CN107827808A - A kind of derivative and its organic luminescent device containing carbazole class formation - Google Patents
A kind of derivative and its organic luminescent device containing carbazole class formation Download PDFInfo
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- CN107827808A CN107827808A CN201711201376.9A CN201711201376A CN107827808A CN 107827808 A CN107827808 A CN 107827808A CN 201711201376 A CN201711201376 A CN 201711201376A CN 107827808 A CN107827808 A CN 107827808A
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- unsubstituted
- substituted
- derivative
- class formation
- aryl
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- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 54
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims description 8
- -1 Amino Chemical group 0.000 claims description 22
- 238000006467 substitution reaction Methods 0.000 claims description 10
- 150000002894 organic compounds Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000005611 electricity Effects 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 24
- 150000001716 carbazoles Chemical class 0.000 abstract description 22
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 21
- 150000001875 compounds Chemical group 0.000 abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 5
- 238000005516 engineering process Methods 0.000 abstract description 3
- 230000009477 glass transition Effects 0.000 abstract description 3
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 230000005693 optoelectronics Effects 0.000 abstract 1
- 125000005259 triarylamine group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 239000000047 product Substances 0.000 description 44
- 238000003786 synthesis reaction Methods 0.000 description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000000470 constituent Substances 0.000 description 18
- 238000001819 mass spectrum Methods 0.000 description 18
- 238000005259 measurement Methods 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 0 Cc1ccc(cc[n]2*)c2c1 Chemical compound Cc1ccc(cc[n]2*)c2c1 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 4
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 3
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
- VCDOOGZTWDOHEB-UHFFFAOYSA-N 1-bromo-9h-carbazole Chemical class N1C2=CC=CC=C2C2=C1C(Br)=CC=C2 VCDOOGZTWDOHEB-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229940126142 compound 16 Drugs 0.000 description 3
- 229940127204 compound 29 Drugs 0.000 description 3
- 229940125878 compound 36 Drugs 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 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 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- SWSYIRGMNDPGJP-UHFFFAOYSA-N 1-bromo-9-methylcarbazole Chemical class BrC1=CC=CC=2C3=CC=CC=C3N(C1=2)C SWSYIRGMNDPGJP-UHFFFAOYSA-N 0.000 description 2
- AELBZZMQJAJEJW-UHFFFAOYSA-N 1-bromo-9-phenylcarbazole Chemical class BrC1=CC=CC(C2=CC=CC=C22)=C1N2C1=CC=CC=C1 AELBZZMQJAJEJW-UHFFFAOYSA-N 0.000 description 2
- QPTWWBLGJZWRAV-UHFFFAOYSA-N 2,7-dibromo-9h-carbazole Chemical class BrC1=CC=C2C3=CC=C(Br)C=C3NC2=C1 QPTWWBLGJZWRAV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- DDMAWVSNXVEYEG-UHFFFAOYSA-N [2-(2-fluorophenyl)phenyl]boronic acid Chemical class FC1=C(C=CC=C1)C=1C(=CC=CC=1)B(O)O DDMAWVSNXVEYEG-UHFFFAOYSA-N 0.000 description 2
- PQUOOLJXMHLQLU-UHFFFAOYSA-N [2-(4-nitrophenyl)phenyl]boronic acid Chemical class [N+](=O)([O-])C1=CC=C(C=C1)C=1C(=CC=CC=1)B(O)O PQUOOLJXMHLQLU-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000010719 annulation reaction Methods 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 229940125961 compound 24 Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 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 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical class BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
- 150000005658 6-bromoquinolines Chemical class 0.000 description 1
- MDXCDMSVFQIDGN-UHFFFAOYSA-N Brc(cc1)cc2c1c(ccc(Br)c1)c1[n]2-c1ccccc1 Chemical compound Brc(cc1)cc2c1c(ccc(Br)c1)c1[n]2-c1ccccc1 MDXCDMSVFQIDGN-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- WCZVLCSHTQSNSK-UHFFFAOYSA-N C(C1)C=CC=C1[n]1c(cc(c2ccccc2c(cc2)c3cc2-c2cccc4c2cccc4)c3c2)c2c2c1cc1-c3ccccc3C3C=CC(c4c(cccc5)c5ccc4)=CC3c1c2 Chemical compound C(C1)C=CC=C1[n]1c(cc(c2ccccc2c(cc2)c3cc2-c2cccc4c2cccc4)c3c2)c2c2c1cc1-c3ccccc3C3C=CC(c4c(cccc5)c5ccc4)=CC3c1c2 WCZVLCSHTQSNSK-UHFFFAOYSA-N 0.000 description 1
- LAUGBDGKGWXUHK-UHFFFAOYSA-N CC1NC=CC=C1c(cc1)cc2c1c(cccc1)c1c1c2cc(-c2cc3c(C(C4)C4(C=C4)c5cccnc5)c4c(cccc4)c4c3cc2C)c(Nc2ccccc2)c1 Chemical compound CC1NC=CC=C1c(cc1)cc2c1c(cccc1)c1c1c2cc(-c2cc3c(C(C4)C4(C=C4)c5cccnc5)c4c(cccc4)c4c3cc2C)c(Nc2ccccc2)c1 LAUGBDGKGWXUHK-UHFFFAOYSA-N 0.000 description 1
- QXBUYALKJGBACG-UHFFFAOYSA-N CN1c2ccccc2Sc2c1cccc2 Chemical compound CN1c2ccccc2Sc2c1cccc2 QXBUYALKJGBACG-UHFFFAOYSA-N 0.000 description 1
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 1
- QRVWDPIFENQXKJ-UHFFFAOYSA-N C[n](c1c2)c3cc4c(cccc5)c5c(ccc(N(c5ccc[s]5)c5ccc[s]5)c5)c5c4cc3c1cc(c1c3)c2c2ccccc2c1ccc3N(c1ccc[s]1)c1ccc[s]1 Chemical compound C[n](c1c2)c3cc4c(cccc5)c5c(ccc(N(c5ccc[s]5)c5ccc[s]5)c5)c5c4cc3c1cc(c1c3)c2c2ccccc2c1ccc3N(c1ccc[s]1)c1ccc[s]1 QRVWDPIFENQXKJ-UHFFFAOYSA-N 0.000 description 1
- SDFLTYHTFPTIGX-UHFFFAOYSA-N C[n]1c2ccccc2c2c1cccc2 Chemical compound C[n]1c2ccccc2c2c1cccc2 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 1
- JBFNQSFELCVNBC-UHFFFAOYSA-N Cc(cc1)cc2c1c1ccccc1[o]2 Chemical compound Cc(cc1)cc2c1c1ccccc1[o]2 JBFNQSFELCVNBC-UHFFFAOYSA-N 0.000 description 1
- URUCEYZTJIJMLX-UHFFFAOYSA-N Cc(cc1)cc2c1c1ccccc1[s]2 Chemical compound Cc(cc1)cc2c1c1ccccc1[s]2 URUCEYZTJIJMLX-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- LBOHDISKZVYEMX-UHFFFAOYSA-N Fc1ccc(c2ccccc2c(c2c3)cc([n](c4c5)-c6ccccc6)c3c4cc(c3c4)c5c(cccc5)c5c3ccc4F)c2c1 Chemical compound Fc1ccc(c2ccccc2c(c2c3)cc([n](c4c5)-c6ccccc6)c3c4cc(c3c4)c5c(cccc5)c5c3ccc4F)c2c1 LBOHDISKZVYEMX-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910010199 LiAl Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- IPQYJYUVHXZNSY-UHFFFAOYSA-N [2-(2-nitrophenyl)phenyl]boronic acid Chemical class [N+](=O)([O-])C1=C(C=CC=C1)C=1C(=CC=CC=1)B(O)O IPQYJYUVHXZNSY-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- OHXHYFUDSCKDFW-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c1ccc(c2ccccc2c(c2c3)cc4c3c3cc5c(cc(cc6)N(c7ccccc7)c7ccccc7)c6c(cccc6)c6c5cc3[n]4-c3cc4cccnc4cc3)c2c1 Chemical compound c(cc1)ccc1N(c1ccccc1)c1ccc(c2ccccc2c(c2c3)cc4c3c3cc5c(cc(cc6)N(c7ccccc7)c7ccccc7)c6c(cccc6)c6c5cc3[n]4-c3cc4cccnc4cc3)c2c1 OHXHYFUDSCKDFW-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000013519 translation Methods 0.000 description 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 description 1
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
The invention discloses a kind of derivative and its organic luminescent device containing carbazole class formation, it is related to organic optoelectronic materials technology.On the one hand, carbazole molecules are modified in compound structure of the invention, two phenyl ring is upgraded into Sanya benzene ring structure, adds the rigidity of structure, so as to not only increase the heat endurance of derivative, also reduce the possibility of molecule reunion；On the other hand, tri-arylamine group structure is introduced into carbazole condensed cyclic structure, its rigidity and also improves the stability of derivative the characteristics of non-co-planar simultaneously and reduce the possibility that molecule is reunited.Also, the glass transition temperature of carbazole derivates is improved greatly in the symmetrically or non-symmetrically structure using condensed ring carbazole as core.It is applied in organic luminescent device, material of main part can be used as, show the advantages of driving voltage is low, luminous efficiency is high, better than existing conventional OLED.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, more particularly to a kind of derivative containing carbazole class formation and its
Organic luminescent device.
Background technology
Organic electroluminescent LED (Organic Light Emitting Diode, OLED) has pure flat display
(Cathode Ray Tube, CRT) and the overall merit of liquid crystal display (Liquid Crystal Display, LCD), is described as
The FPD of 21 century and third generation Display Technique.
In general organic luminescent device (OLED) is the organic matter layer structure by being inserted between negative electrode, anode and negative electrode and anode
Into, the composition of device is transparent ITO anode, hole injection layer (TIL), hole transmission layer (HTL), luminescent layer (EL), hole
The negative electrodes such as barrier layer (HBL), electron transfer layer (ETL), electron injecting layer (EIL), LiAl are formed.
Luminescent material is divided into fluorescent material and phosphor material, and the forming method of luminescent layer is that phosphorus is adulterated in fluorescent host material
The method of method and fluorescent host material doping fluorescent (organic matter for including nitrogen) dopant of luminescent material (organic metal).It is conventional
Material of main part can generally be divided into several, such as hole transport material of main part, electric transmission material of main part, bipolar material of main part, lazy
Property material of main part, fluorescence complex material of main part and phosphorescent complexes material of main part.Wherein, carbazole and its derivative are because its is peculiar
Electric property, chemical property and Photophysics and be widely studied.
At present, the research of electroluminescent organic material is carried out extensively in academia and industrial quarters, a large amount of function admirables
Electroluminescent organic material be developed successively, but the technological industrialization process still faces many key issues how
The luminescent material for designing the more preferable carbazole class formation of new performance is adjusted, and is always that those skilled in the art are urgently to be resolved hurrily
Problem.
The content of the invention
It is an object of the invention to provide a kind of derivative and its organic luminescent device containing carbazole class formation.The present invention carries
The height of the derivative thermal stability containing carbazole class formation, the glass transition temperature height supplied, using the compound as in luminescent layer
Material of main part uses and manufactured organic luminescent device, shows the advantages of driving voltage is low, luminous efficiency is high, is function admirable
Luminous organic material.
The invention provides a kind of derivative containing carbazole class formation, its general formula of molecular structure is as shown in I：
Wherein, L is selected from substituted or unsubstituted C6~C50Aryl, substituted or unsubstituted C3~C50Heteroaryl, take
Generation or unsubstituted C2~C50Amino in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substitution or unsubstituted
C6~C50Aryl, substituted or unsubstituted C3~C50Heteroaryl in one kind.
Preferably, a kind of molecular structure I for example following II of derivative containing carbazole class formation provided by the present invention or
Any one representation in III：
Wherein, L is selected from substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl, take
Generation or unsubstituted C10~C30Aryl amine in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substitution or not
Substituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind.
Preferably, the one kind of the L in following structure：
Wherein, R1Selected from hydrogen, substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~C10Alcoxyl
Base, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl, substituted or unsubstituted C2~
C30Amino in one kind；R2~R7Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~
C10Alkoxy, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind.
Further preferably, a kind of derivative containing carbazole class formation of the present invention is in chemical constitution as follows
Any one：
Present invention also offers a kind of organic luminescent device, including first electrode, second electrode and it is placed in two electrode
Between one or more organic compound layers, one kind that described organic compound layer contains described in any one contains carbazoles
The derivative of structure.
Preferably, organic compound layer includes luminescent layer, contains carbazoles containing one kind described in any one in luminescent layer
The derivative of structure.
Beneficial effects of the present invention：
The invention provides a kind of derivative containing carbazole class formation, have the effect that：
On the one hand, carbazole ring be easily formed metastable cation, intramolecular with larger conjugated system and
The advantages of strong cyclic voltammetry method, generally there is higher heat endurance.But its carbazole small molecule is due to the limitation of structure,
Reunion is easily formed during solid phase, so as to cause to be quenched.The present invention compound structure in carbazole molecules are modified, by its two
Individual phenyl ring upgrades to Sanya benzene ring structure, adds the rigidity of structure, so as to not only increase the heat endurance of derivative, also drops
The possibility that low molecule is reunited；
On the other hand, rigid radical is introduced into carbazole condensed cyclic structure, makes its division center that there is rigidity and non-co-planar
The characteristics of, this feature also improves the stability of derivative and reduces the possibility of molecule reunion simultaneously.Also, with condensed ring click
The glass transition temperature of carbazole derivates is improved greatly for the symmetrically or non-symmetrically structure of core for azoles.
Derivative diffraction containing carbazole class formation is prepared into device, especially as material of main part, device is shown
The advantages of driving voltage is low, luminous efficiency is high, better than existing conventional OLED.What is shown in OLED luminescent devices is good
Application effect, this point shows that it has good industrialization prospect.
The derivative of the present invention is prepared by raw material of carbazole, because carbazole itself is one of coai-tar product, is easy to get, so
The preparation cost of the derivative of the present invention is small, is easy to industrialized production.
Embodiment：
It is clearly and completely described below in conjunction with the technical scheme of the embodiment of the present invention, it is clear that described implementation
Example only part of the embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, art technology
The every other embodiment that personnel are obtained under the premise of creative work is not made, belongs to protection scope of the present invention.
Alkyl of the present invention refers to minus the alkyl that a hydrogen atom forms in alkane molecule, and it can be straight chain alkane
Base, branched alkyl, cycloalkyl, example may include methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth
Base, amyl group, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refers to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, is left the total of univalent perssad
Claiming, it can be monocyclic aryl or fused ring aryl, and example may include phenyl, xenyl, naphthyl, anthryl, phenanthryl or pyrenyl etc., but
Not limited to this.
Heteroaryl of the present invention refers to the group that one or more of aryl aromatic core carbon substitutes to obtain by hetero atom
General name, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl
Base, example may include pyridine radicals, pyrrole radicals, pyridine radicals, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene
Fen base, benzofuranyl, dibenzofuran group, dibenzothiophenes base, carbazyl etc., but not limited to this.
Aryl amine of the present invention refers to the amine with armaticity substituent, i.e.-NH2,-NH- or nitrogen-containing group be connected to
On aromatic hydrocarbon, example may include following structure, but not limited to this
The invention provides a kind of derivative containing carbazole class formation, its general formula of molecular structure is as shown in I：
Wherein, L is selected from substituted or unsubstituted C6~C50Aryl, substituted or unsubstituted C3~C50Heteroaryl, take
Generation or unsubstituted C2~C50Amino in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substitution or unsubstituted
C6~C50Aryl, substituted or unsubstituted C3~C50Heteroaryl in one kind.
According to the present invention, the substituted alkyl, the aryl of substitution, the heterocyclic radical of substitution, the choosing of the substituent independence
From methyl, ethyl, isopropyl, the tert-butyl group, phenyl, naphthyl, anthryl, phenanthryl, benzo phenanthryl, base, pyrenyl, benzyl, methoxy
Base, methyl mercapto, phenoxy group, thiophenyl, fluorenyl, 9,9- dimethyl fluorenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl clicks
Oxazolyl, furyl, thienyl, cyano group, fluorine-based, deuterium base, triphenyl silicon substrate, trimethyl silicon substrate, phenothiazinyl, phenoxazine group, a word used for translation
Piperidinyl, piperidyl, pyridine radicals, pyrimidine radicals, xenyl, terphenyl, nitro etc., but not limited to this.
Preferably, a kind of general formula of molecular structure I such as II of derivative containing carbazole class formation provided by the present invention or
Any one representation in III：
Wherein, L is selected from substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl, take
Generation or unsubstituted C10~C30Aryl amine in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substitution or not
Substituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind.
Preferably, the one kind of L in following structure：
Wherein, R1Selected from hydrogen, substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~C10Alcoxyl
Base, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl, substituted or unsubstituted C2~
C30Amino in one kind；R2~R7Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~
C10Alkoxy, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind.
Further preferably, a kind of derivative containing carbazole class formation of the present invention, in chemical constitution as follows
Any one：
A kind of derivative containing carbazole class formation of the present invention, its syntheti c route is as shown in following two situation：First
Kind syntheti c route (L is now arylamine base class)
According to the present invention, compound a is prepared according to method as follows：
After the reaction of 2,7- bis- bromo- 9H- carbazoles and iodo thing, protected in nitrogen, tetra-triphenylphosphine palladium is catalyst, potassium carbonate
Under conditions of alkali, compound a is obtained by Suzuki coupling reactions with boronic acid compounds.
According to the present invention, target product I is prepared according to method as follows：
Compound a obtains compound c via annulation, reduction reaction.Nitrogen is protected, and tri-butyl phosphine is with palladium
Catalyst, sodium tert-butoxide be alkali under conditions of, compound c is obtained into target product by Buchwald-Hartwig coupling reactions
I。
Second of syntheti c route (L is now aryl, heteroaryl base class)
According to the present invention, compound d is prepared according to method as follows：
After the reaction of 2,7- bis- bromo- 9H- carbazoles and iodo thing, protected in nitrogen, tetra-triphenylphosphine palladium is catalyst, potassium carbonate
Under conditions of alkali, compound d is obtained by Suzuki coupling reactions with boronic acid compounds.
According to the present invention, target product I is prepared according to method as follows：
Compound d obtains compound e via annulation.Protected in nitrogen, tetra-triphenylphosphine palladium is catalyst, potassium carbonate
Under conditions of alkali, target product I is obtained by Suzuki coupling reactions with boronic acid compounds.
The present invention special limitation no to above-mentioned reaction, it is using popular response well-known to those skilled in the art
Can, the preparation method is simple to operate, is readily produced.
Present invention also offers a kind of organic luminescent device, including first electrode, second electrode and it is placed in two electrode
Between one or more organic compound layers, organic compound layer include hole injection layer, hole transmission layer, electronic blocking
Layer, luminescent layer, hole blocking layer, electron transfer layer, at least one layer of electron injecting layer；At least one in the organic compound layer
Layer includes a kind of derivative containing carbazole class formation of the present invention.
Preferably, a kind of derivative containing carbazole class formation of the present invention can be as the master in organic luminescent device
Body material.The device architecture of use is preferably specially：Described derivative/Ir (PPy) containing carbazole class formation3As luminous
Layer material, Alq3As electron-transporting material, NPB is used as hole transmission layer material, to manufacture having for construction same as below
Machine luminescent device：The derivative containing carbazole class formation described in ITO/NPB/:Ir(PPy)3/Alq3/LiF/Al.It is described organic
Electroluminescent device can be used for the application fields such as flat-panel monitor, lighting source, direction board, signal lamp.
The synthesis of [embodiment 1] compound 1
Intermediate a-1 synthesis
By the bromo- 9H- carbazoles (3.0g, 9.32mmol) of 2,7- bis-, iodomethane (1.5g, 10.25mmol), copper powder (1.8g,
27.95mmol) it is added to potassium carbonate (4.1g, 29.81mmol) in the 60mL of stirring o-dichlorohenzene, system is at 140 DEG C
Backflow 12 hours.At the end of reaction, 20mL distilled water is added thereto, makes to be extracted with ethyl acetate afterwards, merge organic phase, nothing
Water magnesium sulfate is concentrated after drying, and the bromo- 9- methyl-carbazoles of 2,7- bis- (1.9g, yield 60%) are obtained via column chromatography.
Weigh successively the bromo- 9- methyl-carbazoles (33.7g, 0.1mol) of 2,7- bis-, 4 '-nitro -2- biphenylboronic acids (50g,
0.2mol), potassium carbonate (69g, 0.5mol), 300mL water, 1L toluene are in 2L there-necked flasks, nitrogen protection, stirring at normal temperature, system
For white opacity, 1g tetra-triphenylphosphine palladiums are added after 20min, are heated to reflux 12 hours, system produces a large amount of solids, and suction filtration obtains
Solid product intermediate a-1 (51,7g, yield 90%).Mass spectrum m/z：575.64 (calculated values：575.61).Theoretical elemental contains
Measure (%) C37H25N3O4：C,77.20；H,4.38；N,7.30；O, 11.12 actual measurement constituent contents (%)：C,77.22；H,4.36；
N,7.31；O,11.11.The above results confirm that it is target product to obtain product.
Intermediate b-1 synthesis
Intermediate a-1 (287g, 0.5mol), ferric trichloride (162g, 1mol), 700mL dichloromethane are weighed successively in 1L
In there-necked flask, normal-temperature reaction filters after 24 hours, and filtrate washes two twice, then with saturated common salt with 300mL 10% salt pickling
It is secondary, merge organic phase after extraction, concentrated acid after anhydrous sodium sulfate drying, intermediate b-1 (yield 87%) is obtained via column chromatography.
Mass spectrum m/z：571.19 (calculated values：571.15).Theoretical elemental content (%) C37H21N3O4：C,77.75；H,3.70；N,7.35；
O, 11.20 actual measurement constituent contents (%)：C,77.75；H,3.73；N,7.32；O,11.20.The above results confirm that obtaining product is
Target product.
Intermediate c-1 synthesis
Intermediate b-1 (57.1g, 0.1mol), 7.2g palladium carbons, 1200mL tetrahydrofurans are weighed successively in 2L autoclaves,
Hydrogen Vapor Pressure is 10 atmospheric pressure, is reacted 24 hours at 40 DEG C, and reaction is filtered after terminating and removes palladium carbon, and filtrate is spin-dried for obtaining solid production
Thing intermediate c-1 (48.5g, yield 95%).Mass spectrum m/z：511.19 (calculated values：511.20).Theoretical elemental content (%)
C37H25N3：C,86.86；H,4.93；N, 8.21 actual measurement constituent contents (%)：C,86.87；H,4.92；N,8.21.The above results are demonstrate,proved
The real product that obtains is target product.
The synthesis of compound 1
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle
Sodium butoxide (22.8g, 238mmol) exists added to equal bromobenzene (119.8g, 768mmol) and intermediate c-1 (93.5g, 183mmol)
Solution in degassed toluene (2L), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to room
Temperature, filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and extracted with toluene, and merges organic phase,
It is evaporated under vacuo.The residue is filtered via silica gel, is recrystallized to give compound 1 (111.8g, yield
For 75%).Mass spectrum m/z：815.34 (calculated values：815.33).Theoretical elemental content (%) C61H41N3：C,89.79；H,5.06；
N, 5.15 actual measurement constituent contents (%)：C,89.78；H,5.07；N,5.15.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 2] compound 4
Change the bromobenzene in the synthesis of the compound 1 of embodiment 1 into the equimolar 1- tert-butyl groups -4- bromobenzenes, other steps
It is identical with the synthesis of embodiment 1, obtain target product compound 4.Mass spectrum m/z：1040.37 (calculated value：1040.42).Reason
Argument cellulose content (%) C77H73N3：C,88.89；H,7.07；N, 4.04 actual measurement constituent contents (%)：C,88.87；H,7.07；N,
4.06.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 3] compound 15
Change the bromobenzene in the synthesis of the compound 1 of embodiment 1 into equimolar 2- bromothiophenes, other steps with implementation
The synthesis of example 1 is identical, obtains target product compound 15.Mass spectrum m/z：840.17 (calculated values：840.11).Theoretical elemental content
(%) C53H33N3S4：C,75.77；H,3.96；N,5.00；S, 15.27 actual measurement constituent contents (%)：C,75.75；H,3.96；N,
5.02；S,15.27.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 4] compound 16
Intermediate a-2 synthesis
By the bromo- 9H- carbazoles (3.0g, 9.32mmol) of 2,7- bis-, iodobenzene (2.1g, 10.25mmol), copper powder (1.8g,
27.95mmol) it is added to potassium carbonate (4.1g, 29.81mmol) in the 60mL of stirring o-dichlorohenzene, system is at 140 DEG C
Backflow 12 hours.At the end of reaction, 20mL distilled water is added thereto, makes to be extracted with ethyl acetate afterwards, merge organic phase, nothing
Water magnesium sulfate is concentrated after drying, and the bromo- 9- phenyl-carbazoles (2.4g, yield 70%) of 2,7- bis- are obtained via column chromatography.
Weigh successively the bromo- 9- phenyl of 2,7- bis--carbazole (39.9g, 0.1mol), 4 '-nitro -2- biphenylboronic acids (50g,
0.2mol), potassium carbonate (69g, 0.5mol), 300mL water, 1L toluene are in 2L there-necked flasks, nitrogen protection, stirring at normal temperature, system
For white opacity, 1g tetra-triphenylphosphine palladiums are added after 20min, are heated to reflux 12 hours, system produces a large amount of solids, and suction filtration obtains
Solid product intermediate a-2 (51,7g, yield 90%).Mass spectrum m/z：637.64 (calculated values：637.68).Theoretical elemental contains
Measure (%) C42H27N3O4：C,79.11；H,4.27；N,6.59；O, 10.04 actual measurement constituent contents (%)：C,79.12；H,4.25；
N,6.59；O,10.04.The above results confirm that it is target product to obtain product.
Intermediate b-2 synthesis
Intermediate a-2 (331g, 0.5mol), ferric trichloride (162g, 1mol), 700mL dichloromethane are weighed successively in 1L
In there-necked flask, normal-temperature reaction filters after 24 hours, and filtrate washes two twice, then with saturated common salt with 300mL 10% salt pickling
It is secondary, merge organic phase after extraction, concentrated acid after anhydrous sodium sulfate drying, intermediate b-2 (yield 87%) is obtained via column chromatography.
Mass spectrum m/z：633.69 (calculated values：633.65).Theoretical elemental content (%) C42H23N3O4：C,79.61；H,3.66；N,6.63；
O, 10.10 actual measurement constituent contents (%)：C,79.61；H,3.65；N,6.63；O,10.11.The above results confirm that obtaining product is
Target product.
Intermediate c-2 synthesis
Intermediate b-2 (63.3g, 0.1mol), 7.2g palladium carbons, 1200mL tetrahydrofurans are weighed successively in 2L autoclaves,
Hydrogen Vapor Pressure is 10 atmospheric pressure, is reacted 24 hours at 40 DEG C, and reaction is filtered after terminating and removes palladium carbon, and filtrate is spin-dried for obtaining solid production
Thing intermediate c-2 (48.5g, yield 95%).Mass spectrum m/z：573.69 (calculated values：573.68).Theoretical elemental content (%)
C42H27N3：C,87.93；H,4.74；N, 7.32 actual measurement constituent contents (%)：C,87.93；H,4.73；N,7.34.The above results are demonstrate,proved
The real product that obtains is target product.
The synthesis of compound 16
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle
Sodium butoxide (22.8g, 238mmol) is added to equal bromobenzene (119.8g, 768mmol) and intermediate c-2 (104.8g, 183mmol)
Solution in degassed toluene (2L), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to room
Temperature, filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and extracted with toluene, and merges organic phase,
It is evaporated under vacuo.The residue is filtered via silica gel, is recrystallized to give compound 16 (111.8g, production
75%) rate is.Mass spectrum m/z：878.12 (calculated values：878.07).Theoretical elemental content (%) C66H43N3：C,90.28；H,
4.94；N, 4.79 actual measurement constituent contents (%)：C,90.28；H,4.95；N,4.77.The above results confirm that it is target to obtain product
Product.
The synthesis of [embodiment 5] compound 24
Change the iodomethane in the synthesis of the compound 1 of embodiment 1 into equimolar 6- bromoquinolines, other steps with implementation
The synthesis of example 1 is identical, obtains target product compound 24.Mass spectrum m/z：929.13 (calculated values：929.11).Theoretical elemental content
(%) C69H44N4：C,89.20；H,4.77；N, 6.03 actual measurement constituent contents (%)：C,89.22；H,4.75；N,6.03.Above-mentioned knot
Fruit confirms that it is target product to obtain product.
The synthesis of [embodiment 6] compound 29
Intermediate a-3 synthesis
By the bromo- 9H- carbazoles (3.0g, 9.32mmol) of 2,7- bis-, iodobenzene (2.1g, 10.25mmol), copper powder (1.8g,
27.95mmol) it is added to potassium carbonate (4.1g, 29.81mmol) in the 60mL of stirring o-dichlorohenzene, system is at 140 DEG C
Backflow 12 hours.At the end of reaction, 20mL distilled water is added thereto, makes to be extracted with ethyl acetate afterwards, merge organic phase, nothing
Water magnesium sulfate is concentrated after drying, and the bromo- 9- phenyl-carbazoles (2.4g, yield 70%) of 2,7- bis- are obtained via column chromatography.
Weigh successively the bromo- 9- phenyl of 2,7- bis--carbazole (39.9g, 0.1mol), 2 '-nitro -2- biphenylboronic acids (50g,
0.2mol), potassium carbonate (69g, 0.5mol), 300mL water, 1L toluene are in 2L there-necked flasks, nitrogen protection, stirring at normal temperature, system
For white opacity, 1g tetra-triphenylphosphine palladiums are added after 20min, are heated to reflux 12 hours, system produces a large amount of solids, and suction filtration obtains
Solid product intermediate a-3 (51,7g, yield 90%).Mass spectrum m/z：637.64 (calculated values：637.68).Theoretical elemental contains
Measure (%) C42H27N3O4：C,79.11；H,4.27；N,6.59；O, 10.04 actual measurement constituent contents (%)：C,79.12；H,4.25；
N,6.57；O,10.06.The above results confirm that it is target product to obtain product.
Intermediate b-3 synthesis
Intermediate a-3 (331g, 0.5mol), ferric trichloride (162g, 1mol), 700mL dichloromethane are weighed successively in 1L
In there-necked flask, normal-temperature reaction filters after 24 hours, and filtrate washes two twice, then with saturated common salt with 300mL 10% salt pickling
It is secondary, merge organic phase after extraction, concentrated acid after anhydrous sodium sulfate drying, intermediate b-3 (yield 87%) is obtained via column chromatography.
Mass spectrum m/z：633.69 (calculated values：633.65).Theoretical elemental content (%) C42H23N3O4：C,79.61；H,3.66；N,6.63；
O, 10.10 actual measurement constituent contents (%)：C,79.61；H,3.64；N,6.63；O,10.12.The above results confirm that obtaining product is
Target product.
Intermediate c-3 synthesis
Intermediate b-3 (63.3g, 0.1mol), 7.2g palladium carbons, 1200mL tetrahydrofurans are weighed successively in 2L autoclaves,
Hydrogen Vapor Pressure is 10 atmospheric pressure, is reacted 24 hours at 40 DEG C, and reaction is filtered after terminating and removes palladium carbon, and filtrate is spin-dried for obtaining solid production
Thing intermediate c-3 (48.5g, yield 95%).Mass spectrum m/z：573.69 (calculated values：573.68).Theoretical elemental content (%)
C42H27N3：C,87.93；H,4.74；N, 7.32 actual measurement constituent contents (%)：C,87.91；H,4.75；N,7.34.The above results are demonstrate,proved
The real product that obtains is target product.
The synthesis of compound 29
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle
Sodium butoxide (22.8g, 238mmol) is added to equal bromobenzene (119.8g, 768mmol) and intermediate c-3 (104.8g, 183mmol)
Solution in degassed toluene (2L), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to room
Temperature, filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and extracted with toluene, and merges organic phase,
It is evaporated under vacuo.The residue is filtered via silica gel, is recrystallized to give compound 29 (111.8g, production
75%) rate is.Mass spectrum m/z：878.12 (calculated values：878.07).Theoretical elemental content (%) C66H43N3：C,90.28；H,
4.94；N, 4.79 actual measurement constituent contents (%)：C,90.27；H,4.96；N,4.77.The above results confirm that it is target to obtain product
Product.
The synthesis of [embodiment 7] compound 36
Intermediate d-1 synthesis
Weigh successively the bromo- 9- phenyl of 2,7- bis--carbazole (39.9g, 0.1mol), 2 '-fluoro- 2- biphenylboronic acids (43g,
0.2mol), potassium carbonate (69g, 0.5mol), 300mL water, 1L toluene are in 2L there-necked flasks, nitrogen protection, stirring at normal temperature, system
For white opacity, 1g tetra-triphenylphosphine palladiums are added after 20min, are heated to reflux 12 hours, system produces a large amount of solids, and suction filtration obtains
Solid product intermediate d-1 (52.4g, yield 90%).Mass spectrum m/z：583.64 (calculated values：583.67).Theoretical elemental contains
Measure (%) C42H27NF2：C,86.43；H,4.66；N,2.40；F, 6.51 actual measurement constituent contents (%)：C,86.43；H,4.64；N,
2.41；F,6.52.The above results confirm that it is target product to obtain product.
Intermediate e-1 synthesis
Weigh successively intermediate d-1 (291.8g, 0.5mol), ferric trichloride (162g, 1mol), 700mL dichloromethane in
In 1L there-necked flasks, normal-temperature reaction is filtered after 24 hours, and filtrate is washed twice, then with saturated common salt with 300mL 10% salt pickling
Twice, organic phase is merged after extraction, concentrated acid after anhydrous sodium sulfate drying, obtaining intermediate e-1 via column chromatography, (yield is
87%).Mass spectrum m/z：633.69 (calculated values：633.65).Theoretical elemental content (%) C42H23NF2：C,87.03；H,4.00；N,
2.42；F, 6.56 actual measurement constituent contents (%)：C,87.03；H,4.01；N,2.42；F,6.54.The above results confirm to obtain product
For target product.
The synthesis of compound 36
Intermediate e-1 (63.3g, 0.1mol), 2 '-fluoro- 2- biphenylboronic acids (43g, 0.2mol), potassium carbonate are weighed successively
(69g, 0.5mol), 300mL water, 1L toluene are in 2L there-necked flasks, and nitrogen protection, stirring at normal temperature, system is white opacity,
1g tetra-triphenylphosphine palladiums are added after 20min, are heated to reflux 12 hours, system produces a large amount of solids, and suction filtration obtains solid crude product production
Thing.It is recrystallized to give compound 36 (62.1g, yield 90%).Mass spectrum m/z：695.84 (calculated values：695.85).Reason
Argument cellulose content (%) C54H33NF：C,93.21；H,4.78；N, 2.01 actual measurement constituent contents (%)：C,93.23；H,4.76；N,
2.01.The above results confirm that it is target product to obtain product.
[contrast Application Example]
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposed 30 minutes under ultraviolet light,
Then handled 10 minutes with plasma.The ito substrate after processing is then put into evaporated device.One layer of 70nm's of evaporation first
NPB is as hole transmission layer, evaporation rate 0.1nm/s, followed by the evaporation of luminescent layer, mixing evaporation CBP/Ir (PPy)3,
Doping concentration is 10wt%, evaporation rate 0.005nm/s, evaporation thickness 30nm, and 50nm Alq3 is then deposited as electricity
Sub- transport layer, evaporation rate 0.01nm/s, vacuum evaporation LiF and Al is as negative electrode, thickness successively on the electron transport layer
200nm。
[Application Example]
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposed 30 minutes under ultraviolet light,
Then handled 10 minutes with plasma.The ito substrate after processing is then put into evaporated device.One layer of 70nm's of evaporation first
The chemical combination in embodiment is deposited as hole transmission layer, evaporation rate 0.1nm/s, followed by the evaporation of luminescent layer, mixing in NPB
Thing/Ir (PPy)3, doping concentration 10wt%, evaporation rate 0.005nm/s, evaporation thickness 30nm, 50nm is then deposited
Alq3 as electron transfer layer, evaporation rate 0.01nm/s, on the electron transport layer vacuum evaporation LiF and Al conducts successively
Negative electrode, thickness 200nm.
The electron luminescence characteristic of the organic luminescent device of above method manufacture represents in the following table：
Result above shows that a kind of derivative containing carbazole class formation of the invention is applied in organic luminescent device,
Especially as material of main part, the advantages of driving voltage is low, luminous efficiency is high is shown, is organic light emission material of good performance
Material.
Obviously, the explanation of above example is only intended to help the method and its core concept for understanding the present invention.It should refer to
Go out, under the premise without departing from the principles of the invention, can also be to this hair for the those of ordinary skill of the technical field
Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.
Claims (6)
1. a kind of derivative containing carbazole class formation, it is characterised in that its general formula of molecular structure is as shown in I：
Wherein, L is selected from substituted or unsubstituted C6~C50Aryl, substituted or unsubstituted C3~C50Heteroaryl, substitution or
Unsubstituted C2~C50Amino in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6
~C50Aryl, substituted or unsubstituted C3~C50Heteroaryl in one kind.
A kind of 2. derivative containing carbazole class formation according to claim 1, it is characterised in that its general formula of molecular structure
As shown in II or III：
Wherein, L is selected from substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl, substitution or
Unsubstituted C10~C30Aryl amine in one kind；R is selected from substituted or unsubstituted C1~C10Alkyl, substitution or unsubstituted
C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind.
3. a kind of derivative containing carbazole class formation according to claim 1, it is characterised in that L is independently selected from such as
One kind in lower structure：
Wherein, R1Selected from hydrogen, substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~C10Alkoxy, substitution
Or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl, substituted or unsubstituted C2~C30Ammonia
One kind in base；R2~R7Independently selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~C10Alkane
Epoxide, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind.
4. a kind of derivative containing carbazole class formation according to claim 1, it is characterised in that selected from as followsization
Learn any one in structure：
5. a kind of organic luminescent device, it is characterised in that the organic luminescent device includes negative electrode, anode and is placed in two electricity
One or more organic compound layers between pole, described organic compound layer contain described in claim any one of 1-4
A kind of derivative containing carbazole class formation.
6. according to a kind of organic luminescent device described in claim 5, it is characterised in that the organic compound layer includes hair
Photosphere, contain a kind of derivative containing carbazole class formation described in claim any one of 1-4 in luminescent layer.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111320607A (en) * | 2018-12-17 | 2020-06-23 | 机光科技股份有限公司 | Organic compounds based on polycyclic heteroaromatic groups containing triphenylene and their applications |
| US11236075B2 (en) * | 2018-12-17 | 2022-02-01 | Luminescence Technology Corp. | Organic compound and organic electroluminescence device using the same |
-
2017
- 2017-11-27 CN CN201711201376.9A patent/CN107827808A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111320607A (en) * | 2018-12-17 | 2020-06-23 | 机光科技股份有限公司 | Organic compounds based on polycyclic heteroaromatic groups containing triphenylene and their applications |
| CN111320607B (en) * | 2018-12-17 | 2021-11-19 | 机光科技股份有限公司 | Organic compound with triphenylene-containing polycyclic heteroaromatic group as core and application thereof |
| US11236075B2 (en) * | 2018-12-17 | 2022-02-01 | Luminescence Technology Corp. | Organic compound and organic electroluminescence device using the same |
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