JPH04107561A - Resist composition - Google Patents
Resist compositionInfo
- Publication number
- JPH04107561A JPH04107561A JP22518490A JP22518490A JPH04107561A JP H04107561 A JPH04107561 A JP H04107561A JP 22518490 A JP22518490 A JP 22518490A JP 22518490 A JP22518490 A JP 22518490A JP H04107561 A JPH04107561 A JP H04107561A
- Authority
- JP
- Japan
- Prior art keywords
- resist
- acid
- formula
- layer
- weight
- 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
- 239000000203 mixture Substances 0.000 title claims description 18
- 239000002253 acid Substances 0.000 claims abstract description 23
- 229920001558 organosilicon polymer Polymers 0.000 claims abstract description 23
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 18
- 238000004132 cross linking Methods 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 15
- 239000001301 oxygen Substances 0.000 abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 abstract description 15
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052710 silicon Inorganic materials 0.000 abstract description 2
- 239000010703 silicon Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 43
- 229920000642 polymer Polymers 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000001312 dry etching Methods 0.000 description 11
- 238000010894 electron beam technology Methods 0.000 description 11
- 239000000758 substrate Substances 0.000 description 10
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- -1 chloromethylphenylphenylsiloxane Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 230000007423 decrease Effects 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 229920002120 photoresistant polymer Polymers 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- FYTPGBJPTDQJCG-UHFFFAOYSA-N Trichloro(chloromethyl)silane Chemical compound ClC[Si](Cl)(Cl)Cl FYTPGBJPTDQJCG-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical class C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- SPBPCHPKSOFZQF-UHFFFAOYSA-M diphenyliodanium;hydrogen carbonate Chemical compound OC([O-])=O.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SPBPCHPKSOFZQF-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005490 tosylate group Chemical class 0.000 description 1
- FLPXNJHYVOVLSD-UHFFFAOYSA-N trichloro(2-chloroethyl)silane Chemical compound ClCC[Si](Cl)(Cl)Cl FLPXNJHYVOVLSD-UHFFFAOYSA-N 0.000 description 1
- ABADVTXFGWCNBV-UHFFFAOYSA-N trichloro-(4-chlorophenyl)silane Chemical compound ClC1=CC=C([Si](Cl)(Cl)Cl)C=C1 ABADVTXFGWCNBV-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Abstract
Description
【発明の詳細な説明】
〔概 要〕
レジストの成分として有用な有機ケイ素重合体を含むレ
ジスト組成物に関し、
２層構造レジストプロセスの上層レジストとし使用した
時に、十分な酸素プラズマ耐性を有しており、また、感
度および解像性に優れたネガ型レジストを提供すること
を目的とし、
（式中、Ｒ１は同一または異なっていてもよく、（ＣＨ
ｚ）ＩＣＯＯＨＣ１は１〜１０の整数〕、または−（Ｃ
Ｈｚ）ｓハ■−ｃＯＯＨ（ｍはＯ〜１０の整数〕を表す
）で示される繰返し単位を基本構造し、かつ式 −５ｉ
（Ｒす、 （２）（式中、ＲＺは
同一または異なっていてもよく、アルキル基またはアリ
ール基を表す）で示される末端基を有し、重量平均分子
量が１．０００〜ｓ、 ｏｏｏ、 ｏｏ。[Detailed Description of the Invention] [Summary] A resist composition containing an organosilicon polymer useful as a component of a resist, which has sufficient oxygen plasma resistance when used as an upper layer resist in a two-layer resist process. In addition, the purpose is to provide a negative resist with excellent sensitivity and resolution, (wherein R1 may be the same or different, (CH
z) ICOOHC1 is an integer from 1 to 10], or -(C
The basic structure is a repeating unit represented by -cOOH (m is an integer from O to 10), and has the formula -5i
(RS, (2) (wherein RZ may be the same or different and represents an alkyl group or an aryl group), and has a weight average molecular weight of 1.000 to s, ooo, oo.
である有機ケイ素重合体と、
酸によって活性化され、前記有機ケイ素重合体と架橋反
応をする架橋剤と、
高エネルギー線の照射により酸を発生し、架橋剤を求電
子性として、架橋反応を促進する酸発生剤と、
有機溶剤とを含むようにレジスト組成物を構成する。an organosilicon polymer which is activated by an acid and undergoes a crosslinking reaction with the organosilicon polymer; an acid is generated by irradiation with high energy rays, the crosslinking agent is made electrophilic, and the crosslinking reaction is carried out. A resist composition is configured to include an accelerating acid generator and an organic solvent.
本発明は、レジスト組成物に関する。さらに詳しく述べ
ると、本発明は、半導体装置のパターン形成に有用な、
そして特に２層構造レジストプロセスにおいて上層レジ
ストとして有用なネガ型レジスト組成物に関する。本発
明のレジスト組成物は、ＬＳＩ 、 ＶＬＳＩなどの半
導体装置の製造に有利に利用することができる。本発明
によって、このようなレジスト組成物を使用したレジス
トパターンを形成することができる。The present invention relates to a resist composition. More specifically, the present invention provides the following features:
In particular, the present invention relates to a negative resist composition useful as an upper layer resist in a two-layer resist process. The resist composition of the present invention can be advantageously used in manufacturing semiconductor devices such as LSI and VLSI. According to the present invention, a resist pattern using such a resist composition can be formed.
半導体集積回路の微細化に伴い、それらのパターンを形
成する際に不可欠なレジスト材料にも高解像性が要求さ
れている。従来のネガ型レジストとしては、たとえば、
電子線描画用としてポリクロロメチルスチレン系レジス
トが知られている。With the miniaturization of semiconductor integrated circuits, high resolution is also required for resist materials essential for forming these patterns. For example, conventional negative resists include:
Polychloromethylstyrene resists are known for use in electron beam writing.
このレジストでは、素子の高密度化に伴う基板表面の段
差の影響などで、所望の微細パターンを形成することは
困難である。そこで、段差基板上でも微細パターンを形
成する方法として２層構造リソグラフィが提案されてい
る。この方法はまず段差を有する基板上に、その段差を
平坦化するために厚膜（１〜５＃Ｉｌ）の有機層（平坦
化層）を形成する。その上にパターン描画用のレジスト
層を薄＜（０，１〜ｉｎ）形成する。パターン露光を行
い、現像してパターン描画用上層レジスト層をパターニ
ングし、次にこれをマスクパターンとして平坦化層を酸
素プラズマにより異方性エツチングを行い、基板加工用
のパターンを形成するものである。With this resist, it is difficult to form a desired fine pattern due to the influence of steps on the substrate surface due to higher density of elements. Therefore, two-layer structure lithography has been proposed as a method for forming fine patterns even on stepped substrates. In this method, first, a thick (1 to 5 #Il) organic layer (flattening layer) is formed on a substrate having a step to flatten the step. A resist layer for pattern drawing is formed thereon to a thickness of <(0,1 to 1 inch). The upper resist layer for pattern drawing is patterned by pattern exposure and development, and then, using this as a mask pattern, the flattening layer is anisotropically etched with oxygen plasma to form a pattern for substrate processing. .
この方法は、露光により直接パターン形成するレジスト
層の厚さを単層レジスト法に比べて格段に薄くできるた
め、高解像性が実現できる方法である。この方法に適用
しうるレジスト材料は、上記の説明から明らかなように
酸素プラズマに対する十分な耐性が要求され、シリコー
ン系の樹脂が検討されている０例示すれば、ポリーＰ−
クロロメチルフェニルフェニルシロキサン、ポリアリル
シルセスキオキサン、ポリビニルシルセスキオキサン等
である。This method can achieve high resolution because the thickness of the resist layer that is directly patterned by exposure can be made much thinner than in the single-layer resist method. As is clear from the above explanation, resist materials that can be applied to this method are required to have sufficient resistance to oxygen plasma, and silicone-based resins are being considered.
These include chloromethylphenylphenylsiloxane, polyallylsilsesquioxane, polyvinylsilsesquioxane, and the like.
しかしながら、このパターン形成方法に適用可能な上記
シリコーンレジストは電子線等による露光の潜像を有機
溶媒により現像せざるを得ないため、レジスト層が激し
く膨潤してしまい、２層構造リソグラフィの利点を十分
いかすことができず、解像性はさほど向上しない。その
ため、サブミクロンパターンが要求される超ＬＳＩの製
造に必要なレジストパターンを安定して形成することは
できないという欠点を有している。そのため、現像時に
膨潤による解像性の低下を生じないネガ型のパターン形
成材料が望まれていた。However, the silicone resist applicable to this pattern forming method has no choice but to develop the latent image exposed with an electron beam or the like using an organic solvent, resulting in severe swelling of the resist layer, which eliminates the advantages of two-layer structure lithography. It cannot be fully utilized, and the resolution does not improve much. Therefore, it has the disadvantage that it is not possible to stably form a resist pattern necessary for manufacturing VLSIs that require submicron patterns. Therefore, there has been a desire for a negative pattern forming material that does not cause a decrease in resolution due to swelling during development.
上記課題は、
（式中４ＲＩ は同一または異なっていてもよく、（Ｃ
Ｈｚ）ＩＣＯＯＨ［ｆは１〜１０の整数］、または（Ｃ
Ｈｚ）ｓ＋ｃＯＯＨ（ｍはＯ〜１０の整数〕を表す）で
示される繰返し単位を基本構造し、かつ式−５ｉ（Ｒ”
）＋ （２）
（式中、Ｒ２は同一または異なっていてもよく、アルキ
ル基またはアリール基を表す）で示される末端基を有し
、重量平均分子量が１ 、０００〜５，０００，０００
である有機ケイ素重合体と、
酸によって活性化され、前記有機ケイ素重合体と架橋反
応をする架橋剤と、
高エネルギー線の照射により酸を発生し、架橋剤を求電
子性として、架橋反応を促進する酸発生剤と、
有機溶剤とを含むレジスト組成物によって解決すること
ができる。The above problem is solved by
Hz) ICOOH [f is an integer from 1 to 10], or (C
The basic structure is a repeating unit represented by
) + (2) (wherein R2 may be the same or different and represents an alkyl group or an aryl group), and has a weight average molecular weight of 1,000 to 5,000,000
an organosilicon polymer which is activated by an acid and undergoes a crosslinking reaction with the organosilicon polymer; an acid is generated by irradiation with high energy rays, the crosslinking agent is made electrophilic, and the crosslinking reaction is carried out. This problem can be solved by using a resist composition containing an accelerating acid generator and an organic solvent.
本発明の有機ケイ素重合体は、式（１）のＲＩにおいて
、ｌおよびｍが１０を超えると、重合体のＳｉ含量が低
下して、酸素プラズマ耐性が劣化するので、上限は５で
あることが好ましく、３がさらに好ましい。また末端の
シリル基式（２）に含まれるＲ２はＣＬ 、 ＣｚＨｓ
またはｐｈ基が便宜である。In the organosilicon polymer of the present invention, in the RI of formula (1), if l and m exceed 10, the Si content of the polymer decreases and the oxygen plasma resistance deteriorates, so the upper limit is 5. is preferable, and 3 is more preferable. Furthermore, R2 included in the terminal silyl group formula (2) is CL, CzHs
Or a ph group is convenient.
この重合体の重量平均分子量が１．０００未満ではレジ
ストとしての被膜特性が低下するとともに耐熱性も低下
し、５，０００，０００を超えると溶剤に溶解。When the weight average molecular weight of this polymer is less than 1.000, the film properties as a resist and heat resistance are also lowered, and when it exceeds 5,000,000, it dissolves in a solvent.
することが困難になり、レジストの粘度も上昇して、均
一な被膜の形成が困難となる。The viscosity of the resist also increases, making it difficult to form a uniform film.
本発明の有機ケイ素重合体をレジスト組成物として用い
る際は、重合体を必要に応じて精製し、分子量分別を施
して用いることが好ましい。When using the organosilicon polymer of the present invention as a resist composition, it is preferable to refine the polymer as necessary and subject it to molecular weight fractionation before use.
この有機ケイ素重合体はそのままではアルカリ水溶液に
可溶であるが、適当な架橋剤との反応によって、架橋反
応生成物を生じ水溶液に溶けにくくなる。本研究の目的
にあった架橋剤は、酸発生剤の存在下で高エネルギー線
を照射した際に活性となり、有機ケイ素重合体と反応し
て架橋生成物を生じるものであればいずれであってもか
まわない。このような架橋剤としてはメラミン誘導体が
好ましく、特に窒素原子上の６個の水素原子が全て０Ｒ
（Ｒはアルキル基またはアリール基）で置き変わったも
の、もしくは−（ＣＨｚ）ｋＯＲ（Ｒは前記定義に同じ
であり、また、ｋは１−１０の整数を表す）で置き変わ
ったものが好ましい。また、このような架橋剤としては
、２．６−シヒドロキシメチルーＰ−クレゾール等のフ
ェノール誘導体もまた好ましく、特に置換基としてアル
コキシ基、フェノキシ基を有するものが適している。This organosilicon polymer is soluble in an aqueous alkaline solution as it is, but when reacted with an appropriate crosslinking agent, a crosslinking reaction product is produced, making it difficult to dissolve in an aqueous solution. The crosslinking agent suitable for the purpose of this study is any one that becomes active when irradiated with high-energy radiation in the presence of an acid generator and reacts with the organosilicon polymer to produce a crosslinked product. I don't mind. As such a crosslinking agent, a melamine derivative is preferable, and in particular, all six hydrogen atoms on the nitrogen atom are 0R.
(R is an alkyl group or an aryl group), or -(CHz)kOR (R is the same as the above definition, and k represents an integer from 1 to 10) is preferable. . As such a crosslinking agent, phenol derivatives such as 2,6-cyhydroxymethyl-P-cresol are also preferred, and those having an alkoxy group or phenoxy group as a substituent are particularly suitable.
酸発生剤として有効な化合物は、例示すると、ＰｈｚＩ
”５ｂＦｉ−、ＰｈｚＳ”５ｂＦ６−等のヘキサフルオ
ロアンチモンイオンを含むオニウム塩、（Ｐｈ 、 Ｉ
つ！ＧＯ！”−＋（Ｐｈ３５つ、ｃｏ、”−等の炭酸イ
オンを含むオニウム塩、Ｐｈ５Ｓ″ＨＣＯｊ−、Ｐｈ５
Ｓ″ＨＣＯ，−等の炭酸水素イオンを含むオニウム塩、
クロロメチル基を有するトリアジン化合物、オルトニト
ロベンジルアルコールスルホン酸エステル等のトシレー
ト系の化合物があげられる。高エネルギー線を照射する
ことにより、これらの酸発生剤が酸を発生して架橋剤が
求電子性となり、前記有機ケイ素重合体と架橋反応生成
物を生じ、アルカリ水溶液に不溶となるため、本組成物
はネガ型のレジストとなる。Examples of compounds effective as acid generators include PhzI
Onium salts containing hexafluoroantimony ions such as “5bFi-, PhzS”5bF6-, (Ph, I
One! GO! Onium salt containing carbonate ions such as ``-+ (Ph35, co, ``-, Ph5S''HCOj-, Ph5
Onium salts containing hydrogen carbonate ions such as S″HCO,-,
Examples include tosylate compounds such as triazine compounds having a chloromethyl group and orthonitrobenzyl alcohol sulfonic acid esters. When irradiated with high-energy rays, these acid generators generate acids and the crosslinking agent becomes electrophilic, producing a crosslinking reaction product with the organosilicon polymer and becoming insoluble in aqueous alkaline solutions. The composition becomes a negative resist.
前記高エネルギー線は可視光、紫外光、Ｘ１ａ等の電磁
波、電子線、イオン線等の粒子線を意味する。The high-energy rays include visible light, ultraviolet light, electromagnetic waves such as X1a, and particle beams such as electron beams and ion beams.
また、本発明のレジスト組成物を可視光、紫外光で露光
する際には、必要に応して増感剤を添加してもよい。Furthermore, when exposing the resist composition of the present invention to visible light or ultraviolet light, a sensitizer may be added as necessary.
有機ケイ素重合体、架橋剤、酸発生剤、有機溶剤の混合
比は各々の組合せによって異なり、またレジストとして
使用する際に必要な膜厚値によって異なってくるが、有
機溶剤１００重量部に対して、有機ケイ素重合体が４〜
２０ｆｉ’ｆ部、架橋剤が０．５〜２０重量部、酸発生
剤０．１〜１０重量部程度であることが好ましい。The mixing ratio of organosilicon polymer, crosslinking agent, acid generator, and organic solvent varies depending on each combination, and also varies depending on the film thickness required when used as a resist. , organosilicon polymer is 4~
It is preferable that the amount of the crosslinking agent is about 20 fi'f parts, about 0.5 to 20 parts by weight of the crosslinking agent, and about 0.1 to 10 parts by weight of the acid generator.
を機溶剤１００重量部に対して、有機ケイ素重合体が、
４重量部より少ないと、２層構造の上層レジストに成膜
するとき薄くなってピンホールが発生しやすい、また２
０重量部より多いと、厚くなりすぎて解像性が低下する
。架橋剤が０．５重量部より少ないと、現像時に膜減り
を生じ、１０重量部より多いと、レジスト中のＳｉ含量
が減少して酸素プラズマ耐性が低下する。酸発生剤が０
．１重量部より少ないと、架橋反応を促進させる効果が
少なく、１０重量部より多い′と、レジスト中のＳｉ含
量を低下させるばかりでなく、揮発成分の気化にょる空
孔やクラックがレジスト膜に発生する。For 100 parts by weight of the organic solvent, the organosilicon polymer is
If it is less than 4 parts by weight, the film becomes thin and pinholes are likely to occur when depositing on the upper layer resist of a two-layer structure;
When the amount is more than 0 parts by weight, the thickness becomes too thick and the resolution decreases. If the amount of the crosslinking agent is less than 0.5 parts by weight, film thinning occurs during development, and if it is more than 10 parts by weight, the Si content in the resist decreases and oxygen plasma resistance decreases. Acid generator is 0
．． If it is less than 1 part by weight, the effect of promoting the crosslinking reaction will be small, and if it is more than 10 parts by weight, it will not only reduce the Si content in the resist, but also cause pores and cracks to form in the resist film due to the vaporization of volatile components. Occur.
本発明のレジスト組成物は、被加工基板上に基板段差を
平坦化するための有機高分子層を形成し、その上にこの
レジスト組成物を上層レジストとして塗布し、該上層レ
ジストを高エネルギー線によって所望のパターンに露光
し、アルカリ現像液で現像し、形成された上層レジスト
パターンを酸素プラズマ等のドライエツチングで下層の
有機高分子層に転写するパターン形成方法も提供する。In the resist composition of the present invention, an organic polymer layer is formed on a substrate to be processed to flatten substrate steps, this resist composition is applied thereon as an upper layer resist, and the upper layer resist is exposed to high-energy rays. The present invention also provides a pattern forming method in which the resist pattern is exposed to a desired pattern, developed with an alkaline developer, and the formed upper resist pattern is transferred to the lower organic polymer layer by dry etching using oxygen plasma or the like.
なお、ここで有機高分子層としては、東京応化製の０Ｆ
ＰＲ等、市販のフォトレジストが使用できる。Note that the organic polymer layer used here is 0F manufactured by Tokyo Ohka Co., Ltd.
Commercially available photoresists such as PR can be used.
立爪■１
（工程１）
メチルイソブチルケトン５００ｃｃ 、ピリジン４０ｃ
ｃの混合系を撹拌しながら−７０”Ｃに冷却し、クロロ
メチルトリクロロシラン１００ｇを徐々に滴下する。Tachizume ■1 (Step 1) Methyl isobutyl ketone 500cc, pyridine 40c
The mixed system of c was cooled to -70''C while stirring, and 100 g of chloromethyltrichlorosilane was gradually added dropwise.
その後純水１００ｇを徐々に滴下する。滴下後毎分０．
５°Ｃの速度で昇温し、８５℃で１０時間撹拌した。Then, 100 g of pure water was gradually added dropwise. 0 per minute after dropping.
The temperature was raised at a rate of 5°C, and the mixture was stirred at 85°C for 10 hours.
冷却後静置して水層を除き、さらに十分な水洗いを施す
。ロータリーエバポレータで溶液を濃縮した後、多量の
沈澱剤アセトニトリルを加え、重合体を析出させた。After cooling, let stand to remove the water layer, and then rinse thoroughly with water. After concentrating the solution using a rotary evaporator, a large amount of a precipitant, acetonitrile, was added to precipitate the polymer.
その後シリル化するために、この重合体をメチルイソブ
チルケトン５００ ｇに溶解し、ピリジン１００ｃｃを
加え、０℃に冷却し、撹拌しながらトリメチルクロロシ
ラン１００ｃｃを徐々に滴下した。滴下後、系を８０℃
に昇温し、約４時間撹拌した。冷却後、系に水を加え、
析出した塩を溶解させた。水層を除き、さらに３回水洗
した。反応液に多量の水を加え、シリル化した重合体を
析出させた。Thereafter, for silylation, this polymer was dissolved in 500 g of methyl isobutyl ketone, 100 cc of pyridine was added, the mixture was cooled to 0° C., and 100 cc of trimethylchlorosilane was gradually added dropwise with stirring. After dropping, the system was heated to 80℃
and stirred for about 4 hours. After cooling, add water to the system,
The precipitated salt was dissolved. The aqueous layer was removed and washed with water three more times. A large amount of water was added to the reaction solution to precipitate a silylated polymer.
精製乾燥後、３０ｇを乾燥エチルエーテルに溶解し、金
属マグネシウム２４ｇの砕片に注いだ。次に、この溶液
を細かく砕いたドライアイス２００ ｇ上に注ぎ、５規
定塩酸１００Ｉ１１を加え、カルボン酸基が付加したア
ルカリ水溶液に可溶な有機ケーイ素重合体（Ａ）３１ｇ
が得られた。この重合体はポリスチレン換算により測定
した重量平均分子量が２．０×１０４であった。After purification and drying, 30 g was dissolved in dry ethyl ether and poured onto crushed pieces of 24 g of metallic magnesium. Next, this solution was poured onto 200 g of finely crushed dry ice, 5N hydrochloric acid (100I11) was added, and 31 g of organosilicon polymer (A) soluble in an alkaline aqueous solution to which a carboxylic acid group was added was added.
was gotten. This polymer had a weight average molecular weight of 2.0 x 104 as measured in terms of polystyrene.
丘底１
合成例１の工程１において、クロロメチルトリクロロシ
ランの代りに、クロロエチルトリクロロシラン１００ｇ
を滴下したことの他は、合成例１と同様な操作を行って
、繰返し単位式（１）のＲ１が−（Ｈｚ）ｚ Ｃ００
ｔｌである有機ケイ素重合体（Ｂ）３０ｇを合成した。Hill Bottom 1 In Step 1 of Synthesis Example 1, 100 g of chloroethyltrichlorosilane was used instead of chloromethyltrichlorosilane.
The same operation as in Synthesis Example 1 was performed except that R1 of the repeating unit formula (1) was -(Hz)z C00
30 g of tl organosilicon polymer (B) was synthesized.
この重合体はポリスチレン換算により測定した重量平均
分子量が２．ｌＸ１０’であった。This polymer has a weight average molecular weight of 2. It was 1×10'.
金底■ユ
合成例１の工程１において、クロロメチルトリクロロシ
ランの代りに、ｐ−クロロフェニルトリクロロシラン１
５０ｇを滴下したことの他は、合成例１と同様な操作を
行って、繰返し単位式（１）のＲ１が−ｏ−ｃｏｏＨで
ある有機ケイ素重合体（Ｃ）３０ｇを合成した。この重
合体はポリスチレン換算により測定した重量平均分子量
が１．７ ＸＩＯ’であった。In step 1 of Synthesis Example 1, p-chlorophenyltrichlorosilane 1 was used instead of chloromethyltrichlorosilane.
The same operation as in Synthesis Example 1 was performed except that 50 g was added dropwise, to synthesize 30 g of an organosilicon polymer (C) in which R1 of the repeating unit formula (1) is -o-cooH. This polymer had a weight average molecular weight of 1.7 XIO' as measured in terms of polystyrene.
１施■土
合成例１により得られた重合体（Ａ）Ｉｇと、架橋剤の
へキサエトキシメチルメラミン０、３ ｇ ト、酸発生
剤のジフェニルヨードニウムヘキサフルオロアンチモネ
ート０．０２ｇとをメチルイソブチルケトン１５１ｄに
溶解し、孔径が０．１ ｔａｎのメンブランフィルタで
濾過してレジスト溶液とした。1. Polymer (A) Ig obtained in Soil Synthesis Example 1, 0.3 g of hexaethoxymethylmelamine as a crosslinking agent, and 0.02 g of diphenyliodonium hexafluoroantimonate as an acid generator were mixed with methyl isobutyl. It was dissolved in Ketone 151d and filtered through a membrane filter with a pore size of 0.1 tan to obtain a resist solution.
次にＳｉ基板上に２．０ｔａａの厚さになるようにノボ
ラック系レジスト商品名ＭＰ−１３００（シプレー社）
を塗布し、ハードベークして平坦化層とし、この上に上
記レジスト溶液を０．２ Ｂの厚さになるように塗布し
、８０°Ｃで２０分ベーキングした。こうして得られた
２層レジスト膜に加速電圧２０ＫＶで電子線を露光し、
テトラメチルアンモニウムヒドロキシド水溶液（２，５
％）で現像を行った。次に試料を平行平板型のドライエ
ツチング装置に入れ、酸素プラズマ（２Ｐａ 、 ０．
２２Ｗ／ｄ）で１５分間ドライエツチングを行い、上層
パターンを下層に転写した。Next, apply a novolac resist product name MP-1300 (Shipley Co., Ltd.) to a thickness of 2.0 taa on the Si substrate.
was coated and hard baked to form a flattening layer, and the above resist solution was coated on this to a thickness of 0.2 B, and baked at 80° C. for 20 minutes. The two-layer resist film thus obtained was exposed to an electron beam at an accelerating voltage of 20 KV,
Tetramethylammonium hydroxide aqueous solution (2,5
%). Next, the sample was placed in a parallel plate type dry etching device and exposed to oxygen plasma (2 Pa, 0.2 Pa).
Dry etching was performed at 22 W/d for 15 minutes to transfer the upper layer pattern to the lower layer.
この結果、０．６趨の抜きパターンを解像することがで
きた。また、パターニングの際の電子線露光量は３０ｕ
Ｃ／Ｃ４であった。As a result, a 0.6-line punching pattern could be resolved. In addition, the electron beam exposure amount during patterning was 30u.
It was C/C4.
裏厳拠１
合成例２により得られた重合体（Ｂ）Ｉｇと、ヘキサエ
トキシメチルメラミン０．３ ｇと、ジフェニルヨード
ニウムヘキサフルオロアンチモネート０．０２ｇとをメ
チルイソブチルケトン１５Ｍ１に溶解し、孔径が０．１
ｔａｎのメンブランフィルタで濾過してレジスト溶液
とした。次にＳｉ基板上に２． Ｏｔｎａの厚さになる
ようにノボラック系レジストＭＰ−１３００（シプレー
社）を塗布し、ハードベークして平坦化層とし、この上
に上記レジスト溶液を０．２ ｎの厚さになるように塗
布し、８０゛Ｃで２０分ベーキングした。こうして得ら
れた２層レジスト膜に、ＫｒＦエキシマレーザ装置（波
長２４８ｎｍ）を用いて１７０ｓＪ／ｃｊの露光量で露
光し、テトラメチルアンモニウムヒドロキシド水溶液（
２，５％）で現像を行った。Ura-Ganju 1 Polymer (B) Ig obtained in Synthesis Example 2, 0.3 g of hexaethoxymethylmelamine, and 0.02 g of diphenyliodonium hexafluoroantimonate were dissolved in 15M1 of methyl isobutyl ketone, and the pore size was 0.1
It was filtered through a tan membrane filter to obtain a resist solution. Next, 2. A novolac resist MP-1300 (Shipley Co., Ltd.) was applied to a thickness of 0.2 nm, hard-baked to form a flattened layer, and the above resist solution was applied on top of this to a thickness of 0.2 nm. Then, it was baked at 80°C for 20 minutes. The two-layer resist film thus obtained was exposed to light using a KrF excimer laser device (wavelength 248 nm) at an exposure dose of 170 sJ/cj, and a tetramethylammonium hydroxide aqueous solution (
2.5%).
次に試料を平行平板型のドライエツチング装置に入れ、
酸素プラズマ（２Ｐａ 、 ０．２２Ｗ／ｃｓｉ）で１
５分間ドライエツチングを行い、上層パターンを下層に
転写した。この結果、０．８ ｎのスペースパターンを
解像することができた。Next, the sample was placed in a parallel plate type dry etching device.
1 with oxygen plasma (2Pa, 0.22W/csi)
Dry etching was performed for 5 minutes to transfer the upper layer pattern to the lower layer. As a result, a 0.8 n space pattern could be resolved.
裏施炭主
合成例３により得られた重合体（Ｃ）Ｉｇと、架橋剤の
２．６−ビスヒドロキシメチル−Ｐ−り０．３ｇと、ジ
フェニルヨードニウムヘキサフルオロアンチモネー）
０．０２ ｇとをメチルイソブチルケトン１５＋ｄに溶
解し、孔径が０６ｌ−のメンブランフィルタで濾過して
レジスト溶液とした０次にＳｉ基板上に２．０−の厚さ
になるようにノボラック系レジストＭＰ−１３００（シ
ブレー社）を塗布し、ハードベークして平坦化層とし、
この上に上記レジスト溶液を０．２ ｔｎａの厚さにな
るように塗布し、８０°Ｃで２０分ベーキングした。こ
うして得られた２層レジスト膜に加速電圧２０ＫＶで電
子線を露光し、テトラメチルアンモニウムヒドロキシド
水溶液（２，５％）で現像を行った。次に試料を平行平
板型のドライエツチング装置に入れ、酸素プラズマ（２
Ｐａ。Polymer (C) Ig obtained in back-coating main synthesis example 3, 0.3 g of 2,6-bishydroxymethyl-P-2 as a crosslinking agent, and diphenyliodonium hexafluoroantimone)
0.02 g was dissolved in methyl isobutyl ketone 15+d and filtered through a membrane filter with a pore size of 0.6 l to prepare a resist solution. A novolak resist was placed on a 0-order Si substrate to a thickness of 2.0. Apply MP-1300 (Sibley) and hard bake to make a flattening layer.
The above resist solution was applied onto this to a thickness of 0.2 tna, and baked at 80°C for 20 minutes. The two-layer resist film thus obtained was exposed to an electron beam at an accelerating voltage of 20 KV, and developed with a tetramethylammonium hydroxide aqueous solution (2.5%). Next, the sample was placed in a parallel plate type dry etching device, and oxygen plasma (2
Pa.
０．２２Ｗ／ｃｄ）で１５分間ドライエツチングを行い
、上層パターンを下層に転写した。この結果、０．５μ
の抜きパターンを解像することができた。また、パター
ニングの際の電子線露光量は４０ｕＣ／ｃｄであった。Dry etching was performed for 15 minutes at 0.22 W/cd) to transfer the upper layer pattern to the lower layer. As a result, 0.5μ
We were able to resolve the cutout pattern. Further, the electron beam exposure amount during patterning was 40 uC/cd.
裏ｌ拠土
合成例３により得られた重合体（Ｃ）Ｉｇと、２．６−
ビスヒドロキシメチル−ｐ−クレゾール０．３ｇと、炭
酸水素化ジフェニルヨードニウム（ＰｈｚＩ“ＨＣＯｓ
−）０．０２ ｇとをメチルイソブチルケトン１５ＭＮ
に溶解し、孔径が０．１４のメンブランフィルタで濾過
してレジスト溶液とした。次にＳｉ基板上に２．０μｍ
の厚さになるようにノボラック系レジストＭＰ−１３０
０（シプレー社）を塗布し、ハードベークして平坦化層
とし、この上に上記レジスト溶液を０．２μの厚さにな
るように塗布し、８０°Ｃで２０分ベーキングした。こ
うして得られた２層レジスト膜に加速電圧２０ＫＶで電
子線を露光し、テトラメチルアンモニウムヒドロキシド
水溶液（２，５％）で現像を行った。次に試料を平行平
板型のドライエツチング装置に入れ、酸素プラズマ（２
Ｐａ。Polymer (C) Ig obtained from backing synthesis example 3 and 2.6-
0.3 g of bishydroxymethyl-p-cresol and diphenyliodonium hydrogencarbonate (PhzI"HCOs
-)0.02 g and 15MN of methyl isobutyl ketone
The resist solution was dissolved in water and filtered through a membrane filter with a pore size of 0.14 to obtain a resist solution. Next, a 2.0 μm thick film was placed on the Si substrate.
Apply novolac resist MP-130 to a thickness of
0 (Shipley Co., Ltd.) and hard baked to form a flattening layer, the above resist solution was applied thereon to a thickness of 0.2 μm and baked at 80° C. for 20 minutes. The two-layer resist film thus obtained was exposed to an electron beam at an accelerating voltage of 20 KV, and developed with a tetramethylammonium hydroxide aqueous solution (2.5%). Next, the sample was placed in a parallel plate type dry etching device, and oxygen plasma (2
Pa.
０．２２Ｗ／ｃｄ）で１５分間ドライエツチングを行い
、上層パターンを下層に転写した。この結果、０．６μ
の抜きパターンを解像することができた。また、パター
ニングの際の電子線露光量は５０μＣ／ｄであった。Dry etching was performed for 15 minutes at 0.22 W/cd) to transfer the upper layer pattern to the lower layer. As a result, 0.6μ
We were able to resolve the cutout pattern. Further, the electron beam exposure amount during patterning was 50 μC/d.
１旌１
合成例３により得られた重合体（Ｃ）Ｉｇと、２．６−
ビスヒドロキシメチル−ｐ−クレゾール０．３ｇと、オ
ルトニトロベンジルアルコールスルホン酸エステル０．
０２ ｇとをメチルイソブチルケトン１５ｍに溶解し、
孔径が０．１ｎのメンブランフィルタで濾過してレジス
ト溶液とした。次にＳｉ基板上に２．０−の厚さになる
ようにノボラック系レジスト（ＭＰ−１３００シプレ一
社）を塗布し、ハードベークして平坦化層とし、この上
に上記レジスト溶液を０．２ ｍの厚さになるように塗
布し、８０℃で２０分ベーキングした。こうして得られ
た２層レジスト膜に加速電圧２０ＫＶで電子線を露光し
、テトラメチルアンモニウムヒドロキシド水溶液（２，
５％）で現像を行った。次に試料を平行平板型のドライ
エツチング装置に入れ、酸素プラズマ（２Ｐａ。1/1 Polymer (C) Ig obtained in Synthesis Example 3 and 2.6-
0.3 g of bishydroxymethyl-p-cresol and 0.3 g of orthonitrobenzyl alcohol sulfonic acid ester.
02 g and dissolved in 15 m of methyl isobutyl ketone,
It was filtered through a membrane filter with a pore size of 0.1 nm to obtain a resist solution. Next, a novolac resist (MP-1300, manufactured by Shipley Co., Ltd.) is applied to a thickness of 2.0 mm on the Si substrate, hard baked to form a flattened layer, and the above resist solution is applied on top of this to a thickness of 2.0 mm. It was coated to a thickness of 2 m and baked at 80°C for 20 minutes. The two-layer resist film thus obtained was exposed to an electron beam at an accelerating voltage of 20 KV, and a tetramethylammonium hydroxide aqueous solution (2,
5%). Next, the sample was placed in a parallel plate type dry etching device, and oxygen plasma (2 Pa) was applied.
０．２２Ｗ／ｄ）で１５分間ドライエツチングを行い、
上層パターンを下層に転写した。この結果、０．６μの
抜きパターンを解像することができた。また、バターニ
ングの際の電子線露光量は４５μＣ／ｃｔｊであった。Dry etching was performed for 15 minutes at 0.22 W/d).
The upper layer pattern was transferred to the lower layer. As a result, a punched pattern of 0.6μ could be resolved. Further, the electron beam exposure amount during patterning was 45 μC/ctj.
本発明のレジスト組成物において、ケイ素含有量の高い
有機ケイ素重合体を用いているため酸素プラズマ耐性に
優れ、酸発生剤より生しる酸が架橋反応の触媒として進
行するために感度が高く、また、現像液としてアルカリ
水溶液を用いていることと、有機ケイ素重合体の耐熱性
が高いことのために解像性が優れている。したがって、
本発明により、２層レジスト上層用レジストとして不可
欠な酸素プラズマ耐性、感度、解像性の３つを同時に満
足することができる。The resist composition of the present invention uses an organosilicon polymer with a high silicon content, so it has excellent oxygen plasma resistance, and the acid generated from the acid generator acts as a catalyst for the crosslinking reaction, so it has high sensitivity. Furthermore, the resolution is excellent because an alkaline aqueous solution is used as the developer and the organosilicon polymer has high heat resistance. therefore,
According to the present invention, it is possible to simultaneously satisfy the three requirements of oxygen plasma resistance, sensitivity, and resolution, which are essential for a resist for the upper layer of a two-layer resist.
Claims (1)
ＣＨ＿２）＿ｌ−ＣＯＯＨ〔ｌは１〜１０の整数〕、ま
たは▲数式、化学式、表等があります▼〔ｍは０〜１０
の整数〕を表す）で示される繰返し単位を基本構造とし
、かつ式−Ｓｉ（Ｒ＾２）＿３（２） （式中、Ｒ＾２は同一または異なっていてもよく、アル
キル基またはアリール基を表す）で示される末端基を有
し、重量平均分子量が１，０００〜５，０００，００で
ある有機ケイ素重合体と、酸によって活性化され、前記
有機ケイ素重合体と架橋反応をする架橋剤と、高エネル
ギー線の照射により酸を発生し、架橋剤を求電子性とし
て、架橋反応を促進する酸発生剤と、有機溶剤を含むレ
ジスト組成物。 ２、前記有機ケイ素重合体４〜２０重量部と、架橋剤０
．５〜２０重量部と、酸発生剤０．１〜１０重量部と、
有機溶剤１００重量部とを含む、請求項１記載のレジス
ト組成物。[Claims] 1. Formula ▲ Numerical formula, chemical formula, table, etc. ▼ (1) (In the formula, R^1 may be the same or different, -(
CH_2)_l-COOH [l is an integer from 1 to 10], or ▲Mathematical formula, chemical formula, table, etc.▼[m is 0 to 10
The basic structure is a repeating unit represented by ) and a weight average molecular weight of 1,000 to 5,000,00, and a crosslinking agent that is activated by an acid and undergoes a crosslinking reaction with the organosilicon polymer. A resist composition comprising an organic solvent, an acid generator that generates an acid upon irradiation with high-energy rays, makes the crosslinking agent electrophilic, and promotes a crosslinking reaction. 2. 4 to 20 parts by weight of the organosilicon polymer and 0 crosslinking agent
．． 5 to 20 parts by weight, and 0.1 to 10 parts by weight of an acid generator.
2. The resist composition according to claim 1, further comprising 100 parts by weight of an organic solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22518490A JPH04107561A (en) | 1990-08-29 | 1990-08-29 | Resist composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22518490A JPH04107561A (en) | 1990-08-29 | 1990-08-29 | Resist composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04107561A true JPH04107561A (en) | 1992-04-09 |
Family
ID=16825282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22518490A Pending JPH04107561A (en) | 1990-08-29 | 1990-08-29 | Resist composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04107561A (en) |
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|---|---|---|---|---|
| WO2005036270A1 (en) * | 2003-10-07 | 2005-04-21 | Hitachi Chemical Co., Ltd. | Radiation-curing composition, method for storing same, method for forming cured film, method for forming pattern, method for using pattern, electronic component, and optical waveguide |
| WO2005036269A1 (en) * | 2003-10-07 | 2005-04-21 | Hitachi Chemical Co., Ltd. | Radiation-curing composition, method for storing same, method for forming cured film, method for forming pattern, method for using pattern, electronic component, and optical waveguide |
| JP2005154715A (en) * | 2003-11-25 | 2005-06-16 | Rohm & Haas Electronic Materials Llc | Waveguide composition and waveguide made of the same |
| JP2006091828A (en) * | 2003-10-07 | 2006-04-06 | Hitachi Chem Co Ltd | Radiation curable composition, its storing method, cured film forming method, pattern forming method, pattern usage, electronic component, and optical waveguide |
| JP2006091817A (en) * | 2003-10-07 | 2006-04-06 | Hitachi Chem Co Ltd | Radiation curable composition, its storing method, cured film forming method, pattern forming method, pattern usage, electronic component, and optical waveguide |
-
1990
- 1990-08-29 JP JP22518490A patent/JPH04107561A/en active Pending
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|---|---|---|---|---|
| US7297464B2 (en) | 2003-10-07 | 2007-11-20 | Hitachi Chemical Co., Ltd. | Radiation curable composition, storing method thereof, forming method of cured film, patterning method, use of pattern, electronic components and optical waveguide |
| WO2005036269A1 (en) * | 2003-10-07 | 2005-04-21 | Hitachi Chemical Co., Ltd. | Radiation-curing composition, method for storing same, method for forming cured film, method for forming pattern, method for using pattern, electronic component, and optical waveguide |
| JP2006091828A (en) * | 2003-10-07 | 2006-04-06 | Hitachi Chem Co Ltd | Radiation curable composition, its storing method, cured film forming method, pattern forming method, pattern usage, electronic component, and optical waveguide |
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| KR100698391B1 (en) * | 2003-10-07 | 2007-03-23 | 히다치 가세고교 가부시끼가이샤 | Radiation curable composition, storing method thereof, forming method of cured film, patterning method, use of pattern, electronic components and optical waveguide |
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| KR100853054B1 (en) * | 2003-10-07 | 2008-08-19 | 히다치 가세고교 가부시끼가이샤 | Radiation curable composition, storing method thereof, forming method of cured film, patterning method, use of pattern, electronic components and optical waveguide |
| KR100869882B1 (en) * | 2003-10-07 | 2008-11-24 | 히다치 가세고교 가부시끼가이샤 | Radiation curable composition, forming method of cured film and patterning method |
| KR100924621B1 (en) * | 2003-10-07 | 2009-11-02 | 히다치 가세고교 가부시끼가이샤 | Radiation curable composition, storing method thereof, forming method of cured film, patterning method, use of pattern, electronic components and optical waveguide |
| JP4600090B2 (en) * | 2003-10-07 | 2010-12-15 | 日立化成工業株式会社 | Radiation curable composition, storage method thereof, cured film forming method, pattern forming method, pattern using method, electronic component and optical waveguide |
| JP4604710B2 (en) * | 2003-10-07 | 2011-01-05 | 日立化成工業株式会社 | Radiation curable composition, storage method thereof, cured film forming method, pattern forming method, pattern using method, electronic component and optical waveguide |
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| JP2005154715A (en) * | 2003-11-25 | 2005-06-16 | Rohm & Haas Electronic Materials Llc | Waveguide composition and waveguide made of the same |
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