CN116496212A - 一种有机化合物及其制备方法和有机电致发光器件 - Google Patents
一种有机化合物及其制备方法和有机电致发光器件 Download PDFInfo
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- CN116496212A CN116496212A CN202210052222.2A CN202210052222A CN116496212A CN 116496212 A CN116496212 A CN 116496212A CN 202210052222 A CN202210052222 A CN 202210052222A CN 116496212 A CN116496212 A CN 116496212A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 138
- 238000003756 stirring Methods 0.000 claims description 90
- 239000012074 organic phase Substances 0.000 claims description 78
- 238000006243 chemical reaction Methods 0.000 claims description 68
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 64
- 238000001035 drying Methods 0.000 claims description 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 40
- 238000001816 cooling Methods 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 239000000843 powder Substances 0.000 claims description 28
- 239000007787 solid Substances 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 239000008346 aqueous phase Substances 0.000 claims description 24
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 20
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 20
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 18
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 18
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000012071 phase Substances 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 12
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 10
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 10
- 238000010791 quenching Methods 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 238000009987 spinning Methods 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 238000004440 column chromatography Methods 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003003 spiro group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- -1 dimethylphenyl Chemical group 0.000 claims description 5
- 239000012153 distilled water Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052755 nonmetal Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 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 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002541 furyl group Chemical group 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
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 2
- FQOBINBWTPHVEO-UHFFFAOYSA-N pyrazino[2,3-b]pyrazine Chemical compound N1=CC=NC2=NC=CN=C21 FQOBINBWTPHVEO-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 2
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 230000002035 prolonged effect Effects 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 11
- 238000012512 characterization method Methods 0.000 description 10
- 230000000171 quenching effect Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 2
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 2
- JZXXUZWBECTQIC-UHFFFAOYSA-N [Li].C1=CC=CC2=NC(O)=CC=C21 Chemical compound [Li].C1=CC=CC2=NC(O)=CC=C21 JZXXUZWBECTQIC-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229940126086 compound 21 Drugs 0.000 description 2
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
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Abstract
本发明属发光材料技术领域,具体涉及一种有机化合物及其制备方法和有机电致发光器件。其有益效果在于:提供了一种新的高效有机化合物及其制备方法。分子结构具有更平整的空间构象,具有更好的结晶性,有利于形成致密均一的薄膜;利用本发明所述有机化合物制备的有机电致发光器件,寿命有所提升、发光效率提高、所需的驱动电压降低。
Description
技术领域
本发明发光材料技术领域,涉及一种有机化合物及其制备方法和有机电 致发光器件。
背景技术
OLED材料分为发光材料、空穴传输材料、电子传输材料等。其中,空 穴传输材料通常具有低的最高已占据分子轨道(HOMO)值,在发光层中生成 的激子扩散到空穴传输层界面或者空穴传输层侧,最终导致在发光层内界面 的发光或者发光层内的电荷不均衡,从而在空穴传输层的界面上发光,使有 机电致发光器件的色纯度及效率变低,并且寿命变短。
向发光层和空穴传输层之间引入发光辅助层,可以有效避免上述技术问 题。
目前作为发光辅助层的材料有限,这类材料大多采用芴环结构,它们在 具备较高的空穴迁移率,同时具备较高的T1能量阻挡复合后的激子外扩到传 输层,提升器件的整体效率,同时合适的HOMO值降低了空穴从传输层到发 光层的传输势垒,使得器件驱动电压降低且寿命有所改善。
基于此,亟需一种新型有机化合物,以解决现有技术中的问题。
发明内容
本发明的目的之一是提供一种新型化合物;目的之二是提供新型化合物 的合成方法;目的之三是提供了一种应用所述新型化合物的有机电致发光器 件。
本发明公开了一种有机化合物,其分子式如通式(I)所示:
其中:
选自/> 化学键中任意一种;
Y1~Y8分别选自C、N中任意一种,且Y1~Y8中至少一个与其他不同,且 Y1~Y8中1~4个选取N;
R1选自取代或非取代的C1~C30的烷基、取代或非取代的C1~C30的烷 氧基、取代或非取代的C1~C30的烷巯基、取代或非取代的硅烷基中任意一 10种;
R2~R6分别选自取代或非取代的C5~C30的芳基、取代或非取代的3~30 元的杂环芳基、取代或非取代的C10~C30稠环基、取代或非取代的C5~C30 螺环基、单环或多环的C3~C30脂肪族环、单环或多环的C6~C30芳香族环 中任意一种,或将上述基团中至少一个碳原子取代为其他非金属原子所产生 15的基团;
L1、L2分别选自取代或非取代的C5~C30的芳基、取代或非取代的3~30 元的杂环芳基、取代或非取代的C10~C30稠环基、取代或非取代的C5~C30 螺环基、与相邻取代基连接形成单环或多环的C3~C30脂肪族环或C6~C30 芳香族环中任意一种,或将上述基团中至少一个碳原子取代为其他非金属原 子所产生的基团;
Ar1、Ar2分别选自取代或非取代的C6~C30的芳基、取代或非取代的的 3~30元的杂环芳基、取代或非取代的C10-C30的稠环基、取代或非取代的 C5-C30的螺环基、或与相邻取代基连接形成单环或多环的C3~C30的脂肪族 环或C6~C30的芳香族环中任意一种;或将上述基团中至少一个碳原子取代 为其他非金属原子所产生的基团。
优选的,R1选自烷基。
更优选的,R1选自甲基、乙基、丙基、异丙基、丁基、叔丁基、烷氧 基、烷巯基、硅烷基中至少一种。
优选的,L1、L2选取的基团中,取代碳原子的其他非金属原子选自氮、 氧、硫、硅中至少一种。
更优选的,L1、L2分别选自苯基、噻吩基、呋喃基、萘基或上述基团的 衍生物。
优选的,Ar1、Ar2选取的基团中,取代碳原子的其他非金属原子选自 氮、氧、硫、硅中至少一种。
更优选的,Ar1、Ar2分别选自萘基、菲基、苯基、甲基苯基、二甲基苯 基、三联苯基、联苯基、二苯并呋喃基、二苯并噻吩基、环戊二噻吩基、环 戊二呋喃基、二甲基芴基或上述基团的衍生物。
优选的,通式(I)中,结构选自喹喔啉、吡咯并吡啶、吡 啶并吡嗪、吡嗪并吡嗪、喹啉、萘啶、蝶啶中至少一种。
进一步地,所述“取代或非取代的”意指被选自以下的至少一种取代基 所取代:氘、卤素基团、腈基、羟基、羰基、酯基、甲硅烷基、硼基、取代 或非取代的烷基、取代或非取代的环烷基、取代或非取代的烷氧基、取代或 非取代的烯基、取代或非取代的烷基胺基、取代或非取代的杂环基胺基、取 代或非取代的芳基胺基、取代或非取代的芳基、和取代或非取代的杂环基, 或者被以上所示的取代基中的两个或更多个取代基相连接的取代基取代,或 者不具有取代基。
例如,“两个或更多个取代基相连接的取代基”可以包括联苯基。换言 之,联苯基可以为芳基,或者可以解释为两个苯基相连接的取代基。
优选的,所述有机化合物为如下分子式1~135所示结构:
中至少一种。
本发明还公开了所述有机化合物的制备方法,合成路径如下:
步骤1:制备中间体C
将反应物B加入反应容器中,加入无水四氢呋喃并氮气置换三次,随后 将反应体系降温至-78℃,滴加n-BuLi,搅拌2h;
将反应物A溶于四氢呋喃中,滴加至反应体系中,滴加完毕后升温至室 温搅拌10h;
加入蒸馏水终止反应,分液收集有机相,加入无水硫酸钠干燥。旋干得 到中间体C;
步骤2:制备中间体D
将中间体C加入反应容器中,降温至-10℃,加入三乙基硅烷,搅拌30 min,加入甲磺酸,升至室温搅拌过夜,加水终止反应,分液,收集有机相, 水相用二氯甲烷萃取三次,合并有机相,加入无水硫酸钠干燥,旋干得到白 色固体粉末D;
步骤3:制备中间体F
将中间体D加入反应容器中,加入四氢呋喃搅拌至充分溶解,加入叔丁 醇钾搅拌2h,缓慢滴加E,回流搅拌过夜,冷却至室温,加入饱和氯化铵溶 液淬灭反应,分液,收集有机相,水相用二氯甲烷萃取3次,合并有机相, 加入无水硫酸钠干燥,旋干后得白色固体粉末F;
步骤4:制备产物
将中间体F、G加入反应容器中,加入甲苯搅拌,氮气置换三次,依次 加入叔丁醇钠,三(二亚苄基丙酮)二钯,三叔丁基膦,升温至110℃搅拌过 夜;
冷却至室温,加水终止反应,分液,收集有机相,水相用二氯甲烷萃取 3次,合并有机相,加入无水硫酸钠干燥,柱层析得通式所示产品。
本发明还公开了一种有机电致发光器件,所述的有机化合物作为辅助发 光层材料。
本发明的有益效果在于:
1、本发明化合物所述分子结构具有更平整的空间构象,具有更好的结晶 性,有利于形成致密均一的薄膜;
2、利用本发明所述有机化合物制备的有机电致发光器件,寿命有所提 升、发光效率提高、所需的驱动电压降低。
附图说明
图1化合物1的核磁谱图;
图2化合物3的核磁谱图;
图3化合物7的核磁谱图;
图4化合物13的核磁谱图;
图5化合物98的核磁谱图;
图6化合物43的核磁谱图;
图7化合物21的核磁谱图;
图8化合物67的核磁谱图。
具体实施方式
下面结合实施例对本发明的具体实施方式作进一步描述,以下实施例仅 用于更加清楚地说明本发明的技术实施例,而不能以此来限制本发明的保护 范围。
实施例1
化合物1的制备:
反应方程式如下
中间体B1 200mmol加入三口瓶中,加入THF搅拌至充分溶解,氮气置 换三次,降温至-78℃,缓慢滴加正丁基锂183mmol,搅拌2h,将A1 166 mmol溶解在THF中,缓慢加入反应体系中,滴加完成后升至室温搅拌过 夜。缓慢加入稀盐酸终止反应,分液,收集有机相,水相用二氯甲烷萃取3 次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固体粉末C1 55g
将中间体C1 160mmol加入三口瓶中,加入二氯甲烷搅拌至充分溶解, 降温至-10℃,加入三乙基硅烷800mmol,搅拌30min,加入甲磺酸800 mmol,升至室温搅拌过夜,加水终止反应,分液,收集有机相,水相用二氯 甲烷萃取三次,合并有机相,加入无水硫酸钠干燥,旋干得到白色固体粉末 D1 50g。
将中间体D1 152mmol加入三口瓶中,加入四氢呋喃搅拌至充分溶解, 加入叔丁醇钾304mmol搅拌2h,缓慢滴加碘甲烷760mmol,回流搅拌过 夜,冷却至室温,加入饱和氯化铵溶液淬灭反应,分液,收集有机相,水相 用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固 体粉末F1 49g。
将中间体F1 58mmol、G1 62mmol加入三口中,加入甲苯搅拌,氮气置 换三次,依次加入叔丁醇钠117mmol,三(二亚苄基丙酮)二钯0.6mmol,三 叔丁基膦3mmol,升温至110℃搅拌过夜。冷却至室温,加水终止反应,分 液,收集有机相,水相用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠 干燥,柱层析得产品36g(yield:92%)。
如附图1所示,对产品进行了核磁表征,表征数据如下:
1H NMR(400MHz,CDCl3),δ(ppm):8.50(d,1H),8.34(m,2H),7.90(d,1H), 7.73(m,1H),7.61(d,1H),7.59(m,2H),7.55(d,4H),7.47(m,1H),7.43(m,2H), 7.39(m,7H),7.29(m,2H),7.22(m,1H),7.19(d,2H),6.95(d,1H),1.83(s,3H), 1.56(s,6H).
实施例2
化合物28的制备:
反应方程式如下
中间体B1 183mmol加入三口瓶中,加入THF搅拌至充分溶解,氮气置 换三次,降温至-78℃,缓慢滴加正丁基锂168mmol,搅拌2h,将A1 153 mmol溶解在THF中,缓慢加入反应体系中,滴加完成后升至室温搅拌过 夜。缓慢加入稀盐酸终止反应,分液,收集有机相,水相用二氯甲烷萃取3 次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固体粉末C153g。
将中间体C1 147mmol加入三口瓶中,加入二氯甲烷搅拌至充分溶解, 降温至-10℃,加入三乙基硅烷735mmol,搅拌30min,加入甲磺酸735 mmol,升至室温搅拌过夜,加水终止反应,分液,收集有机相,水相用二氯 甲烷萃取三次,合并有机相,加入无水硫酸钠干燥,旋干得到白色固体粉末 D1 49g。
将中间体D1 142mmol加入三口瓶中,加入四氢呋喃搅拌至充分溶解, 加入叔丁醇钾284mmol搅拌2h,缓慢滴加碘甲烷711mmol,回流搅拌过 夜,冷却至室温,加入饱和氯化铵溶液淬灭反应,分液,收集有机相,水相 用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固 体粉末F1 48g。
将中间体F1 56mmol、G1 60mmol加入三口中,加入甲苯搅拌,氮气置 换三次,依次加入叔丁醇钠112mmol,三(二亚苄基丙酮)二钯0.6mmol,三 叔丁基膦3mmol,升温至110℃搅拌过夜。冷却至室温,加水终止反应,分 液,收集有机相,水相用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠 干燥,柱层析得产品34g(yield:94%)。
如附图2所示,对产品进行了核磁表征,表征数据如下:
1H NMR(400MHz,CDCl3),δ(ppm):8.50(s,1H),8.02(m,1H),7.59(m,4H), 7.56(d,1H),7.54(d,4H),7.51(t,1H),7.40(m,6H),7.29(m,2H),7.23(d,4H), 7.18(m,2H),7.08(m,2H),6.98(m,2H),1.84(s,3H).
实施例3
化合物26的制备:
反应方程式如下
中间体B4 200mmol加入三口瓶中,加入THF搅拌至充分溶解,氮气置 换三次,降温至-78℃,缓慢滴加正丁基锂183mmol,搅拌2h,将A4 166 mmol溶解在THF中,缓慢加入反应体系中,滴加完成后升至室温搅拌过 夜。缓慢加入稀盐酸终止反应,分液,收集有机相,水相用二氯甲烷萃取3 次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固体粉末C4 54g
将中间体C4 157mmol加入三口瓶中,加入二氯甲烷搅拌至充分溶解, 降温至-10℃,加入三乙基硅烷783mmol,搅拌30min,加入甲磺酸313 mmol,升至室温搅拌过夜,加水终止反应,分液,收集有机相,水相用二氯 甲烷萃取三次,合并有机相,加入无水硫酸钠干燥,旋干得到白色固体粉末D4 48g。
将中间体D4 145mmol加入三口瓶中,加入四氢呋喃搅拌至充分溶解, 加入叔丁醇钾292mmol搅拌2h,缓慢滴加2-碘代丙烷730mmol,回流搅拌 过夜,冷却至室温,加入饱和氯化铵溶液淬灭反应,分液,收集有机相,水 相用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠干燥,旋干后得白色 固体粉末F4 53g。
将中间体F4 52mmol、G4 55mmol加入三口中,加入甲苯搅拌,氮气置 换三次,依次加入叔丁醇钠104mmol,三(二亚苄基丙酮)二钯0.5mmol,三 叔丁基膦2.5mmol,升温至110℃搅拌过夜。冷却至室温,加水终止反应, 分液,收集有机相,水相用二氯甲烷萃取3次,合并有机相,加入无水硫酸 钠干燥,柱层析得产品34g(yield:92%)。
如附图3所示,对产品进行了核磁表征,表征数据如下:
1H NMR(400MHz,CDCl3),δ(ppm):8.51(s,1H),8.04(m,1H),7.90(m,1H), 7.73(m,1H),7.63(d,1H),7.57(d,2H),7.51(d,1H),7.49(m,1H),7.47(m,5H), 7.43(m,3H),7.39(m,2H),7.37(m,8H),7.22(m,1H),1.57(d,6H),1.25(s,9H).
实施例4
化合物51的制备:
反应方程式如下
中间体B5 200mmol加入三口瓶中,加入THF搅拌至充分溶解,氮气置 换三次,降温至-78℃,缓慢滴加正丁基锂183mmol,搅拌2h,将A5 166 mmol溶解在THF中,缓慢加入反应体系中,滴加完成后升至室温搅拌过 夜。缓慢加入稀盐酸终止反应,分液,收集有机相,水相用二氯甲烷萃取3 次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固体粉末C5 54g
将中间体C5 157mmol加入三口瓶中,加入二氯甲烷搅拌至充分溶解, 降温至-10℃,加入三乙基硅烷783mmol,搅拌30min,加入甲磺酸313 mmol,升至室温搅拌过夜,加水终止反应,分液,收集有机相,水相用二氯 甲烷萃取三次,合并有机相,加入无水硫酸钠干燥,旋干得到白色固体粉末 D5 48g。
将中间体D5 145mmol加入三口瓶中,加入四氢呋喃搅拌至充分溶解, 加入叔丁醇钾290mmol搅拌2h,缓慢滴加碘甲烷725mmol,回流搅拌过 夜,冷却至室温,加入饱和氯化铵溶液淬灭反应,分液,收集有机相,水相 用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固 体粉末F4 44g。
将中间体F5 52mmol、G5 60mmol加入三口中,加入甲苯搅拌,氮气置 换三次,依次加入叔丁醇钠104mmol,三(二亚苄基丙酮)二钯0.5mmol,三 叔丁基膦2.5mmol,升温至110℃搅拌过夜。冷却至室温,加水终止反应, 分液,收集有机相,水相用二氯甲烷萃取3次,合并有机相,加入无水硫酸 钠干燥,柱层析得实施例37g(yield:90%)。
如附图4所示,对产品进行了核磁表征,表征数据如下:
1H NMR(400MHz,CDCl3),δ(ppm):8.54(s,1H),8.40(s,1H),7.90(t,1H), 7.74(m,4H),7.63(d,2H),7.55(d,2H),7.47(m,5H),7.39(m,7H),7.34(m,5H), 1.85(s,3H),1.57(s,6H).
实施例5
化合物98的制备:
反应方程式如下
中间体B3 162mmol加入三口瓶中,加入THF搅拌至充分溶解,氮气置 换三次,降温至-78℃,缓慢滴加正丁基锂148mmol,搅拌2h,将A1 135 mmol溶解在THF中,缓慢加入反应体系中,滴加完成后升至室温搅拌过 夜。缓慢加入稀盐酸终止反应,分液,收集有机相,水相用二氯甲烷萃取3 次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固体粉末C1 50g
将中间体C3 130mmol加入三口瓶中,加入二氯甲烷搅拌至充分溶解, 降温至-10℃,加入三乙基硅烷648mmol,搅拌30min,加入甲磺酸648 mmol,升至室温搅拌过夜,加水终止反应,分液,收集有机相,水相用二氯 甲烷萃取三次,合并有机相,加入无水硫酸钠干燥,旋干得到白色固体粉末 D3 45g。
将中间体D3 120mmol加入三口瓶中,加入四氢呋喃搅拌至充分溶解, 加入叔丁醇钾243mmol搅拌2h,缓慢滴加2-碘代丙烷608mmol,回流搅拌 过夜,冷却至室温,加入饱和氯化铵溶液淬灭反应,分液,收集有机相,水 相用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠干燥,旋干后得白色 固体粉末F1 45g。
将中间体F3 48mmol、G3 62mmol加入三口中,加入甲苯搅拌,氮气置 换三次,依次加入叔丁醇钠117mmol,三(二亚苄基丙酮)二钯0.6mmol,三 叔丁基膦3mmol,升温至110℃搅拌过夜。冷却至室温,加水终止反应,分 液,收集有机相,水相用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠 干燥,柱层析得产品33g(yield:89%)。
如附图5所示,对产品进行了核磁表征,表征数据如下:
1H NMR(400MHz,CDCl3),δ(ppm):8.64(d,1H),7.96(m,2H),7.89(m,3H), 7.73(m,1H),7.63(d,1H),7.58(m,4H),7.47(m,6H),7.34(m,2H),7.25(m,1H), 7.19(d,2H),7.13(m,4H),7.00(m,4H),2.64(m,1H),1.57(s,6H),1.05(d,6H).
实施例6
化合物43的制备:
反应方程式如下:
中间体B6 108mmol加入三口瓶中,加入THF搅拌至充分溶解,氮气置 换三次,降温至-78℃,缓慢滴加正丁基锂108mmol,搅拌2h,将A6 90 mmol溶解在THF中,缓慢加入反应体系中,滴加完成后升至室温搅拌过 夜。缓慢加入稀盐酸终止反应,分液,收集有机相,水相用二氯甲烷萃取3 次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固体粉末C6 33g
将中间体C6 85mmol加入三口瓶中,加入二氯甲烷搅拌至充分溶解,降 温至-10℃,加入三乙基硅烷425mmol,搅拌30min,加入甲磺酸425 mmol,升至室温搅拌过夜,加水终止反应,分液,收集有机相,水相用二氯 甲烷萃取三次,合并有机相,加入无水硫酸钠干燥,旋干得到白色固体粉末 D6 30g。
将中间体D6 80mmol加入三口瓶中,加入四氢呋喃搅拌至充分溶解,加 入叔丁醇钾160mmol搅拌2h,缓慢滴加碘甲烷400mmol,回流搅拌过夜, 冷却至室温,加入饱和氯化铵溶液淬灭反应,分液,收集有机相,水相用二 氯甲烷萃取3次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固体粉 末F6 30g。
将中间体F6 78mmol、G6 86mmol加入三口中,加入甲苯搅拌,氮气置 换三次,依次加入叔丁醇钠155mmol,三(二亚苄基丙酮)二钯0.8mmol,三 叔丁基膦4mmol,升温至110℃搅拌过夜。冷却至室温,加水终止反应,分 液,收集有机相,水相用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠 干燥,柱层析得产品52g(yield:93%)。1H NMR(400MHz,CDCl3),δ(ppm): 8.58(d,1H),8.42(s,1H),8.03(m,2H),7.9(m,1H),7.78(d,1H),7.73(m,1H), 7.67(m,1H),7.63(m,1H),7.54(m,1H),7.45(m,3H),7.42(m,3H),7.29(m,1H), 7.12(m,8H),2.95(s,3H),1.58(d,12H).
实施例7
化合物21的制备:
反应方程式如下:
中间体B7 162mmol加入三口瓶中,加入THF搅拌至充分溶解,氮气置 换三次,降温至-78℃,缓慢滴加正丁基锂162mmol,搅拌2h,将A7 135 mmol溶解在THF中,缓慢加入反应体系中,滴加完成后升至室温搅拌过 夜。缓慢加入稀盐酸终止反应,分液,收集有机相,水相用二氯甲烷萃取3 次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固体粉末C7 50g
将中间体C7 130mmol加入三口瓶中,加入二氯甲烷搅拌至充分溶解, 降温至-10℃,加入三乙基硅烷650mmol,搅拌30min,加入甲磺酸650 mmol,升至室温搅拌过夜,加水终止反应,分液,收集有机相,水相用二氯 甲烷萃取三次,合并有机相,加入无水硫酸钠干燥,旋干得到白色固体粉末 D7 45g。
将中间体D7 122mmol加入三口瓶中,加入四氢呋喃搅拌至充分溶解, 加入叔丁醇钾240mmol搅拌2h,缓慢滴加碘甲烷600mmol,回流搅拌过 夜,冷却至室温,加入饱和氯化铵溶液淬灭反应,分液,收集有机相,水相 用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固 体粉末F7 48g。
将中间体F7 80mmol、G7 86mmol加入三口中,加入甲苯搅拌,氮气置 换三次,依次加入叔丁醇钠155mmol,三(二亚苄基丙酮)二钯0.8mmol,三 叔丁基膦4mmol,升温至110℃搅拌过夜。冷却至室温,加水终止反应,分 液,收集有机相,水相用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠 干燥,柱层析得产品50g(yield:94%)。1H NMR(400MHz,CDCl3),δ(ppm): 8.77(d,1H),7.58(s,4H),7.54(m,5H),7.38(m,6H),7.32(m,1H),7.28(m,2H),7.17(m,8H),7.08(m,4H),1.73(s,3H),1.55(s,6H).
实施例8
化合物67的制备:
反应方程式如下:
中间体B8 200mmol加入三口瓶中,加入THF搅拌至充分溶解,氮气置 换三次,降温至-78℃,缓慢滴加正丁基锂200mmol,搅拌2h,将A8 167 mmol溶解在THF中,缓慢加入反应体系中,滴加完成后升至室温搅拌过 夜。缓慢加入稀盐酸终止反应,分液,收集有机相,水相用二氯甲烷萃取3 次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固体粉末C8 53g
将中间体C8 155mmol加入三口瓶中,加入二氯甲烷搅拌至充分溶解, 降温至-10℃,加入三乙基硅烷770mmol,搅拌30min,加入甲磺酸770 mmol,升至室温搅拌过夜,加水终止反应,分液,收集有机相,水相用二氯 甲烷萃取三次,合并有机相,加入无水硫酸钠干燥,旋干得到白色固体粉末 D8 46g。
将中间体D8 140mmol加入三口瓶中,加入四氢呋喃搅拌至充分溶解, 加入叔丁醇钾280mmol搅拌2h,缓慢滴加碘甲烷700mmol,回流搅拌过 夜,冷却至室温,加入饱和氯化铵溶液淬灭反应,分液,收集有机相,水相 用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固 体粉末F8 42g。
将中间体F8 80mmol、G8 86mmol加入三口中,加入甲苯搅拌,氮气置 换三次,依次加入叔丁醇钠155mmol,三(二亚苄基丙酮)二钯0.8mmol,三 叔丁基膦4mmol,升温至110℃搅拌过夜。冷却至室温,加水终止反应,分 液,收集有机相,水相用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠 干燥,柱层析得产品40g(yield:75%)。1H NMR(400MHz,CDCl3),δ(ppm): 7.88(d,1H),7.77(d,1H),7.68(m,2H),7.54(d,2H),7.32(m,21H),7.22(m,2H),1.84(s,3H),1.59(s,6H).
实施例9-21
参照实施例1-8的合成方法完成对化合物的制备。
分子式以及质谱如表1所示:
表1实施例6-21参数列表
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另外,需要说明,本发明其他化合物参照上述所列举的实施例的合成方 法即可获得,所以在此不再一一例举。
为了进一步说明本发明的有益效果,特设置了如下应用例:
应用例1
将实施例1中得到的化合物1作为发光辅助材料制备的有机电致发光器 件:
将费希尔公司涂层厚度为150nm的ITO玻璃基板放在蒸馏水中清洗2 次,超声波洗涤30min,用蒸馏水反复清洗2次,超声波洗涤10min,蒸馏 水清洗结束后,异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥,转 移到等离子体清洗机里,将上述基板洗涤5min,送到蒸镀机里。将化合物 HT以及P-dopant(3%)引入真空气相沉积设备的小室中,将所述设备的腔 室中的压力控制到10-6托。此后,向小室施加电流以使以上引入的材料蒸 发,从而在ITO基板上形成具有10nm厚度的空穴注入层。在形成的空穴注 入层上面真空蒸镀厚度为35nm的HT为空穴传输层,在上述空穴输送层上以 20nm的厚度真空沉积本发明的实施例1中的化合物来形成发光辅助层后制作 OLED发光器件的发光层,其结构包括OLED发光层所使用Host-R作为主体 材料,Dopant-R作为掺杂材料,掺杂材料掺杂比例为3%重量比,发光层膜 厚为40nm。
在上述发光层上真空蒸镀厚度为12nmTPBi作为空穴阻挡层,在上述空 穴阻挡层上以40nm的厚度真空沉积ET作为电子传输层;在上述电子传输层 上真空蒸镀厚度为1.0nm羟基喹啉锂(Liq),作为电子注入层。在电子注入 层上,制作膜厚为150nm的Al电极层,此层为阴极层使用。
如上所述地完成OLED发光器件后,用公知的驱动电路将阳极和阴极连 接起来,测量器件的电流效率以及器件的寿命。
相关材料的分子结构式如下所示:
应用例2-21
将实施例2-21对应的产物,用与应用例1相同的方式应用
为了进一步说明本发明相对与现有技术的先进性,设置如下对比例:
对比例1
参照应用例1的方法,将器件应用例1中使用的化合物1替换为对比例 材料作为发光辅助层,制备得到相应的有机电致发光器件。
对比例材料
针对应用例1-21及对比例1进行如下性能测试:
对上述制备的有机电致发光器件加以正向直流偏置电压,利用Photo Research公司的PR-650光度测量设备测定有机电致发光特性,亮度为 6000cd/m2条件下利用McScience公司的寿命测定装置测定了T95的寿命。结 果见表2-3:
表2测试性能参数表
表3器件性能参数测试表
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从表2可以看出,
器件性能显示,本发明应用例与对比例相比,在寿命、发光效率等方面 性能有显著提高。
主体一致的情况下,驱动电压降低0.1-0.2V,体现了本发明的进步性。
最后应说明的是:以上各实施例仅用以说明本发明的技术方案,而非对 其限制;尽管参照前述各实施例对本发明进行了详细的说明,本领域的普通 技术人员应当理解:其依然可以对前述各实施例所记载的技术方案进行修 改,或者对其中部分或者全部技术特征进行等同替换;而这些修改或者替 换,并不使相应技术方案的本质脱离本发明各实施例技术方案的范围。
Claims (10)
1.一种有机化合物,其特征在于,其分子式如通式(I)所示:
其中:
选自化学键、/> 中任意一种;
Y1~Y8分别选自C、N中任意一种,且Y1~Y8中至少一个与其他不同,且Y1~Y8中1~4个选取N;
R1选自取代或非取代的C1~C30的烷基、取代或非取代的C1~C30的烷氧基、取代或非取代的C1~C30的烷巯基、取代或非取代的硅烷基中任意一种;
R2~R6分别选自取代或非取代的C5~C30的芳基、取代或非取代的3~30元的杂环芳基、取代或非取代的C10~C30稠环基、取代或非取代的C5~C30螺环基、单环或多环的C3~C30脂肪族环、单环或多环的C6~C30芳香族环中任意一种,或将上述基团中至少一个碳原子取代为其他非金属原子所产生的基团;
L1、L2分别选自取代或非取代的C5~C30的芳基、取代或非取代的3~30元的杂环芳基、取代或非取代的C10~C30稠环基、取代或非取代的C5~C30螺环基、与相邻取代基连接形成单环或多环的C3~C30脂肪族环或C6~C30芳香族环中任意一种,或将上述基团中至少一个碳原子取代为其他非金属原子所产生的基团;
Ar1、Ar2分别选自取代或非取代的C6~C30的芳基、取代或非取代的的3~30元的杂环芳基、取代或非取代的C10-C30的稠环基、取代或非取代的C5-C30的螺环基、或与相邻取代基连接形成单环或多环的C3~C30的脂肪族环或C6~C30的芳香族环中任意一种;或将上述基团中至少一个碳原子取代为其他非金属原子所产生的基团。
2.根据权利要求1所述的有机化合物,其特征在于,R1选自甲基、乙基、丙基、异丙基、丁基、叔丁基、烷氧基、烷巯基、硅烷基。
3.根据权利要求1所述的有机化合物,其特征在于,L1、L2选取的基团中,取代碳原子的其他非金属原子选自氮、氧、硫、硅中至少一种。
4.根据权利要求1所述的有机化合物,其特征在于,L1、L2分别选自苯基、噻吩基、呋喃基、萘基或上述基团的衍生物。
5.根据权利要求1所述的有机化合物,其特征在于,Ar1、Ar2选取的基团中,取代碳原子的其他非金属原子选自氮、氧、硫、硅中至少一种。
6.根据权利要求1所述的有机化合物,其特征在于,Ar1、Ar2分别选自萘基、菲基、苯基、甲基苯基、二甲基苯基、三联苯基、联苯、二苯并呋喃、二苯并噻吩、环戊二噻吩、环戊二呋喃、二甲基芴或上述基团的衍生物。
7.根据权利要求1所述的有机化合物,其特征在于,通式(I)中,结构选自喹喔啉、吡咯并吡啶、吡啶并吡嗪、吡嗪并吡嗪、喹啉、萘啶、喋啶中至少一种。
8.根据权利要求1所述的有机化合物,其特征在于,所述有机化合物为如下分子式1-135所示结构:
中至少一种。
9.有机化合物的制备方法,其特征在于,权利要求1-8任意一项所述的有机化合物按照如下步骤制备:
合成路径如下:
步骤1:制备中间体C
将反应物B加入反应容器中,加入无水四氢呋喃并氮气置换三次,随后将反应体系降温至-78℃,滴加n-BuLi,搅拌2h;
将反应物A溶于四氢呋喃中,滴加至反应体系中,滴加完毕后升温至室温搅拌10h;
加入蒸馏水终止反应,分液收集有机相,加入无水硫酸钠干燥。旋干得到中间体C;
步骤2:制备中间体D
将中间体C加入反应容器中,降温至-10℃,加入三乙基硅烷,搅拌30min,加入甲磺酸,升至室温搅拌过夜,加水终止反应,分液,收集有机相,水相用二氯甲烷萃取三次,合并有机相,加入无水硫酸钠干燥,旋干得到白色固体粉末D;
步骤3:制备中间体F
将中间体D加入反应容器中,加入四氢呋喃搅拌至充分溶解,加入叔丁醇钾搅拌2h,缓慢滴加E,回流搅拌过夜,冷却至室温,加入饱和氯化铵溶液淬灭反应,分液,收集有机相,水相用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠干燥,旋干后得白色固体粉末F;
步骤4:制备产物
将中间体F、G加入反应容器中,加入甲苯搅拌,氮气置换三次,依次加入叔丁醇钠,三(二亚苄基丙酮)二钯,三叔丁基膦,升温至110℃搅拌过夜;
冷却至室温,加水终止反应,分液,收集有机相,水相用二氯甲烷萃取3次,合并有机相,加入无水硫酸钠干燥,柱层析得通式(1)所示产品。
10.一种有机电致发光器件,其特征在于,采用权利要求1-8任意一项所述的有机化合物作为辅助发光层材料。
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