当指出，这些层中的每个并非必须都存在。此处所述有机电致发光装置可包含一个发光层，或者它可包含多个发光层。即，将能够发光的多种发光化合物用于所述发光层中。特别优选具有三个发光层的体系，其中所述三个层可显示蓝色、绿色和红色发光。如果存在多于一个的发光层，则根据本发明，这些层中的至少一个层包含本发明的咔唑衍生物。The organic electroluminescent element includes a cathode, an anode and at least one light-emitting layer. In addition to these layers, it may also contain other layers, for example in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, excitation layers Sub-blocking layer, electron blocking layer and/or charge generating layer. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that each of these layers does not have to be present. The organic electroluminescent device described herein may comprise one light-emitting layer, or it may comprise multiple light-emitting layers. That is, various light-emitting compounds capable of emitting light are used in the light-emitting layer. Particular preference is given to systems having three emitting layers, wherein the three layers can exhibit blue, green and red emission. If more than one light-emitting layer is present, according to the present invention, at least one of these layers comprises the carbazole derivative of the present invention.
在根据本发明的有机电致发光元件的其它层中，特别是在空穴传输层中以及在空穴阻挡层和薄膜封装层中，所有材料可以按照根据现有技术通常所使用的方式来使用。本领域普通技术人员因此将能够在不付出创造性劳动的情况下与根据本发明的发光层组合使用关于有机电致发光元件所知的所有材料。In the other layers of the organic electroluminescent element according to the invention, in particular in the hole transport layer as well as in the hole blocking layer and the thin-film encapsulation layer, all materials can be used in the manner generally used according to the prior art . A person skilled in the art will therefore be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive step.
此外优选如下的有机电致发光元件，借助于升华方法施加一个或多个层，其中在真空升华装置中在低于10
-5Pa、优选低于10
-6Pa的初压下通过气相沉积 来施加所述材料。然而，所述初压还可能甚至更低，例如低于10
-7Pa。
Furthermore, preference is given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation method, in which the layer or layers are applied by vapor deposition in a vacuum sublimation device at an initial pressure of less than 10 −5 Pa, preferably less than 10 −6 Pa The material is applied. However, the initial pressure may also be even lower, eg below 10 −7 Pa.
同样优选如下的有机电致发光元件，借助于有机气相沉积方法或借助于载气升华来施加一个或多个层，其中，在10
-5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸气喷印方法，其中所述材料通过喷嘴直接施加，并且因此是结构化的。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapour deposition method or by means of sublimation of a carrier gas, wherein the material is applied at a pressure of between 10 −5 Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is thus structured.
此外优选如下的有机电致发光元件，从溶液中，例如通过旋涂，或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷，来产生一个或多个层。可溶性化合物，例如通过适当的取代式(I)所示的化合物获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法，其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。Also preferred are organic electroluminescent elements, from solution, for example by spin coating, or by means of any desired printing method such as screen printing, flexographic printing, lithographic printing, photoinduced thermography, thermal transfer printing, spraying Ink printing or nozzle printing to create one or more layers. Soluble compounds are obtained, for example, by appropriately substituting compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Also possible are hybrid methods in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapour deposition.
进一步地，所述有机层还包括选自电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层、发光层、光折射层的一种以上。Further, the organic layer further includes one or more selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a light refraction layer.
本发明的有机电致发光元件既可以是顶发射光元件，又可以是底发射光元件。本发明的有机电致发光元件的结构和制备方法没有限定。采用本发明的化合物制得的有机电致发光元件可降低启动电压、提高发光效率和亮度。The organic electroluminescent element of the present invention may be either a top-emitting light-emitting element or a bottom-emitting light-emitting element. The structure and preparation method of the organic electroluminescence element of the present invention are not limited. The organic electroluminescent element prepared by using the compound of the present invention can reduce the start-up voltage and improve the luminous efficiency and brightness.
一种显示装置，包括所述的有机电致发光元件。A display device comprising the organic electroluminescence element.
一种照明装置，包括所述的有机电致发光元件。A lighting device, comprising the organic electroluminescence element.
本发明的有机元件用材料含有本发明的咔唑衍生物。有机元件用材料可以单独使用本发明的化合物构成，也可以同时含有其他化合物。The material for organic elements of the present invention contains the carbazole derivative of the present invention. The material for organic elements may be constituted using the compound of the present invention alone, or may contain other compounds together.
本发明的有机电致发光元件用材料中所含有的本发明的咔唑衍生物可以用作主体材料。此时，本发明的有机电致发光元件用材料中可以含有作为掺杂材料的其他化合物。The carbazole derivative of the present invention contained in the material for an organic electroluminescence element of the present invention can be used as a host material. In this case, the material for organic electroluminescence elements of the present invention may contain other compounds as dopant materials.
本发明的有机电致发光元件用材料还可以作为空穴传输层、增强层、发光层、电子传输层、电荷产生层、电子阻挡层、封装层或光折射层用材料。The material for an organic electroluminescence element of the present invention can also be used as a material for a hole transport layer, an enhancement layer, a light emitting layer, an electron transport layer, a charge generation layer, an electron blocking layer, an encapsulation layer or a photorefractive layer.
与现有技术相比，本发明的有益效果为：本发明所述的咔唑衍生物具有较高的三重态能级、高的玻璃化温度，适宜作为有机电致发光元件用材料使用，含有所述的咔唑衍生物的有机电致发光元件用材料，具有启动电压低，发光效率和亮度高的特点。另外，本发明的咔唑衍生物具有良好的热稳定性和成膜性能，应用在有机电致发光元件用材料、有机电致发光元件、显示装置、照明装置中，能够延长使用寿命，从而能够降低有机电致发光元件用材料、有机电致发光元件、显示装置、照明装置的制造成本。Compared with the prior art, the beneficial effects of the present invention are as follows: the carbazole derivatives described in the present invention have higher triplet energy level and high glass transition temperature, are suitable for use as materials for organic electroluminescence elements, and contain The carbazole derivative-based material for an organic electroluminescent element has the characteristics of low startup voltage, high luminous efficiency and high brightness. In addition, the carbazole derivatives of the present invention have good thermal stability and film-forming properties, are used in materials for organic electroluminescence elements, organic electroluminescence elements, display devices, and lighting devices, and can prolong the service life, thereby enabling Reduce the manufacturing cost of materials for organic electroluminescence elements, organic electroluminescence elements, display devices, and lighting devices.
为了更清楚地说明本发明实施例或现有技术中的技术方案，下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。In order to explain the embodiments of the present invention or the technical solutions in the prior art more clearly, the following briefly introduces the accompanying drawings that need to be used in the description of the embodiments or the prior art. Obviously, the accompanying drawings in the following description are only These are some embodiments of the present invention. For those of ordinary skill in the art, other drawings can also be obtained according to these drawings without creative efforts.
图1是本发明的有机电致发光装置的一个底部发光例子的示意图；1 is a schematic diagram of a bottom emission example of the organic electroluminescence device of the present invention;
图2是本发明的有机电致发光装置的一个顶部发光例子的示意图。FIG. 2 is a schematic diagram of a top emission example of the organic electroluminescent device of the present invention.
附图标记reference number
1-基板、2-阳极、3-空穴注入层、4-空穴传输/电子阻挡层、5-发光层、6-空穴阻挡/电子传输层、7-电子注入层、8-阴极。1-substrate, 2-anode, 3-hole injection layer, 4-hole transport/electron blocking layer, 5-light emitting layer, 6-hole blocking/electron transport layer, 7-electron injection layer, 8-cathode.
为使本发明的目的、技术方案和优点更加清楚，下面将对本发明的技术方案进行详细的描述。显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动的前提下所得到的所有其它实施方式，都属于本发明所保护的范围。In order to make the objectives, technical solutions and advantages of the present invention clearer, the technical solutions of the present invention will be described in detail below. Obviously, the described embodiments are only some, but not all, embodiments of the present invention. Based on the embodiments of the present invention, all other implementations obtained by those of ordinary skill in the art without creative work fall within the protection scope of the present invention.
以下实施例中OLED材料及元件进行性能测试的测试仪器及方法如下：The test instruments and methods for performance testing of OLED materials and components in the following examples are as follows:
OLED元件性能检测条件：OLED component performance testing conditions:
亮度和色度坐标：使用光谱扫描仪PhotoResearch PR-715测试；Luminance and chromaticity coordinates: tested with a spectral scanner PhotoResearch PR-715;
电流密度和起亮电压：使用数字源表Keithley 2420测试；Current density and lighting voltage: test with Keithley 2420 digital source meter;
功率效率：使用NEWPORT 1931-C测试；Power Efficiency: Tested with NEWPORT 1931-C;
寿命测试：使用LTS-1004AC寿命测试装置。Life Test: Use LTS-1004AC Life Test Device.
实施例1Example 1
中间体A1的制备方法，包括如下步骤：The preparation method of intermediate A1, comprises the steps:
第一步：化合物Int.-1的制备Step 1: Preparation of Compound Int.-1
在氮气保护下，5.0g(37.8mmol)的2-甲氧基苯乙炔溶于50mL的三乙胺中，加入11.2g(45.5mmol)的1-溴二苯并呋喃、760.0mg(4.0mmol)的碘化亚铜、0.9g(4.0mmol)的醋酸钯和2.1g(8.0mmol)的三苯基磷，升温回流搅拌反应6小时，减压浓缩干，用硅胶柱分离纯化，得到中间体Int.-1，收率92％。Under nitrogen protection, 5.0 g (37.8 mmol) of 2-methoxyphenylacetylene was dissolved in 50 mL of triethylamine, 11.2 g (45.5 mmol) of 1-bromodibenzofuran, 760.0 mg (4.0 mmol) were added of cuprous iodide, 0.9 g (4.0 mmol) of palladium acetate and 2.1 g (8.0 mmol) of triphenylphosphine, heated and refluxed for 6 hours, then concentrated to dryness under reduced pressure, and separated and purified with a silica gel column to obtain the intermediate Int .-1, yield 92%.
第二步：化合物Int.-2的制备The second step: preparation of compound Int.-2
在氮气保护下，10.0g(33.5mmol)的中间体Int.-1溶于60mL的二氯甲烷中，加入8.5g(33.5mmol)的碘，于室温搅拌反应20小时，加入20mL的饱和硫代硫酸钠水溶液，分出有机相用1N稀盐酸水洗，水洗，干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到中间体Int.-2，收率89％。Under nitrogen protection, 10.0 g (33.5 mmol) of intermediate Int.-1 was dissolved in 60 mL of dichloromethane, 8.5 g (33.5 mmol) of iodine was added, the reaction was stirred at room temperature for 20 hours, and 20 mL of saturated thiocyanate was added. Sodium sulfate aqueous solution, separate the organic phase and wash with 1N dilute hydrochloric acid, wash with water, dry, filter, concentrate the filtrate to dryness under reduced pressure, and separate and purify by silica gel column to obtain the intermediate Int.-2 with a yield of 89%.
第三步：化合物Int.-3的制备The third step: preparation of compound Int.-3
参照第一步的制备方法，仅将第一步中的2-甲氧基苯乙炔替换为邻硝基苯基乙炔，将1-溴二苯并呋喃替换为中间体Int.-2，制备中间体Int.-3，收率95％。Referring to the preparation method of the first step, only 2-methoxyphenylacetylene in the first step is replaced with o-nitrophenylacetylene, and 1-bromodibenzofuran is replaced with the intermediate Int.-2 to prepare the intermediate Body Int.-3, yield 95%.
第四步：中间体Int.-4的制备The fourth step: the preparation of intermediate Int.-4
在氮气保护下，8.6g(20.0mmol)的中间体Int.-3溶于120mL干燥的甲苯中，加入530.0mg(2.0mmol)的氯化铂，升温回流搅拌反应12小时，减压浓缩干，用硅胶柱分离纯化，得到中间体Int.-4，收率72％。Under nitrogen protection, 8.6 g (20.0 mmol) of the intermediate Int.-3 was dissolved in 120 mL of dry toluene, 530.0 mg (2.0 mmol) of platinum chloride was added, the temperature was raised and refluxed and stirred for 12 hours, and then concentrated to dryness under reduced pressure. It was separated and purified by silica gel column to obtain the intermediate Int.-4 with a yield of 72%.
第五步：中间体A1的制备Step 5: Preparation of Intermediate A1
105.0g(0.4mol)的三苯基磷和43.0g(0.1mol)的中间体Int.-4混合，升温至150℃搅拌反应4小时，冷却到室温，加入200mL的甲苯加热溶解，用硅胶柱分离纯化，得到中间体A1，收率76％。105.0 g (0.4 mol) of triphenylphosphorus was mixed with 43.0 g (0.1 mol) of the intermediate Int.-4, the temperature was raised to 150 °C and the reaction was stirred for 4 hours, cooled to room temperature, and 200 mL of toluene was added to heat and dissolve, and a silica gel column was used. After separation and purification, intermediate A1 was obtained with a yield of 76%.
参照上述的合成方法，制备以下化合物：With reference to the above-mentioned synthetic method, the following compounds were prepared:
实施例2Example 2
化合物CJHL241的制备：Preparation of compound CJHL241:
10.0mmol中间体A5溶解于80mL干燥的THF中，在氮气保护下，用冰水浴降温至0℃，加入11.0mmol的65％氢化钠固体，搅拌反应1小时，加入11.0mmol的2-氯-4,6-二苯基-1,3,5-三嗪(CAS:3842-55-5)，搅拌反应24小时，加入50mL水稀释，用乙酸乙酯萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到化合物CJHL241，白色固体，收率78％，MS(MALDI-TOF)：m/z 629.1991[M+H]
+。
10.0 mmol of intermediate A5 was dissolved in 80 mL of dry THF, and under nitrogen protection, it was cooled to 0 °C with an ice-water bath, 11.0 mmol of 65% sodium hydride solid was added, the reaction was stirred for 1 hour, and 11.0 mmol of 2-chloro-4 was added. ,6-diphenyl-1,3,5-triazine (CAS: 3842-55-5), the reaction was stirred for 24 hours, diluted with 50 mL of water, extracted with ethyl acetate, the organic phase was collected, dried, filtered, and the filtrate was Concentrated to dryness under reduced pressure, separated and purified by silica gel column to obtain compound CJHL241, white solid, yield 78%, MS (MALDI-TOF): m/z 629.1991 [M+H] + .
以上述类似的合成方法，制备以下化合物：The following compounds were prepared in a similar synthetic manner as described above:
实施例3Example 3
化合物CJHL336的制备：Preparation of compound CJHL336:
15.0mmol中间体A1溶解于80mL干燥的甲苯中，在氮气保护下，加入16.5mmol的2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪(CAS:864377-31-1)和22.5mmol的叔丁醇钠，再加入0.1mmol的Pd
2(dba)
3CHCl
3和0.02mL的10％三叔丁磷甲苯溶液，升温至100℃，搅拌反应15小时，冷却到室温，加入50mL水稀释，用乙酸乙酯萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用硅胶柱分离 纯化，得到化合物CJHL336，黄色固体，收率82％，MS(MALDI-TOF)：m/z705.2308[M+H]
+。
15.0 mmol of intermediate A1 was dissolved in 80 mL of dry toluene, and under nitrogen protection, 16.5 mmol of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (CAS) was added. : 864377-31-1) and 22.5 mmol of sodium tert-butoxide, then add 0.1 mmol of Pd 2 (dba) 3 CHCl 3 and 0.02 mL of 10% tri-tert-butylphosphorus toluene solution, warm up to 100 ° C, and stir the reaction for 15 hours, cooled to room temperature, diluted with 50 mL of water, extracted with ethyl acetate, collected the organic phase, dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and separated and purified by silica gel column to obtain compound CJHL336, yellow solid, yield 82%, MS (MALDI-TOF): m/z 705.2308 [M+H] + .
以上述类似的合成方法，制备以下化合物：The following compounds were prepared in a similar synthetic manner as described above:
有机电致发光元件的制备Preparation of Organic Electroluminescent Elements
对比例1Comparative Example 1
将下述的化合物A1和A2的混合物作为绿光主体材料，其中A1和A2的质量比为11:9，使用下述的化合物B作为绿光掺杂材料，化合物C作为孔穴注入材料，化合物D作为空穴传输材料、化合物E作为红光材料，化合物F作为红光掺杂材料，化合物G作为电子传输掺杂材料，LiQ作为电子传输主体材料。The following mixture of compounds A1 and A2 is used as the green light host material, wherein the mass ratio of A1 and A2 is 11:9, the following compound B is used as the green light doping material, the compound C is used as the hole injection material, and the compound D As a hole transport material, compound E is used as a red light material, compound F is used as a red light dopant material, compound G is used as an electron transport dopant material, and LiQ is used as an electron transport host material.
将化合物
依次采用DOV公司制造的EL蒸镀机蒸镀到ITO玻璃上制作绿光元件，制得作为绿光的有机电致发光元件。
compound The green light element was fabricated by successively using an EL vapor deposition machine manufactured by DOV Corporation to vapor-deposit on ITO glass, and an organic electroluminescent element as a green light was fabricated.
将化学式
依次采用DOV公司制造的EL蒸镀机蒸镀到ITO玻璃上制作红光元件，制得作为红光的有机电致发光元件。
chemical formula The red light element was fabricated by successively using an EL vapor deposition machine manufactured by DOV Company to vapor-deposit on the ITO glass, and an organic electroluminescence element as a red light was fabricated.
试验例1Test Example 1
将化合物A替换为本发明的化合物CJHL239～CJHL460，按照对比例1的方法制备绿光有机电致发光元件。Compound A was replaced with compounds CJHL239 to CJHL460 of the present invention, and green light organic electroluminescence elements were prepared according to the method of Comparative Example 1.
所得绿光有机电致发光元件的性能检测结果列于表1中，其中驱动电压(V)、电流效率(LE)、色坐标(CIE)、半峰宽(FWHM)是在元件的电流密度为10mA/cm
2条件下得出，且电压、LE、FWHM和LT90％相较参比元件进行了数据归一化处理。
The performance test results of the obtained green light organic electroluminescent element are listed in Table 1, where the driving voltage (V), current efficiency (LE), color coordinate (CIE), and half-peak width (FWHM) are measured when the current density of the element is 10 mA/cm 2 and data normalized for voltage, LE, FWHM and LT90% compared to the reference element.
表1绿光元件性能检测结果Table 1 Green light component performance test results
由表1可知，本发明的有机材料制备成的绿光元件相较于对比例1制备的元件，驱动电压低，电流效率较高，色纯度好，而且在元件发光亮度初始为2000cd/cm
2为初始的条件下，使用本发明的化合物作为绿光主体材料的元件寿命有很大提高。
As can be seen from Table 1, the green light element prepared from the organic material of the present invention has lower driving voltage, higher current efficiency, and better color purity than the element prepared in Comparative Example 1, and the luminous brightness of the element is initially 2000cd/cm 2 . Under the initial conditions, the lifetime of the device using the compound of the present invention as the green host material is greatly improved.
表1中仅列举了部分的CJHL239～CJHL460中部分化合物的性能，其他化合物性能与表中列举的化合物的结构基本一致，由于篇幅有限，不再一一列举。Table 1 only lists the properties of some compounds in CJHL239~CJHL460. The properties of other compounds are basically the same as the structures of the compounds listed in the table. Due to the limited space, they will not be listed one by one.
按照对比例1的方法制备红光元件，其中，将前述的化合物E替换为本发明的化合物CJHL239～CJHL460，除此之外，
/[本发明的化合物
A red light element was prepared according to the method of Comparative Example 1, wherein the aforementioned compound E was replaced by the compounds CJHL239 to CJHL460 of the present invention, in addition, /[Compounds of the present invention
所得元件的性能检测结果列于表2中，其中驱动电压(V)、电流效率(LE)、色坐标(CIE)、半峰宽(FWHM)是在元件的电流密度为10mA/cm
2条件下得出，且电压、LE、FWHM和LT90％相较参比元件进行了数据归一化处理。
The performance test results of the obtained components are listed in Table 2, in which the driving voltage (V), current efficiency (LE), color coordinates (CIE), and half-peak width (FWHM) are obtained under the condition that the current density of the component is 10 mA/cm 2 Resulting and data normalized for voltage, LE, FWHM and LT90% compared to the reference element.
表2红光元件性能检测结果Table 2 The performance test results of red light components
由表2的红光元件性能测试结果可知，本发明的有机材料制备成的元件相较于对比例1制备的红光元件驱动电压明显降低，电流效率高，发光色纯度好。在元件初始亮度为2000cd/cm
2为初始的条件下，使用本发明的化合物作为红光主体材料的元件LT90％寿命是对比元件1.1倍至2.7倍。
It can be seen from the performance test results of the red light element in Table 2 that the element prepared from the organic material of the present invention has significantly lower driving voltage, higher current efficiency and better luminous color purity than that of the red light element prepared in Comparative Example 1. Under the condition that the initial brightness of the element is 2000cd/cm 2 , the LT90% lifetime of the element using the compound of the present invention as the red light host material is 1.1 to 2.7 times that of the comparative element.
表2中仅列举了部分的CJHL239～CJHL460中部分化合物的性能，其他化合物性能与表中列举的化合物的结构基本一致，由于篇幅有限，不再一一列举。Table 2 only lists the properties of some compounds in CJHL239~CJHL460. The properties of other compounds are basically the same as the structures of the compounds listed in the table. Due to the limited space, they will not be listed one by one.
如图1和2所示，分别为本发明的有机电致发光装置的一个底部发光例子的示意图和有机电致发光装置的一个顶部发光例子的示意图，本发明制备的咔唑衍生物包含在发光层5中。1 and 2 are respectively a schematic diagram of a bottom emission example of the organic electroluminescence device of the present invention and a schematic diagram of a top emission example of the organic electroluminescence device, the carbazole derivatives prepared by the present invention are included in the luminescence in layer 5.
以上所述，仅为本发明的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，可轻易想到变化或替换，都应涵盖在本发明的保护范围之内。因此，本发明的保护范围应以所述权利要求的保护范围为准。The above are only specific embodiments of the present invention, but the protection scope of the present invention is not limited thereto. Any person skilled in the art can easily think of changes or substitutions within the technical scope disclosed by the present invention. should be included within the protection scope of the present invention. Therefore, the protection scope of the present invention should be based on the protection scope of the claims.
Claims (10)
- 一种咔唑衍生物，其特征在于，所述咔唑衍生物的结构如式(I)所示：A carbazole derivative, characterized in that the structure of the carbazole derivative is shown in formula (I):
其中，任意两个相邻的基团W 1、W 2、W 3、W 4代表下式(II)的基团， Wherein, any two adjacent groups W 1 , W 2 , W 3 , W 4 represent groups of the following formula (II),
其中，Z在每次出现时相同或不同地代表CR 9或N，并且^指示式I中的相应的相邻基团W 1和W 2、W 2和W 3或W 3和W 4； wherein Z represents, identically or differently, CR or N at each occurrence, and ^ indicates the corresponding adjacent groups W and W, W and W , or W and W in formula I ;T 1、T 2表示O、S、NAr 2或CR 10R 11； T 1 , T 2 represent O, S, NAr 2 or CR 10 R 11 ;R 1～R 11相同或者不同，选自氢、氘、具有C 1～C 40的直链烷基、具有C 1～C 40的直链杂烷基、具有C 3～C 40的支链或环状的烷基、具有C 3～C 40的支链或环状的杂烷基、具有C 2～C 40的烯基或炔基、具有5～60个碳原子的芳香族环系或杂芳族环系中的一种，R 1～R 11中的每个基团可被一个或多个基团R取代，且其中两个或更多个相邻的取代基团可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系； R 1 to R 11 are the same or different, and are selected from hydrogen, deuterium, straight-chain alkyl having C 1 -C 40 , straight-chain heteroalkyl having C 1 -C 40 , branched chain having C 3 -C 40 or Cyclic alkyl, branched or cyclic heteroalkyl with C3 - C40 , alkenyl or alkynyl with C2 - C40 , aromatic ring system or heteroalkyl with 5-60 carbon atoms An aromatic ring system in which each of R 1 to R 11 may be substituted with one or more groups R, and in which two or more adjacent substituted groups may be optionally joined or fused to form monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems;Ar 1、Ar 2相同或者不同，选自具有C 1～C 40的直链烷基、具有C 1～C 40的直链杂烷基、具有C 3～C 40的支链或环状的烷基、具有C 3～C 40的支链或环状的杂烷基、具有C 2～C 40的烯基或炔基、具有5～60个碳原子的芳香族环系或杂芳族环系，所述环系可被一个或多个基团R取代； Ar 1 and Ar 2 are the same or different, and are selected from linear alkyl groups with C 1 to C 40 , linear heteroalkyl groups with C 1 to C 40 , branched or cyclic alkanes with C 3 to C 40 group, branched or cyclic heteroalkyl group with C3 - C40 , alkenyl or alkynyl group with C2 - C40 , aromatic ring system or heteroaromatic ring system with 5-60 carbon atoms , the ring system may be substituted by one or more groups R;所述R每次出现时相同或不同，选自氢原子、氘原子、卤素原子、腈基、 硝基、N(Ar 3) 2、N(R 12) 2、C(＝O)Ar 3、C(＝O)R 12、P(＝O)(Ar 3) 2、具有C 1～C 40的直链烷基、具有C 1～C 40的直链杂烷基、具有C 3～C 40的支链或环状的烷基、具有C 3～C 40的支链或环状的杂烷基、具有C 2～C 40的烯基或炔基、具有5～80个碳原子的芳族环或杂芳族环系、具有5～60个碳原子的芳氧基或杂芳氧基中的一种，R基团中的每个基团可被一个或多个基团R 12取代，或这些体系的组合，其中一个或多个非相邻的-CH 2-基团可被R 12C＝CR 12、C≡C、Si(R 12) 2、Ge(R 12) 2、Sn(R 12) 2、C＝O、C＝S、C＝Se、C＝NR 12、P(＝O)(R 12)、SO、SO 2、NR 12、O、S或CONR 12代替，并且其中一个或多个氢原子或被氘原子、卤素原子、腈基或硝基代替，其中两个或更多个相邻的取代基R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系，所述环系可被一个或多个基团R 12取代； Said R is the same or different at each occurrence, and is selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, nitro group, N(Ar 3 ) 2 , N(R 12 ) 2 , C(=O)Ar 3 , C(=O)R 12 , P(=O)(Ar 3 ) 2 , straight-chain alkyl having C 1 -C 40 , straight-chain heteroalkyl having C 1 -C 40 , C 3 -C 40 branched or cyclic alkyl groups, branched or cyclic heteroalkyl groups with C 3 -C 40 , alkenyl or alkynyl groups with C 2 -C 40 , aromatic groups with 5 to 80 carbon atoms one of a ring or heteroaromatic ring system, an aryloxy or heteroaryloxy group having 5 to 60 carbon atoms, each of the R groups may be substituted by one or more groups R 12 , or a combination of these systems in which one or more non-adjacent -CH 2 - groups may be replaced by R 12 C=CR 12 , C≡C, Si(R 12 ) 2 , Ge(R 12 ) 2 , Sn( R 12 ) 2 , C=O, C=S, C=Se, C=NR 12 , P(=O)(R 12 ), SO, SO 2 , NR 12 , O, S or CONR 12 instead, and wherein One or more hydrogen atoms are either replaced by deuterium atoms, halogen atoms, nitrile or nitro groups, wherein two or more adjacent substituents R can be optionally joined or fused to form monocyclic or polycyclic aliphatic an aromatic, aromatic or heteroaromatic ring system, which may be substituted by one or more groups R 12 ;R 12每次出现时相同或不同，选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar 3) 2、N(R 13) 2、C(＝O)Ar 3、C(＝O)R 13、P(＝O)(Ar 3) 2、具有C 1～C 40的直链烷基、具有C 1～C 40的直链杂烷基、具有C 3～C 40的支链或环状的烷基、具有C 3～C 40的支链或环状的杂烷基、具有C 2～C 40的烯基或炔基、具有5～60个碳原子的芳族环或杂芳族环系、具有5～60个碳原子的芳氧基或杂芳氧基中的一种，R 12中的每个基团可被一个或多个基团R 13取代，或这些体系的组合，其中一个或多个非相邻的-CH 2-基团可被R 13C＝CR 13、C≡C、Si(R 13) 2、Ge(R 13) 2、Sn(R 13) 2、C＝O、C＝S、C＝Se、C＝NR 13、P(＝O)(R 13)、SO、SO 2、NR 13、O、S或CONR 13代替，并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替，其中两个或更多个相邻的取代基R 12可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系，所述环系可被一个或多个基团R 13取代； R 12 is the same or different at each occurrence and is selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, nitro group, N(Ar 3 ) 2 , N(R 13 ) 2 , C(=O)Ar 3 , C (=O)R 13 , P(=O)(Ar 3 ) 2 , straight-chain alkyl having C 1 -C 40 , straight-chain heteroalkyl having C 1 -C 40 , straight-chain heteroalkyl having C 3 -C 40 Branched or cyclic alkyl, branched or cyclic heteroalkyl with C3 - C40 , alkenyl or alkynyl with C2 - C40 , aromatic ring with 5-60 carbon atoms or one of heteroaromatic ring systems, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, each group in R 12 may be substituted with one or more groups R 13 , or these Combinations of systems in which one or more non-adjacent -CH2- groups can be replaced by R13C = CR13 , C≡C, Si( R13 ) 2 , Ge( R13 ) 2 , Sn( R13 ) 2 , C=O, C=S, C=Se, C=NR 13 , P(=O)(R 13 ), SO, SO 2 , NR 13 , O, S or CONR 13 instead, and either or Multiple hydrogen atoms can be replaced by deuterium atoms, halogen atoms, nitrile or nitro groups, wherein two or more adjacent substituents R 12 can be optionally joined or fused to form a monocyclic or polycyclic aliphatic , aromatic or heteroaromatic ring systems, which may be substituted by one or more groups R 13 ;Ar 3在每次出现时相同或不同，选自具有5～30个碳原子的芳族或杂芳族环系，所述环系可被一个或多个非芳族基团R 13取代；此处键合至同一氮原子或磷原子的两个基团Ar 3也可通过单键或选自N(R 13)、C(R 13) 2、氧或硫的桥连基彼此桥连； Ar 3 is the same or different at each occurrence and is selected from aromatic or heteroaromatic ring systems having 5 to 30 carbon atoms, which may be substituted by one or more non-aromatic groups R 13 ; this The two groups Ar 3 bound to the same nitrogen or phosphorus atom can also be bridged to each other by a single bond or a bridging group selected from N(R 13 ), C(R 13 ) 2 , oxygen or sulfur;R 13选自氢原子、氘原子、氟原子、腈基、具有C 1～C 20的脂族烃基、具有 5～30个碳原子的芳族环或杂芳族环系，其中R 13中一个或多个氢原子可被氘原子、卤素原子、或腈基代替，其中两个或更多个相邻的取代基R 13可彼此形成单环或多环的脂族、芳族或杂芳族环系。 R 13 is selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, aliphatic hydrocarbon group with C 1 -C 20 , aromatic ring or heteroaromatic ring system with 5-30 carbon atoms, wherein one of R 13 or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R 13 may form with each other a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic Ring system. - 根据权利要求1所述的咔唑衍生物，其特征在于，所述式(I)包括以下式(I)-A～式(I)-F所示的结构：The carbazole derivative according to claim 1, wherein the formula (I) comprises the structures represented by the following formulas (I)-A to (I)-F:
其中R 1～R 8、T 1、T 2、Ar 1和R的定义与权利要求1的定义相同。 The definitions of R 1 to R 8 , T 1 , T 2 , Ar 1 and R are the same as those of claim 1 . - 根据权利要求1或2所述的咔唑衍生物，其特征在于，所述R 1～R 8相同或者不同，选自氢、氘、具有5～60个碳原子的芳香族环系或杂芳族环系，其中每个基团可被一个或多个基团R取代，其中两个或更多个相邻的取代基团可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系； The carbazole derivative according to claim 1 or 2, wherein the R 1 to R 8 are the same or different, and are selected from hydrogen, deuterium, an aromatic ring system having 5 to 60 carbon atoms or a heteroaromatic aliphatic ring systems in which each group may be substituted with one or more groups R, in which two or more adjacent substituted groups may be optionally joined or fused to form a monocyclic or polycyclic aliphatic , aromatic or heteroaromatic ring systems;T 1、T 2表示O或S； T 1 , T 2 represent O or S;所述Ar 1选自具有5～60个碳原子的芳香族环系或杂芳族环系，所述环系可被一个或多个基团R取代。 The Ar 1 is selected from an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, and the ring system may be substituted by one or more groups R.
- 根据权利要求1～3任一项所述的咔唑衍生物，其特征在于，所述咔唑衍生物包括以下CJHL239～CJHL460所示的结构：The carbazole derivative according to any one of claims 1 to 3, wherein the carbazole derivative comprises the following structures shown in CJHL239 to CJHL460:
- 一种权利要求1～4任意一项所述的咔唑衍生物在有机元件用材料中的应用。A use of the carbazole derivative according to any one of claims 1 to 4 in a material for organic elements.
- 根据权利要求5所述的应用，其特征在于，所述的咔唑衍生物为有机电致发光元件用材料、有机场效应晶体管用材料或有机薄膜太阳能电池用材料。The application according to claim 5, wherein the carbazole derivatives are materials for organic electroluminescence elements, materials for organic field effect transistors or materials for organic thin film solar cells.
- 根据权利要求6所述的应用，其特征在于，所述的咔唑衍生物在发光层材料、空穴输送/空穴阻挡层材料或封装层材料中的应用。The application according to claim 6, wherein the carbazole derivative is used in a light-emitting layer material, a hole transport/hole blocking layer material or an encapsulation layer material.
- 一种有机电致发光元件，其特征在于，包括第一电极、第二电极和位于第一电极和第二电极之间的多层有机层，所述有机层中的至少一层包含权利要求1～4任意一项所述的咔唑衍生物。An organic electroluminescence element, characterized in that it comprises a first electrode, a second electrode and a multilayer organic layer between the first electrode and the second electrode, at least one of the organic layers comprising claim 1 The carbazole derivative according to any one of ~4.
- 一种显示装置，其特征在于，包括权利要求8所述的有机电致发光元件。A display device comprising the organic electroluminescence element according to claim 8 .
- 一种照明装置，其特征在于，包括权利要求8所述的有机电致发光元件。A lighting device, comprising the organic electroluminescence element according to claim 8 .
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110383584.5 | 2021-04-09 | ||
| CN202110383584.5A CN113072560B (en) | 2021-04-09 | 2021-04-09 | Carbazole derivative and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2022213854A1 true WO2022213854A1 (en) | 2022-10-13 |
Family
ID=76615818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2022/083968 WO2022213854A1 (en) | 2021-04-09 | 2022-03-30 | Carbazole derivative and use thereof |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN113072560B (en) |
| WO (1) | WO2022213854A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113072560B (en) * | 2021-04-09 | 2023-11-24 | 北京八亿时空液晶科技股份有限公司 | Carbazole derivative and application thereof |
| CN113264944B (en) * | 2021-05-14 | 2022-11-29 | 北京八亿时空液晶科技股份有限公司 | Organic compound, organic electroluminescent material and device thereof |
| CN114591328B (en) * | 2022-02-28 | 2023-06-13 | 上海八亿时空先进材料有限公司 | Carbazole derivative and application thereof |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103842339A (en) * | 2011-09-21 | 2014-06-04 | 默克专利有限公司 | Carbazole derivatives for organic electroluminescence devices |
| CN106661007A (en) * | 2014-08-13 | 2017-05-10 | 默克专利有限公司 | Materials for organic electroluminescent devices |
| CN107428774A (en) * | 2015-04-16 | 2017-12-01 | Sfc株式会社 | Novel heterocyclic compounds and the organic illuminating element including the compound |
| CN108440537A (en) * | 2018-04-18 | 2018-08-24 | 石家庄诚志永华显示材料有限公司 | Carbazole derivates, material and organic electroluminescence device comprising the carbazole derivates |
| CN108699058A (en) * | 2015-12-21 | 2018-10-23 | 出光兴产株式会社 | Heterofused phenylquinazolines and their use in electronic devices |
| CN109689655A (en) * | 2016-09-14 | 2019-04-26 | 默克专利有限公司 | Compound with carbazole structure |
| WO2019124902A1 (en) * | 2017-12-18 | 2019-06-27 | 덕산네오룩스 주식회사 | Organic electronic element using organic electronic element compound, and electronic device therefor |
| CN110698458A (en) * | 2019-10-30 | 2020-01-17 | 烟台显华化工科技有限公司 | Organic luminescent material and application thereof |
| WO2020099307A1 (en) * | 2018-11-15 | 2020-05-22 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| CN113072560A (en) * | 2021-04-09 | 2021-07-06 | 北京八亿时空液晶科技股份有限公司 | Carbazole derivative and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018021406A1 (en) * | 2016-07-29 | 2018-02-01 | 大電株式会社 | Metal complex and electron-transporting material using same |
-
2021
- 2021-04-09 CN CN202110383584.5A patent/CN113072560B/en active Active
-
2022
- 2022-03-30 WO PCT/CN2022/083968 patent/WO2022213854A1/en active Application Filing
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103842339A (en) * | 2011-09-21 | 2014-06-04 | 默克专利有限公司 | Carbazole derivatives for organic electroluminescence devices |
| CN106661007A (en) * | 2014-08-13 | 2017-05-10 | 默克专利有限公司 | Materials for organic electroluminescent devices |
| CN107428774A (en) * | 2015-04-16 | 2017-12-01 | Sfc株式会社 | Novel heterocyclic compounds and the organic illuminating element including the compound |
| CN108699058A (en) * | 2015-12-21 | 2018-10-23 | 出光兴产株式会社 | Heterofused phenylquinazolines and their use in electronic devices |
| CN109689655A (en) * | 2016-09-14 | 2019-04-26 | 默克专利有限公司 | Compound with carbazole structure |
| WO2019124902A1 (en) * | 2017-12-18 | 2019-06-27 | 덕산네오룩스 주식회사 | Organic electronic element using organic electronic element compound, and electronic device therefor |
| CN108440537A (en) * | 2018-04-18 | 2018-08-24 | 石家庄诚志永华显示材料有限公司 | Carbazole derivates, material and organic electroluminescence device comprising the carbazole derivates |
| WO2020099307A1 (en) * | 2018-11-15 | 2020-05-22 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| CN110698458A (en) * | 2019-10-30 | 2020-01-17 | 烟台显华化工科技有限公司 | Organic luminescent material and application thereof |
| CN113072560A (en) * | 2021-04-09 | 2021-07-06 | 北京八亿时空液晶科技股份有限公司 | Carbazole derivative and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113072560A (en) | 2021-07-06 |
| CN113072560B (en) | 2023-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7221283B2 (en) | Materials for organic electroluminescence devices | |
| JP5980796B2 (en) | Materials for organic electroluminescent devices | |
| WO2022088910A1 (en) | Carbazole derivative and application thereof | |
| CN112442041B (en) | Carbazole derivative and application thereof | |
| CN112480128B (en) | Carbazole derivative and application thereof | |
| WO2022213854A1 (en) | Carbazole derivative and use thereof | |
| CN111909158B (en) | Carbazole derivative and application thereof | |
| WO2023160187A1 (en) | Carbazole derivative and use thereof | |
| WO2022257584A1 (en) | Compound, organic electroluminescence device containing same, and electronic device | |
| CN112480136B (en) | Heteroatom-bridged carbazole derivatives and uses thereof | |
| CN112375082B (en) | Series carbazole derivative and application thereof | |
| CN112707904A (en) | Naphthalene bisindole derivative and application thereof | |
| WO2022088911A1 (en) | Benzophenanthrene derivative and application thereof | |
| CN112778307B (en) | Carbazole derivative and application thereof | |
| CN112442046B (en) | Naphthalene bridged carbazole derivative and application thereof | |
| WO2022199464A1 (en) | Carbazole derivative and application thereof, organic electroluminescent element, display device, and lighting device | |
| CN113563312B (en) | Pyrrole derivative, organic electroluminescent material, light-emitting element and consumer product | |
| CN113354641B (en) | Organic compound and application thereof | |
| CN113563344B (en) | Carbazole derivative, organic electroluminescent material, light-emitting element, and consumer product | |
| CN112521343B (en) | Organic electroluminescent material and device thereof | |
| CN114349798A (en) | Metal complex, application and consumer product | |
| CN114276366A (en) | Indole derivative and application thereof | |
| CN112812086B (en) | Auxiliary ligands for organometallic complexes, devices and formulations comprising the same | |
| CN113061150B (en) | Phosphorus-containing organic compound and application thereof | |
| CN112521340B (en) | Organic electroluminescent material and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22783921 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 22783921 Country of ref document: EP Kind code of ref document: A1 |