JPS6036504A - Production of photo-sensitive resin - Google Patents
Production of photo-sensitive resinInfo
- Publication number
- JPS6036504A JPS6036504A JP14589083A JP14589083A JPS6036504A JP S6036504 A JPS6036504 A JP S6036504A JP 14589083 A JP14589083 A JP 14589083A JP 14589083 A JP14589083 A JP 14589083A JP S6036504 A JPS6036504 A JP S6036504A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- chalcone
- carboxychalcone
- trinitrochlorobenzene
- 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.)
- Granted
Links
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は感光性樹脂の製法に関するものである。さらに
詳しくいえば本発明は、光架橋性基としてカルコン基ま
たはその誘導体基を拮つ感光性樹脂の製法に関するもの
である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a photosensitive resin. More specifically, the present invention relates to a method for producing a photosensitive resin having a chalcone group or a derivative group thereof as a photocrosslinkable group.
これまで、カルコンまたはその誘導体基を有する感光性
樹脂の合成はポリベンザルアセトフェノンにアルデヒド
を反応させる方法、ポリスチレンに桂皮酸クロライドを
フリーデル・クラフト反応させる方法などが知られてい
る。これらの方法では光架橋性基の高い置換率の感光性
樹脂は得られずこれに帰因して感度か低い。吏に従来の
合成法では反応時間を長く必要とし。Hitherto, known methods for synthesizing photosensitive resins having chalcone or derivative groups thereof include a method in which polybenzalacetophenone is reacted with an aldehyde, and a method in which polystyrene is reacted with cinnamic acid chloride in a Friedel-Crafts reaction. With these methods, it is not possible to obtain a photosensitive resin with a high substitution rate of photocrosslinkable groups, and as a result, the sensitivity is low. However, conventional synthesis methods require long reaction times.
ゲル化を生じるなどの問題点がある。There are problems such as gelation.
本発明者らは、このような従来の感光性樹脂の製法のも
つ欠点を克服すべ(鋭意研究を重ねた結果、一般式(1
)で表わされるカルフンまたはその誘導体を2.4.6
−トリニトロクロルベンゼンの存在下でアルコール性水
酸基をもつ重合体または共重合体に直接反応させること
に成功し2本発明をなすに至った。The present inventors aimed to overcome the drawbacks of the conventional photosensitive resin manufacturing method (as a result of extensive research, the general formula (1
) or its derivatives represented by 2.4.6
-We succeeded in directly reacting a polymer or copolymer having an alcoholic hydroxyl group in the presence of trinitrochlorobenzene, resulting in the completion of the present invention.
すなわち本1明はアルコール性水酸基をもつ重合体また
は共重合体に
一般式
(式中のRI、 R2,Rsは前記と同じ意味を示す)
で表わされるカルコン誘導体を有効量の2,4゜6−ト
リニトロクロルベンゼンの存在下で反応させることを特
徴とする。In other words, this invention specifies the general formula (RI, R2, and Rs in the formula have the same meanings as above) for a polymer or copolymer having an alcoholic hydroxyl group.
It is characterized in that the chalcone derivative represented by is reacted in the presence of an effective amount of 2,4°6-trinitrochlorobenzene.
一般式
(式中のR,、R2、Rs は前記と同じ意味を示す)
で表わされる基を有する感光性樹脂の製法を提供するも
のである。The present invention provides a method for producing a photosensitive resin having a group represented by the general formula (R, , R2, and Rs in the formula have the same meanings as above).
本発明に於て用いられるアルコール性水酸基をもつ重合
体または共重合体としてはボリビニルアルコール、ポリ
ヒドロキシエチルアクレート、ヒドロキシエチルアクリ
レート−スチレン共重合体、ヒドロキシエチルメタクリ
レート−メチルメタクリレート共重合体、ポリ−2−ヒ
ドロキシプロピルメタクリレート、ポリエチレンとポリ
ビニルアルコールの共重合体などを小げることが出来る
。また一般式(1)で表わされるカルコン誘導体として
は4−カルボキシカルコン、4−カルボキシカルコン、
4−シアノ−4=カルボキシカルコン、4−nプロピル
−3−カルボキシカルコン、4′−クロロ−2−hルホ
キシカルコン、4−二トロー4−カルボキシカルコン、
3−メチル−2−カルボキシカルコン。Polymers or copolymers with alcoholic hydroxyl groups used in the present invention include vorivinyl alcohol, polyhydroxyethyl acrylate, hydroxyethyl acrylate-styrene copolymer, hydroxyethyl methacrylate-methyl methacrylate copolymer, and polyvinyl alcohol. -2-Hydroxypropyl methacrylate, copolymer of polyethylene and polyvinyl alcohol, etc. can be reduced. In addition, the chalcone derivatives represented by the general formula (1) include 4-carboxychalcone, 4-carboxychalcone,
4-cyano-4=carboxychalcone, 4-n propyl-3-carboxychalcone, 4'-chloro-2-h sulfoxychalcone, 4-nitro-4-carboxychalcone,
3-Methyl-2-carboxychalcone.
4−メj・キシカルコン、3−メトキシカルボニル−4
−カルボキシカルコンなどを挙げることが出来る。また
本発明に使用される有機塩基としてはピリジン、トリエ
チルアミン、4−ジメチルアミノピリジン、1,4−ジ
゛アザビシクロ(2,2,2)オクタンなどを挙げるこ
とが出来る。4-Mej-xychalcone, 3-methoxycarbonyl-4
- Carboxychalcone, etc. can be mentioned. Examples of the organic base used in the present invention include pyridine, triethylamine, 4-dimethylaminopyridine, and 1,4-diazabicyclo(2,2,2)octane.
反応溶媒の例としてはN、N−ジメチルアセトアミド、
N、N−ジメチルホルムアミド、ジメチルスルホギシド
、ヘキサメチルポスホリックトリアミドなどを挙げるこ
とができる。反応温度は20℃から100℃の範囲が望
ましいがこれに限定されるものではない。この際のカル
コン誘導体と2.4.6−)リニトロクロルクロルベン
ゼンのモル比は1:1から1=1.5の範囲で選ばれる
。しかしこれに限定されるものではない。また必要に応
じて使用される有機塩基とカルコン誘導体のモル比は2
:1から5:1の範囲が望ましいがそれ以外であっても
よい。Examples of reaction solvents include N,N-dimethylacetamide,
Examples include N,N-dimethylformamide, dimethylsulfogide, hexamethylphosphoric triamide, and the like. The reaction temperature is preferably in the range of 20°C to 100°C, but is not limited thereto. In this case, the molar ratio of the chalcone derivative and 2.4.6-)linitrochlorochlorobenzene is selected in the range of 1:1 to 1=1.5. However, it is not limited to this. In addition, the molar ratio of the organic base and chalcone derivative used as necessary is 2.
:1 to 5:1 is desirable, but other values are also possible.
反応生成物は反応混合液を水に注油することにより得ら
れる。The reaction product is obtained by pouring the reaction mixture into water.
本発明によって提供される感光性樹脂はこの有効量を有
機溶剤に溶解して溶液となし、アルミニウム板、銅板、
亜鉛板、銅張り積層板などの支持体表面上に、流延、吹
付け、塗布などの手段で施し、乾燥して製膜することが
できる。The photosensitive resin provided by the present invention can be prepared by dissolving this effective amount in an organic solvent to form a solution, which can be applied to aluminum plates, copper plates, etc.
It can be applied onto the surface of a support such as a zinc plate or a copper-clad laminate by means such as casting, spraying, or coating, and then dried to form a film.
このようにして得られる感光性膜は基体とする高分子の
物性を受継ぎ2強靭であり、かつ支持体との密着性かよ
い。このようにして得られた塗膜にネカを通して光照射
を行い、未露光部を溶剤で除去すると陰画像が得られる
。そして感度が極めて高くまた化学的に安定でいわゆる
暗反応が起こらないために溶液状態および製膜状態での
品質維持が容易である。そのためにフォトレジスト、印
刷用PSJk、金属エツチングマスクなどの用途に好適
である。The photosensitive film thus obtained inherits the physical properties of the polymer used as the base, is strong, and has good adhesion to the support. When the coating film thus obtained is irradiated with light through a negative lens and the unexposed areas are removed with a solvent, a negative image is obtained. Furthermore, since it has extremely high sensitivity, is chemically stable, and does not cause so-called dark reactions, it is easy to maintain quality in the solution state and film forming state. Therefore, it is suitable for applications such as photoresist, printing PSJk, and metal etching mask.
次に本発明を実施例により訂細に説明する。Next, the present invention will be explained in detail using examples.
実施例1
−m合度14oo、ケン化度85%のポリビニルアルコ
ール1gをジメチルアセトアミド80m1 に溶解しこ
れに4−カルボキシカルコン7.44gと2.4.6−
トリニトロクロルベンセン7、30 g ヲ加え、さら
にピリジン12gを添加し80℃で4時間反応させる。Example 1 - 1 g of polyvinyl alcohol with a m content of 14oo and a saponification degree of 85% was dissolved in 80 ml of dimethylacetamide, and 7.44 g of 4-carboxychalcone and 2.4.6-
Add 7.30 g of trinitrochlorobenzene, further add 12 g of pyridine, and react at 80° C. for 4 hours.
次に得られた反応混合物を大過剰の水に注加して目的と
する感光性樹脂を単離する。エタノールで洗浄後。Next, the resulting reaction mixture is poured into a large excess of water to isolate the desired photosensitive resin. After washing with ethanol.
乾燥した。収量は2.71gであった。このものの紫外
線吸収スペクトルを調べたところ吸収極大は3101m
であり、これからカルコン基の導入率を調べたところ6
0%であった。さらに赤外線吸収スペクトルを調べたと
ころカルコン基に基づく吸収が15Q5cm−’+及び
1665cm”−’ に認められた。Dry. Yield was 2.71g. When we investigated the ultraviolet absorption spectrum of this substance, the absorption maximum was 3101m.
From this, we investigated the introduction rate of chalcone groups and found that 6
It was 0%. Furthermore, when the infrared absorption spectrum was examined, absorption based on chalcone groups was observed at 15Q5cm-'+ and 1665cm''-'.
実施例2
重合度1700.ケン化度85%のポリビニルアルコー
ル0.44gをジメチルアセトアミド40m1に溶解し
これに4′−〇プロピルー4−カルボキシカルコン3.
82gと2.4.6−ドリニトロクロルベンゼン3.2
1gを加え、さらにピリジン5.1gを添加し85℃で
2時間反応さぜる。次に得られた反応混合物を大過剰の
エタノールに注加して目的とする感光性樹脂を単離する
。エタノールで洗浄後、乾燥した。収量は2.12gで
あった。このものの紫外線吸収スペクトルを調べたとこ
ろ吸収極大は3 Q 5 nmであり、これからカルコ
ン基の導入率を調べたところ6796であった。さらに
赤外線吸収スペクトルを調べたところカルコン基に基づ
く吸収が1600 Cm−’ 、及び1650Cm−’
に認めら、れた。Example 2 Degree of polymerization 1700. 0.44 g of polyvinyl alcohol with a degree of saponification of 85% was dissolved in 40 ml of dimethylacetamide, and 3.
82 g and 2.4.6-dolinitrochlorobenzene 3.2
1 g of pyridine was added thereto, and further 5.1 g of pyridine was added, followed by reaction at 85° C. for 2 hours. Next, the obtained reaction mixture is poured into a large excess of ethanol to isolate the desired photosensitive resin. After washing with ethanol, it was dried. Yield was 2.12g. When the ultraviolet absorption spectrum of this product was examined, the absorption maximum was found to be 3 Q 5 nm, and when the introduction rate of chalcone groups was examined from this, it was found to be 6796. Further investigation of the infrared absorption spectrum revealed that the absorption based on chalcone groups was 1600 Cm-' and 1650 Cm-'
was recognized and received.
実施例3
重合度2000.ケン化度85%のポリビニルアルコー
ル044gをジメチルアセトアミド40m1 に溶解し
これに4−クロロ−4−カルボキシカルコン3.72g
と2.4.6−1リニトロクロルベンセン3.21gを
加え、サラ1ごピリジン51gを添加し80°Cで23
時間反応さぜる。次に得られた反応混合物を大過剰のエ
タノールに注加して目的とする感光性樹脂を単離する。Example 3 Degree of polymerization: 2000. Dissolve 044 g of polyvinyl alcohol with a degree of saponification of 85% in 40 ml of dimethylacetamide, and add 3.72 g of 4-chloro-4-carboxychalcone to this solution.
2.4.6-1 Add 3.21 g of linitrochlorobenzene, add 51 g of pyridine, and heat at 80°C for 23 hours.
Time reaction. Next, the obtained reaction mixture is poured into a large excess of ethanol to isolate the desired photosensitive resin.
エタノールで洗浄後、乾燥した。収量は2.55gであ
った。このものの紫外線吸収スペクトルを調べたところ
吸収極大は315 nmであり、これからカルコン基の
導入率を調べたところ76%であった。さらに赤外線吸
収スペクトルを調べたところカルコン基に基づく吸収が
1600 cm−’ r及び1665 cm−’に認め
られた。After washing with ethanol, it was dried. Yield was 2.55g. When the ultraviolet absorption spectrum of this product was examined, the absorption maximum was found to be 315 nm, and when the introduction rate of chalcone groups was examined from this, it was found to be 76%. Furthermore, when the infrared absorption spectrum was examined, absorption based on chalcone groups was observed at 1600 cm-'r and 1665 cm-'.
実施例4
重合度1700.ケン化度90%のポリビニルアルコー
ル0.25gをジメチルアセトアミド2 Q Tll
1に溶解しこれに45メチル−3−カルボキシカルコン
1.97gと2.4.6−)リニトロクロルベンゼン1
.83gを加え、さらにピリジン3.2gを添加し85
℃で4時間反応さぜる。次に得られた反応混合物を大過
剰のエタノールに注加して目的とする感光性樹脂を単離
する。エタノールで洗浄後2乾燥した。収量は0、92
gであった。このものの紫外線吸収スペクトルを調べ
たところ吸収極太は316 nmであり、これからカル
コン基の導入率を調べたところ59%であった。さらに
赤外線吸収スペクトルを調べたところカルコン基に基づ
く吸収が1605cm−’、及び16600m−’に認
められた。Example 4 Degree of polymerization 1700. 0.25 g of polyvinyl alcohol with a degree of saponification of 90% was mixed with dimethylacetamide 2 Q Tll
1 and 1.97 g of 45 methyl-3-carboxychalcone and 2.4.6-)linitrochlorobenzene 1
.. Add 83g and further add 3.2g of pyridine to make 85
Stir the reaction at ℃ for 4 hours. Next, the obtained reaction mixture is poured into a large excess of ethanol to isolate the desired photosensitive resin. After washing with ethanol, it was dried twice. Yield is 0.92
It was g. When the ultraviolet absorption spectrum of this product was examined, the absorption maximum was 316 nm, and when the introduction rate of chalcone groups was examined from this, it was 59%. Furthermore, when the infrared absorption spectrum was examined, absorption based on chalcone groups was observed at 1605 cm-' and 16600 m-'.
実施例5
重合度500.ケン化度85%のポリビニルアルコール
0.25gをジメチルスルホキシト゛20m1に溶解し
これに3−ニトロ−3−カルボキシカルフン219gと
2.4.6−トリニトロクロルベンゼン183gを加え
、さらにピリジン3.4gを添加し、70℃で25 ’
J6’ Ijt+反応さゼる。Example 5 Degree of polymerization: 500. 0.25 g of polyvinyl alcohol with a degree of saponification of 85% was dissolved in 20 ml of dimethyl sulfoxide, 219 g of 3-nitro-3-carboxycarbonate and 183 g of 2,4,6-trinitrochlorobenzene were added thereto, and 3.4 g of pyridine was added. and incubate for 25' at 70°C.
J6' Ijt+reaction occurs.
次に得られた反応混合物を大過剰のエタノールに注加し
て目的とする感光性樹脂を単離する。Next, the obtained reaction mixture is poured into a large excess of ethanol to isolate the desired photosensitive resin.
エタノールで洗浄後、乾燥した。収量は1.35gであ
った。このものの紫外線吸収スペクトルを調べたところ
吸収極大は320 nmであり。After washing with ethanol, it was dried. Yield was 1.35g. When the ultraviolet absorption spectrum of this material was examined, the maximum absorption was found to be 320 nm.
これからカルコン基の導入率を調べたところ70%であ
った。さらに赤外線吸収スペクトルを調べたところカル
コン基に基づく吸収が1600cm−’ 、及び168
5 Cm−’ K認められた。The introduction rate of chalcone groups was investigated and found to be 70%. Further investigation of the infrared absorption spectrum revealed that the absorption based on chalcone groups was 1600 cm-' and 168 cm-'.
5 Cm-'K was observed.
実施例6
重合度2100.ケン化度87%のポリビニルアルコー
ル0.25gをジメチルホルムアミド20m1に溶解し
これに2′−ニトロ−4−カルボキシカルコン2.19
gと2.4.6−)リニトロクロルベンゼン1.83g
を加え、さらにピリジン3.2gを添加し80℃で24
時間反応させる。次に得られた反応混合物を大過剰のエ
タノールに注加して目的とする感光性樹脂を単離する。Example 6 Degree of polymerization 2100. 0.25 g of polyvinyl alcohol with a degree of saponification of 87% was dissolved in 20 ml of dimethylformamide, and 2.19 g of 2'-nitro-4-carboxychalcone was added to the solution.
g and 2.4.6-) linitrochlorobenzene 1.83 g
and then 3.2 g of pyridine and heated at 80°C for 24 hours.
Allow time to react. Next, the obtained reaction mixture is poured into a large excess of ethanol to isolate the desired photosensitive resin.
エタノールで洗浄後、乾燥した。収量は1.28gであ
った。このものの紫外線吸収スペクトルを調べたところ
吸収極大は319 nmであり、これからカルコン基の
導入率を調べたところ68%であった。さらに赤外線吸
収スペクトルを調べたところカルコン基に基ずく吸収か
1600cm−’+及びl 585 cm−’ に認め
られた。またニトロ基に基ずく吸収が1560Cm″、
”1350 c−m−” ニ認?b ラレf、:、。After washing with ethanol, it was dried. Yield was 1.28g. When the ultraviolet absorption spectrum of this product was examined, the absorption maximum was found to be 319 nm, and when the introduction rate of chalcone groups was examined from this, it was 68%. Further examination of the infrared absorption spectrum revealed absorption based on chalcone groups at 1600 cm-'+ and 1585 cm-'. In addition, the absorption based on nitro group is 1560 Cm'',
"1350 cm-" Ni? b Rare f, :,.
実施例7
分子量45000のポリヒドロキシエチルアクリレート
1.15gをジメチルポルムアミド80m1に溶解しこ
れに4−カルボキシカルコン2.52gと2.4.6−
)リニトロクロルベンゼン2.53gを加え、さらにピ
リジン4.2gを添加し40℃で24時間反応させる。Example 7 1.15 g of polyhydroxyethyl acrylate with a molecular weight of 45,000 was dissolved in 80 ml of dimethylpolamide, and 2.52 g of 4-carboxychalcone and 2.4.6-
) Add 2.53 g of linitrochlorobenzene, further add 4.2 g of pyridine, and react at 40° C. for 24 hours.
次に得られた反応混合物を大過剰のエタノールに注加し
て目的とする感光性樹脂を単離する。エタノールで洗浄
後、乾燥した。収量は3.24gであった。このものの
紫外線吸収スペクトルを調べたところ吸収極大は310
nmであり、これからカルコン基の導入率を調べたと
ころ87%であった。さらに赤外線吸収スペクトルを調
べたところカルコン基に基づく吸収が1605 crn
−’。Next, the obtained reaction mixture is poured into a large excess of ethanol to isolate the desired photosensitive resin. After washing with ethanol, it was dried. Yield was 3.24g. When I investigated the ultraviolet absorption spectrum of this substance, the absorption maximum was 310.
nm, and when the chalcone group introduction rate was investigated from this, it was 87%. Further investigation of the infrared absorption spectrum revealed that the absorption based on chalcone groups was 1605 crn.
-'.
及び1665 Cm−’ に認められた。and 1665 Cm-'.
特許出願人 工業技術院長 川田裕部Patent applicant Hirobe Kawada, Director of the Agency of Industrial Science and Technology
Claims (1)
合であり、他は単なる結合、R3は水素原子、アルキル
基、シアノ基、ニトロ基、アルコキシ基、アルコキシカ
ルボニル基、ハロゲン原子である) で表わされるカルコン誘導体を有効量の2,4゜6−ト
リニトロクロルベンゼンの存在下で反応させることを特
徴とする。 一般式 (式中のR,、R2,Rs は前記と同じ意味を示す) で表わされる基を有する感光性樹脂の製法。[Claims] A polymer or copolymer having an alcoholic hydroxyl group has the general formula (in the formula, one of R1 and R2 is an oxomethylene bond, the other is a simple bond, R3 is a hydrogen atom, an alkyl group, cyano group, nitro group, alkoxy group, alkoxycarbonyl group, or halogen atom) in the presence of an effective amount of 2,4゜6-trinitrochlorobenzene. . A method for producing a photosensitive resin having a group represented by the general formula (R, , R2, and Rs in the formula have the same meanings as above).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14589083A JPS6036504A (en) | 1983-08-10 | 1983-08-10 | Production of photo-sensitive resin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14589083A JPS6036504A (en) | 1983-08-10 | 1983-08-10 | Production of photo-sensitive resin |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6036504A true JPS6036504A (en) | 1985-02-25 |
JPS6328442B2 JPS6328442B2 (en) | 1988-06-08 |
Family
ID=15395413
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14589083A Granted JPS6036504A (en) | 1983-08-10 | 1983-08-10 | Production of photo-sensitive resin |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6036504A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6770720B2 (en) * | 1999-09-07 | 2004-08-03 | Hyundai Electronics Industries Co., Ltd. | Organic polymer for organic anti-reflective coating layer and preparation thereof |
-
1983
- 1983-08-10 JP JP14589083A patent/JPS6036504A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6770720B2 (en) * | 1999-09-07 | 2004-08-03 | Hyundai Electronics Industries Co., Ltd. | Organic polymer for organic anti-reflective coating layer and preparation thereof |
Also Published As
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JPS6328442B2 (en) | 1988-06-08 |
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