JP2002236358A5 - - Google Patents

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JP2002236358A5
JP2002236358A5 JP2001032855A JP2001032855A JP2002236358A5 JP 2002236358 A5 JP2002236358 A5 JP 2002236358A5 JP 2001032855 A JP2001032855 A JP 2001032855A JP 2001032855 A JP2001032855 A JP 2001032855A JP 2002236358 A5 JP2002236358 A5 JP 2002236358A5
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group
acid
substituted
resist composition
compound
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JP2001032855A
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JP4145017B2 (en
JP2002236358A (en
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Priority to JP2001032855A priority Critical patent/JP4145017B2/en
Priority claimed from JP2001032855A external-priority patent/JP4145017B2/en
Priority to KR1020020005898A priority patent/KR100796585B1/en
Priority to TW091101972A priority patent/TW571178B/en
Publication of JP2002236358A publication Critical patent/JP2002236358A/en
Publication of JP2002236358A5 publication Critical patent/JP2002236358A5/ja
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【特許請求の範囲】
【請求項1】(a)カルボニル基を少なくとも1つ有し、活性光線の照射により分子内水素ラジカル移動を伴って分解し、酸を発生する化合物を少なくとも一種含有する感放射線性レジスト組成物。
【請求項2】(a)成分が一般式(I)叉は(II)で表される化合物であることを特徴とする請求項1に記載の感放射線性レジスト組成物。
【化1】

Figure 2002236358
1及びR2は、同一でも異なっていてもよく、水素原子又は1価の有機基を表す。または、R1とR2とが結合して、ヘテロ原子、多重結合、−CO−、−COO−を含有してもよい単環または多環の環構造を形成してもよい。
3及びR4は、同一でも異なっていてもよく、水素原子又は1価の有機基を表す。
R’は、置換していてもよい直鎖、分岐、環状アルキル基、置換していてもよいアリール基、置換していてもよいアラルキル基、叉は置換していてもよいカンファー基を表す。
Xは、水素ラジカル供与性基を有する1価の有機基を表す。また、Xは、R1或いはR2と結合して単環または多環の環構造を形成してもよい。
一般式(I)におけるY1は、R’SO3−、R’COO−、又はハロゲン原子を表す。
一般式(II)におけるY2 -は、非求核アニオンを表す。
Ra及びRbは、置換してもよい直鎖、分岐、環状アルキル基、置換していてもよいアリール基、叉は置換してもよいアラルキル基を表す。また、Ra及びRbが結合して環を形成してもよい。
1〜R4、Ra、Rb、X、Y1、Y2 -のいずれかの位置で連結基を介して結合し、一般式(I)または(II)の構造を2つ有することもできる。
【請求項3】(A)カルボニル基を少なくとも1つ有し、活性光線の照射により、分子内水素ラジカル移動を伴って分解し、酸を発生する化合物少なくとも1種、及び、
(B)酸の作用により分解し、アルカリ現像液中での溶解度を増大させる基を有する樹脂
を含有することを特徴とするポジ型感放射線性レジスト組成物。
【請求項4】(C)酸により分解しうる基を有し、アルカリ現像液中での溶解速度が酸の作用により増大する、分子量3000以下の低分子溶解阻止化合物を更に含有することを特徴とする請求項2に記載のポジ型感放射線性レジスト組成物。
【請求項5】(A)カルボニル基を少なくとも1つ有し、活性光線の照射により分子内水素ラジカル移動を伴って分解し、酸を発生する化合物少なくとも1種
(B)酸により分解しうる基を有し、アルカリ現像液中での溶解速度が酸の作用により増大する、分子量3000以下の低分子溶解阻止化合物、及び、
(D)水に不溶でアルカリ現像液に可溶な樹脂
を含有することを特徴とするポジ型感放射線性レジスト組成物。
【請求項6】(A)カルボニル基を少なくとも1つ有し、活性光線の照射により分子内水素ラジカル移動を伴って分解し、酸を発生する化合物少なくとも1種、
(D)アルカリ現像液に可溶な樹脂、及び、
(E)酸架橋剤、
を含有することを特徴とするネガ型感放射線性レジスト組成物。
【請求項7】 請求項1〜6のいずれかに記載の感放射線性レジスト組成物によりレジスト膜を形成し、当該レジスト膜を露光、現像することを特徴とするパターン形成方法。 [Claims]
1. A radiation-sensitive resist composition comprising (a) at least one compound having at least one carbonyl group and decomposing upon irradiation with actinic rays with the transfer of intramolecular hydrogen radicals to generate an acid.
2. The radiation-sensitive resist composition according to claim 1, wherein the component (a) is a compound represented by the general formula (I) or (II).
Embedded image
Figure 2002236358
R 1 and R 2 may be the same or different and represent a hydrogen atom or a monovalent organic group. Alternatively, R 1 and R 2 may combine to form a monocyclic or polycyclic ring structure which may contain a heteroatom, a multiple bond, —CO—, or —COO—.
R 3 and R 4 may be the same or different and represent a hydrogen atom or a monovalent organic group.
R ′ represents a linear, branched, or cyclic alkyl group which may be substituted, an aryl group which may be substituted, an aralkyl group which may be substituted, or a camphor group which may be substituted.
X represents a monovalent organic group having a hydrogen radical donating group. X may combine with R 1 or R 2 to form a monocyclic or polycyclic ring structure.
Y 1 in the general formula (I) represents R′SO 3 —, R′COO—, or a halogen atom.
Y 2 in the general formula (II) - represents a non-nucleophilic anion.
Ra and Rb represent a linear, branched or cyclic alkyl group which may be substituted, an aryl group which may be substituted, or an aralkyl group which may be substituted. Ra and Rb may combine to form a ring.
R 1 to R 4 , Ra, Rb, X, Y 1 , and Y 2 may be bonded via a linking group at any position to have two structures of the general formula (I) or (II). .
(A) at least one compound which has at least one carbonyl group, decomposes upon irradiation with an actinic ray together with intramolecular hydrogen radical transfer to generate an acid, and
(B) A positive-type radiation-sensitive resist composition comprising a resin having a group which is decomposed by the action of an acid and increases the solubility in an alkaline developer.
4. A low molecular weight dissolution inhibiting compound having a molecular weight of 3000 or less which has a group decomposable by an acid and whose dissolution rate in an alkaline developer is increased by the action of an acid. The positive-type radiation-sensitive resist composition according to claim 2, wherein
5. A compound having at least one carbonyl group (A), which decomposes upon irradiation with actinic rays with intramolecular hydrogen radical transfer to generate an acid, and (B) a group decomposable by an acid. Having a molecular weight of 3000 or less, wherein the dissolution rate in an alkali developer is increased by the action of an acid, and
(D) A positive-type radiation-sensitive resist composition comprising a resin which is insoluble in water and soluble in an alkali developing solution.
(A) at least one compound which has at least one carbonyl group, decomposes upon irradiation with actinic rays together with intramolecular hydrogen radical transfer to generate an acid,
(D) a resin soluble in an alkali developer, and
(E) an acid crosslinking agent,
A negative-type radiation-sensitive resist composition comprising:
7. A resist film is formed by radiation-sensitive composition according to claim 1, a pattern forming method characterized by the resist film to exposure and development.

JP2001032855A 2001-02-08 2001-02-08 Radiation-sensitive resist composition Expired - Fee Related JP4145017B2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2001032855A JP4145017B2 (en) 2001-02-08 2001-02-08 Radiation-sensitive resist composition
KR1020020005898A KR100796585B1 (en) 2001-02-08 2002-02-01 Radiation sensitive resist composition
TW091101972A TW571178B (en) 2001-02-08 2002-02-05 Irradiation-sensitive resist composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2001032855A JP4145017B2 (en) 2001-02-08 2001-02-08 Radiation-sensitive resist composition

Publications (3)

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JP2002236358A JP2002236358A (en) 2002-08-23
JP2002236358A5 true JP2002236358A5 (en) 2006-01-19
JP4145017B2 JP4145017B2 (en) 2008-09-03

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Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002082185A1 (en) * 2001-04-05 2002-10-17 Arch Specialty Chemicals, Inc. Perfluoroalkylsulfonic acid compounds for photoresists
JP4271968B2 (en) 2003-03-13 2009-06-03 富士フイルム株式会社 Positive or negative resist compositions and compounds
JP4533639B2 (en) * 2003-07-22 2010-09-01 富士フイルム株式会社 SENSITIVE COMPOSITION, COMPOUND, AND PATTERN FORMING METHOD USING THE SENSITIVE COMPOSITION
JP2005084240A (en) * 2003-09-05 2005-03-31 Fuji Photo Film Co Ltd Stimulus-sensitive composition, compound, and pattern forming method using stimulus-sensitive composition
WO2010067627A1 (en) * 2008-12-11 2010-06-17 出光興産株式会社 Precursor for acid-dissociable dissolution-inhibitive group and cyclic compound having acid-dissociable dissolution-inhibitive group
JP6030818B2 (en) * 2009-06-23 2016-11-24 住友化学株式会社 Salt for acid generator of resist composition
JP6706955B2 (en) * 2015-04-08 2020-06-10 住友化学株式会社 Salt, acid generator, resist composition, and method for producing resist pattern
US9950999B2 (en) 2016-08-12 2018-04-24 International Business Machines Corporation Non-ionic low diffusing photo-acid generators
US9983475B2 (en) 2016-08-12 2018-05-29 International Business Machines Corporation Fluorinated sulfonate esters of aryl ketones for non-ionic photo-acid generators
WO2018101376A1 (en) * 2016-11-30 2018-06-07 三菱瓦斯化学株式会社 Compound, resin, composition, resist pattern formation method, and circuit pattern formation method
WO2022172602A1 (en) * 2021-02-15 2022-08-18 富士フイルム株式会社 Actinic light-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, and method for producing electronic devices
KR20230158012A (en) * 2021-04-15 2023-11-17 후지필름 가부시키가이샤 Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, electronic device manufacturing method
WO2023127692A1 (en) * 2021-12-28 2023-07-06 東京応化工業株式会社 Resist composition and method for forming resist pattern

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