JPH0250099B2 - - Google Patents
Info
- Publication number
- JPH0250099B2 JPH0250099B2 JP10477984A JP10477984A JPH0250099B2 JP H0250099 B2 JPH0250099 B2 JP H0250099B2 JP 10477984 A JP10477984 A JP 10477984A JP 10477984 A JP10477984 A JP 10477984A JP H0250099 B2 JPH0250099 B2 JP H0250099B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- hydrogen
- represents hydrogen
- fluorine
- 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
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 150000001448 anilines Chemical class 0.000 claims description 9
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical class CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 11
- 206010034972 Photosensitivity reaction Diseases 0.000 description 7
- 230000036211 photosensitivity Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 108091008695 photoreceptors Proteins 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 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 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- FBGJJTQNZVNEQU-UHFFFAOYSA-N n,3-dimethylaniline Chemical compound CNC1=CC=CC(C)=C1 FBGJJTQNZVNEQU-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- XDEPVFFKOVDUNO-UHFFFAOYSA-N pentafluorobenzyl bromide Chemical compound FC1=C(F)C(F)=C(CBr)C(F)=C1F XDEPVFFKOVDUNO-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- AEQDJSLRWYMAQI-KRWDZBQOSA-N tetrahydropalmatine Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3C[C@H]2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-KRWDZBQOSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
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
して有用なスクエアリウム化合物の合成原料であ
る新規なアニリン誘導体およびその製造方法に関
する。
従来技術
従来、電子写真用感光体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、CaSe、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
たつてフラツトな光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
つかつていなかつた。しかし本発明者が鋭意検討
の結果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
ム化合物を見出した。
発明の目的
本発明の目的は電子写真用感光体の電荷発生物
質として有用なスクエアリウム化合物の合成原料
である新規なアニリン誘導体を提供することにあ
る。
発明の構成
本発明は第１の対象は一般式（）
で示されるアニリン誘導体である。
上記式中、X1はフツ素、ニトロ基、カルボキ
シル基またはエトキシカルボニル基を表わした、
X2は水素またはフツ素を表わし、Ｙは水素また
はメチル基を表わす。但しX1がニトロ基で、か
つX2が水素を表わす場合にはＹは水素でないも
のとする。本発明の第２の対象は式（）
（式中、Ｙは前記と同じ意味を表わす。）
で示されるＮ−メチルアニリン誘導体と式（）
（式中、X1およびX2は前記と同じ意味を表わ
す。）
で示される前記一般式（）で示される新規なア
ニリン誘導体の製造方法である。
前記の新規なアニリン誘導体は、式（）のＮ
−メチルアニリン誘導体と式（）の置換ベンジ
ルブロマイドとをＮ−メチルアニリン誘導体の過
剰または適当な塩基の存在下溶媒（たとえばトル
エン）中で0.2〜３時間100〜120℃にて反応させ、
冷却後分離精製を行うことにより得られる。
この様にして得られる本発明の新規なアニリン
誘導体の具体例を構造式で表１に示す。
INDUSTRIAL APPLICATION FIELD The present invention relates to a novel aniline derivative that is a raw material for synthesizing a squarium compound useful as a charge generating material for electrophotographic photoreceptors, and a method for producing the same. BACKGROUND OF THE INVENTION Conventionally, many substances have been known as electrophotographic photoreceptor materials. Among these, there are Se/Te, Se/As, CaSe, and phthalocyanine compounds that exhibit photosensitivity in the long wavelength range. Of these, Se/
Inorganic compounds such as Te have many problems such as it is difficult to obtain a photoreceptor with flat photosensitivity from the visible region to the near-infrared region, and it is difficult to process them into a belt shape due to their lack of flexibility. There is a point. In addition, phthalocyanine compounds, which are organic compounds,
Problems include low photosensitivity below 550 nm and difficulty in purification, and no practical substance has yet been found that exhibits flat photosensitivity from the visible to near-infrared regions. However, as a result of intensive studies, the present inventors have discovered a new squarium compound that has a flat photosensitivity over the entire wavelength range from the visible region to the near-infrared region. OBJECTS OF THE INVENTION An object of the present invention is to provide a novel aniline derivative that is a raw material for the synthesis of squarium compounds useful as charge-generating materials for electrophotographic photoreceptors. Structure of the Invention The first object of the present invention is the general formula () This is an aniline derivative represented by In the above formula, X 1 represents fluorine, a nitro group, a carboxyl group or an ethoxycarbonyl group,
X 2 represents hydrogen or fluorine, and Y represents hydrogen or a methyl group. However, when X 1 is a nitro group and X 2 represents hydrogen, Y is not hydrogen. The second object of the present invention is the expression () (In the formula, Y represents the same meaning as above.) N-methylaniline derivative represented by the formula () (In the formula, X 1 and X 2 have the same meanings as above.) This is a method for producing a novel aniline derivative represented by the general formula (). The above-mentioned novel aniline derivative has N of formula ()
- reacting a methylaniline derivative with a substituted benzyl bromide of formula () in an excess of the N-methylaniline derivative or in the presence of a suitable base in a solvent (e.g. toluene) for 0.2 to 3 hours at 100 to 120°C;
It is obtained by performing separation and purification after cooling. Specific examples of the novel aniline derivatives of the present invention obtained in this manner are shown in Table 1 in terms of structural formulas.
【表】【table】
【表】
発明の効果
本発明により得られる新規なアニリン誘導体と
３，４−ジヒドロキシ−３−シクロブテン−１，
２−ジオンとから合成される新規なスクエアリウ
ム化合物は電子写真用感光材料として有用であ
る。すなわち、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
通常の電子写真用複写機のみならず、半導体レー
ザー用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。
次に本発明の実施例を説明する。
実施例１ 化合物(4)の製造
Ｎ，３−ジメチルアニリン20.43ｇと２，３，
４，５，６−ペンタフルオロベンジルブロマイド
20.00ｇとをトルエン中で30分間還流し、析出し
た白色結晶を別した。液を水洗し、硫酸マグ
ネシウムで乾燥後溶媒を留去した。得られた白色
固体をメタノールで再結晶して白色針状の表題化
合物(4)の結晶を21.27ｇ（92％）得た。
mp：71〜72.5゜。
元素分析：
計算値(%) 実測値(%)
Ｃ 59.80 60.01
Ｈ 4.02 3.98
Ｎ 4.65 4.49
実施例 ２〜５
化合物(1)、(2)、(3)及び(5)も対応するＮ−メチル
アニリン誘導体と置換ベンジルブロマイドとから
実施例１と同様の反応により得られた。
化合物 (1)
mp：146〜147℃。
元素分析：
計算値(%) 実測値(%)
Ｃ 74.67 74.49
Ｈ 6.27 6.11
Ｎ 5.80 5.92
化合物 (2)
bp：145゜／0.6mmHg。
元素分析：
計算値(%) 実測値(%)
Ｃ 75.81 75.93
Ｈ 7.11 7.08
Ｎ 5.20 5.14
化合物 (3)
bp：174〜175℃／0.095mmHg。
元素分析：
計算値(%) 実測値(%)
Ｃ 70.29 70.14
Ｈ 6.29 6.35
Ｎ 10.93 10.79
化合物 (5)
mp：42〜43.5℃。
元素分析：
計算値(%) 実測値(%)
Ｃ 58.54 58.69
Ｈ 3.51 3.48
Ｎ 4.88 4.77[Table] Effects of the invention New aniline derivatives obtained by the present invention and 3,4-dihydroxy-3-cyclobutene-1,
A novel squarium compound synthesized from 2-dione is useful as a light-sensitive material for electrophotography. That is, 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 can be widely used as an intelligent copier. 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. Next, examples of the present invention will be described. Example 1 Production of compound (4) 20.43 g of N,3-dimethylaniline and 2,3,
4,5,6-pentafluorobenzyl bromide
20.00 g was refluxed in toluene for 30 minutes, and the precipitated white crystals were separated. The liquid was washed with water, dried over magnesium sulfate, and then the solvent was distilled off. The obtained white solid was recrystallized from methanol to obtain 21.27 g (92%) of white needle-like crystals of the title compound (4). mp: 71~72.5°. Elemental analysis: Calculated value (%) Actual value (%) C 59.80 60.01 H 4.02 3.98 N 4.65 4.49 Examples 2 to 5 Compounds (1), (2), (3) and (5) also correspond to N-methylaniline It was obtained by the same reaction as in Example 1 from the derivative and substituted benzyl bromide. Compound (1) mp: 146-147°C. Elemental analysis: Calculated value (%) Actual value (%) C 74.67 74.49 H 6.27 6.11 N 5.80 5.92 Compound (2) bp: 145°/0.6mmHg. Elemental analysis: Calculated value (%) Actual value (%) C 75.81 75.93 H 7.11 7.08 N 5.20 5.14 Compound (3) bp: 174-175°C/0.095mmHg. Elemental analysis: Calculated value (%) Actual value (%) C 70.29 70.14 H 6.29 6.35 N 10.93 10.79 Compound (5) mp: 42-43.5°C. Elemental analysis: Calculated value (%) Actual value (%) C 58.54 58.69 H 3.51 3.48 N 4.88 4.77
Claims (1)
ル基またはエトキシカルボニル基を表わし、X2
は水素またはフツ素を表わし、Ｙは水素またはメ
チル基を表わす。但しX1がニトロ基で、かつX2
が水素を表わす場合にはＹは水素ではないものと
する。） で示されるアニリン誘導体。 ２ 式（） （式中、Ｙは水素またはメチル基を表わす。） で示されるＮ−メチルアニリン誘導体と式（） （式中、X1はフツ素、ニトロ基、カルボキシ
ル基またはエトキシカルボニル基を表わし、X2
は水素または水素を表わす。 で示される置換ベンジルブロマイドとを反応させ
ることを特徴とする一般式（） （式中、X1、X2およびＹは前記と同じ意味を
表わす。但しX1がニトロ基で、かつX2が水素を
表わす場合にはＹは水素ではないものとする。） で示されるアニリン誘導体の製造方法。[Claims] 1 General formula () (In the formula, X 1 represents fluorine, a nitro group, a carboxyl group or an ethoxycarbonyl group, and X 2
represents hydrogen or fluorine, and Y represents hydrogen or a methyl group. However, X 1 is a nitro group, and X 2
When represents hydrogen, Y is not hydrogen. ) Aniline derivatives shown as 2 formula () (In the formula, Y represents hydrogen or a methyl group.) N-methylaniline derivative represented by the formula () (In the formula, X 1 represents fluorine, a nitro group, a carboxyl group or an ethoxycarbonyl group, and X 2
represents hydrogen or hydrogen. General formula () characterized by reacting with a substituted benzyl bromide represented by (In the formula, X 1 , X 2 and Y have the same meanings as above. However, when X 1 is a nitro group and X 2 represents hydrogen, Y is not hydrogen.) A method for producing an aniline derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10477984A JPS60260545A (en) | 1984-05-25 | 1984-05-25 | Novel aniline derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10477984A JPS60260545A (en) | 1984-05-25 | 1984-05-25 | Novel aniline derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60260545A JPS60260545A (en) | 1985-12-23 |
| JPH0250099B2 true JPH0250099B2 (en) | 1990-11-01 |
Family
ID=14389958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10477984A Granted JPS60260545A (en) | 1984-05-25 | 1984-05-25 | Novel aniline derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60260545A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3741357A1 (en) * | 1987-12-07 | 1989-06-15 | Buchholz Elaplan Kg | DEVICE FOR CREATING AN OFFSET FILM OR A FILM DOCUMENT FOR EXPOSING AN OFFSET PRINTING PLATE |
| EP0507488A1 (en) * | 1991-03-27 | 1992-10-07 | Merck & Co. Inc. | Inhibitors of HIV-1 reverse transcriptase |
-
1984
- 1984-05-25 JP JP10477984A patent/JPS60260545A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60260545A (en) | 1985-12-23 |
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