JPH11284250A - Phenazinone derivative and photoelectric transducer using the same - Google Patents
Phenazinone derivative and photoelectric transducer using the sameInfo
- Publication number
- JPH11284250A JPH11284250A JP8007598A JP8007598A JPH11284250A JP H11284250 A JPH11284250 A JP H11284250A JP 8007598 A JP8007598 A JP 8007598A JP 8007598 A JP8007598 A JP 8007598A JP H11284250 A JPH11284250 A JP H11284250A
- Authority
- JP
- Japan
- Prior art keywords
- phenazinone
- group
- derivative
- formula
- photoelectric conversion
- 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
Links
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
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- 125000000217 alkyl group Chemical group 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
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- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Photovoltaic Devices (AREA)
- Led Devices (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は新しい有機光電変換
素子に関するものであり、本発明の有機光電変換素子
は、太陽電池、電気整流器、トランジスター、整流用ダ
イオード、フォトダイオード、発光ダイオードあるいは
スイッチ等としてエレクロニクスまたはオプトエレクト
ロニクスの関連する工業において一般に広く応用するこ
とができる。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a new organic photoelectric conversion element, and the organic photoelectric conversion element of the present invention is used as a solar cell, an electric rectifier, a transistor, a rectifying diode, a photodiode, a light emitting diode or a switch. It is generally widely applicable in the electronics or optoelectronics related industries.
【0002】[0002]
【従来の技術】有機光電変換素子としてはp-型有機半導
体と仕事関数の小さな金属薄膜とを組み合わせたショッ
トキー接合型素子が知られており、Al/メタルフリーフ
タロシアニン/Auの組み合わせ、Al/ポリ-3-メチルチ
オフェン/Auの組み合わせが研究されている。本発明者
らにより、すでに特開昭59−28388号公報および
特開平3−91269号公報において有機二層型光電変
換素子が示されている。2. Description of the Related Art As an organic photoelectric conversion element, a Schottky junction element in which a p-type organic semiconductor and a metal thin film having a small work function are combined is known, and a combination of Al / metal-free phthalocyanine / Au, Al / Poly-3-methylthiophene / Au combinations have been studied. The present inventors have already disclosed an organic two-layer photoelectric conversion element in JP-A-59-28388 and JP-A-3-91269.
【0003】[0003]
【発明が解決しようとする課題】しかしながら、ショッ
トキー接合型素子は変換効率が低く、耐久性もよくない
という欠点が知られている。有機二層型光電変換素子は
p型、n型という2種類の材料を用意しなければいけな
い。また、性能のよいn型有機材料が少ないという欠点
がある。本発明者は特開平5−259434号公報にお
いて、1つの分子にドナーとアクセプターをもつ新規の
有機整流素子材料を提供したが、可視領域の光の吸収は
ないため、光電変換素子として利用できない。However, it is known that the Schottky junction type element has low conversion efficiency and poor durability. For the organic two-layer photoelectric conversion element, two types of materials, p-type and n-type, must be prepared. Further, there is a disadvantage that there are few n-type organic materials having good performance. The inventor of the present invention has disclosed a novel organic rectifying element material having a donor and an acceptor in one molecule in JP-A-5-259434, but cannot be used as a photoelectric conversion element because it does not absorb light in the visible region.
【0004】本発明者らは、新規なフェナジノン誘導体
ならびにその製造方法を提供することを目的とする。さ
らに、この材料を用いる光電変換素子を提供することを
目的とする。An object of the present invention is to provide a novel phenazinone derivative and a method for producing the same. Another object is to provide a photoelectric conversion element using this material.
【0005】[0005]
【課題を解決するための手段】本発明者らは、上記問題
を解決するため、可視光波長領域に吸収を有する一般式
(1)で示すフェナジノン誘導体を提供する。Means for Solving the Problems In order to solve the above problems, the present inventors provide a phenazinone derivative represented by the general formula (1) having absorption in a visible light wavelength region.
【0006】[0006]
【化3】 Embedded image
【0007】式1中Rは、置換基を含んでもよいアリー
ル基又はヘテロアリール基であるフェナジノン誘導体を
提供する。なお、前記アリール基又はヘテロアリール基
は、240nm以上の波長に吸収を有し、芳香族性をす
るものがよい。In the formula 1, R represents a phenazinone derivative which is an aryl group or a heteroaryl group which may contain a substituent. The aryl group or heteroaryl group preferably has absorption at a wavelength of 240 nm or more and has aromaticity.
【0008】また、可視光波長領域に吸収を有する一般
式(2)で示される10−ベンジル−2(10H)−フ
ェナジノン誘導体を提供する。Further, the present invention provides a 10-benzyl-2 (10H) -phenazinone derivative represented by the general formula (2) having an absorption in a visible light wavelength region.
【0009】[0009]
【化4】 Embedded image
【0010】式2中、置換基R1、R2、R3、R4、R5
はそれぞれ水素原子、ハロゲン原子、置換基を含んでも
よいアルキル基、アリール基、ヒドロキシ基、ヒドロキ
シアルキル基、ニトロ基、シアノ基、カルボシキ基、カ
ルボキシアルキル基、スルホン基、ホスホニル基、アミ
ノ基、アルキルアミノ基を表す。In the formula 2, the substituents R 1 , R 2 , R 3 , R 4 , R 5
Is a hydrogen atom, a halogen atom, an alkyl group which may contain a substituent, an aryl group, a hydroxy group, a hydroxyalkyl group, a nitro group, a cyano group, a carboxy group, a carboxyalkyl group, a sulfone group, a phosphonyl group, an amino group, an alkyl group. Represents an amino group.
【0011】また、上記置換基は少なくとも1つが電子
吸引性置換基であることを特徴とする10−ベンジル−
2(10H)−フェナジノン誘導体である。Further, at least one of the substituents is an electron-withdrawing substituent.
2 (10H) -phenazinone derivative.
【0012】さらに、上記で示されるフェナジノン誘導
体を用いることを特徴とする光電変換素子を見出した。
また、フェナジノン誘導体層と高分子導電体材料層また
は金属系材料層とが積層されていることを特徴とする。Further, a photoelectric conversion element characterized by using the phenazinone derivative shown above has been found.
Further, a phenazinone derivative layer and a polymer conductive material layer or a metal-based material layer are stacked.
【0013】[0013]
【発明の実施の形態】本発明の10−ベンジル−2(1
0H)−フェナジノン誘導体およびその製造方法につい
て、さらに詳細に説明する。ここで、上記一般式(1)
で示される各種置換基は以下のとおりである。DETAILED DESCRIPTION OF THE INVENTION 10-benzyl-2 (1
The 0H) -phenazinone derivative and a method for producing the same will be described in more detail. Here, the above general formula (1)
The various substituents represented by are as follows.
【0014】置換基R1、R2、R3、R4、R5におい
て、ハロゲン原子としてはフッ素、塩素、臭素、ヨウ素
などがあげられる。また、置換基を含んでもよいアルキ
ル基として直鎖状、分枝状または環状のいずれのタイプ
のものであってもよく、例えば、メチル、エチル、n−
プロピル、イソプロピル、t−ブチル、n−ペンチル、
イソペンチル、ネオペンチル、n−ヘキチル、イソヘキ
チル、シクロヘキシル、クロロメチル、クロロエチル基
などがあげられる。In the substituents R 1 , R 2 , R 3 , R 4 and R 5 , examples of the halogen atom include fluorine, chlorine, bromine and iodine. Further, the alkyl group which may contain a substituent may be of any type of linear, branched or cyclic, such as methyl, ethyl, n-
Propyl, isopropyl, t-butyl, n-pentyl,
Examples include isopentyl, neopentyl, n-hexyl, isohexyl, cyclohexyl, chloromethyl, and chloroethyl groups.
【0015】置換基を含んでもよいアリール基として
は、例えば、フェニル、トリル、キシリル、エチルフェ
ニル、ジエチルフェニル、クメニル、メシチル、ナフチ
ル、インデニル、アントリル基などがあげられる。The aryl group which may contain a substituent includes, for example, phenyl, tolyl, xylyl, ethylphenyl, diethylphenyl, cumenyl, mesityl, naphthyl, indenyl, anthryl and the like.
【0016】ヒドロキシアルキル基としては、例えば、
メトキシ、エトキシ、ブトキシ基などがあげられる。As the hydroxyalkyl group, for example,
Examples include methoxy, ethoxy, and butoxy groups.
【0017】カルボキシアルキル基としては、例えば、
カルボキシメチル、カルボシキシエチル、カルボシキシ
プロビル、カルボシキシブチル、カルボシキシフェニル
基などがあげられる。As the carboxyalkyl group, for example,
Examples include carboxymethyl, carboxyethyl, carboxypropyl, carboxybutyl, and carboxyphenyl groups.
【0018】アルキルアミン基としては、例えば、メチ
ルアミン、エチルアミノ、n−プロビルアミノ、イソプ
ロビルアミノ、n−ブチルアミノ、n−ペンチルアミ
ノ、フェニルアミン、ジメチルアミン、ジエチルアミ
ノ、ジプロビルアミノ、ジブチルアミノ、ジペンチルア
ミノ、ジフェニルアミン基などがあげられる。Examples of the alkylamine group include methylamine, ethylamino, n-propylamino, isopropylamino, n-butylamino, n-pentylamino, phenylamine, dimethylamine, diethylamino, dipropylamino, dibutyl Amino, dipentylamino, diphenylamine groups and the like.
【0019】光電変換特性を向上するには電荷を効率よ
くに分離しなければいけない。そのため、置換基R1、
R2、R3、R4、R5としては、電子吸引性置換基が好ま
しい。電子吸引性基としてはフッ素、塩素、臭素、ヨウ
素、ニトロ基、シアノ基、カルボシキル基、カルボキシ
アルキル基などがあげられる。In order to improve the photoelectric conversion characteristics, charges must be efficiently separated. Therefore, the substituent R 1 ,
As R 2 , R 3 , R 4 and R 5 , an electron-withdrawing substituent is preferable. Examples of the electron-withdrawing group include fluorine, chlorine, bromine, iodine, a nitro group, a cyano group, a carboxy group, and a carboxyalkyl group.
【0020】本発明において、10−ベンジル−2(1
0H)−フェナジノン誘導体は5-メチル-10-ベンジル-5,
10-ジヒドロフェナジン誘導体から、酸化的脱アルキル
化反応によって製造される。その詳細な反応過程は下記
のとおりである。In the present invention, 10-benzyl-2 (1
0H) -phenazinone derivative is 5-methyl-10-benzyl-5,
Produced from 10-dihydrophenazine derivatives by oxidative dealkylation. The detailed reaction process is as follows.
【0021】5-メチル-10-ベンジル-5,10-ジヒドロフェ
ナジン誘導体をジメチルスルホキシド(DMSO)中で47%
臭化水素酸で酸化したのち、水酸化ナトリウム水溶液で
処理し、これをトルエンで抽出、カラムクロマトグラフ
ィーで精製して得られた紫色固体を酢酸エチルから再結
晶することによって10-ベンジル-2(10H)-フェナジノン
誘導体を得た。The 5-methyl-10-benzyl-5,10-dihydrophenazine derivative was converted to 47% in dimethyl sulfoxide (DMSO).
After oxidation with hydrobromic acid, the mixture was treated with an aqueous sodium hydroxide solution, extracted with toluene, purified by column chromatography, and the resulting purple solid was recrystallized from ethyl acetate to give 10-benzyl-2 ( 10H) -phenazinone derivative was obtained.
【0022】10−ベンジル−2(10H)−フェナジ
ノン誘導体膜(以下、フェナジノン膜と略称する)と高
分子導電体材料層または金属系材料層とが積層されてい
る構成部分を有する素子が優れた光電変換作用を有する
ことを明らかにした。ここにいう高分子導電体材料層は
有機合成系材料、有機熱分解系材料および炭素系材料よ
りなる群から選ばれた少なくとも一つの高分子導電体材
料からなる層であり、また金属系材料層は金属、合金、
金属酸化物、金属硫化物および合金酸化物よりなる群か
ら選ばれた少なくとも一つの金属系材料からなる層であ
る。An element having a component in which a 10-benzyl-2 (10H) -phenazinone derivative film (hereinafter abbreviated as a phenazinone film) and a polymer conductive material layer or a metal material layer is laminated is excellent. It has been revealed that it has a photoelectric conversion effect. The polymer conductive material layer referred to herein is a layer made of at least one polymer conductive material selected from the group consisting of an organic synthetic material, an organic pyrolysis material, and a carbon material, and a metal material layer. Is metal, alloy,
It is a layer made of at least one metal-based material selected from the group consisting of metal oxides, metal sulfides, and alloy oxides.
【0023】本フェナジノン膜は上記した化合物であれ
ば単独でも2種以上の混合物でもよい。これらのフェナ
ジンが膜とされた場合の長期安定化のために若干量の酸
化防止剤、耐紫外線安定剤、膜厚制御材としてのスペー
サー粉末(プラスチックス粉末、シリカ粉末、シリコー
ンゴム粉末等)を加えてもよく、また膜の厚さの確認材
として色素(着色料、蛍光料)を少量含有させてもよ
い。The phenazinone film may be a single compound or a mixture of two or more of the above compounds. For long-term stabilization when these phenazines are formed into a film, a small amount of an antioxidant, an ultraviolet light stabilizer, and a spacer powder (plastics powder, silica powder, silicone rubber powder, etc.) as a film thickness controlling material are used. It may be added, or a small amount of a dye (colorant, fluorescent material) may be contained as a material for checking the thickness of the film.
【0024】高分子導電体材料のうち有機合成系材料と
しては、ポリピロール、ポリ-3-メチルピロール、ポリ-
3,4-ジメチルピロール、ポリチオフェン、ポリ-3-メチ
ルチオフェン、ポリ-3,4-ジメチルチオフェン、ポリ-p-
フェニン、ポリアセチレン、ポリ-p-フェニレンスルフ
ィド、ポリ-m-フェニレン、ポリ-p-フェニレンオキシ
ド、ポリシアノアセチレン、ポリフェニルアセチレン、
ポリビニルカルバゾール、ポリジアセチレン、ポリピリ
ジン、ポリ(N-メチルピロール)、ポリピコリン等があ
り、これらは未ドーピング物、ドーピング物のいずれで
も使用することができ、またこれらを含む導電性のゴム
や樹脂も使用できる。Among the polymer conductive materials, organic synthetic materials include polypyrrole, poly-3-methylpyrrole, and poly-pyrrole.
3,4-dimethylpyrrole, polythiophene, poly-3-methyl
Luthiophene, poly-3,4-dimethylthiophene, poly-p-
Phenin, polyacetylene, poly-p-phenylene sulfide, poly-m-phenylene, poly-p-phenylene oxide, polycyanoacetylene, polyphenylacetylene,
There are polyvinyl carbazole, polydiacetylene, polypyridine, poly (N-methylpyrrole), polypicoline, etc., which can be used either undoped or doped, and also use conductive rubber or resin containing these. it can.
【0025】高分子導電体材料のうち有機熱分解系材料
としては、合成グラファイト、導電性炭素繊維、熱分解
ポリイミド、熱分解ポリオキサジアゾール、熱分解ポリ
オレフィン、熱分解ポリアミド、熱分解ポリアクリロニ
トリル、熱分解ポリ塩化ビニル、熱分解ポリビニルアル
コール、熱分解エポキシ樹脂、熱分解フェノール樹脂、
熱分解架橋ポリスチレン、熱分解ポリイソシアヌレート
および熱分解ポリペプチド等があり、これらは未ドーピ
ング物、ドーピング物のいずれでも使用することがで
き、またこれらを含む導電性のゴムや樹脂も使用でき
る。Among the polymer conductive materials, organic pyrolytic materials include synthetic graphite, conductive carbon fiber, pyrolytic polyimide, pyrolytic polyoxadiazole, pyrolytic polyolefin, pyrolytic polyamide, pyrolytic polyacrylonitrile, and the like. Pyrolytic polyvinyl chloride, pyrolytic polyvinyl alcohol, pyrolytic epoxy resin, pyrolytic phenolic resin,
There are pyrolytic cross-linked polystyrene, pyrolytic polyisocyanurate, pyrolytic polypeptide, and the like. These can be used as either undoped or doped substances, and conductive rubbers and resins containing these can also be used.
【0026】高分子導電体材料のうち炭素系材料として
は、グラファイト、グラスカーボン、ファーネスブラッ
ク、ケッチェンブラック、アセチレンブラック、石油ピ
ッチ炭化物およびコールタールピッチ炭化物等があり、
これらは未ドーピング物、ドーピング物のいずれでも使
用することができ、またこれらを含む導電性のゴムや樹
脂も使用できる。Among the polymer conductive materials, examples of carbon-based materials include graphite, glass carbon, furnace black, Ketjen black, acetylene black, petroleum pitch carbide, and coal tar pitch carbide.
These can be used either as undoped or doped materials, and can also be used conductive rubbers and resins containing these.
【0027】金属系材料としては、金属(たとえば金、
銀、白金、パラジウム、ニッケル、アルミニウム、イン
ジウム、マグネシウム、カルシウム、ケイ素、チタニウ
ム、ジルコニウム等)、合金(たとえばパラジウム合
金、アルミニウム合金、チタニウム合金、マグネシウム
合金、スズ合金、インジウム合金、アンチモン合金)、
金属酸化物(たとえば酸化アルミニウム、酸化インジウ
ム、酸化ケイ素、酸化チタニウム、酸化スズ、酸化亜
鉛、酸化銅、酸化アンチモン、酸化ジルコニウム等でド
ーパントにより格子欠陥を作って導電性を付与したも
の)、金属硫化物(たとえば硫化鉄、硫化コバルト、硫
化ニッケル、硫化銅等で格子欠陥を作って導電性を付与
したもの)、合金酸化物(上記合金の酸化物あるいは上
金属酸化物の混合物)等があり、またこれらを含む導電
性のゴムや樹脂も使用できる。As the metal-based material, a metal (for example, gold,
Silver, platinum, palladium, nickel, aluminum, indium, magnesium, calcium, silicon, titanium, zirconium, etc.), alloys (eg, palladium alloy, aluminum alloy, titanium alloy, magnesium alloy, tin alloy, indium alloy, antimony alloy),
Metal oxides (eg, aluminum oxide, indium oxide, silicon oxide, titanium oxide, tin oxide, suboxide
Lead, copper oxide, antimony oxide, zirconium oxide, etc. are used to create lattice defects with dopants to give conductivity, and metal sulfides (eg, iron sulfide, cobalt sulfide, nickel sulfide, copper sulfide, etc. Conductive oxides), alloy oxides (oxides of the above alloys or mixtures of upper metal oxides) and the like, and conductive rubbers and resins containing these can also be used.
【0028】本発明にいうフェナジノン膜は高分子導電
体材料層と高分子導電体材料層の間に、または高分子導
電体材料層と金属系材料層の間に、あるいは金属系材料
層と金属系材料層の間に設けられる。その最も簡単なも
のはこのいずれかの組み合わせの一積層でよいが、さら
に効果を強化するためには、たとえば、高分子導電体材
料層、フェナジノン膜、高分子導電体材料層、フェナジ
ノン膜、金属系材料層等という具合に複層または多層構
造にするのが好ましい。この場合、高分子導電体材料層
と金属系材料層とは適宣入れ替えて構成してもよいのは
勿論である。The phenazinone film referred to in the present invention is formed between a polymer conductive material layer and a polymer conductive material layer, between a polymer conductive material layer and a metal-based material layer, or between a metal-based material layer and a metal-based material layer. It is provided between the system material layers. The simplest one may be a single layer of any of these combinations, but in order to further enhance the effect, for example, a polymer conductor material layer, a phenazinone film, a polymer conductor material layer, a phenazinone film, a metal It is preferable to form a multi-layer or multi-layer structure such as a system material layer. In this case, the polymer conductive material layer and the metal-based material layer may be replaced with each other.
【0029】以上の積層物は、通常基板(ガラス、プラ
スチックス、フィルム、金属シート、セラミック板、プ
ラスチックス成型品等)の上に設けられ適当な電極部分
が付けられた後、さらに要すればフィルムで被覆される
ことになるが、目的によっては基板同士の間に積層され
てもよい。したがって、この積層物の厚さは基板の厚
さ、高分子導電体材料層の厚さあるいは金属系材料層の
厚さによって任意に変わりうる。しかしながら、フェナ
ジノン膜については単層で200〜5000Åの厚さにするの
がよい。したがって、フェナジノン膜が積層される場合
はその積層回数に応じて合計厚さは増加することになる
が、各フェナジノン膜の厚さを200〜5000Åの範囲内で
各膜の厚さを薄くし、200〜2000Å程度になるように留
意するのが好ましい。なお膜厚は均一になるよう作業に
注意すべきである。The above-mentioned laminate is usually provided on a substrate (glass, plastics, film, metal sheet, ceramic plate, plastics molded product, etc.) and provided with an appropriate electrode portion. Although it will be covered with a film, it may be laminated between substrates depending on the purpose. Therefore, the thickness of the laminate can be arbitrarily changed depending on the thickness of the substrate, the thickness of the polymer conductive material layer, or the thickness of the metal-based material layer. However, the phenazinone film is preferably a single layer having a thickness of 200 to 5000 °. Therefore, when a phenazinone film is laminated, the total thickness will increase according to the number of times of lamination, but the thickness of each film is reduced within the range of 200 to 5000 mm for each phenazinone film, It is preferable to pay attention to be about 200 to 2000 °. Care should be taken in the work to make the film thickness uniform.
【0030】本発明のフェナジノン膜を形成させる方法
としては、次のいずれかの方法が採用される。As a method for forming the phenazinone film of the present invention, any one of the following methods is employed.
【0031】(1)真空蒸着法またはスパッタリング法 (2)溶液を塗装(キャスト法を含む)して乾燥する方法 (3)あらかじめ膜化したものを載置(加圧法、接着法、
静電貼付法)する方法。(1) Vacuum evaporation method or sputtering method (2) Method of applying a solution (including a casting method) and drying it (3) Place a film formed in advance (pressing method, bonding method,
Electrostatic sticking method).
【0032】フェナジノン膜は積層面の全面に形成され
るばかりではなく、目的に応じて予定された形にパター
ン化してもよく、また部分的に不要部分をエッチング除
去してパターン化してもよい。The phenazinone film is not only formed on the entire surface of the laminated surface, but may be patterned in a predetermined shape according to the purpose, or may be formed by partially removing unnecessary portions by etching.
【0033】本発明による有機光電変換素子の構造の基
本的な一例について説明する。図1に示すように、有機
整流素子は、基板1と、基板1上に形成された電極2
と、電極2上に形成された高分子導電体層3と、高分子
導電体層3上に形成されたフェナジノン膜4と、フェナ
ジノン膜4上に形成された電極5とによって構成されて
いる。A basic example of the structure of the organic photoelectric conversion device according to the present invention will be described. As shown in FIG. 1, an organic rectifying element includes a substrate 1 and electrodes 2 formed on the substrate 1.
And a polymer conductor layer 3 formed on the electrode 2, a phenazinone film 4 formed on the polymer conductor layer 3, and an electrode 5 formed on the phenazinone film 4.
【0034】基板1上に設けられる電極2は、実質的に
基板1の全面を覆った透明電極にするのがよい。透明電
極は、ガラス板、透明プラスチックシートまたはフィル
ムなどの基板1の上に、金、銀、アルミニウム、インジ
ウム、酸化インジウムスズ(ITO膜)、酸化スズ(ネサ
膜)を蒸着することによって形成 することができる。
また、電極5は、金、銀、銅、アルミニウムまたはニッ
ケルを蒸着することによって形成することができる。な
お、特に単層型として用いる場合は、高分子導電体層3
を省略することができる。The electrode 2 provided on the substrate 1 is preferably a transparent electrode covering substantially the entire surface of the substrate 1. The transparent electrode is formed by depositing gold, silver, aluminum, indium, indium tin oxide (ITO film), and tin oxide (nesa film) on a substrate 1 such as a glass plate, a transparent plastic sheet or a film. Can be.
The electrode 5 can be formed by depositing gold, silver, copper, aluminum, or nickel. In particular, when used as a single layer type, the polymer conductive layer 3
Can be omitted.
【0035】有機光電変換素子の製作手順は、基板1上
に形成される電極2の種類によって異なるが、アルミニ
ウムを一方の電極として用いる場合には、まず、アルミ
ニウム電極上に本発明のフェナジン膜を真空蒸着法、塗
布法、キャスト法、スピンコート法等の方法で作り、そ
の上に高分子導電体層を積層するのが好ましい。そして
必要に応じて、さらにその上に金電極等の対極を真空蒸
着すればよい。The manufacturing procedure of the organic photoelectric conversion element differs depending on the type of the electrode 2 formed on the substrate 1. When aluminum is used as one of the electrodes, first, the phenazine film of the present invention is formed on the aluminum electrode. It is preferable that the polymer conductive layer is formed by a method such as a vacuum evaporation method, a coating method, a casting method, and a spin coating method, and a polymer conductor layer is laminated thereon. If necessary, a counter electrode such as a gold electrode may be further vacuum-deposited thereon.
【0036】一方、スッパタリング法等で形成された透
明電極、たとえば金電極を有する基板を用いる場合に
は、金電極上に高分子導電体層を電解酸化重合法等で積
層し電機化学的に脱ドーピング処理をした後、その上に
フェナジノン膜を真空蒸着等で積層するのが便利であ
る。さらに、必要に応じてアルミニウム等の電極を真空
蒸着すればよいのである。On the other hand, when a transparent electrode formed by a sputtering method or the like, for example, a substrate having a gold electrode is used, a polymer conductor layer is laminated on the gold electrode by an electrolytic oxidation polymerization method or the like, and electrochemically. After the undoping treatment, it is convenient to stack a phenazinone film thereon by vacuum evaporation or the like. Further, if necessary, an electrode of aluminum or the like may be vacuum-deposited.
【0037】本発明の有機光電変換素子では、高分子導
電体層とフェナジノン膜との界面において、ショットキ
ー型もしくはヘテロ接合型のバリヤーが形成され、自発
的に形成された電位勾配にしたがって順方向の電圧印加
によって電荷の注入と両層を横切る電荷の輸送が生ずる
が、逆方向の電圧印加では電位勾配に逆らうため電流は
流れず、ダイオードとして機能する。また、光照射によ
って界面において電荷の分離が生じ、電位勾配に沿って
電荷の輸送が生じる。したがって、有機光電変換素子の
両電極間に負荷をかけ外部で短絡することによって光電
流が得られる。さらに順方向の電圧印加によって注入さ
れた電荷がバルク中の反対電荷と再結合する際に発光す
ることを利用して、発光ダイオードとしても機能せしめ
ることができる。In the organic photoelectric conversion device of the present invention, a Schottky type or heterojunction type barrier is formed at the interface between the polymer conductive layer and the phenazinone film, and a forward direction is formed in accordance with a spontaneously formed potential gradient. Injection of charges and transport of charges across both layers occur due to the application of the voltage, but when a voltage is applied in the opposite direction, a current does not flow because the potential gradient is defeated, and the diode functions as a diode. In addition, charge separation occurs at the interface due to light irradiation, and charge transport occurs along a potential gradient. Therefore, a photocurrent can be obtained by applying a load between both electrodes of the organic photoelectric conversion element and short-circuiting outside. Further, by utilizing the fact that the charge injected by the forward voltage application is recombined with the opposite charge in the bulk, the device can function as a light emitting diode.
【0038】[0038]
【実施例】以下、本発明の10-ベンジル-2(10H)-フェナ
ジノン誘導体の合成法及びそれを用いた光電変換素子の
実施例について説明する。EXAMPLES Examples of the method for synthesizing the 10-benzyl-2 (10H) -phenazinone derivative of the present invention and examples of the photoelectric conversion device using the same will be described below.
【0039】〔実施例1〕10-ベンジル-2(10H)-フェナ
ジノンの合成法をa)〜b)に分けて説明する。Example 1 A method for synthesizing 10-benzyl-2 (10H) -phenazinone will be described by dividing it into a) and b).
【0040】a) 5-メチル-5,10-ジヒドロフェナジン
の合成 5-メチルフェナジニウムメチル硫酸塩3.082g(10.1mmol)
を99%エタノールに溶かした後、 Na2S2O4 20gを加え、
水を少量ずつ加えながら激しく振り、最後に氷を加え全
量を1000mlにし、放置した。得られた固体を即時減圧下
で乾燥する。5-メチル-5,10-ジヒドロフェナジンの白色
固体を1.879g(9.6mmol)、収率95%で得た。A) Synthesis of 5-methyl-5,10-dihydrophenazine 3.082 g (10.1 mmol) of 5-methylphenazinium methyl sulfate
Was dissolved in 99% ethanol, and Na 2 S 2 O 4 20 g was added.
Shake vigorously while adding water little by little, and finally add ice to make the total volume 1000 ml, and let stand. The solid obtained is immediately dried under reduced pressure. 1.879 g (9.6 mmol) of a white solid of 5-methyl-5,10-dihydrophenazine was obtained in a yield of 95%.
【0041】b) 5-メチル-10-ベンジル-5,10-ジヒド
ロフェナジンの合成 アルゴン雰囲気下、5-メチル-5,10-ジヒドロフェナジン
1.000g(5.12mmol)をDMEに溶かし、n-BuLi-hexane溶液3.
2ml(5.12mmol)をシリンジにより滴下した。次にベンジ
ルブロミド0.62ml(5.12mmol)をDMEに溶かしてシリンジ
によりゆっくりと滴下し、一昼夜撹拌した。反応溶液を
Na2S2O4飽和水溶液で処理した後、トルエンで抽出し、N
a2S2O4上で乾燥した。溶媒を減圧下で留去し、残さをカ
ラムクロマトグラフィー(充填剤:シリカゲル、溶媒:
トルエン:ヘキサン=1:1)で分離精製し、ヘキサン
から再結晶した。5-メチル-10-ベンジル5,10-ジヒドロ
フェナジンの淡緑色固体を0.547g(1.92mmol)、収率38%
で得た。B) Synthesis of 5-methyl-10-benzyl-5,10-dihydrophenazine Under an argon atmosphere, 5-methyl-5,10-dihydrophenazine
Dissolve 1.000g (5.12mmol) in DME, n-BuLi-hexane solution 3.
2 ml (5.12 mmol) was added dropwise via syringe. Next, 0.62 ml (5.12 mmol) of benzyl bromide was dissolved in DME, and the solution was slowly added dropwise with a syringe, followed by stirring overnight. Reaction solution
After treatment with a saturated aqueous solution of Na 2 S 2 O 4 , extraction with toluene
Dried over a 2 S 2 O 4 . The solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography (filler: silica gel, solvent:
Separation and purification were carried out using toluene: hexane = 1: 1), and the product was recrystallized from hexane. 0.547 g (1.92 mmol) of a pale green solid of 5-methyl-10-benzyl 5,10-dihydrophenazine, yield 38%
I got it.
【0042】5-メチル-10-ベンジル5,10-ジヒドロフェ
ナジンの物理データを下記に示す。mp. 122.0-124.0
℃,1H-NMR (C6D6) δ 2.44-2.55 (br, 3H), 4.38-4.4
7 (br,2H), 6.10-6.13 (m, 5H),6.46-6.69 (m, 3H), 6.
95-7.11 (m, 5H)。The physical data of 5-methyl-10-benzyl 5,10-dihydrophenazine are shown below. mp. 122.0-124.0
° C, 1H-NMR (C 6 D 6 ) δ 2.44-2.55 (br, 3H), 4.38-4.4
7 (br, 2H), 6.10-6.13 (m, 5H), 6.46-6.69 (m, 3H), 6.
95-7.11 (m, 5H).
【0043】5-メチル-10-ベンジル-5,10-ジヒドロフェ
ナジン0.298g(1.05mmol)を少量の蒸留DMSOに溶かし、47
%HBr酸0.72g(4.2mmol)を加え、90-110℃で2h撹拌した。
放冷後、混合物を多量の水に注ぎ、NaOH水溶液で処理し
た。これをトルエンで抽出した後、Na2S2O4上で乾燥し
た。溶媒をを減圧留去した後、残さをカラムクロマトグ
ラフィー(充填剤:シリカゲル、溶媒: 酢酸エチル)
で分離精製して、酢酸エチルから再結晶した。10-ベン
ジル-2(10H)-フェナジノンの紫色固体を0.075g(0.262mm
ol)、収率25%で得た。10-ベンジル-2(10H)-フェナジノ
ンの物理データを下記に示す。mp. 262.0-264.0℃,IR
(KBr) 1628 (C=O) cm-1,UV(MeOH) λmax / nm (logε)
514 (3.87),1H-NMR (CDCl3) δ 5.50 (s, 2H), 6.2
3-6.24 (s, 1H), 7.07-7.18 (m, 3H), 7.27-7.38 (m, 3
H), 7.44-7.50 (m, 2H), 7.61 7.69 (m, 2H), 8.05-8.0
8 (d, 1H) Anal. Calcd for C19H14N2O: C 79.70%, H 4.93%, N
9.78% Found: C 79.33%, H 4.88%, N 9.84%。Dissolve 0.298 g (1.05 mmol) of 5-methyl-10-benzyl-5,10-dihydrophenazine in a small amount of distilled DMSO and add
0.72 g (4.2 mmol) of% HBr acid was added, and the mixture was stirred at 90 to 110 ° C for 2 hours.
After cooling, the mixture was poured into a large amount of water and treated with an aqueous NaOH solution. After this was extracted with toluene, it was dried over Na 2 S 2 O 4 . After the solvent was distilled off under reduced pressure, the residue was subjected to column chromatography (filler: silica gel, solvent: ethyl acetate).
And recrystallized from ethyl acetate. 0.075 g (0.262 mm) of a purple solid of 10-benzyl-2 (10H) -phenazinone
ol) in a yield of 25%. Physical data of 10-benzyl-2 (10H) -phenazinone are shown below. mp. 262.0-264.0 ℃, IR
(KBr) 1628 (C = O) cm-1, UV (MeOH) λmax / nm (logε)
514 (3.87), 1H-NMR (CDCl 3 ) δ 5.50 (s, 2H), 6.2
3-6.24 (s, 1H), 7.07-7.18 (m, 3H), 7.27-7.38 (m, 3
H), 7.44-7.50 (m, 2H), 7.61 7.69 (m, 2H), 8.05-8.0
8 (d, 1H) Anal.Calcd for C19H14N2O: C 79.70%, H 4.93%, N
9.78% Found: C 79.33%, H 4.88%, N 9.84%.
【0044】〔実施例2〕10-(p-ニトロベンジル)-2(10
H)-フェナジノンの合成法を説明する。Example 2 10- (p-Nitrobenzyl) -2 (10
A method for synthesizing H) -phenazinone will be described.
【0045】5-メチル-10-(p-ニトロベンジル)-5,10-ジ
ヒドロフェナジン0.050g(0.151mmol)を少量の蒸留DMSO
に溶かし、47%HBr酸0.104g(0.604mmol)を加え、90-110
℃で2hした。放冷後、混合物を多量の水に注ぎ、NaOH水
溶液で処理した。これをトルエンで抽出した後、Na2S2O
4上で乾燥した。溶媒を減圧留去した後、残さをカラム
クロマトグラフィー(充填剤:シリカゲル、溶媒: CH2
Cl2 および 酢酸エチル)で分離精製して、得られた赤
色固体を酢酸エチルで再結晶し、10-(p-ニトロベンジ
ル)-2(10H)-フェナジノン0.014g(0.042mmol)、収率28%
で得た。0.050 g (0.151 mmol) of 5-methyl-10- (p-nitrobenzyl) -5,10-dihydrophenazine was added to a small amount of distilled DMSO
Was dissolved in 47% HBr acid 0.104 g (0.604 mmol) was added, 90-110
C. for 2 h. After cooling, the mixture was poured into a large amount of water and treated with an aqueous NaOH solution. After extracting this with toluene, Na 2 S 2 O
Dried on 4 . After the solvent was distilled off under reduced pressure, the residue was subjected to column chromatography (filler: silica gel, solvent: CH 2
Cl 2 and ethyl acetate), and the resulting red solid was recrystallized from ethyl acetate to give 10- (p-nitrobenzyl) -2 (10H) -phenazinone 0.014 g (0.042 mmol), yield 28. %
I got it.
【0046】10-(p-ニトロベンジル)-2(10H)-フェナジ
ノンの物理データを下記に示す。mp. 270.0-272.0℃ ,
IR(KBr) 1631 (C=O), 1519 (NO2), 1343 (NO2) cm-1UV
(MeOH) λmax / nm (logε) 514 (4.10),1H-NMR (CDC
l3) δ 5.62-5.64 (s,2H), 6.28-6.29 (s, 1H), 7.11-
7.16 (m, 1H),7.28-7.41 (m, 3H), 7.51-7.57(m,1H),
7.64-7.76 (m, 2H), 8.11-8.15 (m, 1H), 8.20-8.25
(d, 2H) Anal. Calcd for C19H13N3O3 : C 68.88%, H 3.95%, N
12.68% Found: C 68.83%, H 3.72%, N 12.78%。The physical data of 10- (p-nitrobenzyl) -2 (10H) -phenazinone are shown below. mp. 270.0-272.0 ℃,
IR (KBr) 1631 (C = O), 1519 (NO 2 ), 1343 (NO 2 ) cm -1 UV
(MeOH) λmax / nm (logε) 514 (4.10), 1H-NMR (CDC
l 3 ) δ 5.62-5.64 (s, 2H), 6.28-6.29 (s, 1H), 7.11-
7.16 (m, 1H), 7.28-7.41 (m, 3H), 7.51-7.57 (m, 1H),
7.64-7.76 (m, 2H), 8.11-8.15 (m, 1H), 8.20-8.25
(d, 2H) Anal.Calcd for C19H13N3O3: C 68.88%, H 3.95%, N
12.68% Found: C 68.83%, H 3.72%, N 12.78%.
【0047】〔実施例3〕ガラス基板1上に金電極2を
スパッタ法等により形成させ、その上に電解酸化重合に
よってポリ-3-メチルチオフェン層を積層させる。次い
で電機化学的に脱ドーピング処理して高分子導電体層3
とし、10-(p-ニトロベンジル)-2(10H)-フェナジノン4
を真空蒸着法により積層し、その上にアルミニウムを真
空蒸着して電極5を形成させ、有機光電変換素子を作成
した。Embodiment 3 A gold electrode 2 is formed on a glass substrate 1 by a sputtering method or the like, and a poly-3-methylthiophene layer is laminated thereon by electrolytic oxidation polymerization. Next, the polymer conductor layer 3 is subjected to electrochemical dedoping treatment.
And 10- (p-nitrobenzyl) -2 (10H) -phenazinone 4
Were laminated by a vacuum vapor deposition method, and aluminum was vacuum-deposited thereon to form an electrode 5, thereby producing an organic photoelectric conversion element.
【0048】この有機光電変換素子に10mW/cm2
の強度の光を照射したところ、短絡光電流0.12mA
/cm2、開回路光起電圧630mV、フィルファクタ
ー0.56で、変換効率は0.42%であった。The organic photoelectric conversion device was provided with 10 mW / cm 2
Irradiating light with a short-circuit intensity of 0.12 mA
/ Cm 2 , open circuit photovoltaic voltage 630 mV, fill factor 0.56, and conversion efficiency was 0.42%.
【0049】〔実施例4〕ガラス基板上にITO電極を
スパッタ法等により形成させ、その上10-(p-ニトロベン
ジル)-2(10H)-フェナジノンを真空蒸着法により製膜
し、その上にアルミニウムを真空蒸着して電極を形成さ
せ、有機光電変換素子を作成した。Example 4 An ITO electrode was formed on a glass substrate by sputtering or the like, and 10- (p-nitrobenzyl) -2 (10H) -phenazinone was formed thereon by vacuum evaporation. Then, aluminum was vacuum-deposited to form an electrode, thereby producing an organic photoelectric conversion element.
【0050】この有機光電変換素子に10mW/cm2
の強度の光を照射したところ、短絡光電流0.09mA
/cm2、開回路光起電圧620mV、フィルファクタ
ー0.49で、変換効率は0.28%であった。The organic photoelectric conversion device was provided with 10 mW / cm 2
Irradiation of light with a short-circuit photocurrent of 0.09 mA
/ Cm 2 , open circuit photovoltaic voltage 620 mV, fill factor 0.49, and conversion efficiency was 0.28%.
【0051】[0051]
【発明の効果】本発明は、新規なフェナジノン誘導体お
よびその製造方法を提供する。これらのフェナジノン誘
導体は可視光領域に吸収を有するため、優れた有機光電
変換素子用材料として有効である。The present invention provides a novel phenazinone derivative and a method for producing the same. Since these phenazinone derivatives have absorption in the visible light region, they are effective as excellent materials for organic photoelectric conversion elements.
【0052】特に、ベンジル基に電子吸引性置換基を導
入されている場合、分子内にドナーとアクセプターを有
するため、光によって励起された電荷を効率よく分離
し、分離した電子と正孔を効率よくお互い反対方向に輸
送され光電変換素子として機能する。さらに、電圧印加
によって注入された電荷がバリヤーの電位勾配に沿って
バルク中を移動する間に反対電荷と再結合して発光する
ことを利用して、電界発光素子としても機能する。In particular, when an electron-withdrawing substituent is introduced into the benzyl group, since the molecule has a donor and an acceptor, the charge excited by light can be efficiently separated, and the separated electrons and holes can be efficiently separated. They are often transported in opposite directions and function as photoelectric conversion elements. Further, it also functions as an electroluminescent element by utilizing the fact that charges injected by applying a voltage recombine with opposite charges while moving in the bulk along the potential gradient of the barrier and emit light.
【図1】本発明の光電変換素子を示す断面図である。FIG. 1 is a sectional view showing a photoelectric conversion element of the present invention.
1 基板 2 電極 3 高分子導電体層 4 フェナジノン膜 5 電極 DESCRIPTION OF SYMBOLS 1 Substrate 2 Electrode 3 Polymer conductor layer 4 Phenazinone film 5 Electrode
Claims (5)
であって、 【化1】 式1中Rは、置換基を含んでもよいアリール基又はヘテ
ロアリール基であることを特徴とするフェナジノン誘導
体。1. A phenazinone derivative represented by the general formula (1): In the formula 1, R is an aryl group or a heteroaryl group which may contain a substituent, wherein the phenazinone derivative is characterized in that:
(10H)−フェナジノン誘導体であって、 【化2】 式2中、置換基R1、R2、R3、R4、R5はそれぞれ水
素原子、ハロゲン原子、置換基を含んでもよいアルキル
基およびアリール基、ヒドロキシ基、ヒドロキシアルキ
ル基、ニトロ基、シアノ基、カルボシキ基、カルボキシ
アルキル基、スルホン基、ホスホニル基、アミノ基、ア
ルキルアミノ基を表すことを特徴とするフェナジノン誘
導体。2. 10-benzyl-2 represented by the general formula (2)
(10H) -phenazinone derivatives, In the formula 2, the substituents R 1 , R 2 , R 3 , R 4 , and R 5 are each a hydrogen atom, a halogen atom, an alkyl group and an aryl group which may contain a substituent, a hydroxy group, a hydroxyalkyl group, a nitro group, A phenazinone derivative, which represents a cyano group, a carboxy group, a carboxyalkyl group, a sulfone group, a phosphonyl group, an amino group, or an alkylamino group.
なくとも1つが電子吸引性置換基であることを特徴とす
る請求項2記載のフェナジノン誘導体。3. The phenazinone derivative according to claim 2, wherein at least one of the substituents R 1 , R 2 , R 3 , R 4 and R 5 is an electron-withdrawing substituent.
ナジノン誘導体を用いることを特徴とする光電変換素
子。4. A photoelectric conversion element comprising the phenazinone derivative according to claim 1.
ナジノン誘導体層と、高分子導電体材料層または金属系
材料層とが積層されていることを特徴とする請求項4記
載の光電変換素子。5. The photoelectric conversion according to claim 4, wherein the phenazinone derivative layer according to claim 1 and a polymer conductive material layer or a metal-based material layer are laminated. element.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8007598A JPH11284250A (en) | 1998-03-27 | 1998-03-27 | Phenazinone derivative and photoelectric transducer using the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8007598A JPH11284250A (en) | 1998-03-27 | 1998-03-27 | Phenazinone derivative and photoelectric transducer using the same |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH11284250A true JPH11284250A (en) | 1999-10-15 |
Family
ID=13708103
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8007598A Pending JPH11284250A (en) | 1998-03-27 | 1998-03-27 | Phenazinone derivative and photoelectric transducer using the same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH11284250A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003075364A1 (en) * | 2002-03-07 | 2003-09-12 | Nippon Oil Corporation | Photoelectric converting device |
WO2003077323A1 (en) * | 2002-03-11 | 2003-09-18 | Nippon Oil Corporation | Photoelectric converting device |
WO2006103863A1 (en) * | 2005-03-25 | 2006-10-05 | Japan Science And Technology Agency | Multifunction organic diode and matrix panel thereof |
-
1998
- 1998-03-27 JP JP8007598A patent/JPH11284250A/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003075364A1 (en) * | 2002-03-07 | 2003-09-12 | Nippon Oil Corporation | Photoelectric converting device |
JPWO2003075364A1 (en) * | 2002-03-07 | 2005-06-30 | 新日本石油株式会社 | Photoelectric conversion element |
WO2003077323A1 (en) * | 2002-03-11 | 2003-09-18 | Nippon Oil Corporation | Photoelectric converting device |
WO2006103863A1 (en) * | 2005-03-25 | 2006-10-05 | Japan Science And Technology Agency | Multifunction organic diode and matrix panel thereof |
US7893429B2 (en) | 2005-03-25 | 2011-02-22 | National University Corporation University Of Toyama | Multifunction organic diode and matrix panel thereof |
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