JPH012034A - photoresist composition - Google Patents
photoresist compositionInfo
- Publication number
- JPH012034A JPH012034A JP62-159177A JP15917787A JPH012034A JP H012034 A JPH012034 A JP H012034A JP 15917787 A JP15917787 A JP 15917787A JP H012034 A JPH012034 A JP H012034A
- Authority
- JP
- Japan
- Prior art keywords
- alkali
- light
- absorbing agent
- soluble
- photoresist composition
- 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
- 239000000203 mixture Substances 0.000 title claims description 21
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 20
- 239000006096 absorbing agent Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 7
- 230000035945 sensitivity Effects 0.000 description 11
- 239000000975 dye Substances 0.000 description 10
- 229920003986 novolac Polymers 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 239000000758 substrate Substances 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229940100630 metacresol Drugs 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 1
- SRJCJJKWVSSELL-UHFFFAOYSA-N 2-methylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(C)=CC=C21 SRJCJJKWVSSELL-UHFFFAOYSA-N 0.000 description 1
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical compound [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- -1 naphthoquinone diazide compound Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、ポジ型フォトレジスト組成物に関するもので
ある。さらに詳しくは、ＩＣやＬＳＩ等の半導体デバイ
スの製造において、アルミニウム等の高反射率基板上で
の微細パターンの形成に特に好適に用いられるフォトレ
ジスト組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a positive photoresist composition. More specifically, the present invention relates to a photoresist composition that is particularly suitable for forming fine patterns on high reflectance substrates such as aluminum in the production of semiconductor devices such as ICs and LSIs.
〈従来の技術〉
従来、ＬＳＩ等の集積回路製造において、キノンジアジ
ド系感光剤とノボラック系樹脂からなる組成物や、ビス
アジド系感光剤と環化ゴム系樹脂からなる組成物等が用
いられている。<Prior Art> Conventionally, in the manufacture of integrated circuits such as LSIs, compositions made of a quinone diazide photosensitizer and a novolac resin, compositions made of a bisazide photosensitizer and a cyclized rubber resin, etc. have been used.
集積回路の製造の際、各種基板上にフォトレジストを使
って微細パターンを形成するが、アルミニウム、アルミ
ニウムーシリコン、ポリシリコン等の高反射率基板上で
は、従来のレジストでは、基板面や段差側面での光の反
射による不必要な領域の感光現象が生じ、いわゆるノツ
チング、ハレーションといった問題を生じる。When manufacturing integrated circuits, photoresists are used to form fine patterns on various substrates, but on high-reflectivity substrates such as aluminum, aluminum-silicon, and polysilicon, conventional resists cannot be used to form fine patterns on the substrate surface or the side surfaces of steps. Due to the reflection of light at the surface, unnecessary areas are exposed to light, resulting in problems such as so-called notching and halation.
このため、特公昭５１−３７５６２号公報に紫外線領域
に吸光特性を有する下記式
に示す染料（オイルイエロー（Ｃ，ｆ、−１１０２０１
＞を吸光剤として含有させ、フォトレジスト店の光透過
性を減少させ、基板表面で反射してフォトレジスト層を
透過する光を急激に低減させ、遮光領域への光の回り込
みを少なくして前記問題を改良し、解像度の低下を防止
する方法が提案されている。For this reason, Japanese Patent Publication No. 51-37562 discloses a dye (Oil Yellow (C, f, -110201
> as a light absorbing agent to reduce the light transmittance of the photoresist layer, sharply reduce the light reflected on the substrate surface and transmitted through the photoresist layer, and reduce the light going around to the light-blocking area. Methods have been proposed to improve the problem and prevent resolution degradation.
しかしながら、この方法では、−船釣に感度が低く、ス
カム等が発生したり、あるいは感度は良いが、残膜率が
低下し、解像度も悪化するといった問題点があった。However, with this method, there are problems in that the sensitivity is low for boat fishing and scum etc. occur, or the sensitivity is good but the remaining film rate is reduced and the resolution is also deteriorated.
〈発明が解決しようとする問題点〉
本発明の目的は、前記従来技術の欠点を除去し、高反射
率基板上で、ハレーションやノツチングのない高解像度
のパターンを形成する高感度７なレジスト組成物を提供
することにある。<Problems to be Solved by the Invention> An object of the present invention is to eliminate the drawbacks of the prior art and to provide a highly sensitive resist composition that forms a high resolution pattern without halation or notching on a high reflectance substrate. It's about providing things.
く問題を解決するための手段〉
本発明者等は、鋭意検討の結果、吸光剤にさらに現像液
であるアルカリに対する溶解性が該吸光剤と反対の化合
物（吸光剤である場合も含む）を併用することにより、
従来技術の有する欠点を一挙に解決することを見出し、
本発明を完成するに至った。As a result of intensive studies, the present inventors have added a compound (including cases where it is a light absorbing agent) to the light absorbing agent, the solubility of which is opposite to that of the light absorbing agent in the alkali developer. By using together,
Discovered that all the shortcomings of the conventional technology could be solved at once,
The present invention has now been completed.
すなわち、本発明は、吸光剤を含有してなるポジ型フォ
トレジスト組成物において、該吸光剤がアルカリ可溶性
である場合にはさらに１種または２種以上のアルカリ不
溶性の化合物を含有し、該吸光剤がアルカリ不溶性であ
る場合には、さらに１種または２種以上のアルカリ可溶
性の化合物を含有してなることを特徴とするフォトレジ
スト組成物である。That is, the present invention provides a positive photoresist composition containing a light absorbing agent, which further contains one or more alkali-insoluble compounds when the light absorbing agent is alkali-soluble; When the agent is alkali-insoluble, the photoresist composition further contains one or more alkali-soluble compounds.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明に用いられるポジ型フォトレジスト組成物の基材
となるフォトレジストとしては、例えばフェノール類と
ホルムアルデヒドを付加縮合反応させて得られるノボラ
ック樹脂とナフトキノンジアジド化合物からなる組成物
が好適に用いられる。なかでもｍ−クレゾール及び／又
はｐ−クレゾールとホルマリンより合成されるクレゾー
ルノボラック樹脂或いはｍ−１ｐ−クレゾール及び３゜
５−キシレノールとホルマリンより合成されるクレゾー
ル系ノボラック樹脂等と２．３．４−トリヒドロキシベ
ンゾフェノン、２．３．４．４’ −テトラヒドロキ
シベンゾフェノン、２．２°、４．４°−テトラヒドロ
キシベンゾフェノン、２゜３．３°、４−テトラヒドロ
キシベンゾフェノン、２．２°、３，４．５° −ペン
タヒドロキシベンゾフェノン、２．３．３°、４．５°
−ペンタヒドロキシベンゾフェノン、２．３．３’、
４゜４°−ペンタヒドロキシベンゾフェノン、２．２゜
、３．４．４° −ペンタヒドロキシベンゾフェノン、
２．２’、３．３’、４−ペンタヒドロキシベンゾフェ
ノン等のポリヒドロキシベンゾフェノン類のナフトキノ
ン−１，２−ジアジドスルホン酸エステルとを含有する
ポジ型フォトレジストが好適に用いられる。As the photoresist serving as the base material of the positive photoresist composition used in the present invention, for example, a composition consisting of a novolak resin obtained by addition-condensation reaction of phenols and formaldehyde and a naphthoquinone diazide compound is suitably used. Among them, cresol novolac resin synthesized from m-cresol and/or p-cresol and formalin, or cresol novolac resin synthesized from m-1p-cresol, 3°5-xylenol and formalin, etc. 2.3.4- Trihydroxybenzophenone, 2.3.4.4'-tetrahydroxybenzophenone, 2.2°, 4.4°-tetrahydroxybenzophenone, 2°3.3°, 4-tetrahydroxybenzophenone, 2.2°, 3 , 4.5° -pentahydroxybenzophenone, 2.3.3°, 4.5°
-pentahydroxybenzophenone, 2.3.3',
4゜4゜-pentahydroxybenzophenone, 2.2゜, 3.4.4゜-pentahydroxybenzophenone,
A positive photoresist containing naphthoquinone-1,2-diazide sulfonic acid ester of polyhydroxybenzophenones such as 2.2', 3.3', and 4-pentahydroxybenzophenone is preferably used.
本発明に云うアルカリ可溶性の吸光剤とは、発色母体に
アルカリ可溶性基（例えばＯＨ基、５Ｏ３Ｈ基、Ｃ０Ｏ
Ｈ基等）をもっている色素をいう。The alkali-soluble light-absorbing agent referred to in the present invention refers to an alkali-soluble light-absorbing agent containing an alkali-soluble group (for example, OH group, 5O3H group, COO
A dye that has a H group, etc.).
さらに具体的には、５５０ｎｍ以下、より好ましくは４
００〜５００ｎｍの領域の光に対して吸収極大をもつ色
素が好ましい。More specifically, 550 nm or less, more preferably 4
Preferably, the dye has an absorption maximum for light in the range of 00 to 500 nm.
本発明におけるアルカリ可溶性は、通常フォトレジスト
の現象に用いる有機アルカリ液または無機アルカリ液（
例えば、テトラメチルアンモニウムハイドロオキサイド
、コリン、水酸化ナトリウム、水酸化カリウム等）に対
して発現されることを意味する。In the present invention, alkali solubility refers to an organic alkali solution or an inorganic alkali solution (usually used for photoresist phenomena).
For example, it means expressed against tetramethylammonium hydroxide, choline, sodium hydroxide, potassium hydroxide, etc.).
吸光剤がアルカリ不溶性である場合に併用するアルカリ
可溶性の化合物として、ここでいうアルカリ可溶性の吸
光剤を用いることもできる。When the light absorbing agent is alkali-insoluble, the alkali-soluble light absorbing agent referred to herein can also be used as the alkali-soluble compound used together.
以下、具体的にアルカリ可溶性の吸光剤を例示するが、
本発明はこれらに限定されるものではなく、また２種以
上を用いることもできる。Hereinafter, specific examples of alkali-soluble light absorbers are given,
The present invention is not limited to these, and two or more types can also be used.
具体的には、ピラゾロンアゾ系色素 ＣＨ２ ＣＩ＋３ ＣＨ。Specifically, pyrazolone azo dyes CH2 CI+3 CH.
ＤＤＨ ＣＨ。DDH CH.
ＣＨ３ キノリンアゾ系色素 ＣＨｌ ＣＩ。CH3 quinoline azo dye CHl C.I.
モノアゾベンゼン系色素 キノフタロン系色素 チアゾールアゾ系色素 等をあげることができる。Monoazobenzene dye Quinophthalone dye Thiazole azo dye etc. can be given.
本発明でＣ）う、アルカリ不溶性の吸光剤とは、発色母
体にアルカリ可溶性の基を持たない色素、さらには、５
５０ ｎｍ以下、より好ましくは４００〜５００ ｎｍ
の領域の光に対して吸収極大をもつ色素が好ましい。ま
た、２種以上の色素を併用してもちろんさしつかえない
。In the present invention, the alkali-insoluble light-absorbing agent C) refers to a dye that does not have an alkali-soluble group in its coloring matrix, and furthermore, 5
50 nm or less, more preferably 400 to 500 nm
A dye having a maximum absorption for light in the region is preferable. Furthermore, it is of course possible to use two or more types of dyes in combination.
以下、具体的にアルカリ不溶性の吸光剤の例示をすると
次の通りである。Hereinafter, specific examples of alkali-insoluble light absorbers are as follows.
モノアゾ系色素 アントラキノン系色素 ＯＮ Ｉｔ ＣＯＣＩ＋ ３ ０ＣＩ。Monoazo dye anthraquinone pigment ON It COCI+ 3 0CI.
スチリル系色素 キノフタロン系色素 等を挙げることができる。styryl pigment Quinophthalone dye etc. can be mentioned.
本発明において、吸光剤がアルカリ可溶性である場合に
併用するアルカリ不溶性化合物とは、化合物中にアルカ
リ可溶性の基をもたないものであり、前述のアルカリ不
溶性の吸光剤ももちろん含まれるが、アルカリ不溶性で
あれば、吸光剤である必要はなく、例えば、エポキシ樹
脂等を挙げることができる。In the present invention, the alkali-insoluble compound used in combination when the light-absorbing agent is alkali-soluble is one that does not have an alkali-soluble group in the compound, and of course includes the alkali-insoluble light-absorbing agent described above. It does not need to be a light absorbing agent as long as it is insoluble, and examples include epoxy resins.
また、本発明において、吸光剤がアルカリ不溶性である
場合に併用するアルカリ可溶性化合物とは、化合物中に
ＯＨ基等のアルカリ可溶性基をもっているものであり、
前述のアルカリ可溶性の吸光剤ももちろん含まれるが、
その他アルカリ可溶性であれば、吸光剤である必要はな
く、例えば、低分子量クレゾールノボラック（モノマー
も含む）、トリヒドロキシベンゾフェノン等のポリヒド
ロキシベンゾフェノン類、α−ナフトール、β−ナフト
ール、１．５ジヒドロキシナフタリン、メチルヒドロキ
シナフタリン等のヒドロキシナフタリン系化合物を挙げ
ることができる。In addition, in the present invention, the alkali-soluble compound used in combination when the light absorbing agent is alkali-insoluble is one having an alkali-soluble group such as an OH group in the compound,
Of course, the alkali-soluble light absorbing agent mentioned above is also included, but
Other light-absorbing agents do not need to be as long as they are alkali-soluble, such as low molecular weight cresol novolak (including monomers), polyhydroxybenzophenones such as trihydroxybenzophenone, α-naphthol, β-naphthol, and 1.5 dihydroxynaphthalene. , hydroxynaphthalene-based compounds such as methylhydroxynaphthalene.
本発明において用いるアルカリ可溶性の化合物又は吸光
剤の量（Ｓ）は、フォトレジスト組成物に対して０．１
〜２０％、更に好ましくは０．３〜１０％である。この
量が少ないとハレーション防止効果が少ないかあるいは
感度が悪く、また多いと残膜率が低下し解像度が悪化す
る傾向を示す。The amount (S) of the alkali-soluble compound or light absorber used in the present invention is 0.1 with respect to the photoresist composition.
-20%, more preferably 0.3-10%. When this amount is small, the antihalation effect is low or the sensitivity is poor, and when it is large, the remaining film rate tends to decrease and the resolution tends to deteriorate.
また、アルカリ不溶性の化合物又は吸光剤の量（Ｉ）は
、フォトレジスト組成物に対して０．０１〜１０％が好
ましく、０．０５〜５％がさらに好ましい。Further, the amount (I) of the alkali-insoluble compound or light absorbing agent is preferably 0.01 to 10%, more preferably 0.05 to 5%, based on the photoresist composition.
この量が少ないとハレーション防止効果が少なく、また
多いと感度が非常に悪くスカム、膜残り （スカム）が
発生する場合がある。If the amount is small, the halation prevention effect will be low, and if it is too large, the sensitivity will be very poor and scum or film residue may occur.
本発明において、特にＳと■の比率Ｓ／Ｉは、感度とハ
レーション防止能のバランスの点より、０．１より大き
いことが好ましく、通常０．５＜Ｓ／Ｉく１０であるこ
とがさらに好ましい。In the present invention, in particular, the ratio S/I between S and ■ is preferably larger than 0.1 from the viewpoint of balance between sensitivity and antihalation ability, and more preferably 0.5<S/I and 10. preferable.
〈発明の効果〉
本発明によれば、感度低下、スカム発生あるいは解像度
低下、残膜率低下といった従来の技術のもつ問題点を一
挙に解決できる。<Effects of the Invention> According to the present invention, problems of conventional techniques such as decreased sensitivity, generation of scum or resolution, and decreased film remaining rate can be solved all at once.
〈実施例〉
以下、本発明を実施例により具体的に説明するが、これ
によって本発明が制限されるものではない。<Examples> Hereinafter, the present invention will be specifically explained using Examples, but the present invention is not limited thereto.
実施例１
メタクレゾールノボラック樹脂であって、そのＧＰＣパ
ターン面積比が、分子量１５０以上５００未満（メタク
レゾールモノマーは含まない）の範囲が１８．２％、分
子量５００以上５．０００未満の範囲が２０．８％、分
子ｆｉ ５．０００を超える範囲が６１．０％であるノ
ボラック樹脂１７部、ナフトキノン−（１，２）−ジア
ジド−（２）−５−スルホン酸クロリドと２．３．４−
トリヒドロキシベンゾフェノンの縮合反応物７５部、ア
ルカリ可溶性吸光剤とし°て、式で示される化合物０．
６５部、およびアルカリ不溶性吸光剤である式
で示される化合物０．１０部をエチルセロソルブアセテ
ート ４９．２５部に溶解し、 ０．２μｍのフィルタ
ーで濾過し、フォトレジスト組成物を調製した。この組
成物をスピンコータを用いてアルミニウムを１μｍの厚
みで蒸着したシリコンウェハー上に塗布後、ホットプレ
ートで１００℃で１分間ベークした。ベーク後の膜厚は
１．２８μｍであった。ついでこのウェハーを３５０Ｗ
の高圧水銀灯を光源とする縮小投影露光装置を用いて、
ショット毎に露光時間を段階的に変えて露光した。つい
で、現像液５ＯＰＤ（住友化学工業■製商品名）を用い
現像した。リンス、乾燥後各ショットの膜減り量と露光
時間をプロットして、感度を求めた。また、未露光部の
残膜厚から残膜率を求めた。感度は、２９０ｍ５ｅｃ。Example 1 Metacresol novolac resin whose GPC pattern area ratio is 18.2% in the range of molecular weight 150 or more and less than 500 (not including metacresol monomer) and 20% in the range of molecular weight 500 or more and less than 5.000. .8%, 17 parts of novolak resin with a molecular fi of 61.0% over 5.000, naphthoquinone-(1,2)-diazide-(2)-5-sulfonic acid chloride and 2.3.4-
75 parts of a condensation reaction product of trihydroxybenzophenone, 0.0 parts of a compound represented by the formula as an alkali-soluble light absorber.
A photoresist composition was prepared by dissolving 65 parts of ethyl cellosolve acetate and 0.10 parts of an alkali-insoluble light absorbing compound represented by the formula in 49.25 parts of ethyl cellosolve acetate and filtering through a 0.2 μm filter. This composition was applied using a spin coater onto a silicon wafer on which aluminum had been deposited to a thickness of 1 μm, and then baked on a hot plate at 100° C. for 1 minute. The film thickness after baking was 1.28 μm. Next, power this wafer to 350W.
Using a reduction projection exposure device with a high-pressure mercury lamp as the light source,
Exposure was performed by changing the exposure time step by step for each shot. Then, development was performed using developer 5OPD (trade name, manufactured by Sumitomo Chemical Co., Ltd.). After rinsing and drying, the amount of film loss and exposure time for each shot was plotted to determine the sensitivity. Further, the remaining film rate was determined from the remaining film thickness of the unexposed area. Sensitivity is 290m5ec.
残膜率は９５．５％と高感度であった。また、形成され
たパターンは、下地のアルミニウムからの反射の影響を
受けずパターンのゆがみやノツチングがなく良好なハレ
ーション防止能を示した。The residual film rate was 95.5%, indicating high sensitivity. Furthermore, the formed pattern was not affected by reflection from the underlying aluminum and exhibited good antihalation ability without pattern distortion or notching.
比較例１
実施例１において、アルカリ可溶性の吸光剤を用いず、
アルカリ不溶性の吸光剤０．６５部のみを用いた以外は
、実施例１と全く同様にして組成物を調製した。ハレー
ション防止能は示したものの、感度は１．５００ｍ５ｅ
ｃ以上と大巾に低下した。またパターン間に膜残りを生
じた。Comparative Example 1 In Example 1, no alkali-soluble light absorbing agent was used,
A composition was prepared in exactly the same manner as in Example 1, except that only 0.65 parts of an alkali-insoluble light absorber was used. Although anti-halation ability was shown, the sensitivity was 1.500 m5e
It dropped significantly to more than c. Further, film remained between patterns.
比較例２
実施例１において、アルカリ不溶性吸光剤を用いず、ア
ルカリ可溶性吸光剤のみを３部用いた以外は実施例１と
全く同様にして組成物を調製したＱハレーション防止能
は示したものの、残膜率が９０％と低下し、また解像度
も実施例と比較して著しく悪化した。Comparative Example 2 A composition was prepared in exactly the same manner as in Example 1 except that the alkali-insoluble light absorber was not used and only 3 parts of the alkali-soluble light absorber was used. Q Although the composition showed antihalation ability, The residual film rate decreased to 90%, and the resolution also deteriorated significantly compared to the example.
実施例２〜３
ノボラック樹脂と少なくとも１個のＯ−キノンジアジド
を含むポジ型フォトレジスト、ＰＦ−６２００（住人化
学工業■製、固形分２７ｗｔ％）に、下記表に示す吸光
剤及び化合物を添加し、フォトレジスト組成物を調製し
た。Examples 2 to 3 A light absorbing agent and a compound shown in the table below were added to a positive photoresist, PF-6200 (manufactured by Sumima Kagaku Kogyo ■, solid content 27 wt%) containing a novolac resin and at least one O-quinone diazide. , a photoresist composition was prepared.
このポジ型フォトレジスト組成物を用いて、実施例１と
同様にアルミニウムを蒸着したウェハー上にパターンを
形成した。これは、実施例１と同様に、高感度、高残膜
率であり、ハレーション防止能も良好であった。Using this positive photoresist composition, a pattern was formed on a wafer on which aluminum had been deposited in the same manner as in Example 1. Similar to Example 1, this had high sensitivity, high residual film rate, and good antihalation ability.
Claims (1)
いて、該吸光剤がアルカリ可溶性である場合にはさらに
１種または２種以上のアルカリ不溶性の化合物を含有し
、該吸光剤がアルカリ不溶性である場合には、さらに１
種または２種以上のアルカリ可溶性の化合物を含有して
なることを特徴とするフォトレジスト組成物。In a positive photoresist composition containing a light absorbing agent, when the light absorbing agent is alkali soluble, it further contains one or more alkali insoluble compounds, and the light absorbing agent is alkali insoluble. In addition, 1
1. A photoresist composition comprising one or more alkali-soluble compounds.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62159177A JP2534872B2 (en) | 1987-06-25 | 1987-06-25 | Photoresist composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62159177A JP2534872B2 (en) | 1987-06-25 | 1987-06-25 | Photoresist composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH012034A true JPH012034A (en) | 1989-01-06 |
| JPS642034A JPS642034A (en) | 1989-01-06 |
| JP2534872B2 JP2534872B2 (en) | 1996-09-18 |
Family
ID=15687982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62159177A Expired - Fee Related JP2534872B2 (en) | 1987-06-25 | 1987-06-25 | Photoresist composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2534872B2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2640137B2 (en) * | 1989-02-28 | 1997-08-13 | 富士写真フイルム株式会社 | Positive photoresist composition |
| JP2751572B2 (en) * | 1990-06-05 | 1998-05-18 | ジェイエスアール株式会社 | Radiation-sensitive resin composition |
| JP2007107622A (en) | 2005-10-14 | 2007-04-26 | Matsushita Electric Ind Co Ltd | Dynamic pressure bearing device and spindle motor using it |
| KR20090128379A (en) * | 2007-03-05 | 2009-12-15 | 후지필름 가부시키가이샤 | Compound for photoresist, photoresist solution, and etching method using the photoresist solution |
| JP5576024B2 (en) * | 2008-02-28 | 2014-08-20 | 富士フイルム株式会社 | Photoresist liquid and etching method using the same |
| JP2010256863A (en) * | 2009-03-30 | 2010-11-11 | Fujifilm Corp | Photoresist material, photoresist film, etching method using same, and novel azo dye compound |
| CN103289679B (en) * | 2013-06-04 | 2014-12-10 | 安徽大学 | Aniline derivative/silver nano composite two-photon absorption material with living cell development function and preparation method thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6088942A (en) * | 1983-10-21 | 1985-05-18 | Fuji Photo Film Co Ltd | Photosensitive composition |
| JPS6088941A (en) * | 1983-10-21 | 1985-05-18 | Nagase Kasei Kogyo Kk | Photoresist composition |
| JP2614847B2 (en) * | 1986-06-16 | 1997-05-28 | 東京応化工業 株式会社 | Positive photosensitive composition |
| JPS63136040A (en) * | 1986-11-28 | 1988-06-08 | Tokyo Ohka Kogyo Co Ltd | Positive type photosensitive composition |
-
1987
- 1987-06-25 JP JP62159177A patent/JP2534872B2/en not_active Expired - Fee Related
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