CN115073461A - 一种咔唑衍生物及其在有机发光元件中的应用 - Google Patents
一种咔唑衍生物及其在有机发光元件中的应用 Download PDFInfo
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- CN115073461A CN115073461A CN202210823584.7A CN202210823584A CN115073461A CN 115073461 A CN115073461 A CN 115073461A CN 202210823584 A CN202210823584 A CN 202210823584A CN 115073461 A CN115073461 A CN 115073461A
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- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract description 3
- 239000000463 material Substances 0.000 claims abstract description 33
- 150000001716 carbazoles Chemical class 0.000 claims abstract description 30
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000010410 layer Substances 0.000 claims description 136
- -1 nitro, carboxyl Chemical group 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 238000002347 injection Methods 0.000 claims description 26
- 239000007924 injection Substances 0.000 claims description 26
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 230000005525 hole transport Effects 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 9
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 8
- 239000010452 phosphate Substances 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 150000007942 carboxylates Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000004832 aryl thioethers Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- MWPCBCGAQVXDCZ-UHFFFAOYSA-N 1-amino-1-nitramidoguanidine Chemical compound [N+](=O)([O-])NN(C(N)=N)N MWPCBCGAQVXDCZ-UHFFFAOYSA-N 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 4
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 150000007857 hydrazones Chemical class 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 4
- 229950000688 phenothiazine Drugs 0.000 claims description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 2
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims 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 claims description 2
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 claims description 2
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 claims description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 claims description 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 claims description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 2
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- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 2
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical compound C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 2
- 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 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005361 aryl sulfoxide group Chemical group 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052796 boron Inorganic materials 0.000 claims description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 2
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
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- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 2
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- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
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- QQTOBDXDQYCGMA-UHFFFAOYSA-N naphtho[2,3-e][1,3]benzoxazole Chemical compound C1=CC=C2C=C3C(N=CO4)=C4C=CC3=CC2=C1 QQTOBDXDQYCGMA-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
本发明涉及一种咔唑衍生物及其在有机发光元件中的应用。所述咔唑衍生物具有稠合的咔唑结构，具有高三线态能级，增大了咔唑母核的共轭，从而提高了材料热稳定性和输送载流子的能力。将所述咔唑衍生物应用在有机电致发光元件中，可显著降低驱动电压并提高发光效率和寿命。所述咔唑衍生物的结构式如式(I)所示。
Description
技术领域
本发明涉及有机电致发光材料技术领域，尤其涉及一种咔唑衍生物及其在有机发光元件中的应用。
背景技术
一般而言，有机发光现象是指在对有机物质施加电能时发出光的现象。即在阳极与阴极之间配置有机层时，如果在两个电极之间施加电压，则空穴会从阳极注入至有机层，电子会从阴极注入至有机层，当所注入的空穴和电子相遇时，会形成激子，当该激子跃迁至基态时，会发出光和热。
最近几年有机电致发光显示技术已趋于成熟，一些产品已进入市场，但在产业化过程中，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，其载流子注入和传输性能、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；尤其是发光元件的发光效率和使用寿命还达不到实用化要求，这大大限制了有机发光二极管(OrganicLight-ECitting Diode，简称OLED)技术的发展。而利用三线态发光的金属配合物磷光材料具有高的发光效率，其绿光和红光材料已经达到使用要求，但是金属配合物磷光材料要求具有高三线态能级的磷光材料或空穴材料与之匹配。因此，开发具有高三线态能级的磷光材料或空穴材料是当前OLED发展的迫切需求。
在目前的技术发展下，无论是对于荧光材料还是对于磷光材料，特别是在用于有机电致发光元件中的工作电压、效率和寿命方面和在升华期间的热稳定性方面，都还需要改进。
鉴于此，特提出本发明。
发明内容
为了克服如上所述的以往技术问题而进一步提高有机电致发光元件的特性，继续要求对于在有机电致发光元件中可用作磷光材料或空穴材料的更加稳定且有效的物质的开发。
需要强调的是，本发明中，“取代或未取代的”是指：被选自氢、氘、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷基、C3-C60环烯基、C6-C60芳基、C6-C60芳氧基、C6-C60芳硫醚基和C2-C60杂环芳基中的1个以上的取代基取代或未取代，或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代或未取代。
需要强调的是，本发明中，“
”表示Ar1与L1或N的连接键；“*—”和“—*”表示连接键。
本发明的方案在于提供一种咔唑衍生物，所述咔唑衍生物可提高材料热稳定性和输送载流子的能力，利用该化合物制备的有机电致发光元件，可显著降低驱动电压、提高发光效率和寿命。
所述咔唑衍生物的结构式如式(I)所示：
其中，
L1选自单键、取代或未取代的C6-C60亚芳基、或者取代或未取代的C2-C60杂亚芳基；
X1、X2、X3各自独立地为N或CR7；
R1、R2、R3、R4、R5、R6、R7相同或不同的选自由氢、氘、氟、羟基、腈基、硝基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C1-C40烷氧基、C2-C40烯基、C1-C40烷硫基、C1-C40烷氧基、C3-C40环烷基、C1-C40烷基亚砜基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫基、取代或未取代的C6-C60芳基亚砜基、取代或未取代的C3-C40甲硅烷基、取代或未取代的硼基、取代或未取代的胺基、取代或未取代的芳基膦基、取代或未取代的氧化膦基、或者取代或未取代的C2-C60杂环芳基组成的群组；
n表示0-5的整数；
Ar1选自由取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、或者取代或未取代的C2-C60杂环芳基组成的群组。
优选地，所述X1、X2、X3各自独立地为CR7；
所述n为0、1或2；
所述R1、R2、R3、R4、R5、R6、R7各自独立地选自由氢、氘、氟、腈基、苯基、二联苯基、三联苯基、萘基、菲基、三亚苯基、咔唑、二苯并呋喃或二苯并噻吩组成的群组；
所述Ar1选自如下物质的基团：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、四联苯、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、喹唑啉和苯并噻二唑或者衍生自这些体系的组合的基团。
优选地，所述Ar1选自由以下II-1～II-17所示基团组成的群组：
其中，
Z1、Z2各自独立地选自由氢、氘、卤素、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基组成的群组；
x1表示1-4的整数；x2表示1-3的整数；x3表示1或2；x4表示1-6的整数；x5表示1-5的整数；
T1表示O、S、CR’R”或NAr’；
R’、R”各自独立地选自由氢、氘、C1～C40的烷基、C1～C40的杂烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组，R’和R”可任选地接合或稠合形成另外的一个多个取代或未取代的环，在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S；更优选地，R’、R”为甲基、苯基或芴基；
Ar’选自由C1～C40的烷基、C1～C40的杂烷基、C3～C40的环烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组；更优选地，Ar’为甲基、乙基、苯基、联苯基或萘基。
优选地，所述L1选自由以下III-1～III-15所示基团组成的群组：
其中，
Z11、Z12各自独立地选自由氢、氘氢、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基组成的群组；
Z13表示取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基中的一种或多种；
y1表示1-4的整数；y2表示1-6的整数；y3表示1-3的整数；y4表示1-5的整数；
T3表示O或S。
优选地，所述咔唑衍生物选自如下式C470-C625所示的化合物：
其中，*—G—*选自*—O—*、*—S—*或下述结构中的一种：
基于相同的技术构思，本发明再提供一种所述咔唑衍生物的制备方法，如方案1所示：
方案1：
在方案1中，所用符号如式(I)中所定义，并且Y1、Y2、Y3、Y4各自独立地选自Cl、Br、I或OTf；
合成式(I)所示咔唑衍生物的原料可通过商业途径购买而得，此方法原理、操作过程、常规后处理、过柱纯化、重结晶提纯等手段是本领域合成从员所熟知的，完全可以实现合成过程，目标产物是理论及实践均可获得的。
具体地，式(I)的咔唑衍生物是由3-R1取代的-5-卤代的咔唑I-0与R2基乙炔进行取代反应，制备中间体I-1；中间体I-1进行关环反应制备中间体I-2；咔唑中间体I-2进行卤化反应获得I-3；多卤代中间体I-3与咔唑或咔啉进行偶联反应制备本发明的母核化合物I-4；化合物I-4与Ar1-(L1)n-Y4进行偶联反应制备化合物式(I)。中间体Ar1-(L1)n-Y4可通过钯催化或碱催化偶联反应制备。
作为可用于钯催化偶联反应的钯催化剂可选自：Pd(P-tBu3)2、Pd(PPh3)4、Pd2(dba)3、Pd2(dba)3CHCl3、PdCl2(PPh3)2、PdCl2(CH3CN)2、Pd(OAc)2、Pd(acac)2、Pd/C、PdCl2、[Pd(allyl)Cl]2等任意一种，或使用两种以上的混合物。
此外，钯催化的偶联反应或碱催化的偶联反应使用的碱可选自：叔丁醇钠、叔丁醇钾、氢化钠、氢化锂、叔戊醇钠、乙醇钠、甲醇钠、碳酸钠、碳酸钾、碳酸铯、锂、氢化钾、三乙胺、氟化铯等任意一种，或使用两种以上的混合物。
偶联反应可以在有机溶剂中进行，其中有机溶剂可选自：乙醚、四氢呋喃、2-甲基四氢呋喃、1,4-二氧六环、乙二醇乙醚、乙二醇二乙醚、乙二醇甲醚、二甘醇二乙醚、或苯甲醚等醚类溶剂、苯、甲苯、二甲苯等芳烃类剂、氯苯、二氯苯、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、二甲基亚砜、环丁砜等，可以使用一种或两种以上的混合物。
本发明还提供一种有机电致发光材料，其原料包含所述的咔唑衍生物；且包含本发明的化合物的有机电致发光材料具有载流子传输的能力。
本发明还提供一种有机电致发光材料在制备有机电致发光元件中的应用。
本发明还提供一种有机电致发光元件，其包括：第一电极、第二电极、封盖层和置于所述第一电极、所述第二电极之间的一层以上的有机层；所述有机层或封盖层中的至少一层的材料包括以上所述的咔唑衍生物。
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所述的咔唑衍生物。
进一步地，根据本发明的有机电致发光元件不包含单独的空穴注入层和/或空穴传输层和/或空穴阻挡层和/或电子传输层，即发光层与电子阻挡层或空穴传输层或阳极直接相邻，和/或发光层与电子传输层或电子注入层或阴极直接相邻。
在根据本发明的有机电致发光元件的其它层中，特别是在空穴注入和空穴传输层中以及在电子注入和电子传输层中，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。
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。
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。
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。
这些方法是本领域普通技术人员通常已知的，并且他们可以在不付出创造性劳动的情况下将其应用于包含根据本发明的化合物的有机电致发光元件。
因此，本发明还涉及制造根据本发明的有机电致发光元件的方法，借助于升华方法来施加至少一个层，和/或特征在于借助于有机气相沉积方法或借助于载气升华来施加至少一个层，和/或特征在于从溶液中通过旋涂或借助于印刷方法来施加至少一个层。
此外，本发明涉及包含至少一种上文指出的本发明的咔唑衍生物。如上文关于有机电致发光元件指出的相同优选情况适用于所述本发明的化合物。特别是，所述化合物此外还可优选包含其它化合物。从液相处理根据本发明的化合物，例如通过旋涂或通过印刷方法进行处理，需要根据本发明的化合物的制剂。这些制剂可以例如是溶液、分散体或乳液。出于这个目的，可优选使用两种或更多种溶剂的混合物。合适并且优选的溶剂例如是甲苯、苯甲醚、邻二甲苯、间二甲苯或对二甲苯、苯甲酸甲酯、均三甲苯、萘满、邻二甲氧基苯、四氢呋喃、甲基四氢呋喃、四氢吡喃、氯苯、二噁烷、苯氧基甲苯，特别是3-苯氧基甲苯、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯烷酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、异丙苯、环己醇、环己酮、环己基苯、十氢化萘、十二烷基苯、苯甲酸乙酯、茚满、苯甲酸甲酯、1-甲基吡咯烷酮、对甲基异丙基苯、苯乙醚、1,4-二异丙基苯、二苄醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇单丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-异丙基萘、戊苯、己苯、庚苯、辛苯、1,1-双(3,4-二甲基苯基)乙烷，或这些溶剂的混合物。
作为优选，所述有机层包括空穴注入层、空穴传输层、空穴阻挡层、发光层、电子传输层、电子注入层或电子阻挡层。
本发明同时提供一种消费型产品，其包括以上所述的有机电致发光元件。
另外，如无特殊说明，本发明中所用原料均可通过市售商购获得，本发明所记载的任何范围包括端值以及端值之间的任何数值以及端值或者端值之间的任意数值所构成的任意子范围。
本发明的有益效果为：
本发明所述的咔唑衍生物(式(I)所示)，具有高三线态能级，增大了咔唑母核的共轭，提高了材料热稳定性和输送载流子的能力，将所述咔唑衍生物应用在有机电致发光元件中，可显著降低驱动电压、并提高发光效率和寿命。
附图说明
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。
图1展示有机发光装置100示意图。图示不一定按比例绘制。装置100可包含衬底101、阳极102、空穴注入层103、空穴传输层104、电子阻挡层105、发光层106、空穴阻挡层107、电子传输层108、电子注入层109、阴极110以及封盖层(CPL)111。装置100可通过依序沉积所描述的层来制造。
图2展示两个发光层的有机发光装置200示意图。所述装置包含衬底201、阳极202、空穴注入203、空穴传输层204、第一发光层205、电子传输层206、电荷产生层207、空穴注入层208、空穴传输层209、第二发光层210、电子传输层211、电子注入层212以及阴极213。可通过依序沉积所描述的层来制备装置200。因为最常见的OLED装置具有一个发光层，而装置200具有第一发光层和第二发光层，第一发光层和第二发光层的发光峰形可以是重叠的或交叉重叠的或非重叠的。在装置200的对应层中，可使用与关于装置100所描述的材料类似的材料。图2提供可如何从装置100的结构增加一些层的一个实例。
具体实施方式
以下实施例用于说明本发明，但不用来限制本发明的范围。
在本发明的描述中，除非另有说明，“多个”的含义是两个或两个以上；术语“上”、“下”等指示的方位或位置关系为基于附图所示的方位或位置关系，仅是为了便于描述本发明和简化描述，而不是指示或暗示所指的装置或元件必须具有特定的方位、以特定的方位构造和操作，因此不能理解为对本发明的限制。
以下实施例中所使用的实验方法如无特殊说明，均为常规方法。以下实施例中所用的实验原料和相关设备等，如无特殊说明，均可从商业途径得到，所述百分比如无特殊说明，均为质量百分比。
下述实施例对OLED材料及元件进行性能测试的测试仪器及方法如下：
OLED元件性能检测条件：
亮度和色度坐标：使用光谱扫描仪PhotoResearch PR-715测试；
电流密度和起亮电压：使用数字源表Keithley 2420测试；
功率效率：使用NEWPORT 1931-C测试。
实施例1
化合物C483的制备方法，包括如下步骤：
第一步：中间体Int-1的制备
20.0mmol的5-溴-3-氯咔唑(反应物1)溶解于40mL的甲苯和20mL的三乙胺中，在氮气保护下，加入22.0mmol的三甲基硅基乙炔(反应物2)、4.0mmol的碘化亚铜、2.0mmol的PdCl2(PPh3)2，升温回流反应24小时，降至室温，减压浓缩干，残余物用硅胶柱分离纯化，得到化合物Int-1，白色固体，收率42％。
第二步：中间体Int-2的制备
在氮气保护下，20.0mmol的Int-1溶解于80mL的硝基甲烷和20mL的THF中，加入60.0mmol的溴化铜、10.0mmol的无水磷酸钾，于室温搅拌反应12小时，加入20mL的浓盐酸和20mL的二氯甲烷搅拌反应1小时，分出有机相，干燥，过滤，减压浓缩干，残余物用硅胶柱分离纯化，得到化合物Int-2，白色固体，收率84％。
化合物B-1的制备
参照上述类似的合成方法，仅将第一步中的三甲基硅基乙炔替换为芳基乙炔或烷基乙炔等取代的乙炔，例如，苯基乙炔，制备化合物B-1。
化合物B-2的制备
参照上述类似的合成方法，仅将第一步中的三甲基硅基乙炔替换为3-吡啶乙炔，制备化合物B-2。
第三步：中间体Int-3的制备
在氮气保护下，20.0mmol的Int-2溶解于50mL的DMF中，分批加入21.0mmol的NCS，搅拌反应12小时，将反应液倒入150mL的冰水中，过滤，滤饼用水洗、饱和亚硫酸氢钠水溶液洗，硅胶柱分离纯化，得到白色固体Int-3，收率94％。
第四步：中间体Int-4的制备
在氮气保护下，10.0mmol的Int-3溶解于60mL的二甲苯中，加入12.0mmol的咔唑、25.0mmol的无水碳酸钾、1.0mmol的碘化亚铜和2.5mmol的N,N’-二甲基乙二胺，升温至回流搅拌反应12小时，降到室温，过滤，滤饼用二氯甲烷洗，滤液减压浓缩干，用硅胶柱分离纯化，得到黄色固体Int-4，收率75％。
第五步：中间体Int-5的制备
在氮气保护下，20.0mmol的Int-4溶于60mL的甲苯，加入30.0mmol的叔丁醇钠、0.2mmol的Pd2(dba)3和0.04mL的10％三叔丁基磷甲苯溶液，升温至100℃，搅拌反应12小时，降至室温，加入50mL的水，用EA萃取，有机相干燥，过滤，减压浓缩干，用正己烷分散过滤，得到黄色固体Int-5，收率：77％。
第六步：中间体Int-6的制备
在氮气保护下，10.0mmol的中间体Int-5溶于40mL干燥的DMSO中，加入12.0mmol的65％氢化钠固体，搅拌反应30分钟，再加入12.0mmol的2-氯-4,6-二联苯基-1,3,5-三嗪(反应物3)，升温至45℃搅拌反应12小时，降到室温，将反应液倒入150mL的冰水中，过滤，滤饼用水洗、乙醇洗，用硅胶柱分离纯化，得到黄色固体Int-6，收率87％。
第七步：化合物C483的制备
10.0mmol的中间体Int-6溶于60mL的THF和10mL的三乙胺中，加入0.5g的10％钯/碳，通入氢气至0.1MPa，于室温搅拌反应12小时，过滤，滤饼用THF洗，滤液减压浓缩干，用硅胶柱分离纯化，再用甲苯/THF重结晶，得到黄色固体C483，收率100％，MS(MALDI-TOF)：m/z＝738.2665[M+H]+；1HNMR(δ、CDCl3)：8.78(2H,s)；8.69～8.67(1H,d)；8.42～8.38(4H,m)；8.17～8.10(4H,m)；7.96～7.89(3H,m)；7.79～7.70(4H,m)；7.68～7.61(4H,m)；7.58～7.55(1H,m)；7.53～7.46(5H,m)；7.41～7.37(2H,m)；7.32～7.29(1H,m)。
参照上述的合成方法，制备以下表1所示化合物：
表1
实施例2
化合物C523的制备方法，包括如下步骤：
第一步：中间体Int-7的制备
在氮气保护下，20.0mmol的Int-5(反应物1)、22.0mmol的苯硼酸(反应物2)、45.0mmol的无水碳酸钾、0.01mmol的Pd0132和40mL的甲苯、20mL的乙醇以及20mL的水混合，升温至回流搅拌反应12小时，降至室温，加入50mL的水，用EA萃取，有机相干燥，过滤，减压浓缩干，用硅胶柱分离纯化，得到黄色固体Int-7，收率88％。
参照上述类似的合成方法，制备以下化合物：
第二步：化合物C523的制备
在氮气保护下，10.0mmol的中间体Int-7溶于40mL干燥的DMSO中，降温至0℃，分批加入12.0mmol的65％氢化钠固体，搅拌反应30分钟，再加入12.0mmol的2-氯-4-联苯基-6-苯基-1,3,5-三嗪(反应物3)，升至室温搅拌反应12小时，将反应液倒入150mL的冰水中，过滤，滤饼用水洗、乙醇洗，用硅胶柱分离纯化，甲苯/THF重结晶，得到黄色固体C523，收率79％，MS(MALDI-TOF)：m/z＝738.2665[M+H]+；1HNMR(δ、CDCl3)：8.36～8.32(3H,m)；8.17～8.12(3H,m)；8.08～8.05(2H,m)；7.92(1H,s)；7.86～7.84(1H,d)；7.82～7.73(5H,m)；7.70～7.67(3H,m)；7.62～7.56(2H,m)；7.53～7.42(8H,m)；7.39～7.36(2H,m)；7.33～7.29(1H,m)。
参照上述的合成方法，制备以下表2所示化合物：
表2
实施例3
化合物C577的制备方法，以G为O为例，包括以下步骤：
第一步：中间体Int-9的制备
10.0mmol的中间体Int-5(反应物1)溶于40mL的THF和10mL的三乙胺中，加入0.2g的10％钯/碳，通入氢气至0.1MPa，于室温搅拌反应12小时，过滤，滤饼用THF洗，滤液减压浓缩干，用硅胶柱分离纯化，再用甲苯/THF重结晶，得到化合物Int-9，收率100％。
第二步：化合物C577的制备
在氮气保护下，10.0mmol的中间体Int-9溶于50mL干燥的二甲苯中，加入12.0mmol的2-(3-溴苯基)-4-(二苯并[b,d]呋喃-1-基)-6-苯基-1,3,5-三嗪(反应物2)、15.0mmol叔丁醇钠、0.1mmol的Pd2(dba)3和0.2mmol的XPhos，升温至110℃搅拌反应12小时，降到室温，加入50mL水，过滤，滤饼用水洗、乙醇洗，用硅胶柱分离纯化，再用二氯甲烷/THF重结晶，得到黄色固体C577，收率85％，MS(MALDI-TOF)：m/z＝752.2464[M+H]+；1HNMR(δ、CDCl3)：8.78～8.71(3H,m)；8.53～8.51(1H,d)；8.43～8.37(2H,m)；8.28(1H,s)；8.19～8.15(2H,m)；8.01～7.99(1H,d)；7.93～7.85(4H,m)；7.80～7.78(1H,d)；7.72～7.57(7H,m)；7.55～7.48(4H,m)；7.39～7.37(1H,m)；7.34～7.29(1H,m)；7.17～7.14(1H,m)。
参照上述的合成方法，制备以下表3所示化合物：
表3
上述实施例1至实施例3中，*—G—*选自*—O—*、*—S—*或下述结构中的一种：
实施例4
一种OLED元件，如图1所示，本实施例的OLED元件为顶发射光元件，包括基板101、设于基板101上的阳极层102、设于阳极层102上的空穴注入层103、设于空穴注入层103上的空穴传输层104、设于空穴传输层104上的电子阻挡层105、设于电子阻挡层105上的有机发光层106、设于有机发光层106上的电子传输层107、设于电子传输层107上的电子注入层108、设于电子注入层108上的阴极层109以及设于阴极109上的封盖层110，所述的OLED元件的制备方法包括如下步骤：
1)将涂布了ITO导电层的玻璃基片在清洗剂中超声处理30分钟，在去离子水中冲洗，在丙酮/乙醇混合溶剂中超声30分钟，在洁净的环境下烘烤至完全干燥，用紫外光清洗机照射10分钟，并用低能阳离子束轰击表面。
2)把上述处理好的ITO玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述ITO膜上蒸镀金属银作为阳极层，蒸镀膜厚为
继续分别蒸镀化合物HI01和F4TCNQ作为空穴注入层，其中，F4TCNQ为HI01质量的3％，蒸镀膜厚为
3)在上述空穴注入层上继续蒸镀化合物HTM102为空穴传输层，蒸镀膜厚为
4)在上述空穴注入层上继续蒸镀化合物EBL为电子阻挡层，蒸镀膜厚为
5)在电子阻挡层上继续蒸镀本发明的化合物式(I)为主体材料和RD09为掺杂材料，RD09为式(I)质量的3％，作为元件的有机发光层，蒸镀所得有机发光层的膜厚为
6)在有机发光层上继续蒸镀一层LiQ和ET01作为元件的电子传输层，其中，ET01为LiQ质量的50％，蒸镀膜厚为
7)在电子传输层之上继续蒸镀一层LiF为电子注入层，蒸镀膜厚为
8)在电子注入层之上蒸镀金属镁和银作为元件的透明阴极层，镁和银的质量比为1:10，蒸镀膜厚为
9)在透明阴极层之上再蒸镀一层NPD作为元件的CPL层，蒸镀膜厚为
得到本发明提供的OLED元件。
上述实施例4中使用的化合物结构如下：
实施例5
一种有机电致发光元件200，其结构如图2所示，其包含衬底201、阳极202、空穴注入203、空穴传输层204、第一发光层205、电子传输层206、电荷产生层207、空穴注入层208、空穴传输层209、第二发光层210、电子传输层211、电子注入层212以及阴极213。
对比例1
按照与实施例4相同的步骤，将步骤5)中的化合物(式I)替换为HS01，得到对比元件1；
对比例2
按照与实施例4相同的步骤，将步骤5)中的化合物(式I)替换为HS02，得到对比元件2；
对上述过程制备的有机电致发光元件进行如下性能测试：
使用数字源表及亮度计测定实施例4及对比例1、2中制备得到的有机电致发光元件的驱动电压和电流效率以及元件的寿命。具体而言，以每秒0.1V的速率提升电压，测定当有机电致发光元件的亮度达到1000cd/m2时的电压即驱动电压，同时测出此时的电流密度；亮度与电流密度的比值即为电流效率；LT90％寿命测试如下：使用亮度计在1000cd/m2亮度下，保持恒定的电流，测量有机电致发光元件的亮度衰减为900cd/m2的时间，单位为小时。表4中列出的数据是相较于对比元件1的相对数据。
表4
上述表4中，Ph为苯基；PhPh为联苯基；Me为甲基；FR为9,9-芴基。
由表4可知，本发明的化合物制备的元件在相同的亮度下，驱动电压相较HS01低，电流效率提高明显，最高达到对比元件的1.2倍之多，而且元件的LT90％寿命有较大的改善。
对比例1中的化合物HS01与本发明的化合物相比，区别在于苯并咔唑平面共轭能力弱，对空穴和电子的传输不平衡，其接受空穴的能力强于接受电子的能力，这种传输的不平衡影响了激子在发光层中的形成，导致电压高、效率偏低，且寿命下降。而本发明的化合物在苯并咔唑的基础上引入键合的咔唑，提高了母核的共轭能力，所以其在分子成膜及电荷的传输上性能均较优异，元件内电荷的传输更加平衡，元件性能提高。
对比例2中的化合物HS02与本发明的化合物相比，区别在HS02为萘并咔唑，虽然平面共轭能力得到增强，但与本发明的咔唑化合物相比平面共轭能力弱，另一咔唑环的并入形成大共轭稠环结构，所以其在分子成膜及电荷的传输上性能均较优异，元件内电荷的传输更加平衡，在元件性能上，尤其是LT90％寿命均大大高于对比元件，因此本发明的咔唑衍生物是性能优异的有机电致发光材料。
虽然，上文中已经用一般性说明及具体实施方案对本发明作了详尽的描述，但在本发明基础上，可以对之作一些修改或改进，这对本领域技术人员而言是显而易见的。因此，在不偏离本发明精神的基础上所做的这些修改或改进，均属于本发明要求保护的范围。
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。
Claims (10)
1.一种咔唑衍生物，其特征在于，所述咔唑衍生物的结构式如式(I)所示：
其中，
L1选自单键、取代或未取代的C6-C60亚芳基、或者取代或未取代的C2-C60杂亚芳基；
X1、X2、X3各自独立地为N或CR7；
R1、R2、R3、R4、R5、R6、R7相同或不同的选自由氢、氘、氟、羟基、腈基、硝基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C1-C40烷氧基、C2-C40烯基、C1-C40烷硫基、C1-C40烷氧基、C3-C40环烷基、C1-C40烷基亚砜基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫基、取代或未取代的C6-C60芳基亚砜基、取代或未取代的C3-C40甲硅烷基、取代或未取代的硼基、取代或未取代的胺基、取代或未取代的芳基膦基、取代或未取代的氧化膦基、或者取代或未取代的C2-C60杂环芳基组成的群组；
n表示0-5的整数；
Ar1选自由取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、或者取代或未取代的C2-C60杂环芳基组成的群组。
2.根据权利要求1所述的咔唑衍生物，其特征在于，所述X1、X2、X3各自独立地为CR7；
n为0、1或2；
R1、R2、R3、R4、R5、R6、R7各自独立地选自由氢、氘、氟、腈基、苯基、二联苯基、三联苯基、萘基、菲基、三亚苯基、咔唑、二苯并呋喃或二苯并噻吩组成的群组；
Ar1选自如下物质的基团：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、四联苯、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、喹唑啉和苯并噻二唑或者衍生自这些体系的组合的基团。
3.根据权利要求1所述的咔唑衍生物，其特征在于，所述Ar1选自由以下II-1～II-17所示基团组成的群组：
其中，
Z1、Z2各自独立地选自由氢、氘、卤素、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基组成的群组；
x1表示1-4的整数；x2表示1-3的整数；x3表示1或2；x4表示1-6的整数；x5表示1-5的整数；
T1表示O、S、CR’R”或NAr’；
R’、R”各自独立地选自由氢、氘、C1～C40的烷基、C1～C40的杂烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组，R’和R”可任选地接合或稠合形成另外的一个多个取代或未取代的环，在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S；
Ar’选自由C1～C40的烷基、C1～C40的杂烷基、C3～C40的环烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组。
4.根据权利要求1所述的咔唑衍生物，其特征在于，所述L1选自由以下III-1～III-15所示基团组成的群组：
其中，
Z11、Z12各自独立地选自由氢、氘氢、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基组成的群组；
Z13表示取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基中的一种或多种；
y1表示1-4的整数；y2表示1-6的整数；y3表示1-3的整数；y4表示1-5的整数；
T3表示O或S。
5.根据权利要求1～4中任一项所述的咔唑衍生物，其特征在于，所述咔唑衍生物选自如下式C470-C625所示的化合物：
其中，*—G—*选自*—O—*、*—S—*或下述结构中的一种：
6.一种有机电致发光材料，其特征在于，所述有机电致发光材料的原料包括权利要求1～5中任一项所述的咔唑衍生物。
7.权利要求6所述有机电致发光材料在制备有机电致发光元件中的应用。
8.一种有机电致发光元件，其特征在于，所述有机电致发光元件包括：第一电极、第二电极、封盖层和置于所述第一电极、所述第二电极之间的一层以上的有机层；所述有机层或封盖层中的至少一层的材料包括权利要求1～5中任一项所述的咔唑衍生物。
9.根据权利要求8所述的有机电致发光元件，其特征在于，所述有机层包括空穴注入层、空穴传输层、空穴阻挡层、发光层、电子传输层、电子注入层或电子阻挡层。
10.一种消费型产品，其特征在于，所述消费型产品包括权利要求8或9所述的有机电致发光元件。
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| WO2024012469A1 (zh) * | 2022-07-14 | 2024-01-18 | 上海八亿时空先进材料有限公司 | 一种咔唑衍生物及其在有机发光元件中的应用 |
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