JP5487728B2 - Negative radiation sensitive composition, cured pattern forming method, and cured pattern - Google Patents
Negative radiation sensitive composition, cured pattern forming method, and cured pattern Download PDFInfo
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- JP5487728B2 JP5487728B2 JP2009129656A JP2009129656A JP5487728B2 JP 5487728 B2 JP5487728 B2 JP 5487728B2 JP 2009129656 A JP2009129656 A JP 2009129656A JP 2009129656 A JP2009129656 A JP 2009129656A JP 5487728 B2 JP5487728 B2 JP 5487728B2
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- pattern
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- sensitive composition
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- KNYWDHFOQZZIDQ-UHFFFAOYSA-N trimethoxy-(2-trimethoxysilylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1[Si](OC)(OC)OC KNYWDHFOQZZIDQ-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- FNNJGIKXHZZGCV-UHFFFAOYSA-N triphenoxy(propan-2-yl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C(C)C)OC1=CC=CC=C1 FNNJGIKXHZZGCV-UHFFFAOYSA-N 0.000 description 1
- AMUIJRKZTXWCEA-UHFFFAOYSA-N triphenoxy(propyl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CCC)OC1=CC=CC=C1 AMUIJRKZTXWCEA-UHFFFAOYSA-N 0.000 description 1
- MUCRQDBOUNQJFE-UHFFFAOYSA-N triphenoxy(triphenoxysilyl)silane Chemical compound C=1C=CC=CC=1O[Si]([Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 MUCRQDBOUNQJFE-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- QDOHRQCMIFOPEY-UHFFFAOYSA-N tripropoxy(2-tripropoxysilylethyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)CC[Si](OCCC)(OCCC)OCCC QDOHRQCMIFOPEY-UHFFFAOYSA-N 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- BZIXIRYKSIMLOB-UHFFFAOYSA-N tripropoxy(tripropoxysilylmethyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C[Si](OCCC)(OCCC)OCCC BZIXIRYKSIMLOB-UHFFFAOYSA-N 0.000 description 1
- NBAPKCYEEBMZDW-UHFFFAOYSA-N tripropoxy-(2-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC=C1[Si](OCCC)(OCCC)OCCC NBAPKCYEEBMZDW-UHFFFAOYSA-N 0.000 description 1
- YMAKWPVRMIUZBP-UHFFFAOYSA-N tripropoxy-(3-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC([Si](OCCC)(OCCC)OCCC)=C1 YMAKWPVRMIUZBP-UHFFFAOYSA-N 0.000 description 1
- FOUOZDXPXSKVEL-UHFFFAOYSA-N tripropoxy-(4-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=C([Si](OCCC)(OCCC)OCCC)C=C1 FOUOZDXPXSKVEL-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ZZEMYLNHCSTIPH-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[2-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC=C1[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C ZZEMYLNHCSTIPH-UHFFFAOYSA-N 0.000 description 1
- QJJZQRNPNLTSNS-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[tris[(2-methylpropan-2-yl)oxy]silylmethyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C QJJZQRNPNLTSNS-UHFFFAOYSA-N 0.000 description 1
- MJIHPVLPZKWFBL-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propan-2-ylsilane Chemical compound CC(C)(C)O[Si](C(C)C)(OC(C)(C)C)OC(C)(C)C MJIHPVLPZKWFBL-UHFFFAOYSA-N 0.000 description 1
- DIZPPYBTFPZSGK-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propylsilane Chemical compound CCC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C DIZPPYBTFPZSGK-UHFFFAOYSA-N 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Description
本発明は、ネガ型感放射線性組成物、硬化パターン形成方法及び硬化パターンに関する。更に詳しくは、低比誘電率な硬化パターンを形成することができるネガ型感放射線性組成物、並びに、それを用いてなる硬化パターン及びその形成方法に関する。 The present invention relates to a negative radiation sensitive composition, a method for forming a cured pattern, and a cured pattern. More specifically, the present invention relates to a negative radiation-sensitive composition capable of forming a cured pattern having a low relative dielectric constant, a cured pattern using the same, and a method for forming the same.
従来、半導体素子等における層間絶縁膜として、CVD法等の真空プロセスにより形成されたシリカ(SiO2)膜が多用されている。
そして、近年、より均一な膜厚を有する層間絶縁膜を形成することを目的として、SOG(Spin on Glass)膜と呼ばれるテトラアルコキシシランの加水分解生成物を主成分とする塗布型の絶縁膜も使用されるようになっている(例えば、特許文献1参照)。また、半導体素子等の高集積化に伴い、有機SOGと呼ばれるポリオルガノシロキサンを主成分とする低比誘電率の層間絶縁膜の開発も行なわれている(例えば、特許文献2〜4参照)。
Conventionally, a silica (SiO 2 ) film formed by a vacuum process such as a CVD method has been frequently used as an interlayer insulating film in a semiconductor element or the like.
In recent years, for the purpose of forming an interlayer insulating film having a more uniform film thickness, a coating type insulating film called SOG (Spin on Glass) film, which is mainly composed of a hydrolysis product of tetraalkoxysilane, is also available. It is used (for example, refer patent document 1). In addition, with the high integration of semiconductor elements and the like, an interlayer insulating film having a low relative dielectric constant called polyorganosiloxane called organic SOG has also been developed (see, for example, Patent Documents 2 to 4).
しかしながら、半導体素子等の更なる高集積化や多層化に伴い、より優れた導体間の電気絶縁性が要求されており、それに伴いより低比誘電率な層間絶縁膜が求められるようになっている。 However, with further higher integration and multi-layering of semiconductor elements and the like, better electrical insulation between conductors is required, and accordingly, an interlayer insulating film having a lower relative dielectric constant has been demanded. Yes.
また、層間絶縁膜の形成は、通常、パターン転写処理の繰り返しによって行われる。一般的には、まず、層間絶縁膜層の上に多くの異なるマスク材料層を形成し、その最上部に感光性樹脂組成物を塗布する。次いで、縮小投影露光、現像により所望の回路パターンを感光性樹脂組成物被膜に形成した後、順次積層されたマスク材料層にパターンが転写される。
そして、最後にマスク材料層から層間絶縁膜層にパターンが転写された後、マスク材料層が除去されて層間絶縁膜が形成される。このように、一般に行われている層間絶縁膜の加工・形成は、非常に手間がかかり、非常に効率の悪いプロセスとなっているため、改善方法が求められている。
The formation of the interlayer insulating film is usually performed by repeating the pattern transfer process. In general, first, many different mask material layers are formed on an interlayer insulating film layer, and a photosensitive resin composition is applied to the uppermost portion thereof. Next, after a desired circuit pattern is formed on the photosensitive resin composition film by reduction projection exposure and development, the pattern is transferred to the sequentially stacked mask material layers.
Finally, after the pattern is transferred from the mask material layer to the interlayer insulating film layer, the mask material layer is removed to form an interlayer insulating film. As described above, processing and formation of an interlayer insulating film that is generally performed is very time-consuming and is a very inefficient process, and thus an improvement method is required.
本発明は、前記実情に鑑みてなされたものであり、感放射線性の性質を有してパターニング可能であり、良好な解像度を有し、更に焦点深度(DOF)が広く、且つ、半導体素子等の更なる高集積化や多層化に伴い要求されている、比誘電率の低い層間絶縁膜を構成する硬化パターンの形成に好適なネガ型感放射線性組成物、それを用いた硬化パターン形成方法及びこの硬化パターン形成方法により得られた硬化パターンを提供することを目的とする。 The present invention has been made in view of the above circumstances, has radiation-sensitive properties, can be patterned, has a good resolution, has a wide depth of focus (DOF), and has a semiconductor element and the like. Negative radiation-sensitive composition suitable for forming a cured pattern constituting an interlayer insulating film having a low relative dielectric constant, which is required with further higher integration and multilayering, and a cured pattern forming method using the same And it aims at providing the hardening pattern obtained by this hardening pattern formation method.
本発明は以下の通りである。
[1](A)ポリシロキサンと、
(B)感放射線性酸発生剤と、
(C)下記一般式(1)で表される構造単位(c1)を含む重合体と、
(D)溶剤と、を含有し、
前記(A)ポリシロキサンが、下記一般式(5)で表される有機ケイ素化合物(a1)及び下記一般式(6)で表される有機ケイ素化合物(a2)を含む加水分解性シラン化合物を加水分解縮合させて得られたポリシロキサンであるネガ型感放射線性組成物。
〔一般式(5)において、R 9 は1価の有機基を示す。〕
〔一般式(6)において、R 10 は水素原子、フッ素原子、炭素数1〜5の直鎖状若しくは分岐状のアルキル基、シアノ基、シアノアルキル基又はアルキルカルボニルオキシ基を示す。R 11 は1価の有機基を示す。aは1〜3の整数を示す。〕
[2]前記(C)重合体が、更に、下記一般式(2)で表される構造単位(c2)を含む前記[1]に記載のネガ型感放射線性組成物。
[3]前記(C)重合体が、更に、下記一般式(3)で表される構造単位(c3)、及び下記一般式(4)で表される構造単位(c4)のうちの少なくとも一方を含む前記[1]又は[2]に記載のネガ型感放射線性組成物。
[4]前記(C)重合体における全構造単位の合計を100モル%とした場合に、前記構造単位(c1)の含有量が1〜95モル%である前記[1]乃至[3]のうちのいずれかに記載のネガ型感放射線性組成物。
[5]前記(B)感放射線性酸発生剤の含有量が、前記(A)ポリシロキサン100質量部に対して、1〜30質量部である前記[1]乃至[4]のうちのいずれかに記載のネガ型感放射線性組成物。
[6]前記(C)重合体の含有量が、前記(A)ポリシロキサン100質量部に対して、1〜70質量部である前記[1]乃至[5]のうちのいずれかに記載のネガ型感放射線性組成物。
[7]前記[1]乃至[6]のいずれかに記載のネガ型感放射線性組成物を基板に塗布し、塗膜を形成する工程(i)と、
前記工程(i)により得られた塗膜をベークする工程(ii)と、
前記工程(ii)により得られた膜を露光する工程(iii)と、
前記工程(iii)により得られた、露光された膜をベークする工程(iv)と、
前記工程(iv)により得られた膜を現像液で現像し、ネガ型パターンを形成する工程(v)と、
前記工程(v)により得られたネガ型パターンに、高エネルギー線照射及び加熱のうちの少なくとも一方の硬化処理を施し、硬化パターンを形成する工程(vi)と、を備えることを特徴とする硬化パターン形成方法。
[8]前記[7]に記載の硬化パターン形成方法によって得られたことを特徴とする硬化パターン。
[9]前記[1]乃至[6]のいずれかに記載のネガ型感放射線性組成物により得られることを特徴とする硬化パターン。
[10]比誘電率が1.5〜3である前記[8]又は[9]に記載の硬化パターン。
[11](II−1)前記[1]乃至[6]のいずれかに記載のネガ型感放射線性組成物を基板に塗布、露光、現像し、ネガ型ホールパターンを有するネガ型ホールパターン基板を形成工程と、
(II−2)得られたネガ型ホールパターン基板上に、前記[1]乃至[6]のいずれかに記載のネガ型感放射線性組成物を塗布、露光、現像し、前記ネガ型ホールパターン基板上に、ネガ型トレンチパターンを形成し、ネガ型デュアルダマシンパターン基板を形成する工程と、
(II−3)得られたネガ型デュアルダマシンパターン基板に、高エネルギー線照射及び加熱のうちの少なくとも一方の処理を施し、デュアルダマシン構造を有する硬化パターンを形成する工程と、を備えることを特徴とする硬化パターン形成方法。
[12]前記[11]に記載の硬化パターン形成方法によって得られることを特徴とする硬化パターン。
[13]比誘電率が1.5〜3である前記[12]に記載の硬化パターン。
The present invention is as follows.
[1] (A) polysiloxane;
(B) a radiation sensitive acid generator;
(C) a polymer containing a structural unit (c1) represented by the following general formula (1);
(D) a solvent ,
The (A) polysiloxane hydrolyzes a hydrolyzable silane compound containing an organosilicon compound (a1) represented by the following general formula (5) and an organosilicon compound (a2) represented by the following general formula (6). A negative radiation sensitive composition which is a polysiloxane obtained by decomposing and condensing .
[In General Formula (5), R 9 represents a monovalent organic group. ]
[In General Formula (6), R 10 represents a hydrogen atom, a fluorine atom, a linear or branched alkyl group having 1 to 5 carbon atoms, a cyano group, a cyanoalkyl group, or an alkylcarbonyloxy group. R 11 represents a monovalent organic group. a represents an integer of 1 to 3. ]
[2] The negative radiation-sensitive composition according to [1], wherein the polymer (C) further includes a structural unit (c2) represented by the following general formula (2).
[3] The polymer (C) further includes at least one of a structural unit (c3) represented by the following general formula (3) and a structural unit (c4) represented by the following general formula (4). The negative radiation sensitive composition as described in [1] or [2] above.
[4] In the above [1] to [3], the content of the structural unit (c1) is 1 to 95 mol% when the total of all the structural units in the polymer (C) is 100 mol%. The negative radiation sensitive composition in any one of them.
[ 5 ] The content of the (B) radiation sensitive acid generator is 1 to 30 parts by mass with respect to 100 parts by mass of the (A) polysiloxane, and any one of [1] to [ 4 ]. The negative radiation-sensitive composition according to claim 1.
[ 6 ] The content of the (C) polymer is 1 to 70 parts by mass with respect to 100 parts by mass of the (A) polysiloxane, according to any one of [1] to [ 5 ]. Negative radiation sensitive composition.
[ 7 ] A step (i) of applying a negative radiation-sensitive composition according to any one of [1] to [ 6 ] to a substrate to form a coating film;
A step (ii) of baking the coating film obtained by the step (i);
Exposing the film obtained by the step (ii) (iii);
A step (iv) of baking the exposed film obtained by the step (iii);
Developing the film obtained in the step (iv) with a developer to form a negative pattern (v);
A step (vi) of forming a cured pattern by subjecting the negative pattern obtained by the step (v) to at least one of high energy ray irradiation and heating to form a cured pattern. Pattern forming method.
[ 8 ] A cured pattern obtained by the cured pattern forming method according to [ 7 ].
[9] A cured pattern obtained by the negative radiation-sensitive composition according to any one of [1] to [ 6 ].
[ 10 ] The cured pattern according to [ 8 ] or [ 9 ], wherein the relative dielectric constant is 1.5 to 3.
[ 11 ] (II-1) A negative hole pattern substrate having a negative hole pattern obtained by coating, exposing and developing the negative radiation sensitive composition according to any one of [1] to [ 6 ] on a substrate. Forming process,
(II-2) On the obtained negative hole pattern substrate, the negative radiation sensitive composition according to any one of [1] to [ 6 ] is applied, exposed and developed, and the negative hole pattern is obtained. Forming a negative trench pattern on the substrate and forming a negative dual damascene pattern substrate;
(II-3) The obtained negative dual damascene pattern substrate is subjected to at least one of high energy ray irradiation and heating to form a cured pattern having a dual damascene structure. A cured pattern forming method.
[ 12 ] A cured pattern obtained by the method for forming a cured pattern according to [ 11 ].
[ 13 ] The cured pattern according to [ 12 ], wherein the relative dielectric constant is 1.5 to 3.
本発明のネガ型感放射線性組成物は、高解像度であり、焦点深度(DOF)にも優れているため、微細なパターニングが可能であるとともに、低比誘電率な硬化パターンを容易に形成することができる。そのため、LSI、システムLSI、DRAM、SDRAM、RDRAM、D−RDRAM等の半導体素子の微細加工用材料として用いることができるだけでなく、層間絶縁膜用材料としても優れており、特に銅ダマシンプロセスを含む半導体素子に有用である。また、本発明の硬化パターン形成方法は、低比誘電率な層間絶縁膜を必要とする加工プロセス等において好適に用いることができ、従来の層間絶縁膜を用いた加工プロセスの効率を大幅に改善することができる。 Since the negative radiation sensitive composition of the present invention has high resolution and excellent depth of focus (DOF), fine patterning is possible and a cured pattern having a low relative dielectric constant is easily formed. be able to. Therefore, it can be used not only as a material for fine processing of semiconductor elements such as LSI, system LSI, DRAM, SDRAM, RDRAM, and D-RDRAM, but also as an interlayer insulating film material, particularly including a copper damascene process. Useful for semiconductor devices. Further, the cured pattern forming method of the present invention can be suitably used in a processing process that requires an interlayer insulating film having a low relative dielectric constant, and greatly improves the efficiency of the processing process using a conventional interlayer insulating film. can do.
以下、本発明を詳細に説明する。
[1]ネガ型感放射線性組成物
本発明のネガ型感放射線性組成物は、(A)ポリシロキサン(以下、「ポリシロキサン(A)」という。)と、(B)感放射線性酸発生剤(以下、「酸発生剤(B)」ともいう。)と、(C)重合体(以下、「重合体(C)」ともいう。)と、(D)溶剤(以下、「溶剤(D)」ともいう。)と、を含有する。
Hereinafter, the present invention will be described in detail.
[1] Negative-type radiation-sensitive composition The negative-type radiation-sensitive composition of the present invention comprises (A) polysiloxane (hereinafter referred to as “polysiloxane (A)”) and (B) generation of radiation-sensitive acid. Agent (hereinafter also referred to as “acid generator (B)”), (C) polymer (hereinafter also referred to as “polymer (C)”), (D) solvent (hereinafter referred to as “solvent (D)”. ) ")).
(1−1)ポリシロキサン(A)
本発明における前記ポリシロキサン(A)は、下記一般式(5)で表される有機ケイ素化合物(以下、「化合物(a1)」ともいう。)と、下記一般式(6)で表される有機ケイ素化合物(以下、「化合物(a2)」ともいう。)と、を含む加水分解性シラン化合物を加水分解縮合させて得られたものである。
(1-1) Polysiloxane (A)
The polysiloxane (A) in the present invention is an organic silicon compound represented by the following general formula (5) (hereinafter also referred to as “compound (a1)”) and an organic represented by the following general formula (6). It is obtained by hydrolytic condensation of a hydrolyzable silane compound containing a silicon compound (hereinafter also referred to as “compound (a2)”).
(1−1−1)化合物(a1)
前記一般式(5)のR9における1価の有機基としては、アルキル基、アルケニル基、アリール基、アリル基、グリシジル基等が挙げられる。これらのなかでも、アルキル基、アリール基であることが好ましい。
前記アルキル基としては、炭素数1〜5の直鎖状若しくは分岐状のアルキル基が挙げられる。具体的には、メチル基、エチル基、プロピル基、ブチル基等が挙げられる。尚、これらのアルキル基における1又は2以上の水素原子は、フッ素原子等に置換されていてもよい。
前記アリール基としては、フェニル基、ナフチル基、メチルフェニル基、エチルフェニル基、クロロフェニル基、ブロモフェニル基、フルオロフェニル基等が挙げられる。これらのなかでも、フェニル基が好ましい。
前記アルケニル基としては、ビニル基、プロペニル基、3−ブテニル基、3−ペンテニル基、3−ヘキセニル基等が挙げられる。
尚、各R9は全て同一であってもよいし、全て又は一部が異なっていてもよい。
(1-1-1) Compound (a1)
Examples of the monovalent organic group for R 9 in the general formula (5) include an alkyl group, an alkenyl group, an aryl group, an allyl group, and a glycidyl group. Among these, an alkyl group and an aryl group are preferable.
As said alkyl group, a C1-C5 linear or branched alkyl group is mentioned. Specific examples include a methyl group, an ethyl group, a propyl group, and a butyl group. In addition, one or two or more hydrogen atoms in these alkyl groups may be substituted with a fluorine atom or the like.
Examples of the aryl group include a phenyl group, a naphthyl group, a methylphenyl group, an ethylphenyl group, a chlorophenyl group, a bromophenyl group, and a fluorophenyl group. Among these, a phenyl group is preferable.
Examples of the alkenyl group include a vinyl group, a propenyl group, a 3-butenyl group, a 3-pentenyl group, and a 3-hexenyl group.
Each R 9 may be the same or all or a part of them may be different.
前記一般式(5)で表される化合物(a1)としては、テトラメトキシシラン、テトラエトキシシラン、テトラ−n−プロポキシシラン、テトラ−イソプロポキシシラン、テトラ−n−ブトキシラン、テトラ−sec−ブトキシシラン、テトラ−tert−ブトキシシラン、テトラフェノキシシラン等が挙げられる。
これらのなかでも、テトラメトキシシラン、テトラエトキシシランが好ましい。
尚、前記一般式(5)で表される化合物(a1)は、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
Examples of the compound (a1) represented by the general formula (5) include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-isopropoxysilane, tetra-n-butoxysilane, and tetra-sec-butoxysilane. , Tetra-tert-butoxysilane, tetraphenoxysilane and the like.
Among these, tetramethoxysilane and tetraethoxysilane are preferable.
In addition, the compound (a1) represented by the said General formula (5) may be used individually by 1 type, and may be used in combination of 2 or more type.
(1−1−2)化合物(a2)
前記一般式(6)のR10における炭素数1〜5の直鎖状若しくは分岐状のアルキル基としては、メチル基、エチル基、プロピル基、ブチル基等が挙げられる。尚、これらのアルキル基における1又は2以上の水素原子は、フッ素原子等に置換されていてもよい。
また、前記R10におけるシアノアルキル基としては、シアノエチル基、シアノプロピル基等が挙げられる。
更に、前記R10におけるアルキルカルボニルオキシ基としては、メチルカルボニルオキシ基、エチルカルボニルオキシ基、プロピルカルボニルオキシ基、ブチルカルボニルオキシ基等が挙げられる。
尚、R10が複数存在する場合(即ち、前記aが2又は3である場合)、各R10は全て同一であってもよいし、全て又は一部が異なっていてもよい。
(1-1-2) Compound (a2)
Examples of the linear or branched alkyl group having 1 to 5 carbon atoms in R 10 of the general formula (6) include a methyl group, an ethyl group, a propyl group, and a butyl group. In addition, one or two or more hydrogen atoms in these alkyl groups may be substituted with a fluorine atom or the like.
Examples of the cyanoalkyl group in R 10 include a cyanoethyl group and a cyanopropyl group.
Furthermore, examples of the alkylcarbonyloxy group in R 10 include a methylcarbonyloxy group, an ethylcarbonyloxy group, a propylcarbonyloxy group, and a butylcarbonyloxy group.
In the case where R 10 there are a plurality (i.e., when the a is 2 or 3) may be all each R 10 is the same, may be different for all or part.
また、前記一般式(6)のR11における「1価の有機基」については、前記一般式(5)のR9における「1価の有機基」の説明をそのまま適用することができる。尚、前記R11が複数存在する場合(即ち、前記aが1又は2である場合)、各R11は全て同一であってもよいし、全て又は一部が異なっていてもよい。 In addition, regarding the “monovalent organic group” in R 11 of the general formula (6), the description of the “monovalent organic group” in R 9 of the general formula (5) can be applied as it is. When a plurality of R 11 are present (that is, when a is 1 or 2), all R 11 may be the same, or all or a part of them may be different.
前記一般式(6)で表される化合物(a2)の具体例としては、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリ−n−プロポキシシラン、メチルトリイソプロポキシシラン、メチルトリ−n−ブトキシシラン、メチルトリ−sec−ブトキシシラン、メチルトリ−tert−ブトキシシラン、メチルトリフェノキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、エチルトリ−n−プロポキシシラン、エチルトリイソプロポキシシラン、エチルトリ−n−ブトキシシラン、エチルトリ−sec−ブトキシシラン、エチルトリ−tert−ブトキシシラン、エチルトリフェノキシシラン、n−プロピルトリメトキシシラン、n−プロピルトリエトキシシラン、n−プロピルトリ−n−プロポキシシラン、n−プロピルトリイソプロポキシシラン、n−プロピルトリ−n−ブトキシシラン、n−プロピルトリ−sec−ブトキシシラン、n−プロピルトリ−tert−ブトキシシラン、n−プロピルトリフェノキシシラン、イソプロピルトリメトキシシラン、イソプロピルトリエトキシシラン、イソプロピルトリ−n−プロポキシシラン、イソプロピルトリイソプロポキシシラン、イソプロピルトリ−n−ブトキシシラン、イソプロピルトリ−sec−ブトキシシラン、イソプロピルトリ−tert−ブトキシシラン、イソプロピルトリフェノキシシラン、n−ブチルトリメトキシシラン、n−ブチルトリエトキシシラン、n−ブチルトリ−n−プロポキシシラン、n−ブチルトリイソプロポキシシラン、n−ブチルトリ−n−ブトキシシラン、n−ブチルトリ−sec−ブトキシシラン、n−ブチルトリ−tert−ブトキシシラン、n−ブチルトリフェノキシシラン、 Specific examples of the compound (a2) represented by the general formula (6) include methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-propoxysilane, methyltriisopropoxysilane, methyltri-n-butoxysilane, Methyltri-sec-butoxysilane, methyltri-tert-butoxysilane, methyltriphenoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, ethyltri-n-propoxysilane, ethyltriisopropoxysilane, ethyltri-n-butoxysilane, ethyltri -Sec-butoxysilane, ethyltri-tert-butoxysilane, ethyltriphenoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, n-propyltri-n-propoxysilane, -Propyltriisopropoxysilane, n-propyltri-n-butoxysilane, n-propyltri-sec-butoxysilane, n-propyltri-tert-butoxysilane, n-propyltriphenoxysilane, isopropyltrimethoxysilane, isopropyl Triethoxysilane, isopropyltri-n-propoxysilane, isopropyltriisopropoxysilane, isopropyltri-n-butoxysilane, isopropyltri-sec-butoxysilane, isopropyltri-tert-butoxysilane, isopropyltriphenoxysilane, n-butyl Trimethoxysilane, n-butyltriethoxysilane, n-butyltri-n-propoxysilane, n-butyltriisopropoxysilane, n-butyltri-n-butoxysilane, - butyltri -sec- butoxysilane, n- butyltri -tert- butoxysilane, n- butyl triphenoxy silane,
sec−ブチルトリメトキシシラン、sec−ブチルイソトリエトキシシラン、sec−ブチルトリ−n−プロポキシシラン、sec−ブチルトリイソプロポキシシラン、sec−ブチルトリ−n−ブトキシシラン、sec−ブチルトリ−sec−ブトキシシラン、sec−ブチルトリ−tert−ブトキシシラン、sec−ブチルトリフェノキシシラン、tert−ブチルトリメトキシシラン、tert−ブチルトリエトキシシラン、tert−ブチルトリ−n−プロポキシシラン、tert−ブチルトリイソプロポキシシラン、tert−ブチルトリ−n−ブトキシシラン、tert−ブチルトリ−sec−ブトキシシラン、tert−ブチルトリ−tert−ブトキシシラン、tert−ブチルトリフェノキシシラン、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジメチルジ−n−プロポキシシラン、ジメチルジイソプロポキシシラン、ジメチルジ−n−ブトキシシラン、ジメチルジ−sec−ブトキシシラン、ジメチルジ−tert−ブトキシシラン、ジメチルジフェノキシシラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、ジエチルジ−n−プロポキシシラン、ジエチルジイソプロポキシシラン、ジエチルジ−n−ブトキシシラン、ジエチルジ−sec−ブトキシシラン、ジエチルジ−tert−ブトキシシラン、ジエチルジフェノキシシラン、ジ−n−プロピルジメトキシシラン、ジ−n−プロピルジエトキシシラン、ジ−n−プロピルジ−n−プロポキシシラン、ジ−n−プロピルジイソプロポキシシラン、ジ−n−プロピルジ−n−ブトキシシラン、ジ−n−プロピルジ−sec−ブトキシシラン、ジ−n−プロピルジ−tert−ブトキシシラン、ジ−n−プロピルジ−フェノキシシラン、 sec-butyltrimethoxysilane, sec-butylisotriethoxysilane, sec-butyltri-n-propoxysilane, sec-butyltriisopropoxysilane, sec-butyltri-n-butoxysilane, sec-butyltri-sec-butoxysilane, sec-butyltri-tert-butoxysilane, sec-butyltriphenoxysilane, tert-butyltrimethoxysilane, tert-butyltriethoxysilane, tert-butyltri-n-propoxysilane, tert-butyltriisopropoxysilane, tert-butyltri -N-butoxysilane, tert-butyltri-sec-butoxysilane, tert-butyltri-tert-butoxysilane, tert-butyltriphenoxysilane, dimethyldimeth Sisilane, dimethyldiethoxysilane, dimethyldi-n-propoxysilane, dimethyldiisopropoxysilane, dimethyldi-n-butoxysilane, dimethyldi-sec-butoxysilane, dimethyldi-tert-butoxysilane, dimethyldiphenoxysilane, diethyldimethoxysilane, Diethyldiethoxysilane, diethyldi-n-propoxysilane, diethyldiisopropoxysilane, diethyldi-n-butoxysilane, diethyldi-sec-butoxysilane, diethyldi-tert-butoxysilane, diethyldiphenoxysilane, di-n-propyldimethoxy Silane, di-n-propyldiethoxysilane, di-n-propyldi-n-propoxysilane, di-n-propyldiisopropoxysilane, di-n-propyldi-n-butyl Kishishiran, di -n- propyl di -sec- butoxysilane, di -n- propyl di -tert- butoxysilane, di -n- propyl di - phenoxy silane,
ジイソプロピルジメトキシシラン、ジイソプロピルジエトキシシラン、ジイソプロピルジ−n−プロポキシシラン、ジイソプロピルジイソプロポキシシラン、ジイソプロピルジ−n−ブトキシシラン、ジイソプロピルジ−sec−ブトキシシラン、ジイソプロピルジ−tert−ブトキシシラン、ジイソプロピルジフェノキシシラン、ジ−n−ブチルジメトキシシラン、ジ−n−ブチルジエトキシシラン、ジ−n−ブチルジ−n−プロポキシシラン、ジ−n−ブチルジイソプロポキシシラン、ジ−n−ブチルジ−n−ブトキシシラン、ジ−n−ブチルジ−sec−ブトキシシラン、ジ−n−ブチルジ−tert−ブトキシシラン、ジ−n−ブチルジ−フェノキシシラン、ジ−sec−ブチルジメトキシシラン、ジ−sec−ブチルジエトキシシラン、ジ−sec−ブチルジ−n−プロポキシシラン、ジ−sec−ブチルジイソプロポキシシラン、ジ−sec−ブチルジ−n−ブトキシシラン、ジ−sec−ブチルジ−sec−ブトキシシラン、ジ−sec−ブチルジ−tert−ブトキシシラン、ジ−sec−ブチルジ−フェノキシシラン、ジ−tert−ブチルジメトキシシラン、ジ−tert−ブチルジエトキシシラン、ジ−tert−ブチルジ−n−プロポキシシラン、ジ−tert−ブチルジイソプロポキシシラン、ジ−tert−ブチルジ−n−ブトキシシラン、ジ−tert−ブチルジ−sec−ブトキシシラン、ジ−tert−ブチルジ−tert−ブトキシシラン、ジ−tert−ブチルジ−フェノキシシラン等が挙げられる。 Diisopropyldimethoxysilane, diisopropyldiethoxysilane, diisopropyldi-n-propoxysilane, diisopropyldiisopropoxysilane, diisopropyldi-n-butoxysilane, diisopropyldi-sec-butoxysilane, diisopropyldi-tert-butoxysilane, diisopropyldiphenoxy Silane, di-n-butyldimethoxysilane, di-n-butyldiethoxysilane, di-n-butyldi-n-propoxysilane, di-n-butyldiisopropoxysilane, di-n-butyldi-n-butoxysilane , Di-n-butyldi-sec-butoxysilane, di-n-butyldi-tert-butoxysilane, di-n-butyldi-phenoxysilane, di-sec-butyldimethoxysilane, di-sec-butyldiethoxy Run, Di-sec-butyldi-n-propoxysilane, di-sec-butyldiisopropoxysilane, di-sec-butyldi-n-butoxysilane, di-sec-butyldi-sec-butoxysilane, di-sec-butyldi -Tert-butoxysilane, di-sec-butyldi-phenoxysilane, di-tert-butyldimethoxysilane, di-tert-butyldiethoxysilane, di-tert-butyldi-n-propoxysilane, di-tert-butyldiiso Examples include propoxysilane, di-tert-butyldi-n-butoxysilane, di-tert-butyldi-sec-butoxysilane, di-tert-butyldi-tert-butoxysilane, and di-tert-butyldi-phenoxysilane.
これらの化合物(a2)のなかでも、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリ−n−プロポキシシラン、メチルトリ−イソプロポキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン等が好ましい。
尚、前記一般式(6)で表される化合物(a2)は、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
Among these compounds (a2), methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-propoxysilane, methyltri-isopropoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, dimethyldimethoxysilane, dimethyldiethoxy Silane, diethyldimethoxysilane, diethyldiethoxysilane and the like are preferable.
In addition, the compound (a2) represented by the general formula (6) may be used alone or in combination of two or more.
(1−1−3)他の化合物(a3)
前記ポリシロキサン(A)を得るための前記加水分解性シラン化合物は、前記化合物(a1)及び(a2)のみを含んでもいてもよいし、必要に応じて、下記一般式(7)で表わされる有機ケイ素化合物(以下、「化合物(a3)」ともいう。)を更に含んでいてもよい。
(1-1-3) Other compound (a3)
The hydrolyzable silane compound for obtaining the polysiloxane (A) may contain only the compounds (a1) and (a2), and is represented by the following general formula (7) as necessary. An organic silicon compound (hereinafter also referred to as “compound (a3)”) may be further included.
前記一般式(7)のR12及びR16における「炭素数1〜5の直鎖状若しくは分岐状のアルキル基」、「シアノアルキル基」及び「アルキルカルボニルオキシ基」については、前記一般式(6)のR10における「炭素数1〜5の直鎖状若しくは分岐状のアルキル基」、「シアノアルキル基」及び「アルキルカルボニルオキシ基」の説明をそのまま適用することができる。尚、R12及びR16は同一であってもよいし、異なっていてもよい。また、R12が複数存在する場合(即ち、前記bが2である場合)、各R12は同一であってもよいし、異なっていてもよい。更に、R16が複数存在する場合(即ち、前記dが2である場合)、各R16は同一であってもよいし、異なっていてもよい。 The “linear or branched alkyl group having 1 to 5 carbon atoms”, “cyanoalkyl group” and “alkylcarbonyloxy group” in R 12 and R 16 of the general formula (7) are the above general formula ( The description of “a linear or branched alkyl group having 1 to 5 carbon atoms”, “cyanoalkyl group” and “alkylcarbonyloxy group” in R 10 of 6) can be applied as it is. R 12 and R 16 may be the same or different. Further, when a plurality of R 12 are present (that is, when b is 2), each R 12 may be the same or different. Further, when there are a plurality of R 16 (that is, when d is 2), each R 16 may be the same or different.
前記一般式(7)のR13及びR15における「1価の有機基」については、前記一般式(5)のR9における「1価の有機基」の説明をそのまま適用することができる。尚、R13及びR15は同一であってもよいし、異なっていてもよい。また、R13が複数存在する場合(即ち、前記bが1である場合)、各R13は同一であってもよいし、異なっていてもよい。更に、R15が複数存在する場合(即ち、前記dが1である場合)、各R15は同一であってもよいし、異なっていてもよい。 With respect to the “monovalent organic group” in R 13 and R 15 of the general formula (7), the description of the “monovalent organic group” in R 9 of the general formula (5) can be applied as it is. R 13 and R 15 may be the same or different. When a plurality of R 13 are present (that is, when b is 1), each R 13 may be the same or different. Further, when a plurality of R 15 are present (that is, when d is 1), each R 15 may be the same or different.
前記一般式(7)のR13におけるアリーレン基としては、例えば、炭素数6〜10のアリーレン基が好ましい。具体的には、例えば、フェニレン基、ナフチレン基、メチルフェニレン基、エチルフェニレン基、クロロフェニレン基、ブロモフェニレン基、フルオロフェニレン基等が挙げられる。
また、R13における炭素数2〜10のアルキレン基としては、例えば、エチレン基、プロピレン基、ブチレン基等が挙げられる。
As an arylene group in R < 13 > of the said General formula (7), a C6-C10 arylene group is preferable, for example. Specific examples include a phenylene group, a naphthylene group, a methylphenylene group, an ethylphenylene group, a chlorophenylene group, a bromophenylene group, and a fluorophenylene group.
Further, the alkylene group having 2 to 10 carbon atoms in R 13, for example, ethylene, propylene, butylene, and the like.
前記一般式(7)において、c=0である場合の化合物としては、ヘキサメトキシジシラン、ヘキサエトキシジシラン、ヘキサフェノキシジシラン、1,1,1,2,2−ペンタメトキシ−2−メチルジシラン、1,1,1,2,2−ペンタエトキシ−2−メチルジシラン、1,1,1,2,2−ペンタフェノキシ−2−メチルジシラン、1,1,1,2,2−ペンタメトキシ−2−エチルジシラン、1,1,1,2,2−ペンタエトキシ−2−エチルジシラン、1,1,1,2,2−ペンタフェノキシ−2−エチルジシラン、1,1,1,2,2−ペンタメトキシ−2−フェニルジシラン、1,1,1,2,2−ペンタエトキシ−2−フェニルジシラン、1,1,1,2,2−ペンタフェノキシ−2−フェニルジシラン、1,1,2,2−テトラメトキシ−1,2−ジメチルジシラン、1,1,2,2−テトラエトキシ−1,2−ジメチルジシラン、1,1,2,2−テトラフェノキシ−1,2−ジメチルジシラン、1,1,2,2−テトラメトキシ−1,2−ジエチルジシラン、1,1,2,2−テトラエトキシ−1,2−ジエチルジシラン、1,1,2,2−テトラフェノキシ−1,2−ジエチルジシラン、1,1,2,2−テトラメトキシ−1,2−ジフェニルジシラン、1,1,2,2−テトラエトキシ−1,2−ジフェニルジシラン、1,1,2,2−テトラフェノキシ−1,2−ジフェニルジシラン、 In the general formula (7), the compound in the case where c = 0 is hexamethoxydisilane, hexaethoxydisilane, hexaphenoxydisilane, 1,1,1,2,2-pentamethoxy-2-methyldisilane, 1 , 1,1,2,2-pentaethoxy-2-methyldisilane, 1,1,1,2,2-pentaphenoxy-2-methyldisilane, 1,1,1,2,2-pentamethoxy-2- Ethyldisilane, 1,1,1,2,2-pentaethoxy-2-ethyldisilane, 1,1,1,2,2-pentaphenoxy-2-ethyldisilane, 1,1,1,2,2-penta Methoxy-2-phenyldisilane, 1,1,1,2,2-pentaethoxy-2-phenyldisilane, 1,1,1,2,2-pentaphenoxy-2-phenyldisilane, 1,1,2,2 − Tramethoxy-1,2-dimethyldisilane, 1,1,2,2-tetraethoxy-1,2-dimethyldisilane, 1,1,2,2-tetraphenoxy-1,2-dimethyldisilane, 1,1,2, , 2-tetramethoxy-1,2-diethyldisilane, 1,1,2,2-tetraethoxy-1,2-diethyldisilane, 1,1,2,2-tetraphenoxy-1,2-diethyldisilane, , 1,2,2-tetramethoxy-1,2-diphenyldisilane, 1,1,2,2-tetraethoxy-1,2-diphenyldisilane, 1,1,2,2-tetraphenoxy-1,2- Diphenyldisilane,
1,1,2−トリメトキシ−1,2,2−トリメチルジシラン、1,1,2−トリエトキシ−1,2,2−トリメチルジシラン、1,1,2−トリフェノキシ−1,2,2−トリメチルジシラン、1,1,2−トリメトキシ−1,2,2−トリエチルジシラン、1,1,2−トリエトキシ−1,2,2−トリエチルジシラン、1,1,2−トリフェノキシ−1,2,2−トリエチルジシラン、1,1,2−トリメトキシ−1,2,2−トリフェニルジシラン、1,1,2−トリエトキシ−1,2,2−トリフェニルジシラン、1,1,2−トリフェノキシ−1,2,2−トリフェニルジシラン、1,2−ジメトキシ−1,1,2,2−テトラメチルジシラン、1,2−ジエトキシ−1,1,2,2−テトラメチルジシラン、1,2−ジフェノキシ−1,1,2,2−テトラメチルジシラン、1,2−ジメトキシ−1,1,2,2−テトラエチルジシラン、1,2−ジエトキシ−1,1,2,2−テトラエチルジシラン、1,2−ジフェノキシ−1,1,2,2−テトラエチルジシラン、1,2−ジメトキシ−1,1,2,2−テトラフェニルジシラン、1,2−ジエトキシ−1,1,2,2−テトラフェニルジシラン、1,2−ジフェノキシ−1,1,2,2−テトラフェニルジシラン等を挙げることができる。 1,1,2-trimethoxy-1,2,2-trimethyldisilane, 1,1,2-triethoxy-1,2,2-trimethyldisilane, 1,1,2-triphenoxy-1,2,2-trimethyl Disilane, 1,1,2-trimethoxy-1,2,2-triethyldisilane, 1,1,2-triethoxy-1,2,2-triethyldisilane, 1,1,2-triphenoxy-1,2,2 -Triethyldisilane, 1,1,2-trimethoxy-1,2,2-triphenyldisilane, 1,1,2-triethoxy-1,2,2-triphenyldisilane, 1,1,2-triphenoxy-1 1,2-diphenyldisilane, 1,2-dimethoxy-1,1,2,2-tetramethyldisilane, 1,2-diethoxy-1,1,2,2-tetramethyldisilane, 1,2-dipheno 1,1,2,2-tetramethyldisilane, 1,2-dimethoxy-1,1,2,2-tetraethyldisilane, 1,2-diethoxy-1,1,2,2-tetraethyldisilane, 1, 2-diphenoxy-1,1,2,2-tetraethyldisilane, 1,2-dimethoxy-1,1,2,2-tetraphenyldisilane, 1,2-diethoxy-1,1,2,2-tetraphenyldisilane 1,2-diphenoxy-1,1,2,2-tetraphenyldisilane and the like.
これらの化合物(c=0である場合の化合物)のなかでも、ヘキサメトキシジシラン、ヘキサエトキシジシラン、1,1,2,2−テトラメトキシ−1,2−ジメチルジシラン、1,1,2,2−テトラエトキシ−1,2−ジメチルジシラン、1,1,2,2−テトラメトキシ−1,2−ジフェニルジシラン、1,2−ジメトキシ−1,1,2,2−テトラメチルジシラン、1,2−ジエトキシ−1,1,2,2−テトラメチルジシラン、1,2−ジメトキシ−1,1,2,2−テトラフェニルジシラン、1,2−ジエトキシ−1,1,2,2−テトラフェニルジシラン等が好ましい。 Among these compounds (compounds where c = 0), hexamethoxydisilane, hexaethoxydisilane, 1,1,2,2-tetramethoxy-1,2-dimethyldisilane, 1,1,2,2 -Tetraethoxy-1,2-dimethyldisilane, 1,1,2,2-tetramethoxy-1,2-diphenyldisilane, 1,2-dimethoxy-1,1,2,2-tetramethyldisilane, 1,2, -Diethoxy-1,1,2,2-tetramethyldisilane, 1,2-dimethoxy-1,1,2,2-tetraphenyldisilane, 1,2-diethoxy-1,1,2,2-tetraphenyldisilane Etc. are preferred.
更に、前記一般式(7)において、c=1である場合の化合物としては、ビス(トリメトキシシリル)メタン、ビス(トリエトキシシリル)メタン、ビス(トリ−n−プロポキシシリル)メタン、ビス(トリ−イソプロポキシシリル)メタン、ビス(トリ−n−ブトキシシリル)メタン、ビス(トリ−sec−ブトキシシリル)メタン、ビス(トリ−tert−ブトキシシリル)メタン、1,2−ビス(トリメトキシシリル)エタン、1,2−ビス(トリエトキシシリル)エタン、1,2−ビス(トリ−n−プロポキシシリル)エタン、1,2−ビス(トリ−イソプロポキシシリル)エタン、1,2−ビス(トリ−n−ブトキシシリル)エタン、1,2−ビス(トリ−sec−ブトキシシリル)エタン、1,2−ビス(トリ−tert−ブトキシシリル)エタン、1−(ジメトキシメチルシリル)−1−(トリメトキシシリル)メタン、1−(ジエトキシメチルシリル)−1−(トリエトキシシリル)メタン、1−(ジ−n−プロポキシメチルシリル)−1−(トリ−n−プロポキシシリル)メタン、1−(ジ−イソプロポキシメチルシリル)−1−(トリ−イソプロポキシシリル)メタン、1−(ジ−n−ブトキシメチルシリル)−1−(トリ−n−ブトキシシリル)メタン、1−(ジ−sec−ブトキシメチルシリル)−1−(トリ−sec−ブトキシシリル)メタン、1−(ジ−tert−ブトキシメチルシリル)−1−(トリ−tert−ブトキシシリル)メタン、1−(ジメトキシメチルシリル)−2−(トリメトキシシリル)エタン、1−(ジエトキシメチルシリル)−2−(トリエトキシシリル)エタン、1−(ジ−n−プロポキシメチルシリル)−2−(トリ−n−プロポキシシリル)エタン、1−(ジ−イソプロポキシメチルシリル)−2−(トリ−イソプロポキシシリル)エタン、1−(ジ−n−ブトキシメチルシリル)−2−(トリ−n−ブトキシシリル)エタン、1−(ジ−sec−ブトキシメチルシリル)−2−(トリ−sec−ブトキシシリル)エタン、1−(ジ−tert−ブトキシメチルシリル)−2−(トリ−tert−ブトキシシリル)エタン、 Furthermore, in the general formula (7), the compounds in the case where c = 1 include bis (trimethoxysilyl) methane, bis (triethoxysilyl) methane, bis (tri-n-propoxysilyl) methane, bis ( Tri-isopropoxysilyl) methane, bis (tri-n-butoxysilyl) methane, bis (tri-sec-butoxysilyl) methane, bis (tri-tert-butoxysilyl) methane, 1,2-bis (trimethoxysilyl) ) Ethane, 1,2-bis (triethoxysilyl) ethane, 1,2-bis (tri-n-propoxysilyl) ethane, 1,2-bis (tri-isopropoxysilyl) ethane, 1,2-bis ( Tri-n-butoxysilyl) ethane, 1,2-bis (tri-sec-butoxysilyl) ethane, 1,2-bis (tri-tert-but) Sisilyl) ethane, 1- (dimethoxymethylsilyl) -1- (trimethoxysilyl) methane, 1- (diethoxymethylsilyl) -1- (triethoxysilyl) methane, 1- (di-n-propoxymethylsilyl) -1- (tri-n-propoxysilyl) methane, 1- (di-isopropoxymethylsilyl) -1- (tri-isopropoxysilyl) methane, 1- (di-n-butoxymethylsilyl) -1- ( Tri-n-butoxysilyl) methane, 1- (di-sec-butoxymethylsilyl) -1- (tri-sec-butoxysilyl) methane, 1- (di-tert-butoxymethylsilyl) -1- (tri- tert-butoxysilyl) methane, 1- (dimethoxymethylsilyl) -2- (trimethoxysilyl) ethane, 1- (diethoxymethylsilyl) 2- (triethoxysilyl) ethane, 1- (di-n-propoxymethylsilyl) -2- (tri-n-propoxysilyl) ethane, 1- (di-isopropoxymethylsilyl) -2- (tri-iso Propoxysilyl) ethane, 1- (di-n-butoxymethylsilyl) -2- (tri-n-butoxysilyl) ethane, 1- (di-sec-butoxymethylsilyl) -2- (tri-sec-butoxysilyl) ) Ethane, 1- (di-tert-butoxymethylsilyl) -2- (tri-tert-butoxysilyl) ethane,
ビス(ジメトキシメチルシリル)メタン、ビス(ジエトキシメチルシリル)メタン、ビス(ジ−n−プロポキシメチルシリル)メタン、ビス(ジ−イソプロポキシメチルシリル)メタン、ビス(ジ−n−ブトキシメチルシリル)メタン、ビス(ジ−sec−ブトキシメチルシリル)メタン、ビス(ジ−tert−ブトキシメチルシリル)メタン、1,2−ビス(ジメトキシメチルシリル)エタン、1,2−ビス(ジエトキシメチルシリル)エタン、1,2−ビス(ジ−n−プロポキシメチルシリル)エタン、1,2−ビス(ジ−イソプロポキシメチルシリル)エタン、1,2−ビス(ジ−n−ブトキシメチルシリル)エタン、1,2−ビス(ジ−sec−ブトキシメチルシリル)エタン、1,2−ビス(ジ−tert−ブトキシメチルシリル)エタン、1,2−ビス(トリメトキシシリル)ベンゼン、1,2−ビス(トリエトキシシリル)ベンゼン、1,2−ビス(トリ−n−プロポキシシリル)ベンゼン、1,2−ビス(トリ−イソプロポキシシリル)ベンゼン、1,2−ビス(トリ−n−ブトキシシリル)ベンゼン、1,2−ビス(トリ−sec−ブトキシシリル)ベンゼン、1,2−ビス(トリ−tert−ブトキシシリル)ベンゼン、1,3−ビス(トリメトキシシリル)ベンゼン、1,3−ビス(トリエトキシシリル)ベンゼン、1,3−ビス(トリ−n−プロポキシシリル)ベンゼン、1,3−ビス(トリ−イソプロポキシシリル)ベンゼン、1,3−ビス(トリ−n−ブトキシシリル)ベンゼン、1,3−ビス(トリ−sec−ブトキシシリル)ベンゼン、1,3−ビス(トリ−tert−ブトキシシリル)ベンゼン、1,4−ビス(トリメトキシシリル)ベンゼン、1,4−ビス(トリエトキシシリル)ベンゼン、1,4−ビス(トリ−n−プロポキシシリル)ベンゼン、1,4−ビス(トリ−イソプロポキシシリル)ベンゼン、1,4−ビス(トリ−n−ブトキシシリル)ベンゼン、1,4−ビス(トリ−sec−ブトキシシリル)ベンゼン、1,4−ビス(トリ−tert−ブトキシシリル)ベンゼン等が挙げられる。 Bis (dimethoxymethylsilyl) methane, bis (diethoxymethylsilyl) methane, bis (di-n-propoxymethylsilyl) methane, bis (di-isopropoxymethylsilyl) methane, bis (di-n-butoxymethylsilyl) Methane, bis (di-sec-butoxymethylsilyl) methane, bis (di-tert-butoxymethylsilyl) methane, 1,2-bis (dimethoxymethylsilyl) ethane, 1,2-bis (diethoxymethylsilyl) ethane 1,2-bis (di-n-propoxymethylsilyl) ethane, 1,2-bis (di-isopropoxymethylsilyl) ethane, 1,2-bis (di-n-butoxymethylsilyl) ethane, 1, 2-bis (di-sec-butoxymethylsilyl) ethane, 1,2-bis (di-tert-butoxymethylsilyl) Ethane, 1,2-bis (trimethoxysilyl) benzene, 1,2-bis (triethoxysilyl) benzene, 1,2-bis (tri-n-propoxysilyl) benzene, 1,2-bis (tri-iso Propoxysilyl) benzene, 1,2-bis (tri-n-butoxysilyl) benzene, 1,2-bis (tri-sec-butoxysilyl) benzene, 1,2-bis (tri-tert-butoxysilyl) benzene, 1,3-bis (trimethoxysilyl) benzene, 1,3-bis (triethoxysilyl) benzene, 1,3-bis (tri-n-propoxysilyl) benzene, 1,3-bis (tri-isopropoxysilyl) ) Benzene, 1,3-bis (tri-n-butoxysilyl) benzene, 1,3-bis (tri-sec-butoxysilyl) benzene, 1,3- (Tri-tert-butoxysilyl) benzene, 1,4-bis (trimethoxysilyl) benzene, 1,4-bis (triethoxysilyl) benzene, 1,4-bis (tri-n-propoxysilyl) benzene, 1,4-bis (tri-isopropoxysilyl) benzene, 1,4-bis (tri-n-butoxysilyl) benzene, 1,4-bis (tri-sec-butoxysilyl) benzene, 1,4-bis ( And tri-tert-butoxysilyl) benzene.
これらの化合物(c=1である場合の化合物)のなかでも、ビス(トリメトキシシリル)メタン、ビス(トリエトキシシリル)メタン、1,2−ビス(トリメトキシシリル)エタン、1,2−ビス(トリエトキシシリル)エタン、1−(ジメトキシメチルシリル)−1−(トリメトキシシリル)メタン、1−(ジエトキシメチルシリル)−1−(トリエトキシシリル)メタン、1−(ジメトキシメチルシリル)−2−(トリメトキシシリル)エタン、1−(ジエトキシメチルシリル)−2−(トリエトキシシリル)エタン、ビス(ジメトキシメチルシリル)メタン、ビス(ジエトキシメチルシリル)メタン、1,2−ビス(ジメトキシメチルシリル)エタン、1,2−ビス(ジエトキシメチルシリル)エタン、1,2−ビス(トリメトキシシリル)ベンゼン、1,2−ビス(トリエトキシシリル)ベンゼン、1,3−ビス(トリメトキシシリル)ベンゼン、1,3−ビス(トリエトキシシリル)ベンゼン、1,4−ビス(トリメトキシシリル)ベンゼン、1,4−ビス(トリエトキシシリル)ベンゼン等が好ましい。
尚、前記一般式(7)で表される化合物(a3)は、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
Among these compounds (compounds where c = 1), bis (trimethoxysilyl) methane, bis (triethoxysilyl) methane, 1,2-bis (trimethoxysilyl) ethane, 1,2-bis (Triethoxysilyl) ethane, 1- (dimethoxymethylsilyl) -1- (trimethoxysilyl) methane, 1- (diethoxymethylsilyl) -1- (triethoxysilyl) methane, 1- (dimethoxymethylsilyl)- 2- (trimethoxysilyl) ethane, 1- (diethoxymethylsilyl) -2- (triethoxysilyl) ethane, bis (dimethoxymethylsilyl) methane, bis (diethoxymethylsilyl) methane, 1,2-bis ( Dimethoxymethylsilyl) ethane, 1,2-bis (diethoxymethylsilyl) ethane, 1,2-bis (trimethoxysilane) L) benzene, 1,2-bis (triethoxysilyl) benzene, 1,3-bis (trimethoxysilyl) benzene, 1,3-bis (triethoxysilyl) benzene, 1,4-bis (trimethoxysilyl) Benzene, 1,4-bis (triethoxysilyl) benzene and the like are preferable.
In addition, the compound (a3) represented by the said General formula (7) may be used individually by 1 type, and may be used in combination of 2 or more type.
(1−1−4)他の化合物(a4)
前記加水分解性シラン化合物は、必要に応じて、下記一般式(4)で表わされる有機ケイ素化合物(以下、「化合物(a4)」ともいう。)を更に含んでいてもよい。
(1-1-4) Other compound (a4)
The hydrolyzable silane compound may further contain an organosilicon compound represented by the following general formula (4) (hereinafter also referred to as “compound (a4)”) as necessary.
前記一般式(8)のR17における炭素数2〜6のアルケニル基としては、下記一般式(i)で表される基であることが好ましい。 The alkenyl group having 2 to 6 carbon atoms in R 17 of the general formula (8) is preferably a group represented by the following general formula (i).
前記一般式(i)におけるnは、0〜4の整数であり、好ましくは0〜2の整数、更に好ましくは0又は1である。 N in the said general formula (i) is an integer of 0-4, Preferably it is an integer of 0-2, More preferably, it is 0 or 1.
また、前記一般式(i)で表される基以外のアルケニル基としては、例えば、ブテニル基、ペンテニル基、ヘキセニル基等が挙げられる。 Examples of the alkenyl group other than the group represented by the general formula (i) include a butenyl group, a pentenyl group, and a hexenyl group.
また、前記一般式(8)のR18における「1価の有機基」については、前記一般式(5)のR9における「1価の有機基」の説明をそのまま適用することができる。尚、前記R18が複数存在する場合(即ち、前記eが1又は2である場合)、各R18は全て同一であってもよいし、全て又は一部が異なっていてもよい。 In addition, regarding the “monovalent organic group” in R 18 of the general formula (8), the description of the “monovalent organic group” in R 9 of the general formula (5) can be applied as it is. When a plurality of R 18 are present (that is, when e is 1 or 2), all R 18 may be the same, or all or part of them may be different.
前記一般式(8)で表される化合物(a4)の具体例としては、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリ−n−プロポキシシラン、ビニルトリイソプロポキシシラン、ビニルトリ−n−ブトキシシラン、ビニルトリ−sec−ブトキシシラン、ビニルトリ−tert−ブトキシシラン、ビニルトリフェノキシシラン、アリルトリメトキシシラン、アリルトリエトキシシラン、アリルトリ−n−プロポキシシラン、アリルトリイソプロポキシシラン、アリルトリ−n−ブトキシシラン、アリルトリ−sec−ブトキシシラン、アリルトリ−tert−ブトキシシラン、アリルトリフェノキシシラン等が挙げられる。 Specific examples of the compound (a4) represented by the general formula (8) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri-n-propoxysilane, vinyltriisopropoxysilane, vinyltri-n-butoxysilane, Vinyltri-sec-butoxysilane, vinyltri-tert-butoxysilane, vinyltriphenoxysilane, allyltrimethoxysilane, allyltriethoxysilane, allyltri-n-propoxysilane, allyltriisopropoxysilane, allyltri-n-butoxysilane, allyltri -Sec-butoxysilane, allyltri-tert-butoxysilane, allyltriphenoxysilane and the like.
これらの化合物(a4)のなかでも、ビニルトリメトキシシラン、ビニルトリエトキシシラン、アリルトリメトキシシラン、アリルトリエトキシシラン等が好ましい。
尚、前記一般式(8)で表される化合物(a4)は、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
Of these compounds (a4), vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, allyltriethoxysilane and the like are preferable.
In addition, the compound (a4) represented with the said General formula (8) may be used individually by 1 type, and may be used in combination of 2 or more type.
(1−1−5)ポリシロキサン(A)の性質
前記ポリシロキサン(A)における、前記化合物(a1)由来の構造単位の含有割合は、ポリシロキサン(A)に含まれる全ての構造単位の合計を100モル%とした場合に、1〜30モル%であることが好ましく、より好ましくは5〜30モル%、更に好ましくは5〜20モル%である。この含有割合が1〜30モル%である場合には、リソパターンを形成する際、現像液に対する未露光部のネガ型感放射線性組成物の溶解性がよく、且つ露光部のパターンが倒れにくいため好ましい。
また、前記化合物(a2)由来の構造単位の含有割合は、ポリシロキサン(A)に含まれる全ての構造単位の合計を100モル%とした場合に、10〜95モル%であることが好ましく、より好ましくは20〜90、更に好ましくは30〜90モル%である。この含有割合が30〜90モル%である場合には、リソパターンを形成する際、現像液に対する未露光部のネガ型感放射線性組成物の溶解性がよく、且つ露光部のパターンが倒れにくいため好ましい。
更に、前記化合物(a1)由来の構造単位及び化合物(a2)由来の構造単位の合計は、ポリシロキサン(A)に含まれる全ての構造単位の合計を100モル%とした場合に、10〜100モル%であることが好ましく、より好ましくは30〜100モル%、更に好ましくは50〜100モル%である。この含有割合の合計が10〜100モル%である場合には、リソパターンを形成する際、現像液に対する未露光部のネガ型感放射線性組成物の溶解性がよく、且つ露光部のパターンが倒れにくいため好ましい。
(1-1-5) Properties of polysiloxane (A) The content ratio of the structural unit derived from the compound (a1) in the polysiloxane (A) is the sum of all the structural units contained in the polysiloxane (A). Is preferably 1 to 30 mol%, more preferably 5 to 30 mol%, still more preferably 5 to 20 mol%. When the content ratio is 1 to 30 mol%, when forming a litho pattern, the negative radiation-sensitive composition in the unexposed area with respect to the developer has good solubility, and the pattern in the exposed area is not easily collapsed. Therefore, it is preferable.
Further, the content ratio of the structural unit derived from the compound (a2) is preferably 10 to 95 mol% when the total of all the structural units contained in the polysiloxane (A) is 100 mol%, More preferably, it is 20-90, More preferably, it is 30-90 mol%. When the content ratio is 30 to 90 mol%, when forming a litho pattern, the negative radiation-sensitive composition in the unexposed area with respect to the developer has good solubility, and the pattern in the exposed area is not easily collapsed. Therefore, it is preferable.
Furthermore, the total of the structural unit derived from the compound (a1) and the structural unit derived from the compound (a2) is 10 to 100 when the total of all the structural units contained in the polysiloxane (A) is 100 mol%. It is preferable that it is mol%, More preferably, it is 30-100 mol%, More preferably, it is 50-100 mol%. When the total content is 10 to 100 mol%, when forming a litho pattern, the negative-type radiation-sensitive composition in the unexposed part in the developer has good solubility, and the pattern in the exposed part is It is preferable because it does not fall easily.
また、前記化合物(a3)由来の構造単位の含有割合は、ポリシロキサン(A)に含まれる全ての構造単位の合計を100モル%とした場合に、30モル%以下であることが好ましく、より好ましくは5〜30モル%、更に好ましくは5〜20モル%である。この含有割合が30モル%以下である場合には、硬化処理後の膜収縮(パターン収縮)が比較的小さく、露光部のパターンが倒れにくいため好ましい。
更に、前記化合物(a4)由来の構造単位の含有割合は、ポリシロキサン(A)に含まれる全ての構造単位の合計を100モル%とした場合に、60モル%以下であることが好ましく、より好ましくは5〜50モル%、更に好ましくは10〜40モル%である。この含有割合が60モル%以下である場合には、硬化処理後の膜収縮(パターン収縮)が比較的小さいため好ましい。
Further, the content ratio of the structural unit derived from the compound (a3) is preferably 30% by mole or less, when the total of all the structural units contained in the polysiloxane (A) is 100% by mole, Preferably it is 5-30 mol%, More preferably, it is 5-20 mol%. When the content ratio is 30 mol% or less, the film shrinkage (pattern shrinkage) after the curing treatment is relatively small and the pattern of the exposed portion is not easily collapsed, which is preferable.
Furthermore, the content ratio of the structural unit derived from the compound (a4) is preferably 60% by mole or less when the total of all the structural units contained in the polysiloxane (A) is 100% by mole, Preferably it is 5-50 mol%, More preferably, it is 10-40 mol%. When the content ratio is 60 mol% or less, film shrinkage (pattern shrinkage) after the curing treatment is relatively small, which is preferable.
また、前記ポリシロキサン(A)における炭素原子の含有率は、このポリシロキサン(A)を構成する全原子数を100原子%とした場合に、8〜40原子%であることが好ましく、より好ましくは8〜20原子%である。この含有率が8原子%未満の場合、ポリシロキサン(A)を含む感放射線性組成物を用いてシリカ系膜を形成した場合、比誘電率が十分に低い膜を得ることが困難である。一方、40原子%を超える場合、硬化処理後の膜収縮(パターン収縮)が大きく、所望のパターンが得られ難くなる。
尚、ポリシロキサン(A)の炭素原子の含有率(原子%)は、ポリシロキサン(A)の合成に用いた成分(加水分解性シラン化合物)の加水分解性基が完全に加水分解されてシラノール基となり、この生成したシラノール基が完全に縮合しシロキサン結合を形成した際の元素組成から求められ、具体的には以下の式から求められる。
炭素原子の含有率(原子%)=(有機シリカゾルの炭素原子数)/(有機シリカゾルの総原子数)×100
Further, the carbon atom content in the polysiloxane (A) is preferably 8 to 40 atom%, more preferably when the total number of atoms constituting the polysiloxane (A) is 100 atom%. Is 8 to 20 atomic%. When this content is less than 8 atomic%, when a silica-based film is formed using a radiation-sensitive composition containing polysiloxane (A), it is difficult to obtain a film having a sufficiently low relative dielectric constant. On the other hand, when it exceeds 40 atomic%, film shrinkage (pattern shrinkage) after the curing treatment is large, and it becomes difficult to obtain a desired pattern.
The content (atomic%) of carbon atoms in the polysiloxane (A) is determined by silanol which is obtained by completely hydrolyzing the hydrolyzable group of the component (hydrolyzable silane compound) used in the synthesis of the polysiloxane (A). It is obtained from the elemental composition when the generated silanol group is completely condensed to form a siloxane bond, and is specifically obtained from the following formula.
Carbon atom content (atomic%) = (number of carbon atoms in organic silica sol) / (total number of atoms in organic silica sol) × 100
前記ポリシロキサン(A)の重量平均分子量(以下、「Mw」ともいう。)は、1,000〜200,000であることが好ましく、より好ましくは5,000〜150,000である。このMwが200,000を超える場合、ゲル化が生じやすい。一方、1,000未満の場合、塗布性や保存安定性に問題が生じやすい。
尚、前記Mwは、ゲルパーミエーションクロマトグラフィー(GPC)により測定されたポリスチレン換算値である。
The weight average molecular weight (hereinafter also referred to as “Mw”) of the polysiloxane (A) is preferably 1,000 to 200,000, and more preferably 5,000 to 150,000. When this Mw exceeds 200,000, gelation tends to occur. On the other hand, if it is less than 1,000, problems are likely to occur in applicability and storage stability.
The Mw is a polystyrene equivalent value measured by gel permeation chromatography (GPC).
(1−1−6)ポリシロキサン(A)の製造方法
前記ポリシロキサン(A)は、加水分解性シラン化合物、即ち、前記化合物(a1)〜(a4)を出発原料として、この出発原料を有機溶媒中に溶解し、この溶液中に水を断続的に或いは連続的に添加して、加水分解縮合反応させることにより製造することができる。このとき、触媒を用いてもよい。この触媒は、予め、有機溶媒中に溶解又は分散させておいてもよく、添加される水中に溶解又は分散させておいてもよい。また、加水分解縮合反応を行うための温度は、通常、0℃〜100℃である。
(1-1-6) Production Method of Polysiloxane (A) The polysiloxane (A) is a hydrolyzable silane compound, that is, the compounds (a1) to (a4) as starting materials, and the starting materials are organic. It can be produced by dissolving in a solvent, adding water intermittently or continuously to the solution, and causing a hydrolysis condensation reaction. At this time, a catalyst may be used. This catalyst may be dissolved or dispersed in advance in an organic solvent, or may be dissolved or dispersed in the water to be added. Moreover, the temperature for performing a hydrolysis-condensation reaction is 0 degreeC-100 degreeC normally.
また、前記出化合物(a1)及び(a2)を用いてポリシロキサン(A)を製造する場合、化合物(a1)及び(a2)の反応比(モル比)、即ち、化合物(a1)/化合物(a2)比は、5/95〜95/5であることが好ましく、より好ましくは10/90〜90/10、更に好ましくは10/90である。この反応比が、5/95〜95/5である場合、リソパターンを形成する際、現像液に対する未露光部のネガ型感放射線性組成物の溶解性がよく、且つ露光部のパターンが倒れにくいため好ましい。 Moreover, when manufacturing polysiloxane (A) using the said outgoing compounds (a1) and (a2), the reaction ratio (molar ratio) of a compound (a1) and (a2), ie, a compound (a1) / compound ( a2) The ratio is preferably 5/95 to 95/5, more preferably 10/90 to 90/10, still more preferably 10/90. When this reaction ratio is 5/95 to 95/5, when forming a litho pattern, the negative radiation-sensitive composition in the unexposed area with respect to the developer has good solubility and the exposed area pattern collapses. It is preferable because it is difficult.
前記加水分解縮合反応を行うための水としては、特に限定されないが、イオン交換水を用いることが好ましい。また、前記水は、用いられる加水分解性シラン化合物のアルコキシル基1モル当たり0.25〜3モル、好ましくは0.3〜2.5モルとなる量で用いられる。上述の範囲の量で水を用いることにより、形成される塗膜の均一性が低下するおそれがなく、且つ、組成物の保存安定性が低下するおそれが少ない。 Although it does not specifically limit as water for performing the said hydrolysis-condensation reaction, It is preferable to use ion-exchange water. Moreover, the said water is used in the quantity used as 0.25-3 mol with respect to 1 mol of alkoxyl groups of the hydrolysable silane compound used, Preferably it is 0.3-2.5 mol. By using water in an amount in the above range, there is no possibility that the uniformity of the formed coating film will be lowered, and there is little possibility that the storage stability of the composition will be lowered.
前記有機溶媒は、特に限定されず、例えば、プロピレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノプロピルエーテル等が挙げられる。 The organic solvent is not particularly limited, and examples thereof include propylene glycol monoethyl ether, propylene glycol monomethyl ether, and propylene glycol monopropyl ether.
前記触媒としては、金属キレート化合物、有機酸、無機酸、有機塩基、無機塩基等が挙げられる。
前記金属キレート化合物としては、例えば、チタンキレート化合物、ジルコニウムキレート化合物、アルミニウムキレート化合物等が挙げられる。具体的には、特開2000−356854号公報等に記載されている化合物等を用いることができる。
前記有機酸としては、例えば、酢酸、プロピオン酸、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、シュウ酸、マレイン酸、メチルマロン酸、アジピン酸、セバシン酸、没食子酸、酪酸、メリット酸、アラキドン酸、ミキミ酸、2−エチルヘキサン酸、オレイン酸、ステアリン酸、リノール酸、リノレイン酸、サリチル酸、安息香酸、p−アミノ安息香酸、p−トルエンスルホン酸、ベンゼンスルホン酸、モノクロロ酢酸、ジクロロ酢酸、トリクロロ酢酸、トリフルオロ酢酸、ギ酸、マロン酸、スルホン酸、フタル酸、フマル酸、クエン酸、酒石酸等が挙げられる。
前記無機酸としては、例えば、塩酸、硝酸、硫酸、フッ酸、リン酸等が挙げられる。
Examples of the catalyst include metal chelate compounds, organic acids, inorganic acids, organic bases, and inorganic bases.
Examples of the metal chelate compound include a titanium chelate compound, a zirconium chelate compound, and an aluminum chelate compound. Specifically, compounds described in JP 2000-356854 A can be used.
Examples of the organic acid include acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, sebacic acid, Gallic acid, butyric acid, merit acid, arachidonic acid, mykimic acid, 2-ethylhexanoic acid, oleic acid, stearic acid, linoleic acid, linolenic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, p-toluenesulfonic acid, benzene Examples include sulfonic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, formic acid, malonic acid, sulfonic acid, phthalic acid, fumaric acid, citric acid, and tartaric acid.
Examples of the inorganic acid include hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, and phosphoric acid.
前記有機塩基としては、例えば、ピリジン、ピロール、ピペラジン、ピロリジン、ピペリジン、ピコリン、トリメチルアミン、トリエチルアミン、モノエタノールアミン、ジエタノールアミン、ジメチルモノエタノールアミン、モノメチルジエタノールアミン、トリエタノールアミン、ジアザビシクロオクラン、ジアザビシクロノナン、ジアザビシクロウンデセン、テトラメチルアンモニウムハイドロオキサイド等が挙げられる。
前記無機塩基としては、例えば、アンモニア、水酸化ナトリウム、水酸化カリウム、水酸化バリウム、水酸化カルシウム等が挙げられる。
Examples of the organic base include pyridine, pyrrole, piperazine, pyrrolidine, piperidine, picoline, trimethylamine, triethylamine, monoethanolamine, diethanolamine, dimethylmonoethanolamine, monomethyldiethanolamine, triethanolamine, diazabicycloocrane, diaza Bicyclononane, diazabicycloundecene, tetramethylammonium hydroxide and the like can be mentioned.
Examples of the inorganic base include ammonia, sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide and the like.
これらの触媒のなかでも、金属キレート化合物、有機酸及び無機酸が好ましい。
また、こられの触媒は、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
Of these catalysts, metal chelate compounds, organic acids and inorganic acids are preferred.
Moreover, these catalysts may be used individually by 1 type, and may be used in combination of 2 or more type.
前記触媒の使用量は、前記加水分解性シラン化合物100質量部に対して、通常、0.001〜10質量部、好ましくは0.01〜10質量部である。 The usage-amount of the said catalyst is 0.001-10 mass parts normally with respect to 100 mass parts of said hydrolysable silane compounds, Preferably it is 0.01-10 mass parts.
また、加水分解縮合反応を行った後には、メタノール、エタノール等の低級アルコール類等の反応副生成物の除去処理を行うことが好ましい。これにより、前記有機溶媒の純度が高くなるため、優れた塗布性を有し、しかも、良好な保存安定性を有する組成物を得ることができる。
反応副生成物の除去処理の方法としては、加水分解物及び/又はその縮合物の反応が進行しない方法であれば特に限定されず、反応副生成物の沸点が前記有機溶媒の沸点より低いものである場合には、減圧によって留去することができる。
Further, after the hydrolysis condensation reaction, it is preferable to perform a removal treatment of reaction by-products such as lower alcohols such as methanol and ethanol. Thereby, since the purity of the organic solvent is increased, it is possible to obtain a composition having excellent coating properties and excellent storage stability.
The method for removing the reaction by-product is not particularly limited as long as the reaction of the hydrolyzate and / or its condensate does not proceed, and the boiling point of the reaction by-product is lower than the boiling point of the organic solvent. , It can be distilled off under reduced pressure.
また、本発明におけるポリシロキサン(A)は、重合体溶液から単離して用いてもよいし、重合体溶液のまま用いてもよい。尚、重合体溶液として用いる場合、必要に応じて、後述の溶剤(D)に溶剤置換されたものであってもよい。 Moreover, the polysiloxane (A) in the present invention may be used after being isolated from the polymer solution, or may be used as it is. In addition, when using as a polymer solution, the solvent substituted by the below-mentioned solvent (D) may be used as needed.
本発明のネガ型感放射線性組成物において、前記ポリシロキサン(A)は、1種のみ含まれていてもよいし、2種以上含まれていてもよい。 In the negative radiation sensitive composition of the present invention, the polysiloxane (A) may be included in one kind or two or more kinds.
(1−2)酸発生剤(B)
前記酸発生剤(B)は、露光により酸を発生するものであり、露光により発生した酸の作用によって、樹脂成分が架橋し、その結果レジスト被膜の露光部がアルカリ現像液に難溶性となり、ネガ型のレジストパターンを形成する作用を有するものである。
この酸発生剤(B)としては、例えば、スルホニウム塩やヨードニウム塩等のオニウム塩、有機ハロゲン化合物、ジスルホン類やジアゾメタンスルホン類等のスルホン化合物等が挙げられる。
(1-2) Acid generator (B)
The acid generator (B) generates an acid upon exposure, and the resin component is cross-linked by the action of the acid generated by the exposure. As a result, the exposed portion of the resist film becomes hardly soluble in an alkali developer. It has the function of forming a negative resist pattern.
Examples of the acid generator (B) include onium salts such as sulfonium salts and iodonium salts, organic halogen compounds, sulfone compounds such as disulfones and diazomethane sulfones, and the like.
前記酸発生剤(B)の好ましい具体例としては、例えば、トリフェニルスルホニウムトリフルオロメタンスルホネート、トリフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、トリフェニルスルホニウムパーフルオロ−n−オクタンスルホネート、トリフェニルスルホニウム2−ビシクロ[2.2.1]ヘプト−2−イル−1,1,2,2−テトラフルオロエタンスルホネート、トリフェニルスルホニウム2−(3−テトラシクロ[4.4.0.12,5.17,10]ドデカニル)−1,1−ジフルオロエタンスルホネート、トリフェニルスルホニウムN,N’−ビス(ノナフルオロ−n−ブタンスルホニル)イミデート、トリフェニルスルホニウムカンファースルホネート等のトリフェニルスルホニウム塩化合物; Preferable specific examples of the acid generator (B) include, for example, triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium nonafluoro-n-butanesulfonate, triphenylsulfonium perfluoro-n-octanesulfonate, triphenylsulfonium 2- Bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, triphenylsulfonium 2- (3-tetracyclo [4.4.0.1 2,5 .1 7 , 10 ] dodecanyl) -1,1-difluoroethanesulfonate, triphenylsulfonium salt compounds such as triphenylsulfonium N, N′-bis (nonafluoro-n-butanesulfonyl) imidate, triphenylsulfonium camphorsulfonate;
4−シクロヘキシルフェニルジフェニルスルホニウムトリフルオロメタンスルホネート、4−シクロヘキシルフェニルジフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、4−シクロヘキシルフェニルジフェニルスルホニウムパーフルオロ−n−オクタンスルホネート、4−シクロヘキシルフェニルジフェニルスルホニウム2−ビシクロ[2.2.1]ヘプト−2−イル−1,1,2,2−テトラフルオロエタンスルホネート、4−シクロヘキシルフェニルジフェニルスルホニウム2−(3−テトラシクロ[4.4.0.12,5.17,10]ドデカニル)−1,1−ジフルオロエタンスルホネート、4−シクロヘキシルフェニルジフェニルスルホニウムN,N’−ビス(ノナフルオロ−n−ブタンスルホニル)イミデート、4−シクロヘキシルフェニルジフェニルスルホニウムカンファースルホネート等の4−シクロヘキシルフェニルジフェニルスルホニウム塩化合物; 4-cyclohexylphenyldiphenylsulfonium trifluoromethanesulfonate, 4-cyclohexylphenyldiphenylsulfonium nonafluoro-n-butanesulfonate, 4-cyclohexylphenyldiphenylsulfonium perfluoro-n-octanesulfonate, 4-cyclohexylphenyldiphenylsulfonium 2-bicyclo [2. 2.1] hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 4-cyclohexyl-phenyl diphenyl sulfonium 2- (3-tetracyclo [4.4.0.1 2,5 .1 7, 10] dodecanyl) -1,1-difluoroethanesulfonate, 4-cyclohexyl-phenyl diphenyl sulfonium N, N'-bis (nonafluoro -n- butanesulfonyl) imidate 4-cyclohexyl-phenyl diphenyl sulfonium salt compounds such as 4-cyclohexyl-phenyl camphorsulfonate;
4−t−ブチルフェニルジフェニルスルホニウムトリフルオロメタンスルホネート、4−t−ブチルフェニルジフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、4−t−ブチルフェニルジフェニルスルホニウムパーフルオロ−n−オクタンスルホネート、4−t−ブチルフェニルジフェニルスルホニウム2−ビシクロ[2.2.1]ヘプト−2−イル−1,1,2,2−テトラフルオロエタンスルホネート、4−t−ブチルフェニルジフェニルスルホニウム2−(3−テトラシクロ[4.4.0.12,5.17,10]ドデカニル)−1,1−ジフルオロエタンスルホネート、4−t−ブチルフェニルジフェニルスルホニウムN,N’−ビス(ノナフルオロ−n−ブタンスルホニル)イミデート、4−t−ブチルフェニルジフェニルスルホニウムカンファースルホネート等の4−t−ブチルフェニルジフェニルスルホニウム塩化合物; 4-t-butylphenyldiphenylsulfonium trifluoromethanesulfonate, 4-t-butylphenyldiphenylsulfonium nonafluoro-n-butanesulfonate, 4-t-butylphenyldiphenylsulfonium perfluoro-n-octanesulfonate, 4-t-butylphenyl Diphenylsulfonium 2-bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 4-t-butylphenyldiphenylsulfonium 2- (3-tetracyclo [4.4. 0.1 2,5 .1 7,10] dodecanyl) -1,1-difluoroethanesulfonate, 4-t-butylphenyl diphenyl sulfonium N, N'-bis (nonafluoro -n- butanesulfonyl) imidate, 4-t- Butylphenyl 4-t-butylphenyl diphenyl sulfonium salt compounds such as triphenylsulfonium camphorsulfonate;
トリ(4−t−ブチルフェニル)スルホニウムトリフルオロメタンスルホネート、トリ(4−t−ブチルフェニル)スルホニウムノナフルオロ−n−ブタンスルホネート、トリ(4−t−ブチルフェニル)スルホニウムパーフルオロ−n−オクタンスルホネート、トリ(4−t−ブチルフェニル)スルホニウム2−ビシクロ[2.2.1]ヘプト−2−イル−1,1,2,2−テトラフルオロエタンスルホネート、トリ(4−t−ブチルフェニル)スルホニウム2−(3−テトラシクロ[4.4.0.12,5.17,10]ドデカニル)−1,1−ジフルオロエタンスルホネート、トリ(4−t−ブチルフェニル)スルホニウムN,N’−ビス(ノナフルオロ−n−ブタンスルホニル)イミデート、トリ(4−t−ブチルフェニル)スルホニウムカンファースルホネート等のトリ(4−t−ブチルフェニル)スルホニウム塩化合物; Tri (4-t-butylphenyl) sulfonium trifluoromethanesulfonate, tri (4-t-butylphenyl) sulfonium nonafluoro-n-butanesulfonate, tri (4-t-butylphenyl) sulfonium perfluoro-n-octanesulfonate, Tri (4-t-butylphenyl) sulfonium 2-bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, tri (4-t-butylphenyl) sulfonium 2 - (3-tetracyclo [4.4.0.1 2,5 .1 7,10] dodecanyl) -1,1-difluoroethanesulfonate, tri (4-t- butylphenyl) sulfonium N, N'-bis (nonafluoro -N-butanesulfonyl) imidate, tri (4-t-butylphenyl) sulfur Bromide tri (4-t- butylphenyl) such as camphorsulfonate sulfonium salt compound;
ジフェニルヨードニウムトリフルオロメタンスルホネート、ジフェニルヨードニウムノナフルオロ−n−ブタンスルホネート、ジフェニルヨードニウムパーフルオロ−n−オクタンスルホネート、ジフェニルヨードニウム2−ビシクロ[2.2.1]ヘプト−2−イル−1,1,2,2−テトラフルオロエタンスルホネート、ジフェニルヨードニウム2−(3−テトラシクロ[4.4.0.12,5.17,10]ドデカニル)−1,1−ジフルオロエタンスルホネート、ジフェニルヨードニウムN,N’−ビス(ノナフルオロ−n−ブタンスルホニル)イミデート、ジフェニルヨードニウムカンファースルホネート等のジフェニルヨードニウム塩化合物; Diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodonium perfluoro-n-octanesulfonate, diphenyliodonium 2-bicyclo [2.2.1] hept-2-yl-1,1,2, 2-tetrafluoroethane sulfonate, diphenyliodonium 2- (3-tetracyclo [4.4.0.1 2,5 .1 7,10] dodecanyl) -1,1-difluoroethanesulfonate, diphenyliodonium N, N'-bis Diphenyliodonium salt compounds such as (nonafluoro-n-butanesulfonyl) imidate, diphenyliodonium camphorsulfonate;
ビス(4−t−ブチルフェニル)ヨードニウムトリフルオロメタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムパーフルオロ−n−オクタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウム2−ビシクロ[2.2.1]ヘプト−2−イル−1,1,2,2−テトラフルオロエタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウム2−(3−テトラシクロ[4.4.0.12,5.17,10]ドデカニル)−1,1−ジフルオロエタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムN,N’−ビス(ノナフルオロ−n−ブタンスルホニル)イミデート、ビス(4−t−ブチルフェニル)ヨードニウムカンファースルホネート等のビス(4−t−ブチルフェニル)ヨードニウム塩化合物; Bis (4-t-butylphenyl) iodonium trifluoromethanesulfonate, bis (4-t-butylphenyl) iodonium nonafluoro-n-butanesulfonate, bis (4-t-butylphenyl) iodonium perfluoro-n-octanesulfonate, Bis (4-t-butylphenyl) iodonium 2-bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, bis (4-t-butylphenyl) iodonium 2 - (3-tetracyclo [4.4.0.1 2,5 .1 7,10] dodecanyl) -1,1-difluoroethanesulfonate, bis (4-t- butylphenyl) iodonium N, N'-bis (nonafluoro -N-butanesulfonyl) imidate, bis (4-t-butylphenyl) io Bis (4-t- butylphenyl) such as camphorsulfonate iodonium salt compounds;
1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウムノナフルオロ−n−ブタンスルホネート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウムパーフルオロ−n−オクタンスルホネート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウム2−ビシクロ[2.2.1]ヘプト−2−イル−1,1,2,2−テトラフルオロエタンスルホネート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウム2−(3−テトラシクロ[4.4.0.12,5.17,10]ドデカニル)−1,1−ジフルオロエタンスルホネート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウムN,N’−ビス(ノナフルオロ−n−ブタンスルホニル)イミデート、1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウムカンファースルホネート等の1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウム塩化合物; 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium nonafluoro-n-butanesulfonate, (4-n-Butoxynaphthalen-1-yl) tetrahydrothiophenium perfluoro-n-octanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium 2-bicyclo [2.2. 1] Hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium 2- (3-tetracyclo [4.4. 0.1 2,5 .1 7,10 ] dodecanyl) -1,1-difluoroethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium N, N′-bis (nonafluoro-n-butanesulfonyl) imidate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothio 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium salt compounds such as phenium camphorsulfonate;
1−(3,5−ジメチル−4−ヒドロキシフェニル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(3,5−ジメチル−4−ヒドロキシフェニル)テトラヒドロチオフェニウムノナフルオロ−n−ブタンスルホネート、1−(3,5−ジメチル−4−ヒドロキシフェニル)テトラヒドロチオフェニウムパーフルオロ−n−オクタンスルホネート、1−(3,5−ジメチル−4−ヒドロキシフェニル)テトラヒドロチオフェニウム2−ビシクロ[2.2.1]ヘプト−2−イル−1,1,2,2−テトラフルオロエタンスルホネート、1−(3,5−ジメチル−4−ヒドロキシフェニル)テトラヒドロチオフェニウム2−(3−テトラシクロ[4.4.0.12,5.17,10]ドデカニル)−1,1−ジフルオロエタンスルホネート、1−(3,5−ジメチル−4−ヒドロキシフェニル)テトラヒドロチオフェニウムN,N’−ビス(ノナフルオロ−n−ブタンスルホニル)イミデート、1−(3,5−ジメチル−4−ヒドロキシフェニル)テトラヒドロチオフェニウムカンファースルホネート等の1−(3,5−ジメチル−4−ヒドロキシフェニル)テトラヒドロチオフェニウム塩化合物; 1- (3,5-dimethyl-4-hydroxyphenyl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (3,5-dimethyl-4-hydroxyphenyl) tetrahydrothiophenium nonafluoro-n-butanesulfonate, (3,5-Dimethyl-4-hydroxyphenyl) tetrahydrothiophenium perfluoro-n-octanesulfonate, 1- (3,5-dimethyl-4-hydroxyphenyl) tetrahydrothiophenium 2-bicyclo [2.2. 1] Hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 1- (3,5-dimethyl-4-hydroxyphenyl) tetrahydrothiophenium 2- (3-tetracyclo [4.4. 0.1 2,5 .1 7,10 ] dodecanyl) -1,1-difluoro Ethanesulfonate, 1- (3,5-dimethyl-4-hydroxyphenyl) tetrahydrothiophenium N, N′-bis (nonafluoro-n-butanesulfonyl) imidate, 1- (3,5-dimethyl-4-hydroxyphenyl) ) 1- (3,5-dimethyl-4-hydroxyphenyl) tetrahydrothiophenium salt compounds such as tetrahydrothiophenium camphorsulfonate;
N−(トリフルオロメタンスルホニルオキシ)スクシンイミド、N−(ノナフルオロ−n−ブタンスルホニルオキシ)スクシンイミド、N−(パーフルオロ−n−オクタンスルホニルオキシ)スクシンイミド、N−(2−ビシクロ[2.2.1]ヘプト−2−イル−1,1,2,2−テトラフルオロエタンスルホニルオキシ)スクシンイミド、N−(2−(3−テトラシクロ[4.4.0.12,5.17,10]ドデカニル)−1,1−ジフルオロエタンスルホニルオキシ)スクシンイミド、N−(カンファースルホニルオキシ)スクシンイミド等のスクシンイミド類化合物; N- (trifluoromethanesulfonyloxy) succinimide, N- (nonafluoro-n-butanesulfonyloxy) succinimide, N- (perfluoro-n-octanesulfonyloxy) succinimide, N- (2-bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethane sulfonyloxy) succinimide, N- (2- (3- tetracyclo [4.4.0.1 2,5 .1 7,10] dodecanyl) Succinimide compounds such as -1,1-difluoroethanesulfonyloxy) succinimide and N- (camphorsulfonyloxy) succinimide;
N−(トリフルオロメタンスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(ノナフルオロ−n−ブタンスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(パーフルオロ−n−オクタンスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(2−ビシクロ[2.2.1]ヘプト−2−イル−1,1,2,2−テトラフルオロエタンスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(2−(3−テトラシクロ[4.4.0.12,5.17,10]ドデカニル)−1,1−ジフルオロエタンスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(カンファースルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド等のビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド類化合物等が挙げられる。 N- (trifluoromethanesulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (nonafluoro-n-butanesulfonyloxy) bicyclo [2.2.1] hept -5-ene-2,3-dicarboximide, N- (perfluoro-n-octanesulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- ( 2-bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethanesulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboxy imide, N- (2- (3- tetracyclo [4.4.0.1 2,5 .1 7,10] dodecanyl) -1,1-difluoroethane-sulfonyloxy) bicyclo [2.2.1] hept Bicyclo [2.2.1] such as -5-ene-2,3-dicarboximide, N- (camphorsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide. And hept-5-ene-2,3-dicarboximide compounds.
本発明のネガ型感放射線性組成物において、前記酸発生剤(B)は、1種のみ含まれていてもよいし、2種以上含まれていてもよい。 In the negative radiation-sensitive composition of the present invention, the acid generator (B) may be included alone or in combination of two or more.
本発明のネガ型感放射線性組成物に含有される前記酸発生剤(B)の含有量は、前記ポリシロキサン(A)100質量部に対して、1〜30質量部であることが好ましく、より好ましくは0.1〜20質量部、更に好ましくは0.1〜15質量部である。この含有量が、1〜30質量部である場合、感度及び解像度が良好であるため好ましい。 The content of the acid generator (B) contained in the negative radiation-sensitive composition of the present invention is preferably 1 to 30 parts by mass with respect to 100 parts by mass of the polysiloxane (A). More preferably, it is 0.1-20 mass parts, More preferably, it is 0.1-15 mass parts. When this content is 1 to 30 parts by mass, the sensitivity and resolution are good, which is preferable.
(1−3)重合体(C)
前記重合体(C)は、膜形成時に分解させることで、得られる膜に空隙を形成することができ、その結果、比誘電率を低下させる作用を有するものである。
この重合体(C)は、下記一般式(1)で表される構造単位(c1)〔以下、単に「構造単位(c1)」という。〕を含むものである。また、この構造単位(c1)は、重合体(C)に1種のみ含まれていてもよいし、2種以上含まれていてもよい。
(1-3) Polymer (C)
The polymer (C) is capable of forming voids in the resulting film by being decomposed at the time of film formation, and as a result, has an effect of reducing the relative dielectric constant.
The polymer (C) is a structural unit (c1) represented by the following general formula (1) [hereinafter simply referred to as “structural unit (c1)”. ] Is included. Moreover, this structural unit (c1) may be contained only 1 type in the polymer (C), and may be contained 2 or more types.
前記一般式(1)におけるnは0〜8の整数であり、好ましくは0〜6の整数、より好ましくは0〜2の整数である。 N in the said General formula (1) is an integer of 0-8, Preferably it is an integer of 0-6, More preferably, it is an integer of 0-2.
前記構造単位(c1)を与える単量体としては、例えば、下記一般式(m−c1)で表される化合物等を挙げることができる。 Examples of the monomer that gives the structural unit (c1) include compounds represented by the following general formula (m-c1).
前記一般式(m−c1)におけるnは0〜8の整数であり、好ましくは0〜6の整数、より好ましくは0〜2の整数である。 N in the said general formula (m-c1) is an integer of 0-8, Preferably it is an integer of 0-6, More preferably, it is an integer of 0-2.
前記一般式(m−c1)で表される化合物のなかでも、(メタ)アクリル酸テトラヒドロフルフリル、(メタ)アクリル酸グリシジルが好ましい。 Among the compounds represented by the general formula (m-c1), tetrahydrofurfuryl (meth) acrylate and glycidyl (meth) acrylate are preferable.
また、前記重合体(C)は、前記構造単位(c1)以外に、下記一般式(2)で表される構造単位(c2)を更に含んでいてもよい。この構造単位(c2)は、重合体(C)に1種のみ含まれていてもよいし、2種以上含まれていてもよい。 Moreover, the said polymer (C) may further contain the structural unit (c2) represented by following General formula (2) other than the said structural unit (c1). As for this structural unit (c2), only 1 type may be contained in the polymer (C), and 2 or more types may be contained.
前記一般式(2)におけるmは0〜10の整数であり、好ましくは0〜6の整数、より好ましくは0又は1である。 M in the said General formula (2) is an integer of 0-10, Preferably it is an integer of 0-6, More preferably, it is 0 or 1.
前記構造単位(c2)を与える単量体としては、例えば、下記一般式(m−c2)で表される化合物等を挙げることができる。 Examples of the monomer that gives the structural unit (c2) include compounds represented by the following general formula (m-c2).
前記一般式(m−c2)におけるmは0〜10の整数であり、好ましくは0〜6の整数、より好ましくは0又は1である。 M in the said general formula (m-c2) is an integer of 0-10, Preferably it is an integer of 0-6, More preferably, it is 0 or 1.
前記一般式(m−c2)で表される化合物のなかでも、メタクリル酸―4−オキサ−5−オキソ−トリシクロ[4.2.1.03,7]ノナ−2−イルエステルが好ましい。 Among the compounds represented by the general formula (m-c2), methacrylic acid-4-oxa-5-oxo-tricyclo [4.2.1.0 3,7 ] non-2-yl ester is preferable.
また、前記重合体(C)は、前記構造単位(c1)及び(c2)以外に、下記一般式(3)で表される構造単位(c3)、及び下記一般式(4)で表される構造単位(c4)のうちの少なくとも一方を更に含んでいてもよい。これらの構造単位(c3)及び(c4)は、それぞれ、重合体(C)に1種のみ含まれていてもよいし、2種以上含まれていてもよい。 In addition to the structural units (c1) and (c2), the polymer (C) is represented by the structural unit (c3) represented by the following general formula (3) and the following general formula (4). It may further include at least one of the structural units (c4). One of these structural units (c3) and (c4) may be contained in the polymer (C), or two or more thereof may be contained.
前記一般式(3)におけるR6の分岐状のアルキル基としては、例えば、炭素数3〜20の分岐状のアルキル基が好ましい。具体的には、例えば、イソプロピル基、イソブチル基等が挙げられる。 As the branched alkyl group of R 6 in the general formula (3), for example, a branched alkyl group having 3 to 20 carbon atoms is preferable. Specific examples include an isopropyl group and an isobutyl group.
前記構造単位(c3)を与える単量体としては、例えば、下記一般式(m−c3)で表される化合物等を挙げることができる。 Examples of the monomer that provides the structural unit (c3) include compounds represented by the following general formula (m-c3).
前記一般式(m−c3)におけるR6の「分岐状のアルキル基」は、前記一般式(3)におけるR6の「分岐状のアルキル基」と同義である。 The “branched alkyl group” of R 6 in the general formula (m-c3) has the same meaning as the “branched alkyl group” of R 6 in the general formula (3).
前記一般式(m−c3)で表される化合物のなかでも、(メタ)アクリル酸イソブチルが好ましい。 Among the compounds represented by the general formula (m-c3), isobutyl (meth) acrylate is preferable.
前記一般式(4)におけるR8のアルキレン基としては、例えば、炭素数2〜20の直鎖状若しくは分岐状のアルキレン基が好ましい。具体的には、例えば、1,1−エチレン基、1,2−エチレン基、1,2−プロピレン基、1,3−プロピレン基、1,2−ブチレン基、1,3−ブチレン基、1,4−ブチレン基等が挙げられる。これらのなかでも、特に、1,1−エチレン基、1,2−エチレン基等が好ましい。 The alkylene group R 8 in the general formula (4), for example, preferably a linear or branched alkylene group having 2 to 20 carbon atoms. Specifically, for example, 1,1-ethylene group, 1,2-ethylene group, 1,2-propylene group, 1,3-propylene group, 1,2-butylene group, 1,3-butylene group, 1 , 4-butylene group and the like. Among these, 1,1-ethylene group, 1,2-ethylene group and the like are particularly preferable.
前記構造単位(c4)を与える単量体としては、例えば、下記一般式(m−c4)で表される化合物等を挙げることができる。 Examples of the monomer that gives the structural unit (c4) include a compound represented by the following general formula (m-c4).
前記一般式(m−c4)におけるR8の「アルキレン基」は、前記一般式(4)におけるR8の「アルキレン基」と同義である。 The “alkylene group” of R 8 in the general formula (m-c4) has the same meaning as the “alkylene group” of R 8 in the general formula (4).
前記一般式(m−c4)で表される化合物のなかでも、メタクリル酸―2−ヒドロキシエチルが好ましい。 Among the compounds represented by the general formula (m-c4), -2-hydroxyethyl methacrylate is preferable.
前記構造単位(c1)の含有割合は、前記重合体(C)に含まれる全構造単位の合計を100モル%とした場合に、1〜95モル%であることが好ましく、より好ましくは1〜90モル%、更に好ましくは1〜80モル%である。この含有割合が1〜95モル%である場合には、リソパターンを形成する際、露光部のパターンが倒れにくいため好ましい。
また、前記構造単位(c2)の含有割合は、前記重合体(C)に含まれる全構造単位の合計を100モル%とした場合に、1〜95モル%であることが好ましく、より好ましくは1〜90モル%、更に好ましくは1〜80モル%である。この含有割合が1〜95モル%である場合には、リソパターンを形成する際、現像液に対する未露光部のネガ型感放射線性組成物の溶解性を維持することができる。
更に、前記構造単位(c3)の含有割合は、前記重合体(C)に含まれる全構造単位の合計を100モル%とした場合に、1〜90モル%であることが好ましく、より好ましくは1〜80モル%、更に好ましくは1〜50モル%である。この含有割合が1〜90モル%である場合には、リソパターンを形成する際、現像液に対する未露光部のネガ型感放射線性組成物の溶解性を維持することができる。
また、前記構造単位(c4)の含有割合は、前記重合体(C)に含まれる全構造単位の合計を100モル%とした場合に、1〜90モル%であることが好ましく、より好ましくは1〜80モル%、更に好ましくは1〜50モル%である。この含有割合が1〜90モル%である場合には、リソパターンを形成する際、露光部のパターンが倒れにくいため好ましい。
The content ratio of the structural unit (c1) is preferably 1 to 95 mol%, more preferably 1 to 95 mol%, when the total of all the structural units contained in the polymer (C) is 100 mol%. 90 mol%, more preferably 1 to 80 mol%. When the content ratio is 1 to 95 mol%, the pattern of the exposed portion is not easily collapsed when forming a litho pattern.
The content ratio of the structural unit (c2) is preferably 1 to 95 mol%, more preferably 100 mol% when the total of all structural units contained in the polymer (C) is 100 mol%. It is 1-90 mol%, More preferably, it is 1-80 mol%. When this content rate is 1-95 mol%, when forming a litho pattern, the solubility of the negative radiation sensitive composition of the unexposed part with respect to a developing solution can be maintained.
Furthermore, the content ratio of the structural unit (c3) is preferably 1 to 90 mol%, more preferably, when the total of all the structural units contained in the polymer (C) is 100 mol%. It is 1-80 mol%, More preferably, it is 1-50 mol%. When this content rate is 1-90 mol%, when forming a litho pattern, the solubility of the negative radiation sensitive composition of the unexposed part with respect to a developing solution can be maintained.
Further, the content ratio of the structural unit (c4) is preferably 1 to 90 mol%, more preferably, when the total of all structural units contained in the polymer (C) is 100 mol%. It is 1-80 mol%, More preferably, it is 1-50 mol%. A content ratio of 1 to 90 mol% is preferable because the pattern of the exposed portion is not easily collapsed when forming a litho pattern.
前記重合体(C)は、例えば、前記構造単位(c1)〜(c4)を与える前述の各化合物を、ヒドロパーオキシド類、ジアルキルパーオキシド類、ジアシルパーオキシド類、アゾ化合物等のラジカル重合開始剤を使用し、必要に応じて連鎖移動剤の存在下、適当な溶媒中で重合することにより製造することができる。
重合に使用される溶媒としては、n−ペンタン、n−ヘキサン、n−ヘプタン、n−オクタン、n−ノナン、n−デカン等のアルカン類;シクロヘキサン、シクロヘプタン、シクロオクタン、デカリン、ノルボルナン等のシクロアルカン類;ベンゼン、トルエン、キシレン、エチルベンゼン、クメン等の芳香族炭化水素類;クロロブタン類、ブロモヘキサン類、ジクロロエタン類、ヘキサメチレンジブロミド、クロロベンゼン等のハロゲン化炭化水素類;酢酸エチル、酢酸n−ブチル、酢酸イソブチル、プロピオン酸メチル等の飽和カルボン酸エステル類;2−ブタノン、4−メチル−2−ペンタノン、2−ヘプタノン等のケトン類;テトラヒドロフラン、ジメトキシエタン類、ジエトキシエタン類等のエーエル類等が挙げられる。
これらの溶媒は、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。 重合における反応温度は、通常、40〜120℃、好ましくは50〜90℃である。また、反応時間は、通常、1〜48時間、好ましくは1〜24時間である。
In the polymer (C), for example, the above-mentioned compounds that give the structural units (c1) to (c4) are converted into radical polymerization initiators such as hydroperoxides, dialkyl peroxides, diacyl peroxides, and azo compounds. It can manufacture by superposing | polymerizing in a suitable solvent in presence of a chain transfer agent using an agent as needed.
Solvents used for polymerization include alkanes such as n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane; cyclohexane, cycloheptane, cyclooctane, decalin, norbornane, etc. Cycloalkanes; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene; halogenated hydrocarbons such as chlorobutanes, bromohexanes, dichloroethanes, hexamethylene dibromide, chlorobenzene; ethyl acetate, acetic acid n Saturated carboxylic acid esters such as butyl, isobutyl acetate and methyl propionate; ketones such as 2-butanone, 4-methyl-2-pentanone and 2-heptanone; air such as tetrahydrofuran, dimethoxyethanes and diethoxyethanes And the like.
These solvents may be used alone or in combination of two or more. The reaction temperature in the polymerization is usually 40 to 120 ° C, preferably 50 to 90 ° C. The reaction time is usually 1 to 48 hours, preferably 1 to 24 hours.
また、重合体(C)のゲルパーミエーションクロマトグラフィ(GPC)によるポリスチレン換算重量平均分子量(以下、「Mw」という。)は、1000〜100000であることが好ましく、より好ましくは1000〜50000、更に好ましくは1000〜20000である。この重合体(C)のMwが1000未満では、解像度が劣化するおそれがある。一方、このMwが100000を超えると、現像性が低下するおそれがある。
また、重合体(C)のMwとGPCによるポリスチレン換算数平均分子量(以下、「Mn」という。)との比(Mw/Mn)は、通常1〜5、好ましくは1〜3である。
Moreover, it is preferable that the polystyrene conversion weight average molecular weight (henceforth "Mw") by the gel permeation chromatography (GPC) of a polymer (C) is 1000-100000, More preferably, it is 1000-50000, More preferably Is 1000-20000. If the Mw of the polymer (C) is less than 1000, the resolution may be deteriorated. On the other hand, if this Mw exceeds 100,000, the developability may be lowered.
Moreover, the ratio (Mw / Mn) of Mw of the polymer (C) and polystyrene-reduced number average molecular weight (hereinafter referred to as “Mn”) by GPC is usually 1 to 5, preferably 1 to 3.
本発明のネガ型感放射線性組成物において、前記重合体(C)は、1種のみ含まれていてもよいし、2種以上含まれていてもよい。 In the negative radiation-sensitive composition of the present invention, the polymer (C) may be included alone or in combination of two or more.
本発明のネガ型感放射線性組成物に含有される前記重合体(C)の含有量は、前記ポリシロキサン(A)100質量部に対して、1〜70質量部であることが好ましく、より好ましくは1〜60質量部、更に好ましくは1〜50質量部である。この含有量が、1〜70質量部である場合、効果的に誘電率を低下させ、且つ十分な現像性を維持できるため好ましい。 The content of the polymer (C) contained in the negative radiation-sensitive composition of the present invention is preferably 1 to 70 parts by mass with respect to 100 parts by mass of the polysiloxane (A). Preferably it is 1-60 mass parts, More preferably, it is 1-50 mass parts. A content of 1 to 70 parts by mass is preferable because the dielectric constant can be effectively reduced and sufficient developability can be maintained.
(1−4)溶剤(D)
前記溶剤(D)は、通常、有機溶剤であり、アルコール系溶剤、ケトン系溶剤、アミド系溶剤、エーテル系溶剤、エステル系溶剤、脂肪族炭化水素系溶剤、芳香族系溶剤、含ハロゲン溶剤等が挙げられる。
本発明のネガ型感放射線性組成物においては、前記ポリシロキサン(A)、酸発生剤(B)、重合体(C)等の成分が、この溶剤(D)に溶解又は分散されて含まれている。
(1-4) Solvent (D)
The solvent (D) is usually an organic solvent, such as an alcohol solvent, a ketone solvent, an amide solvent, an ether solvent, an ester solvent, an aliphatic hydrocarbon solvent, an aromatic solvent, a halogen-containing solvent, etc. Is mentioned.
In the negative radiation sensitive composition of the present invention, components such as the polysiloxane (A), the acid generator (B), and the polymer (C) are dissolved or dispersed in the solvent (D). ing.
前記アルコール系溶剤としては、モノアルコール系溶剤、多価アルコール系溶剤、多価アルコール部分エーテル系溶剤等が挙げられる。
前記モノアルコール系溶剤としては、例えば、メタノール、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、イソブタノール、sec−ブタノール、tert−ブタノール、n−ペンタノール、イソペンタノール、2−メチルブタノール、sec−ペンタノール、tert−ペンタノール、3−メトキシブタノール、n−ヘキサノール、2−メチルペンタノール、sec−ヘキサノール、2−エチルブタノール、sec−ヘプタノール、3−ヘプタノール、n−オクタノール、2−エチルヘキサノール、sec−オクタノール、n−ノニルアルコール、2,6−ジメチル−4−ヘプタノール、n−デカノール、sec−ウンデシルアルコール、トリメチルノニルアルコール、sec−テトラデシルアルコール、sec−ヘプタデシルアルコール、フルフリルアルコール、フェノール、シクロヘキサノール、メチルシクロヘキサノール、3,3,5−トリメチルシクロヘキサノール、ベンジルアルコール、ジアセトンアルコール等が挙げられる。
Examples of the alcohol solvent include a monoalcohol solvent, a polyhydric alcohol solvent, a polyhydric alcohol partial ether solvent, and the like.
Examples of the monoalcohol solvent include methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, tert-butanol, n-pentanol, isopentanol, 2-methylbutanol, sec. -Pentanol, tert-pentanol, 3-methoxybutanol, n-hexanol, 2-methylpentanol, sec-hexanol, 2-ethylbutanol, sec-heptanol, 3-heptanol, n-octanol, 2-ethylhexanol, sec-octanol, n-nonyl alcohol, 2,6-dimethyl-4-heptanol, n-decanol, sec-undecyl alcohol, trimethylnonyl alcohol, sec-tetradecyl alcohol, sec- Descriptor decyl alcohol, furfuryl alcohol, phenol, cyclohexanol, methyl cyclohexanol, 3,3,5-trimethyl cyclohexanol, benzyl alcohol, diacetone alcohol and the like.
前記多価アルコール系溶剤としては、例えば、エチレングリコール、1,2−プロピレングリコール、1,3−ブチレングリコール、2,4−ペンタンジオール、2−メチル−2,4−ペンタンジオール、2,5−ヘキサンジオール、2,4−ヘプタンジオール、2−エチル−1,3−ヘキサンジオール、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、トリプロピレングリコール等が挙げられる。 Examples of the polyhydric alcohol solvent include ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, 2,4-pentanediol, 2-methyl-2,4-pentanediol, 2,5- Examples include hexanediol, 2,4-heptanediol, 2-ethyl-1,3-hexanediol, diethylene glycol, dipropylene glycol, triethylene glycol, and tripropylene glycol.
前記多価アルコール部分エーテル系溶剤としては、例えば、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノヘキシルエーテル、エチレングリコールモノフェニルエーテル、エチレングリコールモノ−2−エチルブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノヘキシルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノプロピルエーテル等が挙げられる。 Examples of the polyhydric alcohol partial ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monohexyl ether, ethylene glycol monophenyl ether, ethylene glycol mono 2-ethylbutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monohexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, Propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, and the like.
前記ケトン系溶剤としては、例えば、アセトン、メチルエチルケトン、メチル−n−プロピルケトン、メチル−n−ブチルケトン、ジエチルケトン、メチルイソブチルケトン、メチル−n−ペンチルケトン、エチル−n−ブチルケトン、メチル−n−ヘキシルケトン、ジイソブチルケトン、トリメチルノナノン、シクロペンタノン、シクロヘキサノン、シクロヘプタノン、シクロオクタノン、2−ヘキサノン、メチルシクロヘキサノン、2,4−ペンタンジオン、アセトニルアセトン、ジアセトンアルコール、アセトフェノン、フェンチョン等が挙げられる。 Examples of the ketone solvent include acetone, methyl ethyl ketone, methyl-n-propyl ketone, methyl-n-butyl ketone, diethyl ketone, methyl isobutyl ketone, methyl-n-pentyl ketone, ethyl-n-butyl ketone, and methyl-n-. Hexyl ketone, diisobutyl ketone, trimethylnonanone, cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone, 2-hexanone, methylcyclohexanone, 2,4-pentanedione, acetonylacetone, diacetone alcohol, acetophenone, fenchon Etc.
前記アミド系溶剤としては、例えば、N,N−ジメチルイミダゾリジノン、N−メチルホルムアミド、N,N−ジメチルホルムアミド、N,N−ジエチルホルムアミド、アセトアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、N−メチルプロピオンアミド、N−メチルピロリドン等が挙げられる。 Examples of the amide solvent include N, N-dimethylimidazolidinone, N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide. , N-methylpropionamide, N-methylpyrrolidone and the like.
前記エーテル系溶剤としては、例えば、エチルエーテル、イソプロピルエーテル、n−ブチルエーテル、n−ヘキシルエーテル、2−エチルヘキシルエーテル、エチレンオキシド、1,2−プロピレンオキシド、ジオキソラン、4−メチルジオキソラン、ジオキサン、ジメチルジオキサン、エチレングリコールモノメチルエーテル、エチレングリコールジメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールモノ−n−ブチルエーテル、エチレングリコールモノ−n−ヘキシルエーテル、エチレングリコールモノフェニルエーテル、エチレングリコールモノ−2−エチルブチルエーテル、エチレングリコールジブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールモノ−n−ブチルエーテル、ジエチレングリコールジ−n−ブチルエーテル、ジエチレングリコールモノ−n−ヘキシルエーテル、エトキシトリグリコール、テトラエチレングリコールジ−n−ブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、トリプロピレングリコールモノメチルエーテル、テトラヒドロフラン、2−メチルテトラヒドロフラン、ジフェニルエーテル、アニソール等が挙げられる。 Examples of the ether solvent include ethyl ether, isopropyl ether, n-butyl ether, n-hexyl ether, 2-ethylhexyl ether, ethylene oxide, 1,2-propylene oxide, dioxolane, 4-methyldioxolane, dioxane, dimethyldioxane, Ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-n-hexyl ether, ethylene glycol monophenyl ether, ethylene glycol mono-2-ethyl Butyl ether, ethylene glycol dibutyl ether, diethylene glycol monomethyl ether, di Tylene glycol dimethyl ether, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, diethylene glycol mono-n-butyl ether, diethylene glycol di-n-butyl ether, diethylene glycol mono-n-hexyl ether, ethoxytriglycol, tetraethylene glycol di-n-butyl ether, propylene glycol Monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, tripropylene glycol monomethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, di Phenyl ether, anisole, and the like.
前記エステル系溶剤としては、例えば、ジエチルカーボネート、プロピレンカーボネート、酢酸メチル、酢酸エチル、γ−ブチロラクトン、γ−バレロラクトン、酢酸n−プロピル、酢酸イソプロピル、酢酸n−ブチル、酢酸イソブチル、酢酸sec−ブチル、酢酸n−ペンチル、酢酸sec−ペンチル、酢酸3−メトキシブチル、酢酸メチルペンチル、酢酸2−エチルブチル、酢酸2−エチルヘキシル、酢酸ベンジル、酢酸シクロヘキシル、酢酸メチルシクロヘキシル、酢酸n−ノニル、アセト酢酸メチル、アセト酢酸エチル、酢酸エチレングリコールモノメチルエーテル、酢酸エチレングリコールモノエチルエーテル、酢酸ジエチレングリコールモノメチルエーテル、酢酸ジエチレングリコールモノエチルエーテル、酢酸ジエチレングリコールモノ−n−ブチルエーテル、酢酸プロピレングリコールモノメチルエーテル、酢酸プロピレングリコールモノエチルエーテル、酢酸プロピレングリコールモノプロピルエーテル、酢酸プロピレングリコールモノブチルエーテル、酢酸ジプロピレングリコールモノメチルエーテル、酢酸ジプロピレングリコールモノエチルエーテル、ジ酢酸グリコール、酢酸メトキシトリグリコール、プロピオン酸エチル、プロピオン酸n−ブチル、プロピオン酸イソアミル、シュウ酸ジエチル、シュウ酸ジ−n−ブチル、乳酸メチル、乳酸エチル、乳酸n−ブチル、乳酸n−アミル、マロン酸ジエチル、フタル酸ジメチル、フタル酸ジエチル等が挙げられる。 Examples of the ester solvent include diethyl carbonate, propylene carbonate, methyl acetate, ethyl acetate, γ-butyrolactone, γ-valerolactone, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, sec-butyl acetate. N-pentyl acetate, sec-pentyl acetate, 3-methoxybutyl acetate, methyl pentyl acetate, 2-ethylbutyl acetate, 2-ethylhexyl acetate, benzyl acetate, cyclohexyl acetate, methyl cyclohexyl acetate, n-nonyl acetate, methyl acetoacetate, Ethyl acetoacetate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol acetate Mono-n-butyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether acetate, dipropylene glycol monoethyl ether acetate, glycol diacetate , Methoxytriglycol acetate, ethyl propionate, n-butyl propionate, isoamyl propionate, diethyl oxalate, di-n-butyl oxalate, methyl lactate, ethyl lactate, n-butyl lactate, n-amyl lactate, malonic acid Examples include diethyl, dimethyl phthalate, and diethyl phthalate.
前記脂肪族炭化水素系溶剤としては、例えば、n−ペンタン、イソペンタン、n−ヘキサン、イソヘキサン、n−ヘプタン、イソヘプタン、2,2,4−トリメチルペンタン、n−オクタン、イソオクタン、シクロヘキサン、メチルシクロヘキサン等が挙げられる。
前記芳香族炭化水素系溶剤としては、例えば、ベンゼン、トルエン、キシレン、エチルベンゼン、トリメチルベンゼン、メチルエチルベンゼン、n−プロピルベンセン、イソプロピルベンセン、ジエチルベンゼン、イソブチルベンゼン、トリエチルベンゼン、ジイソプロピルベンセン、n−アミルナフタレン、トリメチルベンゼン等が挙げられる。
前記含ハロゲン溶剤としては、例えば、ジクロロメタン、クロロホルム、フロン、クロロベンゼン、ジクロロベンゼン等が挙げられる。
Examples of the aliphatic hydrocarbon solvent include n-pentane, isopentane, n-hexane, isohexane, n-heptane, isoheptane, 2,2,4-trimethylpentane, n-octane, isooctane, cyclohexane, methylcyclohexane and the like. Is mentioned.
Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propyl benzene, isopropyl benzene, diethyl benzene, isobutyl benzene, triethyl benzene, diisopropyl benzene, n-amyl naphthalene, And trimethylbenzene.
Examples of the halogen-containing solvent include dichloromethane, chloroform, chlorofluorocarbon, chlorobenzene, dichlorobenzene, and the like.
これらの溶剤(D)は、種類を問わず、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。 These solvents (D) may be used singly or in combination of two or more, regardless of the type.
前記溶剤(D)としては、本発明のネガ型感放射線性組成物を用いて硬化パターンを形成する際に、塗膜をベーク(PB)した後、膜内残存溶剤量を低減させる観点から、沸点が150℃未満の有機溶剤を使用することが好ましい。特に、アルコール系溶剤、ケトン系溶剤及びエステル系溶剤のうちの1種又は2種以上を使用することが好ましい。
尚、前記溶剤(D)は、ポリシロキサン(A)の合成時に、反応溶媒として用いた有機溶剤と同じものであってもよい。また、ポリシロキサン(A)の合成が終了した後に、溶剤を所望の有機溶剤に置換することもできる。
As the solvent (D), when forming a cured pattern using the negative radiation-sensitive composition of the present invention, after baking (PB) the coating film, from the viewpoint of reducing the amount of solvent remaining in the film, It is preferable to use an organic solvent having a boiling point of less than 150 ° C. In particular, it is preferable to use one or more of alcohol solvents, ketone solvents and ester solvents.
In addition, the said solvent (D) may be the same as the organic solvent used as a reaction solvent at the time of the synthesis | combination of polysiloxane (A). Further, after the synthesis of polysiloxane (A) is completed, the solvent can be replaced with a desired organic solvent.
(1−5)添加剤
本発明のネガ型感放射線性組成物は、酸拡散制御剤、界面活性剤等の添加剤を含んでいてもよい。
前記酸拡散制御剤は、本発明のネガ型感放射線性組成物を用いて得られた乾燥被膜に対する紫外線等の露光により生じる酸のレジスト被膜中における拡散現象を制御し、未露光領域における好ましくない化学反応を抑制する作用を有する成分である。
このような酸拡散制御剤を配合することにより、レジストとしての解像度が更に向上するとともに、露光から現像までの引き置き時間(PED)の変動によるレジストパターンの線幅変化を抑えることができ、極めて優れたプロセス安定性を得ることができる。
(1-5) Additive The negative radiation-sensitive composition of the present invention may contain additives such as an acid diffusion controller and a surfactant.
The acid diffusion control agent controls the diffusion phenomenon in the resist film of the acid generated by the exposure of ultraviolet rays or the like to the dry film obtained using the negative radiation-sensitive composition of the present invention, and is not preferable in the unexposed area. It is a component having an action of suppressing a chemical reaction.
By compounding such an acid diffusion control agent, the resolution as a resist is further improved, and the change in the line width of the resist pattern due to fluctuations in the holding time (PED) from exposure to development can be suppressed. Excellent process stability can be obtained.
前記酸拡散制御剤としては、露光や加熱により塩基性が変化しない含窒素有機化合物が好ましい。
前記含窒素有機化合物としては、3級アミン化合物、アミド基含有化合物、4級アンモニウムヒドロキシド化合物、含窒素複素環化合物等が挙げられる。
The acid diffusion controller is preferably a nitrogen-containing organic compound whose basicity does not change by exposure or heating.
Examples of the nitrogen-containing organic compound include tertiary amine compounds, amide group-containing compounds, quaternary ammonium hydroxide compounds, and nitrogen-containing heterocyclic compounds.
前記3級アミン化合物としては、例えば、トリエチルアミン、トリ−n−プロピルアミン、トリ−n−ブチルアミン、トリ−n−ペンチルアミン、トリ−n−ヘキシルアミン、トリ−n−ヘプチルアミン、トリ−n−オクチルアミン、トリ−n−ノニルアミン、トリ−n−デシルアミン、シクロヘキシルジメチルアミン、ジシクロヘキシルメチルアミン、トリシクロヘキシルアミン等のトリ(シクロ)アルキルアミン類;アニリン、N−メチルアニリン、N,N−ジメチルアニリン、2−メチルアニリン、3−メチルアニリン、4−メチルアニリン、4−ニトロアニリン、2,6−ジメチルアニリン、2,6−ジイソプロピルアニリン、ジフェニルアミン、トリフェニルアミン、ナフチルアミン等の芳香族アミン類;トリエタノールアミン、ジエタノールアニリン等のアルカノールアミン類;N,N,N',N'−テトラメチルエチレンジアミン、N,N,N',N'−テトラキス(2−ヒドロキシプロピル)エチレンジアミン、1,3−ビス[1−(4−アミノフェニル)−1−メチルエチル]ベンゼンテトラメチレンジアミン、2,2−ビス(4−アミノフェニル)プロパン、2−(3−アミノフェニル)−2−(4−アミノフェニル)プロパン、2−(4−アミノフェニル)−2−(3−ヒドロキシフェニル)プロパン、2−(4−アミノフェニル)−2−(4−ヒドロキシフェニル)プロパン、1,4−ビス[1−(4−アミノフェニル)−1−メチルエチル]ベンゼン、1,3−ビス[1−(4−アミノフェニル)−1−メチルエチル]ベンゼン、ビス(2−ジメチルアミノエチル)エーテル、ビス(2−ジエチルアミノエチル)エーテル等が挙げられる。 Examples of the tertiary amine compound include triethylamine, tri-n-propylamine, tri-n-butylamine, tri-n-pentylamine, tri-n-hexylamine, tri-n-heptylamine, tri-n- Tri (cyclo) alkylamines such as octylamine, tri-n-nonylamine, tri-n-decylamine, cyclohexyldimethylamine, dicyclohexylmethylamine, tricyclohexylamine; aniline, N-methylaniline, N, N-dimethylaniline, Aromatic amines such as 2-methylaniline, 3-methylaniline, 4-methylaniline, 4-nitroaniline, 2,6-dimethylaniline, 2,6-diisopropylaniline, diphenylamine, triphenylamine, naphthylamine; triethanol Amines, Alkanolamines such as ethanolaniline; N, N, N ′, N′-tetramethylethylenediamine, N, N, N ′, N′-tetrakis (2-hydroxypropyl) ethylenediamine, 1,3-bis [1- ( 4-aminophenyl) -1-methylethyl] benzenetetramethylenediamine, 2,2-bis (4-aminophenyl) propane, 2- (3-aminophenyl) -2- (4-aminophenyl) propane, 2- (4-aminophenyl) -2- (3-hydroxyphenyl) propane, 2- (4-aminophenyl) -2- (4-hydroxyphenyl) propane, 1,4-bis [1- (4-aminophenyl) -1-methylethyl] benzene, 1,3-bis [1- (4-aminophenyl) -1-methylethyl] benzene, bis (2-dimethylamino ester) Le) ether, bis (2-diethylaminoethyl) ether.
前記アミド基含有化合物としては、例えば、N−tert−ブトキシカルボニルジ−n−オクチルアミン、N−tert−ブトキシカルボニルジ−n−ノニルアミン、N−tert−ブトキシカルボニルジ−n−デシルアミン、N−tert−ブトキシカルボニルジシクロヘキシルアミン、N−tert−ブトキシカルボニル−1−アダマンチルアミン、N−tert−ブトキシカルボニル−N−メチル−1−アダマンチルアミン、N,N−ジ−tert−ブトキシカルボニル−1−アダマンチルアミン、N,N−ジ−tert−ブトキシカルボニル−N−メチル−1−アダマンチルアミン、N−tert−ブトキシカルボニル−4,4’−ジアミノジフェニルメタン、N,N’−ジ−tert−ブトキシカルボニルヘキサメチレンジアミン、N,N,N’,N’−テトラ−tert−ブトキシカルボニルヘキサメチレンジアミン、N,N−ジ−tert−ブトキシカルボニル−1,7−ジアミノヘプタン、N,N’−ジ−tert−ブトキシカルボニル−1,8−ジアミノオクタン、N,N’−ジ−tert−ブトキシカルボニル−1,9−ジアミノノナン、N,N’−ジ−tert−ブトキシカルボニル−1,10−ジアミノデカン、N,N’−ジ−tert−ブトキシカルボニル−1,12−ジアミノドデカン、N,N’−ジ−tert−ブトキシカルボニル−4,4’−ジアミノジフェニルメタン、N−tert−ブトキシカルボニルベンズイミダゾール、N−tert−ブトキシカルボニル−2−メチルベンズイミダゾール、N−tert−ブトキシカルボニル−2−フェニルベンズイミダゾール、N−tert−ブトキシカルボニル−ピロリジン、N−tert−ブトキシカルボニル−ピペリジン、N−tert−ブトキシカルボニル−4−ヒドロキシ−ピペリジン、N−tert−ブトキシカルボニル−モルホリン等のN−tert−ブトキシカルボニル基含有アミノ化合物のほか、ホルムアミド、N−メチルホルムアミド、N,N−ジメチルホルムアミド、アセトアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、プロピオンアミド、ベンズアミド、ピロリドン、N−メチルピロリドン等が挙げられる。 Examples of the amide group-containing compound include N-tert-butoxycarbonyldi-n-octylamine, N-tert-butoxycarbonyldi-n-nonylamine, N-tert-butoxycarbonyldi-n-decylamine, and N-tert. -Butoxycarbonyldicyclohexylamine, N-tert-butoxycarbonyl-1-adamantylamine, N-tert-butoxycarbonyl-N-methyl-1-adamantylamine, N, N-di-tert-butoxycarbonyl-1-adamantylamine, N, N-di-tert-butoxycarbonyl-N-methyl-1-adamantylamine, N-tert-butoxycarbonyl-4,4′-diaminodiphenylmethane, N, N′-di-tert-butoxycarbonylhexamethylenediamine N, N, N ′, N′-tetra-tert-butoxycarbonylhexamethylenediamine, N, N-di-tert-butoxycarbonyl-1,7-diaminoheptane, N, N′-di-tert-butoxycarbonyl- 1,8-diaminooctane, N, N′-di-tert-butoxycarbonyl-1,9-diaminononane, N, N′-di-tert-butoxycarbonyl-1,10-diaminodecane, N, N′-di -Tert-butoxycarbonyl-1,12-diaminododecane, N, N'-di-tert-butoxycarbonyl-4,4'-diaminodiphenylmethane, N-tert-butoxycarbonylbenzimidazole, N-tert-butoxycarbonyl-2 -Methylbenzimidazole, N-tert-butoxycarbonyl-2-fur N-tert-butoxy such as nilbenzimidazole, N-tert-butoxycarbonyl-pyrrolidine, N-tert-butoxycarbonyl-piperidine, N-tert-butoxycarbonyl-4-hydroxy-piperidine, N-tert-butoxycarbonyl-morpholine In addition to carbonyl group-containing amino compounds, formamide, N-methylformamide, N, N-dimethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, propionamide, benzamide, pyrrolidone, N-methylpyrrolidone, etc. It is done.
前記4級アンモニウムヒドロキシド化合物としては、例えば、テトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド、テトラ−n−プロピルアンモニウムヒドロキシド、テトラ−n−ブチルアンモニウムヒドロキシド等が挙げられる。 Examples of the quaternary ammonium hydroxide compound include tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetra-n-propylammonium hydroxide, tetra-n-butylammonium hydroxide, and the like.
前記含窒素複素環化合物としては、例えば、イミダゾール、4−メチルイミダゾール、1−ベンジル−2−メチルイミダゾール、4−メチル−2−フェニルイミダゾール、ベンズイミダゾール、2−フェニルベンズイミダゾール等のイミダゾール類;ピリジン、2−メチルピリジン、4−メチルピリジン、2−エチルピリジン、4−エチルピリジン、2−フェニルピリジン、4−フェニルピリジン、2−メチル−4−フェニルピリジン、ニコチン、ニコチン酸、ニコチン酸アミド、キノリン、4−ヒドロキシキノリン、8−オキシキノリン、アクリジン等のピリジン類;ピペラジン、1−(2−ヒドロキシエチル)ピペラジン等のピペラジン類のほか、ピラジン、ピラゾール、ピリダジン、キノザリン、プリン、ピロリジン、ピペリジン、3−ピペリジノ−1,2−プロパンジオール、モルホリン、4−メチルモルホリン、1,4−ジメチルピペラジン、1,4−ジアザビシクロ[2.2.2]オクタン等が挙げられる。 Examples of the nitrogen-containing heterocyclic compound include imidazoles such as imidazole, 4-methylimidazole, 1-benzyl-2-methylimidazole, 4-methyl-2-phenylimidazole, benzimidazole, and 2-phenylbenzimidazole; 2-methylpyridine, 4-methylpyridine, 2-ethylpyridine, 4-ethylpyridine, 2-phenylpyridine, 4-phenylpyridine, 2-methyl-4-phenylpyridine, nicotine, nicotinic acid, nicotinamide, quinoline Pyridines such as 4-hydroxyquinoline, 8-oxyquinoline, acridine; piperazines such as piperazine and 1- (2-hydroxyethyl) piperazine, pyrazine, pyrazole, pyridazine, quinosaline, purine, pyrrolidine, piperidine, 3 Piperidino-1,2-propanediol, morpholine, 4-methylmorpholine, 1,4-dimethylpiperazine, 1,4-diazabicyclo [2.2.2] octane.
これらの酸拡散制御剤は、種類を問わず、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。 These acid diffusion control agents may be used alone or in combination of two or more, regardless of the type.
前記酸拡散制御剤としては、その含有効果が優れることから、3級アミン化合物、アミド基含有化合物及び含窒素複素環化合物が好ましい。これらのうち、アミド基含有化合物としては、N−tert−ブトキシカルボニル基含有アミノ化合物が好ましく、含窒素複素環化合物としては、イミダゾール類が好ましい。 As the acid diffusion controller, a tertiary amine compound, an amide group-containing compound and a nitrogen-containing heterocyclic compound are preferable because of its excellent content effect. Of these, the amide group-containing compound is preferably an N-tert-butoxycarbonyl group-containing amino compound, and the nitrogen-containing heterocyclic compound is preferably an imidazole.
本発明のネガ型感放射線性組成物が、酸拡散制御剤を含む場合、酸拡散制御剤の含有量は、前記ポリシロキサン(A)100質量部に対して、通常、15質量部以下、好ましくは10質量部以下、更に好ましくは5質量部以下である。この含有量が15質量部を超えると、レジストとしての感度及び露光部の現像性が低下する場合がある。一方、この含有量が0.001質量部未満であると、プロセス条件によっては、レジストとしてのパターン形状や寸法の忠実度が低下する場合がある。 When the negative radiation sensitive composition of the present invention contains an acid diffusion control agent, the content of the acid diffusion control agent is usually 15 parts by mass or less, preferably 100 parts by mass of the polysiloxane (A). Is 10 parts by mass or less, more preferably 5 parts by mass or less. When this content exceeds 15 parts by mass, the sensitivity as a resist and the developability of the exposed part may be deteriorated. On the other hand, if the content is less than 0.001 part by mass, the fidelity of the pattern shape and dimensions as a resist may be lowered depending on the process conditions.
前記界面活性剤は、本発明のネガ型感放射線性組成物の塗布性、ストリエーション、露光後の現像性等を改良する作用を有する成分である。
この界面活性剤としては、ノニオン系界面活性剤、アニオン系界面活性剤、カチオン系界面活性剤、両性界面活性剤、シリコーン系界面活性剤、ポリアルキレンオキシド系界面活性剤、フッ素系界面活性剤、ポリ(メタ)アクリレート系界面活性剤等が挙げられる。
The said surfactant is a component which has the effect | action which improves the applicability | paintability of the negative radiation sensitive composition of this invention, striation, the developability after exposure, etc.
As this surfactant, nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, silicone surfactants, polyalkylene oxide surfactants, fluorine surfactants, Examples include poly (meth) acrylate surfactants.
前記ノニオン系界面活性剤としては、例えば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンn−オクチルフェニルエーテル、ポリオキシエチレンn−ノニルフェニルエーテル、ポリエチレングリコールジラウレート、ポリエチレングリコールジステアレート等が挙げられる。
また、市販品としては、以下、商品名で、「SH8400 FLUID」(Toray Dow Corning Silicone Co.製)、「KP341」(信越化学工業(株)製)、「ポリフローNo.75」、「ポリフローNo.95」(以上、共栄社化学(株)製)、「エフトップEF301」、「エフトップEF303」、「エフトップEF352」(以上、トーケムプロダクツ(株)製)、「メガファックスF171」、「メガファックスF173」(以上、大日本インキ化学工業(株)製)、「フロラードFC430」、「フロラードFC431」(以上、住友スリーエム(株)製)、「アサヒガードAG710」、「サーフロンS−382」、「サーフロンSC−101」、「サーフロンSC−102」、「サーフロンSC−103」、「サーフロンSC−104」、「サーフロンSC−105」、「サーフロンSC−106」(以上、旭硝子(株)製)等が挙げられる。
Examples of the nonionic surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene n-octylphenyl ether, polyoxyethylene n-nonylphenyl ether, polyethylene glycol dilaurate. And polyethylene glycol distearate.
In addition, as commercial products, “SH8400 FLUID” (manufactured by Toray Dow Corning Silicon Co.), “KP341” (manufactured by Shin-Etsu Chemical Co., Ltd.), “Polyflow No. 75”, “Polyflow No.” .95 ”(above, manufactured by Kyoeisha Chemical Co., Ltd.),“ F-top EF301 ”,“ F-top EF303 ”,“ F-top EF352 ”(above, manufactured by Tochem Products Co., Ltd.),“ Megafax F171 ”,“ "Megafax F173" (manufactured by Dainippon Ink and Chemicals, Inc.), "Florard FC430", "Florard FC431" (manufactured by Sumitomo 3M), "Asahi Guard AG710", "Surflon S-382""SurflonSC-101","SurflonSC-102","SurflonSC" 103 "," Surflon SC-104 "," Surflon SC-105 "," Surflon SC-106 "(manufactured by Asahi Glass Co., Ltd.).
これらの界面活性剤のなかでも、フッ素系界面活性剤及びシリコーン系界面活性剤が好ましい。
尚、これらの界面活性剤は、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
Of these surfactants, fluorine-based surfactants and silicone-based surfactants are preferable.
In addition, these surfactants may be used individually by 1 type, and may be used in combination of 2 or more type.
また、本発明のネガ型感放射線性組成物が、界面活性剤を含む場合、界面活性剤の含有量は、前記ポリシロキサン(A)100質量部に対して、通常、0.00001〜1質量部である。 Moreover, when the negative radiation sensitive composition of this invention contains surfactant, content of surfactant is 0.00001-1 mass normally with respect to 100 mass parts of said polysiloxane (A). Part.
(1−6)ネガ型感放射線性組成物の製造方法
本発明のネガ型放射線性組成物は、前記ポリシロキサン(A)と、前記酸発生剤(B)と、前記重合体(C)と、前記溶剤(D)と、必要に応じて用いられる前記添加剤とを、公知の方法で混合することにより得ることができる。
また、本発明のネガ型放射線性組成物の固形分濃度(溶剤(D)を除く全成分の濃度)は、目的、用途等に応じて、適宜、選択されるが、例えば、1〜50質量%とすることができ、好ましくは10〜40質量%である。固形分濃度が1〜50質量%である場合には、後述する硬化パターンの形成に好適な塗膜の膜厚を得ることができる。
(1-6) Production Method of Negative Radiation Sensitive Composition The negative radiation sensitive composition of the present invention comprises the polysiloxane (A), the acid generator (B), and the polymer (C). The solvent (D) can be obtained by mixing the additive used as necessary by a known method.
Moreover, although the solid content concentration (concentration of all components except the solvent (D)) of the negative radiation composition of the present invention is appropriately selected according to the purpose, use, etc., for example, 1 to 50 masses. %, Preferably 10 to 40% by mass. When the solid content concentration is 1 to 50% by mass, a film thickness of a coating film suitable for forming a cured pattern described later can be obtained.
[2]硬化パターン及びその形成方法
本発明の硬化パターン形成方法には、トレンチやホール等の一つの形状のみからなる硬化パターンを形成するための方法(以下、「パターン形成方法(I)」ともいう)と、トレンチとホールの両形状を有するデュアルダマシン構造を有する硬化パターンを形成するための方法(以下、「パターン形成方法(II)ともいう」がある。
[2] Cured pattern and formation method thereof The cured pattern forming method of the present invention includes a method for forming a cured pattern consisting of only one shape such as a trench or a hole (hereinafter referred to as “pattern forming method (I)”). And a method for forming a cured pattern having a dual damascene structure having both trench and hole shapes (hereinafter also referred to as “pattern formation method (II)”).
(2−1)パターン形成方法(I)
本発明のパターン形成方法(I)は、前記本発明のネガ型感放射線性組成物を基板に塗布し、塗膜を形成する工程(i)と、前記工程(i)により得られた塗膜をベークする工程(ii)と、前記工程(ii)により得られた膜を露光する工程(iii)と、前記工程(iii)により得られた、露光された膜をベークする工程(iv)と、前記工程(iv)により得られた膜を現像液で現像し、ネガ型パターンを形成する工程(v)と、前記工程(v)により得られたネガ型パターンに、高エネルギー線照射及び加熱のうちの少なくとも一方の硬化処理を施し、硬化パターンを形成する工程(vi)と、を備える。
(2-1) Pattern formation method (I)
The pattern forming method (I) of the present invention comprises a step (i) of applying the negative radiation-sensitive composition of the present invention to a substrate to form a coating film, and a coating film obtained by the step (i). A step (ii), a step (iii) of exposing the film obtained by the step (ii), and a step (iv) of baking the exposed film obtained by the step (iii). The film obtained in the step (iv) is developed with a developer to form a negative pattern, and the negative pattern obtained in the step (v) is irradiated with high energy rays and heated. (Vi) which performs the hardening process of at least one of these, and forms a hardening pattern.
前記工程(i)において、ネガ型感放射線性組成物が基板に塗布されて、塗膜が形成される。
前記組成物の塗布方法としては、回転塗布法、流延塗布法、ロール塗布法等が挙げられる。塗布条件は、所望の膜厚となるよう、塗布方法、組成物の固形分濃度、粘度等を考慮の上、選択される。
前記基板としては、Si、SiO2、SiN、SiC、SiCN等のSi含有層で被覆されたウエハ等が挙げられる。尚、ネガ型感放射線性組成物の潜在能力を最大限に引き出すため、特公平6−12452号公報(特開昭59−93448号公報)等に開示されているように、使用される基板上に有機系あるいは無機系の反射防止膜を形成しておくこともできる。
In said process (i), a negative radiation sensitive composition is apply | coated to a board | substrate, and a coating film is formed.
Examples of the method for applying the composition include a spin coating method, a cast coating method, and a roll coating method. The coating conditions are selected in consideration of the coating method, the solid content concentration of the composition, the viscosity and the like so as to obtain a desired film thickness.
Examples of the substrate include a wafer coated with a Si-containing layer such as Si, SiO 2 , SiN, SiC, or SiCN. In order to maximize the potential of the negative radiation sensitive composition, as disclosed in Japanese Patent Publication No. 6-12452 (Japanese Patent Laid-Open No. 59-93448), etc. It is also possible to form an organic or inorganic antireflection film.
前記工程(ii)は、塗膜をベーク(以下、「PB」という。)する工程であり、この工程により、塗膜中の溶剤を揮発させる。
このPBの加熱条件は、組成物の組成によって、適宜、選択されるが、好ましくは60℃〜150℃であり、より好ましくは70℃〜120℃である。
The step (ii) is a step of baking the coating film (hereinafter referred to as “PB”), and the solvent in the coating film is volatilized by this step.
The PB heating condition is appropriately selected depending on the composition of the composition, but is preferably 60 ° C to 150 ° C, more preferably 70 ° C to 120 ° C.
前記工程(iii)は、前記工程(ii)により得られた膜(乾燥被膜)を露光する工程である。この工程においては、通常、所望のパターンを形成するためのマスクパターンを有するフォトマスクを介して、下記に例示する放射線が、前記膜(乾燥被膜)の表面に照射、即ち、露光される。これにより、放射線は、フォトマスクの開口部を通過し、更に露光用のレンズを通過して、膜(乾燥被膜)に達する。膜(乾燥被膜)における露光部は、工程(v)により除去される。 The step (iii) is a step of exposing the film (dry film) obtained by the step (ii). In this step, the surface of the film (dried film) is usually irradiated, that is, exposed to the radiation illustrated below through a photomask having a mask pattern for forming a desired pattern. As a result, the radiation passes through the opening of the photomask, further passes through the exposure lens, and reaches the film (dry coating). The exposed portion of the film (dry film) is removed by step (v).
前記工程(iii)における露光条件は、膜(乾燥被膜)の組成(添加剤の種類等)、厚さ等により、適宜、選択される。また、この露光に使用される放射線としては、可視光線、紫外線、遠紫外線、X線、電子線等の荷電粒子線等が挙げられ、これらのうち、ArFエキシマレーザー(波長193nm)、KrFエキシマレーザー(波長248nm)で代表される遠紫外線及び電子線が好ましい。 The exposure conditions in the step (iii) are appropriately selected depending on the composition (type of additive, etc.), thickness, etc. of the film (dry film). Examples of radiation used for this exposure include visible light rays, ultraviolet rays, far ultraviolet rays, X-rays, and charged particle beams such as electron beams. Among these, ArF excimer laser (wavelength 193 nm), KrF excimer laser, etc. Far ultraviolet rays and electron beams represented by (wavelength 248 nm) are preferable.
前記工程(iv)は、露光された膜をベーク(以下、「PEB」という。)する工程であり、この工程により、露光部に含まれる重合体の架橋反応が円滑に進めることができる。
このPEBの加熱条件は、組成物の組成によって、適宜、選択されるが、架橋反応の円滑化の観点から、好ましくは30℃〜200℃であり、より好ましくは50℃〜170℃である。
The step (iv) is a step of baking the exposed film (hereinafter referred to as “PEB”). By this step, the crosslinking reaction of the polymer contained in the exposed portion can be smoothly advanced.
The heating conditions for PEB are appropriately selected depending on the composition of the composition, but are preferably 30 ° C. to 200 ° C., more preferably 50 ° C. to 170 ° C., from the viewpoint of facilitating the crosslinking reaction.
前記工程(v)は、前記工程(iv)により得られた膜を現像液で現像し、ネガ型パターンを形成する工程であり、この工程により、前記工程(iii)における未露光部が除去され、露光部、即ち、前記フォトマスクの開口部のパターンを反映したネガ型パターンを残存、形成させる。 The step (v) is a step of developing the film obtained in the step (iv) with a developer to form a negative pattern, and this step removes the unexposed portion in the step (iii). The negative pattern reflecting the pattern of the exposed portion, that is, the opening of the photomask is left and formed.
前記現像液としては、通常、アルカリ性化合物を水に溶解させてなるアルカリ性水溶液が用いられる。
このアルカリ性化合物としては、例えば、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、けい酸ナトリウム、メタけい酸ナトリウム、アンモニア、エチルアミン、n−プロピルアミン、ジエチルアミン、ジ−n−プロピルアミン、トリエチルアミン、メチルジエチルアミン、エチルジメチルアミン、トリエタノールアミン、テトラメチルアンモニウムヒドロキシド、ピロール、ピペリジン、コリン、1,8−ジアザビシクロ−[5.4.0]−7−ウンデセン、1,5−ジアザビシクロ−[4.3.0]−5−ノネン等が挙げられる。これらの化合物のなかでも、テトラメチルアンモニウムヒドロキシドが特に好ましい。
尚、これらは、1種単独で用いてよいし、2種以上を組み合わせて用いてもよい。
As the developer, an alkaline aqueous solution obtained by dissolving an alkaline compound in water is usually used.
Examples of the alkaline compound include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia, ethylamine, n-propylamine, diethylamine, di-n-propylamine, triethylamine, methyldiethylamine. , Ethyldimethylamine, triethanolamine, tetramethylammonium hydroxide, pyrrole, piperidine, choline, 1,8-diazabicyclo- [5.4.0] -7-undecene, 1,5-diazabicyclo- [4.3. 0] -5-nonene and the like. Of these compounds, tetramethylammonium hydroxide is particularly preferable.
In addition, these may be used individually by 1 type and may be used in combination of 2 or more type.
前記アルカリ性化合物の濃度は、通常、10質量%以下である。この濃度が高すぎると、露光部も現像液に溶解する場合がある。 The concentration of the alkaline compound is usually 10% by mass or less. If this concentration is too high, the exposed area may also be dissolved in the developer.
また、前記現像液は、前記アルカリ性化合物のみを含む溶液であってよいし、有機溶剤、界面活性剤等を含む組成物であってもよい。
前記有機溶剤としては、例えば、アセトン、メチルエチルケトン、メチルイソブチルケトン、アセトニルアセトン、シクロペンタノン、シクロヘキサノン、3−メチルシクロペンタノン、2,6−ジメチルシクロヘキサノン等のケトン類;メチルアルコール、エチルアルコール、n−プロピルアルコール、イソプロピルアルコール、n−ブチルアルコール、tert−ブチルアルコール、シクロペンタノール、シクロヘキサノール、1,4−ヘキサンジオール、1,4−ヘキサンジメチロール等のアルコール類;テトラヒドロフラン、ジオキサン等のエーテル類;酢酸エチル、酢酸n−ブチル、酢酸イソアミル等のエステル類;トルエン、キシレン等の芳香族炭化水素類;フェノール、ジメチルホルムアミド等が挙げられる。これらの有機溶剤は、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
Further, the developer may be a solution containing only the alkaline compound or a composition containing an organic solvent, a surfactant and the like.
Examples of the organic solvent include ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetonyl acetone, cyclopentanone, cyclohexanone, 3-methylcyclopentanone, and 2,6-dimethylcyclohexanone; methyl alcohol, ethyl alcohol, alcohols such as n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, tert-butyl alcohol, cyclopentanol, cyclohexanol, 1,4-hexanediol, 1,4-hexanedimethylol; ethers such as tetrahydrofuran and dioxane And the like; esters such as ethyl acetate, n-butyl acetate and isoamyl acetate; aromatic hydrocarbons such as toluene and xylene; and phenol and dimethylformamide. These organic solvents may be used individually by 1 type, and may be used in combination of 2 or more type.
前記現像液が有機溶剤を含む場合、その含有量は、アルカリ性水溶液100体積部に対して、100体積部以下であることが好ましい。この有機溶剤の含有量が多すぎる場合、現像性が低下して、前記工程(iii)における未露光部の現像残りが多くなる場合がある。 When the developer contains an organic solvent, the content is preferably 100 parts by volume or less with respect to 100 parts by volume of the alkaline aqueous solution. When there is too much content of this organic solvent, developability may fall and the image development residue of the unexposed part in the said process (iii) may increase.
前記工程(v)において、前記現像液で現像した後、通常、水洗及び乾燥が行われる。 In the step (v), after developing with the developer, washing and drying are usually performed.
次に、前記工程(vi)は、前記工程(v)により得られたネガ型パターンに、高エネルギー線照射及び加熱のうちの少なくとも一方の硬化処理を施し、硬化パターンを形成する工程である。
前記工程(vi)において、高エネルギー線照射により硬化処理を行う場合、電子線や紫外線等が用いられる。
Next, the step (vi) is a step of forming a cured pattern by subjecting the negative pattern obtained in the step (v) to at least one of high energy ray irradiation and heating.
In the step (vi), when a curing process is performed by high energy ray irradiation, an electron beam, ultraviolet rays, or the like is used.
また、加熱により硬化処理を行う場合、ホットプレート、オーブン、ファーネス等を使用することができる。この加熱条件は、特に限定されないが、雰囲気は、不活性ガス又は真空中であることが好ましい。また、加熱温度は、80〜450℃であることが好ましく、より好ましくは300〜450℃である。尚、前記ネガ型パターンの硬化速度を制御するため、必要に応じて、段階的加熱を適用したり、窒素ガス、空気、酸素ガス、減圧等の雰囲気を選択したりすることができる。 Moreover, when performing a hardening process by heating, a hotplate, oven, a furnace, etc. can be used. The heating conditions are not particularly limited, but the atmosphere is preferably an inert gas or vacuum. Moreover, it is preferable that heating temperature is 80-450 degreeC, More preferably, it is 300-450 degreeC. In order to control the curing rate of the negative pattern, stepwise heating can be applied, or an atmosphere such as nitrogen gas, air, oxygen gas, or reduced pressure can be selected as necessary.
このような硬化処理により、硬化皮膜において、配向分極の大きい置換基や分子が低減され、また、膜中のポアの割合が増加するため、膜の比誘電率を低下させることができる。 By such a curing treatment, substituents and molecules having large orientation polarization are reduced in the cured film, and the ratio of pores in the film increases, so that the relative dielectric constant of the film can be lowered.
(2−2)パターン形成方法(II)
本発明のパターン形成方法(II)は、(II−1)本発明のネガ型感放射線性組成物を基板に塗布、露光、現像し、ネガ型ホールパターンを有するネガ型ホールパターン基板を形成する工程[以下、「工程(II−1)」ともいう。]と、(II−2)得られたネガ型ホールパターン基板上に、本発明のネガ型感放射線性組成物を塗布、露光、現像し、ネガ型ホールパターン基板上にネガ型トレンチパターンを形成し、ネガ型デュアルダマシンパターン基板を形成する工程[以下、「工程(II−2)」ともいう。]と、(II−3)得られたネガ型デュアルダマシンパターン基板に、高エネルギー線照射及び加熱のうちの少なくとも1種の処理を施し、デュアルダマシン構造を有する硬化パターンを形成する工程[以下、「工程(II−3)」ともいう。]と、を備える。
(2-2) Pattern formation method (II)
In the pattern forming method (II) of the present invention, (II-1) the negative radiation sensitive composition of the present invention is applied to a substrate, exposed and developed to form a negative hole pattern substrate having a negative hole pattern. Step [hereinafter also referred to as “Step (II-1)”. (II-2) The negative-type radiation sensitive composition of the present invention is applied, exposed and developed on the obtained negative-type hole pattern substrate to form a negative-type trench pattern on the negative-type hole pattern substrate. And a step of forming a negative dual damascene pattern substrate [hereinafter also referred to as “step (II-2)”. And (II-3) a step of forming a cured pattern having a dual damascene structure by subjecting the obtained negative dual damascene pattern substrate to at least one of high energy ray irradiation and heating. Also referred to as “Step (II-3)”. ].
前記工程(II−1)は、前記パターン形成方法(I)に記載の、工程(i)〜(iv)と同様の工程を適宜行うことで、ネガ型ホールパターンを有するネガ型ホールパターン基板を形成する工程である(図2の(a)参照)。
ここで得られるネガ型ホールパターンの好ましい膜厚は、通常、30nm〜1000nmである。
In the step (II-1), a negative hole pattern substrate having a negative hole pattern is obtained by appropriately performing the same steps as the steps (i) to (iv) described in the pattern forming method (I). This is a process of forming (see FIG. 2A).
The preferable film thickness of the negative hole pattern obtained here is usually 30 nm to 1000 nm.
前記工程(II−2)では、まず、前記工程(II−1)で形成したネガ型ホールパターン基板上にネガ型感放射線性組成物塗布し、ネガ型ホールパターン基板上にネガ型感放射線性組成物由来の被膜を形成する(図2の(b)参照)。ここで、ネガ型感放射線性組成物を塗布する方法としては、前記硬化パターンの形成方法(1)における工程(i)に記載のものと同様の方法を用いることができる。
また、ネガ型感放射線性組成物由来の被膜を形成するために、前記硬化パターンの形成方法(1)における工程(ii)と同様に、被膜をベーク処理してもよい。
ここで得られるネガ型感放射線性組成物由来の被膜の好ましい膜厚(図2の工程(b)におけるx)は、通常、30nm〜1000nmである。
引き続き、ネガ型感放射線性組成物由来の被膜を、前記硬化パターンの形成方法(1)における工程(iii)及び工程(iv)と同様の処理を行い、ネガ型ホールパターン基板上にネガ型トレンチパターンを形成し、ネガ型デュアルダマシンパターン基板が形成される。
In the step (II-2), first, a negative radiation sensitive composition is applied on the negative hole pattern substrate formed in the step (II-1), and the negative radiation sensitivity is applied on the negative hole pattern substrate. A film derived from the composition is formed (see FIG. 2B). Here, as a method of applying the negative radiation sensitive composition, the same method as described in the step (i) in the method (1) of forming the cured pattern can be used.
Moreover, in order to form the film derived from a negative radiation sensitive composition, you may bake a film similarly to the process (ii) in the formation method (1) of the said hardening pattern.
The preferable film thickness (x in step (b) of FIG. 2) of the film derived from the negative radiation-sensitive composition obtained here is usually 30 nm to 1000 nm.
Subsequently, the film derived from the negative radiation sensitive composition is treated in the same manner as in steps (iii) and (iv) in the cured pattern forming method (1), and a negative trench is formed on the negative hole pattern substrate. A pattern is formed, and a negative dual damascene pattern substrate is formed.
前記工程(II−3)では、前記工程(II−2)で得られたネガ型デュアルダマシンパターン基板を、前記硬化パターンの形成方法(1)における工程(v)に記載と同様の処理を行い、デュアルダマシン構造を有する硬化パターンが形成される。 In the step (II-3), the negative dual damascene pattern substrate obtained in the step (II-2) is treated in the same manner as described in the step (v) in the cured pattern forming method (1). A cured pattern having a dual damascene structure is formed.
(2−3)硬化パターン
前記本発明のパターン形成方法(I)及び(II)によって得られた硬化パターンの比誘電率は、1.5〜3.0であることが好ましく、より好ましくは1.5〜2.7である。
前記比誘電率が前記範囲内であることで、本発明の硬化パターンは、LSI、システムLSI、DRAM、SDRAM、RDRAM、D−RDRAM等の半導体素子を構成する各種膜部、例えば、層間絶縁膜として好適に用いることができる。特に、銅ダマシンプロセスを含む半導体素子を構成する層間絶縁膜に有用である。
(2-3) Cured Pattern The relative dielectric constant of the cured pattern obtained by the pattern forming methods (I) and (II) of the present invention is preferably 1.5 to 3.0, more preferably 1. .5 to 2.7.
When the relative dielectric constant is within the above range, the cured pattern of the present invention can be used for various film portions constituting semiconductor elements such as LSI, system LSI, DRAM, SDRAM, RDRAM, and D-RDRAM, for example, interlayer insulating films. Can be suitably used. In particular, it is useful for an interlayer insulating film constituting a semiconductor element including a copper damascene process.
以下、実施例を挙げて、本発明の実施の形態を更に具体的に説明する。但し、本発明は、これらの実施例に何ら制約されるものではない。ここで、「部」及び「%」は、特記しない限り質量基準である。 Hereinafter, the embodiment of the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples. Here, “part” and “%” are based on mass unless otherwise specified.
[1]ポリシロキサン[ポリシロキサン溶液]の製造
下記合成例(合成例1〜4)に示すように、樹脂溶液No.1〜4の各ポリシロキサン溶液を調製した。
尚、各合成例で得られるポリシロキサンの重量平均分子量(Mw)の測定は、下記の方法により行った。
[1] Production of polysiloxane [polysiloxane solution] As shown in the following synthesis examples (synthesis examples 1 to 4), resin solution No. 1-4 polysiloxane solutions were prepared.
In addition, the measurement of the weight average molecular weight (Mw) of the polysiloxane obtained by each synthesis example was performed by the following method.
(Mwの測定)
ポリシロキサンの重量平均分子量(Mw)は、下記条件によるサイズ排除クロマトグラフィー(SEC)法により測定した。
<SEC測定条件>
測定試料は、濃度10mmol/LのLiBr−H3PO4の2−メトキシエタノール溶液を溶媒として使用し、ポリシロキサン0.1gを100ccの10mmol/L LiBr−H3PO4の2−メトキシエタノール溶液に溶解させたものを用いた。
標準試料:ポリスチレン(WAKO社製)
装置:高速GPC装置「HLC−8120GPC」(型式名)、東ソー社製
カラム:長さ15cmの水系・極性有機溶媒系GPCカラム「TSK−GEL SUPER AWM−H」(東ソー社製)を直列に3本連結して使用
測定温度:40℃
流速:0.6ml/min.
検出器:RI(前記高速GPC装置に内蔵)
(Measurement of Mw)
The weight average molecular weight (Mw) of the polysiloxane was measured by a size exclusion chromatography (SEC) method under the following conditions.
<SEC measurement conditions>
As a measurement sample, a 2-methoxyethanol solution of LiBr—H 3 PO 4 having a concentration of 10 mmol / L was used as a solvent, and 0.1 g of polysiloxane was added to 100 cc of 10 mmol / L LiBr—H 3 PO 4 in a 2-methoxyethanol solution. What was dissolved in was used.
Standard sample: Polystyrene (manufactured by WAKO)
Equipment: High-speed GPC equipment “HLC-8120GPC” (model name), manufactured by Tosoh Corporation Column: 15 cm long aqueous / polar organic solvent-based GPC column “TSK-GEL SUPER AWM-H” (made by Tosoh Corporation) 3 in series Used in conjunction with this measurement temperature: 40 ° C
Flow rate: 0.6 ml / min.
Detector: RI (built in the high-speed GPC device)
(合成例1)樹脂溶液No.1
窒素置換された石英製三口フラスコ内に、20%マレイン酸水溶液2.14g及び超純水139.6gを加えて65℃に加熱した。次いで、テトラメトキシシラン25.7g(0.169モル)、メチルトリメトキシシラン206.7g(1.52モル)、及びエトキシプロパノール25.9gを混合した溶液を1時間かけて反応容器に滴下し、65℃で4時間撹拌させた。この反応液を室温まで戻し、固形分濃度が25%となるまで減圧下で濃縮し、ケイ素含有樹脂溶液(樹脂溶液No.1)430gを得た。この樹脂溶液中における樹脂をケイ素含有樹脂(A−1)とする(構成単位は下式(A−1)参照)。
尚、前記ケイ素含有樹脂(A−1)の構成モノマー比(a:b)は10:90(mol%)であり、Mwは8300であった。
(Synthesis Example 1) Resin Solution No. 1
Into a nitrogen-substituted quartz three-necked flask, 2.14 g of a 20% maleic acid aqueous solution and 139.6 g of ultrapure water were added and heated to 65 ° C. Next, a solution obtained by mixing 25.7 g (0.169 mol) of tetramethoxysilane, 206.7 g (1.52 mol) of methyltrimethoxysilane, and 25.9 g of ethoxypropanol was dropped into the reaction vessel over 1 hour. Stir at 65 ° C. for 4 hours. This reaction liquid was returned to room temperature and concentrated under reduced pressure until the solid content concentration became 25% to obtain 430 g of a silicon-containing resin solution (resin solution No. 1). The resin in this resin solution is defined as a silicon-containing resin (A-1) (refer to the following formula (A-1) for the structural unit).
The constituent monomer ratio (a: b) of the silicon-containing resin (A-1) was 10:90 (mol%), and Mw was 8300.
(合成例2)樹脂溶液No.2
窒素置換された石英製三口フラスコ内に、20%マレイン酸水溶液1.20g及び超純水57.01gを加えて75℃に加熱した。次いで、テトラメトキシシラン14.4g(0.0946モル)、メチルトリメトキシシラン102.8g(0.755モル)、エチルトリメトキシシラン14.2g(0.0946モル)、及びエトキシプロパノール10.4gを混合した溶液を1時間かけて反応容器に滴下し、75℃で2時間撹拌させた。この反応液を室温まで戻し、固形分濃度が25%となるまで減圧下で濃縮し、ケイ素含有樹脂溶液(樹脂溶液No.2)250gを得た。この樹脂溶液中における樹脂をケイ素含有樹脂(A−2)とする(構成単位は下式(A−2)参照)。
尚、前記ケイ素含有樹脂(A−2)の構成モノマー比(a:b:c)は10:80:10(mol%)であり、Mwは8600であった。
(Synthesis Example 2) Resin Solution No. 2
Into a nitrogen-substituted quartz three-necked flask, 1.20 g of a 20% maleic acid aqueous solution and 57.01 g of ultrapure water were added and heated to 75 ° C. Next, 14.4 g (0.0946 mol) of tetramethoxysilane, 102.8 g (0.755 mol) of methyltrimethoxysilane, 14.2 g (0.0946 mol) of ethyltrimethoxysilane, and 10.4 g of ethoxypropanol were added. The mixed solution was dropped into the reaction vessel over 1 hour and stirred at 75 ° C. for 2 hours. This reaction liquid was returned to room temperature and concentrated under reduced pressure until the solid content concentration became 25% to obtain 250 g of a silicon-containing resin solution (resin solution No. 2). The resin in this resin solution is referred to as silicon-containing resin (A-2) (refer to the following formula (A-2) for the structural unit).
The constituent monomer ratio (a: b: c) of the silicon-containing resin (A-2) was 10:80:10 (mol%), and Mw was 8,600.
(合成例3)樹脂溶液No.3
窒素置換された石英製セパラブルフラスコ内に、メチルトリメトキシシラン81.6g(0.60モル)、ビス(トリエトキシシリル)エタン53.1g(0.15モル)、及びプロピレングリコールモノエチルエーテル92.3gを加え、この反応液を水浴で65℃に加熱した後に、20%マレイン酸水溶液1.1g及び超純水72.0gを加えて65℃で2時間撹拌させた。この反応液を室温まで戻し、固形分濃度が30%となるまで減圧下で濃縮し、ケイ素含有樹脂溶液(樹脂溶液No.3)200gを得た。この樹脂溶液中における樹脂をケイ素含有樹脂(A−3)とする(構成単位は下式(A−3)参照)。
尚、前記ケイ素含有樹脂(A−3)の構成モノマー比a:bは、80:20(mol%)であり、Mwは4200であった。
(Synthesis Example 3) Resin Solution No. 3
In a nitrogen-substituted quartz separable flask, 81.6 g (0.60 mol) of methyltrimethoxysilane, 53.1 g (0.15 mol) of bis (triethoxysilyl) ethane, and propylene glycol monoethyl ether 92 After adding 0.3 g and heating the reaction solution to 65 ° C. in a water bath, 1.1 g of a 20% maleic acid aqueous solution and 72.0 g of ultrapure water were added and stirred at 65 ° C. for 2 hours. This reaction liquid was returned to room temperature and concentrated under reduced pressure until the solid content concentration became 30%, to obtain 200 g of a silicon-containing resin solution (resin solution No. 3). The resin in this resin solution is referred to as silicon-containing resin (A-3) (refer to the following formula (A-3) for the structural unit).
The constituent monomer ratio a: b of the silicon-containing resin (A-3) was 80:20 (mol%), and Mw was 4200.
(合成例4)樹脂溶液No.4
窒素置換された石英製三口フラスコ内に、20%マレイン酸水溶液1.1g及び超純水69.0gを加えて65℃に加熱した。次いで、テトラメトキシシラン24.6g(0.16モル)、メチルトリメトキシシラン55.0g(0.40モル)、ビニルトリメトキシシラン35.9g(0.24モル)及びプロピレングリコールモノエチルエーテル14.4gを混合した溶液を1時間かけて反応容器に滴下し、65℃で2時間撹拌させた。この反応液を室温まで戻し、固形分濃度が30%となるまで減圧下で濃縮し、ケイ素含有樹脂溶液(樹脂溶液No.4)187gを得た。この樹脂溶液中における樹脂をケイ素含有樹脂(A−4)とする(構成単位は下式(A−4)参照)。
尚、前記ケイ素含有樹脂(A−4)の構成モノマー比(a:b:c)は20:50:30(mol%)であり、Mwは3500であった。
(Synthesis Example 4) Resin Solution No. 4
Into a nitrogen-substituted quartz three-necked flask, 1.1 g of a 20% maleic acid aqueous solution and 69.0 g of ultrapure water were added and heated to 65 ° C. Next, 24.6 g (0.16 mol) of tetramethoxysilane, 55.0 g (0.40 mol) of methyltrimethoxysilane, 35.9 g (0.24 mol) of vinyltrimethoxysilane, and propylene glycol monoethyl ether 14. A solution in which 4 g was mixed was dropped into the reaction vessel over 1 hour and stirred at 65 ° C. for 2 hours. This reaction liquid was returned to room temperature and concentrated under reduced pressure until the solid content concentration became 30% to obtain 187 g of a silicon-containing resin solution (resin solution No. 4). The resin in this resin solution is referred to as silicon-containing resin (A-4) (refer to the following formula (A-4) for the structural unit).
The constituent monomer ratio (a: b: c) of the silicon-containing resin (A-4) was 20:50:30 (mol%), and Mw was 3,500.
[2]重合体(C)の製造
下式で表される下記の各化合物[化合物(c1−1)、(c1−2)、(c2−1)、(c3−1)及び(c4−1)]を用いて、以下のように重合体(C−1)〜(C−7)を合成した。尚、各合成例で得られる重合体の重量平均分子量(Mw)及び分散度(Mw/Mn)は下記の方法により行った。
[2] Production of polymer (C) Each of the following compounds represented by the following formula [compounds (c1-1), (c1-2), (c2-1), (c3-1) and (c4-1) )] Were used to synthesize polymers (C-1) to (C-7) as follows. In addition, the weight average molecular weight (Mw) and dispersion degree (Mw / Mn) of the polymer obtained by each synthesis example were performed by the following method.
化合物(c1−1):メタクリル酸テトラヒドロフルフリル
化合物(c1−2):メタクリル酸グリシジル
化合物(c2−1):メタクリル酸−4−オキサ−5−オキソ−トリシクロ[4.2.1.03,7]ノナ−2−イルエステル
化合物(c3−1):メタクリル酸イソブチル
化合物(c4−1):メタクリル酸−2−ヒドロキシエチル
Compound (c1-1): Tetrahydrofurfuryl methacrylate Compound (c1-2): Glycidyl methacrylate Compound (c2-1): Methacrylic acid-4-oxa-5-oxo-tricyclo [4.2.1.0 3 , 7 ] Non-2-yl ester Compound (c3-1): Isobutyl methacrylate Compound (c4-1): 2-hydroxyethyl methacrylate
(Mw、Mw/Mnの測定)
東ソー(株)製GPCカラム(G2000HXL2本、G3000HXL1本、G4000HXL1本)を用い、流量1.0ミリリットル/分、溶出溶媒テトラヒドロフラン、カラム温度40℃の分析条件で、単分散ポリスチレンを標準とするゲルパーミエーションクロマトグラフィ(GPC)により測定した。また、分散度Mw/Mnは測定結果より算出した。
(Measurement of Mw, Mw / Mn)
Gel permeation based on monodisperse polystyrene using GPC columns (2 G2000HXL, 1 G3000HXL, 1 G4000HXL) manufactured by Tosoh Corporation under the analysis conditions of flow rate 1.0 ml / min, elution solvent tetrahydrofuran, column temperature 40 ° C. It was measured by an association chromatography (GPC). Further, the degree of dispersion Mw / Mn was calculated from the measurement results.
(1)重合体(C−1)の合成
メタクリル酸テトラヒドロフルフリル[前記化合物(c1−1)]3.44部(70モル%)、メタクリル酸―4−オキサ−5−オキソ−トリシクロ[4.2.1.03,7]ノナ−2−イルエステル[前記化合物(c2−1)]16.46部(30モル%)、を2−ブタノン30部に溶解し、更に重合開始剤としてアゾビスイソブチロニトリル(AIBN)0.99部(5モル%)を投入した単量体溶液を準備した。
次いで、温度計及び滴下漏斗を備えた三つ口フラスコに2−ブタノン30部を投入し、30分窒素パージした。窒素パージの後、フラスコ内をマグネティックスターラーで攪拌しながら80℃になるように加熱した。その後、滴下漏斗を用い、予め準備しておいた単量体溶液を3時間かけて滴下した。滴下開始時を重合開始時間とし、重合反応を6時間実施した。重合終了後、重合溶液は水冷により30℃以下に冷却した。冷却後、400部のメタノールに投入し、析出した白色粉末を濾別した。濾別した白色粉末を、80部のメタノールにてスラリー状で洗浄した。その後、白色粉末を濾別し、50℃にて17時間乾燥し、白色粉末の重合体(C−1)を得た。重合体(C−1)は、Mwが10000であり、Mw/Mnが1.96であった。
(1) Synthesis of polymer (C-1) Tetrahydrofurfuryl methacrylate [said compound (c1-1)] 3.44 parts (70 mol%), methacrylic acid-4-oxa-5-oxo-tricyclo [4] 2.1.0 3,7 ] non-2-yl ester [the above compound (c2-1)] (16.46 parts, 30 mol%) was dissolved in 30 parts of 2-butanone, and further used as a polymerization initiator. A monomer solution charged with 0.99 parts (5 mol%) of azobisisobutyronitrile (AIBN) was prepared.
Next, 30 parts of 2-butanone was charged into a three-necked flask equipped with a thermometer and a dropping funnel, and purged with nitrogen for 30 minutes. After purging with nitrogen, the inside of the flask was heated to 80 ° C. while stirring with a magnetic stirrer. Then, the monomer solution prepared beforehand was dripped over 3 hours using the dropping funnel. The polymerization start was carried out for 6 hours with the start of dropping as the polymerization start time. After completion of the polymerization, the polymerization solution was cooled to 30 ° C. or less by water cooling. After cooling, it was added to 400 parts of methanol, and the precipitated white powder was filtered off. The white powder separated by filtration was washed as a slurry with 80 parts of methanol. Thereafter, the white powder was filtered off and dried at 50 ° C. for 17 hours to obtain a white powder polymer (C-1). The polymer (C-1) had Mw of 10,000 and Mw / Mn of 1.96.
(2)重合体(C−2)〜(C−7)の合成
下記表1に示す種類及び仕込み量の化合物(単量体)を用いること以外は、前述の重合体(C−1)と同様の手法にて、重合体(C−2)〜(C−7)を合成した。
尚、表1には、重合体(C−1)〜(C−7)の分子量(Mw)及び分散度(Mw/Mn)を併記した。
(2) Synthesis of polymers (C-2) to (C-7) The polymer (C-1) and the polymer (C-1) described above were used except that the compounds (monomers) having the types and amounts shown in Table 1 below were used. Polymers (C-2) to (C-7) were synthesized in the same manner.
In Table 1, the molecular weight (Mw) and dispersity (Mw / Mn) of the polymers (C-1) to (C-7) are also shown.
[3]ネガ型感放射線性組成物の調製
表2に示す割合で、ポリシロキサン溶液と、(B)酸発生剤と、(C)重合体と、(E)酸拡散制御剤と、(F)界面活性剤とを混合し、実験例1〜16及び比較例1〜2の各ネガ型感放射線性組成物を調製した。また、これらの組成物は固形分濃度が17%となるように、(D)溶剤として、プロピレングリコールモノメチルエーテルアセテートを配合した。尚、実験例1〜16のうち、実験例1〜10及び実験例12〜16が実施例である。
[3] Preparation of Negative Radiation Sensitive Composition Polysiloxane solution, (B) acid generator, (C) polymer, (E) acid diffusion controller, and (F) in the proportions shown in Table 2. ) were mixed with a surfactant, each radiation-sensitive composition of experiment examples 1 to 16 and Comparative examples 1 and 2 were prepared. Moreover, propylene glycol monomethyl ether acetate was mix | blended as (D) solvent so that these compositions might be set to 17% of solid content concentration. Of Experimental Examples 1 to 16, Experimental Examples 1 to 10 and Experimental Examples 12 to 16 are examples.
尚、前記表2における各成分の詳細は以下の通りである。
<酸発生剤(B)>
(B−1):トリフェニルスルホニウムノナフルオロ−n−ブタンスルホネート
(B−2):1−(4−n−ブトキシナフチル)テトラヒドロチオフェニウムパーフルオロ−n−ブタンスルホネート
(B−3):トリフェニルスルホニウム2−(ビシクロ[2.2.1]ヘプタ−2’−イル)−1,1,2,2−テトラフルオロエタンスルホネート
<酸拡散抑制剤(E)>
(E−1):2−フェニルベンズイミダゾール
(E−2):N−t−ブトキシカルボニル−2−フェニルベンズイミダゾール
<界面活性剤(F)>
(F−1):SH8400 FLUID(Toray Dow Corning Silicone Co.製)
The details of each component in Table 2 are as follows.
<Acid generator (B)>
(B-1): Triphenylsulfonium nonafluoro-n-butanesulfonate (B-2): 1- (4-n-butoxynaphthyl) tetrahydrothiophenium perfluoro-n-butanesulfonate (B-3): Tri Phenylsulfonium 2- (bicyclo [2.2.1] hepta-2'-yl) -1,1,2,2-tetrafluoroethanesulfonate <Acid Diffusion Inhibitor (E)>
(E-1): 2-phenylbenzimidazole (E-2): Nt-butoxycarbonyl-2-phenylbenzimidazole <Surfactant (F)>
(F-1): SH8400 FLUID (Toray Dow Corning Silicon Co.)
[4]ネガ型感放射線性組成物の評価
実験例1〜16及び比較例1〜2の各組成物について、以下のように下記(1)〜(4)の各種評価を行い、その結果を表3に示した。
[4] for each composition of the evaluation experiments Examples 1 to 16 and Comparative Examples 1 and 2 of the radiation-sensitive composition, to perform various evaluation of the following (1) to (4) as follows, as a result Are shown in Table 3.
(1)解像度
基板として、表面に膜厚77nmの下層反射防止膜(「ARC29A」、ブルワー・サイエンス社製)を形成した8インチシリコンウェハを用いた。尚、反射防止膜の形成には、半導体製造装置「CLEAN TRACK ACT8」(東京エレクトロン株式会社製)を用いた。
その後、各ネガ型感放射線性組成物を前記基板上に、前記CLEAN TRACK ACT8にて、スピンコートし、表3の条件でベーク(PB)を60秒間行うことにより、膜厚220nmの被膜を形成した。次いで、この被膜に、ArFエキシマレーザー露光装置(NIKON製、「NSR S306C」)にて、NA=0.78、σ=0.85−1/2輪帯照明の条件で、マスクパターンを介して露光した。
そして、表3に示す条件でPEBを60秒間行ったのち、2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液により、23℃で60秒間現像した。その後、水洗及び乾燥して、ネガ型パターンを形成した。このとき、線幅150nmのライン・アンド・スペースパターン(1L1S)を1対1の線幅に形成する露光量を最適露光量とし、この最適露光量を感度(mJ/cm2)とした。この感度にて、各種線幅の1L1Sパターンを観察したときの、パターンが解像している最小線幅パターンを限界解像度とした。尚、線幅の測長には走査型電子顕微鏡(株式会社日立ハイテクノロジーズ社製、「S−9380」)を用いた。
(1) Resolution As the substrate, an 8-inch silicon wafer having a 77 nm-thick lower layer antireflection film (“ARC29A”, manufactured by Brewer Science) on the surface was used. For the formation of the antireflection film, a semiconductor manufacturing apparatus “CLEAN TRACK ACT8” (manufactured by Tokyo Electron Limited) was used.
Thereafter, each negative radiation-sensitive composition is spin-coated on the substrate by the CLEAN TRACK ACT8, and baking (PB) is performed for 60 seconds under the conditions shown in Table 3 to form a film having a thickness of 220 nm. did. Next, this film was coated with an ArF excimer laser exposure apparatus (manufactured by NIKON, “NSR S306C”) through a mask pattern under conditions of NA = 0.78 and σ = 0.85-1 / 2 annular illumination. Exposed.
And after performing PEB for 60 second on the conditions shown in Table 3, it developed for 60 second at 23 degreeC with 2.38 mass% tetramethylammonium hydroxide aqueous solution. Then, it was washed with water and dried to form a negative pattern. At this time, an exposure amount for forming a line-and-space pattern (1L1S) having a line width of 150 nm in a one-to-one line width was defined as an optimum exposure amount, and this optimum exposure amount was defined as sensitivity (mJ / cm 2 ). With this sensitivity, when the 1L1S pattern having various line widths was observed, the minimum line width pattern that the pattern was resolved was defined as the limit resolution. A scanning electron microscope (manufactured by Hitachi High-Technologies Corporation, “S-9380”) was used for measuring the line width.
(2)焦点深度(DOF)
前記(1)と同様に形成した線幅150nmのライン・アンド・スペースパターン(1L1S)での感度において、各種焦点の1L1Sパターンを観察し、下記式より焦点深度を算出した。
尚、線幅の測長には走査型電子顕微鏡(株式会社日立ハイテクノロジーズ社製、「S−9380」)を用いた。
焦点深度(μm)=|F1−F2|(即ち、F1とF2との差の絶対値)
F1:線幅165nmとなるときの焦点(μm)
F2:線幅135nmとなるときの焦点(μm)
(2) Depth of focus (DOF)
Regarding the sensitivity with a line-and-space pattern (1L1S) having a line width of 150 nm formed in the same manner as in (1) above, 1L1S patterns of various focal points were observed, and the depth of focus was calculated from the following formula.
A scanning electron microscope (manufactured by Hitachi High-Technologies Corporation, “S-9380”) was used for measuring the line width.
Depth of focus (μm) = | F1−F2 | (ie, absolute value of difference between F1 and F2)
F1: Focus when the line width is 165 nm (μm)
F2: Focus when the line width is 135 nm (μm)
(3)パターン形状
前記(1)と同様に形成した線幅150nmのライン・アンド・スペースパターン(1L1S)の断面形状を観察した。この際、図1に示す断面形状における(b)、(c)又は(d)の場合を「良好」とし、(a)、(e)又は(f)の場合を「不良」とした。尚、この断面形状の観察には走査電子顕微鏡(株式会社日立ハイテクノロジーズ社製、「S−4800」)を用いた。
(3) Pattern shape The cross-sectional shape of the line and space pattern (1L1S) with a line width of 150 nm formed in the same manner as in (1) was observed. At this time, the case of (b), (c) or (d) in the cross-sectional shape shown in FIG. 1 was “good”, and the case of (a), (e) or (f) was “bad”. A scanning electron microscope (manufactured by Hitachi High-Technologies Corporation, “S-4800”) was used for the observation of the cross-sectional shape.
(4)比誘電率測定
基板として、0.1Ω・cm以下の抵抗率を有する8インチのN型シリコンウエハーを用いた。次いで、各ネガ型感放射線性組成物を前記基板上に、CLEAN TRACK ACT8にて、スピンコートし、表3の条件でベーク(PB)を行うことにより、膜厚600nmの被膜を形成した。その後、この被膜に、KrFエキシマレーザー液浸露光装置(「NSR S203B」、NIKON製)にてNA=0.68、σ=0.75の条件でマスクを介さずにウエハ全面を露光した。その後、表3に示す条件でPEBを行ったのち、2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液により、23℃で60秒間現像し、水洗し、乾燥した。次いで、窒素雰囲気下420℃で30分間加熱し、硬化膜を得た。
得られた硬化膜に、蒸着法によりアルミニウム電極パターンを形成し、比誘電率測定用サンプルを作成した。このサンプルについて、周波数100kHzの周波数で、アジデント社製、「HP16451B電極」及び「HP4284AプレシジョンLCRメーター」を用いてCV法により、200℃における硬化膜の比誘電率を測定した。
(4) Relative permittivity measurement An 8-inch N-type silicon wafer having a resistivity of 0.1 Ω · cm or less was used as a substrate. Next, each negative radiation-sensitive composition was spin-coated on the substrate by CLEAN TRACK ACT8, and baked (PB) under the conditions shown in Table 3 to form a film having a thickness of 600 nm. Thereafter, the entire surface of the wafer was exposed to this coating film with a KrF excimer laser immersion exposure apparatus (“NSR S203B”, manufactured by NIKON) under the conditions of NA = 0.68 and σ = 0.75 without using a mask. Then, after performing PEB on the conditions shown in Table 3, it developed with 23.degree. C. for 60 seconds with 2.38 mass% tetramethylammonium hydroxide aqueous solution, washed with water, and dried. Subsequently, it heated at 420 degreeC under nitrogen atmosphere for 30 minutes, and the cured film was obtained.
An aluminum electrode pattern was formed on the obtained cured film by a vapor deposition method, and a sample for measuring relative permittivity was prepared. With respect to this sample, the relative dielectric constant of the cured film at 200 ° C. was measured at a frequency of 100 kHz by the CV method using “HP16451B electrode” and “HP4284A precision LCR meter” manufactured by Agilent.
[4]デュアルダマシン構造を有する硬化パターンの形成
<実験例17(実施例)>
デュアルダマシン構造を有する硬化パターンの形成方法を、図2を用いて説明する。
(1)工程(II−1)[工程(a)参照]
基板1としては、表面に膜厚60nmの下層反射防止膜(「DUV42−6」、日産化学工業株式会社製)を形成した8インチシリコンウェハを用いた。尚、下層反射防止膜の形成には、「CLEAN TRACK ACT8」(東京エレクトロン株式会社製)を用いた。
次いで、前記実験例3の感放射線性組成物を前記基板1上に、前記CLEAN TRACK ACT8にて、スピンコートし、90℃で60秒間ベーク(PB)を行うことにより、膜厚500nmの被膜を形成した。この被膜に、KrFエキシマレーザー露光装置(「NSR S203B」、NIKON製)にてNA=0.68、σ=0.75、1/2輪帯照明の条件で、ホールパターンを有するマスクパターンを介して28mJ/cm2露光した。その後、85℃で60秒間ベーク(PEB)を行ったのち、2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液により、23℃で60秒間現像し、水洗し、乾燥して、ホール径200nmのホール・アンド・スペースパターン(1H2S)のネガ型ホールパターン2aを有するネガ型ホールパターン基板3を形成した。
(2)工程(II−2)[工程(b)及び(c)参照]
ネガ型ホールパターン基板3上に、前記実験例3の感放射線性組成物を前記CLEAN TRACK ACT8にて、スピンコートし、90℃で60秒間ベーク(PB)を行うことにより、ネガ型ホールパターン基板3上に被膜4(膜厚x;500nm)を形成した。この被膜4に、KrFエキシマレーザー露光装置(「NSR S203B」、NIKON製)にてNA=0.68、σ=0.75、1/2輪帯照明の条件で、ラインパターンを有するマスクパターン5を介して32mJ/cm2露光した。その後、85℃で60秒間ベーク(PEB)を行ったのち、2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液により、23℃で60秒間現像した。次いで、水洗し、乾燥して、ネガ型ホールパターン基板3上に、ライン幅240nmのライン・アンド・スペースパターン(1L3S)のネガ型ラインパターンを形成することにより、ネガ型トレンチパターン7aを有するネガ型デュアルダマシンパターン基板8を形成した。
(3)工程(II−3)[工程(d)参照]
次いで、窒素雰囲気下、420℃で30分間加熱し、デュアルダマシン構造を有する硬化パターン9を得た。
ここで、デュアルダマシン構造を有するネガ型のパターンの断面を示す画像を図3に示す。
[4] Formation of cured pattern having a dual damascene structure <Experiment Example 17 (Example)>
A method for forming a cured pattern having a dual damascene structure will be described with reference to FIG.
(1) Step (II-1) [Refer to Step (a)]
As the substrate 1, an 8-inch silicon wafer having a lower layer antireflection film (“DUV42-6”, manufactured by Nissan Chemical Industries, Ltd.) having a film thickness of 60 nm formed on the surface was used. In addition, “CLEAN TRACK ACT8” (manufactured by Tokyo Electron Limited) was used for forming the lower antireflection film.
Then, the experimental example 3 of the radiation-sensitive composition onto the substrate 1 at the CLEAN TRACK ACT8, by spin coating, by performing 60 seconds baked (PB) at 90 ° C., the thickness 500nm of the film Formed. On this film, a KrF excimer laser exposure apparatus (“NSR S203B”, manufactured by NIKON) was passed through a mask pattern having a hole pattern under the conditions of NA = 0.68, σ = 0.75, and 1/2 annular illumination. 28 mJ / cm 2 exposure. Thereafter, baking (PEB) was performed at 85 ° C. for 60 seconds, and then developed with a 2.38 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 60 seconds, washed with water, and dried. A negative hole pattern substrate 3 having an AND space pattern (1H2S) negative hole pattern 2a was formed.
(2) Step (II-2) [Refer to Steps (b) and (c)]
On negative hole pattern substrate 3, the in Experiment Example 3 of the radiation-sensitive composition CLEAN TRACK ACT8, by spin coating, by performing 60 seconds baked (PB) at 90 ° C., negative hole pattern A film 4 (film thickness x; 500 nm) was formed on the substrate 3. A mask pattern 5 having a line pattern is formed on this coating 4 under the conditions of NA = 0.68, σ = 0.75, and 1/2 annular illumination with a KrF excimer laser exposure apparatus (“NSR S203B”, manufactured by NIKON). Was exposed to 32 mJ / cm 2 . Then, after baking (PEB) at 85 ° C. for 60 seconds, development was performed at 23 ° C. for 60 seconds with a 2.38 mass% tetramethylammonium hydroxide aqueous solution. Next, it is washed with water and dried to form a negative line pattern of a line and space pattern (1L3S) having a line width of 240 nm on the negative hole pattern substrate 3, thereby having a negative having a negative trench pattern 7a. A type dual damascene pattern substrate 8 was formed.
(3) Step (II-3) [Refer to Step (d)]
Subsequently, it heated for 30 minutes at 420 degreeC in nitrogen atmosphere, and the hardening pattern 9 which has a dual damascene structure was obtained.
Here, an image showing a cross-section of a negative pattern having a dual damascene structure is shown in FIG.
[5]実施例の評価
表3によれば、本実験例1〜16のネガ型感放射線性組成物は、高解像度であり、焦点深度(DOF)にも優れており、得られるパターン形状が良好であり、且つ低比誘電率な硬化パターンを形成することができることが分かった。
According to the evaluation Table 3 [5] Example, radiation-sensitive composition of the present experiment example 1 to 16 is a high resolution, and excellent focal depth (DOF), the obtained pattern shape It was found that a cured pattern having a good dielectric constant and a low relative dielectric constant can be formed.
本発明のネガ型感放射線性組成物は、活性光線、例えば、KrFエキシマレーザー(波長248nm)或いはArFエキシマレーザー(波長193nm)に代表される遠紫外線並びに電子線に感応する化学増幅型レジストの形成材料として有用であり、高解像性を有し、焦点深度(DOF)にも優れており、得られるパターン形状が良好であり、且つ低比誘電率な硬化膜を与えるため、今後ますます微細化が進行すると予想される集積回路素子の製造に極めて好適に使用することができる。 The negative radiation-sensitive composition of the present invention forms a chemically amplified resist that is sensitive to actinic rays, for example, far-ultraviolet rays such as KrF excimer laser (wavelength 248 nm) or ArF excimer laser (wavelength 193 nm) and electron beams. It is useful as a material, has high resolution, is excellent in depth of focus (DOF), has a good pattern shape, and gives a cured film with a low relative dielectric constant. Therefore, it can be used very favorably for the manufacture of integrated circuit elements, which are expected to be processed.
1;基板、2a;ネガ型ホールパターン、2b;ホール、3;ネガ型ホールパターン基板、4;ネガ型感放射線性組成物の被膜、5;マスク(レチクル)、6;露光、7a;ネガ型トレンチパターン、7b;トレンチ、8;ネガ型デュアルダマシンパターン基板、9;デュアルダマシン構造を有する硬化パターン、x;ネガ型感放射線性組成物由来の被膜の膜厚。 DESCRIPTION OF SYMBOLS 1; Substrate, 2a; Negative hole pattern, 2b; Hole, 3; Negative hole pattern substrate, 4; Negative-type radiation-sensitive composition coating, 5; Mask (reticle), 6; Exposure, 7a; Trench pattern, 7b; trench, 8; negative dual damascene pattern substrate, 9; cured pattern having dual damascene structure, x; film thickness of coating derived from negative radiation sensitive composition.
Claims (13)
(B)感放射線性酸発生剤と、
(C)下記一般式(1)で表される構造単位(c1)を含む重合体と、
(D)溶剤と、を含有し、
前記(A)ポリシロキサンが、下記一般式(5)で表される有機ケイ素化合物(a1)及び下記一般式(6)で表される有機ケイ素化合物(a2)を含む加水分解性シラン化合物を加水分解縮合させて得られたポリシロキサンであるネガ型感放射線性組成物。
〔一般式(5)において、R 9 は1価の有機基を示す。〕
〔一般式(6)において、R 10 は水素原子、フッ素原子、炭素数1〜5の直鎖状若しくは分岐状のアルキル基、シアノ基、シアノアルキル基又はアルキルカルボニルオキシ基を示す。R 11 は1価の有機基を示す。aは1〜3の整数を示す。〕 (A) polysiloxane;
(B) a radiation sensitive acid generator;
(C) a polymer containing a structural unit (c1) represented by the following general formula (1);
(D) a solvent ,
The (A) polysiloxane hydrolyzes a hydrolyzable silane compound containing an organosilicon compound (a1) represented by the following general formula (5) and an organosilicon compound (a2) represented by the following general formula (6). A negative radiation sensitive composition which is a polysiloxane obtained by decomposing and condensing .
[In General Formula (5), R 9 represents a monovalent organic group. ]
[In General Formula (6), R 10 represents a hydrogen atom, a fluorine atom, a linear or branched alkyl group having 1 to 5 carbon atoms, a cyano group, a cyanoalkyl group, or an alkylcarbonyloxy group. R 11 represents a monovalent organic group. a represents an integer of 1 to 3. ]
前記工程(i)により得られた塗膜をベークする工程(ii)と、
前記工程(ii)により得られた膜を露光する工程(iii)と、
前記工程(iii)により得られた、露光された膜をベークする工程(iv)と、
前記工程(iv)により得られた膜を現像液で現像し、ネガ型パターンを形成する工程(v)と、
前記工程(v)により得られたネガ型パターンに、高エネルギー線照射及び加熱のうちの少なくとも一方の硬化処理を施し、硬化パターンを形成する工程(vi)と、を備えることを特徴とする硬化パターン形成方法。 Applying the negative radiation-sensitive composition according to any one of claims 1 to 6 to a substrate to form a coating film (i);
A step (ii) of baking the coating film obtained by the step (i);
Exposing the film obtained by the step (ii) (iii);
A step (iv) of baking the exposed film obtained by the step (iii);
Developing the film obtained in the step (iv) with a developer to form a negative pattern (v);
A step (vi) of forming a cured pattern by subjecting the negative pattern obtained by the step (v) to at least one of high energy ray irradiation and heating to form a cured pattern. Pattern forming method.
(II−2)得られたネガ型ホールパターン基板上に、請求項1乃至6のいずれか1項に記載のネガ型感放射線性組成物を塗布、露光、現像し、前記ネガ型ホールパターン基板上に、ネガ型トレンチパターンを形成し、ネガ型デュアルダマシンパターン基板を形成する工程と、
(II−3)得られたネガ型デュアルダマシンパターン基板に、高エネルギー線照射及び加熱のうちの少なくとも一方の処理を施し、デュアルダマシン構造を有する硬化パターンを形成する工程と、を備えることを特徴とする硬化パターン形成方法。 (II-1) Applying, exposing and developing the negative radiation-sensitive composition according to any one of claims 1 to 6 to a substrate, forming a negative hole pattern substrate having a negative hole pattern; ,
(II-2) On the obtained negative hole pattern substrate, the negative radiation sensitive composition according to any one of claims 1 to 6 is applied, exposed and developed, and the negative hole pattern substrate. Forming a negative trench pattern on the top and forming a negative dual damascene pattern substrate;
(II-3) The obtained negative dual damascene pattern substrate is subjected to at least one of high energy ray irradiation and heating to form a cured pattern having a dual damascene structure. A cured pattern forming method.
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