JPS5829298B2 - photosensitive compound - Google Patents
photosensitive compoundInfo
- Publication number
- JPS5829298B2 JPS5829298B2 JP15720980A JP15720980A JPS5829298B2 JP S5829298 B2 JPS5829298 B2 JP S5829298B2 JP 15720980 A JP15720980 A JP 15720980A JP 15720980 A JP15720980 A JP 15720980A JP S5829298 B2 JPS5829298 B2 JP S5829298B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- photosensitive compound
- photosensitive
- compound
- solvent
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Description
【発明の詳細な説明】
本発明は、写真・印刷工業あるいは電子工業等で画像を
形成するために有用な感光性樹脂に使用される下記式（
Ｉ）で示される新規な感光性化合物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a photosensitive resin of the following formula (
The present invention relates to a novel photosensitive compound represented by I).
感光性樹脂を形成させるために用いられる感光性化合物
として種々の有機化合物が合成されており、アジド基含
有の化合物も多くの文献に見られる。Various organic compounds have been synthesized as photosensitive compounds used to form photosensitive resins, and azide group-containing compounds are also found in many documents.
例えば、本発明者らによる特許第７２７５２４．７４４
９８６．７７５８１３号等があり、本発明の化合物は、
その後、さらに鋭意研究の結果見出されたものである。For example, patent number 727524.744 by the present inventors
No. 986.775813, etc., and the compound of the present invention is
This was discovered as a result of further intensive research.
すなわち既に提案された感光性化合物に比べて分光感度
が異なり、特に３００〜４０．０Ｈｍの領域で高い感度
を有する。That is, the spectral sensitivity is different from that of previously proposed photosensitive compounds, and it has particularly high sensitivity in the range of 300 to 40.0 Hm.
また、増感剤を組合わせることにより、さらに長波長部
すなわち広域な可視光部においても感光させることが可
能である。Furthermore, by combining a sensitizer, it is possible to sensitize even longer wavelength regions, that is, wider visible light regions.
それゆえに、本発明の化合物に対して適切な光源として
は、水銀灯、ケミカルランプのみならず、キセノン灯、
ハロゲン灯、タングステン灯、あるいは太陽光も用いる
ことができ、本発明の化合物はこれらの光源に対しても
充分な感度を有するもので、新しい用途も期待される。Therefore, suitable light sources for the compounds of the present invention include not only mercury lamps and chemical lamps, but also xenon lamps,
Halogen lamps, tungsten lamps, or sunlight can also be used, and the compounds of the present invention have sufficient sensitivity to these light sources, and new applications are expected.
本発明の感光性化合物の製造原料は４・４／−ジヒドロ
キシベンゾフェノン及びバラアジドケイ皮酸であるが、
これは一般化学工業原料から容易に合成されるものであ
り、安価に容易に入手できる。The raw materials for producing the photosensitive compound of the present invention are 4,4/-dihydroxybenzophenone and baraazidocinnamic acid.
This is easily synthesized from general chemical industrial raw materials and is easily available at low cost.
さらに、これらからの製法も非常に容易で、収率良く得
られる。Furthermore, the production method from these is also very easy and can be obtained in good yield.
すなわち、本発明の化合物は、式で表わされる４・４′
−ジヒドロキシベンゾフェノンを式
で表わされるバラアジドケイ皮酸又はその誘導体の２倍
量と縮合させることによって製造される。That is, the compound of the present invention has 4.4' represented by the formula
- prepared by condensing dihydroxybenzophenone with twice the amount of baraazidocinnamic acid or a derivative thereof of the formula.
本発明の感光性化合物を感光性樹脂の形で使用するには
、高分子化合物、例えば、溶剤可溶性の天然コム、環化
ゴムなどの変性ゴム、スチレン・ブタジェンゴム、ポリ
クロロプレン、ニトリルゴム等の合成ゴムなどを溶解し
た液に、本発明の感光性化合物を微量、例えば、ｏ、ｉ
〜１０重量％含有させればよい。In order to use the photosensitive compound of the present invention in the form of a photosensitive resin, polymer compounds such as solvent-soluble natural combs, modified rubbers such as cyclized rubber, styrene-butadiene rubber, polychloroprene, nitrile rubber, etc. Add a small amount of the photosensitive compound of the present invention to a solution containing rubber or the like, for example, o, i
It is sufficient to contain up to 10% by weight.
この感光性樹脂液を基板上に塗膜し、目的の画像に応じ
て光照射し、溶剤によって現像し、露光部が溶剤に不溶
化され、画像が形成されるものである。This photosensitive resin liquid is coated on a substrate, irradiated with light according to the desired image, and developed with a solvent, so that the exposed areas are insolubilized in the solvent and an image is formed.
以下、実施例により、本発明の感光性化合物の製造方法
及びその使用方法の詳細を説明する。Hereinafter, details of the method for producing the photosensitive compound of the present invention and the method for using the same will be explained with reference to Examples.
実施例 １
本発明の感光性化合物の原料として４・４／−ジヒドロ
キシベンゾフェノンとバラアジドケイ皮酸クロライドを
用意する。Example 1 4.4/-dihydroxybenzophenone and baraazidocinnamic acid chloride are prepared as raw materials for the photosensitive compound of the present invention.
前者は化学工業中間体として製造されており、後者は本
発明者らによる文献（Ｊ、Ｐｏｌｙｍｅｒ Ｓｃｉ 、
Ａ−１、縛、２３７９（１９７２））、に基づいて、
バラニトロケイ皮酸から容易に合成される。The former is produced as a chemical industrial intermediate, and the latter is described in the literature by the present inventors (J, Polymer Sci,
Based on A-1, Taku, 2379 (1972)),
Easily synthesized from varanitrocinnamic acid.
４・４′−ジヒドロキシベンゾフェノン１．５１とバラ
アジドケイ皮酸クロライド３グとを乾燥したピリジン１
００ｒｒＬｌに溶解させ、約６０℃にて６時間攪拌する
。1.51 of 4,4'-dihydroxybenzophenone and 3 g of baraazidocinnamic acid chloride are dried in pyridine 1
00rrLl and stirred at about 60°C for 6 hours.
反応液から減圧にてピリジンを留出除去し、アセトン、
エーテル混合液から目的の縮合化合物式（Ｉ）を取り出
す。Pyridine was distilled off from the reaction solution under reduced pressure, and acetone,
The target condensed compound formula (I) is taken out from the ether mixture.
黄色結晶、収量１，５り。赤外線吸収スペクトル：２１
４０．１７３０、１６４０、１５９５ＣｒｒＬ−１、そ
の他。Yellow crystals, yield 1.5 ml. Infrared absorption spectrum: 21
40.1730, 1640, 1595CrrL-1, and others.
紫外線吸収スペクトル：極大吸収３２０ｎｍ、吸収最長
波長端約４５０ｎｒｒＬ。Ultraviolet absorption spectrum: maximum absorption 320 nm, longest absorption wavelength approximately 450 nrrL.
参考例 １
環化ゴム２１と実施例１で得た結晶ｏ、ｉｙをトルエン
５０ｍ１．クロルベンゼン３０１ｒＬｌ、テトラヒドロ
フラン２０ｍ１の混合溶剤中に溶解させる。Reference Example 1 Cyclized rubber 21 and the crystals o and iy obtained in Example 1 were mixed with 50 ml of toluene. Dissolve in a mixed solvent of 301 rL of chlorobenzene and 20 ml of tetrahydrofuran.
この液をガラス板上に塗布、乾燥させて、５００Ｗ高圧
水銀灯からの光を２０秒間照射する。This liquid is applied onto a glass plate, dried, and irradiated with light from a 500 W high-pressure mercury lamp for 20 seconds.
露光したガラス板をトルエン、クロルベンゼン混合液中
に浸漬させ、未露光部を溶解させる。The exposed glass plate is immersed in a mixture of toluene and chlorobenzene to dissolve the unexposed areas.
露光部は溶剤に不溶の硬化した膜を与えた。The exposed areas provided a cured film that was insoluble in the solvent.
参考例 ２
スチレン・ブタジェンゴム２１と実施例１で得た結晶０
．ＩＰ、チオミヒラーズケトン０．２！／をトルエン５
０ｍ１１クロルベンゼン２０ｍ１． メチルエチルケト
ン３０ＴｒＬｌの混合溶剤中に溶解させる。Reference example 2 Styrene-butadiene rubber 21 and crystals obtained in Example 1 0
．． IP, Thiomihiraz Ketone 0.2! / toluene 5
0m11 Chlorobenzene 20m1. Dissolve in a mixed solvent of 30 TrLl of methyl ethyl ketone.
この液をガラス板上に塗布、乾燥させて、２にＷ高圧キ
セノン灯からの光を２０秒間照射する。This liquid was applied onto a glass plate, dried, and 2 was irradiated with light from a W high-pressure xenon lamp for 20 seconds.
露光したガラス板を、トルエン、クロルベンゼン、メチ
ルエチルケトン混合溶剤中に浸漬させ、未露光部を溶解
させる。The exposed glass plate is immersed in a mixed solvent of toluene, chlorobenzene, and methyl ethyl ketone to dissolve the unexposed areas.
露光部は溶剤に不溶の硬化した膜を与えた。The exposed areas provided a cured film that was insoluble in the solvent.
図は、本発明の赤外吸収スペクトルを示す。 The figure shows an infrared absorption spectrum of the present invention.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15720980A JPS5829298B2 (en) | 1980-11-07 | 1980-11-07 | photosensitive compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15720980A JPS5829298B2 (en) | 1980-11-07 | 1980-11-07 | photosensitive compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5780356A JPS5780356A (en) | 1982-05-19 |
| JPS5829298B2 true JPS5829298B2 (en) | 1983-06-22 |
Family
ID=15644587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15720980A Expired JPS5829298B2 (en) | 1980-11-07 | 1980-11-07 | photosensitive compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5829298B2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5138089A (en) * | 1986-06-27 | 1992-08-11 | The Procter & Gamble Company | Chromophores, sunscreen compositions and methods for preventing sunburn |
| US5243064A (en) * | 1986-06-27 | 1993-09-07 | The Procter & Gamble Company | Chromophores, sunscreen compositions and methods for preventing sunburn |
| US4937370A (en) * | 1987-06-02 | 1990-06-26 | The Procter & Gamble Company | Novel chromophores, sunscreen compositions and methods for preventing sunburn |
| US5229106A (en) * | 1986-06-27 | 1993-07-20 | The Procter & Gamble Company | Sunscreen agents, sunscreen compositions and method for preventing sunburn |
| US5229107A (en) * | 1986-06-27 | 1993-07-20 | The Procter & Gamble Company | Sunscreen agents, sunscreen compositions and methods for preventing sunburn |
| US5230874A (en) * | 1986-06-27 | 1993-07-27 | The Procter & Gamble Company | Sunscreen agents, sunscreen compositions and methods for preventing sunburn |
-
1980
- 1980-11-07 JP JP15720980A patent/JPS5829298B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5780356A (en) | 1982-05-19 |
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