CN108117511A - 螺芴环化合物、其用途及采用其的有机电致发光器件 - Google Patents
螺芴环化合物、其用途及采用其的有机电致发光器件 Download PDFInfo
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- CN108117511A CN108117511A CN201611087643.XA CN201611087643A CN108117511A CN 108117511 A CN108117511 A CN 108117511A CN 201611087643 A CN201611087643 A CN 201611087643A CN 108117511 A CN108117511 A CN 108117511A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 172
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 30
- 125000003003 spiro group Chemical group 0.000 title claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 44
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000010410 layer Substances 0.000 claims description 29
- -1 pyrimidine radicals Chemical class 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000707 boryl group Chemical group B* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000003780 insertion Methods 0.000 claims description 3
- 230000037431 insertion Effects 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 150000005045 1,10-phenanthrolines Chemical class 0.000 claims description 2
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- HIISVQYDQWJITQ-UHFFFAOYSA-N 1h-pyrrole;quinoline Chemical class C=1C=CNC=1.N1=CC=CC2=CC=CC=C21 HIISVQYDQWJITQ-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- ATPAWRVOKDYOLR-UHFFFAOYSA-N benzene oxadiazole Chemical compound C1=CC=CC=C1.O1N=NC=C1 ATPAWRVOKDYOLR-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 115
- 238000003786 synthesis reaction Methods 0.000 description 114
- 239000003153 chemical reaction reagent Substances 0.000 description 51
- 239000000047 product Substances 0.000 description 50
- 238000000921 elemental analysis Methods 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000004327 boric acid Substances 0.000 description 14
- 235000010338 boric acid Nutrition 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- KQCFUSPSVXUTNB-UHFFFAOYSA-N 3,6-dibromofluoren-1-one Chemical class C1=C(Br)C=C2C3=CC(Br)=CC(=O)C3=CC2=C1 KQCFUSPSVXUTNB-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000003205 fragrance Substances 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 7
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- FYEFHYMUEWRCRF-UHFFFAOYSA-N 2,7-dibromofluoren-1-one Chemical class BrC1=CC=C2C3=CC=C(Br)C(=O)C3=CC2=C1 FYEFHYMUEWRCRF-UHFFFAOYSA-N 0.000 description 6
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000005489 Bromoxynil Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000027756 respiratory electron transport chain Effects 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 150000002918 oxazolines Chemical class 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 150000005648 3-bromoquinolines Chemical class 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KCRFAWPHRYIIBZ-UHFFFAOYSA-N B(O)(O)OC1=CC=C(C=C1)S(=O)(=O)C2=CC=CC=C2 Chemical compound B(O)(O)OC1=CC=C(C=C1)S(=O)(=O)C2=CC=CC=C2 KCRFAWPHRYIIBZ-UHFFFAOYSA-N 0.000 description 3
- HEOOGFJUELACLE-UHFFFAOYSA-N C1(C=CC=C2C3=CC=CC=C3C=C12)=O.[Br] Chemical compound C1(C=CC=C2C3=CC=CC=C3C=C12)=O.[Br] HEOOGFJUELACLE-UHFFFAOYSA-N 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 150000004768 bromobenzenes Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 2
- JLFRMMLHHOZVRI-UHFFFAOYSA-N (3-phenylphenoxy)boronic acid Chemical class OB(O)OC1=CC=CC(C=2C=CC=CC=2)=C1 JLFRMMLHHOZVRI-UHFFFAOYSA-N 0.000 description 2
- PVPORFNQRIYQRR-UHFFFAOYSA-N 2,3-dibromofluoren-1-one Chemical compound C1=CC=C2C3=CC(Br)=C(Br)C(=O)C3=CC2=C1 PVPORFNQRIYQRR-UHFFFAOYSA-N 0.000 description 2
- 150000005645 2-bromoquinolines Chemical class 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- ONFSYSWBTGIEQE-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]ethenyl]aniline Chemical compound C=1C=C(C=CC=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ONFSYSWBTGIEQE-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical class OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 1
- 0 *c1cc(-c2c(C3O)ccc(Br)c2)c3cc1 Chemical compound *c1cc(-c2c(C3O)ccc(Br)c2)c3cc1 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical class C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- QPPPJVKZUNYWNG-UHFFFAOYSA-N 2,7-dichlorophenanthrene Chemical compound ClC1=CC=C2C3=CC=C(Cl)C=C3C=CC2=C1 QPPPJVKZUNYWNG-UHFFFAOYSA-N 0.000 description 1
- QPICKCJCTMRVCS-UHFFFAOYSA-N 2-bromo-1-phenylbenzimidazole Chemical class BrC1=NC2=CC=CC=C2N1C1=CC=CC=C1 QPICKCJCTMRVCS-UHFFFAOYSA-N 0.000 description 1
- ZEOMRHKTIYBETG-UHFFFAOYSA-N 2-phenyl-1,3,4-oxadiazole Chemical class O1C=NN=C1C1=CC=CC=C1 ZEOMRHKTIYBETG-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- HTDLSAGEOYDVSJ-UHFFFAOYSA-N 4-phenyloxadiazole Chemical class O1N=NC(C=2C=CC=CC=2)=C1 HTDLSAGEOYDVSJ-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical class BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
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- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 150000002220 fluorenes Chemical class 0.000 description 1
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 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 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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Abstract
一种螺芴环化合物、其用途及采用其的有机电致发光器件。该螺芴环化合物具有如下式(I)所示的结构;其中,A1~A12独立地为氢或吸电子基团,且不能同时为氢;吸电子基团独立地选自羰基、氰基、取代或未取代的C2~C30的杂芳基。本发明的螺芴环化合物,适合于在有机电致发光器件中作为电子传输材料,可以降低器件的启亮电压,提高器件的发光效率,有利于分子的成膜性提高,扩展了可用于有机发光器件。
Description
技术领域
本发明涉及有机电致发光材料领域,更具体地,涉及一种螺芴环化合物、其在有机电致发光领域的应用及采用其的有机光电材料、有机电致发光器件。
背景技术
由于具有驱动电压低、功耗小、对比度高、主动发光、质轻体薄、可柔性显示等诸多优点,有机电致发光二极管(OLEDs)逐渐发展成新一代平板显示技术中最有力的竞争者,广泛应用于电视、手机和可穿戴设备等诸多电子产品上。
正在开发用于许多不同类型的电子应用的有机半导体。例如在CN105895810A、CN105789239A、EP0676461A和WO98/27136A1中描述了其中这些有机半导体用作功能材料的有机电致发光器件的构造。然而,为了这些器件用于高质量和长寿命的显示器,仍然希望进一步改进,目前尤其需要改进发蓝色光的有机电致发光器件的寿命和效率。此外需要化合物具有高的热稳定性和高的玻璃化转变温度,而且它们能够在不分解的情况下升华。特别是对于高温应用,为了实现长寿命,材料结晶性能的改善是必要的。
上述仍旧需要改进的材料,当用于电子传输材料时,这些材料的性能通常会限制有机电致发光器件的工作电压和效率。
已经发现在9,10位进行取代的蒽类电子传输材料,非常适用于有机电致发光器件中,其中它们相对于现有技术产生明显的改进。此类材料具有很高的电子迁移率,但是容易结晶。
发明内容
有鉴于此,本发明的主要目的在于提供一种螺芴环化合物及采用其的有机光电材料和有机电致发光器件,以解决上述技术问题中的至少之一。
为了实现上述目的,作为本发明的一个方面,本发明提供了一种螺芴环化合物,该化合物具有式(I)所示的结构式:
其中,A1~A12独立地为氢或吸电子基团,且不能同时为氢。
作为优选,所述吸电子基团独立地选自羰基、氰基、取代或未取代的C2~C30的杂芳基。
作为本发明的另一个方面,本发明还提供了一种如上所述螺芴环化合物作为有机电致发光器件中的电子传输材料的应用。
作为本发明的再一个方面,本发明还提供了一种有机光电材料,其主要成分为如上所述的螺芴环化合物。
作为本发明的还一个方面,本发明还提供了一种有机电致发光器件,包括第一电极、第二电极和插入所述第一电极和第二电极之间的若干层的有机层,其中所述有机层中含有如上所述的螺芴环化合物。
基于上述技术方案可知,本发明的螺芴环化合物及采用其的器件具有如下有益效果:(1)适合于在有机电致发光器件中作为电子传输材料,可以降低器件的启亮电压,提高器件的发光效率,有利于分子的成膜性提高,扩展了可用于有机发光器件;(2)在材料中引入芴类结构有利于结晶性能的改善;(3)与现有技术的材料相比较,本发明的材料对于有机电子器件采用相同或更低的工作电压,能够增加效率;(4)这些化合物具有高的热稳定性及高的玻璃化转变温度,因此这些材料非常适合用于有机电子器件中。
附图说明
图1是本发明器件实施例中采用的有机电致发光器件的结构示意图。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚明白,以下结合具体实施例,并参照附图,对本发明作进一步的详细说明。
本发明公开了一种螺芴环化合物,该化合物具有式(I)所示的结构式:
其中,A1~A12独立地为氢或吸电子基团,且不能同时为氢。
上述结构的突出优点在于:整个分子基于螺芴环结构,利用中心C原子的SP3杂化立体构型打断分子的共轭,使HOMO和LUMO能级分布在上下两部分,达到阻止三线态能级降低的目的。另外,本发明的化合物采用不对称螺环结构,有效的降低了分子的对称性,有利于分子的成膜性提高。
作为优选,上述结构中吸电子基团可以独立地选自羰基、氰基、取代或未取代的C2~C30的杂芳基;其中,取代的C2~C30的杂芳基中,取代基团为C1~C4的烷基、F、Cl、Br;进一步优选地,该取代或未取代的C2~C30的杂芳基具有6~20个骨架碳原子,例如为吡啶基、噁唑基、噻唑基、喹啉基、嘧啶基、咪唑、苯基嘧啶、三嗪基、噁硼杂环基、砜基及其衍生物。再进一步优选地,该杂芳基为吡啶基、喹啉基、喹唑啉基、喹喔啉基、苯甲酰基、二苯磷酰基、三苯基硅基、4-(4-叔丁基苯基)-5-苯基三唑基、苯基恶二唑、10,10-二甲基二苯并硼烷基、二苯并噁硼烷基、苯基吡啶基、苯磺酰苯基、二苯并噻砜基、苯并噁唑基、苯并噻唑基、4,6-二苯基三嗪基、4,6-二苯基嘧啶基、1-苯基-苯并咪唑基、1,10-菲罗啉基或五氟苯基。
最优选地,该螺芴环化合物例如为具有如下所示的式(1)~式(48)的结构式之一的化合物:
下面将以多个合成实施例为例来详述本发明的上述新化合物的具体制备方法,但本发明的制备方法并不限于这多个合成实施例,本领域技术人员可以在其基础上在不悖离本发明原则的前提下进行任何修改、等同替换、改进等,而将该方法扩展到本发明的权利要求书要求保护的技术方案的范围之内。
本发明中所用的各种化学药品如石油醚、乙酸乙酯、正己烷、甲苯、四氢呋喃、二氯甲烷、乙酸、磷酸钾、叔丁醇钠、丁基锂等基础化工原料均可在国内化工产品市场买到,其中卤代菲(R=Br、Cl等)购自北京环灵科技有限公司,卤代芴酮(R=Br)购自武汉晟承宇科技有限公司。
合成实施例1
式(1)化合物的合成:
中间体1的合成:在三口烧瓶中,将4-溴菲溶于四氢呋喃THF中,降温至-80℃,缓慢滴加丁基锂(1eq),温度不超过-75℃,滴加完升至室温反应1h,将溶有2,7-二溴芴酮的THF溶液加入反应瓶中,将混合液回流反应3h,TCL检测反应完毕后,降至室温。用二氯甲烷萃取后,合并有机相,旋除有机溶剂,用硅胶柱层(洗脱剂∶石油醚∶乙酸乙酯=10∶1)分离得中间体1,收率为65.1%。
式(1)化合物的合成:100毫升三口瓶中加入中间体1、吡啶-3-硼酸,然后氮气保护下加入Pd2(dba)3、三环己基膦、磷酸钾、二氧六环和水,在油浴上加热升温回流反应24h,停止反应,降至室温。加水(50mL)淬灭,乙酸乙酯(50mL*4)萃取,100mL饱和NaCl溶液洗涤,收集有机相加入无水MgSO4干燥,旋除有机相后,过柱分离(石油醚∶乙酸乙酯=10∶1)得式(1)化合物,收率为75.2%。
产物MS(m/e):494.3,元素分析(C37H22N2):理论值C,89.85%;H,4.48%;N,5.66%;实测值C,89.86%;H,4.42%;N,5.63%。1H NMR(400MHz,CDCl3)δ8.74(s,2H),8.63(d,2H),8.06(t,4H),7.94-7.80(m,10H),7.71(t,2H),7.38(q,2H)。
合成实施例2
式(2)化合物的合成:合成步骤同式(1)化合物,只是将吡啶-3-硼酸改变为2-苯基吡啶-5-硼酸,其它试剂不变,得到式(2)化合物。
产物MS(m/e):648.3,元素分析(C49H32N2):理论值C,90.71%;H,4.97%;N,4.32%;实测值C,90.70%;H,4.94%;N,4.37%。
合成实施例3
中间体2的合成:合成步骤同中间体1,只是将4-溴菲改为4-溴-1,8-二氯菲,2,7-二溴芴酮改为3,6-二溴芴酮,其它试剂不变,得到中间体2。
中间体3的合成:100毫升三口瓶中加入4-氰基苯硼酸、中间体2与甲苯,然后氮气保护下,加入Pd(dba)2、叔丁醇钠、以及P(tBu)3,然后混合物在氮气保护下在油浴上加热回流反应10h,停止反应,加水(50mL)淬灭,乙酸乙酯(50mL*4)萃取,100mL饱和NaCl溶液洗涤,旋干后油泵抽干,过柱分离(石油醚∶乙酸乙酯=10∶1)得中间体3,收率为64.3%。
式(3)化合物的合成:氮气保护下,Pd2(dba)4和1,1′-双(二苯基膦)二茂铁加入干燥的DMF溶剂中,室温搅拌15min,加入中间体3并升温至80℃,将Zn(CN)2分批加入,反应液在80℃反应24h。待反应结束后,停止反应降至室温,用二氯甲烷萃取,有机层用无水硫酸镁干燥后,过滤,旋除溶剂,过柱分离(石油醚∶乙酸乙酯=10∶1)得式(3)化合物,收率为72.9%。
产物MS(m/e):592.2,元素分析(C43H20N4):理论值C,87.14%;H,3.40%;N,9.45%;实测值C,87.31%;H,3.43%;N,9.41%。1H NMR(400MHz,CDCl3)δ8.24(s,2H),8.21(s,2H),8.15(d,2H),8.09(d,2H),7.97(d,4H),7.91(d,4H),7.74(q,4H)。
合成实施例4
中间体4的合成:合成步骤同中间体2,只是将4-溴-1,8-二氯菲改为4-溴-9,10-二氯菲,其它试剂不变,得到中间体4。
中间体5的合成:氮气保护下,Pd2(dba)4和1,1′-双(二苯基膦)二茂铁加入干燥的DMF溶剂中,室温搅拌15min,加入中间体4并升温至80℃,将Zn(CN)2分批加入,反应液在80℃反应24h。待反应结束后,停止反应降至室温,用二氯甲烷萃取,有机层用无水硫酸镁干燥后,过滤,旋除溶剂,过柱分离(石油醚∶乙酸乙酯=10∶1)得中间体5,收率为63.9%。
式(4)化合物的合成:100毫升三口瓶中加入3-苯基苯硼酸、中间体5与甲苯,然后氮气保护下,加入Pd(dba)2、叔丁醇钠及P(tBu)3,然后混合物在氮气保护下在油浴上加热回流反应10h,停止反应,加水(50mL)淬灭,乙酸乙酯(50mL*4)萃取,100mL饱和NaCl溶液洗涤,旋干后油泵抽干,过柱分离(石油醚∶乙酸乙酯=10∶1)得式(4)化合物,收率为61.3%。
产物MS(m/e):694.1,元素分析(C53H30N2):理论值C,91.62%;H,4.35%;N,4.03%;实测值C,91.60%;H,4.32%;N,4.01%。1H NMR(400MHz,CDCl3)δ8.25(s,2H),8.15(d,2H),8.00(q,2H),7.88-7.82(m,6H),7.77-7.70(m,8H),7.60(d,4H),7.33(t,4H),7.04(t,4H)。
合成实施例5
式(5)化合物的合成:合成步骤同式(4)化合物,只是将4-溴-9,10-二氯菲改为4-溴-9-氯菲,3-苯基苯硼酸改为2-苯基吡啶-5-硼酸,其它试剂不变,得到式(5)化合物。
产物MS(m/e):543.1,元素分析(C40H21N3):理论值C,88.38%;H,3.89%;N,7.73%;实测值C,88.32%;H,3.81%;N,7.71%。
合成实施例6
式(6)化合物的合成:合成步骤同式(5)化合物,只是将2-苯基吡啶-5-硼酸改为3-苯基吡啶-6-硼酸,其它试剂不变,得到式(6)化合物。
产物MS(m/e):543.1,元素分析(C40H21N3):理论值C,88.38%;H,3.89%;N,7.73%;实测值C,88.34%;H,3.80%;N,7.71%。
合成实施例7
中间体7的合成:合成步骤同化合物式(1),只是将4-溴菲改为4-溴-9-氯菲,其它试剂不变,得到中间体7。
式(7)化合物的合成:合成步骤同式(4)化合物,只是将3-苯基苯硼酸改为4-(吡啶-3-)苯硼酸,其它试剂不变,得到式(7)化合物。
产物MS(m/e):647.1,元素分析(C48H29N3):理论值C,89.00%;H,4.51%;N,6.49%;实测值C,89.01%;H,4.52%;N,6.51%。1H NMR(400MHz,CDCl3)δ8.73(s,3H),8.63(d,3H),8.22(s,1H),8.09(d,3H),7.97(d,3H),7.91(d,2H),7.86-7.69(m,11H),7.39(q,3H)。
合成实施例8
式(8)化合物的合成:合成步骤同式(7)化合物,只是将4-溴-9-氯菲改为4-溴-2-氯菲,2,7-二溴芴酮改为3,6-二溴芴酮,吡啶3-硼酸改为吡啶-4-硼酸,4-(吡啶-3-)苯硼酸改为4-(吡啶-4-)苯硼酸,其它试剂不变,得到式(8)化合物。
产物MS(m/e):647.1,元素分析(C48H29N3):理论值C,89.00%;H,4.51%;N,6.49%;实测值C,89.03%;H,4.51%;N,6.52%。
合成实施例9
中间体8的合成:合成步骤同中间体1,只是将4-溴2,7-二氯菲改为4-溴菲,2,7-二溴芴酮改为3,6-二溴芴酮,其它试剂不变,得到中间体8。
中间体9的合成:100毫升三口瓶中加入中间体8、双联硼酸酯、Pd(dppf)Cl2、二氧六环和乙酸钾,然后氮气保护下,在油浴上加热升温90℃反应6h,停止反应,降至室温,加水(50mL)淬灭,乙酸乙酯(50mL*4)萃取,100mL饱和NaCl溶液洗涤,收集有机相加入无水MgSO4干燥,旋除有机相后,过柱分离(石油醚∶乙酸乙酯=10∶1)得中间体9,收率为65.2%。
式(9)化合物的合成:将中间体9、3-溴喹啉、四三苯基膦钯(Pd(PPh3)4)、叔丁醇钠加入到甲苯中,氮气保护下升温至80℃反应3h,加水淬灭后,用二氯甲烷萃取分液得有机相,旋除有机溶剂,用硅胶柱层(洗脱剂∶石油醚∶乙酸乙酯=10∶1)分离得式(9)化合物,收率为74.6%。
产物MS(m/e):594.1,元素分析(C45H26N2):理论值C,90.88%;H,4.41%;N,4.71%;实测值C,90.81%;H,4.43%;N,4.69%。1H NMR(400MHz,CDCl3)δ9.17(d,2H),8.48(d,2H),8.33(s,2H),8.22(d,2H),8.07(s,2H),7.96-7.89(m,6H),7.80-7.69(m,8H),7.56(t,2H)。
合成实施例10
式(10)化合物的合成:合成步骤同式(9)化合物,只是将3,6-二溴芴酮改为2,7-二溴芴酮,其它试剂不变,得到式(10)化合物。
产物MS(m/e):594.1,元素分析(C45H26N2):理论值C,90.88%;H,4.41%;N,4.71%;实测值C,90.83%;H,4.41%;N,4.73%。
合成实施例11
式(11)化合物的合成:合成步骤同式(9)化合物,只是将3-溴喹啉改为2-溴喹喔啉,其它试剂不变,得到式(11)化合物。
产物MS(m/e):596.1,元素分析(C43H24N4):理论值C,86.56%;H,4.05%;N,9.39%;实测值C,86.43%;H,4.02%;N,9.41%。
合成实施例12
式(12)化合物的合成:合成步骤同式(9)化合物,只是将4-溴菲改为4-溴-1-氯菲,3,6-二溴芴酮改为4-溴芴酮,2-溴喹啉改为2-溴喹唑啉,其它试剂不变,得到式(12)化合物。
产物MS(m/e):596.1,元素分析(C43H24N4):理论值C,86.56%;H,4.05%;N,9.39%;实测值C,86.52%;H,4.01%;N,9.43%。
合成实施例13
式(13)化合物的合成:合成步骤同式(9)化合物,只是将2-溴喹啉改为苯酰氯,其它试剂不变,得到式(13)化合物。
产物MS(m/e):548.1,元素分析(C41H24O2):理论值C,89.76%;H,4.41%;O,5.83%;实测值C,89.56%;H,4.42%。
合成实施例14
式(14)化合物的合成:合成步骤同式(13)化合物,只是将4-溴菲改为4-溴-9-氯菲,3,6-二溴芴酮改为3-溴芴酮,其它试剂不变,得到式(14)化合物。
产物MS(m/e):548.1,元素分析(C41H24O2):理论值C,89.76%;H,4.41%;O,5.83%;实测值C,89.66%;H,4.40%。
合成实施例15
式(15)化合物的合成:合成步骤同式(14)化合物,只是将4-溴9-氯菲改为4-溴-1-氯菲,苯酰氯改为二苯基次磷酸酰氯,其它试剂不变,得到式(15)化合物。
产物MS(m/e):740.1,元素分析(C51H34O2P2):理论值C,82.69%;H,4.63%;O,4.32%;P,8.36%;实测值C,82.71%;H,4.61%。
合成实施例16
式(16)化合物的合成:合成步骤同式(15)化合物,只是将4-溴1-氯菲改为4-溴-2-氯菲,3-溴芴酮改为2-溴芴酮,其它试剂不变,得到式(16)化合物。
产物MS(m/e):736.1,元素分析(C51H30O2P2):理论值C,83.14%;H,4.10%;O,4.34%;P,8.41%;实测值C,83.21%;H,4.06%。
合成实施例17
式(17)化合物的合成:合成步骤同式(2)化合物,只是将2,7-二溴芴酮改为3-溴芴酮,二(3-甲基苯基)胺改为5-苯基-5,11-二氢吲哚并咔唑,其它试剂不变,得到式(17)化合物。
产物MS(m/e):864.3,元素分析(C59H36N2S2Si):理论值C,81.91%;H,4.19%;N,3.24%;S,7.41%;Si,3.25%;实测值C,81.92%;H,4.21%;N,3.23%。
合成实施例18
式(18)化合物的合成:合成步骤同式(14)化合物,只是将4-溴-9-氯菲改为4-溴菲,其它试剂不变,得到式(18)化合物。
产物MS(m/e):731.1,元素分析(C52H33NSSi):理论值C,85.32%;H,4.54%;N,1.91%;S,4.38%;Si,3.84%;实测值C,85.35%;H,4.56%;N,1.92%。
合成实施例19
式(19)化合物的合成:合成步骤同式(3)化合物,只是将3,6-二溴芴酮改为3-溴芴酮,4-氰基苯硼酸改为[5-(4-叔丁基苯基)-4-苯基-4H-1,2,4-三唑-3-]硼酸,其它试剂不变,得到式(19)化合物。
产物MS(m/e):665.3,元素分析(C47H31N5):理论值C,84.79%;H,4.69%;N,10.52%;实测值C,84.81%;H,4.62%;N,10.53%。
合成实施例20
式(20)化合物的合成:合成步骤同式(19)化合物,只是将[5-(4-叔丁基苯基)-4-苯基-4H-1,2,4-三唑-3-]硼酸改为(5-苯基-1,3,4-噁二唑-2-)硼酸,其它试剂不变,得到式(20)化合物。
产物MS(m/e):534.1,元素分析(C37H18N4O):理论值C,83.15%;H,3.41%;N,10.43%;O,2.98%;实测值C,83.15%;H,3.41%;N,10.43%。
合成实施例21
中间体11的合成:合成步骤同中间体(9),只是将4-溴菲改为4-溴-9-氯菲,3,6-二溴芴酮改为芴酮,其它试剂不变,得到中间体11。
式(21)化合物的合成:氮气保护下,将锌粉和THF混合,加入2滴1,2-二溴乙烷,引发后,开始滴加溶有2,2′-(丙烷-2,2-二基)双(溴苯)的THF的溶液,油浴加热维持回流状态,滴加完后回流反应2小时,用冰浴降温至0度。将上面得到的中间体11溶于100mlTHF,滴加到此溶液中,反应3小时后,抽滤,滤饼用THF淋洗,滤液旋干,柱层析(洗脱液∶二氯甲烷∶石油醚=6∶1),得到式(21)化合物,收率为72.6%。
产物MS(m/e):544.1,元素分析(C42H29B):理论值C,92.65%;H,5.37%;B,1.99%;实测值C,92.61%;H,5.33%。1H NMR(400MHz,CDCl3)δ8.14(d,2H),7.96-7.91(m,5H),7.75-7.69(m,4H),7.64-7.56(m,4H),7.46-7.29(m,8H),1.71(s,6H)。
合成实施例22
中间体13的合成:合成步骤同中间体5,只是将4-溴-9,10-二氯菲改为4-溴-9-氯菲,其它试剂不变,得到中间体13。
式(22)化合物的合成:合成步骤同式(21)化合物,只是将中间体10改为中间体13,其它试剂不变,得到式(22)化合物,收率为62.6%。
产物MS(m/e):594.1,元素分析(C44H27BN2):理论值C,88.89%;H,4.58%;B,1.82%;N,4.71%;实测值C,88.91%;H,4.52%;N,4.72%。1H NMR(400MHz,CDCl3)1H NMR(400MHz,CDCl3)δ8.25(s,2H),8.20(d,1H),8.16(s,1H),8.00(d,1H),7.95(t,2H),7.81(d,2H),7.75-7.71(m,6H),7.46(d,2H),7.38(t,2H),7.32(t,2H),1.71(s,6H)。
合成实施例23
式(23)化合物的合成:合成步骤同式(21)化合物,只是将4-溴-9-氯菲改为4-溴菲,芴酮改为2-溴芴酮,2,2′-(丙烷-2,2-二基)双(溴苯)改为二(2,4,6-三甲基苯基)硼烷,其它试剂不变,得到式(23)化合物。
产物MS(m/e):588.1,元素分析(C45H37B):理论值C,91.83%;H,6.34%;B,1.84%;实测值C,91.82%;H,6.35%。
合成实施例24
中间体16的合成:合成步骤同中间体9,只是将4-溴-9-氯菲改为4-溴-2-氯菲,3,6-二溴芴酮改为3-溴芴酮,其它试剂不变,得到中间体16。
中间体17的合成:合成步骤同式(21)化合物,只是将中间体10改为中间体16,2,2′-(丙烷-2,2-二基)双(溴苯)改为二(2-溴苯)醚其它试剂不变,得到中间体17。
式(24)化合物的合成:合成步骤同式(7)化合物,只是将中间体7改为中间体17,其它试剂不变,得到式(24)化合物,收率为70.2%。
产物MS(m/e):671.1,元素分析(C50H30BNO):理论值C,89.42%;H,4.50%;B,1.61%;N,2.09%;O,2.38%;实测值C,89.41%;H,4.55%;N,2.12%。1H NMR(400MHz,CDCl3)δ8.73(s,1H),8.64(d,1H),8.42(s,1H),8.25(s,1H),8.10(q,2H),8.01(d,1H),7.96-7.90(m,5H),7.86(s,1H),7.82(d,2H),7.75-7.66(m,1H),7.59(t,1H),7.44(t,1H),7.38(q,1H),7.29(t,2H),7.06(t,1H),6.96(t,1H),6.91(q,2H)。
合成实施例25
式(25)化合物的合成:合成步骤同式(1)化合物,只是将3,6-二溴芴酮改为2-溴芴酮,吡啶-3-硼酸改为4-(苯磺酰)苯硼酸,其它试剂不变,得到式(25)化合物。
产物MS(m/e):556.1,元素分析(C39H24O2S):理论值C,84.15%;H,4.35%;O,5.75%;S,5.76%;实测值C,84.17%;H,4.32%。
合成实施例26
中间体19的合成:合成步骤同中间体7,只是将4-溴-9-氯菲改为4-溴-9,10-二氯菲,2,7-二溴芴酮改为3-溴芴酮,吡啶-3-硼酸改为4-(苯磺酰)苯硼酸,其它试剂不变,得到中间体19。
式(26)化合物的合成:氮气保护下,Pd2(dba)4和1,1′-双(二苯基膦)二茂铁加入干燥的DMF溶剂中,室温搅拌15min,加入中间体19并升温至80℃,将Zn(CN)2分批加入,反应液在80℃反应24h。待反应结束后,停止反应降至室温,用二氯甲烷萃取,有机层用无水硫酸镁干燥后,过滤,旋除溶剂,过柱分离(石油醚∶乙酸乙酯=10∶1)得式(26)化合物,收率为62.9%。
产物MS(m/e):606.1,元素分析(C41H22N2O2S):理论值C,81.17%;H,3.66%;N,4.62%;O,5.27%;S,5.29%;实测值C,81.15%;H,3.62%;N,4.60%。1H NMR(400MHz,CDCl3)δ8.29(d,2H),8.24(d,1H),8.14(d,2H),7.94(d,3H),7.80-7.69(m,8H),7.60-7.55(m,4H),7.45-7.37(m,2H)。
合成实施例27
式(27)化合物的合成:合成步骤同式(25)化合物,只是3-溴芴酮改为2-溴芴酮,4-(苯磺酰)苯硼酸改为2-硼酸苯并噻吩-5,5-二氧基,其它试剂不变,得到式(27)化合物。
产物MS(m/e):554.2,元素分析(C39H22O2S):理论值C,84.45%;H,4.00%;O,5.77%;S,5.78%;实测值C,84.41%;H,4.02%。
合成实施例28
中间体21的合成:合成步骤同中间体19,只是将4-(苯磺酰)苯硼酸改为2-硼酸苯并噻吩-5,5-二氧基,其它试剂不变,得到中间体21。
式(28)化合物的合成:100毫升三口瓶中加入AgF,Me3SiCF3和DMF,室温搅拌20分钟后,加入铜粉,搅拌反应4h生成CuCF3,将溶有中间体21的DMF溶液加入反应瓶,并升温至90℃反应5h。停止反应,降至室温后过滤,将滤液用乙醚萃取,合并有机相后用MgSO4干燥,旋除溶剂,过柱分离(石油醚∶乙酸乙酯=10∶1)得式(28)化合物,收率为68.6%。
产物MS(m/e):690.1,元素分析(C41H20F6O2S):理论值C,71.30%;H,2.92%;F,16.50%;O,4.63%;S,4.64%;实测值C,71.31%;H,2.95%。1H NMR(400MHz,CDCl3)δ8.42(s,1H),8.27(t,2H),8.15(d,1H),8.07(t,2H),7.96-7.90(m,5H),7.82-7.73(m,4H),7.60(q,3H),7.44(t,1H),7.25(t,1H)。
合成实施例29
式(29)化合物的合成:合成步骤同式(9)化合物,只是将3-溴喹啉改为2-溴苯并噁唑,其它试剂不变,得到式(29)化合物。
产物MS(m/e):574.4,元素分析(C41H22N2O2):理论值C,85.70%;H,3.86%;N,4.88%;O,5.57%;实测值C,85.64%;H,3.82%;N,4.87%。
合成实施例30
式(30)化合物的合成:合成步骤同式(9)化合物,只是将4-溴菲改为4-溴-2-氯菲,3,6-二溴芴酮改为2-溴芴酮,其它试剂不变,得到式(30)化合物。
产物MS(m/e):574.1,元素分析(C41H22N2O2):理论值C,85.70%;H,3.86%;N,4.88%;O,5.57%;实测值C,85.71%;H,3.82%;N,4.84%。
合成实施例31
式(31)化合物的合成:合成步骤同式(30)化合物,只是将4-溴-2-氯菲改为4-溴-1,8-二氯菲,其它试剂不变,得到式(31)化合物。
产物MS(m/e):574.1,元素分析(C41H22N2O2):理论值C,85.70%;H,3.86%;N,4.88%;O,5.57%;实测值C,85.71%;H,3.82%;N,4.85%。
合成实施例32
式(32)化合物的合成:合成步骤同式(29)化合物,只是将3,6-二溴芴酮改为2,7-二溴芴酮,其它试剂不变,得到式(32)化合物。
产物MS(m/e):574.1,元素分析(C41H22N2O2):理论值C,85.70%;H,3.86%;N,4.88%;O,5.57%;实测值C,85.71%;H,3.84%;N,4.85%。
合成实施例33
式(33)化合物的合成:合成步骤同式(29)化合物,只是将2-溴苯并噁唑改为2-溴苯并噻唑,其它试剂不变,得到式(33)化合物。
产物MS(m/e):606.1,元素分析(C41H22N2S2):理论值C,81.16%;H,3.65%;N,4.62%;S,10.57%;实测值C,81.13%;H,3.62%;N,4.61%。
合成实施例34
式(34)化合物的合成:合成步骤同式(30)化合物,只是将2-溴苯并噁唑改为2-溴苯并噻唑,其它试剂不变,得到式(34)化合物。
产物MS(m/e):606.1,元素分析(C41H22N2S2):理论值C,81.16%;H,3.65%;N,4.62%;S,10.57%;实测值C,81.12%;H,3.61%;N,4.66%。
合成实施例35
式(35)化合物的合成:合成步骤同式(29)化合物,只是将2-溴苯并噁唑改为2-溴苯并噻唑,其它试剂不变,得到式(35)化合物。
产物MS(m/e):606.1,元素分析(C41H22N2S2):理论值C,81.16%;H,3.65%;N,4.62%;S,10.57%;实测值C,81.21%;H,3.63%;N,4.62%。
合成实施例36
式(36)化合物的合成:合成步骤同式(32)化合物,只是将2-溴苯并噁唑改为2-溴苯并噻唑,其它试剂不变,得到式(36)化合物。
产物MS(m/e):606.2,元素分析(C41H22N2S2):理论值C,81.16%;H,3.65%;N,4.62%;S,10.57%;实测值C,81.11%;H,3.61%;N,4.59%。
合成实施例37
式(37)化合物的合成:合成步骤同式(36)化合物,只是将3,6-二溴芴酮改为3-溴芴酮,2-溴苯并噁唑改为2-溴-4,6-二苯基-1,3,5-三唑,其它试剂不变,得到式(37)化合物。
产物MS(m/e):571.1,元素分析(C42H25N3):理论值C,88.24%;H,4.41%;N,7.35%;实测值C,88.21%;H,4.42%;N,7.37%。
合成实施例38
式(38)化合物的合成:合成步骤同式(37)化合物,只是将2-溴-4,6-二苯基-1,3,5-三唑改为2-(4-溴苯基)-4,6-二苯基-1,3,5-三唑,其它试剂不变,得到式(38)化合物。
产物MS(m/e):647.1,元素分析(C48H29N3):理论值C,89.00%;H,4.51%;N,6.49%;实测值C,89.02%;H,4.51%;N,6.51%。
合成实施例39
式(39)化合物的合成:合成步骤同式(37)化合物,只是将2-溴-4,6-二苯基-1,3,5-三唑改为2-溴-1-苯基-1H-苯并咪唑,其它试剂不变,得到式(39)化合物。
产物MS(m/e):532.2,元素分析(C40H24N2):理论值C,90.20%;H,4.54%;N,5.26%;实测值C,90.21%;H,4.52%;N,5.31%。
合成实施例40
式(40)化合物的合成:合成步骤同式(37)化合物,只是将2-溴-4,6-二苯基-1,3,5-三唑改为2-溴-4,6-二苯基嘧啶,其它试剂不变,得到式(40)化合物。
产物MS(m/e):579.1,元素分析(C43H26N2):理论值C,90.50%;H,4.59%;N,4.91%;实测值C,90.52%;H,4.61%;N,4.90%。
合成实施例41
式(41)化合物的合成:合成步骤同式(37)化合物,只是将4-溴-9-氯菲改为4-溴-1,10-菲啰啉,其它试剂不变,得到式(41)化合物。
产物MS(m/e):518.1,元素分析(C39H22N2):理论值C,90.32%;H,4.28%;N,5.40%;实测值C,90.34%;H,4.22%;N,5.41%。
合成实施例42
式(42)化合物的合成:合成步骤同式(41)化合物,只是将3-溴芴酮改为3,6-二溴芴酮,其它试剂不变,得到式(42)化合物。
产物MS(m/e):696.1,元素分析(C51H28N4):理论值C,87.91%;H,4.05%;N,8.04%;实测值C,87.95%;H,4.03%;N,8.02%。
合成实施例43
式(43)化合物的合成:合成步骤同式(41)化合物,只是将4-溴菲改为4-溴-9-氯菲,3-溴芴酮改为芴酮,其它试剂不变,得到式(43)化合物。
产物MS(m/e):518.1,元素分析(C39H22N2):理论值C,90.32%;H,4.28%;N,5.40%;实测值C,90.31%;H,4.29%;N,5.41%。
合成实施例44
式(44)化合物的合成:合成步骤同式(1)化合物,只是将2,7-二溴芴酮改为3,6-二溴芴酮,吡啶-3-硼酸改为五氟苯硼酸,其它试剂不变,得到式(44)化合物。
产物MS(m/e):696.1,元素分析(C51H28N4):理论值C,87.91%;H,4.05%;N,8.04%;实测值C,87.92%;H,4.04%;N,8.02%。
合成实施例45
式(45)化合物的合成:合成步骤同式(1)化合物,只是将2,7-二溴芴酮改为3,6-二溴芴酮,吡啶-3-硼酸改为五氟苯硼酸,其它试剂不变,得到式(45)化合物。
产物MS(m/e):672.1,元素分析(C39H14F10):理论值C,69.65%;H,2.10%;F,28.25%;实测值C,69.62%;H,2.11%。
合成实施例46
式(46)化合物的合成:合成步骤同式(45)化合物,只是将3,6-二溴芴酮改为2,7-二溴芴酮,其它试剂不变,得到式(46)化合物。
产物MS(m/e):672.2,元素分析(C39H14F10):理论值C,69.65%;H,2.10%;F,28.25%;实测值C,69.64%;H,2.12%。
合成实施例47
式(47)化合物的合成:合成步骤同式(45)化合物,只是将3,6-二溴芴酮改为3-氯芴酮,4-溴菲改为4-溴-1-氯菲,其它试剂不变,得到式(47)化合物。
产物MS(m/e):672.1,元素分析(C39H14F10):理论值C,69.65%;H,2.10%;F,28.25%;实测值C,69.62%;H,2.14%。
合成实施例48
式(48)化合物的合成:合成步骤同式(46)化合物,只是将3,6-二溴芴酮改为芴酮,4-溴菲改为4-溴-1,8-二氯菲,其它试剂不变,得到式(48)化合物。
产物MS(m/e):672.1,元素分析(C39H14F10):理论值C,69.65%;H,2.10%;F,28.25%;实测值C,69.63%;H,2.13%。
本发明还公开了如上所述的螺芴环化合物作为有机电致发光器件中电子传输材料的应用,通过引入吸电子基,该化合物在有机电致发光器件中,可用于电子传输材料,例如适合于在电发光显示器中作电子传输材料。
本发明还公开了一种有机光电材料,其主要成分为如上所述的螺芴环化合物。
本发明还公开了一种有机电致发光器件,包括第一电极、第二电极和插入第一电极和第二电极之间的若干层的有机层,在该有机层中含有如上所述的螺芴环化合物。
该若干层的有机层通常例如包括空穴注入层(HIL)、空穴传输层(HTL)、发光层(EML)和电子传输层(ETL),各层厚度可以采用常规设置,其中优选发光层(EML)的主体材料或电子传输层(ETL)中的电子传输材料采用本发明的如上所述的螺芴环化合物。
下面通过将该螺芴环化合物具体应用到有机电致发光器件中测试实际使用性能来展示和验证本发明的技术效果和优点。
为了方便比较这些电子传输材料的传输性能,如图1所示,本发明设计了一简单电发光器件,使用高效电子传输材料Bphen作为比较材料。
本实施例中的化合物作为有机电致发光器件中的电子传输材料,共制备了多个有机电致发光器件,其结构均为:ITO/HIL(10nm)/HTL(80nm)/EML(30nm)/ETL(30nm)/LiF(1nm)/Al。
其中,空穴注入材料采用星型爆炸物2-TNATA;空穴传输材料使用三芳胺类材料NPB;发光层材料使用蓝荧光染料DSA-Ph染料,搭配蓝光主体ADN;电子传输层选用电子迁移率较高的BPhen。各功能层材料分子结构如下:
上述有机电致发光器件各层中未注明来源的材料均是通过市售或本领域公知的制备方法自行制备得到的。
下面通过有机电致发光器件的具体实施例来进一步说明本发明各化合物在有机电致发光器件中的具体应用及有益效果。
器件对比实施例1
本实施例中有机电致发光器件的制备过程如下:
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1×10-5~9×10-3Pa,在上述阳极层膜上真空蒸镀2-TNATA作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀膜厚为10nm;
在空穴注入层之上真空蒸镀NPB作为器件的空穴传输层,蒸镀速率为0.1nm/s,蒸镀总膜厚为80nm;
在空穴传输层之上真空蒸镀器件的发光层,发光层包括主体材料和染料材料,利用多源共蒸的方法,调节主体材料ADN的蒸镀速率为0.1nm/s,染料DSA-Ph的蒸镀速率以其3%比例进行设定,蒸镀总膜厚为30nm;
在发光层之上真空蒸镀器件的电子传输层材料Bphen,其蒸镀速率为0.1nm/s,蒸镀总膜厚为30nm;
在电子传输层上真空蒸镀厚度为0.5nm的LiF作为电子注入层,厚度为150nm的Al层作为器件的阴极。
器件实施例1~11
器件实施例1~11采用和器件对比实施例1相同的制作方法,区别仅在于,将电子传输材料Bphen置换为等当量的式(1)、式(6)、式(7)、式(12)、式(14)、式(24)、式(29)、式(36)、式(37)、式(39)或式(45)所示的化合物。
在相同亮度1000cd/m2下,测定有机电致发光器件的器件对比实施例1和器件实施例1~11中制备得到的有机电致发光器件的驱动电压和电流效率,有机电致发光器件性能见下表:
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,可以有效的降低器件工作电压,提高电流效率,是性能良好的电子传输材料。制备的器件性能有了一定提高,尤其式(7)化合物,采用其作为电子传输层制备的器件在要求亮度下(1000cd/m2),电流效率可达到11.8cd/A,电压可到5.3V,相比商业材料Bphen性能有了提高,有望推广商业化应用。
以上所述的具体实施例,对本发明的目的、技术方案和有益效果进行了进一步详细说明,应理解的是,以上所述仅为本发明的具体实施例而已,并不用于限制本发明,凡在本发明的精神和原则之内,所做的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (10)
1.一种螺芴环化合物,其特征在于,该化合物具有式(I)所示的结构式:
其中,A1~A12独立地为氢或吸电子基团,且不能同时为氢。
2.如权利要求1所述的螺芴环化合物,其特征在于,所述吸电子基团独立地选自羰基、氰基、取代或未取代的C2~C30的杂芳基。
3.如权利要求2所述的螺芴环化合物,其特征在于,所述取代或未取代的C2~C30的杂芳基中,骨架上碳原子的个数为6~20;
作为优选,所述取代的C2~C30的杂芳基中,取代基团为C1~C4的烷基、F、Cl、Br。
4.如权利要求3所述的螺芴环化合物,其特征在于,所述杂芳基为吡啶基、噁唑基、噻唑基、喹啉基、嘧啶基、咪唑、苯基嘧啶、三嗪基、噁硼杂环基、砜基及其衍生物。
5.如权利要求4所述的螺芴环化合物,其特征在于,所述杂芳基为吡啶基、喹啉基、喹唑啉基、喹喔啉基、苯甲酰基、二苯磷酰基、三苯基硅基、4-(4-叔丁基苯基)-5-苯基三唑基、苯基噁二唑、10,10-二甲基二苯并硼烷基、二苯并噁硼烷基、苯基吡啶基、苯磺酰苯基、二苯并噻砜基、苯并噁唑基、苯并噻唑基、4,6-二苯基三嗪基、4,6-二苯基嘧啶基、1-苯基-苯并咪唑基、1,10-菲罗啉基或五氟苯基。
6.如权利要求1所述的螺芴环化合物,其特征在于,所述螺芴环化合物为具有如下所示的式(1)~式(48)的结构式的化合物之一:
7.如权利要求1至6任意一项所述的螺芴环化合物作为有机电致发光器件中的电子传输材料的应用。
8.一种有机光电材料,其特征在于,其主要成分为如权利要求1至6任意一项所述的螺芴环化合物。
9.一种有机电致发光器件,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若干层的有机层,其特征在于,所述有机层中含有如权利要求1至6任意一项所述的螺芴环化合物。
10.如权利要求9所述的有机电致发光器件,所述有机电致发光器件为发蓝色光的有机电致发光二极管。
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