CN1182179C - 二对甲苯基二烷基硅烷衍生物和由其生成的光致发光聚合物以及制备这些化合物的方法 - Google Patents
二对甲苯基二烷基硅烷衍生物和由其生成的光致发光聚合物以及制备这些化合物的方法 Download PDFInfo
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- CN1182179C CN1182179C CNB021057710A CN02105771A CN1182179C CN 1182179 C CN1182179 C CN 1182179C CN B021057710 A CNB021057710 A CN B021057710A CN 02105771 A CN02105771 A CN 02105771A CN 1182179 C CN1182179 C CN 1182179C
- Authority
- CN
- China
- Prior art keywords
- phenyl
- polymer
- photoluminescence
- derivative
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 238000005424 photoluminescence Methods 0.000 title claims abstract description 42
- 229920000642 polymer Polymers 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 title claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 239000000126 substance Substances 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 5
- 239000010703 silicon Substances 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000004714 phosphonium salts Chemical class 0.000 claims description 6
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 4
- 229920001002 functional polymer Polymers 0.000 abstract description 4
- 239000000178 monomer Substances 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000003086 colorant Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 14
- 238000001556 precipitation Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000031709 bromination Effects 0.000 description 7
- 238000005893 bromination reaction Methods 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- KFDXCXLJBAVJMR-UHFFFAOYSA-N dibutylsilane Chemical compound CCCC[SiH2]CCCC KFDXCXLJBAVJMR-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 5
- PQCPZAYVYWOSIA-UHFFFAOYSA-N (4-methylphenyl)-triphenylphosphanium Chemical compound C1=CC(C)=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PQCPZAYVYWOSIA-UHFFFAOYSA-N 0.000 description 4
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- -1 Di-p-tolyl dialkyl silane Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- CJJGYDCNINDDET-UHFFFAOYSA-N dibutyl-bis(4-methylphenyl)silane Chemical compound C=1C=C(C)C=CC=1[Si](CCCC)(CCCC)C1=CC=C(C)C=C1 CJJGYDCNINDDET-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- WRBOHOGDAJPJOQ-UHFFFAOYSA-N 9H-Carbazole-3-carboxaldehyde Chemical compound C1=CC=C2C3=CC(C=O)=CC=C3NC2=C1 WRBOHOGDAJPJOQ-UHFFFAOYSA-N 0.000 description 2
- WXOHDHVUBGOBIK-UHFFFAOYSA-N BrCC1=C(C=CC=C1)[SiH](CCCC)CCCC Chemical compound BrCC1=C(C=CC=C1)[SiH](CCCC)CCCC WXOHDHVUBGOBIK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 108010042833 7,8-diaminopelargonic acid aminotransferase Proteins 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UBYCDHUAZLATCI-UHFFFAOYSA-N BrCC1=C(C=CC=C1)[SiH](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound BrCC1=C(C=CC=C1)[SiH](C1=CC=CC=C1)C1=CC=CC=C1 UBYCDHUAZLATCI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- NJKDOKBDBHYMAH-UHFFFAOYSA-N dibutyl(dichloro)silane Chemical compound CCCC[Si](Cl)(Cl)CCCC NJKDOKBDBHYMAH-UHFFFAOYSA-N 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- RZWWGOCLMSGROE-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(C)C=C(C)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl RZWWGOCLMSGROE-UHFFFAOYSA-N 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
Abstract
Description
类 | Mn | Mw | Mw/Mn |
实施例8 | 2500 | 3700 | 1.48 |
实施例9 | 2800 | 4100 | 1.50 |
实施例10 | 2100 | 8300 | 3.8 |
实施例11 | 1500 | 4500 | 3.0 |
实施例12 | 1200 | 3700 | 3.0 |
类 | Tde(℃) | 碳产率(%) | Tg(℃) | UVλmax(nm) | PLλnax(nm) |
实施例8 | 175 | 48 | 105 | 347 | 440 |
实施例9 | 250 | 62 | 109 | 375 | 450,480 |
实施例10 | 178 | 44 | 108 | 353,314 | 480 |
实施例11 | 220 | 60 | 119 | 351,311 | 420 |
实施例12 | 240 | 64 | 116 | 387 | 520 |
Claims (8)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR464/1997 | 1997-01-10 | ||
KR1019970000464A KR100235235B1 (ko) | 1997-01-10 | 1997-01-10 | 기능성고분자 단량체로 유용한 유기실리콘 화합물 및 그 제조방법 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN98106183A Division CN1098855C (zh) | 1997-01-10 | 1998-01-09 | 二对甲苯基二烷基硅烷衍生物和由其生成光致发光聚合物以及制备这些化合物的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1379054A CN1379054A (zh) | 2002-11-13 |
CN1182179C true CN1182179C (zh) | 2004-12-29 |
Family
ID=19494383
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB021057710A Expired - Fee Related CN1182179C (zh) | 1997-01-10 | 1998-01-09 | 二对甲苯基二烷基硅烷衍生物和由其生成的光致发光聚合物以及制备这些化合物的方法 |
CN98106183A Expired - Fee Related CN1098855C (zh) | 1997-01-10 | 1998-01-09 | 二对甲苯基二烷基硅烷衍生物和由其生成光致发光聚合物以及制备这些化合物的方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN98106183A Expired - Fee Related CN1098855C (zh) | 1997-01-10 | 1998-01-09 | 二对甲苯基二烷基硅烷衍生物和由其生成光致发光聚合物以及制备这些化合物的方法 |
Country Status (4)
Country | Link |
---|---|
US (1) | US5990335A (zh) |
JP (1) | JP4160142B2 (zh) |
KR (1) | KR100235235B1 (zh) |
CN (2) | CN1182179C (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100451830C (zh) * | 2000-02-22 | 2009-01-14 | 布鲁尔科技公司 | 由化学气相沉积法沉积的有机聚合物抗反射涂层 |
USD742390S1 (en) * | 2013-02-22 | 2015-11-03 | Samsung Electronics Co., Ltd. | Graphic user interface for a display screen or a portion thereof |
USD743972S1 (en) * | 2013-02-22 | 2015-11-24 | Samsung Electronics Co., Ltd. | Graphic user interface for a display screen or a portion thereof |
RU2635559C1 (ru) * | 2016-08-04 | 2017-11-14 | Федеральное государственное бюджетное учреждение науки Институт высокомолекулярных соединений Российской академии наук | Способ получения кремнийорганического соединения |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1252681B (de) * | 1963-04-19 | 1967-10-26 | Dow Corning Corporation, Midland, Mich. (V. St. A.) | Verfahren zur Herstellung von Arylsilanen |
US3347897A (en) * | 1963-12-24 | 1967-10-17 | Monsanto Res Corp | Haloaryl organodisilaalkane compounds and use therefor |
IL25441A (en) * | 1966-03-23 | 1972-01-27 | Zilkha A | Trialkylsilyl benzamide derivatives |
WO1982004442A1 (en) * | 1981-06-19 | 1982-12-23 | Stangroom James Edward | Electroviscous fluids |
JP3143550B2 (ja) * | 1993-10-22 | 2001-03-07 | キヤノン株式会社 | 電子写真感光体、該電子写真感光体を有する電子写真装置及び装置ユニット |
JP2800699B2 (ja) * | 1994-08-31 | 1998-09-21 | 東亞合成株式会社 | 新規な分岐ポリシランおよびその製造方法 |
DE4442052A1 (de) * | 1994-11-25 | 1996-05-30 | Hoechst Ag | Konjugierte Polymere mit Hetero-Spiroatomen und ihre Verwendung als Elektrolumineszenzmaterialien |
-
1997
- 1997-01-10 KR KR1019970000464A patent/KR100235235B1/ko not_active IP Right Cessation
-
1998
- 1998-01-08 US US09/004,300 patent/US5990335A/en not_active Expired - Lifetime
- 1998-01-09 CN CNB021057710A patent/CN1182179C/zh not_active Expired - Fee Related
- 1998-01-09 CN CN98106183A patent/CN1098855C/zh not_active Expired - Fee Related
- 1998-01-12 JP JP00432998A patent/JP4160142B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CN1379054A (zh) | 2002-11-13 |
CN1196355A (zh) | 1998-10-21 |
KR100235235B1 (ko) | 1999-12-15 |
JPH1149784A (ja) | 1999-02-23 |
CN1098855C (zh) | 2003-01-15 |
US5990335A (en) | 1999-11-23 |
JP4160142B2 (ja) | 2008-10-01 |
KR19980065454A (ko) | 1998-10-15 |
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