JPH046700B2 - - Google Patents
Info
- Publication number
- JPH046700B2 JPH046700B2 JP59092769A JP9276984A JPH046700B2 JP H046700 B2 JPH046700 B2 JP H046700B2 JP 59092769 A JP59092769 A JP 59092769A JP 9276984 A JP9276984 A JP 9276984A JP H046700 B2 JPH046700 B2 JP H046700B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- squarium
- compound
- atom
- fluorine atom
- 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.)
- Expired - Lifetime
Links
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
Landscapes
- Light Receiving Elements (AREA)
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
産業上の利用分野
本発明は電子写真用感光体の電荷発生物質とし
て、可視域から近赤外の波長域にわたつてフラツ
トな光感度を有する新規なスクエアリウム化合物
及びその製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention is directed to a novel squarium compound and a novel squarium compound having a flat photosensitivity over a wavelength range from the visible to near infrared wavelengths as a charge generating material for electrophotographic photoreceptors. It relates to its manufacturing method.
従来技術
従来、電子写真用感光材料として数多くの物質
が知られている。中でも、長波長域に光感度を示
すものとしてSe／Te、Se／As、CdSe、フタロ
シアニン化合物などがある。このうち、Se／Te
などの無機化合物は可視域から近赤外域にわたつ
てフラツトな感度を有する感光体を得ることが難
しく、また可撓性がないためベルト状に加工する
ことが困難であるなど多くの問題点がある。ま
た、有機化合物のフタロシアニン化合物は550nm
以下での光感度が低いことと、精製が困難である
ことが問題であり、可視域から近赤外域にわたつ
てフラツトな光感度を示す実用的な物質はみつか
つていない。BACKGROUND OF THE INVENTION Conventionally, many substances have been known as photosensitive materials for electrophotography. Among these, compounds that exhibit photosensitivity in the long wavelength range include Se/Te, Se/As, CdSe, and phthalocyanine compounds. Of these, Se/Te
Inorganic compounds, such as be. In addition, phthalocyanine compounds, which are organic compounds, have a wavelength of 550 nm.
Problems include low photosensitivity below and difficulty in purification, and no practical substance has yet been found that exhibits flat photosensitivity from the visible region to the near-infrared region.
発明の目的
本発明の目的は可視域から近赤外の波長域の全
体にわたつてフラツトな光感度を有する新規なス
クエアリウム化合物を提供することにある。OBJECTS OF THE INVENTION An object of the present invention is to provide a novel squarium compound having a flat photosensitivity over the entire wavelength range from visible to near infrared.
発明の構成
本発明者等は鋭意検討の結果、前記の目的にか
なつた新規なスクエアリウム化合物及びその製造
方法を見出し、本発明を完成した。Structure of the Invention As a result of extensive studies, the present inventors have discovered a novel squarium compound and a method for producing the same that meet the above objectives, and have completed the present invention.
すなわち本発明の第１の対象は下記一般式
（）で示されるスクエアリウム化合物である。 That is, the first object of the present invention is a squarium compound represented by the following general formula ().
上記の式中、Ｘはフツ素原子又は塩素原子を表
わし、Ｙは水素原子又はフツ素原子を表わす。 In the above formula, X represents a fluorine atom or a chlorine atom, and Y represents a hydrogen atom or a fluorine atom.
本発明の第２の対象は式（）
で示される３，４−ジヒドロキシ−３−シクロブ
テン−１，２−ジオン（以下、スクエアリン酸と
呼ぶ）と一般式（）
（式中、Ｘ及びＹは前記と同じ意味を表わす。）
で示されるアニリン誘導体とを反応させることを
特徴とする前記の新規なスクエアリウム化合物の
製造方法である。 The second object of the present invention is the expression () 3,4-dihydroxy-3-cyclobutene-1,2-dione (hereinafter referred to as squaric acid) represented by the general formula () (In the formula, X and Y represent the same meanings as above.)
This is a method for producing the above-mentioned novel squarium compound, characterized by reacting it with an aniline derivative represented by:
前記の新規スクエアリウム化合物は、スクエア
リン酸とアニリン誘導体を溶媒（例えば、ｎ−ブ
チルアルコールあるいはアミルアルコール）中
で、110〜140℃で３時間から５時間反応させるこ
とによつて得られる。得られた化合物は、洗浄後
さらに適当な溶媒で再結晶することによつて精製
される。 The novel squarium compound described above can be obtained by reacting squaric acid and an aniline derivative in a solvent (for example, n-butyl alcohol or amyl alcohol) at 110 to 140°C for 3 to 5 hours. After washing, the obtained compound is further purified by recrystallization from a suitable solvent.
この様にして得られる本発明の新規なスクエア
リウム化合物の具体例を構造式で以下の表１に示
す。 Specific examples of the novel squarium compounds of the present invention obtained in this manner are shown in Table 1 below in terms of structural formulas.
このようにして製造される新規なスクエアリウ
ム化合物は、積層型感光体の電荷発生物質として
有効である。 The novel squarium compound thus produced is effective as a charge-generating material for laminated photoreceptors.
また、分光感度は400〜850nmの範囲にわたつ
てフラツトな光感度を示し、全可視域及び近赤外
域において充分な光感度を有する。 Moreover, the spectral sensitivity shows flat photosensitivity over the range of 400 to 850 nm, and has sufficient photosensitivity in the entire visible region and near-infrared region.
発明の効果
従つて本発明のスクエアリウム化合物は通常の
電子写真用複写機のみならず、半導体レーザープ
リンターとしての応用が可能で、インテリジエン
ト複写機として広く用いることができる。また電
子写真分野以外にも、レーザーデイスクなどの光
学記録媒体としてや有機太陽電池などの様々な応
用が可能である。Effects of the Invention Therefore, the squarium compound of the present invention can be applied not only to ordinary electrophotographic copying machines but also to semiconductor laser printers, and can be widely used as intelligent copying machines. Furthermore, in addition to the field of electrophotography, various applications such as optical recording media such as laser disks and organic solar cells are possible.
次に本発明を実施例により説明する。 Next, the present invention will be explained by examples.
実施例 １
化合物(1)の製造
Ｎ−（４−フルオロベンジル）−Ｎ−メチル−ｎ
−トルイジン7.92ｇとスクエアリン酸2.0ｇをｎ
−ブチルアルコールとトルエンの混合溶媒中で撹
拌しながら100〜120℃にて５時間加熱した。冷却
後、析出した緑色結晶を過し、メタノールで洗
浄し、目的物をスクエアリウムを0.41ｇ（4.4％）
得た。Example 1 Production of compound (1) N-(4-fluorobenzyl)-N-methyl-n
- Toluidine 7.92g and squaric acid 2.0g n
-Heating at 100 to 120°C for 5 hours while stirring in a mixed solvent of butyl alcohol and toluene. After cooling, the precipitated green crystals were filtered and washed with methanol, and the target product was 0.41g (4.4%) of Squarium.
Obtained.
分解点：240〜241℃。 Decomposition point: 240-241℃.
赤外吸収スペクトル（KBr錠剤法）： ν＝1630cm-1。 Infrared absorption spectrum (KBr tablet method): ν=1630cm -1 .
可視スペクトル：647nm（ジクロロメタン溶液中）
元素分析：
計算値 実測値
Ｃ 76.10％ 76.39％
Ｈ 5.63％ 5.42％
Ｎ 5.22％ 5.01％
実施例 ２〜３
相当するアニリン誘導体を用いて実施例１と同
様にして化合物(2)及び(3)を得た。Visible spectrum: 647 nm (in dichloromethane solution) Elemental analysis: Calculated value Actual value C 76.10% 76.39% H 5.63% 5.42% N 5.22% 5.01% Examples 2-3 Same as Example 1 using the corresponding aniline derivative Compounds (2) and (3) were obtained.
化合物(2)： 分解点：232.5〜233.5℃ 赤外吸収スペクトル（KBr錠剤法）： ν＝1590cm-1。Compound (2): Decomposition point: 232.5 to 233.5°C Infrared absorption spectrum (KBr tablet method): ν = 1590 cm -1 .
可視スペクトル：λmax＝647nm（ジクロロメタ
ン中）。Visible spectrum: λmax = 647 nm (in dichloromethane).
元素分析： 計算値 実測値 Ｃ 71.70％ 71.55％ Ｈ 5.31％ 5.28％ Ｎ 4.92％ 5.08％ 化合物(3)： 分解点：245.0〜245.5℃ 赤外吸収スペクトル（KBr錠剤法）： ν＝1590cm-1。Elemental analysis: Calculated value Actual value C 71.70% 71.55% H 5.31% 5.28% N 4.92% 5.08% Compound (3): Decomposition point: 245.0 to 245.5°C Infrared absorption spectrum (KBr tablet method): ν = 1590 cm -1 .
電子スペクトル：λmax＝639nm（ジクロロメタ
ン中）。Electronic spectrum: λmax = 639 nm (in dichloromethane).
元素分析： 計算値 実測値 Ｃ 60.01％ 60.29％ Ｈ 3.26％ 3.19％ Ｎ 4.12％ 4.03％Elemental analysis: Calculated value Actual value C 60.01% 60.29% H 3.26% 3.19% N 4.12% 4.03%
Claims (1)
し、Ｙは水素原子又はフツ素原子を表わす。） で示されるスクエアリウム化合物。 ２ 式（） で示される３，４−ジヒドロキシ−３−シクロブ
テン−１，２−ジオと一般式（） （式中、Ｘはフツ素原子又は塩素原子を表わ
し、Ｙは水素原子又はフツ素原子を表わす。） で示されるアニリン誘導体とを反応させることを
特徴とする一般式（） （式中、Ｘ及びＹは前記と同じ意味を表わす。） で示されるスクエアリウム化合物の製造方法。[Claims] 1 General formula () (In the formula, X represents a fluorine atom or a chlorine atom, and Y represents a hydrogen atom or a fluorine atom.) A squarium compound represented by the following. 2 formula () 3,4-dihydroxy-3-cyclobutene-1,2-dio represented by the general formula () (In the formula, X represents a fluorine atom or a chlorine atom, and Y represents a hydrogen atom or a fluorine atom.) General formula () characterized by reacting with an aniline derivative represented by (In the formula, X and Y represent the same meanings as above.) A method for producing a squarium compound represented by the following.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59092769A JPS60260547A (en) | 1984-05-11 | 1984-05-11 | Novel squarium compound and preparation thereof |
| EP19850105887 EP0161005B1 (en) | 1984-05-11 | 1985-05-13 | Novel squarium compounds, process for preparing the same and electrophotographic photoreceptors containing the same |
| DE8585105887T DE3574866D1 (en) | 1984-05-11 | 1985-05-13 | "SQUARIUM" COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF, AND ELECATROPHOTOGRAPHIC PHOTOREEPEPTORS THAT CONTAIN THEM. |
| US07/232,990 US5210301A (en) | 1984-05-11 | 1988-08-17 | Squarium compounds, process for preparing the same and electrophotographic photoreceptors containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59092769A JPS60260547A (en) | 1984-05-11 | 1984-05-11 | Novel squarium compound and preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60260547A JPS60260547A (en) | 1985-12-23 |
| JPH046700B2 true JPH046700B2 (en) | 1992-02-06 |
Family
ID=14063627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59092769A Granted JPS60260547A (en) | 1984-05-11 | 1984-05-11 | Novel squarium compound and preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60260547A (en) |
-
1984
- 1984-05-11 JP JP59092769A patent/JPS60260547A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60260547A (en) | 1985-12-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |