JP2014503009A - 光起電重合体材料、その調製方法及び応用 - Google Patents
光起電重合体材料、その調製方法及び応用 Download PDFInfo
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- JP2014503009A JP2014503009A JP2013545006A JP2013545006A JP2014503009A JP 2014503009 A JP2014503009 A JP 2014503009A JP 2013545006 A JP2013545006 A JP 2013545006A JP 2013545006 A JP2013545006 A JP 2013545006A JP 2014503009 A JP2014503009 A JP 2014503009A
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- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
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Classifications
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- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/0248—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies
- H01L31/0256—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies characterised by the material
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- 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
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- 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
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- 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
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- H—ELECTRICITY
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Abstract
【選択図】図1
Description
単体M、単体D1及び単体D2をそれぞれ提供するステップと、
無酸素条件下で、前記単体M、単体D1及び単体D2を溶剤に溶かし、90℃〜110℃の温度及び触媒の条件下で20分間〜2時間Stille反応させて、光起電重合体材料を得るステップと、を含み、反応式は、
単体M、単体D1及び単体D2をそれぞれ提供するステップと、
無酸素条件下で、前記単体M、単体D1及び単体D2を溶剤に溶かし、90℃〜110℃の温度及び触媒の条件下で20分間〜2時間Stille反応させて、光起電重合体材料を得るステップと、を含む。反応式は、
氷浴条件下で、2−ブロモチオフェン(2.8mL、28.8mmol)、マグネシウムの屑(702mg、28.8mmol)をTHF(30mL)溶液に加え、ステップ毎に塩化亜鉛溶液(3.9g)を加え、30秒撹拌した後、混合溶液を得、氷浴を外し、さらに2,5−ジチオフェン−1,4−ジエチルベンゾエート(4.38g、11.5mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0)(266mg、2mol%)を該混合溶液に加え、12時間還流する。反応を中止、ろ過し、酢酸エステルで抽出を行い、溶剤を回転蒸発させて、粗生成物は溶離液(酢酸エステル/ノルマルヘキサン=1/9)を使用してシリカゲルカラムクロマトグラフィーによって分離してブリリアントイエロー液体(すなわち中間生成物1)(収率56%)を得る。mp103℃〜104℃,HNMR(CDCl3,400MHz デルタ7.81(s,2H),7.39(dd,J=4.8,1.2Hz,2H),7.08(m,4H),4.22(q,J=7.2Hz,4H),1.16(t,J=7.2Hz,6H)。
該中間生成物1(3.2g、8.3mmol)をテトラヒドロフラン(20mL)に溶かし、さらに4−ノルマルヘキシル臭化フェニルマグネシウム(1−ブロモ−4−n−ヘキシルベンゼン(10.2mL、50mmol)とマグネシウムの屑(1.2g、50mmol)との反応によって調製された)を滴下し、13時間還流反応させ、反応を中止し、酢酸エステルで抽出し、さらに無水硫酸マグネシウムで乾燥し、溶剤を回転蒸発させて、中間生成物を得、その後中間生成物を酢酸(100mL)と硫酸(5mL)との混合溶液に溶かし、4時間還流反応させた後反応を中止し、冷却し、酢酸エステルで抽出を行いさらに無水硫酸マグネシウムで乾燥する。溶剤を回転蒸発して粗生成物を得、溶離液ノルマルヘキサンを使用してシリカゲルカラムクロマトグラフィーによって黄色固体(すなわち中間生成物2)(収率42%)を得る。
中間生成物2(907mg、1mmol)N−ブロモスクシンイミド(392mg、2.2mmol)を30mlのクロロフォルムに溶かし、その後光を避けて12時間反応させる。反応停止後、クロロフォルムで抽出を行い、さらに飽和食塩水で洗浄し、最後に無水硫酸マグネシウムで乾燥する。粗生成物はメタノールで再結晶してブリリアントイエロー生成物すなわちM1を得る(92%)。
アルゴンガスの保護下でチオフェン(8.4g、0.10mol)を60mLTHFと混合し、ブチルリチウムのヘキサン溶液(ブチルリチウムのヘキサン溶液は73ml、0.21mol、2.88Mのブチルリチウムをヘキサン溶液に溶かすことによって得られる)を加え、2時間還流反応させるまで昇温し、加熱装置を外し、15℃の条件下でトリメチルスズ塩化物(41.9g、0.21mol)を加え、12時間撹拌反応させ、溶剤を回転蒸発して除去し、残り物は減圧蒸留し、0.1mmHg,220℃下で無色液体、すなわち2,5−ジ(トリメチルスズ)−チオフェンを得、収率は53%である。
単体D1b:5,5’−ジ(トリメチルスズ)−2,2’−ジチオフェンの調製方法は該単体D1aの調製方法を参照し、そのうち、「チオフェン」を「2,2’−ジチオフェン」に変更すれば単体D1bが得られる。収率は60%である。
単体D1d−1:2,5−ジ(トリメチルスズ)−3,3’−ジ[(エチルオクチルオキシ)メチル] ジオキサシクロヘプタジエンチオフェンの調製によって単体D1dの調製方法を説明する。
単体D1e−1:3,4−ジノルマルオクチル−2,5−ジ(トリメチルスズ)チオフェンの調製によって単体D1eの調製方法を説明する。
単体D1f−1:5−ノルマルオクチル−2,8−ジ(トリメチルスズ)チエノピロール−4,6−ジケトンの調製によって単体D1fの調製方法を説明する。
単体D2c−1:4,7−ジブロモ−5,6−ジ(ノルマルオクチルオキシ)ベンゾチアジアゾールはMacromolecules 2008, 41, 5559に開示された方法に基づいて調製する。収率は70%である。
窒素ガスの保護下で、単体M1、単体D1a:2, 5−ジ(トリメチルスズ)チオフェン、単体D2a−1:4, 7−ジブロモ−2−ノルマルオクチル−1, 2, 3−ベンゾトリアゾールを単体M1:単体D1a:単体D2a−1=1:2:1のモル比に基づいてトリス(ジベンジリデンアセトン)ジパラジウム(5.5mg、0.006mmol)、トリ−o−トリルホスフィン(14.6mg、0.048mmol)及びクロロベンゼン(5 mL)に加えて混合し、マイクロ波反応装置において30 秒反応させて、光起電重合体材料P(TPT−6−T−BTz−8)含有の深色溶液を得る。深色溶液をメタノール(1L)に注入し、ろ過して黒色沈殿を得、粗生成物はソックスレー抽出器によってそれぞれメタノール、アセトン、ノルマルへキサンを使用して24時間抽出し、さらにクロロフォルムを使用して溶解可能な部分を収集し、最後にメタノールでクロマトグラフィーを行う。固体を遠心収集し、真空乾燥して精製された後の光起電重合体材料を得る。収率は76%である。分子量分子量( GPC,THF,R.I):Mn=38600、Mw/Mn=2.1)。
図3に示すのは本発明実施例1の光起電重合体材料が活性層である光起電重合体材料太陽電池素子の構造で、構造はガラス基層31、透明陽極32、機能層33、陰極34を含み、該機能層は中間補助層331、活性層332を含む。そのうち、ガラス基層31は各種のガラスを含んでもよく、材質に対しては制限しないが、日光の透過を阻害できなければよい。透明陽極32はシート抵抗が10−20Ω/口である酸化インジウムスズ、すなわちITOであってもよいが、これに限定されるではない。中間補助層331はPEDOT:PSSであってもよいが、これに限定されず、PEDOTはポリ(3,3−エチレンジオキシチオフェン)で、PSSはポリ(ポリスチレンスルホン酸)で、活性層332は本発明実施例の光起電重合体材料である。本発明実施例の有機太陽電池素子3において、ガラス基層31と透明陽極32とは一体型の素子であり、ITOガラスとも呼ばれ、市販から入手できる。そのうち、活性層材料は、本発明実施例1の光起電重合体材料を電子供与体材料とし、[6,6]ベンゼン−C61−ブタン酸メチル(PCBMと略称する)を電子受容体とすることによって有機エレクトロルミネセンス素子を共同に構成する機能層を含む。本発明における光起電重合体材料を電子供与体材料としかつPCBMを電子受容体材料として回転塗布技術を使用し、金属アルミ電極は真空蒸着技術によって製作されて、光起電重合体材料太陽電池素子を得る。
氷浴条件下で、2−ブロモチオフェン(2.8mL、28.8mmol)、マグネシウムの屑(702mg、28.8mmol)をTHF(30mL)溶液に加え、ステップ毎に塩化亜鉛溶液(3.9g)を加え、30秒撹拌した後、混合溶液を得、氷浴を外し、さらに2,5−ジブロモテレフタル酸ジメチル(4.38g、11.5mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0)(266mg、2mol%)を該混合溶液に加え、12時間還流する。反応を中止、ろ過し、酢酸エステルで抽出を行い、溶剤を回転蒸発させて、粗生成物は溶離液(酢酸エステル/ノルマルヘキサン=1/9)を使用してシリカゲルカラムクロマトグラフィーによって分離してブリリアントイエロー液体(すなわち中間生成物1)(収率56%)を得る。mp103℃〜104℃,HNMR(CDCl3,400MHz デルタ7.81(s,2H),7.39(dd,J=4.8,1.2Hz,2H),7.08(m,4H),4.22(q,J=7.2Hz,4H),1.16(t,J=7.2Hz,6H)。
単体D1d−1:3,3−ジ(ノルマルオクチルオキシメチル)−3,4−ジヒドロ−2H−チエノ[3,4−b][1,4]ジオキサン−6,8−ジイル)ジ(トリメチルスズ)の調製によって単体D1dの調製方法を説明する。
単体D1f−1:1,3−ジ(トリメチルスズ)−5−ノルマルオクチル−チエノ[3,4−c]ピロール−4,6−ジケトンの調製によって単体D1fの調製方法を説明する。
Claims (10)
- 光起電重合体材料であって、以下の構造式を有し、
D1は以下の構造のうちの1種から選ばれ、
D2は以下の構造のうちの1種から選ばれ、
nは6〜20のいずれか1つの自然数で、xは1〜50のいずれか1つの自然数で、yは1〜50のいずれか1つの自然数で、2≦x+y≦100である、光起電重合体材料。 - 前記nは、6〜12のいずれか1つの自然数である、ことを特徴とする請求項1に記載の光起電重合体材料。
- 前記xは2〜40のいずれか1つの自然数で、前記yは2〜40のいずれか1つの自然数で、4≦x+y≦80である、ことを特徴とする請求項1に記載の光起電重合体材料。
- 前記光起電重合体材料の数平均分子量は、29100〜40000で、分子量分布係数は1.9〜2.5である、ことを特徴とする請求項1に記載の光起電重合体材料。
- 光起電重合体材料の調製方法であって、
単体M、単体D1及び単体D2をそれぞれ提供するステップと、
無酸素条件下で、前記単体M、単体D1及び単体D2を溶剤に溶かし、90℃〜110℃の温度及び触媒の条件下で20分間〜2時間Stille反応させて、光起電重合体材料を得るステップと、を含み、反応式は、
であり、
単体D1は以下の単体のうちの1種で、
D2は以下の構造のうちの1種で、
nは6〜20のいずれか1つの自然数で、xは1〜50のいずれか1つの自然数で、yは1〜50のいずれか1つの自然数で、2≦x+y≦100である、光起電重合体材料の調製方法。 - 前記nは6〜12のいずれか1つの自然数で、xは2〜40のいずれか1つの自然数で、yは2〜40のいずれか1つの自然数で、4≦x+y≦80である、ことを特徴とする請求項5に記載の光起電重合体材料の調製方法。
- 前記単体M、単体D1及び単体D2のモル比は、1〜2:2〜6:1〜2である、ことを特徴とする請求項5に記載の光起電重合体材料の調製方法。
- 前記触媒は、有機パラジウム、またはモル比が1:3〜10である有機パラジウムと有機リン配位子との混合物である、ことを特徴とする請求項5に記載の光起電重合体材料の調製方法。
- 前記触媒と単体Mとのモル比は、1:80〜120である、ことを特徴とする請求項5に記載の光起電重合体材料の調製方法。
- 請求項1〜4のいずれか1項に記載の光起電重合体材料の有機光電材料、有機太陽電池素子、有機電界効果トランジスタ素子、有機エレクトロルミネセンス素子、有機光記録素子及び有機レーザ素子における応用。
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CN103848960A (zh) * | 2012-11-28 | 2014-06-11 | 海洋王照明科技股份有限公司 | 含噻吩-苯-噻吩单元的聚合物及其制备方法和太阳能电池器件 |
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CN106536528B (zh) | 2014-07-29 | 2022-02-01 | 默克专利股份有限公司 | 基于四-杂芳基引达省并二噻吩的多环聚合物和它们的用途 |
CN108129661B (zh) * | 2018-01-03 | 2021-01-22 | 京东方科技集团股份有限公司 | 一种聚合物、量子点膜层及其制备方法 |
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KR102386679B1 (ko) * | 2014-05-26 | 2022-04-13 | 메르크 파텐트 게엠베하 | 테트라-아릴 인다세노디티오펜계 폴리시클릭 중합체 및 이들의 용도 |
JP7057063B2 (ja) | 2014-05-26 | 2022-04-19 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | テトラアリールインダセノジチオフェンに基づいた多環式ポリマーおよびそれらの使用 |
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US20130267657A1 (en) | 2013-10-10 |
CN103168062A (zh) | 2013-06-19 |
US8802812B2 (en) | 2014-08-12 |
EP2660264A1 (en) | 2013-11-06 |
EP2660264A4 (en) | 2016-04-20 |
CN103168062B (zh) | 2015-04-29 |
WO2012088698A1 (zh) | 2012-07-05 |
JP5688164B2 (ja) | 2015-03-25 |
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