JPH0439665A - Radiation sensitive material and pattern forming method - Google Patents
Radiation sensitive material and pattern forming methodInfo
- Publication number
- JPH0439665A JPH0439665A JP2146803A JP14680390A JPH0439665A JP H0439665 A JPH0439665 A JP H0439665A JP 2146803 A JP2146803 A JP 2146803A JP 14680390 A JP14680390 A JP 14680390A JP H0439665 A JPH0439665 A JP H0439665A
- Authority
- JP
- Japan
- Prior art keywords
- resist
- radiation
- pattern
- sensitive material
- polymer
- 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
- 239000000463 material Substances 0.000 title claims abstract description 17
- 230000005855 radiation Effects 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 6
- 229920000642 polymer Polymers 0.000 claims abstract description 12
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 229920001577 copolymer Polymers 0.000 claims abstract description 10
- -1 acrylic ester Chemical class 0.000 claims description 16
- 150000002148 esters Chemical group 0.000 claims description 8
- 238000005530 etching Methods 0.000 abstract description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 230000005865 ionizing radiation Effects 0.000 abstract description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 8
- 239000004926 polymethyl methacrylate Substances 0.000 description 8
- MZVABYGYVXBZDP-UHFFFAOYSA-N 1-adamantyl 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C(=C)C)C3 MZVABYGYVXBZDP-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- VSQYNPJPULBZKU-UHFFFAOYSA-N mercury xenon Chemical compound [Xe].[Hg] VSQYNPJPULBZKU-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- YQXVIXNPXYHTQP-UHFFFAOYSA-N 1,2-dimethyladamantane;prop-2-enoic acid Chemical compound OC(=O)C=C.C1C(C2)CC3CC1C(C)C2(C)C3 YQXVIXNPXYHTQP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PHPRWKJDGHSJMI-UHFFFAOYSA-N 1-adamantyl prop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C=C)C3 PHPRWKJDGHSJMI-UHFFFAOYSA-N 0.000 description 1
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
【発明の詳細な説明】
Ｃ概要〕
放射線用レジストに関し、
優れたエツチング耐性を示すと共に放射線、特に遠紫外
光に対して透明性に優れたレジストを実用化することを
目的とし、
エステル部にアダマンタン骨格を有するアクリル酸エス
テルまたはα置換アクリル酸エステルの重合体か、或い
は該エステルの共重合体からなる放射線感光材料を用い
てレジストを形成し、該レジストを塗布した被処理基板
に放射線を選択露光した後に現像し、レジストパターン
を形成することを特徴としてパターン形成方法を構成す
る。[Detailed Description of the Invention] C Summary] With regard to radiation resists, the purpose of this invention is to commercialize a resist that exhibits excellent etching resistance and is highly transparent to radiation, especially far ultraviolet light. A resist is formed using a radiation-sensitive material made of a polymer of an acrylic ester having a skeleton or an α-substituted acrylic ester, or a copolymer of the ester, and a substrate to be processed coated with the resist is selectively exposed to radiation. The pattern forming method is characterized in that the resist pattern is developed and then developed to form a resist pattern.
本発明は放射線感光材料とパターン形成方法に関する。 The present invention relates to a radiation-sensitive material and a pattern forming method.
半導体集積回路は集積化が進んでＬＳＩやＶＬＳＩが実
用化されており、これと共に配線パターンの最小線幅は
サブミクロン（Ｓｕｂ−ｍｉｃｒｏｎ）に及んでいるが
更に微細化の傾向にある。As semiconductor integrated circuits have become more integrated, LSI and VLSI have come into practical use, and along with this, the minimum line width of wiring patterns has reached sub-micron, but there is a trend towards further miniaturization.
ニーで、機側パターンの形成には薄膜を形成した被処理
基板上にレジストを被覆し、選択露光を行った後に現像
してレジストパターンを作り、これをマスクとしてドラ
イエツチングを行い、その後にレジストを溶解除去する
ことにより薄膜パターンを得る写真蝕刻技術の使用が必
須である。To form a pattern on the machine side, a resist is coated on the substrate to be processed on which a thin film has been formed, and after selective exposure, development is performed to create a resist pattern. Dry etching is performed using this as a mask, and then the resist is It is essential to use photolithographic techniques to obtain a thin film pattern by dissolving and removing.
この写真蝕刻技術に使用する光源として、当初は紫外線
が使用されていたが、波長による制限からサブミクロン
幅の解像は不可能であり、これに代わって波長の短い遠
紫外線や電子線、Ｘ線などを光源としてサブミクロン幅
の解像が行われるようになった。Initially, ultraviolet light was used as a light source for this photoetching technology, but it was impossible to resolve submicron widths due to wavelength limitations, so instead, far ultraviolet light with short wavelengths, electron beams, Submicron width resolution has become possible using lines and other light sources.
本発明はこれら放射線用レジスト材料に関するものであ
る。The present invention relates to these radiation resist materials.
レジストとして従来はフェノール樹脂をベースとするも
のが数多く開発されてきた。Conventionally, many resists based on phenolic resins have been developed.
然し、これらの材料は芳香族環を含むために光の吸収が
大きく、そのため微細化に対応できるだけのパターン精
度は得られない。However, since these materials contain aromatic rings, they absorb a large amount of light, and therefore cannot obtain pattern precision sufficient to support miniaturization.
一方、吸収の少ない樹脂としてポリメチルメタクリレー
ト（略称ＰＭＭＡ ）やポリメチルイソプロピルケトン
（略称ＰＭＩＰＫ）などが検討されているが、芳香族環
を含んでいないために充分なエツチング耐性をもってい
ない。On the other hand, polymethyl methacrylate (abbreviated as PMMA) and polymethyl isopropyl ketone (abbreviated as PMIPK) are being considered as resins with low absorption, but they do not have sufficient etching resistance because they do not contain aromatic rings.
これらのことから、透明性に優れ、且つ充分なエツチン
グ耐性を備えたレジストは実用化されていない。For these reasons, a resist with excellent transparency and sufficient etching resistance has not been put into practical use.
以上記したようにサブミクロンの微細パターンを現像す
るには遠紫外光に対して透明性が優れ、且つ、充分なエ
ツチング耐性をもつ感光材料が必要であり、この両方の
特性を兼ね備えた放射用感光材料を実用化することが課
題である。As mentioned above, in order to develop submicron fine patterns, a photosensitive material with excellent transparency to deep ultraviolet light and sufficient etching resistance is required. The challenge is to put photosensitive materials into practical use.
上記の課題はエステル部にアダマンタン骨格を有するア
クリル酸エステルまたはα置換アクリル酸エステルの重
合体か、或いはこのエステルの共重合体からなる放射線
感光材料を用いてレジストを形成し、このレジストを塗
布した被処理基板に放射線を選択露光した後に現像し、
レジストパターンを形成することを特徴としてパターン
形成方法を構成することにより・解決することができる
。The above problem was solved by forming a resist using a radiation-sensitive material made of a polymer of acrylic ester or α-substituted acrylic ester having an adamantane skeleton in the ester moiety, or a copolymer of this ester, and applying this resist. The substrate to be processed is selectively exposed to radiation and then developed.
This problem can be solved by configuring a pattern forming method characterized by forming a resist pattern.
本発明は遠紫外光に対して透明性が優れ、且つ、充分な
エツチング耐性をもつ感光材料として、アダマンタン骨
格を有するアクリル酸エステルまたはα置換アクリル酸
エステルの重合体か、或いはこのエステルの共重合体か
らなる材料を用いるものである。The present invention uses a polymer of an acrylic ester having an adamantane skeleton or an α-substituted acrylic ester, or a copolymer of this ester, as a photosensitive material having excellent transparency to deep ultraviolet light and sufficient etching resistance. It uses a material made of coalescence.
すなわち、第１図の（１）式で構造を示すアダマンタン
（Ｃ＋。Ｈ１６）は椅子型構造のシクロヘキサン環を構
成単位としており化学的に非常に安定な化合物として知
られ、医薬品への用途開発が試みられている。In other words, adamantane (C+.H16), whose structure is represented by formula (1) in Figure 1, has a cyclohexane ring with a chair-shaped structure as a constituent unit, and is known to be a chemically very stable compound, and has been developed for use in pharmaceuticals. is being attempted.
発明者はアダマンタン骨格を分子中に含むポリマーは芳
香族環がないにも拘らず優れたエツチング耐性を示し、
また遠紫外光に対して吸収が少ない点に着目した。The inventor discovered that polymers containing an adamantane skeleton in their molecules exhibit excellent etching resistance despite the lack of aromatic rings.
We also focused on the fact that it has little absorption of far ultraviolet light.
そこで、この特徴を活かし、エステル部にアダマンタン
骨格を有するアクリル酸エステルまたはα置換アクリル
酸エステルの重合体か、或いはこのエステルの共重合体
を感光材料として使用するものである。Therefore, taking advantage of this characteristic, a polymer of an acrylic ester or an α-substituted acrylic ester having an adamantane skeleton in the ester moiety, or a copolymer of this ester is used as a light-sensitive material.
このような感光材料は優れたエツチング耐性をもつと共
に透明性に優れているため、精度よくサブミクロンパタ
ーンを形成することができる。Since such photosensitive materials have excellent etching resistance and transparency, submicron patterns can be formed with high precision.
実施例１：
第１図の（２）式に構造式を示すアダマンチルメタクリ
レート４．４ｇとベンゼン５．０ｇに反応開始剤として
アゾイソブルロニトリル（略称ＡｒＢＮ）０．５モル％
を加え、７０°Ｃで約８時間重合した後、メタノールで
再沈精製を行った結果、重量平均分子量１８万９分散度
１．６のポリマーが得られた。Example 1: 0.5 mol % of azoisobronitrile (abbreviated as ArBN) as a reaction initiator was added to 4.4 g of adamantyl methacrylate whose structural formula is shown in formula (2) in FIG.
was added and polymerized at 70°C for about 8 hours, followed by reprecipitation purification with methanol, resulting in a polymer with a weight average molecular weight of 180,099 and a dispersity of 1.6.
これをキシレン溶液とした後、石英基板上に１゜０μｍ
厚に被覆し、遠紫外光（２４８ｎｍ）に対する透明性を
調べた結果、透過率は９７％であって、ＰＭＭＡと同等
であった。After making this into a xylene solution, it was placed on a quartz substrate with a thickness of 1°0 μm.
As a result of coating it thickly and examining its transparency to far ultraviolet light (248 nm), the transmittance was 97%, which was equivalent to PMMA.
なお、ＰＭＭＡの透過率は９８％またフェノールノボラ
ック樹脂の透過率は３０％である。Note that the transmittance of PMMA is 98%, and the transmittance of phenol novolak resin is 30%.
更に、四弗化炭素ガス（ＣＦ４）によるエツチングレー
トをＰＭＭＡと比較した結果、ＰＭＭＡのエラチンレー
トが１３３０人／分であるのに対しポリアダマンチルメ
タクリレートは８６０ Ａ／分と優れていた。Furthermore, as a result of comparing the etching rate with carbon tetrafluoride gas (CF4) with PMMA, the etching rate of PMMA was 1330 A/min, whereas polyadamantyl methacrylate was superior at 860 A/min.
なお、エツチング条件は、ＣＦ４の流量は２０ｓｅｃｍ
。The etching conditions are as follows: CF4 flow rate is 20 sec.
.
真空度はＩ Ｘｌ０−’ｔｏｒｒ、 μ波の出力はＩＫ
Ｗ、高周波電力は１００Ｗである。Vacuum degree is I Xl0-'torr, μ wave output is IK
W, and the high frequency power is 100W.
次に、得られたアダマンチルメタクリレートポリマーに
架橋剤として第１図の（３）式に構造式を示す４．４′
−ジアジドジフェニルメチレンを２０重量％添加してキ
シレン溶液とし、Ｓｉ基板上に０．５μｍの厚さに塗布
した後、１００℃で３０分間プリベークした。Next, 4.4′, whose structural formula is shown in formula (3) in FIG.
-Diazidiphenylmethylene was added in an amount of 20% by weight to make a xylene solution, which was coated on a Si substrate to a thickness of 0.5 μm, and then prebaked at 100° C. for 30 minutes.
その後、キセノン・水銀（Ｘｅ−Ｈｇ）ランプにより３
０秒間露光した後、キシレンで６０秒間現像してパター
ンニング特性を調べた。After that, the xenon-mercury (Xe-Hg) lamp
After exposure for 0 seconds, the patterning characteristics were examined by developing with xylene for 60 seconds.
その結果、０．６μｍのライン・アンド・スペースパタ
ーンを解像することができた。As a result, a line and space pattern of 0.6 μm could be resolved.
比較例１：
フェノールノボラック樹脂をベースにしたｇ線（４３６
ｎｍ）用レジストを用い、実施例１と同様な実験を行っ
たが、得られたレジストパターンの断面形状はテーパー
状となった。Comparative Example 1: G-line (436
An experiment similar to that in Example 1 was conducted using a resist for 200 nm), but the cross-sectional shape of the resulting resist pattern was tapered.
実施例２：
実施例１のアダマンチルメタクリレートの代わりに第１
図の（４）式に構造式を示すジメチルアダマンクンアク
リレートを用いて同様な実験を行った結果、同様な結果
が得られた。Example 2: In place of adamantyl methacrylate in Example 1, the first
A similar experiment was conducted using dimethyladamancune acrylate whose structural formula is shown in formula (4) in the figure, and similar results were obtained.
実施例３：
実施例１において架橋剤として４，４ −ジアジドフェ
ニルメチレンの代わりに第１図の（５）式に構造式を示
す４，４′−ジアジドフェニルスルホンを用いても同様
な結果を得ることができた。Example 3: The same result could be obtained by using 4,4'-diazidophenyl sulfone, whose structural formula is shown in formula (5) in Figure 1, in place of 4,4-diazidophenylmethylene as the crosslinking agent in Example 1. I was able to get results.
実施例４：
ＡＩＢＮを重合開始剤とし、アダマンチルメタクリレー
トとメタクリル酸とを１．４−ジオキサン中で８０℃、
８時間重合させた後、ヘキサンを用いて再沈精製を行っ
た結果、重量平均分子量２万９分散度２．０１組成比が
７：３の共重合体が得られた。Example 4: Using AIBN as a polymerization initiator, adamantyl methacrylate and methacrylic acid were mixed in 1,4-dioxane at 80°C.
After polymerization for 8 hours, reprecipitation purification using hexane yielded a copolymer with a weight average molecular weight of 20,000, a degree of dispersion of 2.01, and a composition ratio of 7:3.
このポリマーに架橋剤として４，４′−ジアジドフェニ
ルメチレンを３０重量％加えてシクロヘキサン溶液とし
、Ｓｉ基板上に０．５μｍの厚さに塗布した後、１００
℃、３０分間プリベークを行った。A cyclohexane solution was prepared by adding 30% by weight of 4,4'-diazidophenylmethylene as a crosslinking agent to this polymer, and the solution was coated on a Si substrate to a thickness of 0.5 μm.
Prebaking was performed at ℃ for 30 minutes.
その後、Ｘｅ−Ｈｇランプにより３０秒間露光したのち
、アルカリ現像を行った。Thereafter, after exposure for 30 seconds using a Xe-Hg lamp, alkaline development was performed.
その結果、０．５μｍのライン・アンド・スペースパタ
ーンを解像することができた。As a result, a line and space pattern of 0.5 μm could be resolved.
なお、エツチング耐性はポリアダマンチルメタクリレー
トの場合と同様であった。Note that the etching resistance was similar to that of polyadamantyl methacrylate.
実施例５
実施例４と同様な方法によりアダマンチルメタクリレー
トとメタクリル酸ｔ−ブチルを共重合した結果、重量平
均分子量１．２万９分散度１．５２組成比が６：４の共
重合体が得られた。Example 5 As a result of copolymerizing adamantyl methacrylate and t-butyl methacrylate in the same manner as in Example 4, a copolymer with a weight average molecular weight of 12,000, a degree of dispersion of 1.52, and a composition ratio of 6:4 was obtained. It was done.
このポリマーに酸発生剤であり、第１図の（６）式に構
造式を示すトリフェニルスルホニウムへキサフロロホス
フェートを５重量％加えてシクロヘキサン溶液とし、Ｓ
ｉ基板上に１．０μ０の厚さに塗布した後、９０°Ｃ１
３０分間プリベークを行った。To this polymer, 5% by weight of triphenylsulfonium hexafluorophosphate, which is an acid generator and whose structural formula is shown in formula (6) in Figure 1, was added to form a cyclohexane solution.
After coating on the i-substrate to a thickness of 1.0μ0, heat at 90°C1.
Prebaking was performed for 30 minutes.
その後、Ｘｅ−Ｈｇランプにより５秒間露光したのち、
１１０℃で２０分のベークを行った後、アルカリ現像を
行った。After that, after exposure for 5 seconds with a Xe-Hg lamp,
After baking at 110° C. for 20 minutes, alkaline development was performed.
その結果、０．５μＷのライン・アンド・スペースパタ
ーンを解像することができた。As a result, a line and space pattern of 0.5 μW could be resolved.
なお、エツチング耐性はポリアダマンクンチルメタクリ
レートの場合と同様であり、また樹脂の透明性はＰＭＭ
Ａと同様であった。The etching resistance is the same as that of polyadamancuntyl methacrylate, and the transparency of the resin is that of PMM.
It was similar to A.
実施例６：
実施例５において、酸発生剤として第１図の（７）式に
構造式を示すジフェニルアイオードへキサフロロホスフ
ェートを用いても同様な結果が得られた。Example 6: Similar results were obtained in Example 5 using diphenyl iode hexafluorophosphate having the structural formula shown in formula (7) in FIG. 1 as the acid generator.
実施例７：
実施例４においてアダマンチルメタクリレートの代わり
にアダマンチルアクリレートを用いた場合も同様な結果
を得ることができた。Example 7: Similar results were obtained when adamantyl acrylate was used instead of adamantyl methacrylate in Example 4.
実施例８：
実施例１と同様の溶液重合により、重量平均分子量１．
２万９分散度１．５２組成比が６：４の共重合体が得ら
れた。Example 8: By solution polymerization similar to Example 1, a weight average molecular weight of 1.
A copolymer with a dispersity of 1.52 and a composition ratio of 6:4 was obtained.
この重合体に第１図の（８）式に構造式を示す４−４−
ジアドカルコンを７重量％添加してキシレン溶液とした
。This polymer has the structural formula shown in formula (8) in Figure 1.
A xylene solution was prepared by adding 7% by weight of diadochalcone.
この溶液をＳｉ基板上に１．０μｍの厚さに塗布した後
、Ｎ２気流中で２００°Ｃ，１時間のプリベークを行い
、熱架橋させて不溶化した後、加速電圧２０ＫＶの電子
線露光装置で露光した。After applying this solution to a thickness of 1.0 μm on a Si substrate, it was prebaked at 200°C for 1 hour in a N2 stream to thermally crosslink and insolubilize, and then exposed to an electron beam exposure device with an accelerating voltage of 20 KV. exposed.
この後、キシレンで現像した結果、６４μＣ／ｃｍ”の
露光量で０．８μｍのライン・アンド・スペースパター
ンを解像することができた。Thereafter, development was performed with xylene, and as a result, a line and space pattern of 0.8 μm could be resolved with an exposure dose of 64 μC/cm”.
なお、同様な実験をＰＭＭＡを用いて行い、エツチング
耐性を比較した結果、ＰＭＭＡの１．５倍であった。A similar experiment was conducted using PMMA, and the etching resistance was compared and found to be 1.5 times that of PMMA.
実施例９：
実施例５において現像液としてアルカリ現像液の代わり
にキシレンを用いることにより、０．８μｍのライン・
アンド・スペースのネガパターンを得ることができた。Example 9: By using xylene instead of the alkaline developer as the developer in Example 5, 0.8 μm line/
I was able to obtain a negative pattern of & space.
本発明によれば、電離放射線に対し、透明性が高（、且
つ充分なエツチング耐性をもつレジストパターンを得る
ことができ、これによりサブミクロン・パターンを得る
ことができる。According to the present invention, it is possible to obtain a resist pattern that is highly transparent to ionizing radiation (and has sufficient etching resistance), thereby making it possible to obtain a submicron pattern.
第１図は本発明の実施において使用した有機化合物の構
造式である。
アダマンタンの構造式
アダマンチルメタクリレートの構造式
Ｎ５−（）ＣＨ２÷Ｎ３０１１．（３）４４゛ −ジ
アジドフェニルメチレンの構造式トリフェニルスルホニ
ウムへキサフロロホスフェートの構造式ジフェニノしア
イオートペキサフロロホスフエートの平Ｕジメチルアダ
マンタンアクリレートの構造式％式％（５
４，４° −ジアジドジブエニルスルホンの構造式本発
明の実施においてイ吏用した有Ｗヒ合物の橢左式第 １
図 （その２）
本発明の実施において使用した有機化合物の構造式第
１ 図 （その１）FIG. 1 is a structural formula of an organic compound used in the practice of the present invention. Structural formula of adamantane Structural formula of adamantyl methacrylate N5-()CH2÷N3011. (3) 44゛ -Structural formula of diazidophenylmethylene Structural formula of triphenylsulfonium hexafluorophosphate Structural formula of dimethyladamantane acrylate of dipheninosulfonium hexafluorophosphate %Formula% (5 4,4° - Structural formula of diazide dibuenyl sulfone:
Figure (Part 2) Structural formula of organic compound used in carrying out the present invention
Figure 1 (Part 1)
Claims (2)
酸エステルまたはα置換アクリル酸エステルの重合体か
、或いは該エステルの共重合体からなることを特徴とす
る放射線感光材料。(1) A radiation-sensitive material comprising a polymer of an acrylic ester or α-substituted acrylic ester having an adamantane skeleton in the ester moiety, or a copolymer of the ester.
を形成し、該レジストを塗布した被処理基板に放射線を
選択露光した後に現像し、レジストパターンを形成する
ことを特徴とするパターン形成方法。(2) A pattern forming method comprising forming a resist using the radiation-sensitive material according to claim 1, selectively exposing a substrate coated with the resist to radiation, and then developing to form a resist pattern. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2146803A JP2881969B2 (en) | 1990-06-05 | 1990-06-05 | Radiation-sensitive resist and pattern forming method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2146803A JP2881969B2 (en) | 1990-06-05 | 1990-06-05 | Radiation-sensitive resist and pattern forming method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0439665A true JPH0439665A (en) | 1992-02-10 |
| JP2881969B2 JP2881969B2 (en) | 1999-04-12 |
Family
ID=15415885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2146803A Expired - Lifetime JP2881969B2 (en) | 1990-06-05 | 1990-06-05 | Radiation-sensitive resist and pattern forming method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2881969B2 (en) |
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| US6120977A (en) * | 1993-10-26 | 2000-09-19 | Fujitsu Limited | Photoresist with bleaching effect |
| US5679495A (en) * | 1993-12-03 | 1997-10-21 | Japan Synthetic Rubber Co., Ltd. | Radiation sensitive resin composition |
| USRE37179E1 (en) * | 1993-12-03 | 2001-05-15 | Jsr Corporation | Radiation sensitive resin composition |
| US5556734A (en) * | 1993-12-24 | 1996-09-17 | Japan Synthetic Rubber Co., Ltd. | Radiation sensitive resin composition comprising copolymer of isopropenylphenol and T-butyl(meth)acrylate |
| US5660969A (en) * | 1993-12-27 | 1997-08-26 | Fujitsu Limited | Chemical amplification resist and a fabrication process of a semiconductor device that uses such a chemical amplification resist |
| JPH07199467A (en) * | 1993-12-28 | 1995-08-04 | Nec Corp | Photosensitive resin composition and method for forming pattern |
| US7465529B2 (en) | 1993-12-28 | 2008-12-16 | Fujitsu Limited | Radiation sensitive material and method for forming pattern |
| US6790589B2 (en) | 1993-12-28 | 2004-09-14 | Fujitsu Limited | Radiation sensitive material and method for forming pattern |
| US7179580B2 (en) | 1993-12-28 | 2007-02-20 | Fujitsu Limited | Radiation sensitive material and method for forming pattern |
| EP0663616A2 (en) * | 1993-12-28 | 1995-07-19 | Fujitsu Limited | Radiation sensitive material and method for forming pattern |
| US6329125B2 (en) * | 1995-06-28 | 2001-12-11 | Fujitsu Limited | Chemically amplified resist compositions and process for the formation of resist patterns |
| US5932391A (en) * | 1995-08-18 | 1999-08-03 | Kabushiki Kaisha Toshiba | Resist for alkali development |
| US5962180A (en) * | 1996-03-01 | 1999-10-05 | Jsr Corporation | Radiation sensitive composition |
| US6699645B2 (en) | 1996-03-07 | 2004-03-02 | Fujitsu Limited | Method for the formation of resist patterns |
| US6790580B2 (en) | 1996-03-07 | 2004-09-14 | Fujitsu Limited | Resist material and method for forming a resist pattern with the resist material |
| US6077644A (en) * | 1996-08-20 | 2000-06-20 | Tokyo Ohka Kogyo Co., Ltd. | Positive-working resist composition |
| US5929271A (en) * | 1996-08-20 | 1999-07-27 | Tokyo Ohka Kogyo Co., Ltd. | Compounds for use in a positive-working resist composition |
| KR100331297B1 (en) * | 1996-12-09 | 2002-04-03 | 쓰끼하시 다미까따 | (meth)acrylic ester copolymers and process for producing the same |
| WO1998025977A1 (en) * | 1996-12-09 | 1998-06-18 | Nippon Soda Co., Ltd. | (meth)acrylic ester copolymers and process for producing the same |
| US6248920B1 (en) | 1996-12-27 | 2001-06-19 | Fujitsu Limited | Preparation process for esters and resist materials |
| US6388101B1 (en) | 1997-01-24 | 2002-05-14 | Tokyo Ohka Kogyo Co., Ltd. | Chemical-sensitization photoresist composition |
| US6225476B1 (en) | 1997-06-27 | 2001-05-01 | Tokyo Ohka Kogyo Co., Ltd. | Positive-working photoresist composition |
| US6087063A (en) * | 1997-06-27 | 2000-07-11 | Tokyo Ohka Kogyo Co., Ltd. | Positive-working photoresist composition |
| US6017680A (en) * | 1997-08-05 | 2000-01-25 | Hitachi, Ltd. | Method for pattern formation and process for preparing semiconductor device |
| US6207342B1 (en) | 1997-10-09 | 2001-03-27 | Fujitsu Limited | Chemically amplified resist material and process for the formation of resist patterns |
| US6027856A (en) * | 1998-04-28 | 2000-02-22 | Fujitsu Limited | Negative-type resist composition and process for forming resist patterns |
| WO1999061956A1 (en) * | 1998-05-25 | 1999-12-02 | Daicel Chemical Industries, Ltd. | Compounds for photoresist and resin composition for photoresist |
| US6391520B1 (en) | 1998-05-25 | 2002-05-21 | Daicel Chemical Industries, Ltd. | Compounds for photoresist and resin composition for photoresist |
| US6372854B1 (en) | 1998-06-29 | 2002-04-16 | Mitsui Chemicals, Inc. | Hydrogenated ring-opening metathesis polymer and its use and production |
| KR100395904B1 (en) * | 1999-04-23 | 2003-08-27 | 주식회사 하이닉스반도체 | Organic Anti-reflective coating material and its preparation |
| US6723485B1 (en) | 1999-11-29 | 2004-04-20 | Central Glass Company, Limited | Positive resist composition and process for forming resist pattern using same |
| US6495307B2 (en) | 2000-02-28 | 2002-12-17 | Sumitomo Chemical Company, Limited | Chemically amplified positive resist composition |
| US6605408B2 (en) | 2000-04-13 | 2003-08-12 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process |
| US6927011B2 (en) | 2000-07-12 | 2005-08-09 | Mitsubishi Rayon Co., Ltd. | Resins for resists and chemically amplifiable resist compositions |
| US6759176B2 (en) | 2000-11-27 | 2004-07-06 | Tokyo Ohka Kogyo Co., Ltd. | Positive-working resist composition |
| US6749989B2 (en) | 2000-12-04 | 2004-06-15 | Tokyo Ohka Kogyo Co., Ltd. | Positive-working photoresist composition |
| JP2002343860A (en) * | 2001-05-17 | 2002-11-29 | Tokyo Ohka Kogyo Co Ltd | Material for forming protective film |
| US6878508B2 (en) | 2001-07-13 | 2005-04-12 | Shin-Etsu Chemical Co., Ltd. | Resist patterning process |
| US7316884B2 (en) | 2001-10-23 | 2008-01-08 | Mitsubishi Rayon Co., Ltd. | 5-methylene-1,3-dioxolan-4-one derivatives, process for their production, polymers of the derivatives, resist compositions, and pattern formation process |
| US7435530B2 (en) | 2001-12-03 | 2008-10-14 | Tokyo Ohka Kogyo Co., Ltd. | Positive type resist composition and resist pattern formation method using same |
| US7326515B2 (en) | 2001-12-03 | 2008-02-05 | Tokyo Ohka Kogyo Co., Ltd. | Positive type resist composition and resist pattern formation method using same |
| US7037995B2 (en) | 2002-09-30 | 2006-05-02 | Shin-Etsu Chemical Co., Ltd. | Tertiary (meth)acrylates having lactone structure, polymers, resist compositions and patterning process |
| DE112004000257B4 (en) | 2003-02-10 | 2022-08-11 | Cypress Semiconductor Corporation | Radiation-sensitive resin composition, method of manufacturing the same, and method of manufacturing a semiconductor device using the same |
| US7041846B2 (en) | 2003-03-07 | 2006-05-09 | Shin-Etsu Chemical Co., Ltd. | Alicyclic methacrylate having oxygen substituent group on α-methyl |
| US7592123B2 (en) | 2003-06-05 | 2009-09-22 | Tokyo Ohka Kogyo Co., Ltd. | Resin for photoresist composition, photoresist composition and method for forming resist pattern |
| US7829259B2 (en) | 2003-06-05 | 2010-11-09 | Tokyo Ohka Kogyo Co., Ltd. | Resin for photoresist composition, photoresist composition and method for forming resist pattern |
| US7285368B2 (en) | 2003-06-12 | 2007-10-23 | Shin-Etsu Chemical Co., Ltd. | Polymerizable ester having sulfonamide structure, polymer, resist composition and patterning process |
| US7544460B2 (en) | 2003-07-09 | 2009-06-09 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, multilayer body, and method for forming resist pattern |
| KR100721089B1 (en) * | 2003-08-07 | 2007-05-23 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Resist Polymer, Resist Composition and Patterning Process |
| US7135270B2 (en) | 2003-08-07 | 2006-11-14 | Shin-Etsu Chemical Co., Ltd. | Resist polymer, resist composition and patterning process |
| US7601479B2 (en) | 2003-09-12 | 2009-10-13 | Shin-Etsu Chemical Co., Ltd. | Polymer, resist composition and patterning process |
| US7682770B2 (en) | 2003-10-23 | 2010-03-23 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition and method for forming resist pattern |
| US7700259B2 (en) | 2004-04-13 | 2010-04-20 | Tokyo Ohka Kogyo Co., Ltd. | Polymer compound, photoresist composition containing such polymer compound, and method for forming resist pattern |
| US8741538B2 (en) | 2004-04-13 | 2014-06-03 | Tokyo Ohka Kogyo Co., Ltd. | Polymer compound, photoresist composition containing such polymer compound, and method for forming resist pattern |
| US7494759B2 (en) | 2004-05-31 | 2009-02-24 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist compositions and process for the formation of resist patterns with the same |
| US7763412B2 (en) | 2004-06-08 | 2010-07-27 | Tokyo Ohka Kogyo Co., Ltd. | Polymer, positive resist composition and method for forming resist pattern |
| US7608381B2 (en) | 2004-06-18 | 2009-10-27 | Tokyo Ohka Kogyo Co., Ltd. | Polymer compound, positive resist composition and process for forming resist pattern |
| US7598015B2 (en) | 2004-06-21 | 2009-10-06 | Shin-Etsu Chemical Co., Ltd. | Polymer, resist composition and patterning process |
| US8029968B2 (en) | 2004-07-02 | 2011-10-04 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and method for resist pattern formation |
| US7482108B2 (en) | 2004-08-03 | 2009-01-27 | Tokyo Ohka Kogyo Co., Ltd. | Polymer compound, acid generator, positive resist composition, and method for formation of resist patterns |
| US7736842B2 (en) | 2004-09-09 | 2010-06-15 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition for electron beam or EUV (extreme ultraviolet) and method for forming resist pattern |
| TWI383249B (en) * | 2005-02-16 | 2013-01-21 | Sumitomo Chemical Co | A salt suitable for an acid generator and a chemically amplified resist composition containing the same |
| US7858286B2 (en) | 2005-05-19 | 2010-12-28 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and method for forming resist pattern |
| WO2007010784A1 (en) * | 2005-07-15 | 2007-01-25 | Idemitsu Kosan Co., Ltd. | Fluoroadamantane derivative, resin composition containing the same, and optical electron member using the resin composition |
| WO2007020901A1 (en) | 2005-08-17 | 2007-02-22 | Idemitsu Kosan Co., Ltd. | Fluorine-containing adamantane derivative, fluorine-containing adamantane derivative having polymerizable group, and resin composition containing same |
| US7939682B2 (en) | 2005-08-17 | 2011-05-10 | Idemitsu Kosan Co., Ltd. | Fluorine-containing adamantane derivative, fluorine-containing adamantane derivative having polymerizable group, and resin composition containing same |
| WO2007026828A1 (en) | 2005-09-01 | 2007-03-08 | Idemitsu Kosan Co., Ltd. | Adamantane derivative, resin composition containing same, and optoelectronic component using same |
| WO2007029598A1 (en) | 2005-09-05 | 2007-03-15 | Idemitsu Kosan Co., Ltd. | Adamantane derivative, epoxy resin, and optical electronic member using resin composition comprising them |
| US8084650B2 (en) | 2006-01-27 | 2011-12-27 | Idemitsu Kosan Co., Ltd. | Adamantane derivative, resin composition containing same, and optoelectronic member and sealing agent for electronic circuit using those |
| WO2007086324A1 (en) | 2006-01-27 | 2007-08-02 | Idemitsu Kosan Co., Ltd. | Adamantane derivative, resin composition containing same, and optoelectronic member and sealing agent for electronic circuit using those |
| WO2007094173A1 (en) | 2006-02-17 | 2007-08-23 | Idemitsu Kosan Co., Ltd. | Adamantane derivative, composition comprising the derivative, and optical and electronic member using the composition |
| US7960483B2 (en) | 2006-02-17 | 2011-06-14 | Idemitsu Kosan Co., Ltd. | Adamantane derivative, composition comprising the derivative, and optical and electronic member using the composition |
| US8017800B2 (en) | 2006-04-28 | 2011-09-13 | Idemitsu Kosan Co., Ltd. | Adamantyl group-containing epoxy-modified (meth)acrylate and resin composition containing the same |
| US7790917B2 (en) | 2006-04-28 | 2010-09-07 | Idemitsu Kosan Co., Ltd. | Adamantyl group-containing epoxy-modified (meth)acrylate and resin composition containing the same |
| WO2007125890A1 (en) | 2006-04-28 | 2007-11-08 | Idemitsu Kosan Co., Ltd. | Adamantyl group-containing epoxy-modified (meth)acrylate and resin composition containing the same |
| WO2007125829A1 (en) | 2006-04-28 | 2007-11-08 | Idemitsu Kosan Co., Ltd. | Fluorine-containing adamantane derivative, fluorine-containing adamantane derivative having polymerizable group, resin composition containing the same, and antireflection film |
| US7871752B2 (en) | 2006-07-28 | 2011-01-18 | Shin-Etsu Chemical Co., Ltd. | Lactone-containing compound, polymer, resist composition, and patterning process |
| US7794915B2 (en) | 2006-09-28 | 2010-09-14 | Mitsui Chemicals, Inc. | Hydrogenated ring-opening metathesis polymer, resist composition comprising the same and patterning method |
| WO2008050796A1 (en) | 2006-10-25 | 2008-05-02 | Idemitsu Kosan Co., Ltd. | Adamantane derivative, process for production thereof, resin composition, and cured product of the resin composition |
| WO2008065939A1 (en) | 2006-11-29 | 2008-06-05 | Idemitsu Kosan Co., Ltd. | Adamantane derivative, method for producing the same, and resin composition containing adamantane derivative |
| US8110614B2 (en) | 2006-11-29 | 2012-02-07 | Idemitsu Kosan Co., Ltd. | Adamantane derivative, method for producing the same, and resin composition containing adamantane derivative |
| JP2008292975A (en) * | 2006-12-25 | 2008-12-04 | Fujifilm Corp | Pattern forming method, positive resist composition for multiple development used in the pattern forming method, developer for negative development used in the pattern forming method, and rinsing solution for negative development used in the pattern forming method |
| JP4554665B2 (en) * | 2006-12-25 | 2010-09-29 | 富士フイルム株式会社 | PATTERN FORMATION METHOD, POSITIVE RESIST COMPOSITION FOR MULTIPLE DEVELOPMENT USED FOR THE PATTERN FORMATION METHOD, NEGATIVE DEVELOPMENT SOLUTION USED FOR THE PATTERN FORMATION METHOD, AND NEGATIVE DEVELOPMENT RINSE SOLUTION USED FOR THE PATTERN FORMATION METHOD |
| US9465298B2 (en) | 2006-12-25 | 2016-10-11 | Fujifilm Corporation | Pattern forming method, resist composition for multiple development used in the pattern forming method, developer for negative development used in the pattern forming method, and rinsing solution for negative development used in the pattern forming method |
| JP2010237695A (en) * | 2006-12-25 | 2010-10-21 | Fujifilm Corp | Pattern forming method, positive resist composition for multiple development used in the pattern forming method, developer for negative development used in the pattern forming method, and rinsing solution for negative development used in the pattern forming method |
| US8951718B2 (en) | 2006-12-25 | 2015-02-10 | Fujifilm Corporation | Pattern forming method, resist composition for multiple development used in the pattern forming method, developer for negative development used in the pattern forming method, and rinsing solution for negative development used in the pattern forming method |
| US9291904B2 (en) | 2006-12-25 | 2016-03-22 | Fujifilm Corporation | Pattern forming method, resist composition for multiple development used in the pattern forming method, developer for negative development used in the pattern forming method, and rinsing solution for negative development used in the pattern forming method |
| US8017304B2 (en) | 2007-04-13 | 2011-09-13 | Fujifilm Corporation | Pattern forming method, and resist composition, developer and rinsing solution used in the pattern forming method |
| US8034547B2 (en) | 2007-04-13 | 2011-10-11 | Fujifilm Corporation | Pattern forming method, resist composition to be used in the pattern forming method, negative developing solution to be used in the pattern forming method and rinsing solution for negative development to be used in the pattern forming method |
| US8241840B2 (en) | 2007-04-13 | 2012-08-14 | Fujifilm Corporation | Pattern forming method, resist composition to be used in the pattern forming method, negative developing solution to be used in the pattern forming method and rinsing solution for negative development to be used in the pattern forming method |
| US8022151B2 (en) | 2007-05-01 | 2011-09-20 | Idemitsu Kosan Co., Ltd. | Adamantane derivative, method for producing the same, resin composition containing the adamantane derivative and use thereof |
| US7985534B2 (en) | 2007-05-15 | 2011-07-26 | Fujifilm Corporation | Pattern forming method |
| JP2008309879A (en) * | 2007-06-12 | 2008-12-25 | Fujifilm Corp | Method of forming pattern |
| JP4590431B2 (en) * | 2007-06-12 | 2010-12-01 | 富士フイルム株式会社 | Pattern formation method |
| JP2008309878A (en) * | 2007-06-12 | 2008-12-25 | Fujifilm Corp | Method of forming pattern |
| US7998655B2 (en) | 2007-06-12 | 2011-08-16 | Fujifilm Corporation | Method of forming patterns |
| US8017298B2 (en) | 2007-06-12 | 2011-09-13 | Fujifilm Corporation | Method of forming patterns |
| US9046782B2 (en) | 2007-06-12 | 2015-06-02 | Fujifilm Corporation | Resist composition for negative tone development and pattern forming method using the same |
| US8088557B2 (en) | 2007-06-12 | 2012-01-03 | Fujifilm Corporation | Method of forming patterns |
| US8071272B2 (en) | 2007-06-12 | 2011-12-06 | Fujifilm Corporation | Method of forming patterns |
| JP4617337B2 (en) * | 2007-06-12 | 2011-01-26 | 富士フイルム株式会社 | Pattern formation method |
| US7807331B2 (en) | 2007-10-19 | 2010-10-05 | Shin-Etsu Chemical Co., Ltd. | Hydrogenated ring-opening metathesis polymer, resist composition and patterning process |
| JP4678413B2 (en) * | 2008-03-13 | 2011-04-27 | 信越化学工業株式会社 | Resist material and pattern forming method |
| JP2009221111A (en) * | 2008-03-13 | 2009-10-01 | Shin Etsu Chem Co Ltd | Lactone-containing compound, polymeric compound, resist material and method for forming pattern |
| US7833694B2 (en) | 2008-03-13 | 2010-11-16 | Shin-Etsu Chemical Co., Ltd. | Lactone-containing compound, polymer, resist composition, and patterning process |
| EP2100887A1 (en) | 2008-03-13 | 2009-09-16 | Shin-Etsu Chemical Co., Ltd. | Lactone-containing compound, polymer, resist composition, and patterning process |
| US8216766B2 (en) | 2008-03-26 | 2012-07-10 | Shin-Etsu Chemical Co., Ltd. | Polymer, polymer preparation method, resist composition and patterning process |
| US8062831B2 (en) | 2008-05-02 | 2011-11-22 | Shin-Etsu Chemical Co., Ltd. | Carboxyl-containing lactone compound, polymer, resist composition, and patterning process |
| JP2009269845A (en) * | 2008-05-02 | 2009-11-19 | Shin Etsu Chem Co Ltd | Carboxy group-having lactone compound, polymer, resist material and pattern-forming method |
| JP4678419B2 (en) * | 2008-05-02 | 2011-04-27 | 信越化学工業株式会社 | Resist material and pattern forming method |
| US8198475B2 (en) | 2008-12-26 | 2012-06-12 | Mitsubishi Gas Chemical Company, Inc. | Method for producing adamantyl (meth)acrylates |
| US8598292B2 (en) | 2009-03-03 | 2013-12-03 | Mitsubishi Gas Chemical Company, Inc. | Adamantane derivative, method for producing same, polymer using same as starting material, and resin composition |
| KR20110124334A (en) | 2009-03-03 | 2011-11-16 | 미츠비시 가스 가가쿠 가부시키가이샤 | Adamantane derivative, method for producing same, polymer using same as starting material, and resin composition |
| WO2011086933A1 (en) | 2010-01-14 | 2011-07-21 | 三菱瓦斯化学株式会社 | Bicyclohexane derivative and production method for same |
| US9150491B2 (en) | 2010-01-14 | 2015-10-06 | Mitsubishi Gas Chemical Company, Inc | Bicyclohexane derivative compound and manufacturing method of the same |
| JP2015227336A (en) * | 2010-01-14 | 2015-12-17 | 三菱瓦斯化学株式会社 | Bicyclohexane derivative compound and production method of the same |
| US9513545B2 (en) | 2010-08-12 | 2016-12-06 | Osaka Organic Chemical Industry Ltd. | Homoadamantane derivatives, process for preparing same, and photoresist compositions |
| US8795946B2 (en) | 2011-07-14 | 2014-08-05 | Shin-Etsu Chemical Co., Ltd. | Polymerizable ester compound, polymer, resist composition, and patterning process |
| KR20130009638A (en) | 2011-07-14 | 2013-01-23 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Polymerizable ester compound, polymer, resist composition, and patterning process |
| US9120288B2 (en) | 2011-09-22 | 2015-09-01 | Fujifilm Corporation | Pattern forming method, actinic ray-sensitive or radiation-sensitive resin composition, resist film, method for preparing electronic device, and electronic device |
| US9140981B2 (en) | 2011-09-22 | 2015-09-22 | Fujifilm Corporation | Actinic-ray-sensitive or radiation-sensitive resin composition, and resist film using the same, pattern forming method, electronic device manufacturing method, and electronic device, each using the same |
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| US9040222B2 (en) | 2012-01-24 | 2015-05-26 | Shin-Etsu Chemical Co., Ltd. | Polymerizable tertiary ester compound, polymer, resist composition, and patterning process |
| US9519214B2 (en) | 2013-02-05 | 2016-12-13 | Fujifilm Corporation | Actinic-ray- or radiation-sensitive resin composition, actinic-ray- or radiation-sensitive film, pattern forming method, process for manufacturing electronic device and electronic device |
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