CN108822018A - 有机电致发光材料及其制备方法和有机电致发光器件 - Google Patents
有机电致发光材料及其制备方法和有机电致发光器件 Download PDFInfo
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- CN108822018A CN108822018A CN201710312976.6A CN201710312976A CN108822018A CN 108822018 A CN108822018 A CN 108822018A CN 201710312976 A CN201710312976 A CN 201710312976A CN 108822018 A CN108822018 A CN 108822018A
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- phenyl
- organic material
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 22
- 239000011368 organic material Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 239000000126 substance Substances 0.000 claims description 37
- -1 substituted-phenyl Chemical group 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-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 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000003541 multi-stage reaction Methods 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000005181 nitrobenzenes Chemical class 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 6
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 15
- 238000000034 method Methods 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000001819 mass spectrum Methods 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 13
- 239000000376 reactant Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 230000003292 diminished effect Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- 239000004411 aluminium Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
- MBAIEZXRGAOPKH-UHFFFAOYSA-N 1,2,3,6,7,8-hexahydropyrene Chemical class C1CCC2=CC=C3CCCC4=CC=C1C2=C43 MBAIEZXRGAOPKH-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- AQZMINLSVARCSL-UHFFFAOYSA-N 4-chloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical class ClC1=CC(=O)C(C#N)=C(C#N)C1=O AQZMINLSVARCSL-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229940127007 Compound 39 Drugs 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000032258 transport Effects 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- 241000790917 Dioxys <bee> Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 150000004770 chalcogenides Chemical class 0.000 description 2
- 229940125844 compound 46 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003220 pyrenes Chemical class 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 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
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- UJORPFQWUKFXIE-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4h-cyclopenta[c]pyrazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(CCC2)=C2C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 UJORPFQWUKFXIE-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- KMQHTSKEXRYKGW-UHFFFAOYSA-N 2-naphthalen-1-yl-4-n,4-n-diphenylbenzene-1,4-diamine Chemical group C1=C(C=2C3=CC=CC=C3C=CC=2)C(N)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 KMQHTSKEXRYKGW-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 241001614291 Anoplistes Species 0.000 description 1
- SMEOURDBFVPLAY-UHFFFAOYSA-N C1=CC=CC2=NC3=CC=CC=C3N=C12.C1=CC=CC=C1 Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C12.C1=CC=CC=C1 SMEOURDBFVPLAY-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical group [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 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 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- NCWQJOGVLLNWEO-UHFFFAOYSA-N methylsilicon Chemical group [Si]C NCWQJOGVLLNWEO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GTDQGKWDWVUKTI-UHFFFAOYSA-N o-aminoacetophenone Chemical compound CC(=O)C1=CC=CC=C1N GTDQGKWDWVUKTI-UHFFFAOYSA-N 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
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Abstract
本发明涉及一种有机电致发光材料及其制备方法和有机电致发光器件,涉及发光材料领域,本发明的目的是提供一种发光效率高、器件寿命好、具有适当的色坐标的新型结构的有机电致发光材料及其制备方法和有机电致发光器件,本发明提供的有机电致发光材料具有高的电子传输效率,从而能够在制造器件时防止结晶,并能够很容易地形成层,由此改善了器件的电流特性。本发明提供的有机电致发光材料的制备方法,原料易得,工艺简单,适合于工业化生产。
Description
技术领域
本发明涉及发光材料领域,具体涉及一种有机电致发光材料及其制备方法和有机电致发光器件。
背景技术
电致发光器件(electroluminescence device: EL device)作为自发光型显示器件,它具有可视角度宽、对比度好,以及应答速度快的优点。1987年,柯达(Eastman Kodak)公司首次开发了利用低分子芳香二胺和铝络合物作为发光层材料的有机电致发光器件。有机电致发光器件中决定发光效率、寿命和性能的最重要的因素是发光材料。
目前已经产业化的蓝色发光材料有DPVBi、二萘蒽(dinaphthylanthracen)、4-t-丁基二萘嵌苯(tetra(t-butyl)perlyene)等。上述材料的发光效率达到6 Lm/W、器件寿命达到30,000h,但因会发生驱动时间引起的色纯度低的问题,导致应用在面板的时候寿命只能达到几千小时。而蓝色发光材料的发射波长向长波方向移动,会使效率方面提高很多,但色坐标满足不了要求,所以不适合于高品位的面板中。此外还有效率和热稳定性方面存在一些问题,因而急需研制一种色纯度、效率、热稳定性方面均能满足要求的新材料。
发明内容
本发明的目的是:提供一种发光效率高、器件寿命好、具有适当的色坐标的新型结构的有机电致发光材料及其制备方法和有机电致发光器件。
为了实现上述目的,本发明的技术方案具体为,一种有机电致发光材料,其化学结构式如下:
式(I);
其中,Ar1和Ar2各自独立地选自苯基、碳原子数为6-18的取代苯基、碳原子数为12-17的芳族杂环基或碳原子数为10-25的稠环芳烃,虚线出表示与相邻的苯形成形成咔唑环,吖啶环;
R为氢、碳原子数为1-8的烷基、环丙基、环戊基、苯基、二甲基苯基、甲基苯基、奈基、菲基、乙基苯基、二苯并呋喃基、咔唑基、三甲基硅基、二苯并噻吩基、三联苯基或取代胺基;n为0或1;
优选的,Ar1或Ar2选自氢、,,,,,,,,,,,,,,,,,;其中,表示连接键。
优选的,R为氢、甲基、乙基、丙基、丁基、己基、异丙基、异丁基、叔丁基、新戊基、环丙基、环戊基、辛基、2-乙基己基、苯基、甲基取代的苯基、乙烯基取代的苯基、萘基、菲基、三甲基硅取代的苯基、苯并呋喃基、苯并噻吩基、咔唑基、芳香胺。
优选的,所述化合物为化学式1、化学式2、化学式3、化学式4或化学式5,
化学式1,
化学式2,
化学式3,
化学式4,
化学式5。
本发明的代表化合物是用下面化合物举例子,但不局限在这个范围内:
式1,式2,
式3,式4,
式5,式6,
式7,式8,
式9,式10,
式11,式12,
式13,式14,
式15,式16,
式17,式18,
式19,式20,
式21,式22,
式23,式24,
式25,式26,
式27,式28,
式29,式30,
式31,式32,
式33,式34,
式35,式36,
式37,式38,
式39,式40,
式41,式42,
式43,式44,
式45,式46,
式47,式48,
式49,式50,
式51,式52。
本发明还提供了一种所述芘类的化合物的制备方法,包括:
将结构的化合物、与结构的化合物及结构的化合物混合反应,得到结构的化合物;
将结构的化合物与结构的化合物反应得
到结构的化合物,经过NBS上溴得到
结构的化合物,继续与反应得到式(I)的化合物;
其中,结构的的化合物是由1,2,3,6,7,8-六氢芘的溴代物或硼酸,分别与邻位的卤代硝基苯或苯胺或氨基苯乙酮经多步反应得到的。
一种有机电致发光器件,包括第一电极、第二电极和设置于所述第一电极与第二电极之间的有机层;所述有机层包括化学式1所示的有机电致发光材料。
在上述技术方案中,所述有机层还包括由Ⅰ主族、Ⅱ主族、Ⅳ主族、Ⅴ主族转移金属、镧和d-转移元素中的一个以上的金属或其金属络合物。
上述有机层可以包括发光层和电子形成层。
另外,上述有机层是包含一个以上的上述有机电致材料以外还包含蓝色、红色或黄色发光化合物的有机发光层同时形成白色有机电致发光器件。
本发明的有机电致发光器件中至少安置一面电极中另一面内表面硫族化物(chalcogenide)、卤化金属层及金属氧化物层中选择的一层以上。
具体的说有机发光层的阳极表面硅、铝及硫族化物(chalcogenide)(包括氧化物)层,另外发光体层侧的阴极表面安置卤素金属层或金属氧化物。从这些实施得到驱动的稳定性。上述硅、铝及硫族化物理想实例是有SiOX(1≤X≤2),AlOX(1≤X≤1.5),SiON或SiAlON,卤化金属的理想实例是有LiF,MgF2,CaF2,氟化稀土类金属,金属氧化物的理想例是有Cs2O,Li2O,MgO,SrO,BaO,CaO。
另外,本发明的有机电致发光器件中,至少包括电子传输化合物、掺杂材料和空穴传输化合物中的一种或多种混合。
本发明的有机电致材料化合物是电子传输效率高,制备器件时,防止结晶化层,改善器件的电流特性,同时电流效率高。
具体实施方式
为了进一步理解本发明,对本发明的代表化合物举例说明本发明的有机电致发光材料及它的制造方法及说明制备的有机电致发光器件的发光特性。
通过以下实施例具体说明本发明的有机电致发光器件用化合物及包含它的有机电致发光器件的制造方法。但这仅仅是举例而不是用于限定本发明的范围。
实施例1
中间体1-1的合成
反应容器里加1,2,3,6,7,8-六氢芘(10g,48mmol),N-溴代丁二酰亚胺(21.4g,120mmol),二氯甲烷250mL,乙腈 250ml以后常温搅拌24小时。反应结束以后减压过滤得到固体,得到的固体用哪个甲醇洗涤得到中间体[1-1-1](12.3g,收率70%)。质谱:理论值363,测量值363.95。
反应容器里氮气条件下加中间体[1-1-1]22.00g(60.11mmol)溶解在四氢呋喃(150mL),氮气条件下,冷却-78℃滴加正丁基锂(57.7mL,144.28mmol)和硼酸三甲酯16.2ml(144.28mmol)以后常温搅拌3小时。反应终结以后加HCl水溶液以后有机层萃取,有机层用硫酸镁干燥过滤,浓缩溶剂柱层析得到中间体[1-1](12.4g,69.5%),质谱:理论值296, 测量值296.14。
中间体1-2的合成
参照中间体1-1的合成,加入1,2,3,6,7,8-六氢芘1.2倍量的N-溴代丁二酰亚胺,得到化合物1-2-1,参照化合物1-1的合成,使用相同的实验方法制备得到中间体1-2。
实施例2
中间体2-1的合成
反应容器里加中间体1-1(5.8 g,16.9mmol)、2-溴-硝基苯(3.7 g,18.4 mmol)、四(三苯基膦)钯(0.7g,1.08mmol)、碳酸钾 (5.3 g,38.3mmol)、甲苯(60mL)、乙醇(20mL)及蒸馏水(20mL),120℃条件下搅拌3小时。反应终结以后用蒸馏水洗涤,用乙酸乙酯萃取有机层。萃取的有机层用硫酸镁干燥以后减压蒸馏去掉溶剂,用柱层析得到中间体2-1-1(4.95g,65%),质谱:理论值450,测量值450.16。
化合物2-1-1(35.1g,78mmol)和亚磷酸三乙酯 (200ml)加入邻二氯苯(150ml)以后,150℃条件下搅拌一天,反应终结以后,减压浓缩以后用乙酸乙酯萃取有机层,用柱层析提纯中间体2-1(16.6g,55%),质谱:理论值386,测量值386.18。
中间体2-2的合成
参照中间体2-1的合成,将中间体1-1替换成中间体1-2,用相同的实验方法制备得到中间体2-2。
中间体2-3的合成
反应容器里加2-氯苯胺 (6.7g,52.5mmol)、中间体1-1-1(16.0g,43.8mmol)、三[二亚苄基丙酮]二钯(1.62g,1.74mmol)、三叔丁基膦(1.5g,4.38mmol)、叔丁醇钠 (12.6g,131.7mmol)、甲苯(150mL)。70 ℃条件下回流搅拌4小时。反应结束以后常温加蒸馏水稀释以后二氯甲烷和水萃取,有机层用硫酸镁干燥以后浓缩的固体用二氯甲烷和己烷重结晶得到中间体2-3-1(15.9g,79%),质谱:理论值458,测量值458.13。
反应容器里加中间体2-3-1(16g,34.8mmol)、三苯基膦(22.8g,86.7mmol)、邻二氯苯 (400mL)以后,180℃条件下回流搅拌24小时。反应结束以后常温冷却浓缩,浓缩的化合物用柱层析和重结晶方法得到中间体2-3(10.0g, 75%),质谱:理论值386, 测量值386.18。
中间体2-4的合成
反应容器(500mL)里加中间体1-1-1(7.1g,19.39mmol)、邻氨基苯乙酮(2.81ml,23.27mmol)、甲苯(150ml)以后搅拌5分,加入碳酸铯(12.64g,38.79mmol)、三[二亚苄基丙酮]二钯(1.4g,1.55mmol)、三叔丁基膦(50%)(1.51ml,1.51mmol)以后搅拌2天,薄层色谱(MC:Hex =1:1)确认反应结束以后冷却室温。过滤以后使用水(300mL),氯化钠 (200mL),二氯甲烷(150mL)萃取用硫酸镁干燥以后,减压浓缩,过滤硅胶滤斗,用二氯甲烷/己烷重结晶得到中间体2-4-1(5.1g,55%),质谱:理论值474,测量值474.23。
反应容器(500mL)里加入中间体2-4-1(4.98g, 10.55mmol),换气二次,氮气条件下,加入四氢呋喃(250ml),0℃条件慢慢滴加氯化镁 (10.55ml, 31.65mmol),滴加过程中反应溶液黄色变成红色,室温搅拌3小时。反应结束以后滴加饱和氯化铵水溶液 (300mL)。使用饱和氯化铵水溶(300mL)和二氯甲烷MC(100mL)萃取有机物,加硫酸镁除掉水分以后进行加压蒸馏。使用柱层析(MC:Hex=1:10)得到中间体2-4-2(4.8g,90%),质谱:理论值506,测量值506.29。
反应容器(500mL)里加中间体2-4-2(5g, 9.95mmol),溶剂在二氯甲烷 (90ml)里氮气条件下搅拌10分,室温里滴加甲基磺酸(3.23ml,49.72mmol)以后搅拌2小时,薄层色谱(EA:Hex=1:5),确认反应结束以后使用NaCl(150mL)、MC(100mL)、NaHCO3(150mL)萃取有机物,硫酸镁去掉水分以后加压蒸馏浓缩产品,固体用乙酸乙酯(g/7ml)洗涤得到中间体2-4(3.6g,76%),质谱:理论值470,测量值470.27。
中间体2-5的合成
参照中间体2-4的合成,将中间体1-1替换成中间体1-2,用相同的实验方法制备得到中间体2-5 。
实施例3 化合物的合成
化合物3的合成
氮气条件下,向反应容器里加中间体2-1(13.4g,34.72mmol)、溴苯(5.45g,34.72mmol)用甲苯里(230ml)浑浊,再加叔丁醇钠(10.01g,104.16mmol)、乙酸钯(0.31g,1.39mmol)、t-三叔丁基膦(1.12g,2.78mmol)以后80℃条件下搅拌1小时。反应结束以后加水200ml,生成的固体减压过滤以后用水洗涤2次,干燥得到灰色中间体3-1(16.2g,86.8%),质谱:理论值538, 测量值538.24。
反应容器里加中间体3-1(14.9g, 27.64mmol)、2,3-二氯-5,6-二氰基-1,4-苯醌(7.53g,33.2mmol)、甲苯(500mL)以后90℃条件下搅拌3小时,反应液冷却以后重结晶得到目的化合物3(12.96g,收率88%),质谱:理论值532, 测量值532.19。
化合物1和2的合成
参照化合物3的合成,将中间体2-1替换成中间体2-2 ,用相同的实验方法制备得到化合物1 ;
参照化合物1的制备方法,将溴苯替换成3-溴-1,1'-联苯基,用相同的实验方法制备得到化合物2 。
化合物4的合成
反应容器里加入中间体(3)(11.4g, 21.43mmol)、N-溴代丁二酰亚胺(8.4g,47.1mmol)、二氯甲烷(360mL)、甲醇(360ml)以后常温搅拌24小时。反应结束以后析出的固体通过减压过滤,得到的固体用甲醇洗涤得到中间体(4-1)(11.8g,收率80%),质谱:理论值688, 测量值688.01。
氮气条件下反应容器(1L)里加入中间体 (4-1) (14.8g, 21.5mmol)、[1,1’-双(二苯基膦基)二茂铁]二氯化钯(2.0g)、溶解在四氢呋喃的异丙基溴化镁(1M,300ml)、二氧六环(300mL)以后90oC条件下搅拌12小时。反应液冷却以后二氯甲烷和水分离有机层,有机层浓缩以后得到固体进行重结晶及甲醇洗涤得到化合物(4)(8.75g,收率66%),质谱:理论值616, 测量值616.29。
化合物5~37的合成
参照化合物3的合成方法,将溴苯替换成表中反应物1和反应物2的化学式,得到对应中间体,参照化合物4的合成方法,将替换成表中反应物3的化学式,制备得到化学式5~37的化合物,表中,“—”表示不需要反应物参与化学反应。
表1 制备化合物5~37的反应物、目标产物及产率
。
化合物38的合成
反应容器里加入中间体2-3(15.3g,43.5mmol)、1-溴苯(16.4g,104mmol)、乙酸钯(3.2g,3.5mmol)、三叔丁基膦(1.8g,8.7mmol)、叔丁醇钠(t-Bu)(25g,261mmol)、甲苯(300mL)以后,110℃条件下回流搅拌8小时。反应结束以后常温加蒸馏水稀释反应体系,用二氯甲烷和蒸馏水萃取有机物,有机层用硫酸镁干燥浓缩以后生成的化合物二氯甲烷和己烷进行重结晶得到中间体38-1(17.3g,74%),质谱:理论值538, 测量值538.24。
反应容器里加中间体38-1(7.43g,13.8mmol)、2,3-二氯-5,6-二氰基-1,4-苯醌(3.8g,16.6mmol),甲苯(250mL)以后90℃条件下3h搅拌。反应液冷却以后进行过滤硅胶滤斗,有机层浓缩以后重结晶得到化合物(38)(6.8g,收率93%),质谱:理论值532, 测量值532.19。
化合物39的合成
反应容器里加化合物(38)(11.4g, 21.43mmol)、N-溴代丁二酰亚胺(8.4g,47.1mmol)、二氯甲烷(360mL)、甲醇(360ml)以后常温搅拌24小时。反应结束以后析出的固体通过减压过滤,得到的固体用甲醇洗涤得到中间体(39-1)(11.8g,收率80%),质谱:理论值688, 测量值688.01。
氮气条件下反应容器(1L)里加中间体 (39-1) (14.8g, 21.5mmol)、[1,1’-双(二苯基膦基)二茂铁]二氯化钯(2.0g)、溶解在四氢呋喃的异丙基溴化镁(1M,300ml)、二氧六环(300mL)以后90oC条件下搅拌12小时。反应液冷却以后二氯甲烷和水分离有机层,有机层浓缩以后得到固体进行重结晶及甲醇洗涤得到化合物(39)(8.75g,收率66%),质谱:理论值616, 测量值616.29。
化合物40~45的合成
参照化合物38-1的合成方法,将溴苯替换成表中反应物1的化学式,得到对应中间体,参照化合物39的合成方法,将替换成表中反应物2的化学式,制备得到化学式40~45的化合物。
表2 制备化合物40~45的反应物、目标产物及产率
化合物47的合成
氮气条件下反应容器里加中间体2-4(8.2g, 17.36mmol)、溴苯(5.45g, 34.72mmol)以后用甲苯(230ml)溶解, 再加入叔丁醇钠(10.01g,104.16mmol),乙酸钯(20.31g,1.39mmol),三叔丁基膦(1.12g,2.78mmol),80℃条件下搅拌1h。反应结束以后加水(200ml),生成的固体减压过滤以后用水洗涤2次,加丙酮(300ml)以后回流搅拌1小时。常温里减压过滤以后干燥得到灰色中间体47-1(8.76g,收率81%),质谱:理论值622, 测量值622.33。
反应容器里加中间体47-1(8.6g,13.8mmol)、2,3-二氯-5,6-二氰基-1,4-苯醌(3.8g, 16.6mmol)、甲苯(230mL)以后90℃条件下搅拌3小时,反应液冷却以后进行过滤硅胶滤斗,在重结晶得到目标化合物(47)(7g,收率83%),质谱:理论值616, 测量值616.29。
化合物46的合成
参照化合物47的制备方法,将中间体2-4替换成中间体2-5,用相同的实验方法制备得到化合物46。
化合物48~52的合成
参照化合物47-1的合成方法,将溴苯替换成表中反应物1的化学式,得到对应中间体,参照化合物39的合成方法,将替换成表中反应物2的化学式,制备得到化学式48~52的化合物,表中,“—”表示不需要反应物参与化学反应。
表3 制备化合物48~52的反应物、目标产物及产率
有机发光器件的制备
实施例4 绿光有机电致发光器件
首先,ITO层(阳极)上面蒸镀60nm(N1,N1'-([1,1'-联苯]-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4-diphenylbenzene-1,4-diamine)形成空穴注入层。上述空穴注入层蒸镀N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(NPD)60nm、本发明的化合物3和掺杂Ir(ppy)3 [三(2-苯基吡啶)合铱]95:5重量比蒸镀30nm、双(2-甲基-8-羟基喹啉-N1,O8)-(1,1'-联苯-4-羟基)铝(BAlq)空穴阻挡层蒸镀10nm、蒸镀电子传输层8-羟基喹啉铝(Alq3)40nm 、蒸镀LiF 0.2nm形成电子注入层、蒸镀Al 150nm形成阴极。
实施例5~实施例29
发光层的绿光主体材料由表4记载的化合物4-27分别替代化合物3以外,采用与上述同样的方法制备有机电致发光器件,具体见表4。
[比较例1]~[比较例4]
发光层的主体物质由比较化合物1-比较化合物4分别替代化合物3以外,采用与上述实施例同样方法得到有机电致发光器件,具体见表4。
比较化合物1 比较化合物2 比较化合物3 比较化合物4
表4 实施例4~实施例29制备器件的亮度、效率及色坐标
由表4可知:本发明提供的芘类有机电致发光材料化合物中激子(exciton)移动明显减少,而发光效率增加,具有比较深的占有电子的能级最高的轨道(HOMO)而增加发光层内空穴覆盖(capping)能力、有效的配置发光层内电子均衡性和减少发光层内发生的过量的极化子数,提高了器件的发光效率和寿命。
本发明提供的化合物具有深的能级最高的轨道(HOMO)能隙比较大,因而空穴圆滑的从空穴传输层传输到发光层,激子在发光层内不束缚而防止发光泄露作用,因而增加发光层内电子均衡、减少过量极化子数的手段减少发光物质变形向上颜色纯度、寿命、效率等。
上述表明按置换基种类改变效率和寿命,哪个位置取代哪个置换基引起能隙(band gap)及电子特性、界面特性发生很大的变化。
尤其是,磷光主体情况把握空穴传输层和掺杂的相互关系,如果使用类似中心体很难比推理本发明化合物在磷光主体中显示的优秀的电子特性。
实施例30 红光有机电致发光器件(磷光主体)
首先,玻璃基板上形成的ITO层(阳极)上面蒸镀2-TNATA 60 nm 厚度形成空穴注入层,空穴注入层上蒸镀空穴传输层NPD 60nm。空穴传输层上面蒸镀主体材料化合物17和和掺杂物质(piq)2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate]/95:5重量比30nm厚度、蒸镀空穴阻挡层BAlq 10nm厚度、蒸镀电子传输层Alq3 40nm厚度、蒸镀电子注入层LiF 0.2nm厚度、蒸镀Al 150nm厚度形成阴极。
实施例31~42
由本发明的实施例制备的化合物17-28分别替代发光层的主体物质化合物 17,采用与上述实施例绿光有机电致发光器件同样的方法得到有机电致发光器件,具体详见表5。
[比较例5]~[比较例9]
发光层的主体物质是使用本发明实施例的化合物和比较化合物1 ~ 6 (比较化合物4以外)以外上述实施例26同样的方法制备有机发光器件。
比较化合物1 比较化合物2 比较化合物3
比较化合物5 比较化合物6
对实施例31-42及比较例5-比较例9方法制备的有机电致发光器件加正向偏压直流电压用Photo ReseArch的PR-650设备测定电致发光(EL)特性,亮度2500cd/m2基准微芯科(Microchip Technology)公司制造的寿命测试装备测定寿命T95,测定结果如表5所示。
表5 实施例30~实施例42制备器件的亮度、效率及色坐标
由表5可知:本发明提供的化合物使用在红光磷光情况也效率和寿命方面增加很多。在本发明化合物通过它固有特性深的能级最高的轨道(HOMO)能级水平有效的调节空穴传输层到发光层内空穴量,因而发光层内空穴和电子形成电子均衡而发光层界面防止热火及达到减少过量的极化子目的。本发明的化合物使用在主体材料的时候有机电致发光器件的寿命明显增加。
以上的说明是理解本发明举例子说明而已,属于本发明的技术领域里具有一般知识的人员可以不超过本发明的本质特性范围内可以多样的变形,从而本发明说明的实施例不能限定本发明发明范围,实施例是只是说明本发明而已。本发明的保护范围是按下面权利要求范围内解析,它和同等的范围内的一切技术是包括本发明权利范围内。
Claims (9)
1.一种有机电致发光材料,其化学结构式如下:
式(I);
其中,Ar1和Ar2各自独立地选自苯基、碳原子数为6-18的取代苯基、碳原子数为12-17的芳族杂环基或碳原子数为10-25的稠环芳烃,虚线出表示与相邻的苯形成形成咔唑环,吖啶环;
R为氢、碳原子数为1-8的烷基、环丙基、环戊基、苯基、二甲基苯基、甲基苯基、奈基、菲基、乙基苯基、二苯并呋喃基、咔唑基、三甲基硅基、二苯并噻吩基、三联苯基或取代胺基;n为0或1。
2.根据权利要求1所述的有机发光材料,其特征在于,所述Ar1或Ar2选自氢、,,,,,,,,,,,,,,,,,;其中,表示连接键。
3.根据权利要求1所述的有机发光材料,其特征在于,所述R为氢、甲基、乙基、丙基、丁基、己基、异丙基、异丁基、叔丁基、新戊基、环丙基、环戊基、辛基、2-乙基己基、苯基、甲基取代的苯基、乙烯基取代的苯基、萘基、菲基、三甲基硅取代的苯基、苯并呋喃基、苯并噻吩基、咔唑基、芳香胺。
4.根据权利要求1所述的有机发光材料,其特征在于,所述有机发光材料为化学式1、化学式2、化学式3、化学式4或化学式5所示的化合物:
化学式1 化学式2
化学式3 化学式4
化学式5,
其中,Ar1和Ar2各自独立地选自苯基、碳原子数为6-18的取代苯基、碳原子数为12-17的芳族杂环基或碳原子数为10-25的稠环芳烃,虚线出表示与相邻的苯形成形成咔唑环,吖啶环;
R为氢、碳原子数为1-8的烷基、环丙基、环戊基、苯基、二甲基苯基、甲基苯基、奈基、菲基、乙基苯基、二苯并呋喃基、咔唑基、三甲基硅基、二苯并噻吩基、三联苯基或取代胺基;n为0或1。
5.根据权利要求1所述的有机发光材料,其特征在于,所述有机发光材料包括式1~式52所示的化合物:
式1,式2,
式3,式4,
式5,式6,
式7,式8,
式9,式10,
式11,式12,
式13,式14,
式15,式16,
式17,式18,
式19,式20,
式21,式22,
式23,式24,
式25,式26,
式27,式28,
式29,式30,
式31,式32,
式33,式34,
式35,式36,
式37,式38,
式39,式40,
式41,式42,
式43,式44,
式45,式46,
式47,式48,
式49,式50,
式51,式52。
6.一种权利要求1~5任意一项所述的有机发光材料的制备方法,包括:将结构的化合物与结构的化合物反应得到结构的化合物,经过NBS上溴得到结构的化合物,继续与反应得到式(I)的化合物;
其中,Ar1和Ar2各自独立地选自苯基、碳原子数为6-18的取代苯基、碳原子数为12-17的芳族杂环基或碳原子数为10-25的稠环芳烃,虚线出表示与相邻的苯形成形成咔唑环,吖啶环;
R为氢、碳原子数为1-8的烷基、环丙基、环戊基、苯基、二甲基苯基、甲基苯基、奈基、菲基、乙基苯基、二苯并呋喃基、咔唑基、三甲基硅基、二苯并噻吩基、三联苯基或取代胺基;n为0或1。
7.根据权利要求6所述的有机发光材料的制备方法,其特征在于,包括:将结构的化合物、与结构的化合物及结构的化合物混合反应,得到结构的化合物。
8.根据权利要求7所述的有机发光材料的制备方法,其特征在于,包括:由1,2,3,6,7,8-六氢芘的溴代物或硼酸,分别与邻位的卤代硝基苯或苯胺或氨基苯乙酮经多步反应得到结构的化合物。
9.一种权利要求1~5任意一项所述的有机发光材料以及权利要求6~8所述的制备方法制备的化合物在有机电致发光器件中的应用。
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