JPH06116222A - Addition polymerization-type monomer bearing azide group - Google Patents
Addition polymerization-type monomer bearing azide groupInfo
- Publication number
- JPH06116222A JPH06116222A JP28933392A JP28933392A JPH06116222A JP H06116222 A JPH06116222 A JP H06116222A JP 28933392 A JP28933392 A JP 28933392A JP 28933392 A JP28933392 A JP 28933392A JP H06116222 A JPH06116222 A JP H06116222A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- addition polymerization
- photosensitive resin
- type monomer
- 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.)
- Pending
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は分子内にアジド基を含む
付加重合型モノマーに関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an addition polymerization type monomer having an azido group in its molecule.
【０００２】[0002]
【従来の技術】同一分子内にアジド基を含む付加重合型
モノマーとしては、メタクリル酸−２−（ｐ−アジドベ
ンゾイルオキシ）エチルが知られている（高分子論文
集，３５（５），ＰＰ３３１〜３３７，（１９７
８））。2. Description of the Related Art 2- (p-Azidobenzoyloxy) ethyl methacrylate is known as an addition-polymerizable monomer containing an azido group in the same molecule (Polymer Proceedings, 35 (5), PP331). ~ 337, (197
8)).
【０００３】[0003]
【発明が解決しようとする課題】しかしこれらの化合物
は、紫外線吸収域が３００ｎｍ以下にあるため、この波
長域を遮断する工業的に安価なソーダガラス製フォトマ
スクあるいは乳剤被覆製のフォトマスクを使用するにあ
たっては低感度であり、実用的ではないという課題があ
る。However, since these compounds have an ultraviolet absorption range of 300 nm or less, an industrially inexpensive soda glass photomask or emulsion-coated photomask that blocks this wavelength range is used. In doing so, there is a problem that the sensitivity is low and it is not practical.
【０００４】[0004]
【課題を解決するための手段】本発明者らは３００ｎｍ
以上に紫外線吸収域を持つアジド基含有付加重合型モノ
マーを得ることを目的に鋭意検討した結果本発明に到達
した。即ち本発明は、式Means for Solving the Problems The present inventors
The present invention has been accomplished as a result of intensive studies aimed at obtaining an azide group-containing addition polymerization type monomer having an ultraviolet absorption region. That is, the present invention is a formula
【０００５】[0005]
【化２】 [Chemical 2]
【０００６】で表されるアジド基含有付加重合型モノマ
ーである。It is an azide group-containing addition polymerization type monomer represented by:
【０００７】本発明の化合物中に含まれる不飽和基は、
単独重合、あるいは通常の付加重合型モノマーと共重合
することにより、アジド基をポリマーに導入する役割を
担っている。アジド基は、紫外線や可視光線などの電磁
波や電子線等の粒子線に感光して活性種であるナイトレ
ンを発生し、ナイトレン同士の二量化反応、二重結合へ
の付加反応、水素引き抜き反応等を起こし、ポリマー分
子間の架橋をもたらして陽画形成を可能とする。また本
発明の化合物中に含まれるアジド基は、カルコン基と共
役の位置にあるため、その紫外線吸収域が３００ｎｍ以
上となっている。The unsaturated group contained in the compound of the present invention is
It plays a role of introducing an azide group into the polymer by homopolymerization or copolymerization with a usual addition polymerization type monomer. The azido group is exposed to electromagnetic waves such as ultraviolet rays and visible rays and particle beams such as electron beams to generate nitrene, which is an active species. And cause cross-linking between polymer molecules to enable positive image formation. Further, the azide group contained in the compound of the present invention is in a conjugated position with the chalcone group, and thus has an ultraviolet absorption region of 300 nm or more.
【０００８】本発明の化合物は、例えば次に示す工程を
経て合成できる。The compound of the present invention can be synthesized, for example, through the steps shown below.
【０００９】[0009]
【化３】 [Chemical 3]
【００１０】即ち、化合物（Ａ）と蟻酸をアセトン中に
溶解し、還流下で反応させることによって本発明の化合
物を得ることができる。That is, the compound of the present invention can be obtained by dissolving the compound (A) and formic acid in acetone and reacting under reflux.
【００１１】本発明の化合物は、単独重合、あるいは通
常の付加重合型モノマーと共重合させることによってポ
リマー中にアジド基を導入することができる。その結果
得られたポリマーは、３００ｎｍ以上に吸収域を持つア
ジド基を持つため高感度な感光性樹脂となる。The compound of the present invention can be introduced with an azide group into the polymer by homopolymerization or copolymerization with a usual addition polymerization type monomer. The resulting polymer has a high sensitivity as it has an azido group having an absorption region at 300 nm or more.
【００１２】[0012]
【実施例】以下実施例により本発明を更に説明するが本
発明はこれに限定されるものではない。 実施例 本発明の化合物の合成 化合物（Ａ）3.0g(6.7mmol)と蟻酸10.0g(217mmol)をア
セトン40ml中に溶解し、還流下１８時間反応させる。こ
こから溶媒を留去したのち乾燥して本発明の化合物を得
た。化合物の構造は、ＮＭＲ（核磁気共鳴スペクトル分
析）、ＩＲ（赤外吸収スペクトル分析）および元素分析
により確認した。 NMR(ppm) 1.90(s,3H) 3.27(s,3H) 3.38(s,3H) 3.70〜4.30(m,3H) 4.60(d,2H) 5.78(s,1H) 6.13(s,1H) 7.12(d,2H) 7.20(d,2H) 7.69(d,1H) 7.92(d,1H) 7.94(d,2H) 8.17(d,2H) 8.38(s,1H) IR(cm-1) 3400.0 3230.0 3100.0 3030.0 2950.0 2110.0 1715.0 1650.0 1627.0 1600.0 1500.0 1450.0 1418.0 1338.0 1288.0 1252.0 1220.0 1168.0 1023.0 975.0 820.0 750.0 670.0 525.0 510.0 また、本化合物のＵＶ（紫外線吸収スペクトル）のチャ
ートを図１に示す。The present invention will be further described with reference to the following examples, but the present invention is not limited thereto. Example Synthesis of compound of the present invention 3.0 g (6.7 mmol) of compound (A) and 10.0 g (217 mmol) of formic acid are dissolved in 40 ml of acetone and reacted under reflux for 18 hours. The solvent was distilled off from this and dried to obtain the compound of the present invention. The structure of the compound was confirmed by NMR (nuclear magnetic resonance spectrum analysis), IR (infrared absorption spectrum analysis) and elemental analysis. NMR (ppm) 1.90 (s, 3H) 3.27 (s, 3H) 3.38 (s, 3H) 3.70 ~ 4.30 (m, 3H) 4.60 (d, 2H) 5.78 (s, 1H) 6.13 (s, 1H) 7.12 ( d, 2H) 7.20 (d, 2H) 7.69 (d, 1H) 7.92 (d, 1H) 7.94 (d, 2H) 8.17 (d, 2H) 8.38 (s, 1H) IR (cm -1 ) 3400.0 3230.0 3100.0 3030.0 2950.0 2110.0 1715.0 1650.0 1627.0 1600.0 1500.0 1450.0 1418.0 1338.0 1288.0 1252.0 1220.0 1168.0 1023.0 975.0 820.0 750.0 670.0 525.0 510.0 A UV (ultraviolet absorption spectrum) chart of this compound is shown in FIG.
【００１３】[0013]
【図１】[Figure 1]
【００１４】[0014]
【発明の効果】本発明の化合物は、単独重合あるいは通
常の付加重合型モノマーと共重合することによって、３
００ｎｍ以上に紫外線感光域を持つ感光性樹脂が得られ
る。この感光性樹脂は、該波長域の光を透過する工業的
に安価な乳剤被覆製フォトマスクあるいはソーダガラス
製のフォトマスクの使用が可能となる。従ってこの感光
性樹脂は、例えばＬＳＩ用フォトレジスト、プリント基
板用フォトレジスト、印刷版製造用フォトレジスト、ブ
ラウン管蛍光面製造用フォトレジスト、液晶ディスプレ
ー用カラーフィルター製造用フォトレジスト等に使用で
きる。従って本発明の化合物は感光性樹脂用原料として
有用である。INDUSTRIAL APPLICABILITY The compound of the present invention can be homopolymerized or copolymerized with a usual addition-polymerization type monomer to give 3
It is possible to obtain a photosensitive resin having an ultraviolet light sensitive region of 00 nm or more. With this photosensitive resin, it is possible to use an industrially inexpensive emulsion-coated photomask or soda glass-made photomask that transmits light in the wavelength range. Therefore, this photosensitive resin can be used, for example, as a photoresist for LSI, a photoresist for printed circuit boards, a photoresist for producing printing plates, a photoresist for producing cathode ray tube fluorescent screens, a photoresist for producing color filters for liquid crystal displays, and the like. Therefore, the compound of the present invention is useful as a raw material for a photosensitive resin.
【図１】図１は実施例で合成した化合物のＵＶチャート
である。FIG. 1 is a UV chart of compounds synthesized in Examples.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28933392A JPH06116222A (en) | 1992-10-01 | 1992-10-01 | Addition polymerization-type monomer bearing azide group |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28933392A JPH06116222A (en) | 1992-10-01 | 1992-10-01 | Addition polymerization-type monomer bearing azide group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06116222A true JPH06116222A (en) | 1994-04-26 |
Family
ID=17741844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28933392A Pending JPH06116222A (en) | 1992-10-01 | 1992-10-01 | Addition polymerization-type monomer bearing azide group |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06116222A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000058275A1 (en) * | 1999-03-31 | 2000-10-05 | Sanyo Chemical Industries, Ltd. | Photosensitive compound and photosensitive composition |
-
1992
- 1992-10-01 JP JP28933392A patent/JPH06116222A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000058275A1 (en) * | 1999-03-31 | 2000-10-05 | Sanyo Chemical Industries, Ltd. | Photosensitive compound and photosensitive composition |
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