JPS63118739A - Process for forming resist pattern - Google Patents

Process for forming resist pattern

Info

Publication number
JPS63118739A
JPS63118739A JP26396186A JP26396186A JPS63118739A JP S63118739 A JPS63118739 A JP S63118739A JP 26396186 A JP26396186 A JP 26396186A JP 26396186 A JP26396186 A JP 26396186A JP S63118739 A JPS63118739 A JP S63118739A
Authority
JP
Japan
Prior art keywords
resist
layer
intermediate layer
resist pattern
pattern
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
Application number
JP26396186A
Other languages
Japanese (ja)
Inventor
Shoji Shiba
昭二 芝
Shunichi Fukuyama
俊一 福山
Yasuhiro Yoneda
泰博 米田
Kazumasa Saito
斎藤 和正
Yoko Kawasaki
陽子 川崎
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujitsu Ltd
Original Assignee
Fujitsu Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Fujitsu Ltd filed Critical Fujitsu Ltd
Priority to JP26396186A priority Critical patent/JPS63118739A/en
Publication of JPS63118739A publication Critical patent/JPS63118739A/en
Pending legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/075Silicon-containing compounds
    • G03F7/0757Macromolecular compounds containing Si-O, Si-C or Si-N bonds

Abstract

PURPOSE:To form a resist pattern having superior definition by providing an intermediate layer comprising a mixture consisting of a specified silicone resin and a monoazide or bisazide compd. to a three layered resist. CONSTITUTION:A mixture consisting of a silicone resin expressed by the formula I with the monoazide or bisazide compd. is used for the intermediate layer of the three layered resist. In the formula I, R is a vinyl or allyl group; n is a positive integer, which is pref. 10-1,000, more pref. 50-500. Suitable material for the lowest layer of the three-layered resist is phenol-novolak resin, etc. On one hand, conventional resist may be used for the upper layer of the resist. By this method, a resist pattern having high resolution power can be formed.

Description

【発明の詳細な説明】 発明の概要 本発明は、半導体装置のパターン形成方法に関し、ラダ
ー構造シリコーン樹脂を三層構造レジストの中間層とし
て使用することにより解像性に優れたレジストパターン
を形成するものである。
DETAILED DESCRIPTION OF THE INVENTION Summary of the Invention The present invention relates to a pattern forming method for semiconductor devices, and involves forming a resist pattern with excellent resolution by using a ladder structure silicone resin as an intermediate layer of a three-layer structure resist. It is something.

産業上の利用分野 本発明は、レジストパターン形成方法に関し、特に半導
体集積回路のレジストパターン形成方法に関する。
INDUSTRIAL APPLICATION FIELD The present invention relates to a resist pattern forming method, and more particularly to a resist pattern forming method for semiconductor integrated circuits.

従来の技術 半導体集積回路の形成には、薄膜形成技術と写真食刻技
術(ホトリソグラフィあるいは電子線リソグラフィ)が
多用されている。これらの技術の進歩によって、半導体
単位素子はますます微細化され、LSI 、 VLSI
のような大容量素子が実用化されている。
2. Description of the Related Art Thin film formation technology and photolithography (photolithography or electron beam lithography) are often used to form semiconductor integrated circuits. With the advancement of these technologies, semiconductor unit elements have become increasingly finer, leading to LSI, VLSI
Large capacitance devices such as these have been put into practical use.

即ち、配線パターンについて言えば、被処理基板上に形
成した配線形成材料からなる薄膜の上にレジストを被覆
し、これに選択的に紫外線露光を施してレジストパター
ンを造り、これにウェットエツチングあるいはドライエ
ツチングを行って微細パターンを形成するパターン形成
法では、波長による制限から微細パターンの形成は1μ
m以上の線幅のパターンに限られ、これ以下の微細パタ
ーンの形成は困難である。
That is, regarding the wiring pattern, a resist is coated on a thin film made of a wiring forming material formed on the substrate to be processed, and this is selectively exposed to ultraviolet light to create a resist pattern, which is then subjected to wet etching or dry etching. In the pattern forming method that forms fine patterns by etching, the formation of fine patterns is limited to 1 μm due to wavelength limitations.
It is limited to patterns with a line width of m or more, and it is difficult to form fine patterns smaller than this.

一方、電子線のような電離放射線は波長が紫外線に比べ
て温かに短いので1μm未満の微細パターンの形成が可
能であり、そのためにVLS Iのような大容量素子の
形成には電子線リソグラフィが使用されている。
On the other hand, since the wavelength of ionizing radiation such as electron beams is warmer and shorter than that of ultraviolet rays, it is possible to form fine patterns of less than 1 μm. Therefore, electron beam lithography is used to form large-capacity devices such as VLSI. It is used.

次に、LSI 、 VLSI等のような半導体素子製造
プロセスにおいては多層化が行われているために基板表
面に1〜2μmの段差を生じることが多く、かかる場合
に従来の単層レジスト法を適用すると微細パターンを高
精度で形成することは不可能になる。
Next, in the manufacturing process of semiconductor devices such as LSI and VLSI, multilayering is performed, which often creates a step difference of 1 to 2 μm on the substrate surface, and in such cases, the conventional single-layer resist method is applied. This makes it impossible to form fine patterns with high precision.

そこで、まず下層レジストを用いて平坦化し、この上に
耐酸素ドライエツチング性の優れた上層レジストを薄く
形成してドライエツチングし、微細パターンを形成する
二層構造レジストあるいは下層レジストを用いて平坦化
し、その上に耐酸素ドライエツチング性の優れた中間層
を形成し、さらにその上に上層レジストを薄く形成して
ドライエツチングし、微細パターンを形成する三層構造
レジストといった多層レジスト法が適用されている。
Therefore, first, a lower layer resist is used for planarization, a thin upper layer resist with excellent oxygen dry etching resistance is formed on top of this, dry etching is performed, and a two layer structure resist or a lower layer resist is used to form a fine pattern for planarization. A multilayer resist method has been applied, such as a three-layer structure resist, in which an intermediate layer with excellent oxygen dry etching resistance is formed on top of this, and a thin upper resist layer is formed on top of that and dry etched to form a fine pattern. There is.

発明が解決しようとする問題点 本発明はかかる三層構造レジストに関するものである。The problem that the invention seeks to solve The present invention relates to such a three-layer structured resist.

高段差をもつ基板上に精度よく微細パターンを形成する
方法として開発されている三層レジストは、下層の平坦
化層レジストと耐酸素プラ、ズマ性に優れる中間層と感
光性または惑電子性をもつ上層レジストから構成されて
いる。
The three-layer resist, which has been developed as a method for forming fine patterns with high precision on substrates with high step differences, consists of a lower layer of flattening resist, an oxygen-resistant plastic, an intermediate layer with excellent smearing properties, and a photosensitive or electrophilic layer. It consists of an upper layer of resist.

ここで、下層レジストの必要条件としては、(1)  
酸素プラズマで容易に劣化し、分解して気化し易いもの
、 (2)平坦化性の優れた材料であること、(3)上層レ
ジストとのなじみの良いこと、などを挙げることができ
、これに通する材料としてフェノールノボラック樹脂な
どがある。また、中間層には、 (1)  耐酸素プラズマ性に優れること、(2)低温
プロセスで形成できること、(3)UV露先により短時
間で硬化できること、(4)  エツチング速度が速い
こと、といった条件が必要である。一方、上層レジスト
には耐酸素プラズマ性は必要なく、従来のレジストが使
用できる。しかし、かかる中間層の必要条件を満足する
材料は未だ実用化されていない。
Here, the necessary conditions for the lower layer resist are (1)
(2) It is a material with excellent planarization properties, and (3) It is compatible with the upper layer resist. There are materials such as phenol novolac resin that can be passed through. In addition, the intermediate layer has the following properties: (1) It has excellent oxygen plasma resistance, (2) It can be formed in a low-temperature process, (3) It can be cured in a short time by UV exposure, and (4) It has a fast etching speed. Conditions are required. On the other hand, oxygen plasma resistance is not required for the upper layer resist, and conventional resists can be used. However, a material that satisfies the requirements for such an intermediate layer has not yet been put into practical use.

本発明の目的は、従って、上記の如き条件を十分に満足
することのできる材料を三層構造レジストの中間層とし
て用いるパターン形成方法を提供することにある。
Therefore, an object of the present invention is to provide a pattern forming method using a material that can fully satisfy the above conditions as an intermediate layer of a three-layer resist.

問題点を解決するための手段 本発明は、下記一般式、 〔上式中、Rはビニル基またはアリル基を表し、nは正
の整数を表す〕 で示されるシリコーン樹脂とモノアジドまたはビスアジ
ド化合物との混合物を三層構造レジストの中間層として
使用することを特徴とする、レジストパターン形成方法
を提供する。
Means for Solving the Problems The present invention provides a silicone resin represented by the following general formula: [In the above formula, R represents a vinyl group or an allyl group, and n represents a positive integer] and a monoazide or bisazide compound. Provided is a method for forming a resist pattern, characterized in that a mixture of the following is used as an intermediate layer of a three-layer resist.

本発明らは、即ち、シリコーンポリマーが耐酸素プラズ
マ性に優れた材料であることに着目し、これに感光性を
付与することにより、優れた三層構造レジスト用の中間
層を提供することができたものである。
Specifically, the present inventors focused on the fact that silicone polymer is a material with excellent oxygen plasma resistance, and by imparting photosensitivity to silicone polymer, it was possible to provide an excellent intermediate layer for a three-layer resist. It was made.

本発明に係る上記一般式において、nは好ましくは10
〜1000であり、さらに好ましくは50〜500であ
る。
In the above general formula according to the present invention, n is preferably 10
-1000, more preferably 50-500.

本発明に有用なモノアジド化合物の例としては、がある
。また、ビスアジド化合物の例としては、いシ! υ■ がある。
Examples of monoazide compounds useful in the present invention include. Also, as an example of a bisazide compound, Ishi! There is υ■.

また、本発明に有用な三層構造レジストの下層レジスト
に適する材料としては、フェノールノボラック樹脂など
がある。一方、上層レジストとしては、従来公知のレジ
ストが使用できる。
Furthermore, materials suitable for the lower layer resist of the three-layer structure resist useful in the present invention include phenol novolak resin. On the other hand, a conventionally known resist can be used as the upper layer resist.

作用 本発明に従って、前述のシリコーン樹脂とモノアジドま
たはビスアジド化合物との混合物を三層構造レジストの
中間層として使用することにより、解像性に優れたレジ
ストパターンの形成を実現することができる。
Function According to the present invention, a resist pattern with excellent resolution can be formed by using a mixture of the silicone resin and a monoazide or bisazide compound as an intermediate layer of a three-layer resist.

実施例 以下に、実施例を挙げて、本発明をさらに説明する。Example The present invention will be further explained below with reference to Examples.

合成例1 メチルイソブチルケトン(MIBK)  100 m 
Ilにトリエチルアミン18m1を加え、ビニルトリク
ロルシラン30gを混合し、次いで一60℃に冷却した
。これにイオン交換水13mj!を滴下した後、反応溶
液を徐々に昇温した。窒素ガスでバブリングを行いなが
ら、120℃で5時間還流し、縮合反応を行った。その
後、反応液を5〜6回水洗し、MIBK層を分取した。
Synthesis Example 1 Methyl isobutyl ketone (MIBK) 100 m
18 ml of triethylamine was added to Il, and 30 g of vinyltrichlorosilane was added thereto, followed by cooling to -60°C. Add this to 13mj of ion exchange water! was added dropwise, the temperature of the reaction solution was gradually raised. While bubbling with nitrogen gas, the mixture was refluxed at 120° C. for 5 hours to perform a condensation reaction. Thereafter, the reaction solution was washed with water 5 to 6 times, and the MIBK layer was separated.

次に、30 m lのピリジンを加え、60℃で3時間
反応させ、未反応水酸基をシリル化した。反応液を10
回水洗した後、アセトニトリルを加え、樹脂を沈澱回収
した。得られた樹脂をベンゼン50mlに溶解し、凍結
乾燥を行った。
Next, 30 ml of pyridine was added and reacted at 60°C for 3 hours to silylate unreacted hydroxyl groups. 10% of the reaction solution
After washing twice with water, acetonitrile was added to precipitate and collect the resin. The obtained resin was dissolved in 50 ml of benzene and freeze-dried.

得られた樹脂はMw=5.OX 10’ 、Mw/Mn
 = 1.8であった。
The obtained resin had Mw=5. OX 10', Mw/Mn
= 1.8.

実施例1 合成例1で得られたシリル化ポリビニルシルセスキオキ
サン1gをMIBK15mlに溶解し、感光剤として4
,4′−ジアジドカルコン0.07gを加え、レジスト
溶液を調製した。
Example 1 1 g of silylated polyvinyl silsesquioxane obtained in Synthesis Example 1 was dissolved in 15 ml of MIBK, and 4
, 0.07 g of 4'-diazide chalcone was added to prepare a resist solution.

添付の第1図に示すようにして、シリコン基板1上に下
層レジスト2として、シラプレー社製マイクロポジット
1350レジストを膜厚2μmとなるように塗布した後
、200℃1時間の加熱を行い硬化させた〔工程(1)
〕。その上に先に調製したレジスト溶液を膜厚0.2μ
mとなるように塗布し、120℃で15分間の溶剤乾燥
の後、UV露光(350nm)により硬化させて、中間
層3を形成した〔工程(2)〕。さらに、上層レジスト
4として、ポジ聖霊子線しジスI−CMR(富士通研究
所)を膜厚が0.2μmとなるように塗布し〔工程f3
))、溶剤乾燥の後、電子線露光および現像を行った〔
工程(4)〕。
As shown in the attached Figure 1, Microposit 1350 resist manufactured by Silaplay Co., Ltd. was coated on the silicon substrate 1 as the lower resist 2 to a thickness of 2 μm, and then heated at 200° C. for 1 hour to harden it. [Process (1)
]. On top of that, apply the previously prepared resist solution to a film thickness of 0.2 μm.
m, and after solvent drying at 120° C. for 15 minutes, it was cured by UV exposure (350 nm) to form the intermediate layer 3 [Step (2)]. Further, as the upper resist 4, a positive Holy Spirit I-CMR (Fujitsu Laboratories) was applied to a film thickness of 0.2 μm [Step f3
)) After solvent drying, electron beam exposure and development were carried out [
Step (4)].

次に、上層レジストパターンをマスクとして、C3F1
1ガスにより中間層のエツチングを行い、上層パターン
を中間層に転写した〔工程(5)〕。さらに、中間層を
マスクとして、酸素ガスにより下層レジストのエツチン
グを行い、中間層パターンを下層に転写した〔工程(6
)〕。このようにして形成されたレジストパターンは、
0.2μmのラインアンドスペースを解像することがで
きた。
Next, using the upper resist pattern as a mask, C3F1
The intermediate layer was etched using 1 gas, and the upper layer pattern was transferred to the intermediate layer [Step (5)]. Furthermore, using the intermediate layer as a mask, the lower resist layer was etched with oxygen gas, and the intermediate layer pattern was transferred to the lower layer [Step (6)
)]. The resist pattern formed in this way is
It was possible to resolve lines and spaces of 0.2 μm.

発明の効果 本発明によれば、高解像度のレジストパターンの形成を
実現することができる。
Effects of the Invention According to the present invention, it is possible to form a resist pattern with high resolution.

【図面の簡単な説明】[Brief explanation of the drawing]

第1図は、本発明の方法による三層構造レジストのパタ
ーン形成方法を示す工程図である。
FIG. 1 is a process diagram showing a method for forming a pattern of a three-layer resist according to the method of the present invention.

Claims (1)

【特許請求の範囲】 1、下記一般式、 ▲数式、化学式、表等があります▼ 〔上式中、Rはビニル基またはアリル基を表し、nは正
の整数を表す〕 で示されるシリコーン樹脂とモノアジドまたはビスアジ
ド化合物との混合物を三層構造レジストの中間層として
使用することを特徴とする、レジストパターン形成方法
[Claims] 1. A silicone resin represented by the following general formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the above formula, R represents a vinyl group or an allyl group, and n represents a positive integer] 1. A method for forming a resist pattern, comprising using a mixture of and a monoazide or bisazide compound as an intermediate layer of a three-layer resist.
JP26396186A 1986-11-07 1986-11-07 Process for forming resist pattern Pending JPS63118739A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP26396186A JPS63118739A (en) 1986-11-07 1986-11-07 Process for forming resist pattern

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP26396186A JPS63118739A (en) 1986-11-07 1986-11-07 Process for forming resist pattern

Publications (1)

Publication Number Publication Date
JPS63118739A true JPS63118739A (en) 1988-05-23

Family

ID=17396640

Family Applications (1)

Application Number Title Priority Date Filing Date
JP26396186A Pending JPS63118739A (en) 1986-11-07 1986-11-07 Process for forming resist pattern

Country Status (1)

Country Link
JP (1) JPS63118739A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02251961A (en) * 1989-03-27 1990-10-09 Matsushita Electric Ind Co Ltd Fine pattern forming material and pattern forming method
US6743885B2 (en) 2001-07-31 2004-06-01 Sumitomo Chemical Company, Limited Resin composition for intermediate layer of three-layer resist

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02251961A (en) * 1989-03-27 1990-10-09 Matsushita Electric Ind Co Ltd Fine pattern forming material and pattern forming method
US6743885B2 (en) 2001-07-31 2004-06-01 Sumitomo Chemical Company, Limited Resin composition for intermediate layer of three-layer resist

Similar Documents

Publication Publication Date Title
US7862989B2 (en) Method for fabricating dual damascene structures using photo-imprint lithography, methods for fabricating imprint lithography molds for dual damascene structures, materials for imprintable dielectrics and equipment for photo-imprint lithography used in dual damascene patterning
JP2005115380A (en) Silicon-containing composition for spin-on antireflection coating (arc)/hard mask
JPH02294651A (en) Negative type photoresist and use thereof
JPWO2006132088A1 (en) Lithographic coating-type underlayer film forming composition containing naphthalene resin derivative
JPH04366958A (en) Radiation sensitive resin composition
JPH03261952A (en) Resist composition and formation of pattern
JPS63118739A (en) Process for forming resist pattern
US3669662A (en) Cyclic polyisoprene photoresist compositions
JPS63279245A (en) Negative resist composition
KR100783064B1 (en) Organosilane composition, Hardmask Composition Coated under Photoresist and Process of producing integrated circuit devices using thereof
JP2648004B2 (en) Etching resistant pattern forming method
JPS6256947A (en) Composition for flattened layer for resist having two-layered structure
JPS62276543A (en) Pattern forming method
JPS62299965A (en) Negative type resist composition
JPH05216232A (en) Resist composition and method for forming resist pattern
JPS60254036A (en) Formation of pattern
JPH0334055B2 (en)
JPH0477899B2 (en)
JPS62222247A (en) Positive photoresist material
JPH03123355A (en) Resist composition and manufacture of semiconductor device
JPS60206135A (en) Pattern forming process
JPH0272361A (en) Electron ray resist having two-layered structure
JPS63301943A (en) Negative type resist composition having two layer structure
JPH02103546A (en) Electron beam resist composition
JPS60116132A (en) Forming method of negative type resist pattern