JPH0344587B2 - - Google Patents
Info
- Publication number
- JPH0344587B2 JPH0344587B2 JP58239815A JP23981583A JPH0344587B2 JP H0344587 B2 JPH0344587 B2 JP H0344587B2 JP 58239815 A JP58239815 A JP 58239815A JP 23981583 A JP23981583 A JP 23981583A JP H0344587 B2 JPH0344587 B2 JP H0344587B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- squarium
- general formula
- represented
- 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
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 7
- 230000036211 photosensitivity Effects 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108091008695 photoreceptors Proteins 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VIIZJXNVVJKISZ-UHFFFAOYSA-N 2-(n-methylanilino)ethanol Chemical compound OCCN(C)C1=CC=CC=C1 VIIZJXNVVJKISZ-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- -1 Se/Te Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WVHYFUMRIFQFNH-UHFFFAOYSA-N cyclobutene-1,2-diol Chemical compound OC1=C(O)CC1 WVHYFUMRIFQFNH-UHFFFAOYSA-N 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 description 1
- 239000000049 pigment Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 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
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。
従来、電子写真用感光体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
の取り扱い、特に廃棄には注意を要するととも
に、製造がむずかしく、製造コストが高い、可撓
性がなく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、有機化合物として
はフタロシアニン化合物があり、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
（）で示されるスクエアリウム化合物である。
（式中、Ｘは水酸基、メトキシ基又はハロゲン
原子を表わす。）
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（以下スクエアリツクシツ
ドと呼ぶ。）と一般式（）
（式中、Ｘ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
ツクア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℃にて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を構造式で以下の表１に示
す。
The present invention relates to a novel squarium compound that has photosensitivity over a wavelength range from visible to near infrared and is used as a charge generating material for electrophotographic photoreceptors, and a method for producing the same. Conventionally, many substances have been known as materials for electrophotographic photoreceptors. Among these, 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 require special care when handling, especially when disposing of them. They are also difficult to manufacture, have high manufacturing costs, and are inflexible and cannot be processed into belts. There are many problems such as difficulty in In addition, phthalocyanine compounds are organic compounds, which are non-toxic and inexpensive, but they have problems such as low photosensitivity below 550 nm and difficulty in purification, and they are difficult to purify from the visible region to the near-infrared region. No practical material has yet been found that exhibits flat photosensitivity. 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 squarium compound represented by the following general formula (). (In the formula, X represents a hydroxyl group, a methoxy group, or a halogen atom.) The second object of the present invention is the formula () 3,4-dihydroxy-3-cyclobutene-1,2-dione (hereinafter referred to as square oxide) represented by the general formula () (In the formula, X represents the same meaning as above.) This is a method for producing the novel squarium compound, characterized by reacting it with an aniline derivative represented by the following. The novel squarium compound described above combines squarium acid and an aniline derivative with a solvent (e.g.
n-butanol or amyl alcohol) at 120 to 140°C for 3 to 5 hours. After washing, the obtained compound is further purified by recrystallization from an appropriate solvent. 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.
【表】【table】
【表】
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、全可視域及び近赤外
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
ンテリジエントコピア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
どの光学記録媒体としてや有機太陽電池など様々
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−ヒドロキシエチル−Ｎ−メチル−アニリン
5.3ｇと33，４−ジヒドロキシ−３−シクロブテ
ン1.0ｇをｎ−ブタノール35ml中に加え、撹拌し
ながら、120〜130℃で、5.5時間加熱した。冷却
後析出した青緑色の結晶を過し、メタノールで
洗浄後、クロロエタノールから再結晶し、乾燥し
て、目的物のスクエアリウム色素を1.3ｇ（38.0
％）得た。
分解点：260℃。
赤外線吸収スペクトル（KBr錠剤法）：
νOH＝3370cm-1
νC＝Ｏ＝1590cm-1。
元素分析： 実測値 理論値
Ｃ 69.26％ 69.46％
Ｈ 6.40％ 6.36％
Ｎ 7.21％ 7.36％
可視吸収スペクトル：
λnax＝633nm（ジクロメタン溶液中）。
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２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３に元素分析の
結果を示した。[Table] 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 as an ordinary electrophotographic copying machine but also as a semiconductor laser printer, and is widely used as an intelligent copier. Furthermore, in addition to the field of electrophotography, various applications are possible, such as as optical recording media such as laser disks and organic solar cells. Next, the present invention will be explained by examples. Example 1 Production of compound (1) N-hydroxyethyl-N-methyl-aniline
5.3 g and 1.0 g of 33,4-dihydroxy-3-cyclobutene were added to 35 ml of n-butanol and heated at 120-130° C. for 5.5 hours with stirring. After cooling, the precipitated blue-green crystals were filtered, washed with methanol, recrystallized from chloroethanol, and dried to obtain 1.3 g (38.0 g) of the target squarium pigment.
%)Obtained. Decomposition point: 260℃. Infrared absorption spectrum (KBr tablet method): νOH = 3370 cm -1 νC = O = 1590 cm -1 . Elemental analysis: Actual value Theoretical value C 69.26% 69.46% H 6.40% 6.36% N 7.21% 7.36% Visible absorption spectrum: λ nax = 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 2 shows the decomposition point, infrared absorption spectrum, and visible absorption spectrum of each compound produced, and Table 3 shows the results of elemental analysis.
【表】【table】
【表】【table】
【表】【table】
Claims (1)
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−ジオンと一般式（） （式中、Ｘは水酸基、メトキシ基又はハロゲン
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 hydroxyl group, a methoxy group, or a halogen atom.) A squarium compound represented by the following. 2 formula () 3,4-dihydroxy-3-cyclobutene-1,2-dione represented by the general formula () (In the formula, X represents a hydroxyl group, a methoxy group, or a halogen atom.) General formula () characterized by reacting with an aniline derivative represented by (In the formula, X represents the same meaning as above.) A method for producing a squarium compound represented by the following.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58239815A JPS60132945A (en) | 1983-12-21 | 1983-12-21 | Novel squarylium compound and its preparation |
| US06/682,211 US4700001A (en) | 1983-12-16 | 1984-12-17 | Novel squarylium compound and photoreceptor containing same |
| US06/946,641 US4707427A (en) | 1983-12-16 | 1986-12-29 | Squarylium compound in an electrophotographic element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58239815A JPS60132945A (en) | 1983-12-21 | 1983-12-21 | Novel squarylium compound and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60132945A JPS60132945A (en) | 1985-07-16 |
| JPH0344587B2 true JPH0344587B2 (en) | 1991-07-08 |
Family
ID=17050257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58239815A Granted JPS60132945A (en) | 1983-12-16 | 1983-12-21 | Novel squarylium compound and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60132945A (en) |
-
1983
- 1983-12-21 JP JP58239815A patent/JPS60132945A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60132945A (en) | 1985-07-16 |
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