CA2152922A1 - Diode electroluminescente reglable a base de copolymere multisequence, polymeres appropries a ladite application et oligomeres - Google Patents
Diode electroluminescente reglable a base de copolymere multisequence, polymeres appropries a ladite application et oligomeresInfo
- Publication number
- CA2152922A1 CA2152922A1 CA002152922A CA2152922A CA2152922A1 CA 2152922 A1 CA2152922 A1 CA 2152922A1 CA 002152922 A CA002152922 A CA 002152922A CA 2152922 A CA2152922 A CA 2152922A CA 2152922 A1 CA2152922 A1 CA 2152922A1
- Authority
- CA
- Canada
- Prior art keywords
- blocks
- thiophene
- block
- conjugated
- led
- 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.)
- Abandoned
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 34
- 229920001577 copolymer Polymers 0.000 title claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 37
- 229920001400 block copolymer Polymers 0.000 claims abstract description 31
- 229920006030 multiblock copolymer Polymers 0.000 claims abstract description 15
- 239000012876 carrier material Substances 0.000 claims abstract description 4
- 230000005525 hole transport Effects 0.000 claims abstract description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 63
- 229930192474 thiophene Natural products 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical class [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 230000005693 optoelectronics Effects 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- -1 p-phenylene-vinylene, vinylene-thiophene Chemical class 0.000 claims description 4
- 229920000548 poly(silane) polymer Polymers 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001722 carbon compounds Chemical class 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 150000003577 thiophenes Chemical class 0.000 claims 3
- 230000001276 controlling effect Effects 0.000 claims 2
- 150000002291 germanium compounds Chemical class 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229920000547 conjugated polymer Polymers 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- FDSYTWVNUJTPMA-UHFFFAOYSA-N 2-[3,9-bis(carboxymethyl)-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl]acetic acid Chemical compound C1N(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC2=CC=CC1=N2 FDSYTWVNUJTPMA-UHFFFAOYSA-N 0.000 description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- JQGGAELIYHNDQS-UHFFFAOYSA-N Nic 12 Natural products CC(C=CC(=O)C)c1ccc2C3C4OC4C5(O)CC=CC(=O)C5(C)C3CCc2c1 JQGGAELIYHNDQS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KXSFECAJUBPPFE-UHFFFAOYSA-N 2,2':5',2''-terthiophene Chemical compound C1=CSC(C=2SC(=CC=2)C=2SC=CC=2)=C1 KXSFECAJUBPPFE-UHFFFAOYSA-N 0.000 description 1
- FIGUWGHYSXYKCK-UHFFFAOYSA-N 2-iodo-3-octylthiophene Chemical compound CCCCCCCCC=1C=CSC=1I FIGUWGHYSXYKCK-UHFFFAOYSA-N 0.000 description 1
- FSEJXNVEILKEQU-UHFFFAOYSA-N 3,4-dibromo-2-thiophen-2-ylthiophene Chemical group BrC1=CSC(C=2SC=CC=2)=C1Br FSEJXNVEILKEQU-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 241000695274 Processa Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229960005363 aluminium oxide Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 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
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction 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
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
Classifications
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
-
- 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
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP92204100.9 | 1992-12-29 | ||
| EP92204100 | 1992-12-29 | ||
| EP93201637.1 | 1993-06-08 | ||
| EP93201637 | 1993-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2152922A1 true CA2152922A1 (fr) | 1994-07-07 |
Family
ID=26131900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002152922A Abandoned CA2152922A1 (fr) | 1992-12-29 | 1993-12-29 | Diode electroluminescente reglable a base de copolymere multisequence, polymeres appropries a ladite application et oligomeres |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPH08505167A (fr) |
| KR (1) | KR960700531A (fr) |
| AU (1) | AU5843894A (fr) |
| CA (1) | CA2152922A1 (fr) |
| FI (1) | FI953212A0 (fr) |
| WO (1) | WO1994015368A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105324370A (zh) * | 2013-06-18 | 2016-02-10 | 日产化学工业株式会社 | 噻吩衍生物及其利用以及噻吩衍生物的制备方法 |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE503039C2 (sv) * | 1994-07-19 | 1996-03-11 | Forskarpatent I Linkoeping Ab | Elektroluminescerande anordning samt sätt att framställa denna |
| EP0713999A1 (fr) * | 1994-11-24 | 1996-05-29 | Siemens Integra Verkehrstechnik Ag | Dispositif de signaux lumineux à diodes électroluminescentes |
| WO1997007654A1 (fr) * | 1995-08-21 | 1997-02-27 | Philips Electronics N.V. | Dispositif electroluminescent |
| US6165383A (en) * | 1998-04-10 | 2000-12-26 | Organic Display Technology | Useful precursors for organic electroluminescent materials and devices made from such materials |
| US6344284B1 (en) * | 1998-04-10 | 2002-02-05 | Organic Display Technology | Organic electroluminescent materials and devices made from such materials |
| US6361885B1 (en) | 1998-04-10 | 2002-03-26 | Organic Display Technology | Organic electroluminescent materials and device made from such materials |
| KR101278894B1 (ko) | 2001-04-27 | 2013-06-26 | 스미또모 가가꾸 가부시키가이샤 | 블록 공중합체 및 고분자 발광소자 |
| US6949762B2 (en) * | 2002-01-11 | 2005-09-27 | Xerox Corporation | Polythiophenes and devices thereof |
| US6872801B2 (en) * | 2002-01-11 | 2005-03-29 | Xerox Corporation | Polythiophenes and devices thereof |
| US6770904B2 (en) * | 2002-01-11 | 2004-08-03 | Xerox Corporation | Polythiophenes and electronic devices generated therefrom |
| US7141644B2 (en) | 2002-01-11 | 2006-11-28 | Xerox Corporation | Polthiophenes and devices thereof |
| US7279702B2 (en) | 2002-03-15 | 2007-10-09 | Koninklijke Philips Electronics N.V. | Electronic device, method, monomer and polymer |
| DE10248876B4 (de) * | 2002-10-18 | 2006-07-06 | H.C. Starck Gmbh | Verfahren zur Herstellung linearer organischer Oligomere |
| KR100518419B1 (ko) * | 2002-11-06 | 2005-09-29 | 엘지.필립스 엘시디 주식회사 | 유기전계발광소자 |
| JP2004273981A (ja) * | 2003-03-12 | 2004-09-30 | Konica Minolta Holdings Inc | 有機半導体および有機薄膜トランジスタ |
| GB0318817D0 (en) | 2003-08-11 | 2003-09-10 | Univ Cambridge Tech | Method of making a polymer device |
| GB0428403D0 (en) * | 2004-12-24 | 2005-02-02 | Cambridge Display Tech Ltd | Optical devices and their manufacture |
| KR101314985B1 (ko) * | 2005-02-10 | 2013-10-04 | 플렉스트로닉스, 인크 | 정공 주입/수송 층 조성물 및 장치 |
| EP1864300A4 (fr) * | 2005-03-16 | 2009-12-02 | Plextronics Inc | Copolymeres de poly(thiophenes) solubles dotes d'un meilleur rendement electronique |
| KR101275449B1 (ko) * | 2005-04-01 | 2013-06-14 | 카네기 멜론 유니버시티 | 위치규칙성 중합체, 폴리티오펜 및 블록 공중합체를포함하는 전도성 중합체의 리빙 합성 |
| DE112006003570T5 (de) * | 2005-12-28 | 2008-11-06 | Sumitomo Chemical Co., Ltd. | Blockcopolymer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2655655A1 (fr) * | 1989-12-07 | 1991-06-14 | Rhone Poulenc Chimie | Procede de preparation de polysilthiophenediyle et polymeres obtenus a l'issue de ce procede. |
| US5408109A (en) * | 1991-02-27 | 1995-04-18 | The Regents Of The University Of California | Visible light emitting diodes fabricated from soluble semiconducting polymers |
-
1993
- 1993-12-29 AU AU58438/94A patent/AU5843894A/en not_active Abandoned
- 1993-12-29 CA CA002152922A patent/CA2152922A1/fr not_active Abandoned
- 1993-12-29 JP JP6515043A patent/JPH08505167A/ja active Pending
- 1993-12-29 WO PCT/NL1993/000280 patent/WO1994015368A1/fr not_active Application Discontinuation
-
1995
- 1995-06-29 FI FI953212A patent/FI953212A0/fi not_active Application Discontinuation
- 1995-06-29 KR KR1019950702692A patent/KR960700531A/ko not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105324370A (zh) * | 2013-06-18 | 2016-02-10 | 日产化学工业株式会社 | 噻吩衍生物及其利用以及噻吩衍生物的制备方法 |
| CN105324370B (zh) * | 2013-06-18 | 2018-09-18 | 日产化学工业株式会社 | 噻吩衍生物及其利用以及噻吩衍生物的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08505167A (ja) | 1996-06-04 |
| FI953212A (fi) | 1995-06-29 |
| KR960700531A (ko) | 1996-01-20 |
| WO1994015368A1 (fr) | 1994-07-07 |
| FI953212A0 (fi) | 1995-06-29 |
| AU5843894A (en) | 1994-07-19 |
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