CN100503554C - 一种合成tpd类光电材料的方法 - Google Patents
一种合成tpd类光电材料的方法 Download PDFInfo
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- CN100503554C CN100503554C CNB2006100481789A CN200610048178A CN100503554C CN 100503554 C CN100503554 C CN 100503554C CN B2006100481789 A CNB2006100481789 A CN B2006100481789A CN 200610048178 A CN200610048178 A CN 200610048178A CN 100503554 C CN100503554 C CN 100503554C
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- Prior art keywords
- bromo
- triphenylamine
- triphen amine
- reaction
- bromine
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 239000000463 material Substances 0.000 title claims abstract description 18
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 7
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 29
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- 125000001246 bromo group Chemical group Br* 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 11
- 239000012074 organic phase Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 238000010025 steaming Methods 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims 4
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 125000005259 triarylamine group Chemical group 0.000 claims 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 abstract description 4
- 238000005577 Kumada cross-coupling reaction Methods 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 abstract 3
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- -1 tri-arylamine group compound Chemical class 0.000 description 8
- YPIANBZIVBPMJS-UHFFFAOYSA-N 2-bromo-n,n-diphenylaniline Chemical compound BrC1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPIANBZIVBPMJS-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- MXCNKAOOHUCMBL-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1C1=CC(N)=CC=C1C1=CC=C(N)C=C1 MXCNKAOOHUCMBL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000006887 Ullmann reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- GPYDMVZCPRONLW-UHFFFAOYSA-N 1-iodo-4-(4-iodophenyl)benzene Chemical group C1=CC(I)=CC=C1C1=CC=C(I)C=C1 GPYDMVZCPRONLW-UHFFFAOYSA-N 0.000 description 2
- ZPEAXUUOTZDLNC-UHFFFAOYSA-N 2,3-dimethyl-n,n-diphenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C ZPEAXUUOTZDLNC-UHFFFAOYSA-N 0.000 description 2
- IULUNTXBHHKFFR-UHFFFAOYSA-N 4-methyl-n,n-diphenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 IULUNTXBHHKFFR-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 125000005266 diarylamine group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 150000002815 nickel Chemical class 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 230000005622 photoelectricity Effects 0.000 description 2
- FHMZRXAOGIFMFL-UHFFFAOYSA-N 3-methyl-n,n-diphenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 FHMZRXAOGIFMFL-UHFFFAOYSA-N 0.000 description 1
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 1
- BFIOFQDQYGNCCT-UHFFFAOYSA-N 4-methyl-n-phenyl-n-[4-[4-(n-phenylanilino)phenyl]phenyl]aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 BFIOFQDQYGNCCT-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000010751 Ullmann type reaction Methods 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
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CNB2006100481789A CN100503554C (zh) | 2006-08-23 | 2006-08-23 | 一种合成tpd类光电材料的方法 |
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CNB2006100481789A CN100503554C (zh) | 2006-08-23 | 2006-08-23 | 一种合成tpd类光电材料的方法 |
Publications (2)
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CN1911897A CN1911897A (zh) | 2007-02-14 |
CN100503554C true CN100503554C (zh) | 2009-06-24 |
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CNB2006100481789A Active CN100503554C (zh) | 2006-08-23 | 2006-08-23 | 一种合成tpd类光电材料的方法 |
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Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101284753B (zh) * | 2008-05-15 | 2010-07-28 | 北京理工大学 | 一种锰催化氧化的氯代芳基格氏试剂自身偶联反应方法 |
CN101830810B (zh) * | 2009-03-09 | 2013-01-23 | 中国科学院化学研究所 | 硝酸铈铵氧化偶联三芳胺合成n,n,n',n'-四芳基联苯二胺类化合物的方法 |
CN101963767B (zh) * | 2010-09-03 | 2011-12-28 | 邯郸光导重工高技术有限公司 | 一种单层正电性有机光导鼓的制备方法 |
CN104628915A (zh) * | 2015-02-12 | 2015-05-20 | 邯郸汉光科技股份有限公司 | 一类挂tpd侧基的高分子空穴传输功能材料的制备方法及应用 |
CN105348109B (zh) * | 2015-11-06 | 2017-03-29 | 烟台九目化学制品有限公司 | 一种oled中间体材料联三苯胺类衍生物的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4764625A (en) * | 1980-12-12 | 1988-08-16 | Xerox Corporation | Process for preparing arylamines |
US6811940B2 (en) * | 2001-09-19 | 2004-11-02 | Orient Chemical Industries, Ltd. | Mixed substance of triphenylamine dimers |
-
2006
- 2006-08-23 CN CNB2006100481789A patent/CN100503554C/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4764625A (en) * | 1980-12-12 | 1988-08-16 | Xerox Corporation | Process for preparing arylamines |
US6811940B2 (en) * | 2001-09-19 | 2004-11-02 | Orient Chemical Industries, Ltd. | Mixed substance of triphenylamine dimers |
Non-Patent Citations (2)
Title |
---|
二苯基联苯二胺的合成研究. 李春艳等.精细化工中间体,第35卷第3期. 2005 |
二苯基联苯二胺的合成研究. 李春艳等.精细化工中间体,第35卷第3期. 2005 * |
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CN1911897A (zh) | 2007-02-14 |
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