JP2016534113A - ホウ素エステル縮合チオフェンモノマー - Google Patents

ホウ素エステル縮合チオフェンモノマー Download PDF

Info

Publication number
JP2016534113A
JP2016534113A JP2016536397A JP2016536397A JP2016534113A JP 2016534113 A JP2016534113 A JP 2016534113A JP 2016536397 A JP2016536397 A JP 2016536397A JP 2016536397 A JP2016536397 A JP 2016536397A JP 2016534113 A JP2016534113 A JP 2016534113A
Authority
JP
Japan
Prior art keywords
optionally substituted
independently
alkyl chain
compound
formula
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.)
Pending
Application number
JP2016536397A
Other languages
English (en)
Japanese (ja)
Other versions
JP2016534113A5 (enExample
Inventor
ハァ，ミンチエン
ロバート マシューズ，ジェイムズ
ロバート マシューズ，ジェイムズ
ニウ，ウェイジュン
ローレンス ウォレス，アーサー
ローレンス ウォレス，アーサー
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Corning Inc
Original Assignee
Corning Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Corning Inc filed Critical Corning Inc
Publication of JP2016534113A publication Critical patent/JP2016534113A/ja
Publication of JP2016534113A5 publication Critical patent/JP2016534113A5/ja
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • 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
    • C08G61/124—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 nitrogen atom in the ring
    • 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
    • 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
    • H10K85/10—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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H10K85/658—Organoboranes
    • 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
    • C08G2261/141—Side-chains having aliphatic units
    • C08G2261/1412—Saturated aliphatic 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
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
    • 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
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
    • 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
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/411—Suzuki reactions
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Inorganic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
JP2016536397A 2013-08-22 2014-08-20 ホウ素エステル縮合チオフェンモノマー Pending JP2016534113A (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361868720P 2013-08-22 2013-08-22
US61/868,720 2013-08-22
PCT/US2014/051776 WO2015026882A1 (en) 2013-08-22 2014-08-20 Boron ester fused thiophene monomers

Publications (2)

Publication Number Publication Date
JP2016534113A true JP2016534113A (ja) 2016-11-04
JP2016534113A5 JP2016534113A5 (enExample) 2017-10-05

Family

ID=51539322

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2016536397A Pending JP2016534113A (ja) 2013-08-22 2014-08-20 ホウ素エステル縮合チオフェンモノマー

Country Status (7)

Country Link
US (2) US9070882B2 (enExample)
EP (1) EP3036245A1 (enExample)
JP (1) JP2016534113A (enExample)
KR (1) KR20160045781A (enExample)
CN (1) CN105829325A (enExample)
TW (1) TWI617550B (enExample)
WO (1) WO2015026882A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020057780A (ja) * 2018-09-28 2020-04-09 東ソー株式会社 共役ポリマー、有機半導体層形成用溶液、有機半導体層、及び有機薄膜トランジスタ

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9070882B2 (en) * 2013-08-22 2015-06-30 Corning Incorporated Boron ester fused thiophene monomers
US9580556B2 (en) * 2015-01-29 2017-02-28 Corning Incorporated DPP with branched alkyl-chain or (and) fused thiophene with branched alkyl-chain and the related designing strategy to increase the molecular weight of their semi-conducting copolymers
CN112457328A (zh) * 2019-09-06 2021-03-09 康宁股份有限公司 通过Pd催化的直接(杂)芳基化或直接烯基化的基于FT4的有机半导体小分子的合成
CN115109046B (zh) * 2021-03-18 2024-09-03 常州强力先端电子材料有限公司 一种高产酸的酰亚胺磺酸酯类光产酸剂、组合物及应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120045720A1 (en) * 2010-08-20 2012-02-23 Murray Figov Developers and method of coloring lithographic printing members
JP2012111748A (ja) * 2010-11-05 2012-06-14 Sumitomo Chemical Co Ltd 置換カルコゲノアセン化合物及び該化合物を含有する有機半導体デバイス
JP2012180333A (ja) * 2010-06-30 2012-09-20 Canon Inc 新規有機化合物およびそれを有するエレクトロクロミック素子
JP2012528183A (ja) * 2009-05-28 2012-11-12 コーニング インコーポレイテッド 縮合チオフェン、その物品および方法
JP2013515089A (ja) * 2010-01-06 2013-05-02 コリア・ユニバーシティ・リサーチ・アンド・ビジネス・ファウンデーション フォトクロミック材料
WO2013066732A1 (en) * 2011-10-31 2013-05-10 Corning Incorporated Conjugated fused thiophenes, methods of making conjugated fused thiophenes, and uses thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7893191B2 (en) * 2007-02-28 2011-02-22 Corning Incorporated Fused thiophenes, methods for making fused thiophenes, and uses thereof
US8278346B2 (en) 2010-08-06 2012-10-02 Corning Incorporated Di-tin fused thiophene compounds and polymers and methods of making
CN102148879A (zh) 2010-10-22 2011-08-10 华为技术有限公司 端口映射方法、装置与通信系统
JP5836815B2 (ja) 2011-06-07 2015-12-24 キヤノン株式会社 新規有機化合物およびそれを有するエレクトロクロミック素子
EP2719702B1 (en) 2011-06-07 2016-05-11 Canon Kabushiki Kaisha Electrochromic element
US9070882B2 (en) * 2013-08-22 2015-06-30 Corning Incorporated Boron ester fused thiophene monomers

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012528183A (ja) * 2009-05-28 2012-11-12 コーニング インコーポレイテッド 縮合チオフェン、その物品および方法
JP2013515089A (ja) * 2010-01-06 2013-05-02 コリア・ユニバーシティ・リサーチ・アンド・ビジネス・ファウンデーション フォトクロミック材料
JP2012180333A (ja) * 2010-06-30 2012-09-20 Canon Inc 新規有機化合物およびそれを有するエレクトロクロミック素子
US20120045720A1 (en) * 2010-08-20 2012-02-23 Murray Figov Developers and method of coloring lithographic printing members
JP2012111748A (ja) * 2010-11-05 2012-06-14 Sumitomo Chemical Co Ltd 置換カルコゲノアセン化合物及び該化合物を含有する有機半導体デバイス
WO2013066732A1 (en) * 2011-10-31 2013-05-10 Corning Incorporated Conjugated fused thiophenes, methods of making conjugated fused thiophenes, and uses thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020057780A (ja) * 2018-09-28 2020-04-09 東ソー株式会社 共役ポリマー、有機半導体層形成用溶液、有機半導体層、及び有機薄膜トランジスタ
JP7342565B2 (ja) 2018-09-28 2023-09-12 東ソー株式会社 共役ポリマー、有機半導体層形成用溶液、有機半導体層、及び有機薄膜トランジスタ

Also Published As

Publication number Publication date
WO2015026882A1 (en) 2015-02-26
US20150252062A1 (en) 2015-09-10
US20150057420A1 (en) 2015-02-26
EP3036245A1 (en) 2016-06-29
CN105829325A (zh) 2016-08-03
TWI617550B (zh) 2018-03-11
US9580448B2 (en) 2017-02-28
KR20160045781A (ko) 2016-04-27
US9070882B2 (en) 2015-06-30
TW201509933A (zh) 2015-03-16

Similar Documents

Publication Publication Date Title
JP6418462B2 (ja) ジケトピロロピロール半導体材料、その調製方法およびその使用
CN109791987A (zh) 有机半导体化合物
US20160369045A1 (en) Novel fused naphthalene cyclohetero ring compounds, and methods and uses thereof
JP2016534113A (ja) ホウ素エステル縮合チオフェンモノマー
JP2015501298A (ja) ピロロ−ピロールジオン−チオフェンキノン化合物、調製方法およびその使用
KR101526169B1 (ko) 신규한 전자 끌게-주게-끌게 형의 나프탈렌 다이이미드 저분자 및 이를 이용한 유기전자소자
CN112638918A (zh) 亚甲基二氢吡嗪与稠合噻吩的半导体共聚物
CN106748625A (zh) 一种基于芘的多臂结构三并茚基有机光电材料及其制备方法和应用
KR101775991B1 (ko) 보론-함유 유기반도체 화합물 및 이의 제조 방법
US20150065722A1 (en) Fused thiophene ditin monomers
JP2016079291A (ja) モノマーセグメントとしてスルファニル置換チエノピラジン誘導体を含む共役系高分子化合物、その製造方法およびそれを用いた有機薄膜太陽電池
KR101855085B1 (ko) 셀레늄-함유 유기반도체 화합물 및 이의 제조 방법
CN112457328A (zh) 通过Pd催化的直接(杂)芳基化或直接烯基化的基于FT4的有机半导体小分子的合成
Sen et al. Synthesis and structure–property investigation of multi-arm oligothiophenes
Matsumoto et al. Synthesis, Molecular Structure, And Morphological Properties of Dendritic Tetra-2-thienylmethane
JP2021031391A (ja) π共役系ホウ素化合物、π共役系ホウ素化合物の製造方法および電子装置
CN113443957A (zh) 通过烷基格氏试剂与甲苯磺酸烷基酯之间的cu(i)催化的c-c偶联合成支链烷基醇
Li et al. Synthesis of a Novel Fluorene Derivative for Polyfluorenes: 7, 7'-di (5-bromothiophen-2-yl)-9, 9, 9', 9'-tetraoctyl-2, 2'-bifluorene

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20160517

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20170816

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20170816

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20180426

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20180508

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20180720

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20181010

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20190110

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20190508