JPH0348948B2 - - Google Patents
Info
- Publication number
- JPH0348948B2 JPH0348948B2 JP58236203A JP23620383A JPH0348948B2 JP H0348948 B2 JPH0348948 B2 JP H0348948B2 JP 58236203 A JP58236203 A JP 58236203A JP 23620383 A JP23620383 A JP 23620383A JP H0348948 B2 JPH0348948 B2 JP H0348948B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methyl group
- represents hydrogen
- squarium
- 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.)
- 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
本発明は電子写真感光体の電荷生物質として、
可視域から近赤外の波長域にわたつて光感度を有
する新規なスクエアリウム化合物およびその製造
方法に関する。
従来、電子写真用感光用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などの
無機化合物がある。これら無機化合物の多くは毒
物、劇物あるいは特定化学物質に指定され、その
取扱い、特に廃棄には注意を要するとともに、製
造が難かしく、製造コストが高いという欠点があ
る。また、可撓性がないためベルト状に加工する
ことが困難であることなど多くの問題点がある。
一方、有機化合物としてはフタロシアニン化合
物が毒性がなく安価であるが、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。
本発明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したものである。
すなわち、本発明の第１の対象は下記一般式
（）で示される新規なスクエアリウム化合物で
ある。
（式中、Ｘは水素、メチル基又はハロゲン原子を
表わし、Ｒは水素又はメチル基を表わす。）
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（以下スクエリアリツクア
シツドと呼ぶ）と式（）
（式中、Ｘ及びＲ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。
前記の新規スクエアリウム化合物はスクエアリ
ツクシツドとアニリン誘導体を溶媒（例えばｎ−
ブタノールあるいはアミルアルコール）中で、
120〜140℃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り精製され
る。
この様にして得られる本発明の新規スクエアリ
ウム化合物の具体例の構造式で次に示す。
この様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。
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、全可視域および近
赤外域において、充分な光感度を有する。
従つて通常の電子写真複写機のみならず、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られるま
た、電子写真分野以外にもレーザーデイスクなど
の光学録媒体として有機太陽電池など様様な応用
が可能である。
次に本発明を実施例により説明する。
実施例 １
化合物(1)の製造
Ｎ−ベンジル−Ｎ−メチルアニリン24.8ｇと
３，４−ジヒドロキシ−３−シクロブテン−１，
２−ジオン0.76ｇをｎ−ブタノール26.8ml中に加
え、撹拌しながら130〜140℃で４時間加熱した。
冷却後、折出した淡緑色の輝く結晶を過し、メ
タノールで洗浄後、、乾燥して目的のスクエアリ
ウム色素0.85ｇ（26.8％）を得た。
分解点：259℃
赤外線吸収スペクトル（KBr錠剤法）：
νc：ｏ＝1590cm-1。
元素分析：
実測値 計算値
Ｃ 81.27％ 81.33％
Ｈ 5.86％ 5.97％
Ｎ 6.02％ 5.93％
可視吸収スペクトル：
λmax＝633nｍ（ジクロロメタン溶液中）。
実施例 ２〜４
アニリンの誘導体をかえて、実施例１と同様に
して３，４−ジヒドロキシ−３−シクロブテンと
アニリン誘導体を反応させた。表１に生成した各
化合物の分解点、赤外吸収スペクトルおよび可視
吸収スペクトルの数値を示し、表２に元素分析の
結果を示した。
The present invention provides a charge biological material for an electrophotographic photoreceptor,
The present invention relates to a novel squarium compound having photosensitivity in the visible to near-infrared wavelength range, and a method for producing the same. Conventionally, many substances have been known as photosensitive materials for electrophotography. Among them, there are inorganic compounds such as Se/Te, Se/As, and CdSe that exhibit photosensitivity in the long wavelength range. Many of these inorganic compounds are designated as poisonous, deleterious substances, or specified chemical substances, and they require careful handling, especially disposal, and have the drawbacks of being difficult and expensive to manufacture. Furthermore, there are many problems such as the fact that it is difficult to process it into a belt shape due to its lack of flexibility. On the other hand, among organic compounds, phthalocyanine compounds are non-toxic and inexpensive, but they suffer from low photosensitivity at wavelengths below 550 nm and difficulty in purification. No practical substance that exhibits photosensitivity has yet been found. The present invention provides a novel squarium compound having a flat photosensitivity over the entire wavelength range from visible to near-infrared. That is, the first object of the present invention is a novel squarium compound represented by the following general formula (). (In the formula, X represents hydrogen, a methyl group, or a halogen atom, and R represents hydrogen or a methyl group.) The second object of the present invention is the formula () 3,4-dihydroxy-3-cyclobutene-1,2-dione (hereinafter referred to as square acid) represented by the formula () (In the formula, X and R have 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: The novel squarium compound described above combines squarium compound and aniline derivative with a solvent (e.g. n-
butanol or amyl alcohol)
It is obtained by reacting at 120 to 140°C for 3 to 5 hours. After washing, the obtained compound is further purified by recrystallization from an appropriate solvent. The structural formula of a specific example of the novel squarium compound of the present invention obtained in this manner is shown below. The novel squarium compound produced in this manner is effective as a charge-generating material for laminated photoreceptors. 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. Therefore, it can be applied not only to ordinary electrophotographic copying machines but also as semiconductor laser printers, and is widely used as intelligent copying machines.In addition to the electrophotographic field, it can also be used as optical recording media such as laser disks, organic solar cells, etc. Various applications are possible. Next, the present invention will be explained by examples. Example 1 Production of compound (1) 24.8 g of N-benzyl-N-methylaniline and 3,4-dihydroxy-3-cyclobutene-1,
0.76 g of 2-dione was added to 26.8 ml of n-butanol and heated at 130-140° C. for 4 hours with stirring.
After cooling, the precipitated pale green shining crystals were filtered, washed with methanol, and dried to obtain 0.85 g (26.8%) of the desired squarium pigment. Decomposition point: 259°C Infrared absorption spectrum (KBr tablet method): νc: o = 1590 cm -1 . Elemental analysis: Actual value Calculated value C 81.27% 81.33% H 5.86% 5.97% N 6.02% 5.93% Visible absorption spectrum: λmax = 633 nm (in dichloromethane solution). Examples 2 to 4 3,4-dihydroxy-3-cyclobutene and an aniline derivative were reacted in the same manner as in Example 1, except that the aniline derivative was changed. Table 1 shows the decomposition point, infrared absorption spectrum, and visible absorption spectrum of each compound produced, and Table 2 shows the results of elemental analysis.
【表】
＊ジクロルメタン溶液中
[Table] *In dichloromethane solution
【表】【table】
Claims (1)
表わし、Ｒは水素又はメチル基を表わす。）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
デン−１，２−ジオンと一般式（） （式中、Ｘは水素、メチル基又はハロゲン原子を
表わし、Ｒは水素又はメチル基を表わす。）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Ｒ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 hydrogen, a methyl group, or a halogen atom, and R represents hydrogen or a methyl group.) A squarium compound represented by the formula: 2 formula () 3,4-dihydroxy-3-cyclobutene-1,2-dione represented by the general formula () (In the formula, X represents hydrogen, a methyl group, or a halogen atom, and R represents hydrogen or a methyl group.) General formula () characterized by reacting with an aniline derivative represented by (In the formula, X and R have the same meanings as above.)
A method for producing a squarium compound shown in
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58236203A JPS60130558A (en) | 1983-12-16 | 1983-12-16 | Novel squarium compound and its preparation |
| DE8484115344T DE3465985D1 (en) | 1983-12-16 | 1984-12-13 | Novel squarylium compound and photoreceptor containing same |
| EP84115344A EP0146123B1 (en) | 1983-12-16 | 1984-12-13 | Novel squarylium compound and photoreceptor containing same |
| US06/942,922 US4908289A (en) | 1983-12-16 | 1986-12-17 | Photoreceptor for electrophotography |
| US07/091,340 US4752650A (en) | 1983-12-16 | 1987-08-31 | Photoreceptor for electrophotography |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58236203A JPS60130558A (en) | 1983-12-16 | 1983-12-16 | Novel squarium compound and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60130558A JPS60130558A (en) | 1985-07-12 |
| JPH0348948B2 true JPH0348948B2 (en) | 1991-07-26 |
Family
ID=16997305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58236203A Granted JPS60130558A (en) | 1983-12-16 | 1983-12-16 | Novel squarium compound and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60130558A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63113464A (en) * | 1986-10-30 | 1988-05-18 | Fuji Xerox Co Ltd | Electrophotographic sensitive body |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4508803A (en) * | 1983-12-05 | 1985-04-02 | Xerox Corporation | Photoconductive devices containing novel benzyl fluorinated squaraine compositions |
| US4521621A (en) * | 1983-12-05 | 1985-06-04 | Xerox Corporation | Novel squarine systems |
-
1983
- 1983-12-16 JP JP58236203A patent/JPS60130558A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60130558A (en) | 1985-07-12 |
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