JPH022563A - Resist and pattern forming method - Google Patents
Resist and pattern forming methodInfo
- Publication number
- JPH022563A JPH022563A JP63148671A JP14867188A JPH022563A JP H022563 A JPH022563 A JP H022563A JP 63148671 A JP63148671 A JP 63148671A JP 14867188 A JP14867188 A JP 14867188A JP H022563 A JPH022563 A JP H022563A
- Authority
- JP
- Japan
- Prior art keywords
- resist
- development
- vapor phase
- polymer
- additive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 229920000642 polymer Polymers 0.000 claims abstract description 13
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000654 additive Substances 0.000 claims abstract description 10
- 230000000996 additive effect Effects 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 239000007789 gas Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 2
- 239000012808 vapor phase Substances 0.000 abstract description 9
- 230000008961 swelling Effects 0.000 abstract description 6
- 238000001015 X-ray lithography Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000000609 electron-beam lithography Methods 0.000 abstract description 2
- 238000010894 electron beam technology Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001459 lithography Methods 0.000 description 4
- 239000012495 reaction gas Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical group ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- RBZMSGOBSOCYHR-UHFFFAOYSA-N 1,4-bis(bromomethyl)benzene Chemical group BrCC1=CC=C(CBr)C=C1 RBZMSGOBSOCYHR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
Landscapes
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
Description
【発明の詳細な説明】
〔概要〕
リソグラフィ工程に用いるレジスト及びレジストパター
ンの形成方法に関し。DETAILED DESCRIPTION OF THE INVENTION [Summary] This invention relates to a resist used in a lithography process and a method for forming a resist pattern.
気相現像法及び気相現像の可能なレジストを得ることに
より、従来の現像におけるレジストの膨潤の問題を解決
して微細パターンを形成することを目的とし。The aim is to solve the problem of resist swelling in conventional development and form fine patterns by using a vapor phase development method and by obtaining a resist that can be developed in the vapor phase.
分子中に二重結合又は三重結合を持つポリマーと、ハロ
ゲン及び芳香族環で置換されたメタン又はその誘導体を
分子構成要素として持つ付加剤との混合物よりなるレジ
スト、又は、このレジストを露光した後、酸素を含むガ
スのプラズマの下流で現像するパターン形成方法により
構成する。A resist consisting of a mixture of a polymer having a double bond or triple bond in the molecule and an additive having methane or its derivative substituted with a halogen and an aromatic ring as a molecular constituent, or after exposing this resist to light. , a pattern forming method in which development is performed downstream of oxygen-containing gas plasma.
本発明は集積回路（ＩＣ）製造プロセスのりソゲラフイ
エ程に用いるレジスト及びレジストパターンの形成方法
に関する。The present invention relates to a resist used in an integrated circuit (IC) manufacturing process and a method for forming a resist pattern.
近年、 ｉｃの高集積化に伴い、それを構成するパター
ンは微細化され、サブミクロン台の微細パターンが要求
されている。In recent years, as ICs have become highly integrated, the patterns constituting them have become finer, and fine patterns on the submicron scale are now required.
このような微細化に対応するりソグラフィ技術において
は、高精度のレジストパターンの形成が必要となる。In lithography technology that supports such miniaturization, it is necessary to form resist patterns with high precision.
従来のレジストのパターニングは露光後、溶媒によって
現像していた。Conventional resist patterning involves developing with a solvent after exposure.
ところが、溶媒による現像では、溶媒現像特有のレジス
トの膨潤により、現像後においてパターンの間にスカム
或いはブリッジが残る等の問題があり、微細パターンの
形成は困難である。However, in solvent development, there are problems such as scum or bridges remaining between patterns after development due to the swelling of the resist peculiar to solvent development, making it difficult to form fine patterns.
特に、微細パターン形成を目標とする電子線。In particular, electron beams are used to form fine patterns.
Ｘ ′！ｒ：Ａ等のりソグラフィにおいては上記の問題
はプロセス上の大きな障害となっている。X'! In lamination lithography such as r:A, the above-mentioned problem is a major obstacle in the process.
本発明は、気相における現像法及び気相現像の可能なレ
ジストを得ることにより、前記の現像後のレジストの膨
潤の問題を解決し、電子線、Ｘ線等のりソグラフィにお
ける微細パターンの形成を改善することを目的とする。The present invention solves the problem of the swelling of the resist after development by using a gas phase development method and providing a resist that can be developed in the gas phase, thereby facilitating the formation of fine patterns in lamination lithography such as electron beams and X-rays. The purpose is to improve.
上記課題の解決は９分子中に二重結合又は三重結合を持
つポリマーと、ハロゲン及び芳香族環で置換されたメタ
ン又はその誘導体を分子構成要素として持つ付加剤との
混合物よりなるレジスト。The solution to the above problem is a resist made of a mixture of a polymer having nine double or triple bonds in its molecules and an additive having methane or a derivative thereof substituted with a halogen and an aromatic ring as a molecular component.
又は、該レジストを露光した後、酸素を含むガスのプラ
ズマの下流で現像するパターン形成方法により達成され
る。Alternatively, this can be achieved by a pattern forming method in which the resist is exposed and then developed downstream of plasma of an oxygen-containing gas.
第１図（１１は付加剤の一般式を示す図である。FIG. 1 (11 is a diagram showing the general formula of the additive.
図は芳香族環としてベンゼン環を用いた例を示す。The figure shows an example using a benzene ring as the aromatic ring.
クロロメチルベンゼン等のハロゲン及びベンゼンで置換
されたメタンは電子線、Ｘ線等の放射線照射によ・す、
第１図（２）に示される式のようにノ＼ロゲンが遊離し
てラジカルが生成する。Methane substituted with halogens such as chloromethylbenzene and benzene is subject to radiation irradiation such as electron beams and X-rays.
As shown in the formula shown in FIG. 1 (2), norogen is liberated and radicals are generated.
この反応は不対電子がベンゼン環に非局在化するので生
成したラジカルは安定化される効果により効率良く反応
が進む（１）
こうして生じたラジカルはポリマーの二重結合或いは三
重結合の部分に付加される。この結果露光された領域は
ベンゼン環及びハロゲンを含むので、０□／ＣＦ４プラ
ズマの下流で現像した場合エツチングレートが遅くなり
（２）、その結果ネガパターンとして残る。このプロセ
スは気相現像であるのでレジストは膨潤しない。In this reaction, the unpaired electron is delocalized in the benzene ring, so the generated radical is stabilized and the reaction progresses efficiently (1) The generated radical is attached to the double bond or triple bond of the polymer. will be added. Since the resulting exposed area contains benzene rings and halogens, the etching rate will be slow when developed downstream of the 0□/CF4 plasma (2), resulting in a negative pattern remaining. Since this process is a vapor phase development, the resist does not swell.
注（１）：
ラジカル（ベンゼン環−ＣＨｚ・）は反応中間体である
が、この中間体が安定かどうかは反応速度に大きな彫り
を与える。即ち２中間体が不安定であればＣＩ・との再
結合等で元に戻ってしまい、ポリマーとの反応は進まな
くなる。反応はポリマーとラジカルが衝突して始めて起
こるので、それまでの時間ラジカルは安定に存在する必
要がある。そのラジカルの安定性は不対電子が非局在化
するとき量子的効果により安定性が増すことは良く知ら
れている。Note (1): The radical (benzene ring -CHz.) is a reaction intermediate, but whether or not this intermediate is stable has a large impact on the reaction rate. That is, if the two intermediates are unstable, they will return to their original state due to recombination with CI, etc., and the reaction with the polymer will not proceed. Since the reaction occurs only when the polymer and the radical collide, the radical must remain stable until then. It is well known that the stability of the radical increases due to quantum effects when the unpaired electron becomes delocalized.
注（２）： ベンゼンは非常に安定な分子で酸化され難＜。Note (2): Benzene is a very stable molecule and is difficult to oxidize.
又ハロゲンを含む分子もハロゲンの電子親和力が酸素よ
り大きいため酸化され難い性質がある。現像は酸素ラジ
カルによる酸化過程であるから、ベンゼン環又はハロゲ
ンを含む分子はエツチングレートが小さい。Molecules containing halogen also have the property of being difficult to oxidize because halogen has a higher electron affinity than oxygen. Since development is an oxidation process using oxygen radicals, molecules containing benzene rings or halogens have a low etching rate.
実施例（１）
レジストは
ポリマー：ポリ−２，３−ジメチルブタジェンと付加剤
：α、α′−ジクロローｐ−キシレンの１：１の混合物
を用いる。Example (1) The resist uses a 1:1 mixture of a polymer: poly-2,3-dimethylbutadiene and an additive: α,α'-dichloro-p-xylene.
電子綿で露光した後１図示の装置を用いて０□とＣＦ４
の混合ガスのプラズマの下流で現像した。After exposure with electronic cotton, 0□ and CF4 using the apparatus shown in Figure 1.
Developed downstream of a mixed gas plasma.
現像条件は Ｏｚ ： １０００ ＳＣＣＭ、 ＣＦ４
： ２００ ＳＣＣＭ。Development conditions: Oz: 1000 SCCM, CF4
: 200 SCCM.
圧カニ ６ Ｔｏｒｒ、 μ波型カニ７５０讐であ
る。Pressure crab 6 Torr, μ wave type crab 750mm.
結果は、パターンの残膜率８０％、露光感度８００μＣ
／ｃｌＩｌｚ、解像度０．５．ｃｚｍが得られた。The result was a pattern residual rate of 80% and an exposure sensitivity of 800μC.
/clIlz, resolution 0.5. czm was obtained.
実施例（２）
Ｘ線露光を用い、実施例（１）と同じレジスト、現像条
件で処理した。Example (2) Processing was carried out using X-ray exposure under the same resist and development conditions as in Example (1).
結果は、残膜率８０％、感度５００ｍＪ／ｃｍ２．解像
度０．４μｍが得られた。The results showed a residual film rate of 80% and a sensitivity of 500 mJ/cm2. A resolution of 0.4 μm was obtained.
実施例（３）
レジストは
ポリマー：ポリ−２，３−ジメチルブタジェン付加剤ニ
トリフェニルクロライド
の１：１の混合物を用いる。Example (3) The resist uses a 1:1 mixture of polymer:poly-2,3-dimethylbutadiene adduct nitriphenyl chloride.
電子線で露光した後、実施例（１）と同じ条件で現像し
た。After exposure to an electron beam, development was performed under the same conditions as in Example (1).
結果は、残膜率７０％、感度１０００ ｉｔ Ｃ／ｃｍ
２．解像度０．４μｍが得られた。The result is a residual film rate of 70% and a sensitivity of 1000 it C/cm.
2. A resolution of 0.4 μm was obtained.
実施例（４）
レジストは
ポリマー：ポリ−２，３−ジメチルブタジェン付加剤：
１．１−ジクロロ−１−フェニルエタンの１：１の混合
物を用いる。Example (4) Resist is polymer: Poly-2,3-dimethylbutadiene additive:
A 1:1 mixture of 1.1-dichloro-1-phenylethane is used.
電子線で露光した後、実施例（１）と同じ条件で現像し
た。After exposure to an electron beam, development was performed under the same conditions as in Example (1).
結果は、残膜率７５％、感度７００μＣ／ｃｍ”、解像
度０．４μｍが得られた。As a result, a residual film rate of 75%, a sensitivity of 700 μC/cm'', and a resolution of 0.4 μm were obtained.
実施例（５）
レジストは
ポリマー：ポリ−２，３−ジメチルブタジェン付加剤：
α、α′−ジブロモーｐ−キシレンのｌ：ｌの混合物を
用いる。Example (5) Resist is polymer: Poly-2,3-dimethylbutadiene additive:
A l:l mixture of α,α'-dibromo p-xylene is used.
電子線で露光した後、実施例（１）と同じ条件で現像し
た。After exposure to an electron beam, development was performed under the same conditions as in Example (1).
結果は、残膜率７０％、感度７００μＣ／ｃｍ”、解像
度０．５μｍが得られた。As a result, a residual film rate of 70%, a sensitivity of 700 μC/cm'', and a resolution of 0.5 μm were obtained.
実施例（６）
レジストは
ポリマー：ポリ（１メチレ、２−トリメチルシリル）ア
セチレン
付）ＲＩ 剤：α、α′−ジクロローｐ−キシレンの１
：１の混合物を用いる。Example (6) Resist is polymer: poly(1 methylene, 2-trimethylsilyl) with acetylene) RI agent: α, α′-dichloro p-xylene 1
:Use a mixture of 1.
電子線で露光した後２図示の装置を用いて０□とＣＦ４
の混合ガスのプラズマの下流で現像した。After exposure to electron beam, 0□ and CF4
Developed downstream of a mixed gas plasma.
現像条件は０□： １０００ ＳＣＣＭ、 ＣＦ、 ：
５００ ＳＣＣＭ。Development conditions are 0□: 1000 SCCM, CF, :
500 SCCM.
圧カニ ５Ｔｏｒｒ＋ ／’波電カニ７５０Ｗである
。Pressure crab 5Torr+/' wave electric crab 750W.
結果は、残膜率８０％、感度１０００ ＃ Ｃ７ｃｍ”
、解像度０．５μｍが得られた。The results are: 80% residual film rate, sensitivity 1000 #C7cm”
, a resolution of 0.5 μm was obtained.
以上諸実施例において、膨潤のないサブミクロンの微細
パターンが得られた。In the above examples, submicron fine patterns without swelling were obtained.
実施例においては、芳香族環としてベンゼン環を用いた
が、これの代わりにピリジン環等を用いても同様の効果
が得られる。In the examples, a benzene ring was used as the aromatic ring, but the same effect can be obtained by using a pyridine ring instead.
第２図は実施例の現像に用いた装置の模式断面図である
。FIG. 2 is a schematic cross-sectional view of the apparatus used for development in the example.
図において１反応ガス（０２／ＣＰ、の混合ガス）はガ
ス導入口１よりプラズマ室２内に導入され。In the figure, one reaction gas (a mixed gas of 02/CP) is introduced into a plasma chamber 2 through a gas introduction port 1.
方μ波ハマグネトロン４より導波管を経てプラズマ室２
内に導入され、ここで反応ガスのプラズマを発生する。From the μ-wave magnetron 4 to the plasma chamber 2 via the waveguide
The reactant gas is introduced into the reactor, where it generates a plasma of the reactant gas.
３はμ波のチューニングをとるスリータブチューナであ
る。3 is a three-tab tuner that tunes μ waves.
ここで、プラズマは網状のμ波シールド板５があるので
シールド仮５より上に閉じ込められ、プラズマ室２より
下には中性の活性種（主にラジカル）のみが４き出され
、その下流の現像室６内に置かれたウェハ７上に被着さ
れたレジストを現像する。Here, the plasma is confined above the temporary shield 5 because of the net-shaped μ-wave shield plate 5, and only neutral active species (mainly radicals) are ejected below the plasma chamber 2, and the downstream The resist deposited on the wafer 7 placed in the developing chamber 6 is developed.
現像中、現像室６は真空排気口８より排気されて１反応
ガスの圧力を所定の値に保つようにしている。During development, the developing chamber 6 is evacuated from the vacuum exhaust port 8 to maintain the pressure of one reaction gas at a predetermined value.
以上説明したように本発明によれば、気相現像法及び気
相現像の可能なレジストを得ることができ、従来の現像
におけるレジストの膨潤の問題を解決し、電子線、Ｘ線
のりソグラフィによる微細パターンの形成が可能となる
。As explained above, according to the present invention, it is possible to obtain a resist that can be developed using a vapor phase development method and a vapor phase development method, which solves the problem of resist swelling in conventional development, and which can be applied by electron beam or X-ray lithography. It becomes possible to form fine patterns.
第１図（１１，＋２１は付加剤の一般式及び反応式を示
す図。
第２図は実施例の現像に用いた装置の模式断面図である
。
図において。
■は反応ガスの導入口。
２はプラズマ室
３はスリータブチューナ。
４はマグネトロン。
５はμ波シールド板。
６は現像室。
７はウェハ。
８は真空排気口
イ汁力口＊ｊ の−股上Ｎ、
イオ〃口斉］の一抱史量（Ｆミ１７・・反ボＳゴＸｔ罰
く１すじ昌・巌
霞Fig. 1 (11, +21 is a diagram showing the general formula and reaction formula of the additive agent. Fig. 2 is a schematic cross-sectional view of the apparatus used for the development of the example. In the figure. (2) is the inlet for the reaction gas. 2 is a plasma chamber 3 is a sleeve tab tuner. 4 is a magnetron. 5 is a μ-wave shield plate. 6 is a developing chamber. 7 is a wafer. 8 is a vacuum exhaust port and a drain port. ] Ippou history amount (F Mi 17...Anti-Boss Go Xt Punishment 1 Sujimasa, Iwakasumi
Claims (2)
、ハロゲン及び芳香族環で置換されたメタン又はその誘
導体を分子構成要素として持つ付加剤との混合物よりな
ることを特徴とするレジスト。(1) A resist comprising a mixture of a polymer having a double bond or triple bond in its molecule and an additive having methane or a derivative thereof substituted with a halogen and an aromatic ring as a molecular constituent.
を含むガスのプラズマの下流で現像することを特徴とす
るパターン形成方法。(2) A pattern forming method, which comprises exposing the resist according to claim (1) and then developing it downstream of plasma of a gas containing oxygen.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63148671A JPH022563A (en) | 1988-06-16 | 1988-06-16 | Resist and pattern forming method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63148671A JPH022563A (en) | 1988-06-16 | 1988-06-16 | Resist and pattern forming method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH022563A true JPH022563A (en) | 1990-01-08 |
Family
ID=15458015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63148671A Pending JPH022563A (en) | 1988-06-16 | 1988-06-16 | Resist and pattern forming method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH022563A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6121155A (en) * | 1998-12-04 | 2000-09-19 | Advanced Micro Devices | Integrated circuit fabrication critical dimension control using self-limiting resist etch |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57178236A (en) * | 1981-04-28 | 1982-11-02 | Japan Synthetic Rubber Co Ltd | Photo-cross-linking material |
| JPS6315240A (en) * | 1986-07-08 | 1988-01-22 | Fujitsu Ltd | Patterning method and resist |
| JPS6315244A (en) * | 1986-07-08 | 1988-01-22 | Fujitsu Ltd | Patterning method and resist |
-
1988
- 1988-06-16 JP JP63148671A patent/JPH022563A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57178236A (en) * | 1981-04-28 | 1982-11-02 | Japan Synthetic Rubber Co Ltd | Photo-cross-linking material |
| JPS6315240A (en) * | 1986-07-08 | 1988-01-22 | Fujitsu Ltd | Patterning method and resist |
| JPS6315244A (en) * | 1986-07-08 | 1988-01-22 | Fujitsu Ltd | Patterning method and resist |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6121155A (en) * | 1998-12-04 | 2000-09-19 | Advanced Micro Devices | Integrated circuit fabrication critical dimension control using self-limiting resist etch |
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