JPH04360150A - Germanium phthalocyanine type photoelectric converting agent - Google Patents
Germanium phthalocyanine type photoelectric converting agentInfo
- Publication number
- JPH04360150A JPH04360150A JP3163557A JP16355791A JPH04360150A JP H04360150 A JPH04360150 A JP H04360150A JP 3163557 A JP3163557 A JP 3163557A JP 16355791 A JP16355791 A JP 16355791A JP H04360150 A JPH04360150 A JP H04360150A
- Authority
- JP
- Japan
- Prior art keywords
- converting agent
- photoelectric converting
- photoelectric conversion
- germanium
- phthalocyanine
- 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.)
- Granted
Links
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims description 16
- 229910052732 germanium Inorganic materials 0.000 title abstract description 7
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 title description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- -1 germanium phthalocyanine derivative Chemical class 0.000 abstract description 7
- 239000002184 metal Substances 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 5
- 230000003287 optical effect Effects 0.000 abstract description 3
- 230000008022 sublimation Effects 0.000 abstract 1
- 238000000859 sublimation Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMOKYSFFKRRWKD-UHFFFAOYSA-N O[Ge]O Chemical compound O[Ge]O YMOKYSFFKRRWKD-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- OXTURSYJKMYFLT-UHFFFAOYSA-N dichlorogermane Chemical compound Cl[GeH2]Cl OXTURSYJKMYFLT-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- SEMIDUTZXZKVAS-UHFFFAOYSA-N 4-(dibenzylamino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 SEMIDUTZXZKVAS-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- 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
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は光電変換用材料として有
用な新規な光電変換剤に関し、特に置換基を有してもよ
い２個のフェノキシ基が中心金属に結合したジフェノキ
シゲルマニウムフタロシアニン誘導体からなる光電変換
剤に関する。本発明に係わる光電変換剤は、物質の光電
変換作用を本質的に利用する光電変換素子、例えば太陽
電池、光センサー、光スイッチング素子、電子写真感光
体等における光活性物質として有効に利用できるもので
ある。[Industrial Application Field] The present invention relates to a novel photoelectric conversion agent useful as a photoelectric conversion material, and particularly to a diphenoxygermanium phthalocyanine derivative in which two phenoxy groups, which may have substituents, are bonded to a central metal. The present invention relates to a photoelectric conversion agent. The photoelectric conversion agent according to the present invention can be effectively used as a photoactive substance in photoelectric conversion elements that essentially utilize the photoelectric conversion action of substances, such as solar cells, optical sensors, optical switching elements, electrophotographic photoreceptors, etc. It is.
【０００２】0002
【従来の技術】光電変換用材料、すなわち光電変換剤と
して数多くの物質が知られている。中でも可視光ないし
はその周辺波長域に感光性を示すものとして、Ｓｅ、Ｓ
ｅ／Ｔｅ、Ｓｅ／Ａｓ、ＣｄＳ、Ｓｉ等の無機化合物が
ある。これら無機化合物の多くは可撓性が無く、従って
加工性に難があり、かつ毒性が強いことが多い。その上
、高価に過ぎ、実用材料として多くの問題を抱えている
。2. Description of the Related Art Many substances are known as photoelectric conversion materials, that is, photoelectric conversion agents. Among them, Se and S exhibit photosensitivity to visible light or its surrounding wavelength range.
There are inorganic compounds such as e/Te, Se/As, CdS, and Si. Many of these inorganic compounds are not flexible, therefore have difficulty in processability, and are often highly toxic. Moreover, it is too expensive and has many problems as a practical material.
【０００３】一方、光電変換に有効な有機化合物として
は、メロシアニン類、フタロシアニン類、ビスあるいは
トリスアゾのごときポリアゾ化合物、キナクリドン化合
物、ペリレンテトラカルボン酸ジイミド化合物、ビス（
イミダゾピリドノ）ペリレン化合物等の有機染・顔料類
が知られており、上記無機化合物の問題点を克服する目
的で各方面で検討されて来ている。On the other hand, organic compounds effective for photoelectric conversion include merocyanines, phthalocyanines, polyazo compounds such as bis or trisazo, quinacridone compounds, perylenetetracarboxylic acid diimide compounds, bis(
Organic dyes and pigments such as imidazopyridono)perylene compounds are known and have been studied in various fields to overcome the problems of the above-mentioned inorganic compounds.
【０００４】特に、フタロシアニン類は安定で堅牢な有
機金属錯体型顔料として著名であり、金属の種類を選択
することにより、異なった物性が得られるので興味深い
。その一つとしてゲルマニウムフタロシアニン、正確に
はジクロロゲルマニウムフタロシアニンが知られている
が、このものは加水分解を受けやすく、ジヒドロキシゲ
ルマニウムフタロシアニンへ変化しやすい。このジヒド
ロキシゲルマニウムフタロシアニンは、加熱により容易
に脱水・重合して高分子量のポリゲルマニウムフタロシ
アニンに変化してしまうので、昇華・精製が不可能であ
る。このようにゲルマニウムフタロシアニンは、有用な
光電変換用材料として期待されながら、その化学的不安
定性と精製困難の故に、実用性のある材料として用いら
れることはなかった。In particular, phthalocyanines are famous as stable and robust organometallic complex type pigments, and are interesting because different physical properties can be obtained by selecting the type of metal. Germanium phthalocyanine, more precisely dichlorogermanium phthalocyanine, is known as one of these, but this substance is easily hydrolyzed and easily converted to dihydroxygermanium phthalocyanine. This dihydroxygermanium phthalocyanine is easily dehydrated and polymerized by heating and converted into high molecular weight polygermanium phthalocyanine, so it is impossible to sublimate and purify it. Thus, although germanium phthalocyanine is expected to be a useful photoelectric conversion material, it has never been used as a practical material due to its chemical instability and difficulty in purification.
【０００５】[0005]
【発明が解決しようとする課題】本発明の目的は、化学
的に安定であり、かつ昇華・精製の容易な、しかも極め
て顕著な光電変換作用を示す（すなわち、実用性のある
）ゲルマニウムフタロシアニン系有機光電変換剤を初め
て提供することである。[Problems to be Solved by the Invention] The object of the present invention is to provide a germanium phthalocyanine system that is chemically stable, easy to sublimate and purify, and exhibits an extremely remarkable photoelectric conversion effect (that is, has practical use). This is the first time to provide an organic photoelectric conversion agent.
【０００６】[0006]
【課題を解決するための手段】本発明の課題は、化１の
式で表される、置換基を有してもよい２個のフェノキシ
基が中心金属に結合したジフェノキシゲルマニウムフタ
ロシアニン誘導体からなるゲルマニウムフタロシアニン
系化合物を、有機光電変換剤として新規に採用すること
によって解決された。化１において、Ｒは水素、アルキ
ル、アラルキル、アリールおよびハロゲンから選ばれる
基を表し、ｎは５以下の正の整数を表す。[Means for Solving the Problems] The object of the present invention is to provide a diphenoxygermanium phthalocyanine derivative represented by the formula 1, in which two phenoxy groups, which may have substituents, are bonded to a central metal. This problem was solved by newly employing germanium phthalocyanine compounds as organic photoelectric conversion agents. In Chemical Formula 1, R represents a group selected from hydrogen, alkyl, aralkyl, aryl, and halogen, and n represents a positive integer of 5 or less.
【０００７】本発明において光電変換剤として用いられ
る、置換基を有してもよい２個のフェノキシ基が中心金
属に結合したジフェノキシゲルマニウムフタロシアニン
誘導体化合物のうちの幾つかは、文献（Ｒ．Ｄ．ジョイ
ナー等、米国化学会誌、第８２巻、５７９０〜５７９１
頁、１９６０年刊）に記載されているが、光電変換剤と
して用い得るとの示唆は全く見られない。Some of the diphenoxygermanium phthalocyanine derivative compounds in which two phenoxy groups, which may have substituents, are bonded to a central metal, which are used as photoelectric conversion agents in the present invention, are described in the literature (R.D. Joyner et al., Journal of the American Chemical Society, Vol. 82, 5790-5791.
Page, published in 1960), but there is no suggestion that it can be used as a photoelectric conversion agent.
【０００８】本発明で用いられる化合物は、上記文献の
記載を参考にして、熱キノリン中において四塩化ゲルマ
ニウムを無金属フタロシアニンへ反応させてジクロロゲ
ルマニウムフタロシアニンを得た後、ピリジン−濃アン
モニア水を熱時作用させて加水分解して得たジヒドロキ
シゲルマニウムフタロシアニンヘ、熱ベンゼン中フェノ
ール誘導体を反応させることによって、光沢ある紫色結
晶として得ることができた。The compound used in the present invention is prepared by reacting germanium tetrachloride to metal-free phthalocyanine in hot quinoline to obtain dichlorogermanium phthalocyanine, and then reacting pyridine-concentrated ammonia water with reference to the above-mentioned literature. By reacting dihydroxygermanium phthalocyanine obtained by hydrolysis with a phenol derivative in hot benzene, it was possible to obtain shiny purple crystals.
【０００９】そして、これらの結晶性顔料は、もはや容
易には加水分解や脱水・重合のような化学的変化を受け
ることはなく安定であり、減圧下に加熱することによっ
て昇華・精製することができた。しかも、最も肝心なこ
とであるが、白色光照射下において極めて顕著な光電変
換作用を示したのである。例えば、透明電極上にジフェ
ノキシゲルマニウムフタロシアニンからなる薄膜を真空
蒸着法で設け、その上へ同じく真空蒸着法によってＮ，
Ｎ´−ジフェニル−３，４，９，１０−ペリレンテトラ
カルボン酸ジイミドからなる薄膜を設け、そこへ金電極
を付設したヘテロ接合型光電変換素子は、白色光照射に
よって顕著に光電流が観測された。[0009] These crystalline pigments are stable and do not easily undergo chemical changes such as hydrolysis, dehydration, or polymerization, and can be sublimated and purified by heating under reduced pressure. did it. Moreover, and most importantly, it showed an extremely remarkable photoelectric conversion effect under irradiation with white light. For example, a thin film made of diphenoxygermanium phthalocyanine is deposited on a transparent electrode by vacuum evaporation, and then N is deposited on top of it by vacuum evaporation.
In a heterojunction photoelectric conversion element in which a thin film made of N'-diphenyl-3,4,9,10-perylenetetracarboxylic acid diimide is provided and a gold electrode is attached thereto, a significant photocurrent is observed when irradiated with white light. Ta.
【００１０】本発明に含まれる化合物の具体例のいくつ
かを以下に示すが、簡単のために化１の式のフェノキシ
基部分のみを記載することとする。そして、本発明はこ
れらのみに限られない。Some specific examples of the compounds included in the present invention are shown below, but for the sake of simplicity, only the phenoxy group portion of the formula (1) will be described. However, the present invention is not limited to these.
【００１１】[0011]
【化２】[Case 2]
【００１２】0012
【化３】[Chemical formula 3]
【００１３】[0013]
【化４】[C4]
【００１４】[0014]
【化５】[C5]
【００１５】[0015]
【化６】[C6]
【００１６】[0016]
【化７】[C7]
【００１７】[0017]
【実施例】次に、本発明を実施例により、さらに詳細に
説明する。なお、以下に示す部および％は、断りのない
限り重量基準である。EXAMPLES Next, the present invention will be explained in more detail with reference to examples. Note that parts and percentages shown below are based on weight unless otherwise specified.
【００１８】実施例
例示化合物（化２、化３、化４、化５、化６もしくは化
７）１部とポリエステル樹脂（東洋紡製バイロン２００
）１部をテトラヒドロフラン１００部に混合し、ペイン
トコンデイショナー装置により、ガラスビーズと共に２
時間分散した。こうして得た分散液をアプリケーターに
て、アルミ蒸着ポリエステル上に塗布して、膜厚約０．
２μｍの電荷発生層（光電変換作用により電荷を発生す
る層）を形成した。塗布層は青色を呈し、可視光反射ス
ペクトルにおける吸収極大波長は６９０ｎｍ前後であっ
た。次に、ｐ−ジベンジルアミノベンズアルデヒド＝ジ
フェニルヒドラゾンを、ポリアリレート樹脂（ユニチカ
製Ｕ−ポリマー）と１：１の比で混合し、ジクロロエタ
ンを溶媒として１０％の溶液を作り、上記の電荷発生層
の上にアプリケーターにより塗布して、膜厚約２０μｍ
の電荷輸送層を形成した。Examples: 1 part of the exemplified compound (chemical formula 2, chemical compound 3, chemical compound 4, chemical compound 5, chemical compound 6 or chemical compound 7) and polyester resin (Vylon 200 manufactured by Toyobo Co., Ltd.)
) was mixed with 100 parts of tetrahydrofuran and mixed with glass beads in a paint conditioner machine.
Spread out time. The dispersion thus obtained was applied onto aluminum-deposited polyester using an applicator to a film thickness of approximately 0.
A charge generation layer (a layer that generates charges by photoelectric conversion) of 2 μm was formed. The coating layer exhibited a blue color, and the absorption maximum wavelength in the visible light reflection spectrum was around 690 nm. Next, p-dibenzylaminobenzaldehyde=diphenylhydrazone was mixed with a polyarylate resin (U-polymer manufactured by Unitika) at a ratio of 1:1, a 10% solution was prepared using dichloroethane as a solvent, and the above charge generation layer was prepared. Apply with an applicator on top of the film to a film thickness of approximately 20 μm.
A charge transport layer was formed.
【００１９】このようにして作成した積層型電子写真感
光体を、静電記録試験装置（川口電気製ＳＰ−４２８）
により電子写真特性評価を行った。
測定条件：印加電圧−６ｋＶ、スタテイックＮｏ．３（
ターンテーブルの回転スピードモード）その結果、電位
半減露光量はそれぞれ１．２８、１．３６、１．３０、
１．５４、１．０６もしくは１．９０ルックス・秒なる
値を示した。これは、極めて高感度であることを示すも
のである。The laminated electrophotographic photoreceptor thus produced was tested using an electrostatic recording tester (SP-428 manufactured by Kawaguchi Electric).
Electrophotographic characteristics were evaluated. Measurement conditions: Applied voltage -6kV, static No. 3(
Turntable rotation speed mode) As a result, the potential half-reduced exposure amount is 1.28, 1.36, 1.30, respectively.
It showed values of 1.54, 1.06 or 1.90 lux-seconds. This indicates extremely high sensitivity.
【００２０】[0020]
【発明の効果】本発明を実施することにより、加水分解
や脱水・重合のような化学変化を受けない安定な、しか
も顕著な光電変換作用を示す、ゲルマニウムフタロシア
ニン系有機光電変換剤を提供することが出来る。[Effects of the Invention] By carrying out the present invention, it is possible to provide a germanium phthalocyanine-based organic photoelectric conversion agent that is stable and exhibits a remarkable photoelectric conversion effect that is not subject to chemical changes such as hydrolysis, dehydration, and polymerization. I can do it.
Claims (1)
ニウムフタロシアニン誘導体からなる光電変換剤。 【化１】 （化１において、Ｒは水素、アルキル、アラルキル、ア
リールおよびハロゲンから選ばれる基を表し、ｎは５以
下の正の整数を表す。）1. A photoelectric conversion agent comprising a diphenoxygermanium phthalocyanine derivative represented by the following formula. [Formula 1] (In Formula 1, R represents a group selected from hydrogen, alkyl, aralkyl, aryl, and halogen, and n represents a positive integer of 5 or less.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3163557A JP2871898B2 (en) | 1991-06-06 | 1991-06-06 | Germanium phthalocyanine-based photoelectric conversion agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3163557A JP2871898B2 (en) | 1991-06-06 | 1991-06-06 | Germanium phthalocyanine-based photoelectric conversion agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04360150A true JPH04360150A (en) | 1992-12-14 |
| JP2871898B2 JP2871898B2 (en) | 1999-03-17 |
Family
ID=15776165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3163557A Expired - Fee Related JP2871898B2 (en) | 1991-06-06 | 1991-06-06 | Germanium phthalocyanine-based photoelectric conversion agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2871898B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998032824A3 (en) * | 1997-01-24 | 1998-09-11 | Procter & Gamble | Singlet oxygen generators having enhanced heavy atom effect |
| WO1998032826A3 (en) * | 1997-01-24 | 1998-09-11 | Procter & Gamble | Photobleaching compositions comprising mixed metallocyanines |
| WO1998032825A3 (en) * | 1997-01-24 | 1998-10-01 | Procter & Gamble | Photochemical singlet oxygen generators having enhanced singlet oxygen yields |
| US8933238B2 (en) | 2013-03-11 | 2015-01-13 | Saudi Basic Industries Corporation | Aryloxy-phthalocyanines of group III metals |
| WO2014140850A3 (en) * | 2013-03-11 | 2015-04-02 | Saudi Basic Industries Corporation | Aryloxy-phthalocyanines of group iv metals for use in solar cells |
-
1991
- 1991-06-06 JP JP3163557A patent/JP2871898B2/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998032824A3 (en) * | 1997-01-24 | 1998-09-11 | Procter & Gamble | Singlet oxygen generators having enhanced heavy atom effect |
| WO1998032826A3 (en) * | 1997-01-24 | 1998-09-11 | Procter & Gamble | Photobleaching compositions comprising mixed metallocyanines |
| WO1998032825A3 (en) * | 1997-01-24 | 1998-10-01 | Procter & Gamble | Photochemical singlet oxygen generators having enhanced singlet oxygen yields |
| US8933238B2 (en) | 2013-03-11 | 2015-01-13 | Saudi Basic Industries Corporation | Aryloxy-phthalocyanines of group III metals |
| WO2014140850A3 (en) * | 2013-03-11 | 2015-04-02 | Saudi Basic Industries Corporation | Aryloxy-phthalocyanines of group iv metals for use in solar cells |
| US9040710B2 (en) | 2013-03-11 | 2015-05-26 | Saudi Basic Industries Corporation | Aryloxy-phthalocyanines of group IV metals |
| CN105051049A (en) * | 2013-03-11 | 2015-11-11 | 沙特基础工业公司 | Aryloxy-phthalocyanines of group IV metals for use in solar cells |
| JP2016516013A (en) * | 2013-03-11 | 2016-06-02 | サウジ ベイシック インダストリーズ コーポレイション | Group IV metal aryloxy-phthalocyanines for use in solar cells |
| US9362509B2 (en) | 2013-03-11 | 2016-06-07 | Saudi Basic Industries Corporation | Aryloxy-phthalocyanines of group IV metals |
| CN107068871A (en) * | 2013-03-11 | 2017-08-18 | 沙特基础工业公司 | Plane donor-acceptor hetero-junctions and the photovoltaic cell comprising it |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2871898B2 (en) | 1999-03-17 |
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