JP2003226689A - New ester compound - Google Patents
New ester compoundInfo
- Publication number
- JP2003226689A JP2003226689A JP2002182404A JP2002182404A JP2003226689A JP 2003226689 A JP2003226689 A JP 2003226689A JP 2002182404 A JP2002182404 A JP 2002182404A JP 2002182404 A JP2002182404 A JP 2002182404A JP 2003226689 A JP2003226689 A JP 2003226689A
- Authority
- JP
- Japan
- Prior art keywords
- ester compound
- group
- alkyl group
- atom
- 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.)
- Granted
Links
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- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、微細加工技術に適
した化学増幅レジスト材料のベースポリマー用のモノマ
ーとして有用なエステル化合物に関する。TECHNICAL FIELD The present invention relates to an ester compound useful as a monomer for a base polymer of a chemically amplified resist material suitable for microfabrication technology.
【0002】[0002]
【従来の技術及び発明が解決しようとする課題】近年、
LSIの高集積化と高速度化に伴い、パターンルールの
微細化が求められている。微細化が急速に進歩した背景
には投影レンズの高NA化、レジストの性能向上、短波
長化が挙げられる。レジストの高解像度化及び高感度化
に関しては、光照射によって発生する酸を触媒とした化
学増幅ポジ型レジスト材料は優れた性能を有するもので
あり、遠紫外線リソグラフィーにおいて特に主流なレジ
スト材料になった(特公平2−27660号、特開昭6
3−27829号公報等に記載)。また、i線(365
nm)からKrF(248nm)への短波長化は大きな
変革をもたらし、KrFエキシマレーザー用レジスト材
料は0.30ミクロンプロセスに始まり、0.25ミク
ロンルールを経て、現在0.18ミクロンルールの量産
化への適用へと展開している。更には、0.15ミクロ
ンルールの検討も始まっており、微細化の勢いはますま
す加速されている。2. Description of the Related Art In recent years,
Along with high integration and high speed of LSI, miniaturization of pattern rules is required. Background of the rapid progress in miniaturization is to increase the NA of the projection lens, improve the performance of the resist, and shorten the wavelength. With regard to higher resolution and higher sensitivity of the resist, the chemically amplified positive resist material using an acid generated by light irradiation as a catalyst has excellent performance and has become a mainstream resist material in deep ultraviolet lithography. (Japanese Patent Publication No. 27660/1990, Japanese Unexamined Patent Publication No. Sho 6)
3-27829, etc.). In addition, i-line (365
(nm) to KrF (248 nm) has brought about a great change, and the resist material for KrF excimer laser started with 0.30 micron process, went through 0.25 micron rule, and is now mass produced with 0.18 micron rule. It is being applied to Furthermore, studies on the 0.15 micron rule have begun, and the momentum for miniaturization is accelerating.
【0003】ArF(193nm)では、デザインルー
ルの微細化を0.13μm以下にすることが期待されて
いるが、ノボラックやポリビニルフェノール系等の従来
用いられていた樹脂が193nm付近に非常に強い吸収
を持つため、レジスト用のベース樹脂として用いること
ができない。そこで透明性と必要なドライエッチング耐
性の確保のため、アクリル樹脂やシクロオレフィン系の
脂環族系の樹脂が検討されている(特開平9−7317
3号、特開平10−10739号、特開平9−2305
95号公報、WO97/33198)。With ArF (193 nm), it is expected that the fineness of the design rule will be 0.13 μm or less, but the conventionally used resins such as novolac and polyvinylphenol are very strong in the vicinity of 193 nm. Therefore, it cannot be used as a base resin for resist. Therefore, in order to secure transparency and necessary dry etching resistance, acrylic resins and cycloolefin-based alicyclic resins have been investigated (Japanese Patent Laid-Open No. 9-7317).
3, JP-A-10-10739, JP-A-9-2305.
95, WO 97/33198).
【0004】F2(157nm)に関しては0.10μ
m以下の微細化が期待されているが、透明性の確保がま
すます困難になり、ArF用ベースポリマーであるアク
リル樹脂では全く光を透過せず、シクロオレフィン系に
おいてもカルボニル基を有するものは強い吸収を持つこ
とがわかった。また、KrF用ベースポリマーのポリビ
ニルフェノールについては、160nm付近に吸収のウ
ィンドウがあり、若干透過率が向上するものの、実用的
なレベルにはほど遠いことが判明した。For F 2 (157 nm), 0.10 μ
Although miniaturization of m or less is expected, it becomes more and more difficult to ensure transparency, and acrylic resins, which are base polymers for ArF, do not transmit light at all, and cycloolefins with carbonyl groups are also available. It turned out to have a strong absorption. Further, it has been found that polyvinylphenol, which is the base polymer for KrF, has an absorption window near 160 nm and the transmittance is slightly improved, but it is far from a practical level.
【0005】本発明は上記事情に鑑みなされたものであ
り、300nm以下、特にF2(157nm)、Kr
2(146nm)、KrAr(134nm)、Ar2(1
26nm)等の真空紫外光における透過率に優れた化学
増幅レジスト材料のベースポリマーの原料となるモノマ
ーとして有用なエステル化合物を提供することを目的と
する。The present invention has been made in view of the above circumstances, and is 300 nm or less, particularly F 2 (157 nm) and Kr.
2 (146 nm), KrAr (134 nm), Ar 2 (1
It is an object of the present invention to provide an ester compound useful as a monomer that is a raw material of a base polymer of a chemically amplified resist material having excellent transmittance in vacuum ultraviolet light (26 nm).
【0006】[0006]
【課題を解決するための手段及び発明の実施の形態】本
発明者は上記目的を達成するため鋭意検討を重ねた結
果、α位にフッ素を含むアクリル酸誘導体から得られる
樹脂が高い透明性を有すると共に、エステル側鎖にラク
トン環を導入することにより、このモノマーから合成さ
れる樹脂の基板密着性が飛躍的に向上することを知見
し、本発明に至ったものである。Means for Solving the Problems and Modes for Carrying Out the Invention As a result of extensive studies conducted by the present inventor to achieve the above object, the resin obtained from an acrylic acid derivative containing fluorine in the α-position has high transparency. In addition to the above, it was found that the introduction of a lactone ring into the ester side chain dramatically improves the adhesion of the resin synthesized from this monomer to the substrate, and has reached the present invention.
【0007】即ち、本発明は下記のエステル化合物を提
供する。
請求項1:下記一般式(1)で示されるエステル化合
物。That is, the present invention provides the following ester compounds. Claim 1: An ester compound represented by the following general formula (1).
【化3】
(式中、R1はフッ素原子又は少なくとも1個以上のフ
ッ素原子を有する炭素数1〜15の直鎖状、分岐状又は
環状のアルキル基である。R2は水素原子、フッ素原
子、又は炭素数1〜15の直鎖状、分岐状又は環状のア
ルキル基又はフッ素化アルキル基を示す。R3及びR4は
それぞれ単結合もしくは炭素数1〜20のアルキレン基
を示す。)
請求項2:下記一般式(2)で示されるエステル化合
物。[Chemical 3] (In the formula, R 1 is a fluorine atom or a linear, branched, or cyclic alkyl group having 1 to 15 carbon atoms and having at least one or more fluorine atoms. R 2 is a hydrogen atom, a fluorine atom, or a carbon atom. A linear, branched or cyclic alkyl group or a fluorinated alkyl group having a number of 1 to 15. R 3 and R 4 each represent a single bond or an alkylene group having a carbon number of 1 to 20.) Claim 2: An ester compound represented by the following general formula (2).
【化4】
(式中、R1はフッ素原子又は少なくとも1個以上のフ
ッ素原子を有する炭素数1〜15の直鎖状、分岐状又は
環状のアルキル基である。R5は炭素数1〜10のアル
キレン基、酸素原子又は硫黄原子を示す。)
請求項3:上記一般式(1)又は(2)において、R1
がトリフルオロメチル基であることを特徴とする請求項
1又は請求項2記載のエステル化合物。[Chemical 4] (In the formula, R 1 is a fluorine atom or a linear, branched or cyclic alkyl group having 1 to 15 carbon atoms and having at least one fluorine atom. R 5 is an alkylene group having 1 to 10 carbon atoms. Represents an oxygen atom or a sulfur atom.) Claim 3: In the above general formula (1) or (2), R 1
Is a trifluoromethyl group, The ester compound according to claim 1 or 2, wherein
【0008】以下、本発明について更に詳しく説明す
る。本発明者の検討によれば、157nm付近の樹脂の
透過率を向上させる方法としては、カルボニル基や炭素
−炭素間二重結合の数の低減化も一つの方法と考えられ
るが、モノマーユニットへのフッ素原子の導入も透過率
向上に大きく寄与することがわかってきた。特に本発明
者は、下記一般式(1)及び(2)の構造で表されるよ
うなα位にフッ素を含むアクリル酸エステルモノマーか
ら得られるポリマーが157nm付近での高透明性を確
保できることを見出したものである。更には、本モノマ
ーはエステル側鎖にラクトン環を有するため、得られた
ポリマーの基板密着性も飛躍的に向上する。The present invention will be described in more detail below. According to the study of the present inventor, as a method for improving the transmittance of a resin near 157 nm, it is considered that reducing the number of carbonyl groups or carbon-carbon double bonds is also one method. It has been found that the introduction of fluorine atoms also contributes greatly to the improvement of the transmittance. In particular, the present inventors have found that a polymer obtained from an acrylic acid ester monomer containing fluorine at the α-position as represented by the structures of the following general formulas (1) and (2) can secure high transparency in the vicinity of 157 nm. I found it. Furthermore, since this monomer has a lactone ring in the ester side chain, the substrate adhesion of the obtained polymer is dramatically improved.
【0009】[0009]
【化5】
(式中、R1はフッ素原子又は少なくとも1個以上のフ
ッ素原子を有する炭素数1〜15、特に1〜10の直鎖
状、分岐状又は環状のアルキル基である。R2は水素原
子、フッ素原子、又は炭素数1〜15、特に1〜10の
直鎖状、分岐状又は環状のアルキル基又はフッ素化アル
キル基を示す。R3及びR4はそれぞれ単結合もしくは炭
素数1〜20、特に1〜5のアルキレン基を示す。R5
は炭素数1〜10のアルキレン基、酸素原子又は硫黄原
子を示す。)[Chemical 5] (In the formula, R 1 is a fluorine atom or a linear, branched or cyclic alkyl group having 1 to 15 carbon atoms, particularly 1 to 10 carbon atoms, having at least one fluorine atom. R 2 is a hydrogen atom, A fluorine atom, or a linear, branched or cyclic alkyl group or fluorinated alkyl group having 1 to 15 carbon atoms, particularly 1 to 10. R 3 and R 4 are each a single bond or 1 to 20 carbon atoms, Particularly, it represents an alkylene group of 1 to 5. R 5
Represents an alkylene group having 1 to 10 carbon atoms, an oxygen atom or a sulfur atom. )
【0010】ここで、アルキル基としては、メチル基、
エチル基、n−プロピル基、イソプロピル基、n−ブチ
ル基、イソブチル基、tert−ブチル基、ペンチル
基、シクロペンチル基、ヘキシル基、シクロヘキシル
基、オクチル基、デシル基、ドデシル基等が挙げられ
る。フッ素原子を有するアルキル基、フッ素化アルキル
基としては、上記アルキル基の水素原子の一部又は全部
がフッ素原子で置換した基が挙げられる。また、アルキ
レン基としては、上記アルキル基から水素原子が1個脱
離したものが挙げられる。Here, the alkyl group is a methyl group,
Examples thereof include ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, cyclopentyl group, hexyl group, cyclohexyl group, octyl group, decyl group and dodecyl group. Examples of the alkyl group having a fluorine atom and the fluorinated alkyl group include groups in which some or all of the hydrogen atoms of the above alkyl group are substituted with fluorine atoms. Examples of the alkylene group include those obtained by removing one hydrogen atom from the above alkyl group.
【0011】本発明のエステル化合物の具体例を以下に
示すが、これに限定されるものではない。Specific examples of the ester compound of the present invention are shown below, but the invention is not limited thereto.
【化6】 [Chemical 6]
【0012】本発明のエステル化合物の製造は、例えば
下記工程にて行うことができるが、これに限定されるも
のではない。The production of the ester compound of the present invention can be carried out, for example, in the following steps, but is not limited thereto.
【化7】 [Chemical 7]
【0013】ここで、R1〜R5は上記と同様である。反
応は公知の条件にて容易に進行するが、好ましくはトル
エン等の溶媒中、原料のラクトン環を有するアルコー
ル、及びそれと等モル量のα位にフッ素を有するアクリ
ル酸、触媒量のトルエンスルホン酸等の酸を順次又は同
時に加え、加熱環流下で反応させ、生成した水を系外に
取り出すことで平衡を生成物側に移動させ、反応を完結
させる。Here, R 1 to R 5 are the same as above. The reaction proceeds easily under known conditions, but preferably in a solvent such as toluene, an alcohol having a lactone ring as a raw material, an acrylic acid having fluorine at the α-position in an equimolar amount thereto, and a catalytic amount of toluenesulfonic acid. Acids such as the above are added sequentially or simultaneously and reacted under heating reflux, and the produced water is taken out of the system to move the equilibrium to the product side and complete the reaction.
【0014】[0014]
【発明の効果】本発明のエステル化合物をモノマーとし
て製造した樹脂を用いたレジスト材料は、透明性に優れ
ると共に基板密着性に優れているため、電子線や遠紫外
線、特にF2エキシマレーザーによる微細加工に有用で
ある。Resist material of the ester compound with a resin prepared as a monomer of the present invention according to the present invention is excellent in adhesion to substrates along with excellent transparency, electron beam or deep UV, fine in particular by F 2 excimer laser Useful for processing.
【0015】[0015]
【実施例】以下、実施例を示して本発明を具体的に説明
するが、本発明は下記実施例に制限されるものではな
い。EXAMPLES The present invention will now be specifically described with reference to examples, but the present invention is not limited to the following examples.
【0016】[合成例1] 下記モノマー1の合成
33.0gのα−ヒドロキシ−γ−ブチロラクトン、5
0.0gのα−トリフルオロメチルアクリル酸、12.
3gのp−トルエンスルホン酸一水和物を重合安定剤と
共に200gのトルエンに溶解した。フラスコにDea
n−Stark管を取り付け、反応混合物を加熱環流下
で4時間反応させると共に、生成した水を除去した。室
温まで冷却後、通常の反応後処理を行い、得られた油状
物質をシリカゲルクロマトグラフィーで精製したとこ
ろ、60.1gの下記モノマー1が得られた。収率は8
3.0%であった。Synthesis Example 1 Synthesis of Monomer 1 below 33.0 g of α-hydroxy-γ-butyrolactone, 5
0.0 g α-trifluoromethylacrylic acid, 12.
3 g of p-toluenesulfonic acid monohydrate was dissolved in 200 g of toluene together with a polymerization stabilizer. Dea in a flask
An n-Stark tube was attached, the reaction mixture was allowed to react under heating reflux for 4 hours, and the water formed was removed. After cooling to room temperature, usual reaction post-treatment was carried out, and the obtained oily substance was purified by silica gel chromatography to obtain 60.1 g of the following monomer 1. Yield 8
It was 3.0%.
【0017】[0017]
【化8】
1H−NMR(CDCl3、270MHz):δ2.38
(m、1H)、2.78(m、1H)、4.31〜4.
52(m、2H)、5.57(t、1H)、6.56
(m、1H)、6.83(m、1H)
FT−IR(NaCl):2997、2927、178
6、1743、1401、1377、1244、122
2、1176、1144、1107、1016cm-1 [Chemical 8] 1 H-NMR (CDCl 3 , 270 MHz): δ 2.38
(M, 1H), 2.78 (m, 1H), 4.31-4.
52 (m, 2H), 5.57 (t, 1H), 6.56
(M, 1H), 6.83 (m, 1H) FT-IR (NaCl): 2997, 2927, 178.
6, 1743, 1401, 1377, 1244, 122
2,1176,1144,1107,1016cm -1
【0018】[合成例2] 下記モノマー2の合成
36.7gの原料アルコール1、50.0gのα−トリ
フルオロメチルアクリル酸、9.1gのp−トルエンス
ルホン酸一水和物を重合安定剤と共に200gのトルエ
ンに溶解した。フラスコにDean−Stark管を取
り付け、反応混合物を加熱環流下で24時間反応させる
と共に、生成した水を除去した。室温まで冷却後、通常
の反応後処理を行い、得られた油状物質をシリカゲルク
ロマトグラフィーで精製したところ、50.5gのモノ
マー2が得られた。収率は76.8%であった。Synthesis Example 2 Synthesis of Monomer 2 36.7 g of starting alcohol 1, 50.0 g of α-trifluoromethylacrylic acid and 9.1 g of p-toluenesulfonic acid monohydrate were used as polymerization stabilizers. Together with 200 g of toluene. The Dean-Stark tube was attached to the flask, the reaction mixture was reacted under reflux for 24 hours, and the water formed was removed. After cooling to room temperature, usual reaction post-treatment was carried out, and the obtained oily substance was purified by silica gel chromatography to obtain 50.5 g of Monomer 2. The yield was 76.8%.
【0019】[0019]
【化9】
1H−NMR(CDCl3、270MHz):δ1.69
〜1.80(m、2H)、1.98〜2.08(m、2
H)、2.50〜2.61(m、2H)、3.24
(m、1H)、4.59(m、1H)、4.73(m、
1H)、6.46(m、1H)、6.75(m、1H)
FT−IR(NaCl):2981、2887、178
6、1738、1452、1408、1383、135
8、1246、1178、1144、1115、109
5、1014、993cm-1 [Chemical 9] 1 H-NMR (CDCl 3 , 270 MHz): δ 1.69
~ 1.80 (m, 2H), 1.98-2.08 (m, 2
H), 2.50 to 2.61 (m, 2H), 3.24
(M, 1H), 4.59 (m, 1H), 4.73 (m,
1H), 6.46 (m, 1H), 6.75 (m, 1H) FT-IR (NaCl): 2981, 2887, 178.
6, 1738, 1452, 1408, 1383, 135
8, 1246, 1178, 1144, 1115, 109
5,1014,993cm -1
【0020】[合成例3] 下記モノマー3の合成
上記と同様にして、原料アルコール2よりモノマー3を
合成した。収率は72.1%であった。[Synthesis Example 3] Synthesis of Monomer 3 below Monomer 3 was synthesized from raw material alcohol 2 in the same manner as above. The yield was 72.1%.
【0021】[0021]
【化10】
1H−NMR(CDCl3、270MHz):δ1.62
〜1.79(m、2H)、1.93〜2.03(m、2
H)、2.52〜2.71(m、2H)、3.33
(m、1H)、4.45(m、1H)、4.78(m、
1H)、6.41(m、1H)、6.71(m、1H)
FT−IR(NaCl):2980、2885、178
2、1734、1452、1408、1383、135
2、1244、1170、1141、1113、109
5cm-1 [Chemical 10] 1 H-NMR (CDCl 3 , 270 MHz): δ1.62
~ 1.79 (m, 2H), 1.93-2.03 (m, 2
H), 2.52 to 2.71 (m, 2H), 3.33
(M, 1H), 4.45 (m, 1H), 4.78 (m,
1H), 6.41 (m, 1H), 6.71 (m, 1H) FT-IR (NaCl): 2980, 2885, 178.
2, 1734, 1452, 1408, 1383, 135
2, 1244, 1170, 1141, 1113, 109
5 cm -1
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 FI テーマコート゛(参考) // C08F 20/28 G03F 7/039 601 G03F 7/039 601 C07D 307/32 Q (72)発明者 畠山 潤 新潟県中頸城郡頸城村大字西福島28−1 信越化学工業株式会社新機能材料技術研究 所内 (72)発明者 河合 義夫 新潟県中頸城郡頸城村大字西福島28−1 信越化学工業株式会社新機能材料技術研究 所内 (72)発明者 大谷 充孝 埼玉県川越市今福中台2805番地 セントラ ル硝子株式会社化学研究所内 (72)発明者 宮澤 覚 埼玉県川越市今福中台2805番地 セントラ ル硝子株式会社化学研究所内 (72)発明者 堤 憲太郎 埼玉県川越市今福中台2805番地 セントラ ル硝子株式会社化学研究所内 (72)発明者 前田 一彦 東京都千代田区神田錦町3丁目7番地1 セントラル硝子株式会社内 Fターム(参考) 2H025 AA14 AC04 AC06 AD01 AD03 BG00 4C037 FA10 4C062 BB60 4C071 AA03 BB02 CC11 CC21 EE13 FF14 KK11 LL03 4J100 AL26P BA11P BA51P BC53P CA01 ─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. 7 Identification code FI theme code (reference) // C08F 20/28 G03F 7/039 601 G03F 7/039 601 C07D 307/32 Q (72) Inventor Hatakeyama Jun 28-1 Nishifukushima, Kubiki-mura, Nakakubiki-gun, Niigata Shin-Etsu Chemical Co., Ltd. Shin-Etsu Chemical Research Institute (72) Inventor Yoshio Kawai 28-1, Nishi-Fukushima, Kubiki-mura, Nakabuki-gun, Niigata Shin-Etsu Chemical Co., Ltd. New Functional Materials Technology Laboratory (72) Inventor Mitsutaka Otani 2805 Imafuku Nakadai, Kawagoe City, Saitama Central Glass Co., Ltd.Chemical Research Institute (72) Inventor Satoshi Miyazawa 2805 Imafuku Nakadai, Kawagoe City, Saitama Central Glass Co., Ltd. Company Chemical Research Institute (72) Inventor Kentaro Tsutsumi 2805 Imafuku Nakadai, Kawagoe City, Saitama Central Glass Co., Ltd. In-house (72) Inventor Kazuhiko Maeda 3-7 Kandanishiki-cho, Chiyoda-ku, Tokyo 1 F term inside Central Glass Co., Ltd. (reference) 2H025 AA14 AC04 AC06 AD01 AD03 BG00 4C037 FA10 4C062 BB60 4C071 AA03 BB02 CC11 CC21 EE13 FF14 KK11 KK11 4J100 AL26P BA11P BA51P BC53P CA01
Claims (3)
合物。 【化1】 (式中、R1はフッ素原子又は少なくとも1個以上のフ
ッ素原子を有する炭素数1〜15の直鎖状、分岐状又は
環状のアルキル基である。R2は水素原子、フッ素原
子、又は炭素数1〜15の直鎖状、分岐状又は環状のア
ルキル基又はフッ素化アルキル基を示す。R3及びR4は
それぞれ単結合もしくは炭素数1〜20のアルキレン基
を示す。)1. An ester compound represented by the following general formula (1): [Chemical 1] (In the formula, R 1 is a fluorine atom or a linear, branched, or cyclic alkyl group having 1 to 15 carbon atoms and having at least one or more fluorine atoms. R 2 is a hydrogen atom, a fluorine atom, or a carbon atom. A linear, branched or cyclic alkyl group or a fluorinated alkyl group having a number of 1 to 15 is shown. R 3 and R 4 are each a single bond or an alkylene group having a carbon number of 1 to 20.)
合物。 【化2】 (式中、R1はフッ素原子又は少なくとも1個以上のフ
ッ素原子を有する炭素数1〜15の直鎖状、分岐状又は
環状のアルキル基である。R5は炭素数1〜10のアル
キレン基、酸素原子又は硫黄原子を示す。)2. An ester compound represented by the following general formula (2). [Chemical 2] (In the formula, R 1 is a fluorine atom or a linear, branched or cyclic alkyl group having 1 to 15 carbon atoms and having at least one fluorine atom. R 5 is an alkylene group having 1 to 10 carbon atoms. , Represents an oxygen atom or a sulfur atom.)
R1がトリフルオロメチル基であることを特徴とする請
求項1又は請求項2記載のエステル化合物。3. In the general formula (1) or (2),
The ester compound according to claim 1 or 2, wherein R 1 is a trifluoromethyl group.
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JP2006169147A (en) * | 2004-12-14 | 2006-06-29 | Daicel Chem Ind Ltd | Polymerizable unsaturated carboxylic acid ester, polymer compound, resin composition for photoresist and method for producing semiconductor |
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JP2005240024A (en) * | 2004-01-30 | 2005-09-08 | Shin Etsu Chem Co Ltd | Polymer compound, resist material, and pattern forming method |
JP4525912B2 (en) * | 2004-01-30 | 2010-08-18 | 信越化学工業株式会社 | Polymer compound, resist material, and pattern forming method |
JP2011016799A (en) * | 2004-05-11 | 2011-01-27 | Sumitomo Chemical Co Ltd | Chemically amplified positive resist composition, haloester derivative and process for producing the same |
JP2006169147A (en) * | 2004-12-14 | 2006-06-29 | Daicel Chem Ind Ltd | Polymerizable unsaturated carboxylic acid ester, polymer compound, resin composition for photoresist and method for producing semiconductor |
JP2007031356A (en) * | 2005-07-27 | 2007-02-08 | Daicel Chem Ind Ltd | 3-oxa-7-thiatricyclo[4.2.1.04,8]nonane derivative |
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