JP3132885B2 - Resist composition and pattern forming method using the same - Google Patents
Resist composition and pattern forming method using the sameInfo
- Publication number
- JP3132885B2 JP3132885B2 JP04063341A JP6334192A JP3132885B2 JP 3132885 B2 JP3132885 B2 JP 3132885B2 JP 04063341 A JP04063341 A JP 04063341A JP 6334192 A JP6334192 A JP 6334192A JP 3132885 B2 JP3132885 B2 JP 3132885B2
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- resist composition
- resist
- group
- polymer
- forming method
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Description
【０００１】[0001]
【産業上の利用分野】本発明はレジスト組成物及びパタ
ーン形成方法に関し、更に詳しくは感度が高く、電子回
路素子の量産性に優れたレジスト組成物及びパターン形
成方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a resist composition and a pattern forming method, and more particularly, to a resist composition and a pattern forming method having high sensitivity and excellent mass productivity of electronic circuit elements.
【０００２】[0002]
【従来の技術】半導体素子、磁気バブルメモリ素子、表
面バブルメモリ素子などの微細パターンを持つ電子回路
素子の形成には従来からレジストプロセスが多用されて
いる。かかる状況下に、近年、各種電子回路素子の高集
積化に伴い、配線の多層化による基板表面の高段差化が
進んでいる。このため、従来の単層レジストプロセスで
は充分な解像性が得られなくなってきている。そこで有
機樹脂を下層に形成して基板段差を平坦化し、その上に
レジスト層を薄く形成し、上層のみをパターニングした
後、酸素プラズマによって上層パターンを下層に転写す
る二層レジスト法が検討されている。この二層レジスト
法は、下層が基板段差を平坦化するとともに基板からの
光反射を防止し、また上層レジストを薄くできることか
ら、従来の単層レジストに比べ、解像性を著しく向上さ
せることができる。2. Description of the Related Art A resist process has been frequently used for forming an electronic circuit device having a fine pattern such as a semiconductor device, a magnetic bubble memory device, and a surface bubble memory device. Under these circumstances, in recent years, with the increase in the integration of various electronic circuit elements, the height of the substrate surface has been increased by increasing the number of wiring layers. For this reason, the conventional single-layer resist process cannot provide sufficient resolution. Therefore, a two-layer resist method in which an organic resin is formed as a lower layer to flatten a substrate step, a thin resist layer is formed thereon, and only the upper layer is patterned, and the upper layer pattern is transferred to the lower layer by oxygen plasma has been studied. I have. In this two-layer resist method, the lower layer flattens the steps of the substrate, prevents light reflection from the substrate, and can reduce the thickness of the upper layer resist. it can.
【０００３】[0003]
【発明が解決しようとする課題】前記した二層レジスト
法の上層レジストでは酸素プラズマ耐性が要求されるた
めに、レジスト材料として、有機ケイ素重合体が用いら
れる。有機ケイ素重合体に基づくネガ型の二層レジスト
は既に知られており、クロロメチルフェニル基を有する
ポリシロキサンやメチル基を有するラダーポリシロキサ
ンなどが市販されている。しかしながら、これらの有機
ケイ素重合体を用いるレジスト材料の感度は充分とは言
えず、電子回路素子製造のスループット（量産性）向上
の上からも高感度の二層レジストの開発が望まれてい
た。Since the upper resist of the two-layer resist method requires oxygen plasma resistance, an organic silicon polymer is used as a resist material. Negative-type two-layer resists based on organosilicon polymers are already known, and polysiloxanes having a chloromethylphenyl group, ladder polysiloxanes having a methyl group, and the like are commercially available. However, the sensitivity of resist materials using these organosilicon polymers cannot be said to be sufficient, and development of a highly sensitive two-layer resist has been desired from the viewpoint of improving the throughput (mass productivity) of electronic circuit element production.
【０００４】従って、本発明の目的は酸素プラズマ耐性
が高く、高感度で、二層レジストとして機能するレジス
ト組成物及びそれを用いて高生産性で経済的にパターン
を形成することができるレジストパターンの形成方法を
提供することにある。Accordingly, an object of the present invention is to provide a resist composition having high oxygen plasma resistance, high sensitivity, and functioning as a two-layer resist, and a resist pattern capable of forming a pattern with high productivity and economically using the same. It is an object of the present invention to provide a forming method.
【０００５】[0005]
【課題を解決するための手段】本発明に従えば、炭素数
１〜６のアルコキシシリル基を有する芳香族化合物から
成る架橋剤、酸発生剤、水酸基を有するポリマー及び溶
媒から成るレジスト組成物が提供される。According to the present invention, there is provided a resist composition comprising a crosslinking agent comprising an aromatic compound having an alkoxysilyl group having 1 to 6 carbon atoms, an acid generator, a polymer having a hydroxyl group, and a solvent. Provided.
【０００６】本発明に係るレジスト組成物は、一般的な
方法に従って、有機ポリマーを塗布し、ハードベークし
た基板上に、本発明のレジスト組成物を塗布し、電離放
射線を露光し、ポストエクスポゥジャベーク（ＰＥＢ）
し、現像し、Ｏ2 プラズマによって下層有機ポリマーを
ドライエッチングすることにより二層パターンを形成す
ることができる。The resist composition according to the present invention is prepared by applying the resist composition of the present invention onto a hard-baked substrate after applying an organic polymer according to a general method, exposing the resist composition to ionizing radiation, and then subjecting the resist composition to post-exposure. Jabake (PEB)
Then, development is performed, and the lower organic polymer is dry-etched by O 2 plasma to form a two-layer pattern.
【０００７】本発明に係るレジスト組成物は、露光によ
り酸発生剤から酸が発生し、この酸で、アルコキシシリ
ルベンゼンのアルコキシ基が分解し、水酸基を有するポ
リマーの水酸基と架橋反応を容易に起こすため、高感度
のネガ型レジストとして機能することができる。In the resist composition according to the present invention, an acid is generated from an acid generator upon exposure to light, and the alkoxy group of the alkoxysilylbenzene is decomposed by the acid to easily cause a crosslinking reaction with a hydroxyl group of a polymer having a hydroxyl group. Therefore, it can function as a highly sensitive negative resist.
【０００８】本発明に係るレジスト組成物ではアルコキ
シシリル基を有する芳香族化合物を架橋剤として用いる
ので、得られた架橋ポリマーに、Ｓｉが含まれているた
め、Ｏ2 プラズマ耐性が高く、また、少なくとも６つ以
上のアルコキシを有しているため架橋効率が高く、高感
度を実現できる。In the resist composition according to the present invention, an aromatic compound having an alkoxysilyl group is used as a cross-linking agent. Therefore, since the obtained cross-linked polymer contains Si, the O 2 plasma resistance is high, and Since it has at least 6 or more alkoxy groups, the crosslinking efficiency is high and high sensitivity can be realized.
【０００９】本発明において用いる露光光源としては、
可視光、ＵＶ、ＤＵＶ、Ｘ線、ＥＢ、イオンビーム等の
任意の電離放射線を挙げることができる。The exposure light source used in the present invention includes:
Examples include any ionizing radiation such as visible light, UV, DUV, X-ray, EB, and ion beam.
【００１０】本発明において用いる水酸基含有ポリマー
は、水酸基を有していれば特に限定されるものではない
が、Ｏ2 プラズマ耐性を高くするために、ケイ素含有ポ
リマーを使用するのが望ましい。そのようなポリマーと
しては、例えばポリシロキサン、ポリシルセスキオキサ
ン、ポリシルフェニレンシロキサンなどを挙げることが
できる。水酸基の含有量が、実用感度を得る上で３重量
％以上のものが望ましく、また分子量が1000〜10,000,0
00程度のものが望ましい。分子量が1000未満の場合に
は、耐熱性が悪く、10,000,000を超えると溶解性が悪く
なるおそれがある。本発明の組成物に配合される溶媒と
しては、溶媒として機能するものであれば特に規定はな
いが、一般的にはケトン系、エーテル系、アルコール系
などの溶媒を挙げることができる。The hydroxyl group-containing polymer used in the present invention is not particularly limited as long as it has a hydroxyl group, but it is desirable to use a silicon-containing polymer in order to increase O 2 plasma resistance. Examples of such a polymer include polysiloxane, polysilsesquioxane, and polysilphenylenesiloxane. The hydroxyl group content is preferably 3% by weight or more in order to obtain practical sensitivity, and the molecular weight is preferably from 1,000 to 10,000,000.
About 00 is desirable. When the molecular weight is less than 1,000, heat resistance is poor, and when it exceeds 10,000,000, solubility may be poor. The solvent blended in the composition of the present invention is not particularly limited as long as it functions as a solvent, but generally includes ketone-based, ether-based, and alcohol-based solvents.
【００１１】本発明のレジスト組成物に配合される架橋
剤は炭素数１〜６のアルコキシシリル基を有する芳香族
化合物であれば特に限定されないが、式（Ｉ）：The crosslinking agent used in the resist composition of the present invention is not particularly limited as long as it is an aromatic compound having an alkoxysilyl group having 1 to 6 carbon atoms.
【００１２】[0012]
【化２】 Embedded image
【００１３】（式中、Ｒは、それぞれ独立に、水素、炭
素数１〜５の低級アルキル基、及びアルコキシ基の炭素
数が１〜６のトリアルコキシシリル基を示すが、Ｒのう
ちの少なくとも２つはトリアルコキシシリル基を示す）
で示されるアルコキシシリルベンゼンが特に望ましい。
ここで、アルコキシ基としてはメトキシ、エトキシ、フ
ェノキシなどを挙げることができる。また、酸発生剤と
しては、オニウム塩、イソシアヌレート、ニトロベンジ
ルエステル、スルホン酸エステル、ビスアリールスルホ
ニルジアゾメタンなどを挙げることができる。(Wherein, R independently represents hydrogen, a lower alkyl group having 1 to 5 carbon atoms, and a trialkoxysilyl group having 1 to 6 carbon atoms in an alkoxy group. Two represent trialkoxysilyl groups)
Is particularly desirable.
Here, examples of the alkoxy group include methoxy, ethoxy, and phenoxy. Examples of the acid generator include onium salts, isocyanurates, nitrobenzyl esters, sulfonic esters, and bisarylsulfonyldiazomethanes.
【００１４】本発明のレジスト組成物の各成分の配合比
は、架橋剤／ポリマー／酸発生剤の比は、重量基準で 1
00／50〜 500／１〜100 が好ましく、更に好ましくは 1
00〜／ 100〜 300／５〜30である。溶媒量には特に限定
はなく、レジスト組成物の塗布性などを考慮して適宜決
定することができるが、好ましくは全組成物当り50〜95
重量％である。The compounding ratio of each component of the resist composition of the present invention is such that the ratio of crosslinking agent / polymer / acid generator is 1% by weight.
00/50 to 500/1 to 100 are preferable, and 1 is more preferable.
00 ~ / 100 ~ 300/5 ~ 30. The amount of the solvent is not particularly limited and can be appropriately determined in consideration of the coating properties of the resist composition, but is preferably 50 to 95 per total composition.
% By weight.
【００１５】本発明に係るレジストパターンの形成方法
は、前記した特定のレジストパターンを用いて従来の一
般的な方法に従って実施することができる。その一例を
示せば、スピンコート法等により基板上に 0.1μm 〜 1
00μm の厚さになるように有機レジスト層を塗布し、熱
硬化を行った後、この上にスピンコート法等により本発
明レジスト組成物を0.05〜10μm の厚さになるように塗
布する。25〜 200℃でこれをプリベークし、電子線を照
射後、上層レジストを現像し、この上層パターンをＯ2
−ＲＩＥにより下層へ転写する。The method for forming a resist pattern according to the present invention can be carried out according to a conventional general method using the specific resist pattern described above. As an example, 0.1 μm to 1 μm
An organic resist layer is applied so as to have a thickness of 00 μm, and after thermosetting, the resist composition of the present invention is applied thereon by spin coating or the like so as to have a thickness of 0.05 to 10 μm. Baked this in. 25 to 200 ° C., after irradiation with an electron beam, and developing the top layer resist, the upper layer pattern O 2
-Transfer to lower layer by RIE.
【００１６】[0016]
【実施例】以下、実施例により本発明を具体的に説明す
るが、本発明を以下の実施例に限定するものでないこと
はいうまでもない。EXAMPLES Hereinafter, the present invention will be described in detail with reference to Examples, but it goes without saying that the present invention is not limited to the following Examples.
【００１７】実施例１ 末端に水酸基を有するポリメチルシルフェニレンシロキ
サン（Ｍｗ（平均分子量）＝5000）10重量部に１，４−
ビス（トリエトキシシリル）ベンゼン５重量部及びトリ
ス（２，３−ジブロモプロピル）イソシアヌレート 0.5
重量部を加え、これらをシクロヘキサノン 150重量部に
溶解し、ポアサイズ 0.1μm のメンブランフィルタで濾
過してレジスト溶液とした。 EXAMPLE 1 10 parts by weight of polymethylsilphenylene siloxane having a hydroxyl group at a terminal (Mw (average molecular weight) = 5000) was added to 1,4-
Bis (triethoxysilyl) benzene 5 parts by weight and tris (2,3-dibromopropyl) isocyanurate 0.5
Parts by weight were dissolved in 150 parts by weight of cyclohexanone, and filtered through a membrane filter having a pore size of 0.1 μm to obtain a resist solution.
【００１８】Ｓｉウェハ上にAZ−1350型フォトレジスト
（シプレー社）を１μm の膜厚で塗布し、200 ℃で１時
間ハードベークした後、上記レジストを 0.2μm の膜厚
で塗布し、80℃で１分間プリベーク後、加速電圧30kVで
電子線露光を行い、105 ℃で２分間ＰＥＢを行った。次
に、メチルイソブチルケトン（ＭＩＢＫ）とイソプロピ
ルアルコール（ＩＰＡ）の混合溶媒で現像し、エタノー
ル（EtOH）でリンスを行った。得られた膜を80℃で１分
間ベークし、酸素リアクティブイオンエッチング（Ｏ2
−ＲＩＥ）装置で酸素ガス圧 2.6Pa、ガス流量10sccm、
印加周波数13.56MHz、印加電力密度0.22Ｗ／cm2 の条件
にて上層パターンを下層にエッチングした。その結果、
本レジストは５μＣ／cm2 の露光量で 0.5μm のパター
ンを解像した。AZ-1350 type photoresist (Shipley Co., Ltd.) is coated on a Si wafer at a thickness of 1 μm and hard baked at 200 ° C. for 1 hour. After prebaking for 1 minute at, an electron beam exposure was performed at an acceleration voltage of 30 kV, and PEB was performed at 105 ° C. for 2 minutes. Next, development was performed with a mixed solvent of methyl isobutyl ketone (MIBK) and isopropyl alcohol (IPA), and rinsing was performed with ethanol (EtOH). The obtained film is baked at 80 ° C. for 1 minute and subjected to oxygen reactive ion etching (O 2
-RIE) device with oxygen gas pressure 2.6Pa, gas flow rate 10sccm,
The upper layer pattern was etched into the lower layer under the conditions of an applied frequency of 13.56 MHz and an applied power density of 0.22 W / cm 2 . as a result,
This resist resolved a 0.5 μm pattern at an exposure of 5 μC / cm 2 .
【００１９】実施例２ 末端に水酸基を有するポリメチルシルセスキオキサン
（Ｍｗ（平均分子量）＝6000）10重量部に１，４−ビス
（トリメトキシシリル）ベンゼン５重量部及びトリス
（２，３−ジブロモプロピル）イソシアヌレート 0.5重
量部を加え、これらをシクロヘキサノン 150重量部に溶
解してレジスト溶液とした。Ｓｉウェハ上にAZ−1350型
フォトレジスト（シプレー社）を１μm の膜厚で塗布
し、200 ℃で１時間ハードベークした後、上記レジスト
を 0.2μm の膜厚で塗布し、80℃で１分間プリベーク
後、加速電圧30kVで電子線露光を行い、105 ℃で２分間
ＰＥＢを行った。次に、ＭＩＢＫとＩＰＡの混合溶媒で
現像し、EtOHでリンスを行った。得られた膜を80℃で１
分間ベークし、Ｏ2 −ＲＩＥ装置で上層パターンを下層
にてエッチングした。その結果、本レジストは６μＣ／
cm2 の露光量で 0.5μm のパターンを解像した。 EXAMPLE 2 5 parts by weight of 1,4-bis (trimethoxysilyl) benzene and 10 parts by weight of polymethylsilsesquioxane having a hydroxyl group at a terminal (Mw (average molecular weight) = 6000) and tris (2,3 0.5 part by weight of (-dibromopropyl) isocyanurate was added, and these were dissolved in 150 parts by weight of cyclohexanone to prepare a resist solution. AZ-1350 type photoresist (Shipley Co.) is coated on Si wafer at a thickness of 1 μm and hard baked at 200 ° C. for 1 hour. Then, the resist is coated at a thickness of 0.2 μm and then at 80 ° C. for 1 minute. After pre-baking, electron beam exposure was performed at an acceleration voltage of 30 kV, and PEB was performed at 105 ° C. for 2 minutes. Next, development was performed with a mixed solvent of MIBK and IPA, and rinsing was performed with EtOH. The obtained film is heated at 80 ° C for 1 hour.
After baking for minutes, the upper layer pattern was etched on the lower layer with an O 2 -RIE apparatus. As a result, the resist was 6 μC /
A 0.5 μm pattern was resolved with an exposure of cm 2 .
【００２０】[0020]
【発明の効果】以上説明したように、本発明に係るレジ
スト組成物を用いることにより、僅かな露光量で所望の
パターンを形成することができるようになり、半導体集
積回路等のデバイスのスループット向上に寄与するとこ
ろが非常に大きい。As described above, by using the resist composition according to the present invention, a desired pattern can be formed with a small amount of light exposure, and the throughput of a device such as a semiconductor integrated circuit can be improved. Is very large.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 福田 麻奈美 神奈川県川崎市中原区上小田中1015番地 富士通株式会社内 (56)参考文献 特開 平１−293339（ＪＰ，Ａ) 特開 平２−15270（ＪＰ，Ａ) 特開 平２−23355（ＪＰ，Ａ) 特開 平２−63114（ＪＰ，Ａ) 特開 昭61−261735（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) G03F 7/038 G03F 7/004 G03F 7/075 H01L 21/027 ────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Manami Fukuda 1015 Kamiodanaka, Nakahara-ku, Kawasaki City, Kanagawa Prefecture Inside Fujitsu Limited (56) References JP-A-1-293339 (JP, A) JP-A-2-15270 (JP, A) JP-A-2-23355 (JP, A) JP-A-2-63114 (JP, A) JP-A-61-261735 (JP, A) (58) Fields investigated (Int. Cl. 7) , DB name) G03F 7/038 G03F 7/004 G03F 7/075 H01L 21/027
Claims (4)
する芳香族化合物からなる架橋剤、酸発生剤、水酸基を
有するポリマー及び溶媒から成るレジスト組成物。1. A resist composition comprising a crosslinking agent comprising an aromatic compound having an alkoxysilyl group having 1 to 6 carbon atoms, an acid generator, a polymer having a hydroxyl group, and a solvent.
低級アルキル基、及びアルコキシ基の炭素数が１〜６の
トリアルコキシシリル基を示すが、Ｒのうちの少なくと
も２つはトリアルコキシシリル基を示す）で示されるア
ルコキシシリルベンゼンであり、また水酸基を有するポ
リマーがケイ素含有ポリマーである請求項１記載のレジ
スト組成物。2. The method according to claim 1, wherein the aromatic compound is of the formula (I): (Wherein, R independently represents hydrogen, a lower alkyl group having 1 to 5 carbon atoms, and a trialkoxysilyl group having 1 to 6 carbon atoms in an alkoxy group, wherein at least two of Rs are The resist composition according to claim 1, wherein the alkoxysilylbenzene represented by a trialkoxysilyl group) is used, and the polymer having a hydroxyl group is a silicon-containing polymer.
物を基板上に塗布し、プリベークし、露光し、ポストエ
クスポゥジャベークし、そして現像することを特徴とす
るパターン形成方法。3. A pattern forming method, comprising applying the resist composition according to claim 1 on a substrate, pre-baking, exposing, post-exposure baking, and developing.
物を有機ポリマーを塗布した基板上に塗布し、プリベー
クし、露光し、ポストエクスポゥジャベークし、現像し
て上層をパターニングし、次いでこれをマスクとして下
層の有機ポリマー層へドライエッチング法で転写するこ
とを特徴とするパターン形成方法。4. The resist composition according to claim 1 or 2 is coated on a substrate coated with an organic polymer, pre-baked, exposed, post-exposure baked, developed and patterned to form an upper layer. A pattern forming method, wherein the pattern is transferred to a lower organic polymer layer by dry etching using the mask as a mask.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04063341A JP3132885B2 (en) | 1992-03-19 | 1992-03-19 | Resist composition and pattern forming method using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04063341A JP3132885B2 (en) | 1992-03-19 | 1992-03-19 | Resist composition and pattern forming method using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05265210A JPH05265210A (en) | 1993-10-15 |
| JP3132885B2 true JP3132885B2 (en) | 2001-02-05 |
Family
ID=13226445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP04063341A Expired - Fee Related JP3132885B2 (en) | 1992-03-19 | 1992-03-19 | Resist composition and pattern forming method using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3132885B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7115531B2 (en) | 2000-08-21 | 2006-10-03 | Dow Global Technologies Inc. | Organosilicate resins as hardmasks for organic polymer dielectrics in fabrication of microelectronic devices |
| JP6996411B2 (en) | 2018-04-25 | 2022-01-17 | 株式会社デンソー | Neural network circuit |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5338459B2 (en) * | 2009-04-28 | 2013-11-13 | 住友ベークライト株式会社 | Photosensitive resin composition and semiconductor device |
| JP5740832B2 (en) * | 2009-06-08 | 2015-07-01 | Jsr株式会社 | Radiation-sensitive composition, protective film, interlayer insulating film, and method for forming them |
| JP5729133B2 (en) * | 2010-07-16 | 2015-06-03 | Jsr株式会社 | Radiation-sensitive composition, protective film, interlayer insulating film, and method for forming them |
-
1992
- 1992-03-19 JP JP04063341A patent/JP3132885B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7115531B2 (en) | 2000-08-21 | 2006-10-03 | Dow Global Technologies Inc. | Organosilicate resins as hardmasks for organic polymer dielectrics in fabrication of microelectronic devices |
| US7268200B2 (en) | 2000-08-21 | 2007-09-11 | Dow Global Technologies Inc. | Organosilicate resins as hardmasks for organic polymer dielectrics in fabrication of microelectronic devices |
| JP6996411B2 (en) | 2018-04-25 | 2022-01-17 | 株式会社デンソー | Neural network circuit |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05265210A (en) | 1993-10-15 |
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