CN113321659A - 一种有机电致发光材料及其器件 - Google Patents
一种有机电致发光材料及其器件 Download PDFInfo
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- CN113321659A CN113321659A CN202110606615.9A CN202110606615A CN113321659A CN 113321659 A CN113321659 A CN 113321659A CN 202110606615 A CN202110606615 A CN 202110606615A CN 113321659 A CN113321659 A CN 113321659A
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- unsubstituted
- substituent
- group substituted
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- organic electroluminescent
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- 239000000463 material Substances 0.000 title claims abstract description 49
- 150000001875 compounds Chemical group 0.000 claims abstract description 77
- 238000000034 method Methods 0.000 claims description 72
- 230000008569 process Effects 0.000 claims description 64
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- -1 phenyldimethylsilyl Chemical group 0.000 claims description 29
- 239000010410 layer Substances 0.000 claims description 17
- 239000012044 organic layer Substances 0.000 claims description 8
- 125000005264 aryl amine group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910000077 silane Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- RDBHQZLQCUALTF-UHFFFAOYSA-N 4-(4-anilinophenyl)aniline Chemical group C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC=C1 RDBHQZLQCUALTF-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006616 biphenylamine group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract description 14
- 230000005540 biological transmission Effects 0.000 abstract description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract description 7
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 230000021615 conjugation Effects 0.000 abstract description 4
- 230000007547 defect Effects 0.000 abstract description 3
- 239000006185 dispersion Substances 0.000 abstract description 3
- 230000002950 deficient Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 description 96
- 230000015572 biosynthetic process Effects 0.000 description 87
- 238000006243 chemical reaction Methods 0.000 description 69
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 238000010438 heat treatment Methods 0.000 description 35
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
- 238000003756 stirring Methods 0.000 description 33
- 229910001868 water Inorganic materials 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 238000001816 cooling Methods 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000012065 filter cake Substances 0.000 description 24
- 238000000921 elemental analysis Methods 0.000 description 22
- 238000001914 filtration Methods 0.000 description 22
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 22
- 239000012074 organic phase Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 description 17
- XRKYMMUGXMWDAO-UHFFFAOYSA-N 2-(4-morpholinyl)-6-(1-thianthrenyl)-4-pyranone Chemical compound O1C(C=2C=3SC4=CC=CC=C4SC=3C=CC=2)=CC(=O)C=C1N1CCOCC1 XRKYMMUGXMWDAO-UHFFFAOYSA-N 0.000 description 15
- 239000012046 mixed solvent Substances 0.000 description 12
- PRYCRORUYGBVEL-UHFFFAOYSA-N (5-chloro-2-methylsulfinylphenyl)boronic acid Chemical compound B(C1=C(C=CC(=C1)Cl)S(=O)C)(O)O PRYCRORUYGBVEL-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- KOAIURKUZGRJMM-UHFFFAOYSA-N 2,6-difluoropyrazine Chemical compound FC1=CN=CC(F)=N1 KOAIURKUZGRJMM-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- JXKQTRCEKQCAGH-UHFFFAOYSA-N 2,6-dibromopyrazine Chemical compound BrC1=CN=CC(Br)=N1 JXKQTRCEKQCAGH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- 238000002386 leaching Methods 0.000 description 8
- 238000010791 quenching Methods 0.000 description 8
- ZIYRDJLAJYTELF-UHFFFAOYSA-N 2-bromo-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1Br ZIYRDJLAJYTELF-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 6
- KIYKHEOWZLJZSB-UHFFFAOYSA-N 2,5-dibromopyrazine Chemical compound BrC1=CN=C(Br)C=N1 KIYKHEOWZLJZSB-UHFFFAOYSA-N 0.000 description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- ODAXNYMENLFYMY-UHFFFAOYSA-N (2-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=CC=C1B(O)O ODAXNYMENLFYMY-UHFFFAOYSA-N 0.000 description 5
- ASHCGGVQMXSLCS-UHFFFAOYSA-N (4-chloro-2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1[N+]([O-])=O ASHCGGVQMXSLCS-UHFFFAOYSA-N 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 238000012544 monitoring process Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- PHORKVSBWZGTEX-UHFFFAOYSA-N (2-methylsulfinylphenyl)boronic acid Chemical compound CS(=O)C1=CC=CC=C1B(O)O PHORKVSBWZGTEX-UHFFFAOYSA-N 0.000 description 3
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 3
- CVYLRXWWSGNWHX-UHFFFAOYSA-N (4-chloro-2-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC(Cl)=CC=C1B(O)O CVYLRXWWSGNWHX-UHFFFAOYSA-N 0.000 description 3
- XPWYTZGWNXDFRE-UHFFFAOYSA-N 2-bromo-5-fluoropyrazine Chemical compound FC1=CN=C(Br)C=N1 XPWYTZGWNXDFRE-UHFFFAOYSA-N 0.000 description 3
- ZUNRJFKRWLCVSX-UHFFFAOYSA-N 2-bromo-6-fluoropyrazine Chemical compound FC1=CN=CC(Br)=N1 ZUNRJFKRWLCVSX-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- RLGKZWXCACVYRU-UHFFFAOYSA-N (2-methoxycarbonylphenoxy)boronic acid Chemical compound COC(=O)C1=CC=CC=C1OB(O)O RLGKZWXCACVYRU-UHFFFAOYSA-N 0.000 description 2
- PURYLRLRXKALOG-UHFFFAOYSA-N (5-chloro-2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=CC=C1[N+]([O-])=O PURYLRLRXKALOG-UHFFFAOYSA-N 0.000 description 2
- FXQMGPWUMNMGHH-UHFFFAOYSA-N 2,5-difluoropyrazine Chemical compound FC1=CN=C(F)C=N1 FXQMGPWUMNMGHH-UHFFFAOYSA-N 0.000 description 2
- FMRKYXVZQWHGDA-UHFFFAOYSA-N 2-bromo-5-chlorophenol Chemical compound OC1=CC(Cl)=CC=C1Br FMRKYXVZQWHGDA-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 108010017443 B 43 Proteins 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- KCWQKEWVJWAKEZ-UHFFFAOYSA-N (1-phenylbenzimidazol-2-yl)boronic acid Chemical compound OB(O)C1=NC2=CC=CC=C2N1C1=CC=CC=C1 KCWQKEWVJWAKEZ-UHFFFAOYSA-N 0.000 description 1
- RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-UHFFFAOYSA-N 0.000 description 1
- KWZAIOOHESKUSV-UHFFFAOYSA-N (10-phenylanthracen-9-yl)oxyboronic acid Chemical compound C12=CC=CC=C2C(OB(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 KWZAIOOHESKUSV-UHFFFAOYSA-N 0.000 description 1
- MRBZYVMZUBUDAX-UHFFFAOYSA-N (3,5-diphenylphenyl)boronic acid Chemical compound C=1C(B(O)O)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 MRBZYVMZUBUDAX-UHFFFAOYSA-N 0.000 description 1
- RGNJFORIDGDIJI-UHFFFAOYSA-N (4-chloro-2-methylsulfinylphenyl)boronic acid Chemical compound ClC1=CC(=C(C=C1)B(O)O)S(=O)C RGNJFORIDGDIJI-UHFFFAOYSA-N 0.000 description 1
- MBYOBTPZNDJPCC-UHFFFAOYSA-N (4-phenylphenoxy)boronic acid Chemical compound C1=CC(OB(O)O)=CC=C1C1=CC=CC=C1 MBYOBTPZNDJPCC-UHFFFAOYSA-N 0.000 description 1
- XSAOVBUSKVZIBE-UHFFFAOYSA-N (9-phenylcarbazol-2-yl)boronic acid Chemical compound C=1C(B(O)O)=CC=C(C2=CC=CC=C22)C=1N2C1=CC=CC=C1 XSAOVBUSKVZIBE-UHFFFAOYSA-N 0.000 description 1
- GGUYHZZGZZAVDH-UHFFFAOYSA-N 1,3-benzoxazol-2-ylboronic acid Chemical compound C1=CC=C2OC(B(O)O)=NC2=C1 GGUYHZZGZZAVDH-UHFFFAOYSA-N 0.000 description 1
- PTPGZCQGDXUUAH-UHFFFAOYSA-N 2-bromo-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Br)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 PTPGZCQGDXUUAH-UHFFFAOYSA-N 0.000 description 1
- INJYATWDDJSOIP-UHFFFAOYSA-N 2-bromo-4,6-diphenylpyridine Chemical compound N=1C(Br)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 INJYATWDDJSOIP-UHFFFAOYSA-N 0.000 description 1
- GPGIIKKUKINTGW-UHFFFAOYSA-N 2-bromo-4,6-diphenylpyrimidine Chemical compound N=1C(Br)=NC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 GPGIIKKUKINTGW-UHFFFAOYSA-N 0.000 description 1
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 1
- RHPVVNRNAHRJOQ-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C)C=C1 RHPVVNRNAHRJOQ-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- RDMFHRSPDKWERA-UHFFFAOYSA-N 5H-Pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=CC=C3NC2=C1 RDMFHRSPDKWERA-UHFFFAOYSA-N 0.000 description 1
- RAPHUPWIHDYTKU-WXUKJITCSA-N 9-ethyl-3-[(e)-2-[4-[4-[(e)-2-(9-ethylcarbazol-3-yl)ethenyl]phenyl]phenyl]ethenyl]carbazole Chemical compound C1=CC=C2C3=CC(/C=C/C4=CC=C(C=C4)C4=CC=C(C=C4)/C=C/C=4C=C5C6=CC=CC=C6N(C5=CC=4)CC)=CC=C3N(CC)C2=C1 RAPHUPWIHDYTKU-WXUKJITCSA-N 0.000 description 1
- SPRWGTRUTFPHEY-UHFFFAOYSA-N B(O)(O)OC1=NC2=CC=CC=C2O1 Chemical compound B(O)(O)OC1=NC2=CC=CC=C2O1 SPRWGTRUTFPHEY-UHFFFAOYSA-N 0.000 description 1
- IBQPXJIZNAUYCJ-UHFFFAOYSA-N ClC1=CC(=C(C=C1)OB(O)O)[N+](=O)[O-] Chemical compound ClC1=CC(=C(C=C1)OB(O)O)[N+](=O)[O-] IBQPXJIZNAUYCJ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- IUTDVGSJRKTQPM-UHFFFAOYSA-N [4-(1,3-benzothiazol-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NC2=CC=CC=C2S1 IUTDVGSJRKTQPM-UHFFFAOYSA-N 0.000 description 1
- YRIZQOGJMTUTBB-UHFFFAOYSA-N [4-(2-phenylbenzimidazol-1-yl)phenoxy]boronic acid Chemical compound C1(=CC=CC=C1)C1=NC2=C(N1C1=CC=C(C=C1)OB(O)O)C=CC=C2 YRIZQOGJMTUTBB-UHFFFAOYSA-N 0.000 description 1
- RCOAUYBPVRIYBG-UHFFFAOYSA-N [4-(2-phenylbenzimidazol-1-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N1C2=CC=CC=C2N=C1C1=CC=CC=C1 RCOAUYBPVRIYBG-UHFFFAOYSA-N 0.000 description 1
- QHZHWFKZIRMHRT-UHFFFAOYSA-N [4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 QHZHWFKZIRMHRT-UHFFFAOYSA-N 0.000 description 1
- TWWQCBRELPOMER-UHFFFAOYSA-N [4-(n-phenylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 TWWQCBRELPOMER-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- PXFBSAPVQIYGFM-UHFFFAOYSA-N imidazo[1,2-a]pyridin-3-ylboronic acid Chemical compound C1=CC=CN2C(B(O)O)=CN=C21 PXFBSAPVQIYGFM-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
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- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D491/04—Ortho-condensed systems
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Abstract
本发明涉及光电材料应用科技领域,公开了一种有机电致发光材料及其器件。本发明化合物核心结构含缺电子性的吡嗪,通过对吡嗪两侧并入供电子性的芳环,化合物核心结构电子云密度增加,共轭扩大,化合物可以获得较高的荧光量子效率及较强的刚性,通过对核心结构侧边键接电子传输型基团或空穴传输型基团,化合物可以实现较好的激子分散及能量传播,有效解决了目前蓝光发光材料发光效率、发光颜色、寿命等方面的缺陷,从而使得OLED器件在驱动电压、电流效率、寿命等方面具有优良的综合性能,作为发光材料在蓝光器件中具有显著的应用价值。
Description
技术领域
本发明属于光电材料应用科技领域,具体涉及一种有机电致发光材料及其器件。
背景技术
随着信息时代的发展,具有高效、节能、轻薄等优良特性的机电致发光平板显示器(OLEDs)及大面积白光照明越来越受到人们的关注。
按照发光原理,OLED发光材料主要分为荧光材料、磷光材料两类。传统荧光材料由于无法利用三线态激子,其效率难以满足高效器件性能的需求。含铱、铂等贵金属的磷光材料以及新型荧光材料可以充分利用三线态激子能量,实现100%内量子效率的高效发光,然而,现有磷光和新型荧光材料的发光器件往往存在效率滚降大、工作寿命不足、器件结构复杂等一个或多个缺点,特别是对于蓝光材料而言。宽带隙的蓝光材料具有较高的能量,可以通过能量转移到低能量的绿光、黄光和红光等有机发光材料,从而制备全发光的有机电致发光器件,然而,蓝光材料在器件中电荷注入困难,材料设计过程中的π共轭容易导致较强的分子内电荷转移从而引起材料发光红移,很难兼顾发光效率和发光颜色等性能。
吡嗪结构具有较强的缺电子性,可以有效降低化合物材料的HOMO能级,从而赋予发光材料较宽的能级带隙,通过芳环对包含吡嗪的化合物核心结构进行共轭扩大的同时还可以增强分子刚性,更有利于材料的无针孔高质量成膜,另外,在核心结构侧边适当接入一些空穴或电子传输型的基团,更有利于能量传输,提高发光材料的电荷传输效率及电荷传输平衡性。
发明内容
本发明的目的在于提供一种有机电致发光材料及其器件,解决目前蓝光发光材料发光效率、发光颜色、寿命等方面的缺陷,从而使得OLED器件在驱动电压、电流效率、寿命等方面具有优良的综合性能。
本发明第一个方面提供了一种由下述化合物结构通式(1)或(2)所表示的机电致发光材料:
其中,
X选自O、S、N(R9)、C(R10)(R11);
Y选自O、S、N(R12)、C(R13)(R14);
Z1及Z2各自独立的选自C或N,并且至少一个为N,
R1至R8彼此相同或不同,各自独立地选自氢、氟基、硝基、氰基、C1~20的烷基、C1~20的烷氧基、C1~20的烷硫基、C1~20的硅烷基、C6~50的芳基、C3~50的杂芳基、C6~50的芳胺基、C6~50的芳氧基、C6~50的芳硫基,
R9至R11各自独立地选自C1~20的烷基、C6~50的芳基、C3~50的杂芳基、C6~50的芳胺基,R10与R11彼此独立,或通过单键连接;
R12至R14各自独立地选自C1~20的烷基、C6~50的芳基、C3~50的杂芳基、C6~50的芳胺基,R13与R14彼此独立,或通过单键连接。
进一步的,所述式(1)进一步表示为下列式(1-1)至式(1-10)所示化合物:
所述式(2)进一步表示为下列式(2-1)至式(2-10)所示化合物:
进一步的,所述Z1及Z2皆为N。
进一步的,所述R1至R8中之一选自C1~20的烷基、C1~20的烷氧基、C1~20的烷硫基、C1~20的硅烷基、C6~50的芳基、C3~50的杂芳基、C6~50的芳胺基、C6~50的芳氧基、C6~50的芳硫基,
所述R1至R8中剩余基团皆为氢。
进一步的,所述C1~20的烷基选自:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基中的一种;
所述C1~20的烷氧基选自:甲氧基、乙氧基中的一种;
所述C1~20的烷硫基选自:甲硫基、乙硫基中的一种;
所述C1~20的硅烷基选自:三甲基硅烷基、苯基二甲基硅烷基、联苯基二甲基硅烷基、甲基二苯基硅烷基中的一种;
所述C6~50的芳基选自:由取代基取代或未取代的苯基、由取代基取代或未取代的联苯基、由取代基取代或未取代的三联苯基、由取代基取代或未取代的萘基、由取代基取代或未取代的蒽基、由取代基取代或未取代的菲基、由取代基取代或未取代的芘基、由取代基取代或未取代的苯并菲基、由取代基取代或未取代的芴基、由取代基取代或未取代的螺二芴基中的至少一种;
所述C3~50的杂芳基选自:由取代基取代或未取代的吡啶基、由取代基取代或未取代的嘧啶基、由取代基取代或未取代的吡嗪基、由取代基取代或未取代的三嗪基、由取代基取代或未取代的吲哚基、由取代基取代或未取代的苯并呋喃基、由取代基取代或未取代的苯并噻吩基、由取代基取代或未取代的苯并噁唑基、由取代基取代或未取代的苯并噻唑基、由取代基取代或未取代的咔唑基、由取代基取代或未取代的苯基咔唑基、由取代基取代或未取代的咔唑基苯基、由取代基取代或未取代的二苯并呋喃基、由取代基取代或未取代的二苯并噻吩基中的至少一种;
所述C6~50的芳胺基选自:由取代基取代或未取代的二苯胺基、由取代基取代或未取代的N-苯基联苯胺基、由取代基取代或未取代的二联苯胺基、由取代基取代或未取代的N-苯基萘胺基、由取代基取代或未取代的二萘胺基、由取代基取代或未取代的三苯胺基中的至少一种;
其中:取代基选自:氰基、氟基、硝基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、苯基中的一种或其组合。
进一步的,所述R1至R8中之一选自以下结构式:
优选的,所述有机电致发光材料选自以下任意一种结构式所示化合物:
本发明第二个方面提供了一种有机电致发光器件,主要包括阴极、阳极和两电极之间的有机层,或者主要包括出光层、阴极、阳极和两电极之间的有机层,所述两电极之间的有机层包含上述的有机电致发光材料。
进一步的,所述两电极之间的有机层包括发光层,所述发光层包含上述的有机电致发光材料。
进一步的,所述发光层由发光主体和发光客体组成,所述发光主体包含上述的有机电致发光材料。
本发明提供的有机电致发光材料化合物的核心结构包含吡嗪,侧边键接强吸电子型或强供电子型基团。吡嗪结构具有缺电子性,可以有效降低化合物材料的HOMO能级,从而满足深蓝光材料的宽能级带隙需求,通过对吡嗪的两侧并入供电子性的芳环,核心结构电子云密度增加,共轭扩大,因此化合物分子可以获得较高的荧光量子效率,而且,化合物的分子刚性也得以增强,热稳定性提高。此外,强吸电子型或强供电子型侧基的引入不但可以增大化合物分子量,化合物玻璃化转变温度进一步提高,还可以有效减少化合物分子间的相互作用,减少分子间的紧密堆集,而且,化合物既能获得较好的激子分散能力,又能实现较好的能量传输,从而使得本发明实现高效的深蓝光发射,在器件的驱动电压、电流效率、寿命等综合性能上取得显著进步。
具体实施方式
应当理解的是,此处所描述的具体实施方式仅用于说明和解释本发明,并不用于限制本发明。
合成实施例1:合成化合物(A-5)
S1.在1L反应瓶中,加入2-溴-4-氯苯酚(33.19g,160mmol)、2,6-二氟吡嗪(19.15g,165mmol)、碳酸钾(33.12g,240mmol),按照2-溴-4-氯苯酚的重量计,加入10-15倍体积的N,N-二甲基甲酰胺,通入氮气排空气,加热至145℃,搅拌反应2-4h,然后冷却至室温,向反应液中加入水,过滤,滤饼用乙醇和/或四氢呋喃进行纯化,即可得到31.57g中间体a1,收率65%;
S2.在500mL反应瓶中,加上述中间体a1(24.28g,80mmol)、2-溴苯酚(13.84g,80mmol)、碳酸钾(16.59g,120mmol),按照中间体a1的重量计,加入10-15倍体积的N,N-二甲基甲酰胺,通入氮气排空气,加热至145℃,搅拌反应2-4h,然后冷却至室温,向反应液中加入水,过滤,滤饼用乙醇和/或四氢呋喃进行纯化,即可得到24.47g中间体b1,收率68%;
S3.在500mL反应瓶中,加上述中间体b1(18.26g,40mmol),按照中间体b1的重量计,加入10倍体积的二甲基乙酰胺,通入氮气排空气,加入醋酸钯(0.27g,1.2mmol)、三环己基膦(0.34g,1.2mmol),升温至160℃,搅拌反应2-4h,液相监测原料基本无剩余,停止加热,冷却至室温,加水,过滤,滤饼用乙醇和/或四氢呋喃纯化,即可得6.13g中间体c1,收率52%;
S4.在250mL反应瓶中,加入镁(0.55g,23mmol)、上述中间体c1(5.89g,20mmol),按照中间体c1的重量计,加入10-15倍体积的四氢呋喃,通入氮气,升温至65℃反应2-4h后,降温至0℃-5℃,向反应瓶中缓慢滴加2-溴-4,6-二苯基-1,3,5-三嗪的四氢呋喃溶液(6.24g,20mmol),搅拌反应8-16h,然后恢复至室温,向反应液中加入稀盐酸猝灭反应,分液,水相用四氢呋喃萃取后,与有机相合并浓缩,与滤饼一起用10:1的石油醚与二氯甲烷在硅胶柱中淋洗,浓缩,即可得到6.19g化合物(A-5),收率63%。
质谱仪MALDI-TOF-MS(m/z)=491.5063,理论分子量:491.5100,元素分析:理论值:C31H17N5(%):C75.75;H3.49;N14.25;实测值:C75.76;H3.48;N14.26。
合成实施例2:合成化合物(A-6)
S1.合成过程按照合成实施例1的步骤S1,即可得30.11g中间体a2,收率62%;
S2.将合成实施例1步骤S2中的中间体a1替换为中间体a2(24.28g,80mmol),其他合成过程按照合成实施例1的步骤S2,即可得24.10g中间体b2,收率66%;
S3.将合成实施例1步骤S3中的中间体b1替换为中间体b2(18.26g,40mmol),其他合成过程按照合成实施例1的步骤S3,即可得6.72g中间体c2,收率57%;
S4.将合成实施例1步骤S4中的中间体c1替换为中间体c2(5.89g,20mmol)、2-溴-4,6-二苯基-1,3,5-三嗪替换为2-溴-4,6-二苯基嘧啶(6.22g,20mmol),其他合成过程按照合成实施例3的步骤S4,即可得到5.89g化合物(A-6),收率60%。
质谱仪MALDI-TOF-MS(m/z)=490.5248,理论分子量:490.5220,元素分析:理论值:C32H18N4(%):C78.36;H3.70;N11.42;实测值:C78.35;H3.68;N11.44。
合成实施例3:合成化合物(A-11)
S1.在1L反应瓶中,加入5-氯-2-(甲基亚磺酰基)苯基硼酸(34.95g,160mmol)、2,6-二溴吡嗪(39.25g,165mmol)、碳酸钾(44.16g,320mmol)、400mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(0.92g,0.8mmol),加热至85℃,搅拌反应6-12h,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用乙醇和/或四氢呋喃进行纯化,即可得33.95g中间体a3,收率64%;
S2.在500mL反应瓶中,加入上述中间体a3(27.19g,82mmol)、2-(甲基亚磺酰基)苯基硼酸(14.72g,80mmol)、碳酸钾(22.08g,160mmol)、250mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(0.46g,0.4mmol),加热至85℃,搅拌反应6-12h,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用乙醇和/或四氢呋喃进行纯化,即可得21.46g中间体b3,收率66%;
S3.在250mL反应瓶中,加入上述中间体b3(19.55g,50mmol),室温下搅拌24h,然后加入150mL体积比为8:1的水/吡啶混合溶剂,110℃下搅拌30min,然后冷却至室温,使用二氯甲烷进行萃取,将所得物质用硫酸镁干燥并减压蒸馏,然后,将由此获得的残留物柱分离,即可得6.54g中间体c3,收率40%;
S4.在100mL反应瓶中,加入上述中间体c3(3.27g,10mmol)、(10-苯基蒽-9-基)硼酸(2.98g,10mmo)、碳酸钾(2.76g,20mmol)、50mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(0.06g,0.05mmol),加热至85℃,搅拌反应6-12h,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用10:1的石油醚与二氯甲烷在硅胶柱中淋洗,浓缩,即可得到3.81g化合物(A-11),收率70%。
质谱仪MALDI-TOF-MS(m/z)=544.6957,理论分子量:544.6900,元素分析:理论值:C36H20N2(%):C79.38;H3.70;N5.14;实测值:C78.36;H3.69;N5.16。
合成实施例4:合成化合物(A-24)
S1.将合成实施例3步骤S1中的5-氯-2-(甲基亚磺酰基)苯基硼酸替换成(4-氯-2-(甲酯基)苯基)硼酸(34.31g,160mmol),其他合成过程按照合成实施例1的步骤S1,即可得31.45g中间体a4,收率60%;
S2.将合成实施例3步骤S2中的中间体a3替换成中间体a4(26.20g,82mmol)、2-(甲基亚磺酰基)苯基硼酸替换成(2-(甲酯基)苯基)硼酸(14.40g,80mmol),其他合成过程按照合成实施例3的步骤S2,即可得到19.60g中间体b4,收率64%;
S3.在500mL反应瓶中,加上述中间体b4(15.31g,40mmol)、3mol/L的甲基溴化镁(107mL,320mmol)、按照中间体b4的重量计,加入10倍体积的四氢呋喃,通入氮气排空气,升温至65℃,搅拌反应2-4h,冷却至室温,加入饱和的氯化铵猝灭反应,分液,水相用四氢呋喃萃取后,与有机相一起浓缩,用乙醇和/或四氢呋喃进行纯化,即可得10.41g中间体c4,收率68%;
S4.在500mL反应瓶中,加上述中间体c4(7.66g,20mmol)、220mL体积比为10:1的乙酸/浓盐酸溶剂,升温至85℃,搅拌反应2-4h,液相监测原料基本无剩余,停止加热,加入水猝灭反应,过滤,滤饼用乙醇和/或四氢呋喃纯化,即可得4.58g中间体d4,收率66%;
S5.在100mL反应瓶中加入上述中间体d4(3.47g,10mmol)、苯并噁唑-2-基硼酸(1.63g,10mmol)、碳酸钾(2.76g,20mmol)、50mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(0.06g,0.05mmol),加热至85℃,搅拌反应6-12h,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用10:1的石油醚与二氯甲烷在硅胶柱中淋洗,浓缩,即可得到3.18g化合物(A-24),收率74%。
质谱仪MALDI-TOF-MS(m/z)=429.5175,理论分子量:429.5230,元素分析:理论值:C29H23N3(%):C81.09;H 5.40;N9.78;实测值:C81.10;H 5.38;N9.77。
合成实施例5:合成化合物(A-28)
S1.将合成实施例3步骤S1中的5-氯-2-(甲基亚磺酰基)苯基硼酸替换成(5-氯-2-硝基苯基)硼酸(32.22g,160mmol),其他合成过程按照合成实施例3的步骤S1,即可得31.70g中间体a5,收率63%;
S2.将合成实施例3步骤S2中的中间体a3替换成中间体a5(25.16g,82mmol)、2-(甲基亚磺酰基)苯基硼酸替换成(2-硝基苯基)硼酸(13.35g,80mmol),其他合成过程按照合成实施例3的步骤S1,即可得到19.69g中间体b5,收率69%;
S3.在250mL反应瓶中,加入上述中间体b5(14.27g,40mmol)、亚磷酸三乙酯(66.46g,400mmol)、氯苯(49.02g,400mmol),加热回流反应12h,冷却至室温,加入水,用二氯甲烷萃取后分液,有机相浓缩,用乙醇和/或四氢呋喃纯化,即可得6.09g中间体c5,收率52%;
S4.在250mL反应瓶中,加入上述中间体c5(5.85g,20mmol)、溴苯(7.07g,45mmol)、碳酸钾5.52g(40mmol)和100mL N,N-二甲基乙酰胺。通入氮气,加入碘化亚铜0.76g(4mmol)和邻菲啰啉1.44g(8mmol),加热回流搅拌8h,然后冷却至室温,向反应液中加入水,过滤,滤饼用乙醇和/或四氢呋喃进行纯化,得到6.32g中间体d5,收率71%;
S5.在100mL反应瓶中,加入上述中间体d5(4.45g,10mmol)、二对甲苯基胺(2.37g,12mmol)、碳酸钾2.76g(20mmol)和50mL N,N-二甲基乙酰胺。通入氮气,加入碘化亚铜0.19g(1mmol)和邻菲啰啉0.36g(2mmol),加热回流搅拌8h,然后冷却至室温,向反应液中加入水,过滤,滤饼用10:1的石油醚与二氯甲烷在硅胶柱中淋洗,浓缩,得到4.66g化合物(A-28),收率77%。
质谱仪MALDI-TOF-MS(m/z)=605.7536,理论分子量:605.7450,元素分析:理论值:C42H31N5(%):C83.28;H5.16;N11.56;实测值:C83.27;H5.15;N11.57。
合成实施例6:合成化合物(A-37)
S1.将合成实施例1步骤S1中的2-溴-4-氯苯酚替换为2-溴-5-氯苯酚(33.19g,160mmol)、2,6-二氟吡嗪替换为2-溴-5-氟吡嗪(28.32g,160mmol),其他合成过程按照合成实施例1的步骤S1,即可得43.15g中间体a6,收率74%;
S2.在500mL反应瓶中,加上述中间体a6(29.15g,80mmol),按照中间体a6的重量计,加入10倍体积的二甲基乙酰胺,通入氮气排空气,加入醋酸钯(0.36g,1.6mmol)、三环己基膦(0.45g,1.6mmol),升温至160℃,搅拌反应2-4h,液相监测原料基本无剩余,停止加热,冷却至室温,加水,过滤,滤饼用乙醇和/或四氢呋喃纯化,即可得12.47g中间体b6,收率55%;
S3.在250mL反应瓶中,加上述中间体b6(11.62g,41mmol)、2-(甲基亚磺酰基)苯基硼酸(7.36g,40mmol)、碳酸钾(11.04g,80mmol),100mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(0.23g,0.2mmol),加热至85℃,搅拌反应6-12h,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用乙醇和/或四氢呋喃进行纯化,即可得到8.91g中间体c6,收率65%;
S4.在250mL反应瓶中,加入上述中间体c6(6.86g,20mmol),室温下搅拌24h,然后加入150mL体积比为8:1的水/吡啶混合溶剂,110℃下搅拌30min,然后冷却至室温,使用二氯甲烷进行萃取,将所得物质用硫酸镁干燥并减压蒸馏,然后,将由此获得的残留物柱分离,即可得2.8g中间体d6,收率45%;
S5.在50mL反应瓶中,加入上述中间体d6(1.56g,5mmol)、5氢-吡啶并[4,3-b]吲哚(1.01g,6mmol)、碳酸钾1.38g(10mmol)和20mL N,N-二甲基乙酰胺。通入氮气,加入碘化亚铜0.1g(0.5mmol)和邻菲啰啉0.18g(1mmol),加热回流搅拌8h,然后冷却至室温,向反应液中加入水,过滤,滤饼用10:1的石油醚与二氯甲烷在硅胶柱中淋洗,浓缩,得到1.75g化合物(A-37),收率79%。
质谱仪MALDI-TOF-MS(m/z)=442.4861,理论分子量:442.4960,元素分析:理论值:C27H14N4(%):C73.29;H3.19;N12.66;实测值:C73.28;H3.20;N12.64。
合成实施例7:合成化合物(A-45)
S1.将合成实施例1步骤S1中的2-溴-4-氯苯酚替换为2-溴-5-氯苯酚(33.19g,160mmol)、2,6-二氟吡嗪替换为2-溴-5-氟吡嗪(28.32g,160mmol),其他合成过程按照合成实施例1的步骤S1,即可得41.39g中间体a7,收率71%;
S2.将合成实施例6步骤S2中的a6替换成a7(29.15g,80mmol),其他合成过程按照合成实施例6的步骤S2,即可得11.95g中间体b7,收率53%;
S3.将合成实施例6步骤S3的b6替换成b7(11.62g,41mmol),2-(甲基亚磺酰基)苯基硼酸替换成(2-(甲酯基)苯基)硼酸(7.20g,40mmol),其他合成过程按照合成实施例6的步骤S3,即可得到8.40g中间体c7,收率62%;
S4.在250mL反应瓶中,加上述中间体c7(6.78g,20mmol)、3mol/L的甲基溴化镁(26.67mL,80mmol)、按照中间体c7的重量计,加入10倍体积的四氢呋喃,通入氮气排空气,升温至65℃,搅拌反应2-4h,冷却至室温,加入饱和的氯化铵猝灭反应,分液,水相用四氢呋喃萃取后,与有机相一起浓缩,用乙醇和/或四氢呋喃进行纯化,即可得5.01g中间体d7,收率74%;
S5.在250mL反应瓶中,加上述中间体d7(3.39g,10mmol)、100mL体积比为10:1的乙酸/浓盐酸溶剂,升温至85℃,搅拌反应2-4h,液相监测原料基本无剩余,停止加热,加入水猝灭反应,过滤,滤饼用乙醇和/或四氢呋喃纯化,即可得2.25g中间体e7,收率70%;
S6.在50mL反应瓶中,加入上述中间体e7(1.6g,5mmol)、[1,1'-联苯基]-4-基硼酸(0.99g,5mmol)、碳酸钾(1.38g,10mmol)、20mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(0.03g,0.03mmol),加热至85℃,搅拌反应6-12h,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用10:1的石油醚与二氯甲烷在硅胶柱中淋洗,浓缩,即可得到1.65g化合物(A-45),收率75%。
质谱仪MALDI-TOF-MS(m/z)=438.5356,理论分子量:438.5300,元素分析:理论值:C31H22N2(%):C84.91;H5.06;N6.39;实测值:C84.91;H5.07;N6.38。
合成实施例8:合成化合物(A-68)
S1.将合成实施例1步骤S1中的2-溴-4-氯苯酚替换成2-溴苯酚(27.68g,160mmol),2,6-二氟吡嗪替换成2-溴-5-氟吡嗪(28.32g,160mmol),其他合成过程按照合成实施例1的步骤S1,即可得40.12g中间体a8,收率76%;
S2.将合成实施例6步骤S2中的a6替换成a8(26.40g,80mmol),其他合成过程按照合成实施例6的步骤S2,即可得11.16g中间体b8,收率56%;
S3.将合成实施例6步骤S3的b6替换成b8(10.21g,41mmol),2-(甲基亚磺酰基)苯基硼酸替换成(4-氯-2-硝基苯基)硼酸(8.05g,40mmol),其他合成过程按照合成实施例6的步骤S3,即可得到8.73g中间体c8,收率67%;
S4.在50mL反应瓶中,加入上述中间体c8(6.51g,20mmol)、亚磷酸三乙酯(16.62g,100mmol)、氯苯(12.26g,100mmol),加热回流反应12h,冷却至室温,加入水,用二氯甲烷萃取后分液,有机相浓缩,用乙醇和/或四氢呋喃纯化,即可得3.41g中间体d8,收率58%;
S5.在100mL反应瓶中,加入上述中间体d8(2.94g,10mmol)、溴苯(1.73g,11mmol)、碳酸钾2.76g(20mmol)和50mL N,N-二甲基乙酰胺。通入氮气,加入碘化亚铜0.19g(1mmol)和邻菲啰啉0.36g(2mmol),加热回流搅拌8h,然后冷却至室温,向反应液中加入水,过滤,滤饼用乙醇和/或四氢呋喃进行纯化,得到2.74g中间体e8,收率74%;
S6.将合成实施例7步骤S6中的中间体e7替换成e8(1.85g,5mmol),[1,1'-联苯基]-4-基硼酸替换成咪唑并[1,2-b]哒嗪-2-基硼酸(0.81g,5mmol),其他合成过程按照合成实施例7的步骤S6,即可得1.77g化合物A-68,收率78%。
质谱仪MALDI-TOF-MS(m/z)=452.4697,理论分子量:452.4770,元素分析:理论值:C28H16N6(%):C74.33;H3.56;N18.57;实测值:C74.31;H3.54;N18.58。
合成实施例9:合成化合物(A-73)
S1.将合成实施例3步骤S1中的5-氯-2-(甲基亚磺酰基)苯基硼酸替换成(4-氯-2-(甲基亚磺酰基)苯基)硼酸(34.95g,160mmol),其他合成过程按照合成实施例3的步骤S1,即可得32.89g中间体a9,收率62%;
S2.在500mL反应瓶中,加入上述中间体a9(33.16g,100mmol),室温下搅拌24h,然后加入300mL体积比为8:1的水/吡啶混合溶剂,110℃下搅拌30min,然后冷却至室温,使用二氯甲烷进行萃取,将所得物质用硫酸镁干燥并减压蒸馏,然后,将由此获得的残留物柱分离,即可得12.88g中间体b9,收率43%;
S3.将合成实施例6步骤S3的b6替换成b9(12.28g,41mmol),2-(甲基亚磺酰基)苯基硼酸替换成(2-(甲酯基)苯基)硼酸(7.20g,40mmol),其他合成过程按照合成实施例6的步骤S3,即可得到9.51g中间体c9,收率67%;
S4.将合成实施例7步骤S4的c7替换成c9(7.10g,20mmol),其他合成过程按照合成实施例7的步骤S4,即可得到5.39g中间体d9,收率76%;
S5.将合成实施例7步骤S5的d7替换成d9(3.55g,10mmol),其他合成过程按照合成实施例7的步骤S5,即可得到2.46g中间体e9,收率73%;
S6.将合成实施例7步骤S6的e7替换成e9(1.68g,5mmol)、[1,1'-联苯基]-4-基硼酸替换成(4-(苯并噻唑-2-基)苯基)硼酸(1.28g,5mmol),其他合成过程按照合成实施例7的步骤S6,即可得到1.82g化合物A-73,收率71%。
质谱仪MALDI-TOF-MS(m/z)=511.6559,理论分子量:511.6610,元素分析:理论值:C32H21N3(%):C75.12;H4.14;N8.21;实测值:C75.13;H4.13;N8.22。
合成实施例10:合成化合物(A-88)
S1.将合成实施例3步骤S1中的5-氯-2-(甲基亚磺酰基)苯基硼酸替换成(2-(甲基亚磺酰基)苯基)硼酸(29.44g,160mmol),其他合成过程按照合成实施例3的步骤S1,即可得30.91g中间体a10,收率65%;
S2.将合成实施例9步骤S2中的中间体a9替换成a10(29.72g,100mmol),其他合成过程按照合成实施例9的步骤S2,即可得12.20g中间体b10,收率46%;
S3.将合成实施例6步骤S3中的中间体b6替换成b10(10.87g,41mmol)、2-(甲基亚磺酰基)苯基硼酸替换成(4-氯-2-硝基苯基)硼酸(8.05g,40mmol),其他合成过程按照合成实施例6的步骤S3,即可得9.43g中间体c10,收率69%;
S4.将合成实施例8步骤S4中的中间体c8替换成c10(6.84g,20mmol),其他合成过程按照合成实施例8的步骤S4,即可得3.41g中间体d10,收率55%;
S5.将合成实施例8步骤S5中的中间体d8替换成d10(3.10g,10mmol),其他合成过程按照合成实施例8的步骤S5,即可得2.97g中间体e10,收率77%;
S6.在50mL反应瓶中,加入上述中间体e10(1.93g,5mmol)、9氢-咔唑(1.00g,6mmol)、碳酸钾1.38g(10mmol)和20mL N,N-二甲基乙酰胺。通入氮气,加入碘化亚铜0.1g(0.5mmol)和邻菲啰啉0.18g(1mmol),加热回流搅拌8h,然后冷却至室温,向反应液中加入水,过滤,滤饼用10:1的石油醚与二氯甲烷在硅胶柱中淋洗,浓缩,得到2.12g化合物(A-88),收率82%。
质谱仪MALDI-TOF-MS(m/z)=516.6274,理论分子量:516.6220,元素分析:理论值:C34H20N4(%):C79.05;H3.90;N10.85;实测值:C79.05;H3.91;N10.84。
合成实施例11:合成化合物(A-104)
S1.在1L反应瓶中,加入(2-(甲酯基)苯基)硼酸(57.59g,320mmol)、2,6-二溴吡嗪(78.50g,330mmol)、碳酸钾(88.32g,640mmol)、600mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(1.85g,1.6mmol),加热至85℃,搅拌反应6-12h,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用乙醇和/或四氢呋喃进行纯化,即可得60.03g中间体a11,收率64%;
S2.在1L反应瓶中,加上述中间体a11(46.89g,160mmol)、3mol/L的甲基溴化镁(213.33mL,640mmol)、按照中间体a11的重量计,加入10倍体积的四氢呋喃,通入氮气排空气,升温至65℃,搅拌反应2-4h,冷却至室温,加入饱和的氯化铵猝灭反应,分液,水相用四氢呋喃萃取后,与有机相一起浓缩,用乙醇和/或四氢呋喃进行纯化,即可得33.77g中间体b11,收率72%;
S3.在500mL反应瓶中,加上述中间体b11(23.45g,80mmol)、220mL体积比为10:1的乙酸/浓盐酸溶剂,升温至85℃,搅拌反应2-4h,液相监测原料基本无剩余,停止加热,加入水猝灭反应,过滤,滤饼用乙醇和/或四氢呋喃纯化,即可得14.97g中间体c11,收率68%;
S4.在250mL反应瓶中,加入上述中间体c11(11.28g,41mmol)、(4-氯-2-硝基苯基)硼酸(8.05g,40mmol)、碳酸钾(11.04g,80mmol)、100mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(0.23g,0.2mmol),加热至85℃,搅拌反应6-12h,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用乙醇和/或四氢呋喃进行纯化,即可得9.29g中间体d11,收率66%;
S5.在50mL反应瓶中,加入上述中间体d11(7.04g,20mmol)、亚磷酸三乙酯(16.62g,100mmol)、氯苯(12.26g,100mmol),加热回流反应12h,冷却至室温,加入水,用二氯甲烷萃取后分液,有机相浓缩,用乙醇和/或四氢呋喃纯化,即可得3.58g中间体e11,收率56%;
S6.在100mL反应瓶中,加入上述中间体e11(3.20g,10mmol)、溴苯(1.73g,11mmol)、碳酸钾2.76g(20mmol)和50mL N,N-二甲基乙酰胺。通入氮气,加入碘化亚铜0.19g(1mmol)和邻菲啰啉0.36g(2mmol),加热回流搅拌8h,然后冷却至室温,向反应液中加入水,过滤,滤饼用乙醇和/或四氢呋喃进行纯化,得到2.89g中间体f11,收率73%;
S7.在100mL反应瓶中,加入上述中间体f11(1.98g,5mmol)、(4-(2-苯基-1氢-苯并咪唑-1-基)苯基)硼酸(1.57g,5mmol)、碳酸钾(1.38g,10mmol)、30mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(0.03g,0.03mmol),加热至85℃,搅拌反应6-12h,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用10:1的石油醚与二氯甲烷在硅胶柱中淋洗,浓缩,即可得2.21g化合物A-104,收率70%。
质谱仪MALDI-TOF-MS(m/z)=629.7583,理论分子量:629.7670,元素分析:理论值:C44H31N5(%):C83.92;H4.96;N11.12;实测值:C83.94;H4.95;N11.12。
合成实施例12:合成化合物(B-5)
S1.将合成实施例1步骤S1中的2,6-二氟吡嗪替换成2,5-二氟吡嗪(19.15g,165mmol),其他合成过程按照合成实施例1的步骤S1,即可得30.59g中间体a12,收率63%;
S2.将合成实施例1步骤S2中的中间体a1替换成中间体a12(24.28g,80mmol),其他合成过程按照合成实施例1的步骤S2,即可得23.74g中间体b12,收率65%;
S3.将合成实施例1步骤S3中的中间体b1替换成中间体b12(18.26g,40mmol),其他合成过程按照合成实施例1的步骤S3,即可得5.90g中间体c12,收率50%;
S4.将合成实施例4步骤S4中的中间体c3替换成中间体c12(2.95g,10mmol)、(10-苯基蒽-9-基)硼酸替换成(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸(3.53g,10mmo),其他合成过程按照合成实施例4的步骤S4,即可得4.20g化合物B-5,收率74%。
质谱仪MALDI-TOF-MS(m/z)=567.6123,理论分子量:567.6080,元素分析:理论值:C37H21N5(%):C78.29;H3.73;N12.34;实测值:C78.27;H3.74;N12.34。
合成实施例13:合成化合物(B-6)
S1.将合成实施例1步骤S1中的2,6-二氟吡嗪替换成2,5-二氟吡嗪(19.15g,165mmol),其他合成过程按照合成实施例1的步骤S1,即可得29.62g中间体a13,收率61%;
S2.将合成实施例1步骤S2中的中间体a1替换成中间体a13(24.28g,80mmol),其他合成过程按照合成实施例1的步骤S2,即可得24.47g中间体b13,收率67%;
S3.将合成实施例1步骤S3中的中间体b1替换成中间体b13(18.26g,40mmol),其他合成过程按照合成实施例1的步骤S3,即可得6.25g中间体c13,收率53%;
S4.将合成实施例1步骤S4中的中间体c1替换成中间体c13(5.89g,20mmol),其他合成过程按照合成实施例1的步骤S4,即可得6.40g化合物B-6,收率65%。
质谱仪MALDI-TOF-MS(m/z)=491.5046,理论分子量:491.5100,元素分析:理论值:C31H17N5(%):C75.75;H3.49;N14.25;实测值:C75.76;H3.48;N14.24。
合成实施例14:合成化合物(B-10)
S1.将合成实施例3步骤S1中的2,6-二溴吡嗪替换成2,5-二溴吡嗪(39.25g,165mmol),其他合成过程按照合成实施例1的步骤S1,即可得35.56g中间体a14,收率65%;
S2.将合成实施例3步骤S2中的中间体a3替换成中间体a14(27.19g,82mmol),其他合成过程按照合成实施例3的步骤S2,即可得21.89g中间体b14,收率70%;
S3.将合成实施例3步骤S3中的中间体b3替换成中间体b14(19.55g,50mmol),其他合成过程按照合成实施例3的步骤S3,即可得6.21g中间体c14,收率38%;
S4.将合成实施例3步骤S4中的中间体c3替换成中间体c14(3.27g,10mmol),其他合成过程按照合成实施例3的步骤S4,即可得3.70g化合物B-10,收率68%。
质谱仪MALDI-TOF-MS(m/z)=544.6958,理论分子量:544.6900,元素分析:理论值:C36H20N2(%):C79.38;H3.70;N5.14;实测值:C79.36;H3.72;N5.15。
合成实施例15:合成化合物(B-20)
S1.将合成实施例3步骤S1中的5-氯-2-(甲基亚磺酰基)苯基硼酸替换成(4-氯-2-(甲酯基)苯基)硼酸(34.31g,160mmol)、2,6-二溴吡嗪替换成2,5-二溴吡嗪(39.25g,165mmol),其他合成过程按照合成实施例1的步骤S1,即可得32.50g中间体a15,收率62%;
S2.将合成实施例3步骤S2中的中间体a3替换成中间体a15(26.20g,82mmol)、2-(甲基亚磺酰基)苯基硼酸替换成(2-(甲酯基)苯基)硼酸(14.40g,80mmol),其他合成过程按照合成实施例3的步骤S2,即可得到19.89g中间体b15,收率65%;
S3.将合成实施例4步骤S3中的中间体b4替换成中间体b15(15.31g,40mmol),其他合成过程按照合成实施例4的步骤S3,即可得到10.11g中间体c15,收率66%;
S4.将合成实施例4步骤S4中的中间体c4替换成中间体c15(7.66g,20mmol),其他合成过程按照合成实施例4的步骤S4,即可得到4.37g中间体d15,收率63%;
S5.将合成实施例4步骤S5中的中间体d4替换成中间体d15(3.47g,10mmol)、苯并噁唑-2-基硼酸替换成(4-(二苯基氨基)苯基)硼酸(2.89g,10mmol),其他合成过程按照合成实施例4的步骤S5,即可得到4.01g化合物B-20,收率72%。
质谱仪MALDI-TOF-MS(m/z)=555.7327,理论分子量:555.7250,元素分析:理论值:C40H33N3(%):C86.45;H5.99;N7.56;实测值:C86.45;H5.97;N7.58。
合成实施例16:合成化合物(B-30)
S1.将合成实施例3步骤S1中的5-氯-2-(甲基亚磺酰基)苯基硼酸替换成(5-氯-2-硝基苯基)硼酸(32.22g,160mmol)、2,6-二溴吡嗪替换为2,5-二溴吡嗪(39.25g,165mmol),其他合成过程按照合成实施例3的步骤S1,即可得32.20g中间体a16,收率64%;
S2.将合成实施例3步骤S2中的a3替换成a16(25.16g,82mmol)、2-(甲基亚磺酰基)苯基硼酸替换为(2-硝基苯基)硼酸(13.35g,80mmol),其他合成过程按照合成实施例3的步骤S2,即可得19.41g中间体b16,收率68%;
S3.将合成实施例5步骤S3中的中间体b5替换成中间体b16(14.27g,40mmol),其他合成过程按照合成实施例5的步骤S3,即可得到6.3g中间体c16,收率54%;
S4.将合成实施例5步骤S4中的中间体c5替换成中间体c16(5.85g,20mmol),其他合成过程按照合成实施例5的步骤S4,即可得到5.78g中间体d16,收率65%;
S5.将合成实施例5步骤S5中的中间体d5替换成中间体d16(4.45g,10mmol)、二对甲苯胺替换成9氢-吡咯并[2,3-b:4,5-c']二吡啶(1.69g,10mmol),其他合成过程按照合成实施例5的步骤S5,即可得到4.34g化合物B-30,收率75%。
质谱仪MALDI-TOF-MS(m/z)=577.6472,理论分子量:577.6510,元素分析:理论值:C38H23N7(%):C79.01;H4.01;N16.97;实测值:C79.00;H4.02;N16.96。
合成实施例17:合成化合物(B-43)
S1.将合成实施例1步骤S1中的2-溴-4-氯苯酚替换为2-溴苯酚(27.68g,160mmol)、2,6-二氟吡嗪替换为2-溴-6-氟吡嗪(28.32g,160mmol),其他合成过程按照合成实施例1的步骤S1,即可得39.06g中间体a17,收率74%;
S2.将合成实施例6步骤S2中的中间体a6替换为中间体a17(26.40g,80mmol),其他合成过程按照合成实施例6的步骤S2,即可得11.36g中间体b17,收率57%;
S3.将合成实施例6步骤S3中的中间体b6替换为中间体b17(10.21g,41mmol)、2-(甲基亚磺酰基)苯基硼酸替换为(5-氯-2-(甲基亚磺酰基)苯基)硼酸(8.74g,40mmol),其他合成过程按照合成实施例6的步骤S3,即可得9.86g中间体c17,收率65%;
S4.将合成实施例6步骤S4中的中间体c6替换为中间体c17(6.86g,20mmol),其他合成过程按照合成实施例6的步骤S3,即可得9.27g中间体d17,收率48%;
S5.将合成实施例7步骤S6中的中间体e7替换为中间体d17(1.55g,5mmol)、[1,1'-联苯基]-4-基硼酸替换为(3-(苯并噁唑-2-基)苯基)硼酸(1.20g,5mmol),其他合成过程按照合成实施例7的步骤S6,即可得1.71g化合物B-43,收率73%。
质谱仪MALDI-TOF-MS(m/z)=469.5096,理论分子量:469.5180,元素分析:理论值:C29H15N3(%):C74.19;H3.22;N8.95;实测值:C74.20;H3.20;N8.96。
合成实施例18:合成化合物(B-48)
S1.将合成实施例1步骤S1中的2,6-二氟吡嗪替换为2-溴-6-氟吡嗪(28.32g,160mmol),其他合成过程按照合成实施例1的步骤S1,即可得41.98g中间体a18,收率72%;
S2.将合成实施例6步骤S2中的a6替换成a18(29.15g,80mmol),其他合成过程按照合成实施例6的步骤S2,即可得12.25g中间体b18,收率54%;
S3.将合成实施例6步骤S3的b6替换成b18(11.62g,41mmol),2-(甲基亚磺酰基)苯基硼酸替换成(2-(甲酯基)苯基)硼酸(7.20g,40mmol),其他合成过程按照合成实施例6的步骤S3,即可得到8.54g中间体c18,收率63%;
S4.将合成实施例7步骤S4的c7替换成c18(6.78g,20mmol),其他合成过程按照合成实施例7的步骤S4,即可得到5.15g中间体d18,收率76%;
S5.将合成实施例7步骤S5的d7替换成d18(3.39g,10mmol),其他合成过程按照合成实施例7的步骤S5,即可得到2.28g中间体e18,收率71%;
S6.在50mL反应瓶中,加入镁(0.14g,5.75mmol)、上述中间体e18(1.6g,5mmol)、按照中间体e18的重量计,加入10-15倍体积的四氢呋喃,通入氮气,升温至65℃反应2-4h后,降温至0℃-5℃,向反应瓶中缓慢滴加2-溴-4,6-二苯基吡啶的四氢呋喃溶液(1.55g,5mmol),搅拌反应8-16h,然后恢复至室温,向反应液中加入稀盐酸猝灭反应,分液,水相用四氢呋喃萃取后,与有机相合并浓缩,与滤饼一起用10:1的石油醚与二氯甲烷在硅胶柱中淋洗,浓缩,即可得到1.60g化合物(B-48),收率60%。
质谱仪MALDI-TOF-MS(m/z)=515.6235,理论分子量:515.6160,元素分析:理论值:C36H25N3(%):C83.86;H4.89;N8.15;实测值:C83.84;H4.90;N8.14。
合成实施例19:合成化合物(B-63)
S1.将合成实施例1步骤S1中的2-溴-4-氯苯酚替换成2-溴苯酚(27.68g,160mmol),2,6-二氟吡嗪替换成2-溴-6-氟吡嗪(28.32g,160mmol),其他合成过程按照合成实施例1的步骤S1,即可得37.49g中间体a19,收率71%;
S2.将合成实施例6步骤S2中的a6替换成a19(26.40g,80mmol),其他合成过程按照合成实施例6的步骤S2,即可得11.36g中间体b19,收率57%;
S3.将合成实施例6步骤S3的b6替换成b19(10.21g,41mmol),2-(甲基亚磺酰基)苯基硼酸替换成(4-氯-2-硝基苯基)硼酸(8.05g,40mmol),其他合成过程按照合成实施例6的步骤S3,即可得到8.69g中间体c19,收率69%;
S4.将合成实施例8步骤S4的c8替换成c19(6.51g,20mmol),其他合成过程按照合成实施例8的步骤S4,即可得到3.23g中间体d19,收率55%;
S5.将合成实施例8步骤S5的d8替换成d19(2.94g,10mmol),其他合成过程按照合成实施例8的步骤S5,即可得到2.81g中间体e19,收率76%;
S6.将合成实施例7步骤S6的e7替换成e19(1.85g,5mmol)、[1,1'-联苯基]-4-基硼酸替换成[1,1':3',1”-三联苯]-5'-基硼酸(1.37g,5mmol),其他合成过程按照合成实施例7的步骤S6,即可得到1.94g化合物B-63,收率69%。
质谱仪MALDI-TOF-MS(m/z)=563.6564,理论分子量:563.6600,元素分析:理论值:C40H25N3(%):C85.24;H4.47;N7.46;实测值:C85.25;H4.47;N7.45。
合成实施例20:合成化合物(B-79)
S1.将合成实施例3步骤S1中的5-氯-2-(甲基亚磺酰基)苯基硼酸替换成(2-(甲基亚磺酰基)苯基)硼酸(29.44g,160mmol)、2,6-二溴吡嗪替换成2,5-二溴吡嗪(39.25g,165mmol),其他合成过程按照合成实施例3的步骤S1,即可得31.38g中间体a20,收率66%;
S2.将合成实施例9步骤S2中的中间体a9替换成中间体a20(29.72g,100mmol),其他合成过程按照合成实施例9的步骤S2,即可得12.46g中间体b20,收率47%;
S3.将合成实施例6步骤S3的b6替换成b20(10.87g,41mmol),2-(甲基亚磺酰基)苯基硼酸替换成(4-氯-2-(甲酯基)苯基)硼酸(8.58g,40mmol),其他合成过程按照合成实施例6的步骤S3,即可得到8.80g中间体c20,收率62%;
S4.将合成实施例7步骤S4的c7替换成c20(7.10g,20mmol),其他合成过程按照合成实施例7的步骤S4,即可得到5.18g中间体d20,收率73%;
S5.将合成实施例7步骤S5的d7替换成d20(3.55g,10mmol),其他合成过程按照合成实施例7的步骤S5,即可得到2.39g中间体e20,收率71%;
S6.将合成实施例7步骤S6的e7替换成e20(1.68g,5mmol)、[1,1'-联苯基]-4-基硼酸替换成(1-苯基-1氢-苯并咪唑-2-基)硼酸(1.19g,5mmol),其他合成过程按照合成实施例7的步骤S6,即可得到1.71g化合物B-79,收率69%。
质谱仪MALDI-TOF-MS(m/z)=494.6248,理论分子量:494.6160,元素分析:理论值:C32H22N4(%):C77.71;H4.48;N11.33;实测值:C77.69;H4.49;N11.33。
合成实施例21:合成化合物(B-92)
S1.将合成实施例3步骤S1中的5-氯-2-(甲基亚磺酰基)苯基硼酸替换成(2-(甲基亚磺酰基)苯基)硼酸(29.44g,160mmol)、2,6-二溴吡嗪替换成2,5-二溴吡嗪(39.25g,165mmol),其他合成过程按照合成实施例3的步骤S1,即可得32.34g中间体a21,收率68%;
S2.将合成实施例9步骤S2中的中间体a9替换成a21(29.72g,100mmol),其他合成过程按照合成实施例9的步骤S2,即可得12.20g中间体b21,收率46%;
S3.将合成实施例6步骤S3中的中间体b6替换成b21(10.87g,41mmol)、2-(甲基亚磺酰基)苯基硼酸替换成(4-氯-2-硝基苯基)硼酸(8.05g,40mmol),其他合成过程按照合成实施例6的步骤S3,即可得9.57g中间体c21,收率70%;
S4.将合成实施例8步骤S4中的中间体c8替换成c21(6.84g,20mmol),其他合成过程按照合成实施例8的步骤S4,即可得3.35g中间体d21,收率54%;
S5.将合成实施例8步骤S5中的中间体d8替换成d21(3.10g,10mmol),其他合成过程按照合成实施例8的步骤S5,即可得2.77g中间体e21,收率72%;
S6.将合成实施例7步骤S6中的中间体e7替换成e21(1.93g,5mmol)、[1,1'-联苯基]-4-基硼酸替换成咪唑并[1,2-a]吡啶-3-基硼酸(0.81g,5mmol),其他合成过程按照合成实施例8的步骤S6,即可得1.74g化合物B-92,收率74%。
质谱仪MALDI-TOF-MS(m/z)=467.5461,理论分子量:467.5500,元素分析:理论值:C29H17N5(%):C74.50;H3.67;N14.98;实测值:C74.51;H3.65;N14.99。
合成实施例22:合成化合物(B-95)
S1.将合成实施例11步骤S1中的(2-(甲酯基)苯基)硼酸替换成(4-氯-2-(甲酯基)苯基)硼酸(68.61g,320mmol)、2,6-二溴吡嗪替换成2,5-二溴吡嗪(78.50g,330mmol),其他合成过程按照合成实施例11的步骤S1,即可得64.99g中间体a22,收率62%;
S2.将合成实施例11步骤S2中的中间体a11替换成中间体a22(52.41g,160mmol),其他合成过程按照合成实施例11的步骤S2,即可得35.12g中间体b22,收率67%;
S3.将合成实施例11步骤S3中的中间体b11替换成中间体b22(26.21g,80mmol),其他合成过程按照合成实施例11的步骤S3,即可得17.09g中间体c22,收率69%;
S4.将合成实施例11步骤S4中的中间体c11替换成中间体c22(12.69g,41mmol)、(4-氯-2-硝基苯基)硼酸替换成(2-硝基苯基)硼酸(6.67g,40mmol),其他合成过程按照合成实施例11的步骤S4,即可得9.15g中间体d22,收率65%;
S5.将合成实施例11步骤S5中的中间体d11替换成中间体d22(7.04g,20mmol),其他合成过程按照合成实施例11的步骤S5,即可得3.71g中间体e22,收率58%;
S6.将合成实施例11步骤S6中的中间体e11替换成中间体e22(3.19g,10mmol),其他合成过程按照合成实施例11的步骤S6,得到3.01g中间体f22,收率76%;
S7.将合成实施例11步骤S7中的中间体f11替换成f22(1.98g,5mmol)、(4-(2-苯基-1氢-苯并咪唑-1-基)苯基)硼酸替换成(9-苯基-9氢-咔唑-2-基)硼酸(1.44g,5mmol),其他合成过程按照合成实施例11的步骤S7,即可得2.17g化合物B-95,收率72%。
质谱仪MALDI-TOF-MS(m/z)=602.7506,理论分子量:602.7410,元素分析:理论值:C43H30N4(%):C85.69;H5.02;N9.30;实测值:C85.67;H5.03;N9.30。
器件实施例1
将带有120nm ITO透明薄膜的玻璃基板依次用丙酮、异丙醇和去离子水各超声清洗10min,105℃下真空干燥2h,然后进行UV臭氧洗涤15min,即将ITO玻璃基板传送至真空蒸镀机。
在形成有ITO薄膜一侧的面上,真空蒸镀三氧化钼(MoO3),以形成10nm厚的空穴注入层;
下一步,在上述空穴注入层上,真空蒸镀4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](TAPC),以形成70nm厚的空穴传输层;
下一步,在上述空穴传输层上,共同真空蒸镀上述合成实施例1中所制备的化合物A-5(作为发光主体材料,90wt%)与4,4'-双(9-乙基-3-咔唑乙烯基)-1,1'-联苯(BCzVBi,作为发光客体材料,10wt%),以形成30nm厚度的发光层;
下一步,在上述发光层上,真空蒸镀3,3'-[5'-[3-(3-吡啶基)苯基][1,1':3',1”-三联苯]-3,3”-二基]二吡啶(TmPyPB),以形成40nm厚度的电子传输层;
下一步,在上述电子传输层上,真空蒸镀氟化锂(LiF),以形成1nm厚度的电子注入层;
最后,在上述电子注入层上,真空蒸镀铝(Al),以形成100nm的阴极。
器件实施例2至器件实施例22
按照与器件实施例1相同的方法制备有机电致发光器件,不同的是分别使用上述合成实施例2至合成实施例22中所合成的化合物分别替换上述合成实施例1中所制备的化合物A-5。
器件对比例23至器件对比例26
除了用下述化合物C-1、C-2、C-3、C-4分别替换合成实施例1中所制备的化合物A-5外,按照与器件实施例1相同的方法制备有机电致发光器件;
对上述器件实施例以及器件对比例所制备的有机电致发光器件进行性能测试,结果如表1所示:
从上表1的数据可看出,本发明提供的核心结构包含吡嗪,键接强吸电子型或强供电子型侧基的有机电致发光材料,由于吡嗪结构的缺电子性以及芳环对含吡嗪核心结构的共轭扩大,化合物分子可以获得较高的荧光量子效率及较强的刚性,从而使得本发明实现高效的深蓝光发射及优良的化合物热稳定性,化合物真空蒸镀成膜良好,另外,通过本发明特定的电子传输或空穴传输基团对核心结构进行修饰,化合物既能获得较好的激子分散能力,又能实现较好的能量传输,相比于对核心结构进行二取代的化合物C-1及C-2,或者本发明技术方案以外的其他化合物C-3及C-4,在器件的驱动电压、电流效率、寿命、色坐标等的综合性能上具有显著的进步。
以上所述仅为本发明的较佳实施例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (10)
1.一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化合物结构通式为式(1)或式(2)所示:
其中,
X选自O、S、N(R9)、C(R10)(R11);
Y选自O、S、N(R12)、C(R13)(R14);
Z1及Z2各自独立的选自C或N,并且至少一个为N,
R1至R8彼此相同或不同,各自独立地选自氢、氟基、硝基、氰基、C1~20的烷基、C1~20的烷氧基、C1~20的烷硫基、C1~20的硅烷基、C6~50的芳基、C3~50的杂芳基、C6~50的芳胺基、C6~50的芳氧基、C6~50的芳硫基,
R9至R11各自独立地选自C1~20的烷基、C6~50的芳基、C3~50的杂芳基、C6~50的芳胺基,R10与R11彼此独立,或通过单键连接;
R12至R14各自独立地选自C1~20的烷基、C6~50的芳基、C3~50的杂芳基、C6~50的芳胺基,R13与R14彼此独立,或通过单键连接。
3.根据权利要求2所述的一种有机电致发光材料,其特征在于:
所述Z1及Z2皆为N。
4.根据权利要求1所述的一种有机电致发光材料,其特征在于:
所述R1至R8中之一选自C1~20的烷基、C1~20的烷氧基、C1~20的烷硫基、C1~20的硅烷基、C6~50的芳基、C3~50的杂芳基、C6~50的芳胺基、C6~50的芳氧基、C6~50的芳硫基;
所述R1至R8中剩余基团皆为氢。
5.根据权利要求4所述的一种有机电致发光材料,其特征在于:
所述C1~20的烷基选自:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基中的一种;
所述C1~20的烷氧基选自:甲氧基、乙氧基中的一种;
所述C1~20的烷硫基选自:甲硫基、乙硫基中的一种;
所述C1~20的硅烷基选自:三甲基硅烷基、苯基二甲基硅烷基、联苯基二甲基硅烷基、甲基二苯基硅烷基中的一种;
所述C6~50的芳基选自:由取代基取代或未取代的苯基、由取代基取代或未取代的联苯基、由取代基取代或未取代的三联苯基、由取代基取代或未取代的萘基、由取代基取代或未取代的蒽基、由取代基取代或未取代的菲基、由取代基取代或未取代的芘基、由取代基取代或未取代的苯并菲基、由取代基取代或未取代的芴基、由取代基取代或未取代的螺二芴基中的至少一种;
所述C3~50的杂芳基选自:由取代基取代或未取代的吡啶基、由取代基取代或未取代的嘧啶基、由取代基取代或未取代的吡嗪基、由取代基取代或未取代的三嗪基、由取代基取代或未取代的吲哚基、由取代基取代或未取代的苯并呋喃基、由取代基取代或未取代的苯并噻吩基、由取代基取代或未取代的苯并噁唑基、由取代基取代或未取代的苯并噻唑基、由取代基取代或未取代的咔唑基、由取代基取代或未取代的苯基咔唑基、由取代基取代或未取代的咔唑基苯基、由取代基取代或未取代的二苯并呋喃基、由取代基取代或未取代的二苯并噻吩基中的至少一种;
所述C6~50的芳胺基选自:由取代基取代或未取代的二苯胺基、由取代基取代或未取代的N-苯基联苯胺基、由取代基取代或未取代的二联苯胺基、由取代基取代或未取代的N-苯基萘胺基、由取代基取代或未取代的二萘胺基、由取代基取代或未取代的三苯胺基中的至少一种;
其中:取代基选自:氰基、氟基、硝基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、苯基中的一种或其组合。
8.一种有机电致发光器件,主要包括阴极、阳极和两电极之间的有机层,或者主要包括出光层、阴极、阳极和两电极之间的有机层,其特征在于:所述两电极之间的有机层包含权利要求1-7任一所述的有机电致发光材料。
9.根据权利要求8所述的有机电致发光器件,其特征在于:所述两电极之间的有机层包括发光层,所述发光层包含权利要求1-7任一所述的有机电致发光材料。
10.根据权利要求8所述的有机电致发光器件,其特征在于:所述发光层由发光主体和发光客体组成,所述发光主体包含权利要求1-7任一所述的有机电致发光材料。
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