JPWO2013084805A1 - 含窒素芳香族化合物、有機半導体材料及び有機電子デバイス - Google Patents
含窒素芳香族化合物、有機半導体材料及び有機電子デバイス Download PDFInfo
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- JPWO2013084805A1 JPWO2013084805A1 JP2013548205A JP2013548205A JPWO2013084805A1 JP WO2013084805 A1 JPWO2013084805 A1 JP WO2013084805A1 JP 2013548205 A JP2013548205 A JP 2013548205A JP 2013548205 A JP2013548205 A JP 2013548205A JP WO2013084805 A1 JPWO2013084805 A1 JP WO2013084805A1
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Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- 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
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- 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
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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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
- H10K85/60—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
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
- H10K85/60—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
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Abstract
Description
そこで、光電変換効率を高めるべく、これら従来の材料に代わる新規な材料の開発が熱望されている。例えば、特許文献2では、フルオランテン骨格を有する化合物を用いた有機薄膜太陽電池が開示されているが、満足な光電変換効率を与えるものではない。
式(1)中、Rはそれぞれ独立に水素、炭素数1〜30の脂肪族炭化水素基、炭素数3〜50の芳香族基、炭素数4〜60の芳香族置換アルキル基、炭素数5〜60の芳香族置換アルケニル基または炭素数5〜60の芳香族置換アルキニル基を示し、Rのうち少なくとも1つは炭素数3〜50の芳香族基、炭素数4〜60の芳香族置換アルキル基、炭素数5〜60の芳香族置換アルケニル基または炭素数5〜60の芳香族置換アルキニル基から選ばれる基である。nは0〜4の整数を表す。nは1〜4の整数を示す。
式中Xは、ハロゲン原子、水酸基、ボロン酸、ボロン酸エステル、又はスルホニル基を示す。nは一般式(1)のnと同意である。
式(4)中、Rは一般式(1)のRと同意であり、Yは、Xと反応して脱離する官能基である。
縮合環である場合、2〜5個の環が縮合した縮合環であることが好ましい。
式(4)中、Rは一般式(1)のRと同意であり、YはXと反応して脱離する官能基である。
符号の説明;
1 基板、2 ゲート電極、3 絶縁層、4 有機半導体、5 ソース電極、6 ドレイン電極、7 基板、8 正極、9 有機半導体層、9−a 電子供与性有機半導体層、9−b 電子受容性有機半導体層、10 負極。
有機半導体層は本発明の化合物を含む。すなわち、式(1)で表される化合物を含む本発明の有機半導体材料を用いて形成される。本発明の有機半導体材料はp型有機半導体材料(以下p型有機材料という)、n型有機半導体材料(以下n型有機材料という)又は両者に使用される。式(1)で表される化合物を2種以上使用して、その1以上をp型有機材料成分とし、他の1以上をn型有機材料成分とすることができる。また、p型有機材料又はn型有機材料の一方を式(1)で表される化合物を含まない化合物とすることもできる。
膜厚150 nmのITO基板上に、合成例1で合成した化合物(100)を真空蒸着法により蒸着製膜し膜厚が約2.5 mmの有機半導体膜を形成した後、銀を真空蒸着法により170 nm蒸着製膜した。得られた素子をTOF法により、電荷移動度を評価した。その結果電界強度51.0 MV/cmにおいて、正孔移動度が3.9×10-2 cm2/Vsであった。
本発明の有機半導体材料の特性を、図1に示す構成の有機電界効果トランジスタを作成し、評価した。まず、約300nmの厚みの熱成長酸化ケイ素層を有するシリコンウェハ(nドープ)を、硫酸−過酸化水素水溶液で洗浄し、イソプロピルアルコールで煮沸した後、乾燥した。得られたシリコンウェハにフォトレジストをスピンコート後、フォトマスクを介して露光機により露光した。次いで、現像液で現像を行った後、イオン交換水で洗浄し、空気乾燥した。そのパターニングされたフォトレジストが塗布されたシリコンウェハ上に、真空蒸着法により、厚さ3nmのクロム、更にその上から50nmの金を蒸着した。そのシリコンウェハを、リムーバー溶液に浸すことでシリコンウェハ上にソース電極およびドレイン電極を作製した。ソース電極およびドレイン電極が作成されたシリコンウェハをアセトンで洗浄し、さらに、イソプロピルアルコールで煮沸し乾燥した有機電界効果トランジスタ基板を作製した。チャネル長はL=25μm、チャネル幅はW=15.6cmであった。
次に実施例1で得た化合物(100)を真空蒸着法により蒸着製膜し膜厚が50 nmの有機半導体膜を基板上に形成した。このようにして図1に示す構造を有する有機電界効果トランジスタを得た。得られた有機電界効果トランジスタの特性を評価したところ、移動度;4.0×10-1cm2/Vsであった。
実施例2において、化合物(100)の代わりに、ペンタセンを使用し、同様の操作を行い、有機電界効果トランジスタ素子を作製した。得られた素子を実施例2と同様に評価したところ、移動度;1.0×10-1cm2/Vsであった。
Claims (11)
- 下記一般式(3)で示される含窒素芳香族複素環化合物と下記一般式(4)で示される化合物を反応させることを特徴とする下記一般式(1)で示される含窒素芳香族複素環化合物の製造方法。
式(1)中、Rはそれぞれ独立に水素、炭素数1〜30の脂肪族炭化水素基、炭素数3〜50の芳香族基、炭素数4〜60の芳香族置換アルキル基、炭素数5〜60の芳香族置換アルケニル基または炭素数5〜60の芳香族置換アルキニル基を示し、Rのうち少なくとも1つは炭素数3〜50の芳香族基、炭素数4〜60の芳香族置換アルキル基、炭素数5〜60の芳香族置換アルケニル基または炭素数5〜60の芳香族置換アルキニル基を示す。nは1〜4の整数を示す。
式(3)中、Xは、ハロゲン原子、水酸基、ボロン酸、ボロン酸エステル、またはスルホニル基を示す。nは一般式(1)のnと同意である。
式(4)中、Rは一般式(1)のRと同意であり、Yは、Xと反応して脱離する官能基である。 - 請求項1に記載の含窒素芳香族複素環化合物を含有することを特徴とする有機半導体材料。
- 請求項5に記載の有機半導体材料から形成されたことを特徴とする有機半導体膜。
- 請求項5に記載の有機半導体材料を有機溶媒に溶解し、調製された溶液を塗布・乾燥する工程を経て、形成されたことを特徴とする有機半導体膜。
- 請求項5に記載の有機半導体材料を用いることを特徴とする有機電子デバイス。
- 有機電子デバイスが、発光素子、薄膜トランジスタ、又は光起電力素子のいずれかである請求項8に記載の有機電子デバイス。
- 有機電子デバイスが、薄膜トランジスタ、又は光起電力素子のいずれかである請求項8に記載の有機電子デバイス
- 有機電子デバイスが、有機薄膜トランジスタである請求項8に記載の有機電子デバイス。
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