CN112010759A - 一种化合物及其应用、包含其的有机电致发光器件 - Google Patents
一种化合物及其应用、包含其的有机电致发光器件 Download PDFInfo
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- CN112010759A CN112010759A CN201910467330.4A CN201910467330A CN112010759A CN 112010759 A CN112010759 A CN 112010759A CN 201910467330 A CN201910467330 A CN 201910467330A CN 112010759 A CN112010759 A CN 112010759A
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- Prior art keywords
- substituted
- unsubstituted
- compound
- formula
- oxadiazole
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 71
- 239000000463 material Substances 0.000 claims abstract description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims abstract description 3
- -1 C2-C20 alkynyl Chemical group 0.000 claims description 32
- 230000005525 hole transport Effects 0.000 claims description 25
- 238000002347 injection Methods 0.000 claims description 16
- 239000007924 injection Substances 0.000 claims description 16
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 12
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 9
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 8
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-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
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 8
- 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 8
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims description 6
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 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 4
- 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 4
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 claims description 4
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 claims description 4
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 claims description 4
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 4
- 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
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 4
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 4
- WYSBZCPNRXECEW-UHFFFAOYSA-N 1-diazo-2H-anthracene Chemical compound C1=CC=C2C=C3C(=[N+]=[N-])CC=CC3=CC2=C1 WYSBZCPNRXECEW-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
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 4
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 4
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 4
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 claims description 4
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical compound C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 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 4
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 4
- 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 4
- 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 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 4
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012964 benzotriazole Substances 0.000 claims description 4
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 4
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 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
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 4
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 4
- 229950000688 phenothiazine Drugs 0.000 claims description 4
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 claims description 4
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 4
- 150000003536 tetrazoles Chemical class 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
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- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims 2
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- 239000010410 layer Substances 0.000 description 80
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/60—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton containing a ring other than a six-membered aromatic ring forming part of at least one of the condensed ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及一种新型有机化合物,具有如下式(1)的结构:
Description
技术领域
本发明涉及一种有机化合物,其可用于电子器件中的电荷传输材料,特别是空穴类电荷传输材料,尤其是在有机电致发光器件中,作为空穴注入,空穴传输的材料使用。本发明还涉及该化合物在有机电致发光器件中的应用。
背景技术
OLED(Organic light-Emitting diode)显示技术具有自发光,对比度高,响应速度快,色彩饱和度高的优点,特别是其不含背光源,器件结构简单,工作温度范围广,通过挠曲基板可实现柔性显示的特点,使得其成为继LCD后的下一代的显示技术,已经逐渐展现出其广阔的商业应用的前景。
一般的最简单的OLED器件结构是在两个电极间蒸镀几十到几百纳米厚的有机发光材料,通过在两个电极上施加一定的电压来使材料发光。为了实现更高的发光效率和寿命,还需要引入各种辅助层来平衡载流子的传输,通常包括空穴注入层,空穴传输层,电子阻挡层,空穴阻挡层,电子传输层,电子注入层。一个效率好寿命长的有机电致发光器件通常是器件结构以及各种有机材料的优化搭配的结果,为了实现器件以更低的工作电压来实现更高的发光效率和更长的工作寿命,研究者们一直致力于研究和开发新的有机电致发光材料,以期获取更高性能的材料,使OLED发光器件达到更好的工作状态。
在OLED器件中,空穴传输材料可以提高空穴在器件中的传输效率,对器件的性能有着重要的影响。对空穴材料的基本要求包括有(1)具有较高的空穴迁移率;(2)其最高分子占据轨道能级(HOMO)要匹配与其接触的功能层,从而能够实现空穴的有效注入和传输;(3)适宜的热稳定性,要求空穴材料能够蒸镀形成致密均一的薄膜,防止针孔出现,避免缺陷造成对效率及寿命的影响。所以需要空穴材料要有较高的玻璃化转变温度(Tg),有利于形成稳定的非结晶形态。
芴类衍生物有着的特殊的刚性平面结构,化学稳定性高,具有较好的空穴传输性能。专利US2008000736开发一种芴的2,7双三芳胺结构的材料以达到提升效率的目的;CN107641116A中,开发了在芴的2,3位双取代三芳胺材料,提升了器件性能。但在实际的应用中,仍需要不断的提高和平衡器件的空穴迁移率,来满足低驱动电压、高电流效率、较长的使用寿命,所以开发新型的空穴传输材料仍是目前紧迫任务之一。
发明内容
本发明的目的是设计一种芴类的衍生物,通过对取代基以及取代位置的选择,确保该类化合物具有较大的共轭平面和强的分子内电子转移,从而获得较高的热稳定性和光学稳定性,特别是具有优良的空穴传输性能、高载流子的迁移率。
本发明提供了一种由如下通式(1)表示的化合物,
其中,
R和R’相同或不同,分别独立地选自取代或者未取代的下述取代基团中的一种:C1~C20的烷基、C2~C20烯基、C2~C20炔基、C1~C20的烷氧基、C6~C18的芳基、C6~C18的芳氧基或C4~C18的杂芳基,R与R’可以连接成环;
R1和R2分别独立地表示单取代到最大允许个数的取代基,R1和R2各自独立地选自氢、卤素、氰基、硝基、羟基或者选自取代或者未取代的下述取代基团中的一种:C1~C12的烷基、C1~C12硫代烷基、C2~C20烯基、C2~C20炔基、C1~C12的烷氧基、硅烷基中的一种;
A、B和C分别独立地选自取代或未取代的C6~C30的芳基氨基、取代或未取代的C3~C30的杂芳基氨基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种,且A、B中至少一个为下式(2)表示的基团:
式(2)中,Ar1和Ar2分别独立的选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;
L1和L2分别独立选自单键、取代或未取代的C6-C30的亚芳基、取代或未取代的C3~C30的亚杂芳基中的一种;
当上述基团存在取代基时,所述取代基选自卤素、C1-C10的烷基或环烷基、C2-C10烯基、C1-C6的烷氧基或硫代烷氧基基团、C6-C30的单环芳烃或稠环芳烃基团、C3-C30的单环杂芳烃或稠环杂芳烃基团中的一种。
进一步的,本发明上述的式(1)优选如下式(3-1)或(3-2)所示:
式(3-1)和(3-2)中,A、B和C分别独立选自取代或未取代的C6~C30芳基、取代或未取代的C3~C30杂芳基中的一种;
R和R’、R1和R2、L1和L2、Ar1和Ar2的定义均与在式(1)和式(2)中的定义相同。
进一步的,式(3-1)和(3-2)中,L1和L2分别独立优选为单键,或优选为取代或未取代的下述基团:亚苯基、亚联苯基、亚萘基、亚菲基中的一种;Ar1和Ar2分别独立选自取代或者未取代的下述基团:苯基、联苯基、萘基、菲基、芴、二苯并呋喃、二苯并噻吩中的一种。
更进一步的,式(3-1)中,B、C分别独立优选为取代或者未取代的下述基团:苯、萘、蒽、苯并蒽、菲、苯并菲、芘、窟、茈、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、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、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、吩恶嗪、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、嗯唑、苯并嗯唑、萘并嗯唑、蒽并嗯唑、菲并嗯唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、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、4,5,9,10-四氮杂茈、吡嗪、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-恶二唑、1,2,4-嗯二唑、1,2,5_嗯二唑、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、吲嗪和苯并噻二唑中的一种;最优的选择为苯基或萘基。
更进一步的,式(3-2)中,A、C分别独立优选为取代或者未取代的下述基团:苯、萘、蒽、苯并蒽、菲、苯并菲、芘、窟、茈、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、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、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、吩恶嗪、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、嗯唑、苯并嗯唑、萘并嗯唑、蒽并嗯唑、菲并嗯唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、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、4,5,9,10-四氮杂茈、吡嗪、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-恶二唑、1,2,4-嗯二唑、1,2,5_嗯二唑、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、吲嗪和苯并噻二唑中的一种;最优的选择为苯基或萘基。
更进一步的,式(3-1)和(3-2)中,R1和R2分别独立优选为氢,或者优选为如下的基团中的一种或两种及两种以上的组合: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、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、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、辛炔基、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、2,2,2-三氟乙氧基、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、正戊硫基、仲戊硫基、正己硫基、环己硫基、正庚硫基、环庚硫基、正辛硫基、环辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙條硫基、丙條硫基、丁條硫基、戊條硫基、环戊條硫基、己條硫基、环己條硫基、庚條硫基、环庚烯硫基、辛烯硫基、环辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚块硫基或辛块硫基;最优的选择为苯基或萘基。
作为本发明涉及的化合物的优选结构,可以举出以下所示结构的化合物,但不限于这些化合物:
作为本发明的另一方面,本发明上述通式化合物在有机电致发光器件中作为空穴传输材料、空穴注入材料或电子阻挡材料。
作为本发明的又一个方面,本发明还提供了一种有机电致发光器件,包括第一电极、第二电极和插入在所述第一电极和第二电极之间的至少包含一层发光层的有机层,其特征在于,所述有机层中含有如上所述通式(1)或式(3-1)或式(3-2)表示的化合物。优选的,在有机层中包含的空穴传输层中、空穴注入层中或电子阻挡层中含有如上所述通式(1-1)或式(3-1)或式(3-2)表示的化合物。
上述本发明化合物用作有机电致发光器件中的空穴传输材料、空穴注入材料或电子阻挡材料的原理尚不明确,据推测可能是以下原因:
本发明的通式化合物在芴衍生物母核的2位或3位引入特定的取代基团,使得分子的的空构型由于受到特定取代基团的影响而发生一定的扭曲,取代基的空间位阻作用,使分子的空间构型相对稳定,从而增强了分子稳定性。7位是芴的反应活性位,在特殊环境下易引发分子的反应,通过引入取代基,可进一步增加芴环的稳定性,同时也有利于提高分子的电荷迁移率,从而可以满足制备应用到有机电致发光器件中不同的使用要求,能够有效实现降低器件驱动电压、延长器件的寿命等有益效果。
采用本发明经过结构修饰优化而得到的这类新型化合物,制备应用到有机电致发光器件中时,可以实现降低器件的驱动电压、增加器件的寿命等目的,从而获得更好的器件性能。
具体实施方式
为了使本领域技术人员更好地理解本发明,下面结合具体实施方式对本发明作进一步详细说明。
实施例中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。实施例中所用的各种化学药品如石油醚、乙酸乙酯、甲苯、四氢呋喃、N,N-二甲基甲酰胺、二氯甲烷、碳酸铯、碳酸钾、醋酸钯、2-二环己基磷-2,4,6-三异丙基联苯(XPhos)、2-双环己基膦-2',6'-二甲氧基联苯(SPhos)、四(三苯基膦)钯、叔丁醇钠等基础化工原料均可在国内化工产品市场买到。
参照下面的实施例来更具体地描述本发明,但是本发明并不局限于这些实施例。本发明通式(1)表示的化合物,可通过下面所示的合成路线得到所需的化合物。
本发明中所述化合物(449~896)的通用合成路线:
本发明所述化合物(1-448)的可参考的合成路线
具体实施例
中间体M1的合成:
化合物M1-1的合成
取2-溴-7-羟基-9,9-二甲基芴(18g,62.3mmol)溶于乙酸(400mL),加入硝酸(5.89g,93.5mmol),加热到60℃,然后将浓硫酸(6.72g,68.6mmol)通过恒压滴液漏斗缓慢的滴加上述溶液中,逐渐有固体析出,滴完后,继续搅拌2h,降温。将反应液倒入1L的冰水中,充分搅拌,过滤收集固体,固体用水冲洗,干燥得19g,直接用于下一步。
化合物M1-2的合成
将化合物M1-1(19g,62.0mmol)溶于二氯甲烷(250mL)中,加入三乙胺(7.5g,80.6mmol),冷却到0℃,滴加三氟甲磺酰氯(13.5g,80.0mmol),滴完后,自然升温到室温,搅拌5小时。将反应液倒入到500mL的饱和氯化铵水溶液中,用二氯甲烷萃取(200mL*3),合并有机相,再有饱和食盐水洗涤一次,无水硫酸钠干燥。浓缩得油状物,硅胶柱纯化(PE/EA,10/1)得黄色固体23g。
化合物M1-3的合成
取化合物M1-2(9.2g,19.7mmol)、苯硼酸(5.8g,47.28mmol)和碳酸钾(8.2g,59.2mmol)加入装有甲苯(150mL)、乙醇(70mL)和水(70mL)的三口瓶中,充分搅拌溶解。然后在氮气保护下,加入四(三苯基膦)钯(228mg,0.197mmol),反应体系升温到90℃反应20h,冷却后将反应液倒入300mL的饱和氯化铵水溶液中萃取,水相用甲苯(100mL)萃取两次,合并有机相,无水硫酸钠干燥,浓缩,粗品用硅胶柱提纯(石油醚/二氯甲烷=8/1)得黄色固体。此固体用甲苯和甲醇重结晶,得浅黄色固体8g。
化合物M1的合成
将上述化合物M1-3(8g)装入盛有甲醇(200mL)和THF(200mL)的单口瓶中,放入Pd/C水合物(0.5g),然后用氢气袋充分置换瓶中的空气,并保持氢气压力下,充分搅拌24h。待反应完合后,过滤除去其中的钯炭,滤液浓缩得浅黄色固体,固体用硅胶柱提纯得类白色固体(7g)。
中间体M2的合成:
化合物M2-1的合成
在装配有冷凝管的四口瓶中,加入原料化合物2-溴-7-氨基-9,9-二甲基芴(28.7g,0.1mol)溶于二氯甲烷(500mL)中在冰水浴下,使反应体系降温到0℃,然后将NBS(5.6g,0.1mmol)缓慢地分批次加入上述溶液中,控制反应温度,当NBS完全加入体系后,继续搅拌1h,TLC监测直到原料消失。然后将反应溶液倒入500mL的氯化铵水溶液中萃取分液,水相用200mL二氯甲烷萃取,合并有机相,无水硫酸钠干燥,浓缩得黄色固体。粗品用硅胶层析柱进一步提纯,得浅黄色固体25g。
化合物M2的合成
取化合物M2-1(20.0g,54.8mmol)、苯硼酸(14.7g,120.6mmol)和碳酸钾(18.9g,137.0mmol)加入装有甲苯(300mL)、乙醇(150mL)和水(1500mL)的三口瓶中,充分搅拌溶解。然后在氮气保护下,加入四(三苯基膦)钯(630mg,0.548mmol),反应体系升温到90℃反应20h,冷却后将反应液倒入300mL的饱和氯化铵水溶液中萃取,水相用甲苯(100mL)萃取两次,合并有机相,无水硫酸钠干燥,浓缩,粗品用硅胶柱提纯(石油醚/二氯甲烷=8/1)得淡黄色固体15g。
中间体M3的合成:
中间体M3的合成可参考M1的合成方法,将苯硼酸换成1-萘硼酸。
中间体M4的合成;
中间体M4的合成,参考M1的合成,将苯硼酸换成2-萘硼酸。
中间体M5的合成:
中间体M5的合成参考M2的合成,将苯硼酸换成1-萘硼酸。
中间体M6的合成:
中间体M6的合成参考M2的合成,将苯硼酸换成2-萘硼酸。
合成实施例1:
化合物C6的合成:
化合物C6-1的合成:
将中间体M1(10g,27.7mmol)、4-溴联苯(7.1g,30.5mmol)和叔丁醇钠(3.5g,36.0mmol)加入到150mL的甲苯中,搅拌溶解,用氮气充分置换,然后加入Pd2(dba)3(254mg,0.277mmol),SPhos(227mg,0.554mmol)。在氮气的保护下,升温至回流反应20h,TLC监测至原料完全反应。然后降温到室温,用饱和的氯化铵溶液萃取,水相用甲苯萃取(150mL*2),合并有机相,用饱和食盐水再洗涤一次,无水硫酸钠干燥,过滤,浓缩得粗品。继续用硅胶柱纯化得黄色固体12g。
化合物C6的合成:
将中间体C6-1(10g,19.5mmol)、3-溴联苯(5.4g,23.4mmol)和叔丁醇钠(2.4g,25.4mmol)加入到150mL的甲苯中,搅拌溶解,用氮气充分置换,然后加入Pd2(dba)3(254mg,0.277mmol),SPhos(227mg,0.554mmol)。在氮气的保护下,升温至回流反应20h,TLC监测至原料完全反应。然后降温到室温,用饱和的氯化铵溶液萃取,水相用甲苯萃取(150mL*2),合并有机相,用饱和食盐水再洗涤一次,无水硫酸钠干燥,过滤,浓缩得粗品。继续用硅胶柱纯化得黄色固体10.3g,产品用甲苯和甲醇重结晶两次,得淡黄色固体6.2g。
合成实施例2:
化合物C454的合成:
化合物C454-1的合成:
将中间体M2(10g,27.7mmol)、4-溴联苯(7.1g,30.5mmol)和叔丁醇钠(3.5g,36.0mmol)加入到150mL的甲苯中,搅拌溶解,用氮气充分置换,然后加入Pd2(dba)3(254mg,0.277mmol),SPhos(227mg,0.554mmol)。在氮气的保护下,升温至回流反应20h,TLC监测至原料完全反应。然后降温到室温,用饱和的氯化铵溶液萃取,水相用甲苯萃取(150mL*2),合并有机相,用饱和食盐水再洗涤一次,无水硫酸钠干燥,过滤,浓缩得粗品。继续用硅胶柱纯化得黄色固体10g。
化合物C454的合成:
将中间体C454-1(10g,19.5mmol)、3-溴联苯(5.4g,23.4mmol)和叔丁醇钠(2.4g,25.4mmol)加入到150mL的甲苯中,搅拌溶解,用氮气充分置换,然后加入Pd2(dba)3(254mg,0.277mmol),SPhos(227mg,0.554mmol)。在氮气的保护下,升温至回流反应20h,TLC监测至原料完全反应。然后降温到室温,用饱和的氯化铵溶液萃取,水相用甲苯萃取(150mL*2),合并有机相,用饱和食盐水再洗涤一次,无水硫酸钠干燥,过滤,浓缩得粗品。继续用硅胶柱纯化得黄色固体12.5g,产品用甲苯和甲醇重结晶两次,得淡黄色固体7.6g。
其余的合成实施例,可参照上述方法进行合成,所用中间体及原料可参考下表1:
表1
通过替换不同的Ar1、Ar2取代基(本领域中有时称为芳基卤代物)可以获得不同的目标化合物。需要说明的是,上述芳胺的合成方法中使用了Buchwald-Hartwig偶联方法,但是并不限于该偶联方法,本领域技术人员也可以选取其他方法,例如Stille偶联法、格氏试剂法、Kumada-Tamao等已知的方法,但不限定于这些方法,任何等同的合成方法使用能实现将取代基A1和A2连接于氨基目的,都可以根据需要选择。
器件实施例
实施方式
OLED包括位于第一电极和第二电极,以及位于电极之间的有机材料层。该有机材料又可以分为多个区域。比如,该有机材料层可以包括空穴传输区、发光层、电子传输区。
在具体实施例中,在第一电极下方或者第二电极上方可以使用基板。基板均为具有机械强度、热稳定性、防水性、透明度优异的玻璃或聚合物材料。此外,作为显示器用的基板上也可以带有薄膜晶体管(TFT)。
第一电极可以通过在基板上溅射或者沉积用作第一电极的材料的方式来形成。当第一电极作为阳极时,可以采用铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO2)、氧化锌(ZnO)等氧化物透明导电材料和它们的任意组合。第一电极作为阴极时,可以采用镁(Mg)、银(Ag)、铝(Al)、铝-锂(Al-Li)、钙(Ca)、镁-铟(Mg-In)、镁-银(Mg-Ag)等金属或合金以及它们之间的任意组合。
有机材料层可以通过真空热蒸镀、旋转涂敷、打印等方法形成于电极之上。用作有机材料层的化合物可以为有机小分子、有机大分子和聚合物,以及它们的组合。
空穴传输区位于阳极和发光层之间。空穴传输区可以为单层结构的空穴传输层(HTL),包括只含有一种化合物的单层空穴传输层和含有多种化合物的单层空穴传输层。空穴传输区也可以为包括空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)中的至少一层的多层结构。
在本发明的一方面,空穴传输区材料可以选自本发明式(1)所示的一种或多种化合物,也可以选自但不限于酞菁衍生物如CuPc、导电聚合物或含导电掺杂剂的聚合物如聚苯撑乙烯、聚苯胺/十二烷基苯磺酸(Pani/DBSA)、聚(3,4-乙撑二氧噻吩)/聚(4-苯乙烯磺酸盐)(PEDOT/PSS)、聚苯胺/樟脑磺酸(Pani/CSA)、聚苯胺/聚(4-苯乙烯磺酸盐)(Pani/PSS)、芳香胺衍生物如下面HT-1至HT-34所示的化合物;或者其任意组合。
空穴注入层位于阳极和空穴传输层之间。空穴注入层可以是单一化合物材料,也可以是多种化合物的组合。例如,空穴注入层可以采用本发明式(1)所示的一种或多种化合物,也可以采用上述HT-1至HT-34的一种或多种化合物,或者采用下述HI1-HI3中的一种或多种化合物;也可以采用这些化合物的所形成的组合物。
发光层包括可以发射不同波长光谱的的发光染料(即掺杂剂,dopant),还可以同时包括主体材料(Host)。发光层可以是发射红、绿、蓝等单一颜色的单色发光层。多种不同颜色的单色发光层可以按照像素图形进行平面排列,也可以堆叠在一起而形成彩色发光层。当不同颜色的发光层堆叠在一起时,它们可以彼此隔开,也可以彼此相连。发光层也可以是能同时发射红、绿、蓝等不同颜色的单一彩色发光层。
根据不同的技术,发光层材料可以采用荧光电致发光材料、磷光电致发光材料、热活化延迟荧光发光材料等不同的材料。在一个OLED器件中,可以采用单一的发光技术,也可以采用多种不同的发光技术的组合。这些按技术分类的不同发光材料可以发射同种颜色的光,也可以发射不同种颜色的光。
在本发明的一方面,发光层采用荧光电致发光的技术。其发光层荧光主体材料可以选自、但不限于以下所罗列的BFH-1至BFH-16的一种或多种的组合。
在本发明的一方面,发光层采用荧光电致发光的技术。其发光层荧光掺杂剂可以选自、但不限于以下所罗列的BFD-1至BFD-12的一种或多种的组合。
在本发明的一方面,发光层采用磷光电致发光的技术。其发光层主体材料选自、但不限于GPH-1至GPH-80中的一种或多种的组合。
在本发明的一方面,发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所罗列的GPD-1至GPD-47的一种或多种的组合。
在本发明的一方面,发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所罗列的RPD-1至RPD-28的一种或多种的组合。
在本发明的一方面,发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所罗列的YPD-1—YPD-11的一种或多种的组合。
在本发明的一方面,发光层采用热活化延迟荧光发光的技术。其发光层荧光掺杂剂可以选自、但不限于以下所罗列的TDE1-TDE39的一种或多种的组合。
在本发明的一方面,发光层采用热活化延迟荧光发光的技术。其发光层主体材料选自、但不限于TDH-1—TDH-24中的一种或多种的组合。
OLED有机材料层还可以包括发光层与阴极之间的电子传输区。电子传输区可以为单层结构的电子传输层(ETL),包括只含有一种化合物的单层电子传输层和含有多种化合物的单层电子传输层。电子传输区也可以为包括电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL)中的至少一层的多层结构。
本发明的一方面,电子传输层材料可以选自、但不限于以下所罗列的ET-1至ET-57的一种或多种的组合。
器件中还可以包括位于电子传输层与阴极之间的电子注入层,电子注入层材料包括但不限于以下罗列的一种或多种的组合。
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
阴极材料可以选自但不限于镁银混合物、LiF/Al、ITO等金属、金属混合物、氧化物。
实施例IVD-1中有机电致发光器件制备过程如下:
将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂中超声除油,在洁净环境下烘烤至完全除去水份,用紫外光和臭氧清洗,并用低能阳离子束轰击表面;
把上述带有阳极的玻璃基片置于真空腔内,抽真空至<1×10-5Pa,在上述阳极层膜上按先后顺序真空热蒸镀10nm的HT-4:HIL-3(97/3,w/w)混合物作为空穴注入层,60nm的化合物C6作为空穴传输层,
在空穴传输层之上真空蒸镀HT-14作为器件的电子阻挡层,蒸镀速率为0.1nm/s,蒸镀总膜厚为35nm;
磷光绿光:40nm的化合物GPH-46:GPH-3:GPD-12(100:100:20,w/w/w)三元混合物作为发光层;
25nm的化合物ET-46:ET-57(50/50,w/w)混合物作为电子传输层,1nm的LiF作为电子注入层,150nm的金属铝作为阴极。所有有机层和LiF的蒸镀总速率控制在0.1nm/秒,金属电极的蒸镀速率控制在1nm/秒。
器件实施例IVD-2~IVD-12采用和IVD-1同样的方法制作,只是把空穴传输层里的C6分别替换成如表2中实施例所示的化合物。
器件比较例CCD-1~CCD-4采用和器件实施例IVD-1同样的方法制作,只是空穴传输层里的C6分别替换成HT-4、R-1、R-2和R-3。
所用对比例化合物R-1、R-2、R-3的结构如下:
器件的测试方法:
对由上述过程制备的有机电致发光器件进行如下性能测定:
在同样亮度下,使用数字源表及亮度计测定实施例1~12以及对比例1~4中制备得到的有机电致发光器件的驱动电压和器件的寿命。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器件的亮度达到10000cd/m2时的电压即驱动电压;LT95的寿命测试如下:在初始亮度为20000cd/m2下,保持恒定的电流,使用亮度计测量有机电致发光器件的亮度降为19000cd/m2的时间,单位为小时。
有机电致发光器件性能见下表:
表2:
由上表2中的各个对比实施例与各个实施例的性能数据比较结果可见,在本发明所制备的有机电致发光器件结构中其他材料均相同的情况下,采用本发明的这类通式化合物作为空穴传输材料制备的器件,对比采用现有技术中化合物作为空穴传输材料的器件,本发明化合物提升了空穴传输性能,从而使器件的启动电压均有所降低,寿命得到提升。
本发明实施例的化合物亦可作为电子阻挡层。器件结构及制备方法与器件实施例IVD-1相同,将空穴传输层里的C6替换为HT-4,将电子阻挡层材料HT-14换成如表3中实施例中电子阻挡层所述对应材料。实施例各电子阻挡层材料信息及性能汇总于下表3。
按照上述器件测试方法测定实施例13~20以及对比例5~7中制备得到的有机电致发光器件的驱动电压和器件的寿命。器件有机电致发光器件性能见下表3:
表3
以上结果表明,本发明的新型有机材料用于有机电致发光器件的电子阻挡材料时,可以有效的降低起降电压,提高寿命。
本发明中所列举的化合物,并不限定于空穴传输材料或电子阻挡材料使用,例如C111,C139等可以作为电子阻挡层使用也可以作为空穴传输层使用。
尽管结合实施例对本发明进行了说明,但本发明并不局限于上述实施例,应当理解,在本发明构思的引导下,本领域技术人员可进行各种修改和改进,所附权利要求概括了本发明的范围
显然,上述实施例仅仅是为清楚地说明所作的举例,而并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。
Claims (8)
1.一种通式化合物,如下式(1)所示:
其中,
R和R’相同或不同,分别独立地选自取代或者未取代的下述取代基团中的一种:C1~C20的烷基、C2~C20烯基、C2~C20炔基、C1~C20的烷氧基、C6~C18的芳基、C6~C18的芳氧基或C4~C18的杂芳基,R与R’可以连接成环;
R1和R2分别独立地表示单取代到最大允许个数的取代基,R1和R2各自独立地选自氢、卤素、氰基、硝基、羟基或者选自取代或者未取代的下述取代基团中的一种:C1~C12的烷基、C1~C12硫代烷基、C2~C20烯基、C2~C20炔基、C1~C12的烷氧基、硅烷基中的一种;
A、B和C分别独立地选自取代或未取代的C6~C30的芳基氨基、取代或未取代的C3~C30的杂芳基氨基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种,且A、B中至少一个为下式(2)表示的基团:
式(2)中,Ar1和Ar2分别独立的选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;
L1和L2分别独立选自单键、取代或未取代的C6-C30的亚芳基、取代或未取代的C3~C30的亚杂芳基中的一种;
当上述基团存在取代基时,所述取代基团分别独立选自卤素、C1-C10的烷基或环烷基、C2-C10烯基、C1-C6的烷氧基或硫代烷氧基基团、C6-C30的单环芳烃或稠环芳烃基团、C3-C30的单环杂芳烃或稠环杂芳烃基团中的一种。
3.根据权利要求2所述的通式化合物,其中,通式(3-1)和(3-2)中:
L1和L2分别独立选自单键或者选自取代或未取代的下述基团:亚苯基、亚联苯基、亚萘基、亚菲基中的一种;
Ar1和Ar2分别独立选自取代或者未取代的下述基团:苯基、联苯基、萘基、菲基、芴、二苯并呋喃、二苯并噻吩中的一种。
4.根据权利要求2或3所述的通式化合物,式(3-1)中:
B、C分别独立优选为取代或者未取代的下述基团:苯、萘、蒽、苯并蒽、菲、苯并菲、芘、窟、茈、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、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、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、吩恶嗪、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、嗯唑、苯并嗯唑、萘并嗯唑、蒽并嗯唑、菲并嗯唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、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、4,5,9,10-四氮杂茈、吡嗪、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-恶二唑、1,2,4-嗯二唑、1,2,5-嗯二唑、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、吲嗪和苯并噻二唑中的一种;最优先选择苯基和萘基。
5.根据权利要求2或3所述的通式化合物,式(3-2)中,A、C分别独立优选为取代或者未取代的下述基团:苯、萘、蒽、苯并蒽、菲、苯并菲、芘、窟、茈、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、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、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、吩恶嗪、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、嗯唑、苯并嗯唑、萘并嗯唑、蒽并嗯唑、菲并嗯唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、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、4,5,9,10-四氮杂茈、吡嗪、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-恶二唑、1,2,4-嗯二唑、1,2,5-嗯二唑、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、吲嗪和苯并噻二唑中的一种;最优先选择苯基和萘基。
7.权利要求1-6中任一所述的化合物的应用,所述应用为在有机电致发光器件中作为空穴传输材料、空穴注入材料或电子阻挡材料。
8.一种有机电致发光器件,该器件包括第一电极、第二电极和插入所述第一电极和第二电极之间的一层或多层有机层,其特征在于,所述有机层中包括至少一种由权利要求1-6中任一所述的化合物。
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