CN115028630A - 一种氮杂金刚烷化合物、有机电致发光元件 - Google Patents
一种氮杂金刚烷化合物、有机电致发光元件 Download PDFInfo
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- CN115028630A CN115028630A CN202210684296.8A CN202210684296A CN115028630A CN 115028630 A CN115028630 A CN 115028630A CN 202210684296 A CN202210684296 A CN 202210684296A CN 115028630 A CN115028630 A CN 115028630A
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- Prior art keywords
- substituted
- unsubstituted
- group
- aryl
- alkyl
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- -1 Azaadamantane compound Chemical class 0.000 title claims abstract description 55
- 239000000463 material Substances 0.000 claims abstract description 52
- 239000010410 layer Substances 0.000 claims description 170
- 125000003118 aryl group Chemical group 0.000 claims description 62
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 17
- 229910052805 deuterium Inorganic materials 0.000 claims description 17
- 125000001769 aryl amino group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000005605 benzo group Chemical group 0.000 claims description 11
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 11
- 125000002560 nitrile group Chemical group 0.000 claims description 11
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 10
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 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 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 6
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 6
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 150000004832 aryl thioethers Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 6
- 229950000688 phenothiazine Drugs 0.000 claims description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 6
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 5
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 4
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- MQUPWTBHHPUUMC-UHFFFAOYSA-N isoindole Chemical compound C1=CC=C[C]2C=NC=C21 MQUPWTBHHPUUMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 3
- 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 3
- 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 3
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 claims description 3
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims description 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 claims description 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 3
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 3
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 claims description 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 3
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 3
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 3
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical compound C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 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 3
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 3
- 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 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 3
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 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 3
- 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 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012964 benzotriazole Substances 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
- BKRRPNHAJPONSH-UHFFFAOYSA-N carbazole Chemical compound C1=CC=C2[C]3C=CC=CC3=NC2=C1 BKRRPNHAJPONSH-UHFFFAOYSA-N 0.000 claims description 3
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 3
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005597 hydrazone group Chemical group 0.000 claims description 3
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 3
- 229960005544 indolocarbazole Drugs 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/20—Spiro-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- 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
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- 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
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract
Description
技术领域
本发明涉及有机电致发光材料技术领域,尤其涉及一种氮杂金刚烷化合物及其在有机电致发光元件中的应用。
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。
由此,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。
鉴于此,特提出本发明。
发明内容
本发明的目的在于提供一种氮杂金刚烷化合物,利用该氮杂金刚烷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;本发明的另一目的在于提供该氮杂金刚烷化合物的应用。
具体地,本发明提供以下技术方案:
本发明提供一种氮杂金刚烷化合物,其结构式如式(I)所示:
R1、R2、R3、R4、R5、R6、R7、R8各自独立地选自由氢、氘、卤素、腈基、C1-C40的烷基、C3-C40的环烷基或带有支链的烷基、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、取代或未取代的C2-C60杂环芳基、或者式(II)所示基团组成的群组,任意相邻的两个或多个取代基可任选的接合或稠合形成取代或未取代的环;
Ar1、Ar2各自独立地选自由C1-C40的烷基、C3-C40的环烷基或带有支链的烷基、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,Ar1、Ar2可以任意的接合或稠合形成取代或未取代的环;
m选自0~5的整数;
L1选自单键、取代或未取代的C6-C60的亚芳基、或者取代或未取代的C2-C60亚杂芳基;
*-表示R1、R2、R3、R4、R5、R6、R7或R8与L1的连接键。
进一步地,所述R1、R2、R3、R4、R5、R6、R7、R8各自独立地选自由氢、氘、氟、腈基、甲基、乙基、叔丁基、苯基、联苯基、三联苯基、萘基、菲基、三亚苯基、咔唑基、芴基、二苯并呋喃、二苯并噻吩、取代或未取代的C6-C60芳胺基、取代或未取代的C2-C60杂环芳基、或者式(II)所示基团组成的群组,并且在R1、R2、R3、R4、R5、R6、R7、R8中至少有一者为式(II)所示基团,或者任意相邻的两个或多个取代基可任选的接合或稠合形成取代或未取代的环。
进一步地,所述Ar1、Ar2各自独立地选自由取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基组成的群组。
进一步地,所述m选自0、1或2。
进一步地,所述R1、R2、R3、R4、R5、R6、R7、R8各自独立地选自由氢、氘、氟、腈基、取代或未取代的C6-C60芳基、取代或未取代的C2-C60杂环芳基组成的群组,并且在R1、R2、R3、R4、R5、R6、R7、R8中至少有一者为取代或未取代的C6-C60芳基或取代或未取代的C2-C60杂环芳基,或任意相邻的两个或多个取代基可任选的接合或稠合形成取代或未取代的环。
作为优选,所述芳基、杂环芳基选自由以下基团组成的群组: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。
作为优选,所述L1选自单键或由以下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、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的烷基、C2-C60的烯基、C2-C60的炔基、C1-C60的烷氧基、C3-C60的环烷烃基、C3-C60的环烯烃基、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;
T2选自O、S、CR’R”或NAr’;
R’、R”各自独立地选自由氢、氘、C1-C60的烷基、C1-C60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或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;优选地,R’、R”为甲基、苯基或芴基;
Ar’选自由C1-C60的烷基、C1-C60的杂烷基、C3-C60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;优选地,Ar’为甲基、乙基、苯基或萘基;
作为优选,所述Ar1、Ar2选自由以下所示基团组成的群组:
其中,
每个取代基上的氢原子均可被取代基取代,所述取代基选自由氢氘、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-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60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;
G选自O、S、CR’R”或NAr’;
R’、R”各自独立地选自由氢、氘、C1-C60的烷基、C1-C60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或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;优选地,R’、R”为甲基、苯基或芴基;
Ar’选自由C1-C60的烷基、C1-C60的杂烷基、C3-C60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;优选地,Ar’为甲基、乙基、苯基或萘基;
*-表示Ar1、Ar2与N的连接键。
本发明的芳基、稠环芳基或杂环芳基,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、喹唑啉和苯并噻二唑或者衍生自这些体系的组合的基团。
本发明中,“取代或未取代的”这一用语是指,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的烷基、C2-C60的烯基、C2-C60的炔基、C1-C60的烷氧基、C3-C60的环烷基、C3-C60的环烯基、C6-C60的芳基、C6-C60的芳氧基、C6-C60的芳硫醚基和C2-C60的杂环芳基中的1个以上的取代基取代或未取代,或者被上述示例的取代基中的2个以上的取代基连接而成的取代基取代或未取代。
根据本发明的实施例,所述*-NAr1Ar2选自由下述式B1~B15组成的群组:
其中,*-G-*选自单键、*-O-*、*-S-*或下述结构中的一种:
*-和-*表示与两个苯环的连接键;
所述B1~B15结构中的每个R7各自独立地选自由氢、氘、卤素、腈基、C1-C40的烷基、C3-C40的环烷基或带有支链的烷基、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、取代或未取代的C2-C60杂环芳基组成的群组,此时,当取代基为一种以上时,多个取代基彼此相同或不同。
作为优选,所述氮杂金刚烷化合物选自由以下D253至D525组成的群组:
其中,*-T3-*选自*-O-*、*-S-*或下述结构中的一种:
*-和-*表示连接键。
本发明还提供以上所述的氮杂金刚烷化合物的制备方法,如方案1~方案2所示:
方案1,
方案2,
在方案1、2中,X1、X2、X3为H、Cl、Br、I或OTf;R为H、烷基或芳基;其它所用符号如式(I)中所定义,
合成式(I)所示化合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,得到目标产物。
具体地,式(I)的化合物是由X1取代的联苯经过取代反应、缩合反应、SUZUKI偶联等反应制备化合物式(I)。中间体Ar1Ar2N-(L)mB(OH)2或Ar1Ar2NH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,或使用两种或更多种的混合物。
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,以及其中一种或两种或更多种的混合物。
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,其原料包括以上所述的氮杂金刚烷化合物;包括本发明的氮杂金刚烷化合物的有机电致发光材料具有载流子传输的能力。
作为优选,所述有机电致发光材料为空穴注入层材料、空穴传输层材料、空穴阻挡层材料、发光层材料、电子传输层材料、电子注入层材料、封盖层(简称CPL层)材料或电子阻挡层材料。
本发明同时提供以上所述的氮杂金刚烷化合物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、CPL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、CPL层中的至少一层包括以上所述的氮杂金刚烷化合物。
所述有机电致发光元件包含阴极、阳极、CPL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元件可包含一个发光层,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化合物。
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,即发光层与空穴注入层或阳极直接相邻,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,特别是在空穴传输层中和发光层中以及在CPL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。
一般来说,OLED包含至少一个有机层,其安置在阳极与阴极之间且与阳极和阴极电连接。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、电子传输层107、电子注入层108、阴极109以及封盖层(CPL)110。装置100可通过依序沉积所描述的层来制造。
图2展示含有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、空穴注入层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装置具有一个单色发光层或具有三个三原色的发光层,而装置200具有两个相同光色的发光层。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。
图1和图2中所说明的简单分层结构是作为非限制实例而提供,且应当理解,可结合各种各样的其它结构使用本发明的实施例。所描述的特定材料和结构本质上是示范性的,且可使用其它材料和结构。可基于设计、性能和成本因素,通过以不同方式组合所描述的各个层来实现功能性OLED,或可完全省略若干层。还可包含未具体描述的其它层。可使用不同于具体描述的材料。尽管本文所提供的实例中的许多实例将各种层描述为包括单一材料,但将理解,可使用材料的组合,例如基质与掺杂剂的混合物,或更一般来说,混合物。并且,所述层可具有各种子层。本文中给予各个层的名称不意欲为严格限制性的。举例来说,在装置200中,空穴传输层204传输空穴并将空穴注入到发光层205中,且可被描述为空穴传输层或电子阻挡层。在一个实施例中,可将OLED描述为具有安置在阴极与阳极之间的有机层。此有机层可包括单个层或可进一步包括如例图1和图2所描述的不同有机材料的多个层。
还可使用未具体描述的结构和材料,例如包含聚合物材料的PLED。作为另一实例,可使用具有单个有机层的OLED或多个堆叠。OLED结构可脱离图1和图2中所说明的简单分层结构。举例来说,衬底可包含有角度的反射表面以改进光耦合。
另一方面,关于本发明的有机电致发光元件,除了上述有机物层中的一层以上包含以上所述的茚衍生物之外,可以利用本领域中公知的材料和方法来形成有机物层和电极制造。
此外,可用作根据本发明的有机电致发光元件中所包含的阳极的物质没有特别限定,作为非限制性例子,可以使用钒、铬、铜、锌、金、铝等金属或它们的合金;氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;ZnO:Al或SnO2:Sb等金属与氧化物的组合;聚噻吩、聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDT)、聚吡咯和聚苯胺等导电性高分子;以及炭黑等。
可用作根据本发明的有机电致发光元件中所包含的阴极的物质没有特别限定,作为非限制性例子,可以使用镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡或铅等金属或它们的合金;及LiF/Al或Li2O/Al等多层结构物质等。
可用作根据本发明的有机电致发光元件中所包含的基板的物质没有特别限定,作为非限制性例子,可以使用硅片、石英、玻璃板、金属板或塑料膜和片等。
此外优选如下的有机电致发光元件,可以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,也可以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,包括借助于升华方法来施加至少一个层,和/或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化合物。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,需要处理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、CPL层或电子阻挡层。
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。
本发明还涉及包含至少一种式(I)化合物或上述优选实施方式和至少一种其它化合物的混合物。如果将根据本发明的化合物用作基质材料,则其它化合物可以是荧光或磷光发光体。于是该混合物还可以另外包含其它材料作为附加基质材料。本发明还涉及本发明的化合物在电子元件中的用途。优选地,如上下文提及的,将根据本发明的化合物用于空穴传输层中或用作发光层中的基质材料。根据本发明的化合物和可由此获得的电子元件、特别是有机电致发光元件与现有技术的区别在于以下令人惊讶的优势中的一种或多种:
1.与使用常规化合物获得的电子元件相比,使用本发明的化合物可获得的电子元件表现出非常高的稳定性和非常长的寿命。
2.使用本发明的化合物可获得的电子元件表现出高的效率,特别是高的发光效率和高的外量子效率。
3.本发明的化合物提供低工作电压。
4.可以使用常规方法处理根据本发明的化合物,从而也能够实现成本优势。
5.使用本发明的化合物可获得的薄膜表现出优异的品质,特别是在薄膜的均匀性方面更是如此。
6.可以使用常规方法以非常快速且容易的方式生产本发明的化合物,从而也能够实现成本优势。
上文提及的这些优势并未伴随其它电子性质的削弱。
应该指出,本发明中所述的实施方式的变化落入本发明的范围内。本发明中公开的每个特征除非被明确排除,否则可被具有相同、等效或类似目的的替代特征代替。因此,除非另外说明,否则本发明中公开的每个特征均应被视为类属系列的实例或者等效或类似特征。
本发明的所有特征可以以任何方式彼此组合,除非特定特征和/或步骤是互斥的。这特别适用于本发明的优选特征。同样,非必须组合的特征可以单独(且不组合)使用。此外应该指出,许多特征,特别是本发明的优选实施方式的特征本身是创造性的,并且不应仅视为本发明实施方式的一部分。对于这些特征,除当前要求保护的每个发明以外或作为其替代,可以寻求独立的保护。
对本发明中公开的技术动作的教导可以被提取出并且与其它实施例组合。本发明通过以下实施例更加详细地解释,但不希望由此限制本发明。基于所述描述,本领域技术人员将能够在所公开的整个范围内执行本发明,并且不付出创造性劳动就能够制备本发明的其它化合物并将其用于电子元件中,或使用本发明的方法。
附图说明
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、电子传输层107、电子注入层108、阴极109以及封盖层(CPL)110。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D275的制备方法,包括如下步骤:
第一步:中间体Int-1的制备
在氮气保护下,20.0mmol的2-溴-4′-氯-1,1′-联苯解于50mL干燥的THF中,液氮降温至-78℃,滴加入22.0mmol的2.5M正丁基锂正己烷溶液,搅拌反应30分钟,再滴加入24.0mmol的5-氮杂金刚烷-2-酮,升至室温搅拌反应1小时,加入20mL的饱和氯化铵水溶液,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,加入50mL的二氯甲烷溶解,再加入60.0mmol的三氟乙酸,搅拌反应12小时,用10%的氢氧化钠水溶液洗至碱性,收集有机相,干燥,过滤,滤液减压浓缩干,过硅胶短柱,正己烷洗脱,减压浓缩干,得到Int-1,白色固体,收率65%。
第二步:化合物D275的制备
12.0mmol的Int-1溶解于60mL的二甲苯中,在氮气保护下,加入10.0mmol的N-联苯基-4′-(9-咔唑基)-联苯-4-胺、15.0mmol的叔丁醇钠、0.1mmol的碘化亚铜、0.1mmol的Pd2(dba)3催化剂,再加入0.2mmol的Xantphos,升温至110℃搅拌反应16小时,降到室温,加入20mL的水稀释,用甲苯萃取,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D275,收率85%,MS(MALDI-TOF):m/z=772.3705[M+H]+;1HNMR(δ、CDCl3):8.18(2H,s);8.12(1H,s);7.94~7.85(6H,m);7.72~7.69(2H,m);7.57~7.52(6H,m);7.50~7.45(3H,m);7.41~7.32(7H,m);7.29~7.25(2H,m);7.21~7.14(3H,m);3.11~3.04(2H,m);2.72~2.55(3H,m);2.24~2.15(3H,m);1.86~1.79(1H,m);1.77~1.68(2H,m);1.65~1.56(2H,m)。
参照上述实施例1类似的合成方法,制备如表1所示产物。
表1反应物与合成产物及收率对应表
其中,*-T3-*选自*-O-*、*-S-*或下述结构中的一种:
*-和-*表示连接键。
实施例2
化合物D413的制备,以T3为C(CH3)2为例:
在氮气保护下,35.0mmol的(4-([1,1′-联苯]-2-基(9,9-二甲基-9H-芴-2-基)胺)苯基)硼酸频哪醇酯混于80mL的甲苯中,加入25.0mmol的Int-1、75.0mmol的无水碳酸钾、0.01mmol的Pd0132催化剂,再加入40mL的乙醇和40mL的水,升温至回流搅拌反应12小时,降到室温,加入50mL的水稀释,用甲苯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,过硅胶短柱,甲苯洗脱,减压浓缩干,再用甲苯-THF重结晶,得到化合物D413,白色固体,收率78%,MS(MALDI-TOF):m/z=723.3747[M+H]+;1HNMR(δ、CDCl3):8.27~8.25(1H,m);8.08~8.06(1H,m);7.90~7.84(4H,m);7.78~7.76(1H,d);7.53~7.48(4H,m);7.45~7.34(9H,m);7.32~7.27(3H,m);7.16~7.12(2H,m);7.09~7.05(2H,m);3.08~3.02(2H,m);2.69~2.55(3H,m);2.24~2.16(3H,m);1.85~1.79(1H,m);1.74~1.65(8H,m);1.62~1.54(2H,m)。
参照上述实施例2类似的合成方法,制备如表2所示产物。
表2反应物与合成产物及收率对应表
其中,*-T3-*选自*-O-*、*-S-*或下述结构中的一种:
*-和-*表示连接键。
实施例3
化合物D457的制备方法,以T3=O为例,包括以下步骤:
第一步:化合物Int-2的制备
在氮气保护下,20.0mmol的Int-1溶解于40mL的DMF中,加入24.0mmol的联硼酸频哪醇酯、2.0mmol的碘化亚铜、30.0mmol的无不醋酸钾和0.2mmol的PdCl2(dppf)催化剂,升温至110℃,搅拌反应12小时,降至室温,将反应液倒入100mL的水中,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Int-2,收率81%。
第二步:化合物D457的制备
在氮气保护下,12.0mmol的Int-2溶解于50mL的甲苯中,加入10.0mmol的2-氯-4-(二苯并[b,d]呋喃-1-基)-6-苯基-1,3,5-三嗪、24.0mmol的六水合磷酸钾、0.01mmol的Pd0132,再加入30mL的乙醇和20mL的水,升温回流搅拌反应15小时,降至室温,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D457,白色固体,收率83%,MS(MALDI-TOF):m/z=609.2672[M+H]+;1HNMR(δ、CDCl3):8.35~8.32(3H,m);8.08~8.06(1H,d);8.01~7.99(1H,m);7.90~7.82(4H,m);7.66~7.63(1H,m);7.55~7.48(5H,m);7.39~7.35(2H,m);7.33~7.27(2H,m);3.08~3.02(2H,m);2.69~2.55(3H,m);2.33~2.16(3H,m);1.86~1.79(1H,m);1.74~1.65(2H,m);1.62~1.53(2H,m)。
参照上述实施例3类似的合成方法,制备如表3所示产物。
表3反应物与合成产物及收率对应表
其中,*-T3-*选自*-O-*、*-S-*或下述结构中的一种:
*-和-*表示连接键。
实施例4
化合物D483的制备方法,包括以下步骤:
第一步:化合物Int-3的制备
在氮气保护下,22.0mmol的Int-2’溶解于60mL的甲苯中,加入20.0mmol的邻溴硝基苯、66.0mmol的无不碳酸钠和0.1mmol的Pd(PPh3)4催化剂,再加入30mL的乙醇和30mL的水,升温至回流搅拌反应12小时,降至室温,加入50mL的水稀释,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Int-3,黄色固体,收率87%。
第二步:化合物Int-4的制备
在氮气保护下,20.0mmol的Int-3溶解于20mL的邻二氯苯中,加入60.0mmol的三苯基磷,升温至回流搅拌反应12小时,降至室温,加入50mL的二氯甲烷溶解,冲短硅胶柱,用二氯甲烷洗脱,减压浓缩干,用二氯甲烷-乙醇重结晶,得到化合物Int-4,白色固体,收率64%。
第三步:化合物D483的制备
在氮气保护下,20.0mmol的Int-4溶解于60mL的二甲苯中,加入24.0mmol的2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪、2.0mmol的碘化亚铜、30.0mmol的叔丁醇钠和0.2mmol的Pd2(dba)3催化剂以及0.2mL的10%三叔丁基磷甲苯溶液,升温至110℃,搅拌反应12小时,降至室温,加入50mL的水,用二氯甲烷萃取,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D483,收率86%,MS(MALDI-TOF):m/z=684.3135[M+H]+;1HNMR(δ、CDCl3):8.35~8.32(4H,m);8.28(1H,s);8.21~8.15(4H,m);7.86(1H,s);7.74~7.68(2H,m);7.63~7.54(3H,m);7.52~7.40(7H,m);7.37~7.34(1H,m);7.19~7.16(1H,m);3.13~3.07(2H,m);2.74~2.55(3H,m);2.24~2.13(3H,m);1.86~1.70(3H,m);1.67~1.58(2H,m)。
实施例5
化合物D488的制备:
在氮气保护下,20.0mmol的Int-4’溶解于60mL的DMSO中,降温至-10℃,分批加入22.0mmol的65%氢化钠固体,搅拌反应1小时,再加入22.0mmol的2-联苯基-4-氯-6-苯基-1,3,5-三嗪,升至室温拌反应12小时,加入150mL的冰水,用乙酸乙酯萃取,收集有机相,用饱和盐水洗,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D488,黄色固体,收率83%,MS(MALDI-TOF):m/z=684.3143[M+H]+;1HNMR(δ、CDCl3):8.54(1H,s);8.35~8.30(2H,m);8.23~8.21(1H,m);7.98~7.92(4H,m);7.82~7.77(3H,m);7.65~7.63(1H,d);7.57~7.54(1H,m);7.52~7.44(5H,m);7.42~7.33(3H,m);7.25~7.21(2H,m);7.18~7.15(1H,m);3.18~3.12(2H,m);2.81~2.74(2H,m);2.63~2.55(1H,m);2.44~2.37(2H,m);2.24~2.16(1H,m);1.86~1.64(5H,m)。
参照上述实施例4和实施例5类似的合成方法,制备如表4所示产物。
表4反应物与合成产物及收率对应表
其中,*-T3-*选自*-O-*、*-S-*或下述结构中的一种:
*-和-*表示连接键。
实施例6
一种有机电致发光元件100,其结构如图1所示,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上的发光层106、设于发光层106上的电子传输层107、电子注入层108、阴极层109,以及设于阴极层109之上的CPL层110,其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,蒸镀膜厚为蒸镀化合物HI01和F4TCNQ作为空穴注入层,F4TCNQ为HI01质量的3%,蒸镀膜厚为
实施例6中使用的化合物HI01、HT08、HT10、RH12、RD016、ET14和F4TCNQ的结构如下:
实施例7
按照与实施例6相同的步骤,将步骤3)中的HT08替换为本发明的式(I)所示化合物,得到本发明的OLED元件,元件的性能测试比对结果见表6。
实施例8
按照与实施例6相同的步骤,将步骤4)中的HT10替换为本发明的式(I)所示化合物,得到本发明的OLED元件,元件的性能测试比对结果见表7。
实施例9
按照与实施例6相同的步骤,将步骤5)中的RH12替换为本发明的式(I)所示化合物,得到本发明的OLED元件,元件的性能测试比对结果见表8。
实施例10
按照与实施例6相同的步骤,将步骤6)中的ET14替换为本发明的式(I)所示化合物,得到本发明的OLED元件,元件的性能测试比对结果见表8。
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6~实施例10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电流密度达到10mA/cm2时的电压即驱动电压,同时测出此时的亮度;亮度与电流密度的比值即为电流效率;LT95%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950cd/m2的时间,单位为小时,所有数据均为对比元件的归一化结果。
表5各元件性能检测结果
由表5可知,本发明的氮杂金刚烷化合物作为空穴传输层材料制备成的发光元件同样在电流密度为10mA/cm2条件下,驱动电压降低,发光效率有提高显著,而且LT95%寿命有明显优势,是性能良好的空穴传输层材料。
实施例6的化合物HT08与本发明的化合物相比,区别在于氮杂金刚烷含有孤电子对的氮原子,对分子成膜的影响较小,与金刚烷相比空穴迁移率提高,所以其在分子成膜及载流子的传输性能上均较对比的化合物HT08优异,在元件性能和寿命上表现更有优势。
表6各元件性能检测结果
由表6可知,本发明的氮杂金刚烷化合物作为电子阻挡层材料制备成的发光元件同样在电流密度为10mA/cm2条件下,驱动电压降低,发光效率提高明显,而且LT95%寿命有大幅度提升,是性能优异的电子材料。
实施例6中的化合物HT10与本发明的化合物相比,区别在于氮杂金刚烷含有孤电子对的氮原子,更有利于输送空穴而阻挡电子,降低激子在非发光层形成的概率,所以其在发光元件的表现上更加优异。
表7各元件性能检测结果
由表7可知,本发明的氮杂金刚烷化合物作为发光层的主体材料制备成的发光元件同样在电流密度为10mA/cm2条件下,驱动电压降低,发光效率提高明显,而且LT95%寿命有大幅度提升,是性能优异的发光层材料。
实施例6中的化合物RH12与本发明的化合物相比,区别在于二甲基芴的位阻小,将二甲基替换为氮杂金刚烷后不仅位增大,而且利于阻挡空穴的输送,因此分子构成D-A双极性,发光层内的载流子传输更加平衡,更有利于激子在发光层内形成,所以其在发光元件的表现上更加优异。
表8各元件性能检测结果
测试材料 | 驱动电压(V) | 效率(cd/A) | 寿命(h) |
ET14(对比) | 1.00 | 1.00 | 1.0 |
D451 | 92.8% | 103.8% | 2.6 |
D452 | 89.8% | 114.7% | 2.2 |
D453 | 92.1% | 110.5% | 3.5 |
D454 | 90.6% | 100.7% | 3.0 |
D455 | 89.3% | 109.7% | 3.8 |
D456(T<sub>3</sub>:O) | 92.7% | 101.9% | 2.4 |
D457(T<sub>3</sub>:O) | 90.4% | 112.3% | 1.9 |
D458(T<sub>3</sub>:NPh) | 99.2% | 109.0% | 1.2 |
D459(T<sub>3</sub>:FR) | 99.8% | 106.6% | 1.6 |
D460 | 98.9% | 114.4% | 1.5 |
D461 | 92.4% | 110.2% | 1.3 |
D462 | 90.5% | 100.9% | 2.8 |
D463(T<sub>3</sub>:O) | 92.4% | 113.8% | 2.7 |
D464(T<sub>3</sub>:O) | 91.8% | 112.9% | 3.1 |
D465(T<sub>3</sub>:S) | 91.2% | 109.5% | 2.5 |
D466(T<sub>3</sub>:NPh) | 93.8% | 105.7% | 1.8 |
D467 | 89.6% | 115.6% | 1.4 |
D468 | 95.7% | 110.9% | 1.7 |
D469 | 88.7% | 113.8% | 3.3 |
D470 | 87.8% | 110.2% | 3.5 |
D471 | 90.3% | 104.0% | 3.6 |
D472(T<sub>3</sub>:O) | 91.2% | 106.7% | 2.2 |
D473(T<sub>3</sub>:O) | 92.4% | 103.8% | 2.7 |
D474(T<sub>3</sub>:O) | 87.6% | 112.5% | 2.4 |
D475 | 97.7% | 109.5% | 1.5 |
D476 | 98.6% | 108.2% | 1.7 |
D477 | 98.9% | 108.9% | 2.9 |
D478 | 95.4% | 110.6% | 2.7 |
上述表5至表8中,Me为甲基;Ph为苯基;PhPh为联苯基;Nap为萘基;FR为芴基。
由表8可知,本发明的氮杂金刚烷化合物作为电子传输层材料制备成的发光元件同样在电流密度为10mA/cm2条件下,驱动电压降低,发光效率提高明显,而且LT95%寿命有大幅度提升,是性能优异的电子材料。
实施例6中的化合物ET14与本发明的化合物相比,区别在于氮杂金刚烷含有孤电子对的氮原子,氮原子的引入使金刚烷的立体刚性增强,更利于电子的传输和激子的形成,所以其在发光元件的表现上更加优异。
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。
Claims (10)
1.一种氮杂金刚烷化合物,其特征在于,其结构式如式(I)所示:
R1、R2、R3、R4、R5、R6、R7、R8各自独立地选自由氢、氘、卤素、腈基、C1-C40的烷基、C3-C40的环烷基或带有支链的烷基、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、取代或未取代的C2-C60杂环芳基、或者式(II)所示基团组成的群组,任意相邻的两个或多个取代基可任选的接合或稠合形成取代或未取代的环;
Ar1、Ar2各自独立地选自由C1-C40的烷基、C3-C40的环烷基或带有支链的烷基、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,Ar1、Ar2可以任意的接合或稠合形成取代或未取代的环;
m选自0~5的整数;
L1选自单键、取代或未取代的C6-C60的亚芳基、或者取代或未取代的C2-C60亚杂芳基;
*-表示R1、R2、R3、R4、R5、R6、R7或R8与L1的连接键。
2.根据权利要求1所述的氮杂金刚烷化合物,其特征在于,所述R1、R2、R3、R4、R5、R6、R7、R8各自独立地选自由氢、氘、氟、腈基、甲基、乙基、叔丁基、苯基、联苯基、三联苯基、萘基、菲基、三亚苯基、咔唑基、芴基、二苯并呋喃、二苯并噻吩、取代或未取代的C6-C60芳胺基、取代或未取代的C2-C60杂环芳基、或者式(II)所示基团组成的群组,并且在R1、R2、R3、R4、R5、R6、R7、R8中至少有一者为式(II)所示基团,或者任意相邻的两个或多个取代基可任选的接合或稠合形成取代或未取代的环;
Ar1、Ar2各自独立地选自由取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基组成的群组;
m选自0、1或2。
3.根据权利要求1或2任一项所述的氮杂金刚烷化合物,其特征在于,所述L1选自单键或由以下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、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的烷基、C2-C60的烯基、C2-C60的炔基、C1-C60的烷氧基、C3-C60的环烷烃基、C3-C60的环烯烃基、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;
T2选自O、S、CR’R”或NAr’;
R’、R”各自独立地选自由氢、氘、C1-C60的烷基、C1-C60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或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;优选地,R’、R”为甲基、苯基或芴基;
Ar’选自由C1-C60的烷基、C1-C60的杂烷基、C3-C60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;优选地,Ar’为甲基、乙基、苯基或萘基;
4.根据权利要求1~3任一项所述的氮杂金刚烷化合物,其特征在于,所述Ar1、Ar2选自由以下所示基团组成的群组:
其中,
每个取代基上的氢原子均可被取代基取代,所述取代基选自由氢氘、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-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60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;
G选自O、S、CR’R”或NAr’;
R’、R”各自独立地选自由氢、氘、C1-C60的烷基、C1-C60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或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;优选地,R’、R”为甲基、苯基或芴基;
Ar’选自由C1-C60的烷基、C1-C60的杂烷基、C3-C60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;优选地,Ar’为甲基、乙基、苯基或萘基;
*-表示Ar1、Ar2与N的连接键。
6.根据权利要求1所述的氮杂金刚烷化合物,其特征在于,所述R1、R2、R3、R4、R5、R6、R7、R8各自独立地选自由氢、氘、氟、腈基、取代或未取代的C6-C60芳基、取代或未取代的C2-C60杂环芳基组成的群组,并且在R1、R2、R3、R4、R5、R6、R7、R8中至少有一者为取代或未取代的C6-C60芳基或取代或未取代的C2-C60杂环芳基,或任意相邻的两个或多个取代基可任选的接合或稠合形成取代或未取代的环;
所述芳基、杂环芳基选自由以下基团组成的群组: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。
8.一种有机电致发光材料,其特征在于,其原料包括权利要求1-7任一项所述的氮杂金刚烷化合物。
9.权利要求1-7任一项所述的氮杂金刚烷化合物在制备有机电致发光元件中的应用。
10.一种有机电致发光元件,其特征在于,其包括:第一电极、第二电极、CPL层和置于所述第一电极、第二电极之间的至少一个有机层;所述有机层、CPL层中的至少一层包括权利要求1-7任一项所述的氮杂金刚烷化合物。
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