JPH07107029B2 - Novel squarylium compound and method for producing the same - Google Patents
Novel squarylium compound and method for producing the sameInfo
- Publication number
- JPH07107029B2 JPH07107029B2 JP62305859A JP30585987A JPH07107029B2 JP H07107029 B2 JPH07107029 B2 JP H07107029B2 JP 62305859 A JP62305859 A JP 62305859A JP 30585987 A JP30585987 A JP 30585987A JP H07107029 B2 JPH07107029 B2 JP H07107029B2
- Authority
- JP
- Japan
- Prior art keywords
- squarylium compound
- producing
- same
- structural formula
- novel
- 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 - Fee Related
Links
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
- G03G5/0611—Squaric acid
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
Landscapes
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (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、新規なスクアリリウム化合物及びその製造方
法に関する。TECHNICAL FIELD The present invention relates to a novel squarylium compound and a method for producing the same.
従来の技術 従来、電子写真感光体に使用する感光材料については種
々のものが知られているが、近年有機系感光材料を用い
た電子写真感光体が注目され、種々検討されている。有
機系の光導電材料としては、ビスアゾ系顔料、トリスア
ゾ系顔料、フタロシアニン系顔料、シアニン類、ピリリ
ウム類等が知られており、又、近年ある種のスクアリリ
ウム化合物が優れた光導電特性を示し、電子写真感光材
料として使用できることが報告されている（例えば特開
昭60−136542号公報、同60−142946号公報、同60−1429
47号公報、同61−10540号公報、同62−450号公報等参
照）。2. Description of the Related Art Conventionally, various photosensitive materials used for electrophotographic photosensitive members have been known, but in recent years, electrophotographic photosensitive members using an organic photosensitive material have attracted attention and various studies have been made. As the organic photoconductive material, bisazo-based pigments, trisazo-based pigments, phthalocyanine-based pigments, cyanines, pyryliums and the like are known, and in recent years, some squarylium compounds exhibit excellent photoconductive properties, It has been reported that it can be used as an electrophotographic light-sensitive material (for example, JP-A-60-136542, JP-A-60-142946, and JP-A-60-1429).
47, 61-10540, 62-450, etc.).
発明が解決しようとする問題点 従来提案されている種々の有機化合物は、電子写真感光
体において、電荷発生剤として利用できるが、更に他の
優れた電荷発生剤を提供することが望まれている。Problems to be Solved by the Invention Various conventionally proposed organic compounds can be used as charge generating agents in electrophotographic photoreceptors, but it is desired to provide further excellent charge generating agents. .
本発明者等は、一群のスクアリリウム化合物について検
討した結果、以下に示す新規なスクアリリウム化合物が
電荷発生剤として有用であることを見出だし、本発明を
完成するに至った。As a result of examining a group of squarylium compounds, the present inventors have found that the following novel squarylium compounds are useful as charge generating agents, and have completed the present invention.
したがって、本発明の目的は、電子写真感光体の電荷発
生剤として有用な新規なスクアリリウム化合物及びその
製造方法を提供することにある。Therefore, an object of the present invention is to provide a novel squarylium compound useful as a charge generating agent for an electrophotographic photoreceptor and a method for producing the same.
問題点を解決するための手段 本発明の新規なスクアリリウム化合物は、下記一般式
（Ｉ）で示される。Means for Solving Problems The novel squarylium compound of the present invention is represented by the following general formula (I).
上記一般式（Ｉ）で示されるスクアリリウム化合物は、
下記構造式（II） 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１モルと、下記構造式（III） で示されるアニリン誘導体２モルとを反応させることに
よって製造することができる。 The squarylium compound represented by the general formula (I) is
Structural formula (II) below 3,4-dihydroxy-3-cyclobutene-1,2 represented by
1 mol of dione and the following structural formula (III) It can be produced by reacting with 2 mol of the aniline derivative represented by.
上記の反応は、公知の類似の反応に準じて実施すること
ができる。The above reaction can be carried out according to a known similar reaction.
即ち、3,4−ジヒドロキシ−３−シクロブテン−1,2−ジ
オン１モルと、前記構造式（III）で示されるアニリン
誘導体２モルとを、適当な溶剤、例えば、ｎ−ブチルア
ルコール、ｎ−ヘプチルアルコール等の炭素数４〜８の
脂肪族アルコール、またはこれとベンゼン、トルエン等
の芳香族炭化水素との混合溶媒中で加熱することによっ
て行なうことができる。That is, 1 mol of 3,4-dihydroxy-3-cyclobutene-1,2-dione and 2 mol of the aniline derivative represented by the structural formula (III) were mixed with a suitable solvent such as n-butyl alcohol or n-butyl alcohol. It can be carried out by heating in an aliphatic alcohol having 4 to 8 carbon atoms such as heptyl alcohol or a mixed solvent of this and an aromatic hydrocarbon such as benzene and toluene.
本発明のスクアリリウム化合物は、電子写真感光体の電
荷発生剤として有用である。例えば、感光層が電荷発生
層と電荷輸送層とに機能分離された積層構造を有する場
合において、上記スクアリリウム化合物を成膜性の樹脂
と共に用いて電荷発生層を形成することができる。The squarylium compound of the present invention is useful as a charge generating agent for an electrophotographic photoreceptor. For example, when the photosensitive layer has a laminated structure in which the charge generation layer and the charge transport layer are functionally separated, the squarylium compound can be used together with a film-forming resin to form the charge generation layer.
実施例 ｍ−（N,N−ジフェニルアミノ）フェノール3.03g（11.6
ミリモル）と3,4−ジヒドロキシ−３−シクロブテン−
1,2−ジオン0.60g（5.3ミリモル）とをブタノール50ml
とトルエン25mlの混合溶媒中で3.5時間加熱還流した。
冷却後、析出した緑色結晶を濾過し、メタノール及びジ
エチルエーテルで洗浄して、目的とする構造式（Ｉ）で
示されるスクアリリウム化合物1.67g（収率53％）を得
た。融点:m.p.＝263℃（分解）。Example m- (N, N-diphenylamino) phenol 3.03 g (11.6
Mmol) and 3,4-dihydroxy-3-cyclobutene-
0.60 g (5.3 mmol) of 1,2-dione and 50 ml of butanol
The mixture was heated under reflux for 3.5 hours in a mixed solvent of 25 ml of toluene and toluene.
After cooling, the precipitated green crystals were filtered and washed with methanol and diethyl ether to obtain 1.67 g (yield 53%) of the target squarylium compound represented by the structural formula (I). Melting point: mp = 263 ° C (decomposition).
この化合物の赤外吸収スペクトルは第１図に示す通りで
あり、紫外吸収スペクトル（最大）は、UV（CH2Cl2）:6
77nmであった。又、元素分析値は、C40H28N2O4として、
次の通りであった。The infrared absorption spectrum of this compound is as shown in FIG. 1, and the ultraviolet absorption spectrum (maximum) is UV (CH 2 Cl 2 ): 6.
It was 77 nm. The elemental analysis value is C 40 H 28 N 2 O 4 ,
It was as follows.
計算値（％） 実測値（％） Ｃ 79.98 79.87 Ｈ 4.70 4.54 Ｎ 4.66 4.60 発明の効果 本発明のスクアリリウム化合物は、新規な化合物であ
り、電子写真感光体における電荷発生剤として有用な物
質であって、可視領域から近赤外領域までの広い範囲に
わたって感度を有する電子写真感光体を得ることができ
る。特に、電荷発生層と電荷輸送層とに機能分離された
積層構造を有する電子写真感光体において、電荷発生層
中に含有させると、良好な感度のものが得られる。Calculated value (%) Measured value (%) C 79.98 79.87 H 4.70 4.54 N 4.66 4.60 Effect of the Invention The squarylium compound of the present invention is a novel compound and is a useful substance as a charge generating agent in an electrophotographic photoreceptor. It is possible to obtain an electrophotographic photosensitive member having sensitivity over a wide range from the visible region to the near infrared region. In particular, in an electrophotographic photosensitive member having a laminated structure in which a charge generating layer and a charge transporting layer are functionally separated, when contained in the charge generating layer, excellent sensitivity can be obtained.
第１図は本発明のスクアリリウム化合物の赤外吸収スペ
クトル図である。FIG. 1 is an infrared absorption spectrum diagram of the squarylium compound of the present invention.
Claims (2)
−ジオンと、下記構造式（III） 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
する下記構造式（Ｉ） で示されるスクアリリウム化合物の製造方法。2. The following structural formula (II) 3,4-dihydroxy-3-cyclobutene-1,2 represented by
-Dione and the following structural formula (III) The following structural formula (I) is characterized by reacting with an aniline derivative represented by The manufacturing method of the squarylium compound shown by these.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62305859A JPH07107029B2 (en) | 1987-12-04 | 1987-12-04 | Novel squarylium compound and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62305859A JPH07107029B2 (en) | 1987-12-04 | 1987-12-04 | Novel squarylium compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01146845A JPH01146845A (en) | 1989-06-08 |
| JPH07107029B2 true JPH07107029B2 (en) | 1995-11-15 |
Family
ID=17950220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62305859A Expired - Fee Related JPH07107029B2 (en) | 1987-12-04 | 1987-12-04 | Novel squarylium compound and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07107029B2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2871181B2 (en) * | 1991-07-09 | 1999-03-17 | ブラザー工業株式会社 | Photocurable composition |
| JP3141517B2 (en) | 1992-05-14 | 2001-03-05 | ブラザー工業株式会社 | Photocurable composition |
| DE69330060T2 (en) * | 1992-10-26 | 2001-11-15 | Dainippon Printing Co Ltd | Photoelectric sensor, information recording system and method for information recording |
| JP3362745B2 (en) * | 1993-07-28 | 2003-01-07 | ブラザー工業株式会社 | Photosensitive microcapsule type toner |
| US20100065112A1 (en) | 2008-09-15 | 2010-03-18 | Thompson Mark E | Organic Photosensitive Devices Comprising a Squaraine Containing Organoheterojunction and Methods of Making Same |
| CN105037246A (en) * | 2011-02-09 | 2015-11-11 | 密歇根大学董事会 | Organic photosensitive devices comprising aryl squaraines and methods of making the same |
| WO2018008721A1 (en) * | 2016-07-08 | 2018-01-11 | コニカミノルタ株式会社 | Organic electroluminescent element, display device, and illumination device |
-
1987
- 1987-12-04 JP JP62305859A patent/JPH07107029B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01146845A (en) | 1989-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |