JPS6330566A - Indium phthalocyanine hexadecafluoride compound - Google Patents
Indium phthalocyanine hexadecafluoride compoundInfo
- Publication number
- JPS6330566A JPS6330566A JP17371086A JP17371086A JPS6330566A JP S6330566 A JPS6330566 A JP S6330566A JP 17371086 A JP17371086 A JP 17371086A JP 17371086 A JP17371086 A JP 17371086A JP S6330566 A JPS6330566 A JP S6330566A
- Authority
- JP
- Japan
- Prior art keywords
- hexadecafluoride
- phthalocyanine
- indium
- indium phthalocyanine
- compound
- 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
- 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 abstract description 22
- 229910052738 indium Inorganic materials 0.000 title claims abstract description 15
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 title claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- FOVZCYAIUZHXGB-UHFFFAOYSA-M indium(1+);iodide Chemical compound I[In] FOVZCYAIUZHXGB-UHFFFAOYSA-M 0.000 abstract description 6
- 239000007858 starting material Substances 0.000 abstract description 4
- OFLRJMBSWDXSPG-UHFFFAOYSA-N 3,4,5,6-tetrafluorobenzene-1,2-dicarbonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(C#N)=C1F OFLRJMBSWDXSPG-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- RMUKCGUDVKEQPL-UHFFFAOYSA-K triiodoindigane Chemical compound I[In](I)I RMUKCGUDVKEQPL-UHFFFAOYSA-K 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- AHXBXWOHQZBGFT-UHFFFAOYSA-M 19631-19-7 Chemical compound N1=C(C2=CC=CC=C2C2=NC=3C4=CC=CC=C4C(=N4)N=3)N2[In](Cl)N2C4=C(C=CC=C3)C3=C2N=C2C3=CC=CC=C3C1=N2 AHXBXWOHQZBGFT-UHFFFAOYSA-M 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 indium phthalocyanine compounds Chemical class 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XPHWZABCPRKTIK-UHFFFAOYSA-M [OH-].[In+] Chemical compound [OH-].[In+] XPHWZABCPRKTIK-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 2
- 229920006391 phthalonitrile polymer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- XGDBOJRURXXJBF-UHFFFAOYSA-M fluoroindium Chemical compound [In]F XGDBOJRURXXJBF-UHFFFAOYSA-M 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（利用分野〕
本発明は、下記一般式（Ｉ）で示される新規なインジウ
ムフタロシアニンヘキサデカフルオリド類化合物に関す
るものである。DETAILED DESCRIPTION OF THE INVENTION (Field of Application) The present invention relates to a novel indium phthalocyanine hexadecafluoride compound represented by the following general formula (I).
〔（１）式中Ｘは沃素、臭素、塩素、フッ素またはヒド
ロキシル基を表わす。）
すなわち、本発明にかかる新規なインジウムフタロシア
ニンヘキサデカフルオリド類化合物は、フッ素化された
芳香環をもち、従来知られているインジウムフタロシア
ニン類化合物と異なる特殊な機能を有するものであり、
例えば耐光性の高い高級顔料、光情報記録媒体、光電変
換媒体あるいは電子写真感光体などとして用いる際に、
優れた効果を発揮するものである。[In the formula (1), X represents iodine, bromine, chlorine, fluorine or a hydroxyl group. ) That is, the novel indium phthalocyanine hexadecafluoride compound according to the present invention has a fluorinated aromatic ring and has special functions different from conventionally known indium phthalocyanine compounds,
For example, when used as a high-grade pigment with high light resistance, an optical information recording medium, a photoelectric conversion medium, or an electrophotographic photoreceptor,
It exhibits excellent effects.
本発明が提供するインジウムフタロシアニンヘキサデカ
フルオリド類化合物は、今まで全く報告されていない。The indium phthalocyanine hexadecafluoride compound provided by the present invention has not been reported at all to date.
一方、フッ素を含有していないインジウムフタロシアニ
ン類化合物の合成法は公知である。例えばインオーガニ
ック ケミストリー（Ｉｎｏｒｇａｎｉｃ Ｃｈｅｍｉ
ｓｔｒｙ ） 、 １９８０年、第３１３１頁記載の方
法によると、フタロニトリルを出発原料としてキノリン
溶媒中で塩化インジウム（ＩｎＣｌ３）と反応させて、
クロロインジウムフタロシアニンをえている。また、例
えばクリスタル ラント テヒニーク（にｒｉｓｔ、Ｔ
ｅｃｈ、 ）、第２巻、第４３１頁、１９６７年記載の
方法によるとフタロニトリルとＩｎＣｌ３とを溶融状態
で反応させて、クロロインジウムフタロシアニンクロリ
ドをえでいる。On the other hand, methods for synthesizing indium phthalocyanine compounds that do not contain fluorine are known. For example, Inorganic Chemistry
According to the method described in ``Stry'', 1980, p. 3131, phthalonitrile is reacted with indium chloride (InCl3) in a quinoline solvent as a starting material,
Contains chloroindium phthalocyanine. Also, for example, crystal
ech, Vol. 2, p. 431, 1967, phthalonitrile and InCl3 are reacted in a molten state to produce chloroindium phthalocyanine chloride.
しかし、本発明が目的とするようなフッ素置換基のある
テトラフルオロフタロニトリルを出発原料として、イン
ジウムヘキサデ力フルオリド類化合物を製造する場合、
上記公知方法である、その芳香環にフッ素を含有してい
ないクロロインジウムフタロシアニン類化合物の一般的
な合成法は適用できない。なぜならば、前者の場合キノ
リンとテトラフルオロフタ、ロニトリルが先にコンプレ
ックスをつくり、フタロシアニン化の反応が起りにくく
なる。また後者の場合、キノリンのような塩素のトラッ
プ剤がないために、反応によって生じた塩素の一部がフ
ッ素の一部で置換反応を起し、よってインジウムフタロ
シアニンヘキサデカフルオリド類化合物を純度良く合成
することができないからである。However, when producing an indium hexadefluoride fluoride compound using tetrafluorophthalonitrile having a fluorine substituent as a starting material as the object of the present invention,
The above-mentioned known method, which is a general method for synthesizing chloroindium phthalocyanine compounds that do not contain fluorine in their aromatic ring, cannot be applied. This is because in the former case, quinoline, tetrafluorophtha, and ronitrile form a complex first, making it difficult for the phthalocyanation reaction to occur. In the latter case, since there is no chlorine trapping agent such as quinoline, some of the chlorine generated by the reaction undergoes a substitution reaction with some of the fluorine, resulting in a highly pure indium phthalocyanine hexadecafluoride compound. This is because they cannot be synthesized.
本発明者らは式（Ｉ）で示される新規なインジウムフタ
ロシアニンヘキサデカフルオリド類化合物を高収率でえ
る製造方法を検討した結果、３，４゜５．６−テトラフ
ルオロフタロニトリルとヨウ化インジウムとをベンゼン
、トルエン、キシレン、ニトロベンゼン、モノクロロベ
ンゼン、ジクロロベンゼン、トリクロロベンゼン、クロ
ロナフタレン、メチルナフタレンなどの不活性有機溶媒
中、あるいは有機溶媒を存在させないで１３０〜３００
℃の温度で加熱することによって、ヨードインジウムフ
タロシアニンヘキサデカフルオリドを製造できることを
見い出した。かくしてえられるヨードインジウムフタロ
シアニンへキサデ力フＪレオリドを出発原料として用い
ることにより各種のインジウムフタロシアニンヘキサデ
カフルオリド類化合物をも製造できる。例えばヒドロキ
シルインジウムフタロシアニンヘキサデカフルオリドは
、アンモニア水とピリジン混合溶媒中で加熱することに
よってえることができる。また例えばフルオロインジウ
ムフタロシアニンヘキサデカフルオリドは、このヒドロ
キシインジウムフタロシアニンヘキサデカフルオリドを
フッ化水素酸水溶液中に加え、これを蒸発乾固すること
によってえられる。また例えばクロロインジウムフタロ
シアニンヘキサデカフルオリドは、前述のフルオロイン
ジウムフタロシアニンヘキサデカフルオリドの合成方法
においてフッ化水素酸のかわりに塩酸を使うことによっ
てえられる。The present inventors investigated a method for producing a novel indium phthalocyanine hexadecafluoride compound represented by formula (I) in high yield, and found that 3,4°5,6-tetrafluorophthalonitrile and iodide in an inert organic solvent such as benzene, toluene, xylene, nitrobenzene, monochlorobenzene, dichlorobenzene, trichlorobenzene, chloronaphthalene, methylnaphthalene, or in the absence of an organic solvent.
It has been found that iodoindium phthalocyanine hexadecafluoride can be produced by heating at a temperature of .degree. Various indium phthalocyanine hexadecafluoride compounds can also be produced by using the thus obtained iodoindium phthalocyanine hexadecafluoride as a starting material. For example, hydroxylindium phthalocyanine hexadecafluoride can be obtained by heating in a mixed solvent of aqueous ammonia and pyridine. For example, fluoroindium phthalocyanine hexadecafluoride can be obtained by adding this hydroxyindium phthalocyanine hexadecafluoride to an aqueous solution of hydrofluoric acid and evaporating the solution to dryness. For example, chloroindium phthalocyanine hexadecafluoride can be obtained by using hydrochloric acid in place of hydrofluoric acid in the aforementioned method for synthesizing fluorindium phthalocyanine hexadecafluoride.
なお、本発明にかかるインジウムフタロシアニンヘキサ
デカフルオリド類化合物の製造方法が上記のものに限定
されないことはもちろんである。It goes without saying that the method for producing an indium phthalocyanine hexadecafluoride compound according to the present invention is not limited to the above method.
以下、本発明を実施例により更に具体的に説明し、えら
れたこれらの新規物質を特定するための分析結果をも同
時に示す。Hereinafter, the present invention will be explained in more detail with reference to Examples, and analysis results for specifying these novel substances obtained will also be shown at the same time.
実施例 １
５０ｄの４ツロセバラブルフラスコ中に、３，４゜５．
６−テトラフルオロフタロニトリル２０．０ ｇ（０，
１０モル）と無水ヨウ化インジウム１２．３８ｇ（０，
０２５モル）とを仕込み、ゆっくり撹拌しながら９０℃
まで加熱し、３．４．５．６−チトラフルオロフタロニ
トリルを溶融せしめた。その後約１時間かけてさらに２
００℃の温度まで激しく撹拌しながら昇温し、次いで２
００℃の温度で１時間保ち、室温まで放冷したところ暗
青色の固形物をえた。この固形物を乳鉢で粉砕し、つい
で希塩酸、水、エタノールおよびベンゼンの順番で洗浄
し、１１０℃で２時間乾燥した。かくしてヨードインジ
ウムフタロシアニンヘキサデカフルオリド２３゜９０（
対テトラフルオロフタロニトリル９０．４モル％収率）
をえた。Example 1 In a 50d four-way adjustable flask, 3.4°5.
6-tetrafluorophthalonitrile 20.0 g (0,
10 moles) and 12.38 g of anhydrous indium iodide (0,
025 mol) and heated to 90°C while stirring slowly.
3.4.5.6-titrafluorophthalonitrile was melted. After that, about 1 hour later, 2 more
The temperature was raised to a temperature of 00°C with vigorous stirring, and then 2
The mixture was kept at a temperature of 00°C for 1 hour and allowed to cool to room temperature, yielding a dark blue solid. This solid was ground in a mortar, washed with dilute hydrochloric acid, water, ethanol and benzene in this order, and dried at 110°C for 2 hours. Thus, iodoindium phthalocyanine hexadecafluoride 23°90 (
90.4 mol% yield of tetrafluorophthalonitrile)
I got it.
０元素分析値
Ｈ（Ｘ） Ｃ（Ｘ） Ｎ（Ｘ） Ｆ（％） ｌ（
％） Ｉｎ（％）理論値 ０ ３６．８８１０．７５
２９．１７１２．１８ １０．９６分析値０．０８３６
．４６１０．８１２９．８３１２．６６ １０．１６０
可視吸収スペクトル（ジメチルホルムアミド中）λｍａ
ｘ ； ６８３ｎｖ （ｌｏｇε； ４．７４）λ
ＩｎａＸ ： ６４０ｎｌｌｌ （ｌｏｇε；
４．５９）０赤外線吸収スペクトル＜ＫＢｒ板）
この物質の赤外線吸収スペクトルを第１図に示した。0 elemental analysis value H(X) C(X) N(X) F(%) l(
%) In(%) Theoretical value 0 36.8810.75
29.1712.18 10.96 analysis value 0.0836
．． 4610.8129.8312.66 10.160
Visible absorption spectrum (in dimethylformamide) λma
x; 683nv (logε; 4.74)λ
InaX: 640nllll (logε;
4.59) 0 Infrared absorption spectrum <KBr plate) The infrared absorption spectrum of this material is shown in FIG.
第１図は実施例でえられたヨードインジウムフタロシア
ニンヘキサデカフルオリドの赤外線吸収スペクトル図で
ある。FIG. 1 is an infrared absorption spectrum diagram of iodoindium phthalocyanine hexadecafluoride obtained in Examples.
Claims (2)
シアニンヘキサデカフルオリド類化合物。 ▲数式、化学式、表等があります▼………（ I ） 〔（ I ）式中Ｘは沃素、臭素、塩素、フッ素またはヒ
ドロキシル基を表わす。〕(1) An indium phthalocyanine hexadecafluoride compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼......(I) [(I) In the formula, X represents iodine, bromine, chlorine, fluorine, or a hydroxyl group. ]
（１）記載のインジウムフタロシアニンヘキサデカフル
オリド。(2) Indium phthalocyanine hexadecafluoride according to claim (1), wherein X in the formula (I) is iodine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17371086A JPS6330566A (en) | 1986-07-25 | 1986-07-25 | Indium phthalocyanine hexadecafluoride compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17371086A JPS6330566A (en) | 1986-07-25 | 1986-07-25 | Indium phthalocyanine hexadecafluoride compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6330566A true JPS6330566A (en) | 1988-02-09 |
Family
ID=15965697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17371086A Pending JPS6330566A (en) | 1986-07-25 | 1986-07-25 | Indium phthalocyanine hexadecafluoride compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6330566A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005240032A (en) * | 2004-01-29 | 2005-09-08 | Mitsubishi Chemicals Corp | Fluorinated indium phthalocyanine, electrophotographic photosensitive body using the same electrophotographic photosensitive body cartridge, and image forming apparatus |
-
1986
- 1986-07-25 JP JP17371086A patent/JPS6330566A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005240032A (en) * | 2004-01-29 | 2005-09-08 | Mitsubishi Chemicals Corp | Fluorinated indium phthalocyanine, electrophotographic photosensitive body using the same electrophotographic photosensitive body cartridge, and image forming apparatus |
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