JP2011150138A - Positive photosensitive resin composition, method for producing pattern cured film, and electronic component - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a positive photosensitive resin composition which is reduced in exposure time and has high sensitivity. <P>SOLUTION: The positive photosensitive resin composition contains (a) a polymer having a phenolic hydroxyl group or carboxyl group, (b) an iodonium compound having two or more iodonium structures in one molecule, (c) a diazonaphthoquinone compound, and (d) a solvent. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to a positive photosensitive resin composition, a method for producing a patterned cured film, and an electronic component. More specifically, for example, the present invention relates to a positive photosensitive resin composition capable of forming a surface protective film and / or an interlayer insulating film of a semiconductor element, and a method for producing a heat resistant pattern cured film using the composition.

Conventionally, polyimide resins and polybenzoxazole resins having excellent heat resistance, electrical characteristics, and mechanical characteristics have been used for interlayer insulating films and surface protective films of semiconductor elements.
In recent years, as semiconductor devices are further highly integrated and enlarged, sealing resin packages are required to be thinner and smaller. Also, methods such as surface mounting by LOC (lead-on-chip) or solder reflow have been taken, and polyimide resins having better mechanical properties and heat resistance are required more than ever. It was.

  In response to these demands, a photosensitive polyimide having a polyimide resin itself imparted with photosensitivity has been used. By using photosensitive polyimide, the pattern production process can be simplified and complicated manufacturing processes can be shortened. A heat-resistant photoresist using a conventional photosensitive polyimide or its precursor and its application are well known.

  As a development of these technologies, a positive photosensitive resin composition that can be developed with an alkaline aqueous solution has been recently proposed. For positive photosensitive polyimide, a method of introducing a 2-nitrobenzyl group into a polyimide precursor via an ester bond (Non-Patent Document 1), a naphthoquinone diazide compound is mixed with a soluble dihydroxylimide or polybenzoxazole precursor Examples thereof include a method (Patent Documents 1 and 2), a method of mixing naphthoquinone diazide with a polyimide precursor (Patent Document 3), and the like.

  Due to further integration in recent years and an increase in wafer size, materials with higher productivity are desired. In order to improve the productivity, for example, a highly sensitive photosensitive material capable of shortening the exposure time is desired. There was a limit to sensitivity. In the case of a chemically amplified photosensitive resin composition, generally, film properties such as stretchability tend to be lowered.

Japanese Examined Patent Publication No. 64-60630 US Pat. No. 4,395,482 JP 52-13315 A

J. et al. Macromol. Sci. Chem. , A24, 12, 1407, 1987.

  The objective of this invention is providing the highly sensitive positive type photosensitive resin composition which can shorten exposure time.

（式中、Ｘ_１は２〜８価の有機基である。Ｙ_１は２〜８価の有機基である。Ｒ_１はそれぞれ水素原子又は炭素数１〜２０の有機基である。Ｒ_２はそれぞれ水素原子又は１価の有機基である。ｐ及びｑはそれぞれ０〜４の整数である。ｌ及びｍはそれぞれ０〜２の整数である。ｌ＋ｍ＋ｐ＋ｑは１以上である。ｎは重合体中の構造単位の数を示す２以上の整数である。）
３．前記（ｂ）成分が、下記式（II）、（III）及び（IV）で示される化合物の群から選択される少なくとも１種である１又は２に記載のポジ型感光性樹脂組成物。

（式中、Ｒ_３〜Ｒ_６はそれぞれ１価の有機基である。Ｘは酸素原子又は２価の有機基である。Ｙ⁻は対アニオンである。Ｚ_１は３価の有機基である。Ｚ_２は４価の有機基である。ｎは１以上の整数である。）
４．前記（ｂ）成分が、下記式（Ｖ）で示される構造である１〜３のいずれかに記載のポジ型感光性樹脂組成物。

（式中、Ｒ_３、Ｒ_４はそれぞれ１価の有機基である。Ｘは酸素原子又は２価の有機基である。Ｙ⁻は対アニオンである。）
５．式（Ｖ）のＸが、下記式（VI）で表される基の群から選択される１つである４に記載のポジ型感光性樹脂組成物。

（式中、Ｒ_７〜Ｒ_２２はそれぞれアルキル基、アルコキシ基、パーフロロアルキル基、ハロゲン原子又は水素原子である。また、互いが結合することで環構造となっていても良い。）
６．式（Ｖ）のＲ_３、Ｒ_４がそれぞれ芳香族基、ヘテロ環基、アルキニル基、アルケニル基から選択される１つである４又は５に記載のポジ型感光性樹脂組成物。
７．式（Ｖ）のＲ_３、Ｒ_４がそれぞれ下記式（VII）で表される基である４〜６のいずれかに記載のポジ型感光性樹脂組成物。

（式中、ｍは０〜５の整数である。Ｒ_２３はそれぞれアルキル基、アルコキシ基、パーフロロアルキル基、ハロゲン原子又は水素原子である。）
８．前記（ａ）成分１００重量部に対し、（ｂ）成分を０．０１〜５０重量部、（ｃ）成分を１〜５０重量部含有する１〜７のいずれかに記載のポジ型感光性樹脂組成物。
９．１〜８のいずれかに記載のポジ型感光性樹脂組成物を硬化させた硬化膜。
１０．１〜８のいずれかに記載のポジ型感光性樹脂組成物を支持基盤上に塗布、乾燥して感光性樹脂膜を形成する工程と、前記感光性樹脂膜を露光する工程と、前記露光後の感光性樹脂膜をアルカリ水溶液を用いて現像してパターン樹脂膜を得る工程と、前記パターン樹脂膜を加熱処理してパターン硬化膜を得る工程とを含むパターン硬化膜の製造方法。
１１．９に記載の硬化膜が層間絶縁膜層又は表面保護膜層として設けられている電子部品。 According to the present invention, the following positive photosensitive resin composition and the like are provided.
1. (A) a polymer having a phenolic hydroxyl group or a carboxy group;
(B) an iodonium compound having two or more iodonium structures in one molecule;
(C) A positive photosensitive resin composition containing a diazonaphthoquinone compound, and (d) a solvent.
2. 2. The positive photosensitive resin composition according to 1, wherein the component (a) is a polymer having a structure represented by the following formula (I).

(In the formula, X ₁ is a divalent to octavalent organic group. Y ₁ is a divalent to octavalent organic group. R ₁ is a hydrogen atom or an organic group having 1 to 20 carbon atoms. R _2. Are each a hydrogen atom or a monovalent organic group, p and q are each an integer of 0 to 4. l and m are each an integer of 0 to 2. l + m + p + q is 1 or more, and n is a polymer. (It is an integer of 2 or more indicating the number of structural units in it.)
3. The positive photosensitive resin composition according to 1 or 2, wherein the component (b) is at least one selected from the group of compounds represented by the following formulas (II), (III), and (IV).

(In the formula, R _{3 to} R ₆ are each a monovalent organic group. X is an oxygen atom or a divalent organic group. Y ⁻ is a counter anion. Z ₁ is a trivalent organic group. Z ₂ is a tetravalent organic group, and n is an integer of 1 or more.)
4). The positive photosensitive resin composition according to any one of 1 to 3, wherein the component (b) has a structure represented by the following formula (V).

(Wherein R ₃ and R ₄ are each a monovalent organic group. X is an oxygen atom or a divalent organic group. Y ⁻ is a counter anion.)
5. 5. The positive photosensitive resin composition according to 4, wherein X in the formula (V) is one selected from the group of groups represented by the following formula (VI).

(In formula, R < ₇ > -R < ₂₂ > is an alkyl group, an alkoxy group, a perfluoroalkyl group, a halogen atom, or a hydrogen atom respectively. Moreover, it may become a ring structure by mutually bonding.)
6). The positive photosensitive resin composition according to 4 or 5, wherein R ₃ and R _{4 in} the formula (V) are each selected from an aromatic group, a heterocyclic group, an alkynyl group, and an alkenyl group.
7). R _3, positive photosensitive resin composition according to any one of 4 to 6 R ₄ is a group represented by the following formula, respectively (VII) of the formula (V).

(In the formula, m is an integer of 0 to 5. R ₂₃ is an alkyl group, an alkoxy group, a perfluoroalkyl group, a halogen atom or a hydrogen atom, respectively.)
8). The positive photosensitive resin according to any one of 1 to 7, containing 0.01 to 50 parts by weight of component (b) and 1 to 50 parts by weight of component (c) with respect to 100 parts by weight of component (a). Composition.
The cured film which hardened the positive photosensitive resin composition in any one of 9.1-8.
Applying the positive photosensitive resin composition according to any one of 10.1 to 8 on a support substrate and drying to form a photosensitive resin film; exposing the photosensitive resin film; A method for producing a patterned cured film, comprising: a step of developing a photosensitive resin film after exposure using an alkaline aqueous solution to obtain a pattern resin film; and a step of heat-treating the pattern resin film to obtain a patterned cured film.
An electronic component provided with the cured film according to 11.9 as an interlayer insulating film layer or a surface protective film layer.

  ADVANTAGE OF THE INVENTION According to this invention, the highly sensitive positive photosensitive resin composition which can shorten exposure time can be provided.

It is a schematic sectional drawing explaining the manufacturing process of the semiconductor device which has a multilayer wiring structure by one Embodiment of this invention. It is a schematic sectional drawing explaining the manufacturing process of the semiconductor device which has a multilayer wiring structure by one Embodiment of this invention. It is a schematic sectional drawing explaining the manufacturing process of the semiconductor device which has a multilayer wiring structure by one Embodiment of this invention. It is a schematic sectional drawing explaining the manufacturing process of the semiconductor device which has a multilayer wiring structure by one Embodiment of this invention. It is a schematic sectional drawing explaining the manufacturing process of the semiconductor device which has a multilayer wiring structure by one Embodiment of this invention.

The positive photosensitive resin composition of the present invention comprises the following component (a), component (b), component (c) and component (d).
(A) a polymer having a phenolic hydroxyl group or a carboxy group (b) an iodonium compound having two or more iodonium structures in one molecule (c) a diazonaphthoquinone compound (d) a solvent

  The positive photosensitive resin composition of the present invention has high sensitivity to light. Therefore, for example, the exposure time in the semiconductor manufacturing process can be shortened, and the productivity of the semiconductor device can be improved.

The component (a) contained in the composition of the present invention is a polymer having a phenolic hydroxyl group or a carboxy group, and is preferably a heavy polymer soluble in an alkaline aqueous solution so that development can be performed with the alkaline aqueous solution in the development step. It is a coalescence. Solubility in an aqueous alkali solution can usually be achieved by having a phenolic hydroxyl group or carboxy group in the structural unit of the polymer.
Examples of such polymers include polyimide precursors such as polyamic acid and polyamic acid ester, polybenzoxazole precursors such as polyhydroxypolyamide, polyimide, polybenzoxazole, polyamides other than the above, polyamideimide, phenol novolac resin, and the like. And what has a phenolic hydroxyl group or a carboxy group is mentioned.

式中、Ｘ_１は２〜８価、好ましくは２〜４価の有機基である。Ｙ_１は２〜８価、好ましくは２〜４価の有機基である。Ｒ_１はそれぞれ水素原子又は炭素数１〜２０の有機基である。Ｒ_２はそれぞれ水素原子又は１価の有機基であり、好ましくは水素原子である。ｐ及びｑはそれぞれ０〜４の整数であり、好ましくは０〜２である。ｌ及びｍはそれぞれ０〜２の整数であり、好ましくは０である。ｌ＋ｍ＋ｐ＋ｑは１以上であり、好ましくはＲ_１又はＲ_２の少なくとも１つは水素原子である。Ｒ_２が水素原子のとき、ＯＲ_２に結合するＸ_１又はＹ_１は芳香環を有する有機基であり、ＯＲ_２は芳香環に結合する。ｌ＋ｍ＋ｐ＋ｑは好ましくは２以上である。ｎは重合体中の構造単位の数を示す２以上の整数であり、好ましくは３〜１０の整数である。 The polymer of component (a) is preferably a polymer having a structure represented by the following formula (I).

In the formula, X ₁ is a divalent to octavalent organic group, preferably a divalent to tetravalent organic group. Y ₁ is a divalent to octavalent organic group, preferably a divalent to tetravalent organic group. R ₁ is a hydrogen atom or an organic group having 1 to 20 carbon atoms. R ₂ is a hydrogen atom or a monovalent organic group, preferably a hydrogen atom. p and q are each an integer of 0 to 4, preferably 0 to 2. l and m are each an integer of 0 to 2, preferably 0. l + m + p + q is 1 or more, and preferably at least one of R ₁ or R ₂ is a hydrogen atom. When R ₂ is a hydrogen atom, _{X 1} or _{Y 1} binds to the OR ₂ is an organic group having an aromatic ring, OR ₂ is attached to the aromatic ring. l + m + p + q is preferably 2 or more. n is an integer of 2 or more indicating the number of structural units in the polymer, preferably an integer of 3 to 10.

  The polymer having the structure represented by the formula (I) has a structure of a polyimide precursor or a polybenzoxazole precursor, which has heat resistance and excellent properties as a photosensitive resin composition. It can be heated after development to cyclize to polyimide or polybenzoxazole having high heat resistance.

The polymer having the structure represented by the formula (I) contains two amide bonds in one structural unit as shown in the structural unit of the formula (I). This is generally formed by the reaction of a carboxylic acid (di-, tri-, tetra-, etc.), an anhydride or derivative thereof with a diamine.
Accordingly, X ₁ in the formula (I) represents a carboxy group having an amide bond formed by reaction with an amine in the structure of the carboxylic acid, anhydride or derivative thereof, and other acid functional groups (that is, carboxy group or It is an organic group showing the structure of a portion excluding an esterified group and a phenolic hydroxyl group or a group in which the hydrogen atom is substituted with a substituent. For example, it is an organic group corresponding to a structure other than the carboxyl group and acid functional group of tetracarboxylic dianhydride or dicarboxylic acid. X ₁ generally preferably contains an aromatic ring, and the carboxy group and other acid functional groups are preferably directly bonded to the aromatic ring.

  Examples of the tetracarboxylic dianhydride include pyromellitic dianhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride, and 2,3,3 ′, 4′-biphenyltetracarboxylic acid. Dianhydride, 2,2 ′, 3,3′-biphenyltetracarboxylic dianhydride, 3,3 ′, 4,4′-benzophenonetetracarboxylic dianhydride, 2,2 ′, 3,3′- Benzophenone tetracarboxylic dianhydride, 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride, 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, 1,1- Bis (3,4-dicarboxyphenyl) ethane dianhydride, 1,1-bis (2,3-dicarboxyphenyl) ethane dianhydride, bis (3,4-dicarboxyphenyl) methane dianhydride, bis (2,3- Carboxyphenyl) methane dianhydride, bis (3,4-dicarboxyphenyl) sulfone dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, 1,2,3,4-cyclopentanetetracarboxylic Acid dianhydride, 2,2-bis (4- (4-aminophenoxy) phenyl) propane, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 2,3,6,7-naphthalenetetracarboxylic Acid dianhydride, 2,3,5,6-pyridinetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, 3,3 ′, 4,4′-tetraphenylsilane Tetracarboxylic dianhydride, 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride, N, N ′-(5,5 ′-(1,1,1,3,3, 3-Hexaflo Ropropane-2,2-diyl) bis (2-hydroxy-1,5-phenylene)) bis (1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxamide) and the like. Or two or more types are used in combination. Moreover, it is not necessarily limited to what was mentioned here.

  Among the above-mentioned tetracarboxylic dianhydrides, pyromellitic dianhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride, 2,3,3 ′, 4′-biphenyltetracarboxylic acid Dianhydride, 2,2 ′, 3,3′-biphenyltetracarboxylic dianhydride, 3,3 ′, 4,4′-benzophenonetetracarboxylic dianhydride, 2,2 ′, 3,3′- Benzophenonetetracarboxylic dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride, N, N ′-( 5,5 ′-(1,1,1,3,3,3-hexafluoropropane-2,2-diyl) bis (2-hydroxy-1,5-phenylene)) bis (1,3-dioxo-1 , 3-Dihydroisobenzofuran-5-carboxy Bromide) is preferable for obtaining a high heat resistance good film properties.

Examples of the dicarboxylic acid include 2-fluoroisophthalic acid, 5-fluoroisophthalic acid, 3-fluorophthalic acid, 2-fluorophthalic acid, 2,4,5,6-tetrafluoroisophthalic acid, 3,4,5, 6-tetrafluorophthalic acid, 4,4'-hexafluoroisopropylidenediphenyl-1,1'-dicarboxylic acid, perfluorosuberic acid, 2,2'-bis (trifluoromethyl) -4,4'-biphenylene Examples thereof include dicarboxylic acid, terephthalic acid, isophthalic acid, 4,4′-oxydiphenyl-1,1′-dicarboxylic acid, and these are used alone or in combination of two or more. It is not necessarily limited to those listed here.
Moreover, these derivatives, for example, the above-mentioned various dicarboxylic acid dihalides (such as dichloride) can also be used.

  Of the above-mentioned dicarboxylic acids and derivatives thereof, terephthalic acid, isophthalic acid, 4,4′-diphenyl ether dicarboxylic acid and derivatives thereof are preferable for obtaining good film properties with high heat resistance, and among them, 4,4′-diphenyl ether dicarboxylic acid. Acids and derivatives thereof (eg, 4,4′-diphenyl ether dicarboxylic acid dihalide) are preferred.

Moreover, in order to adjust alkali solubility, the said dicarboxylic acid may have an acid functional group which shows alkali solubility.
Examples of the dicarboxylic acid having an acid functional group include 4,4 ′-(5,5 ′-(1,1,1,3,3,3-hexafluoropropane-2,2-diyl) bis (2-hydroxy). -1,5-phenylene)) bis (azanediyl) bis (oxomethylene) dibenzoic acid, 4,4 ′-(5,5 ′-(propane-2,2-diyl) bis (2-hydroxy-1,5) -Phenylene)) bis (azanediyl) bis (oxomethylene) dibenzoic acid, 4,4 '-(3,3'-dihydroxybiphenyl-4,4'-diyl) bis (azanediyl) bis (oxomethylene) dibenzoic acid 4,4 ′-(4,4′-sulfonylbis (2-hydroxy-1,4-phenylene)) bis (azanediyl) bis (oxomethylene) dibenzoic acid, 4,4 ′-(6,6′- Oxybis (2-hydroxy-1,6 Phenylene)) bis (azanediyl) bis (oxomethylene) dibenzoic acid, 4,4 ′-(6,6 ′-(propan-2-diyl) bis (2-hydroxy-1,6-phenylene)) bis (azanediyl) ) Bis (oxomethylene) dibenzoic acid, 4,4 ′-(4-hydroxy-1,3-phenylene) bis (azanediyl) bis (oxomethylene) dibenzoic acid, 4,4 ′-(2,5-dihydroxy) -1,4-phenylene) bis (azanediyl) bis (oxomethylene) dibenzoic acid and the like, and these are used alone or in combination of two or more. Moreover, it is not necessarily limited to what was mentioned here.

Among the dicarboxylic acids having an acid functional group described above, 4,4 ′-(5,5 ′-(1,1,1,3,3,3-hexafluoropropane-2,2-diyl) bis (2- Hydroxy-1,5-phenylene)) bis (azanediyl) bis (oxomethylene) dibenzoic acid, 4,4 ′-(5,5 ′-(propane-2,2-diyl) bis (2-hydroxy-1, 5-phenylene)) bis (azanediyl) bis (oxomethylene) dibenzoic acid, 4,4 ′-(3,3′-dihydroxybiphenyl-4,4′-diyl) bis (azanediyl) bis (oxomethylene) dibenzoic acid Acid, 4,4 ′-(4,4′-sulfonylbis (2-hydroxy-1,4-phenylene)) bis (azanediyl) bis (oxomethylene) dibenzoic acid, 4,4 ′-(6,6 ′ -Oxybis (2-hydroxy-1,6- Enylene)) bis (azanediyl) bis (oxomethylene) dibenzoic acid, 4,4 ′-(4-hydroxy-1,3-phenylene) bis (azanediyl) bis (oxomethylene) dibenzoic acid has high heat resistance and good It is preferable for obtaining excellent film properties.
Further, a tricarboxylic acid such as trimellitic acid or its anhydride can be used.

Y ₁ in formula (I) is, for example, an organic group corresponding to the structure of a diamine and / or a diamine having an acid functional group, excluding two amino groups and an acid functional group.

  Examples of the diamine include 4,4′-diaminodiphenyl ether, 4,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylsulfone, 4,4′-diaminodiphenyl sulfide, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis (4-aminophenoxyphenyl) sulfone, bis (3-aminophenoxyphenyl) sulfone, bis (4-aminophenoxy) biphenyl, bis [4- (4- Aminophenoxy) phenyl] ether, 1,4-bis (4-aminophenoxy) benzene, 2,2′-dimethyl-4,4′-diaminobiphenyl, 2,2′-diethyl-4,4′-diaminobiphenyl, 3,3′-dimethyl-4,4′-diaminobiphenyl, , 3′-diethyl-4,4′-diaminobiphenyl, 2,2 ′, 3,3′-tetramethyl-4,4′-diaminobiphenyl, 2,2 ′, 3,3′-tetraethyl-4,4 '-Diaminobiphenyl, 2,2'-dimethoxy-4,4'-diaminobiphenyl, 3,3'-dimethoxy-4,4'-diaminobiphenyl, 2,2'-dihydroxy-4,4'-diaminobiphenyl, 3,3′-dihydroxy-4,4′-diaminobiphenyl, 2,2′-di (trifluoromethyl) -4,4′-diaminobiphenyl and the like may be mentioned, and these may be used alone or in combination of two or more. used. Moreover, it is not necessarily limited to what was mentioned here.

  Among the above diamines, 4,4′-diaminodiphenyl ether, m-phenylenediamine, p-phenylenediamine, bis (4-aminophenoxy) biphenyl, 2,2′-dimethyl-4,4′-diaminobiphenyl, 3, 3'-dimethyl-4,4'-diaminobiphenyl is preferred for obtaining good film properties with high heat resistance.

Moreover, in order to adjust alkali solubility, the said diamine may have an acid functional group which shows alkali solubility.
Examples of the diamine having an acid functional group include 2,4-diaminobenzoic acid, 3,5-diaminobenzoic acid, 3,3′-diaminobiphenyl-5,5′-dicarboxylic acid, and 4,4′-diaminodiphenyl ether. 5,5′-dicarboxylic acid, 4,4′-diaminodiphenylmethane-5,5′-dicarboxylic acid, 4,4′-diaminodiphenylsulfone-5,5′-dicarboxylic acid, 4,4′-diaminodiphenyl sulfide It has one or more carboxy groups such as 5,5′-dicarboxylic acid or isomers thereof, or 4,4′-diamino-3,3′-dihydroxybiphenyl, 2,2-bis (3-amino- 4-hydroxyphenyl) propane, 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane, oxybis (3-amino-4-hydroxy) Enyl), bis (3-amino-4-hydroxyphenyl) sulfone, 2,4-diaminophenol, 1,4-diamino-2,5-dihydroxybenzene, N, N ′-(4-aminophenylcarbonyl) -3 , 3′-dihydroxybiphenyl, N, N ′-(3-aminophenylcarbonyl) -3,3′-dihydroxybiphenyl, N, N ′-(4-aminophenylcarbonyl) 2,2-bis (3-amino- 4-hydroxyphenyl) hexafluoropropane, N, N ′-(3-aminophenylcarbonyl) 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane, N, N ′-(4-aminophenyl) Carbonyl) 2,2-bis (3-amino-4-hydroxyphenyl) propane, N, N ′-(3-aminophenylcarbonyl) 2,2 -Bis (3-amino-4-hydroxyphenyl) propane, N, N '-(4-aminophenylcarbonyl) -oxybis (3-amino-4-hydroxyphenyl), N, N'-(3-aminophenylcarbonyl) ) -Oxybis (3-amino-4-hydroxyphenyl), N, N ′-(4-aminophenylcarbonyl) -bis (3-amino-4-hydroxyphenyl) sulfone, N, N ′-(3-aminophenyl) Carbonyl) -bis (3-amino-4-hydroxyphenyl) sulfone, N, N ′-(4-aminophenylcarbonyl) -2,4-diaminophenol, N, N ′-(3-aminophenylcarbonyl) -2 , 4-diaminophenol, N, N ′-(4-aminophenylcarbonyl) -1,4-diamino-2,5-dihydroxybenzene, N, N Examples include those having a phenol group such as'-(3-aminophenylcarbonyl) -1,4-diamino-2,5-dihydroxybenzene, and these are used alone or in combination of two or more. Moreover, it is not necessarily limited to what was mentioned here.

  Among the above-mentioned diamines having an acid functional group, 3,5-diaminobenzoic acid and 4,4′-diamino-3,3′-dihydroxybiphenyl having a phenol group, 2,2-bis (3-amino) -4-hydroxyphenyl) propane, 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane, oxybis (3-amino-4-hydroxyphenyl), bis (3-amino-4-hydroxyphenyl) Sulfone, 2,4-diaminophenol, 1,4-diamino-2,5-dihydroxybenzene, N, N ′-(4-aminophenylcarbonyl) -3,3′-dihydroxybiphenyl, N, N ′-(3 -Aminophenylcarbonyl) -3,3'-dihydroxybiphenyl, N, N '-(4-aminophenylcarbonyl) 2,2- (3-amino-4-hydroxyphenyl) hexafluoropropane, N, N ′-(3-aminophenylcarbonyl) 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane, N, N ′ -(4-aminophenylcarbonyl) 2,2-bis (3-amino-4-hydroxyphenyl) propane, N, N '-(3-aminophenylcarbonyl) 2,2-bis (3-amino-4-hydroxy) Phenyl) propane, N, N ′-(4-aminophenylcarbonyl) -oxybis (3-amino-4-hydroxyphenyl), N, N ′-(3-aminophenylcarbonyl) -oxybis (3-amino-4-) Hydroxyphenyl), N, N ′-(4-aminophenylcarbonyl) -bis (3-amino-4-hydroxyphenyl) sulfo And N, N '- (3-aminophenyl-carbonyl) - preferred for bis (3-amino-4-hydroxyphenyl) sulfone obtain good alkali developing properties.

In addition, the polymer of formula (I) can introduce a functional group as a monovalent organic group other than a hydrogen atom into R ₁ , thereby controlling solubility during development and / or pattern processing utilizing a photoreaction. It becomes possible. Moreover, alkali solubility can also be controlled by having these functional groups partially and leaving a hydrogen atom in R ₁ .
Examples of the method of introducing a functional group as a monovalent organic group into R ₁ in formula (I) include a method of introducing via an ether bond or an ester bond. As a specific method of introduction, an addition reaction using a deacidification halogen reaction in which a halogen compound or acid halide compound having R ₁ as a substituent is reacted with a group in which R ₁ is a hydrogen atom, or an addition reaction with vinyl ether Etc.

Examples of the organic group having 1 to 20 carbon atoms of R ₁ include methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, t-butyl, cyclopropenyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, and cyclohexenyl. , Norbornyl, norbornenyl, adamantyl, benzyl, p-nitrobenzyl, trifluoromethyl, methoxyethyl, ethoxyethyl, methoxymethyl, ethoxymethyl, methoxyethoxymethyl, benzoxymethyl, tetrahydropyranyl, ethoxytetrahydropyranyl, tetrahydrofuranyl, And organic groups such as 2-trimethylsilylethoxymethyl, trimethylsilyl, t-butyldimethylsilyl, 3-oxocyclohexyl, 9-fluorenylmethyl, and methylthiomethyl. .

Examples of the organic group having 1 to 20 carbon atoms of R ₁ include allyl alcohol, 2-methyl-2-propen-1-ol, crotyl alcohol, 3-buten-1-ol, 3-buten-2-ol, 3-methyl-2-buten-1-ol, 2-methyl-3-buten-1-ol, 3-methyl-3-buten-1-ol, 2-methyl-3-buten-2-ol, 2- Penten-1-ol, 4-penten-1-ol, 3-penten-2-ol, 4-penten-2-ol, 1-penten-3-ol, 4-methyl-3-penten-1-ol, 3-methyl-1-penten-3-ol, 2-hexen-1-ol, 3-hexen-1-ol, 4-hexen-1-ol, 5-hexen-1-ol, 1-hexene-3 -Ol, 1-heptane-3-ol, 6-methyl-5-heptan-2-ol 1-octane-3-ol, citronellol, 3-nonen-1-ol, 5-decan-1-ol, 9-decan-1-ol, 7-decan-1-ol, 1,4-pentadiene-3 -Ol, 2,4-hexadien-1-ol, 1,5-hexadien-3-ol, 1,6-heptadiene-4-ol, 2,4-dimethyl-2,6-heptadien-1-ol, nerol , Geraniol, linalool, 2-cyclohexen-1-ol, 3-cyclohexene-1-methanol, isopulegol, 5-norbornen-2-ol, 5-norbornene-2-methanol, ethylene glycol vinyl ether, 1,4-butanediol vinyl ether 1,6-hexanediol vinyl ether, diethylene glycol vinyl ether, 2-hydroxyethyl acrylate 3-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate, 3-hydroxypropyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, pentaerythritol diacrylate monostearate, pentaerythritol triacrylate, caprolactone 2- (methacryloyl) Carboxyl group for bonding a compound such as loxy) ethyl ester, dicaprolactone 2- (methacryloyloxy) ethyl ester, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate to X ₁ or Y ₁ And a functional group obtained by reacting with. Moreover, it is not necessarily limited to what was mentioned here. Moreover, when the terminal of a polymer has an acidic functional group, it is also possible to introduce these functional groups.

  Among the organic groups having 1 to 20 carbon atoms, methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, t-butyl, methoxyethyl, ethoxyethyl, methoxymethyl, ethoxymethyl, methoxyethoxymethyl, tetrahydro Pyranyl, ethoxytetrahydropyranyl, and tetrahydrofuranyl are preferred for controlling the solubility well.

R _{2 in the} formula (I) is preferably a derivative having 1 to 20 carbon atoms, and examples thereof include the same groups as R ₁ . When R ₂ is the same functional group as R ₁ , the composition of the present invention can be controlled for solubility during development and / or patterned using a photoreaction. Moreover, alkali solubility can also be controlled by having these functional groups partially. Moreover, when the terminal of the polymer of (a) component has an acidic functional group, it is also possible to introduce these functional groups.

  The component (a) may be the same or different at both ends, and is, for example, an amine functional group, a derivative group thereof, an acidic functional group or a derivative group thereof.

  When the amine functional group at the terminal portion is a primary amine, the stability of the photosensitive resin composition may deteriorate due to side reactions, so at least one of the two hydrogen atoms on the amine functional group is another atom or Substitution with other functional groups is preferred for obtaining stability as a photosensitive resin composition. In addition, it is more preferable that the substitution ratio of the other atom or other functional group is 30% to 100% in order to obtain sufficient stability.

  When the terminal part of the component (a) is a derivative of an amine functional group, examples of the substituent on nitrogen derived from the amine functional group include amide, imide, carbamate, sulfonyl, sulfenyl, phosphinyl, and alkylsilyl. It is done. Of these, amide, imide, carbamate, and sulfonyl are preferable in terms of obtaining more excellent cured resin properties.

（式中、Ｒ_２４〜Ｒ_２６は、それぞれ１価の有機基であり、好ましくは炭素数１〜２０の有機基である。Ｒ_２７は２価の有機基である。Ｘ_２は酸素原子、硫黄原子又は窒素原子であり、Ｘ_２が酸素原子又は硫黄原子である場合、ｎ＝１であり、Ｘ_２が窒素原子の場合、ｎ＝２である。） The terminal part of the component (a) is preferably a hydrogen atom or a substituent represented by the following formula (VIII) as a substituent on nitrogen derived from the amine functional group.

(Wherein R _{24 to} R ₂₆ are each a monovalent organic group, preferably an organic group having 1 to 20 carbon atoms. R ₂₇ is a divalent organic group. X ₂ is an oxygen atom, When it is a sulfur atom or a nitrogen atom, and X ₂ is an oxygen atom or a sulfur atom, n = 1, and when X ₂ is a nitrogen atom, n = 2.)

Examples of the monovalent organic group represented by R _{24 to} R ₂₆ include methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, t-butyl, cyclopropenyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, and cyclohexenyl. , Norbornyl, norbornenyl, adamantyl, benzyl, p-nitrobenzyl, trifluoromethyl, methoxyethyl, ethoxyethyl, methoxymethyl, ethoxymethyl, methoxyethoxymethyl, benzoxymethyl, ethoxytetrahydropyranyl, tetrahydrofuranyl, 2-trimethylsilylethoxy Methyl, trimethylsilyl, t-butyldimethylsilyl, 3-oxocyclohexyl, 9-fluorenylmethyl, phenyl, toluyl, xylyl, 9,10-dihydroanthrani , Trimethylphenyl, pentamethylphenyl, biphenyl, terphenyl, quarterphenyl, dimethylbiphenyl, naphthalenyl, methylnaphthalenyl, fluorenyl, fluorophenyl, fluorobiphenyl, isopropylidenebiphenyl, tetrafluoroisopropylidenebiphenyl, benzylphenyl ether, phenyl ether Phenoxytoluyl, methoxybiphenyl, dimethoxybiphenyl, methoxynaphthalenyl, dimethoxynaphthalenyl and nitrophenyl.

The divalent organic group R _27, such as methane, ethane, propane, isopropane, dimethyl methane, butane, cyclopropane, cyclobutane, cyclopentane, cyclohexane, methylcyclohexane, norbornane, adamantane, isopropylidene cyclohexane, methoxymethane , Methoxyethane, ethoxyethane, methoxyethoxymethane, benzoxymethane, tetrahydrofuran, benzene, toluene, cumene, diphenylmethane, xylene, 9,10-dihydroanthracene, mesitylene, hexamethylbenzene, biphenyl, terphenyl, triphenylbenzene, Quarterphenyl, dimethylbiphenyl, azulene, naphthalene, methylnaphthalene, anthracene, fluorene, fluorobenzene, fluorobiphenyl Divalent organic groups corresponding to benzene, isopropylidenebiphenyl, tetrafluoroisopropylidenebiphenyl, anisole, benzylphenyl ether, phenyl ether, phenoxytoluene, tolyl ether, methoxybiphenyl, dimethoxybiphenyl, methoxynaphthalene, dimethoxynaphthalene, nitrobenzene, etc. For example, there is a structure in which two hydrogen atom portions are removed from each structure to form bonds. Moreover, it is not necessarily limited to what was mentioned here.

Examples of the acidic functional group and / or derivative group thereof at the terminal part of the component (a) include groups represented by -COOR ₁ or -OR ₂ in the formula (I).

The component (a) is preferably a polymer that is soluble in an alkaline aqueous solution.
The alkaline aqueous solution is, for example, an alkaline aqueous solution such as a tetramethylammonium hydroxide aqueous solution, a metal hydroxide aqueous solution, or an organic amine aqueous solution. In general, since an aqueous tetrabutylammonium solution having a concentration of 2.38% by weight is used, the component (a) is more preferably soluble in this aqueous solution.

The molecular weight of the component (a) is not particularly limited, but is a weight average molecular weight in terms of standard polystyrene, and preferably 5,000 to 80,000.
The molecular weight can be measured by a gel permeation chromatography (GPC) method and calculated using a standard polystyrene calibration curve.

  As the component (a), for example, tetracarboxylic dianhydride, dicarboxylic acid, a compound further having an acid functional group or a derivative thereof, and a diamine or a compound further having an acid functional group are mainly used in the polymer. Preferred examples include a polyimide precursor, a polybenzoxazole precursor, a copolymer thereof, and a mixture thereof obtained as a raw material.

The component (a) can be prepared by polymerizing a tetracarboxylic dianhydride, a dicarboxylic acid and / or a dicarboxylic acid having an acid functional group and a diamine and / or a diamine having an acid functional group.
For example, the polyimide precursor which is a component (a) can be prepared by polymerizing a tetracarboxylic dianhydride and a diamine and / or a diamine having an acid functional group. Similarly, a polybenzoxazole precursor as component (a) can be prepared by polymerizing an activated esterified dicarboxylic acid and / or a dicarboxylic acid having an acid functional group and a diamine having a phenolic acid functional group. Moreover, it is (a) component by copolymerizing tetracarboxylic dianhydride, dicarboxylic acid and / or dicarboxylic acid having an active esterified acid functional group and diamine and / or diamine having an acid functional group. A copolymer of polyimide / polybenzoxazole precursor can be prepared.

  The component (b) used in the present invention is blended for the purpose of functioning as a dissolution inhibitor of the component (a) in the aqueous alkali solution, that is, a compound having an effect of inhibiting dissolution. By using the component (b) in combination with the component (c), the sensitivity of the composition of the present invention can be increased, and the dissolution rate of the unexposed area when developing with an alkaline aqueous solution is reduced. The solubility difference between the portion and the unexposed portion increases, and an excellent pattern can be formed.

式中、Ｒ_３〜Ｒ_６はそれぞれ１価の有機基である。Ｘは酸素原子又は２価の有機基である。Ｙ⁻は対アニオンである。Ｚ_１は３価の有機基である。Ｚ_２は４価の有機基である。ｎは１以上の整数であり、好ましくは１〜３の整数である。
Ｒ_３〜Ｒ_６は、好ましくはそれぞれ芳香族基、ヘテロ環基、アルキニル基、アルケニル基から選択される１つである。
Ｘは、好ましくは芳香族基、アルキニル基、アルケニル基であり、より好ましくは芳香族基である。
Ｚ_１は、好ましくはベンゼン環である。
Ｚ_２は、好ましくはベンゼン環である。
Ｙ⁻は、好ましくは硝酸イオン、テトラフロロボラートアニオン、ｐ−トルエンスルホン酸イオン、トリフラートアニオンであり、より好ましくはトリフラートアニオン（ＯＴｆ⁻）である。 The component (b) is an iodonium compound having two or more iodonium structures in one molecule, and preferably an iodonium salt having a structure represented by the formula (II), (III) or (IV).

In the formula, each of R _{3 to} R ₆ is a monovalent organic group. X is an oxygen atom or a divalent organic group. Y ⁻ is a counter anion. Z ₁ is a trivalent organic group. Z ₂ is a tetravalent organic group. n is an integer greater than or equal to 1, Preferably it is an integer of 1-3.
R _{3 to} R ₆ are preferably each selected from an aromatic group, a heterocyclic group, an alkynyl group, and an alkenyl group.
X is preferably an aromatic group, an alkynyl group, or an alkenyl group, and more preferably an aromatic group.
Z ₁ is preferably a benzene ring.
Z ₂ is preferably a benzene ring.
Y ⁻ is preferably a nitrate ion, a tetrafluoroborate anion, a p-toluenesulfonate ion, or a triflate anion, and more preferably a triflate anion (OTf ⁻ ).

  In the present invention, the iodonium structure refers to a structure having a trivalent iodine atom. (B) One molecule of the component preferably has 2 or more and 4 or less, more preferably two iodonium structures.

  The component (b) is considered to form a weak intermolecular bond with the acid functional group of the component (a) and inhibit the dissolution of the component (a) in the developer. The component (b) has a benzene ring and has a polycyclic structure such as a naphthalene ring and an anthracene ring as a component that does not absorb ultraviolet rays, particularly i-line, in order not to lower the effect of the component (c). None is preferred.

式中、Ｒ_３、Ｒ_４、Ｘ、Ｙ⁻は上記式（II）と同じである。 The component (b) is more preferably represented by the following formula (V).

In the formula, R ₃ , R ₄ , X and Y ⁻ are the same as those in the above formula (II).

式中、Ｒ_７〜Ｒ_２２はそれぞれアルキル基、アルコキシ基、パーフロロアルキル基、ハロゲン原子又は水素原子である。 X in the formula (V) is preferably one selected from the group of groups represented by the following formula (VI).

In the formula, R _{7 to} R ₂₂ are each an alkyl group, an alkoxy group, a perfluoroalkyl group, a halogen atom, or a hydrogen atom.

式中、ｍは０〜５の整数である。Ｒ_２３はそれぞれアルキル基、アルコキシ基、パーフロロアルキル基、ハロゲン原子又は水素原子である。 R ₃ and R _{4 in} the formula (V) are preferably one selected from an aromatic group, a heterocyclic group, an alkynyl group, and an alkenyl group, and more preferably a substituent represented by the following formula (VII). is there.

In formula, m is an integer of 0-5. R ₂₃ represents an alkyl group, an alkoxy group, a perfluoroalkyl group, a halogen atom or a hydrogen atom, respectively.

  Examples of the component (b) include oxobis (phenyliodonium) ditosylate, phenyl (4-tolyliodonioxy) iodonium ditosylate, (4-methoxyphenyl) (phenyliodonioxy) iodonium ditosylate, (4-tert -Butylphenyl) (phenyliodonioxy) iodonium ditosylate, 1,4-phenylenebis (phenyliodonium) ditosylate, phenyl (4- (4-tolyliodono) phenyl) iodonium ditosylate, (4-methoxyphenyl) ) (4- (phenyliodonio) phenyl) iodonium ditosylate, (4-tert-butylphenyl) (4- (phenyliodonio) phenyl) iodonium ditosylate, phenyl (4-((4-tridecylphenyl) Iodnio) Phenyl) iodonium ditosylate, (4- (cyanomethyl) phenyl) (4- (phenyliodonio) phenyl) iodonium ditosylate, ethylene-1,2-diylbis (phenyliodonium) ditosylate, ethylene-1,2-diylbis (4-iodonium) ditosylate, ethylene-1,2-diylbis ((4-methoxyphenyl) iodonium) ditosylate, phenyl ((4-tolyliodonio) ethynyl) iodonium ditosylate, phenyl ((4-methoxyphenyl) ethynyl ) Iodonium ditosylate, bicyclo [2.2.1] hepta-2,5-diene-2,3-diylbis (phenyliodonium) ditosylate, bicyclo [2.2.1] hepta-2,5-diene-2 , 3-Diylbis (4-tolyliodo Um) ditosylate, bicyclo [2.2.1] hepta-2,5-diene-2,3-diylbis (4-methoxyphenyliodonium) ditosylate, phenyl (3- (4-tolyliodonio) bicyclo [2.2 .1] Hepta-2,5-dien-2-yl) iodonium ditosylate, phenyl (3- (4-methoxyphenyliodonio) bicyclo [2.2.1] hepta-2,5-dien-2- Yl) iodonium ditosylate, oxobis (phenyliodonium) ditriflate, phenyl (4-tolyliodonioxy) iodonium ditriflate, (4-methoxyphenyl) (phenyliodonioxy) iodonium ditriflate, (4-tert-butyl) Phenyl) (phenyliodonioxy) iodonium ditriflate, 1 4-phenylenebis (phenyliodonium) ditriflate, phenyl (4- (4-tolyliodonio) phenyl) iodonium ditriflate, (4-methoxyphenyl) (4- (phenyliodonio) phenyl) iodonium ditriflate, (4 -Tert-butylphenyl) (4- (phenyliodonio) phenyl) iodonium ditriflate, phenyl (4-((4-tridecylphenyl) iodonio) phenyl) iodonium ditriflate, (4- (cyanomethyl) phenyl) (4 -(Phenyliodonio) phenyl) iodonium ditriflate, ethylene-1,2-diylbis (phenyliodonium) ditriflate, ethylene-1,2-diylbis (4-iodonium) ditriflate, ethylene-1,2-dii Rubis ((4-methoxyphenyl) iodonium) ditriflate, phenyl ((4-tolyliodonio) ethynyl) iodonium ditriflate, phenyl ((4-methoxyphenyl) ethynyl) iodonium ditriflate, bicyclo [2.2.1] Hepta-2,5-diene-2,3-diylbis (phenyliodonium) ditriflate, bicyclo [2.2.1] hepta-2,5-diene-2,3-diylbis (4-tolyliodonium) ditriflate, Bicyclo [2.2.1] hepta-2,5-diene-2,3-diylbis (4-methoxyphenyliodonium) ditriflate, phenyl (3- (4-tolyliodonio) bicyclo [2.2.1] Hepta-2,5-dien-2-yl) iodonium ditriflate, phenyl (3 (4-Methoxyphenyliodonio) bicyclo [2.2.1] hepta-2,5-dien-2-yl) iodonium ditriflate, 4,4′-oxybis (1,4-phenylene) bis ((4- (Phenyliodonio) phenyl) iodonium tetratriflate, oxobis (phenyliodonium) dinitrate, phenyl (4-tolyliodonioxy) iodonium dinitrate, (4-methoxyphenyl) (phenyliodonioxy) iodonium dinitrate, (4- tert-butylphenyl) (phenyliodonioxy) iodonium dinitrate, 1,4-phenylenebis (phenyliodonium) dinitrate, phenyl (4- (4-tolyliodonio) phenyl) iodonium dinitrate, (4-methoxyphenyl) 4- (phenyliodonio) phenyl) iodonium dinitrate, (4-tert-butylphenyl) (4- (phenyliodonio) phenyl) iodonium dinitrate, phenyl (4-((4-tridecylphenyl) iodonio) phenyl ) Iodonium dinitrate, (4- (cyanomethyl) phenyl) (4- (phenyliodonio) phenyl) iodonium dinitrate, ethylene-1,2-diylbis (phenyliodonium) dinitrate, ethylene-1,2-diylbis (4- Iodonium) dinitrate, ethylene-1,2-diylbis ((4-methoxyphenyl) iodonium) dinitrate, phenyl ((4-tolyliodonio) ethynyl) iodonium dinitrate, phenyl ((4-methoxyphenyl) ethynyl ) Iodonium dinitrate, bicyclo [2.2.1] hepta-2,5-diene-2,3-diylbis (phenyliodonium) dinitrate, bicyclo [2.2.1] hepta-2,5-diene-2, 3-diylbis (4-tolyliodonium) dinitrate, bicyclo [2.2.1] hepta-2,5-diene-2,3-diylbis (4-methoxyphenyliodonium) dinitrate, phenyl (3- (4-tolyliodo) Nio) bicyclo [2.2.1] hepta-2,5-dien-2-yl) iodonium dinitrate, phenyl (3- (4-methoxyphenyliodonio) bicyclo [2.2.1] hepta-2, 5-dien-2-yl) iodonium dinitrate, oxobis (phenyliodonium) ditetrafluoroborate, phenyl ( -Tolyliodonioxy) iodonium ditetrafluoroborate, (4-methoxyphenyl) (phenyliodonioxy) iodonium ditetrafluoroborate, (4-tert-butylphenyl) (phenyliodonioxy) iodonium ditetrafluoro Lobolate, 1,4-phenylenebis (phenyliodonium) ditetrafluoroborate, phenyl (4- (4-tolyliodonio) phenyl) iodonium ditetrafluoroborate, (4-methoxyphenyl) (4- (phenyl Iodonio) phenyl) iodonium ditetrafluoroborate, (4-tert-butylphenyl) (4- (phenyliodonio) phenyl) iodonium ditetrafluoroborate, phenyl (4-((4-tridecylphenyl) iodonio ) Phenyl) Yo Donium ditetrafluoroborate, (4- (cyanomethyl) phenyl) (4- (phenyliodonio) phenyl) iodonium ditetrafluoroborate, ethylene-1,2-diylbis (phenyliodonium) ditetrafluoroborate, Ethylene-1,2-diylbis (4-iodonium) ditetrafluoroborate, ethylene-1,2-diylbis ((4-methoxyphenyl) iodonium) ditetrafluoroborate, phenyl ((4-tolyliodonio) ethynyl ) Iodonium ditetrafluoroborate, phenyl ((4-methoxyphenyl) ethynyl) iodonium ditetrafluoroborate, bicyclo [2.2.1] hepta-2,5-diene-2,3-diylbis (phenyliodonium) Ditetrafluoroborate, bicyclo [2.2 .1] Hepta-2,5-diene-2,3-diylbis (4-tolyliodonium) ditetrafluoroborate, bicyclo [2.2.1] hepta-2,5-diene-2,3-diylbis ( 4-methoxyphenyliodonium) ditetrafluoroborate, phenyl (3- (4-tolyliodonio) bicyclo [2.2.1] hepta-2,5-dien-2-yl) iodonium ditetrafluoroborate, Phenyl (3- (4-methoxyphenyliodonio) bicyclo [2.2.1] hepta-2,5-dien-2-yl) iodonium ditetrafluoroborate, oxobis (phenyliodonium) disulfonate, phenyl (4- Tolyliodonioxy) iodonium disulfonate, (4-methoxyphenyl) (phenyliodonioxy) iodonium Disulfonate, (4-tert-butylphenyl) (phenyliodonioxy) iodonium disulfonate, 1,4-phenylenebis (phenyliodonium) disulfonate, phenyl (4- (4-tolyliodonio) phenyl) iodonium disulfonate , (4-methoxyphenyl) (4- (phenyliodonio) phenyl) iodonium disulfonate, (4-tert-butylphenyl) (4- (phenyliodonio) phenyl) iodonium disulfonate, phenyl (4- ( (4-Tridecylphenyl) iodonio) phenyl) iodonium disulfonate, (4- (cyanomethyl) phenyl) (4- (phenyliodonio) phenyl) iodonium disulfonate, ethylene-1,2-diylbis (phenyliodoni) ) Disulfonate, ethylene-1,2-diylbis (4-iodonium) disulfonate, ethylene-1,2-diylbis ((4-methoxyphenyl) iodonium) disulfonate, phenyl ((4-tolyliodonio) ethynyl) iodonium disulfone Narate, phenyl ((4-methoxyphenyl) ethynyl) iodonium disulfonate, bicyclo [2.2.1] hepta-2,5-diene-2,3-diylbis (phenyliodonium) disulfonate, bicyclo [2.2. 1] Hepta-2,5-diene-2,3-diylbis (4-tolyliodonium) disulfonate, bicyclo [2.2.1] hepta-2,5-diene-2,3-diylbis (4-methoxyphenyliodonium ) Disulfonate, phenyl (3- (4-tolylyo) Donio) bicyclo [2.2.1] hepta-2,5-dien-2-yl) iodonium disulfonate, phenyl (3- (4-methoxyphenyliodonio) bicyclo [2.2.1] hepta-2 , 5-Dien-2-yl) iodonium disulfonate and the like. Moreover, it is not necessarily limited to what was mentioned here.

  The naphthoquinone diazide compound (c) is a photosensitizer and has a function of generating an acid upon irradiation with actinic light. By including the component (c), it is possible to increase the solubility of the resin film obtained from the composition of the present invention in the alkaline aqueous solution at the portion irradiated with light. The naphthoquinone diazide compound is preferably an o-naphthoquinone diazide compound.

  The naphthoquinonediazide compound can be obtained, for example, by subjecting a naphthoquinonediazidosulfenyl chloride and a polyhydroxy compound to a condensation reaction according to a conventional method, for example, a polyhydroxy compound and 1,2-naphthoquinonediazide-4-sulfonyl chloride, or 1, It can be obtained by reacting 2-naphthoquinonediazide-5-sulfonyl chloride in the presence of a basic catalyst such as triethylamine.

  Examples of the polyhydroxy compounds that serve as ballasts for the photosensitizer include hydroquinone, resorcinol, pyrogallol, bisphenol A, bis (2-hydroxyphenyl) methane, bis (4-hydroxyphenyl) methane, and 2-hydroxyphenyl-4′-hydroxyphenyl. Methane, 2,2-bis (4-hydroxyphenyl) hexafluoropropane, 2,3,4-trihydroxybenzophenone, 2,3,4,4′-tetrahydroxybenzophenone, 2,2 ′, 4,4′- Tetrahydroxybenzophenone, 2,3,4,2 ′, 3′-pentahydroxybenzophenone, 2,3,4,3 ′, 4 ′, 5′-hexahydroxybenzophenone, bis (2,3,4-trihydroxyphenyl) ) Methane, bis (2,3,4-trihydroxyphenyl) Lopan, 2- (4-hydroxyphenyl) -2- [4- [1,1-bis (4-hydroxyphenyl) ethyl] phenyl] propane, 4b, 5,9b, 10-tetrahydro-1,3,6 Examples include 8-tetrahydroxy-5,10-dimethylindeno [2,1-a] indene, tris (4-hydroxyphenyl) methane, 1,1,1-tris (4-hydroxyphenyl) ethane, and the like. Moreover, it is not necessarily limited to what was mentioned here.

The solvent of component (d) dissolves the components (a), (b), and (c) described above to make the composition varnished.
Solvents used include N-methyl-2-pyrrolidone, γ-butyrolactone, N, N-dimethylacetamide, dimethyl sulfoxide, 2-methoxyethanol, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether , Propylene glycol monomethyl ether acetate, methyl lactate, ethyl lactate, butyl lactate, methyl-1,3-butylene glycol acetate, 1,3-butylene glycol acetate, cyclohexanone, cyclopentanone, tetrahydrofuran and the like. May be used.

In the composition of the present invention, the amount of component (b) is preferably 0.01 to 50 parts by weight, more preferably 0.01 to 10 parts by weight with respect to 100 parts by weight of component (a). The amount of component (c) is preferably 1-50 parts by weight, more preferably 5-30 parts by weight, per 100 parts by weight of component (a). Although there is no restriction | limiting in particular in the quantity of the solvent of a component (d), 150-230 weight part is normally used with respect to 100 weight part of component (a).
In the composition of the present invention, for example, 70% by weight or more, 80% by weight or more, 90% by weight or more, and 100% by weight may comprise the components (a) to (d). In addition to these components, the composition of the present invention may contain substances that do not substantially impair the basic characteristics of the present invention, such as the following additives.
The composition of the present invention may contain an adhesion-imparting agent, a surfactant or leveling agent, a crosslinking agent, etc. in addition to the components (a) to (d) described above.

  The adhesion-imparting agent can enhance the adhesion with the base of the cured film obtained from the composition of the present invention. Examples of the adhesion imparting agent include organic silane compounds and aluminum chelate compounds.

  Examples of the organic silane compound include vinyltriethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-methacryloxypropyltrimethoxysilane, ureapropyltriethoxysilane, methylphenylsilanediol, ethylphenylsilanediol, n- Propylphenylsilanediol, isopropylphenylsilanediol, n-butylphenylsilanediol, isobutylphenylsilanediol, tert-butylphenylsilanediol, diphenylsilanediol, ethylmethylphenylsilanol, n-propylmethylphenylsilanol, isopropylmethylphenylsilanol, n-butylmethylphenylsilanol, isobutylmethylphenylsilanol, tert-butylmethylphenylsilanol , Ethyl n-propylphenylsilanol, ethylisopropylphenylsilanol, n-butylethylphenylsilanol, isobutylethylphenylsilanol, tert-butylethylphenylsilanol, methyldiphenylsilanol, ethyldiphenylsilanol, n-propyldiphenylsilanol, isopropyldiphenylsilanol , N-butyldiphenylsilanol, isobutyldiphenylsilanol, tert-butyldiphenylsilanol, phenylsilanetriol, 1,4-bis (trihydroxysyl) benzene, 1,4-bis (methyldihydroxysilyl) benzene, 1,4-bis (Ethyldihydroxysilyl) benzene, 1,4-bis (propyldihydroxysilyl) benzene, 1,4-bis (butyldihi Loxysilyl) benzene, 1,4-bis (dimethylhydroxysilyl) benzene, 1,4-bis (diethylhydroxysilyl) benzene, 1,4-bis (dipropylhydroxysilyl) benzene, 1,4-bis (dibutylhydroxysilyl) ) Benzene and the like.

  Examples of the aluminum chelate compound include tris (acetylacetonate) aluminum and acetylacetate aluminum diisopropylate.

  The content of the adhesion-imparting agent is preferably 0.01 to 20 parts by weight, more preferably 0.1 to 10 parts by weight with respect to 100 parts by weight of component (a).

The surfactant or the leveling agent can prevent, for example, striation (film thickness unevenness) or improve the developability of the composition of the present invention.
Examples of the surfactant or leveling agent include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, and the like.
Commercially available surfactants or leveling agents include Megafac F171, F173, R-08 (Dainippon Ink Chemical Co., Ltd.), Florard FC430, FC431 (Sumitomo 3M Limited), organosiloxane polymer KP341. , KBM303, KBM403, KBM803 (manufactured by Shin-Etsu Chemical Co., Ltd.) and the like.

The crosslinking agent can improve the stretchability, elastic modulus, and thermal characteristics of the thermosetting film obtained from the composition of the present invention.
The crosslinking agent is, for example, a methylol compound, and examples of the methylol compound include 3,3′-methylenebis (2-hydroxy-5-methylbenzenemethanol), 4,4 ′-(1-methylethylidene) bis [2 -Methyl-6-hydroxymethylphenol], 4,4 '-(1,1,1,3,3,3-hexafluoroisopropylidene) bis [2,6-bis (hydroxymethyl) phenol], 3,3 ', 5,5'-tetrakis (hydroxymethyl) [(1,1'-biphenyl) -4,4'-diol], 4,4'-(1-methylethylidene) bis [2,6-bis (hydroxy Methyl) phenol], 2,2′-methylenebis (4,6-bishydroxymethylphenol), 2,6-bis [(2-hydroxy-3-hydroxymethyl-5-methylpheny) ) Include methyl] -4-methylphenol and the like. Moreover, it is not necessarily limited to what was mentioned here.

Next, the manufacturing method of the pattern cured film of this invention is demonstrated.
A pattern cured film can be formed using the composition of the present invention. In particular, the cured film obtained from the composition of the present invention is excellent in heat resistance and mechanical properties.

  The pattern cured film manufacturing method of the present invention includes a photosensitive resin film forming step in which the composition of the present invention is applied to a support substrate and dried to form a photosensitive resin film, and the formed photosensitive resin film is predetermined. An exposure process for exposing the pattern, a development process for developing the exposed photosensitive resin film using an alkaline aqueous solution to obtain a pattern resin film, and a heat treatment process for obtaining a pattern cured film by heat-treating the pattern resin film including.

Examples of the support substrate to which the composition of the present invention is applied include a silicon wafer, a metal substrate, and a ceramic substrate. Examples of the coating method include a dipping method, a spray method, a screen printing method, and a spin coating method.
A photosensitive resin coating film is obtained by appropriately heating and drying the composition of the present invention applied on a support substrate.

On the obtained photosensitive resin coating film, the exposure process which irradiates actinic light or actinic radiation through the mask in which the desired pattern was drawn is performed.
As the actinic ray or actinic ray to be irradiated, a contact / proximity exposure machine using an ultra-high pressure mercury lamp, a mirror projection exposure machine, an i-line stepper, a g-line stepper, other ultraviolet rays, a visible light source, an X-ray or an electron beam is used. be able to.
After the exposure, a post-exposure bake (PEB) treatment may be performed as necessary.

A desired positive pattern (pattern resin film) can be obtained by dissolving and removing the exposed portion of the exposed resin film using an alkaline aqueous solution.
Examples of the alkaline aqueous solution as a developer include aqueous solutions of alkali metal hydroxides such as caustic potash and caustic soda; quaternary ammonium hydroxides such as tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline; ethanolamine, propylamine and ethylenediamine. An aqueous amine solution such as can be used.

  After development, it may be rinsed with water or a poor solvent as necessary. Examples of the rinsing liquid to be used include methanol, ethanol, isopropyl alcohol, benzene, toluene, xylene, methyl cellosolve, and water.

By heating the obtained pattern resin film, the solvent or the solvent and the photosensitizer can be removed to obtain a stable high heat resistant pattern cured film.
The said heating temperature becomes like this. Preferably it is 150-500 degreeC, More preferably, it is 200-400 degreeC. When the heating temperature is less than 150 ° C., the mechanical properties and thermal properties of the film may be deteriorated. On the other hand, when the heating temperature exceeds 500 ° C., the mechanical properties and thermal properties of the film may be deteriorated.
The heating time is preferably 0.05 to 10 hours. When the heating time is less than 0.05 hours, the mechanical properties and thermal properties of the film may be deteriorated. On the other hand, when the heating time exceeds 10 hours, the mechanical properties and thermal properties of the film may be deteriorated.

The electronic component of the present invention has the above cured film. Here, the electronic component includes a semiconductor device, a multilayer wiring board, various electronic devices, and the like.
Specifically, the cured film of the present invention can be used for a surface protective film of an electronic component such as a semiconductor device, an interlayer insulating film, an interlayer insulating film of a multilayer wiring board, or the like. The electronic component of the present invention is not particularly limited except that it has a cured film provided as a surface protective film or an interlayer insulating film, and can have various structures.

  The manufacturing method of the pattern cured film of this invention and an electronic component provided with the pattern cured film of this invention are demonstrated based on drawing for an example of the manufacturing process of the semiconductor device which has a pattern cured film. 1 to 5 are schematic cross-sectional views for explaining a manufacturing process of a semiconductor device having a multilayer wiring structure, and represent a series of processes from a first process to a fifth process.

1 to 5, a semiconductor substrate 1 such as a Si substrate having a circuit element (not shown) is covered with a protective film 2 such as a silicon oxide film except for a predetermined portion of the circuit element, and on the exposed circuit element. A first conductor layer 3 is formed. An interlayer insulating film layer 4 is formed on the semiconductor substrate 1 by a spin coating method or the like (first step, FIG. 1).
The interlayer insulating film layer 4 can be formed using the resin composition of the present invention.

  Next, a photosensitive resin layer 5 such as chlorinated rubber or phenol novolac is formed on the interlayer insulating film layer 4 as a mask by a spin coating method, and a predetermined portion of the interlayer insulating film layer 4 is formed by a known photolithography technique. A window 6A is provided so as to be exposed (second step, FIG. 2).

  The interlayer insulating film layer 4 exposed to the window 6A is selectively etched by a dry etching means using a gas such as oxygen or carbon tetrafluoride to open the window 6B. Next, the photosensitive resin layer 5 is completely removed using an etching solution that corrodes only the photosensitive resin layer 5 without corroding the first conductor layer 3 exposed from the window 6B (third step, FIG. 3).

  Further, the second conductor layer 7 is formed by using a known photolithography technique, and the electrical connection with the first conductor layer 3 is completely performed (fourth step, FIG. 4). When a multilayer wiring structure having three or more layers is formed, each layer can be formed by repeating the above steps.

Next, the surface protective film 8 is formed. In FIG. 5, the resin composition of the present invention is applied and dried by a spin coating method, irradiated with light from a mask on which a pattern for forming a window 6C is formed at a predetermined portion, and then developed with an alkaline aqueous solution. A resin film is formed. Thereafter, the patterned resin film is heated to form a patterned cured film of a photosensitive resin as the surface protective film layer 8 (fifth step, FIG. 5).
This surface protective film layer (patterned cured film) 8 protects the conductor layer from external stress, α rays, etc., and the resulting semiconductor device is excellent in reliability.

Synthesis example 1
In a flask which is a closed reaction vessel equipped with a stirrer, a thermometer and a nitrogen introduction tube, 6495 g of dry N-methylpyrrolidone and 1831.3 g of 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (5 mol) ) And 218.3 g (2 mol) of m-aminophenol were added and stirred until dissolved at 15 to 25 ° C. Next, 1771 g (6 mol) of 4,4′-diphenyl ether dicarboxylic acid dichloride was added over 30 minutes, followed by stirring at 20 to 35 ° C. for 3 hours. The reaction mixture was treated with 2.0 L of ion exchange water with vigorous stirring. The precipitated solid was further washed with warm ion-exchanged water at 70 ° C., sucked and dried on a filtration filter, and further dried under reduced pressure to obtain polymer A (component (a)). This polymer A had a water content of 0.8% by weight, a weight average molecular weight of 19,200, and a dispersity of 1.5.

(Measurement conditions of weight average molecular weight by GPC method)
Measuring device: Detector SPD-M20A manufactured by Shimadzu Corporation
Pump: LC-20A manufactured by Shimadzu Corporation
System controller: CBM-20A
Measurement conditions: Column Gelpack GL-S300MDT-5 × 2 eluent: THF (tetrahydrofuran) / DMF (N, N-dimethylformamide) = 1/1 (volume ratio)
LiBr · H ₂ O (0.03 mol / L), H ₃ PO ₄ (0.06 mol / L)
Flow rate: 1.0 mL / min, detector: 190 to 800 nm (molecular weight is calculated by 270 nm chromatogram)
A sample diluted with a solution of 1 mL of solvent with respect to 0.5 mg of polymer was measured.

Synthesis example 2
50 mL of dehydrated dichloromethane (manufactured by Wako Pure Chemical Industries) and 4.40 g of iodosobenzene (manufactured by Tokyo Chemical Industry) were placed in a flask which is a closed reactor equipped with a nitrogen introduction tube and a stirrer, and stirred at 10 to 25 ° C. To this, 3.50 g of trifluoromethanesulfonic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was dropped over 20 minutes and stirred at 10 to 25 ° C. for 1 hour. To the resulting solution, 1.57 g of dehydrated benzene (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise over 20 minutes and stirred at 10 to 25 ° C. for 1 hour. The precipitate was washed with diethyl ether (manufactured by Wako Pure Chemical Industries), filtered, dried under reduced pressure, and the following iodonium salt A (1,4-phenylenebis (phenyliodonium) ditriflate) (component (b)) was colorless. Obtained with crystals.

Nuclear magnetic resonance spectrum (solvent: dimethyl sulfoxide (DMSO) -d6) was measured by nuclear magnetic resonance spectroscopy (NMR). The results are shown below.
¹ H-NMR δ 7.53 ppm (t, J = 8 Hz, 4H), 7.68 Hz (t, J = 8 Hz, 2H), 8.25 Hz (d, J = 4 Hz, 4H), 8.34 (brs, 4H) )

Synthesis example 3
Except for using dehydrated toluene in place of the dehydrated benzene of Synthesis Example 2, iodonium salt B (phenyl (4- (p-tolyliodonio) phenyl) iodonium ditriflate) (component) shown below in the same manner as Synthesis Example 2 (B)) was obtained.

Synthesis example 4
Iodonium salt C ((4-methoxyphenyl) (4- (phenyliodonio) phenyl) iodonium ditriflate) (component ( b)) was obtained.

Synthesis example 5
The iodonium salt D ((4-tert-butylphenyl) (4- (phenyliodonio) phenyl) iodonium ditriflate was the same as in Synthesis Example 2 except that tert-butylbenzene was used in place of the dehydrated benzene of Synthesis Example 2. ) (Component (b)) was obtained.

Example 1
In a three-necked flask equipped with a stirrer, a nitrogen inlet tube, and a thermometer, 170 g of γ-butyrolactone, 17 g of propylene glycol monobutyl ether acetate, 100 g of the polymer A obtained in Synthesis Example 1, 4,4 ′-(1,1,1, 1,3,3,3-hexafluoroisopropylidene) bis [2,6-bis (hydroxymethyl) phenol] 7.5 g, 2- (4-hydroxyphenyl) -2- [4- [1,1-bis 11.0 g of a compound obtained by reacting (4-hydroxyphenyl) ethyl] phenyl] propane with 6-diazo-5-oxo-5,6-dihydronaphthalene-1-sulfonyl chloride in a molar ratio of 1 / 2.5, bis (2-hydroxyethyl) -3-aminopropyltriethoxysilane (62% ethanol solution) 3.5 g, trimethoxy (phenyl) silane 0 5g, after overnight stirring and dissolved at room temperature by addition of iodonium salts A3.0G, to obtain a positive photosensitive resin composition solution was filtered.
This solution was spin-coated on a 6-inch silicon wafer and dried to form a coating film having a film thickness of 11.0 ± 1.0 μm, and then patterned using an i-line stepper, and the exposure amount was 100 to 800 mJ. / Cm ² for exposure. The exposed coating film was subjected to paddle development using a 2.38% tetramethylammonium hydroxide aqueous solution for a development time of 95%, and a good relief pattern was obtained at 550 mJ / cm ² .

Example 2
A positive photosensitive resin composition solution was prepared in the same manner as in Example 1 except that the iodonium salt B was used instead of the iodonium salt A, and a pattern resin film was produced. As a result, a good relief pattern was obtained at 550 mJ / cm ² or more when the residual film ratio was 95%.

Example 3
A positive photosensitive resin composition solution was prepared in the same manner as in Example 1 except that iodonium salt C was used instead of iodonium salt A, and a pattern resin film was produced. As a result, a good relief pattern was obtained at 550 mJ / cm ² or more when the residual film ratio was 95%.

Example 4
A positive photosensitive resin composition solution was prepared in the same manner as in Example 1 except that iodonium salt D was used instead of iodonium salt A, and a pattern resin film was produced. As a result, a good relief pattern was obtained at 550 mJ / cm ² or more when the residual film ratio was 95%.

Comparative Example 1
A positive photosensitive resin composition solution was prepared in the same manner as in Example 1 except that diphenyliodonium triflate was used in place of the iodonium salt A, and a pattern resin film was produced. As a result, when the residual film ratio was 95%, a good relief pattern was obtained at 730 mJ / cm ² or more.

Comparative Example 2
A positive photosensitive resin composition solution was prepared in the same manner as in Example 1 except that (4-methoxyphenyl) phenyliodonium triflate was used in place of the iodonium salt A, and a pattern resin film was produced. As a result, a good relief pattern was obtained at 750 mJ / cm ² or more when the residual film ratio was 95%.

  From the results of Examples and Comparative Examples, the positive photosensitive resin composition of the present invention can form a good pattern with a low exposure even at a high residual film ratio, and is a highly sensitive positive photosensitive resin composition. I understand that there is.

  The positive photosensitive resin composition of the present invention can be used as a material for a pattern cured film that becomes a surface protective film or an interlayer insulating film of an electronic component.

DESCRIPTION OF SYMBOLS 1 Semiconductor substrate 2 Protective film 3 1st conductor layer 4 Interlayer insulating film layer 5 Photosensitive resin layer 6A, 6B, 6C Window 7 2nd conductor layer 8 Surface protective film layer

Claims (11)

(A) a polymer having a phenolic hydroxyl group or a carboxy group;
(B) an iodonium compound having two or more iodonium structures in one molecule;
(C) A positive photosensitive resin composition containing a diazonaphthoquinone compound, and (d) a solvent. The positive photosensitive resin composition according to claim 1, wherein the component (a) is a polymer having a structure represented by the following formula (I).

(In the formula, X ₁ is a divalent to octavalent organic group. Y ₁ is a divalent to octavalent organic group. R ₁ is a hydrogen atom or an organic group having 1 to 20 carbon atoms. R _2. Are each a hydrogen atom or a monovalent organic group, p and q are each an integer of 0 to 4. l and m are each an integer of 0 to 2. l + m + p + q is 1 or more, and n is a polymer. (It is an integer of 2 or more indicating the number of structural units in it.) The positive photosensitive resin composition according to claim 1 or 2, wherein the component (b) is at least one selected from the group of compounds represented by the following formulas (II), (III) and (IV). .

(In the formula, R _{3 to} R ₆ are each a monovalent organic group. X is an oxygen atom or a divalent organic group. Y ⁻ is a counter anion. Z ₁ is a trivalent organic group. Z ₂ is a tetravalent organic group, and n is an integer of 1 or more.) The positive photosensitive resin composition according to claim 1, wherein the component (b) has a structure represented by the following formula (V).

(Wherein R ₃ and R ₄ are each a monovalent organic group. X is an oxygen atom or a divalent organic group. Y ⁻ is a counter anion.) The positive photosensitive resin composition according to claim 4, wherein X in the formula (V) is one selected from the group of groups represented by the following formula (VI).

(In formula, R < ₇ > -R < ₂₂ > is an alkyl group, an alkoxy group, a perfluoroalkyl group, a halogen atom, or a hydrogen atom respectively. Moreover, it may become a ring structure by mutually bonding.) The positive photosensitive resin composition according to claim 4 or 5, wherein R ₃ and R _{4 in} the formula (V) are each selected from an aromatic group, a heterocyclic group, an alkynyl group, and an alkenyl group. The positive photosensitive resin composition according to any one of claims 4 to 6, wherein R ₃ and R _{4 in} the formula (V) are groups each represented by the following formula (VII).

(In the formula, m is an integer of 0 to 5. R ₂₃ is an alkyl group, an alkoxy group, a perfluoroalkyl group, a halogen atom or a hydrogen atom, respectively.)   The positive photosensitive resin according to any one of claims 1 to 7, comprising 0.01 to 50 parts by weight of component (b) and 1 to 50 parts by weight of component (c) with respect to 100 parts by weight of component (a). Resin composition.   A cured film obtained by curing the positive photosensitive resin composition according to claim 1.   Applying and drying the positive photosensitive resin composition according to any one of claims 1 to 8 on a support substrate to form a photosensitive resin film, exposing the photosensitive resin film, and A method for producing a patterned cured film, comprising: a step of developing a photosensitive resin film after exposure using an alkaline aqueous solution to obtain a pattern resin film; and a step of heat-treating the pattern resin film to obtain a patterned cured film.   An electronic component in which the cured film according to claim 9 is provided as an interlayer insulating film layer or a surface protective film layer.

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