JP5283479B2 - ポリマー - Google Patents
ポリマー Download PDFInfo
- Publication number
- JP5283479B2 JP5283479B2 JP2008275027A JP2008275027A JP5283479B2 JP 5283479 B2 JP5283479 B2 JP 5283479B2 JP 2008275027 A JP2008275027 A JP 2008275027A JP 2008275027 A JP2008275027 A JP 2008275027A JP 5283479 B2 JP5283479 B2 JP 5283479B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- polymer
- polymer according
- electron
- monomer
- 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
Links
- 229920000642 polymer Polymers 0.000 title claims description 74
- 239000000178 monomer Substances 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 229910052796 boron Inorganic materials 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 8
- 125000005620 boronic acid group Chemical group 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 230000005525 hole transport Effects 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 125000005259 triarylamine group Chemical group 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical class C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000002800 charge carrier Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 150000003918 triazines Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 description 28
- 125000001424 substituent group Chemical group 0.000 description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 11
- 125000006575 electron-withdrawing group Chemical group 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229920001400 block copolymer Polymers 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229920002098 polyfluorene Polymers 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- -1 nitro, carboxyl Chemical group 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- PZWLRLIAVLSBQU-UHFFFAOYSA-N 1,2-dioctyl-9h-fluorene Chemical group C1=CC=C2C3=CC=C(CCCCCCCC)C(CCCCCCCC)=C3CC2=C1 PZWLRLIAVLSBQU-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BYDIWLYAWBNCAQ-UHFFFAOYSA-N 9,9-bis(4-methoxyphenyl)fluorene Chemical compound C1=CC(OC)=CC=C1C1(C=2C=CC(OC)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BYDIWLYAWBNCAQ-UHFFFAOYSA-N 0.000 description 1
- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical compound C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 description 1
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical group C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N Phosphinothricin Natural products CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229920001746 electroactive polymer Polymers 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000004407 fluoroaryl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- 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]
-
- 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
- H10K85/115—Polyfluorene; Derivatives 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/124—Copolymers alternating
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/146—Side-chains containing halogens
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/148—Side-chains having aromatic units
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/149—Side-chains having heteroaromatic units
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/51—Charge transport
- C08G2261/514—Electron transport
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/52—Luminescence
- C08G2261/522—Luminescence fluorescent
- C08G2261/5222—Luminescence fluorescent electrofluorescent
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
(a)少なくとも1つの電子基で置換された芳香族炭化水素、又は
(b)電子求引ヘテロアリール
から選択される。
(a)少なくとも1つの電子求引基によって置換された芳香族炭化水素、又は
(b)電子求引ヘテロアリール
からそれぞれ独立して選択される。
水素、アルキル、アルコキシ、アリールアルキル及びヘテロアリールアルキルから選択される可溶化基、及び電子求引基から、R1−R5の少なくとも1つが電子求引基となるように、独立して選択される。最も好ましいnは1、すなわちArはフェニルである。
第1のタイプの電荷輸送体を注入するための第1の電極、
第2のタイプの電荷輸送体を注入するための第2の電極、
第1及び第2の電極の間に本発明の第1の側面のポリマーを含む発光層
を含む電子冷光放射性装置が提供される。
本発明の第1の側面のポリマーはこの装置において電子を輸送することが出来る。
(a)各Pがボロン酸基、ボロンエステル基及びボラン基から選択されるボロン誘導官能基である本発明の第3の側面のモノマー、並びに少なくとも2つの反応性ハロゲン官能基を有する芳香族モノマー、
(b)各Pが反応性ハロゲン官能基である本発明の第3の側面のモノマー、並びにボロン酸基、ボロンエステル基及びボラン基から選ばれる少なくとも2つのボロン誘導官能基を有する芳香族モノマー、
(c)各Pが反応性ハロゲン官能基であり、1つのPはボロン酸基、ボロンエステル基及びボラン基より選択されるボロン誘導官能基である本発明の第3の側面のモノマー、
ここで、反応混合物は芳香族モノマーの重合を触媒するのに適した触媒量の触媒、並びにボロン誘導官能基をボロネートアニオン基に変換するのに十分な量の塩基を含む。
。コモノマーの例としては、例えば、WO99/54385に開示されるトリアリールアミン及びWO00/46321及びWO00/55927に開示されるヘテロアリール単位を含む。
正孔輸送領域
電子輸送領域
発光領域
1)AmpacプログラムパッケージにおけるAM1
Ampac5.0ユーザーマニュアル、著作権1994 Semichen,7128
Summit,Shawnee,KS 66216
2)GaussianソフトウェアのZINDO
Gaussian98,改訂A.9,
M.J.Frisch,G.W.Trucks,H.B.Schlegel,G.EScusseria,
M.A.Robb,J.R.Cheeseman,V.G.Zakrzewski,J.A.Montgomery,Jr.,
R.E.Stratmann,J.C.Burant,S.Dapprich,J.M.Millan,
A.D.Daniels,K.N.Kudin,M.C.Strain,O.Farkas,J.Tomasi,
V.Barone,M.Cossi,R.Cammi,B.Mennuchi,C.Pomelli,C.Adamo,
S.Clifford,J.Ochterski,G.A.Petersson,P.Y.Ayala,Q.Cui,
K.Morokuma,D.K.Malick,A.D.Rabuck,K.Raghavachari,
J.B.Foresman,J.Cioslowski,J.V.Ortiz,A.G.Baboul,
B.B.Stefanov,G.Liu,A.Liashenko,P.Piskorz,I.Komaromi,
R.Gomperts,R.L.Martin,D.J.Fox,T.Keith,M.A.Al−Laham,
C.Y.Peng,A.Nanayakkara,M.Challacombe,P.M.W.Gill,
B.Johnson,W.Chen,M.W.Wong,J.L.Andres,Gonzalez,
M.Head−Gordon,E.S.Replogle,and J.A.Pople,
Gaussian,Inc.,Pittsburgh PA,1998.
式P1を有する発明のポリマーは、下記の表にまとめられた割合の次のモノマー
WO00/53656に記載されるプロセスに関連してスズキ重合によって製造された。
2,7−ジオキサラボラン−9,9−ジ−(n−オクチル)フルオレン
2,7−ジオキサラボラン−9,9−ジ−(4−トリフルオロメチルフェニル)フルオレン
N,N−ジ(4−ブロモフェニル)−N−(4−sec−ブチルフェニル)アミン(下記に示されるTFB繰返し単位を製造するため)
ジ[N−(4−ブロモフェニル)−N−(4−n−ブチルフェニル)]−フェニレン−1,4−ジアミン(下記に示されるPFB繰返し単位を製造するため)
1)Baytron P(登録商標)としてByer(登録商標)から入手可能なポリ(エチレンジオキシチオフェン)/ポリスチレンスルフォネート(PEDT/PSS)が、ガラス基板(Colorado,USAのApplied Filmsから入手可能)上に支持されたインジウム錫酸化物アノード上にスピンコートする
2)ポリマーP1を2%w/v濃度のキシレン溶液からPEDT/PSS上にスピンコートする
3)カルシムの第1層及びアルミニウムの第2層を含むカソードをポリマーP1上に気相
蒸着する
Claims (19)
- 電子求引ヘテロアリールが選択的に置換されたN含有ヘテロアリールである請求項1又は2に記載のポリマー。
- 電子求引ヘテロアリールが選択的に置換されたピリジン及びトリアジンから選択される請求項1又は2に記載のポリマー。
- 電子求引ヘテロアリールが1,3,5−トリアジン−2−イル又はオキサジアゾールである請求項1又は2に記載のポリマー。
- 第2の繰返し単位を含む請求項1ないし5のいずれかに記載のポリマー。
- 第2繰返し単位がトリアリールアミン及び複素環式芳香族化合物から選択される請求項1ないし6のいずれかに記載のポリマー。
- 電子を輸送することができる請求項1ないし7のいずれかに記載のポリマー。
- 正孔輸送及び/又は発光することができる少なくとも1つの区域を含む請求項8に記載のポリマー。
- 請求項1ないし9のいずれかに記載のポリマーを含む光学装置。
- 電子冷光放射性装置である請求項10に記載の光学装置。
- 第1のタイプの電荷輸送体を注入する第1電極、
第2のタイプの電荷輸送体を注入する第2電極、及び
第1及び第2電極の間に請求項1又は2のいずれかに記載のポリマーから構成される発光層、
を含む電子冷光放射性装置。 - 各Pが、ボロン酸基、ボロンエステル基及びボラン基並びに反応性ハロゲン基から選択される反応性ボロン誘導基から独立して選択される請求項13又は14に記載のポリマーの製造方法。
- (a)各Pが、ボロン酸基、ボロンエステル基及びボラン基から選ばれるボロン誘導官能基であるモノマー、並びに少なくとも2つの反応性ハロゲン官能基を有する芳香族モノマー、又は
(b)各Pが、反応性ハロゲン官能基であるモノマー、並びに、ボロン酸基、ボロンエステル基及びボラン基から選択される少なくとも2つのボロン誘導官能基を有する芳香族モノマー、又は
(c)1つのPが、反応性ハロゲン官能基であり、1つのPがボロン酸基、ボロンエステル基及びボラン基から選択されるボロン誘導官能基であるモノマー、
の反応混合物の重合を含み、
ここで、反応混合物は芳香族モノマーの重合を触媒するに適当な触媒量の触媒、並びにボロン誘導官能基をボロネートアニオン基に転換するに十分な量の塩基を含む請求項15に記載のポリマーの製造方法。 - 電子求引ヘテロアリールが選択的に置換されたN含有ヘテロアリールである請求項13〜16のいずれか1項に記載のポリマーの製造方法。
- 電子求引ヘテロアリールが選択的に置換されたピリジン及びトリアジンから選択される請求項13〜16のいずれか1項に記載のポリマーの製造方法。
- 電子求引ヘテロアリールが1,3,5−トリアジン−2−イル又はオキサジアゾールである請求項13〜16のいずれか1項に記載のポリマーの製造方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0225869.7A GB0225869D0 (en) | 2002-11-06 | 2002-11-06 | Polymer |
GB0225869.7 | 2002-11-06 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004549336A Division JP4293991B2 (ja) | 2002-11-06 | 2003-11-04 | ポリマー |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2009097016A JP2009097016A (ja) | 2009-05-07 |
JP2009097016A5 JP2009097016A5 (ja) | 2009-09-03 |
JP5283479B2 true JP5283479B2 (ja) | 2013-09-04 |
Family
ID=9947307
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004549336A Expired - Lifetime JP4293991B2 (ja) | 2002-11-06 | 2003-11-04 | ポリマー |
JP2008275027A Expired - Fee Related JP5283479B2 (ja) | 2002-11-06 | 2008-10-27 | ポリマー |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004549336A Expired - Lifetime JP4293991B2 (ja) | 2002-11-06 | 2003-11-04 | ポリマー |
Country Status (9)
Country | Link |
---|---|
US (2) | US7494720B2 (ja) |
EP (2) | EP1569980B1 (ja) |
JP (2) | JP4293991B2 (ja) |
KR (1) | KR100604500B1 (ja) |
CN (3) | CN101696220A (ja) |
AT (1) | ATE554121T1 (ja) |
AU (1) | AU2003285484A1 (ja) |
GB (1) | GB0225869D0 (ja) |
WO (1) | WO2004041902A2 (ja) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0225869D0 (en) * | 2002-11-06 | 2002-12-11 | Cambridge Display Tech Ltd | Polymer |
CN100556224C (zh) | 2003-07-08 | 2009-10-28 | 柯尼卡美能达控股株式会社 | 有机电致发光元件、照明装置及显示装置 |
CN101838387B (zh) * | 2004-12-03 | 2012-02-29 | 住友化学株式会社 | 水杨酸酯取代的共轭聚合物及器件 |
KR101249640B1 (ko) * | 2004-12-06 | 2013-04-01 | 에스케이이노베이션 주식회사 | 9-플루오렌-2-일-9-아릴-2,7-플루오레닐 단위 함유전기발광고분자 및 이를 이용한 전기발광소자 |
WO2006062323A1 (en) * | 2004-12-06 | 2006-06-15 | Sk Corporation | Electroluminescent polymer having 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit and electroluminescent device manufactured using the same |
GB2440934B (en) | 2006-04-28 | 2009-12-16 | Cdt Oxford Ltd | Opto-electrical polymers and devices |
WO2008016067A1 (fr) | 2006-08-01 | 2008-02-07 | Sumitomo Chemical Company, Limited | Composé polymère et dispositif polymère luminescent |
CN101511904A (zh) * | 2006-09-13 | 2009-08-19 | 住友化学株式会社 | 高分子化合物及高分子发光元件 |
KR101482817B1 (ko) * | 2007-10-24 | 2015-01-14 | 메르크 파텐트 게엠베하 | 광전자 디바이스 |
GB2454890B (en) * | 2007-11-21 | 2010-08-25 | Limited Cambridge Display Technology | Light-emitting device and materials therefor |
CN101591219B (zh) * | 2008-05-29 | 2012-08-08 | 中国科学院化学研究所 | 一种功能化聚芴类化合物及其中间体与应用 |
DE102008045663A1 (de) * | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Fluorverbrückte Assoziate für optoelektronische Anwendungen |
DE102009034194A1 (de) | 2009-07-22 | 2011-01-27 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
US20110077373A1 (en) * | 2009-09-29 | 2011-03-31 | General Electric Company | Polymer and optoelectronic device comprising the same |
TWI401274B (zh) * | 2009-10-16 | 2013-07-11 | Univ Nat Taiwan Science Tech | 新穎高分子聚合物及共聚合物及其製備方法 |
KR101663185B1 (ko) * | 2009-11-20 | 2016-10-06 | 삼성전자주식회사 | 플루오로기-함유 고분자, 상기 고분자를 포함한 유기 발광 소자 및 상기 유기 발광 소자의 제조 방법 |
WO2011093428A1 (ja) * | 2010-01-28 | 2011-08-04 | 住友化学株式会社 | 高分子化合物及びそれを用いてなる発光素子 |
US8617724B2 (en) | 2010-01-28 | 2013-12-31 | Sumitomo Chemical Company, Limited | Polymer compound and light emitting device using the same |
DE102010033080A1 (de) | 2010-08-02 | 2012-02-02 | Merck Patent Gmbh | Polymere mit Struktureinheiten, die Elektronen-Transport-Eigenschaften aufweisen |
JP5750247B2 (ja) * | 2010-08-31 | 2015-07-15 | 住友化学株式会社 | 有機薄膜トランジスタ及びその製造方法 |
GB2483269A (en) * | 2010-09-02 | 2012-03-07 | Cambridge Display Tech Ltd | Organic Electroluminescent Device containing Fluorinated Compounds |
JP5883570B2 (ja) * | 2011-03-25 | 2016-03-15 | 国立大学法人横浜国立大学 | 積層構造体 |
JP6094947B2 (ja) * | 2011-09-30 | 2017-03-15 | 三菱瓦斯化学株式会社 | フルオレン構造を有する樹脂及びリソグラフィー用下層膜形成材料 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
DE69427909T2 (de) | 1993-06-10 | 2002-04-04 | Cambridge Display Technology Ltd., Cambridge | Polymere für optische vorrichtungen |
US5523555A (en) | 1994-09-14 | 1996-06-04 | Cambridge Display Technology | Photodetector device having a semiconductive conjugated polymer |
GB9423692D0 (en) | 1994-11-23 | 1995-01-11 | Philips Electronics Uk Ltd | A photoresponsive device |
DE69608446T3 (de) * | 1995-07-28 | 2010-03-11 | Sumitomo Chemical Company, Ltd. | 2,7-aryl-9-substituierte fluorene und 9-substituierte fluorenoligomere und polymere |
KR0176331B1 (ko) * | 1996-05-16 | 1999-04-01 | 박원훈 | 전계 발광 소자용 플로렌계 교대 공중합체 및 이를 발광재료로 사용한 전계 발광 소자 |
JP3824385B2 (ja) | 1996-08-02 | 2006-09-20 | 三井化学株式会社 | 有機電界発光素子 |
US6309763B1 (en) | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
US5777070A (en) | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
GB9805476D0 (en) | 1998-03-13 | 1998-05-13 | Cambridge Display Tech Ltd | Electroluminescent devices |
KR100697861B1 (ko) | 1998-03-13 | 2007-03-22 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전장 발광 디바이스들 |
DE19846768A1 (de) * | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere enthaltend 2,7-Fluorenyleinheiten mit verbesserten Eigenschaften |
DE19846766A1 (de) * | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere, enthaltend spezielle Fluorenbausteine mit verbesserten Eigenschaften |
EP1155096B1 (en) | 1999-02-04 | 2005-03-09 | Dow Global Technologies Inc. | Fluorene copolymers and devices made therefrom |
DE60035970T2 (de) | 1999-03-05 | 2008-05-15 | Cambridge Display Technology Ltd. | Polymerherstellung |
AU2001235773A1 (en) | 2000-02-25 | 2001-09-03 | Cambridge Display Technology Limited | Electro-luminiscent polymers, their preparation and uses |
KR100354500B1 (ko) * | 2000-09-05 | 2002-09-30 | 한화석유화학 주식회사 | 플로렌계 중합체 및 이를 이용한 전기발광 소자 |
EP1220341B1 (en) * | 2000-12-28 | 2008-07-02 | Kabushiki Kaisha Toshiba | Organic electroluminescent device and display apparatus |
JP3972588B2 (ja) * | 2001-02-26 | 2007-09-05 | 淳二 城戸 | 有機電界発光素子 |
US7288617B2 (en) * | 2001-03-24 | 2007-10-30 | Merck Patent Gmbh | Conjugated polymers containing spirobifluorene units and fluorene units, and the use thereof |
GB0111549D0 (en) * | 2001-05-11 | 2001-07-04 | Cambridge Display Tech Ltd | Polymers, their preparation and uses |
KR100453809B1 (ko) * | 2001-07-21 | 2004-10-20 | 한국전자통신연구원 | 스피로비플루오렌 화합물 및 전기발광 고분자와 이를포함하는 전기발광 소자 |
EP1416028A1 (en) * | 2002-10-30 | 2004-05-06 | Covion Organic Semiconductors GmbH | New method for the production of monomers useful in the manufacture of semiconductive polymers |
GB0225869D0 (en) * | 2002-11-06 | 2002-12-11 | Cambridge Display Tech Ltd | Polymer |
-
2002
- 2002-11-06 GB GBGB0225869.7A patent/GB0225869D0/en not_active Ceased
-
2003
- 2003-11-04 US US10/533,989 patent/US7494720B2/en not_active Expired - Lifetime
- 2003-11-04 WO PCT/GB2003/004753 patent/WO2004041902A2/en active IP Right Grant
- 2003-11-04 CN CN200910140587A patent/CN101696220A/zh active Pending
- 2003-11-04 JP JP2004549336A patent/JP4293991B2/ja not_active Expired - Lifetime
- 2003-11-04 EP EP03778486A patent/EP1569980B1/en not_active Expired - Lifetime
- 2003-11-04 CN CN201010213318.XA patent/CN101870765B/zh not_active Expired - Fee Related
- 2003-11-04 AT AT03778486T patent/ATE554121T1/de active
- 2003-11-04 AU AU2003285484A patent/AU2003285484A1/en not_active Abandoned
- 2003-11-04 KR KR1020057008051A patent/KR100604500B1/ko active IP Right Grant
- 2003-11-04 EP EP10184752A patent/EP2363423A1/en not_active Withdrawn
- 2003-11-04 CN CNA2003801057632A patent/CN1726243A/zh active Pending
-
2008
- 2008-10-27 JP JP2008275027A patent/JP5283479B2/ja not_active Expired - Fee Related
- 2008-12-31 US US12/347,790 patent/US20090167170A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP1569980A2 (en) | 2005-09-07 |
CN101870765B (zh) | 2015-06-24 |
EP2363423A1 (en) | 2011-09-07 |
US7494720B2 (en) | 2009-02-24 |
CN1726243A (zh) | 2006-01-25 |
ATE554121T1 (de) | 2012-05-15 |
WO2004041902A2 (en) | 2004-05-21 |
CN101696220A (zh) | 2010-04-21 |
US20060228576A1 (en) | 2006-10-12 |
US20090167170A1 (en) | 2009-07-02 |
AU2003285484A1 (en) | 2004-06-07 |
GB0225869D0 (en) | 2002-12-11 |
WO2004041902A3 (en) | 2004-08-12 |
CN101870765A (zh) | 2010-10-27 |
KR100604500B1 (ko) | 2006-07-25 |
JP2009097016A (ja) | 2009-05-07 |
EP1569980B1 (en) | 2012-04-18 |
JP4293991B2 (ja) | 2009-07-08 |
JP2006505647A (ja) | 2006-02-16 |
AU2003285484A8 (en) | 2004-06-07 |
KR20060011819A (ko) | 2006-02-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5283479B2 (ja) | ポリマー | |
JP5704729B2 (ja) | 硬質アミン | |
TW525409B (en) | Electroluminescent devices | |
JP5393948B2 (ja) | 白色発光コポリマー、その調製および使用 | |
JP4620466B2 (ja) | アリールアミン単位を含む共役ポリマー、並びにそれらの調製及び使用 | |
JP5197687B2 (ja) | ポリマー及びその製造方法 | |
JP2008525608A5 (ja) | ||
EP1263834B1 (en) | Electro-luminescent polymers, their preparation and uses | |
JP2004532314A5 (ja) | ||
US6887973B2 (en) | Electro-luminescent polymers, their preparation and uses | |
KR100733177B1 (ko) | 중합체, 이들의 제조 및 용도 | |
JP5654729B2 (ja) | 有機発光デバイス | |
JP2009535795A5 (ja) | ||
JP2009509320A5 (ja) | ||
JP2007051208A (ja) | エレクトロルミネセンスポリマー及び有機el素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090716 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100330 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100621 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100624 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100727 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100730 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100826 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100831 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100930 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20110419 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20111004 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130528 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5283479 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |