JP2020166124A - Photosensitive resin composition, cured film, method for producing cured film, and display device - Google Patents

Abstract

To provide a photosensitive resin composition which exhibits excellent photosensitive characteristics.SOLUTION: The photosensitive resin composition contains (a) an alkali-soluble resin, (b) a naphthoquinonediazide esterified product, (c) a phenol compound having 3-7 benzene rings, and (d) an organic solvent. The compound (c) is contained in an amount of 10 pts.mass or more and 30 pts.mass or less based on 100 pts.mass of the alkali-soluble resin (a).SELECTED DRAWING: None

Description

The present invention relates to a photosensitive resin composition. More specifically, a surface protective film or interlayer insulating film of a semiconductor element, an insulating film of an organic electroluminescence (hereinafter referred to as EL) element, and a thin film transistor (hereinafter referred to as TFT) for driving a display device using an organic EL element. The present invention relates to a photosensitive resin composition suitable for applications such as a substrate flattening film, a circuit substrate wiring protective insulating film, an on-chip microlens of a solid-state imaging device, and a flattening film for various displays and solid-state imaging devices.

Resins typified by polyimide and polybenzoxazole have excellent heat resistance and electrical insulation, so that they can be used as surface protective films for semiconductor devices such as LSIs (Large Scale Integration Curricuit), interlayer insulating films, and insulating layers for organic EL devices. It is used as a flattening film for TFT substrates.

In such applications, finely processable positive photosensitive resin compositions that dissolve by alkaline development are used, and these positive photosensitive resin compositions include naphthoquinone diazide in a soluble polyimide having a hydroxyl group. (See Patent Document 1), a polyimide precursor and a naphthoquinone diazide compound to which a compound having a phenolic hydroxyl group having a specific structure is added (see Patent Document 2), an aromatic hydroxy compound and aldehydes or A positive polyimide composition obtained by adding an alkali-soluble resin such as a condensation reaction product with ketones, polyhydroxystyrene and its derivative, and a compound having a phenolic hydroxyl group having a specific structure to a quinonediazide esterified product (Patent Document 3, Patent Document 3, 4) and the like are known.

JP-A-64-60630 Japanese Unexamined Patent Publication No. 2001-64507 JP-A-11-352680 Japanese Unexamined Patent Publication No. 2004-361637

The compositions described in Patent Documents 1 to 3 have a problem in achieving both high sensitivity and suppression of film slippage during development.

An object of the present invention is to provide a photosensitive resin composition capable of suppressing film burr during development while having high sensitivity. That is, the present invention
(A) Alkali-soluble resin and
(B) Naftquinone diazide esterified product and
(C) The compound represented by the general formula (I) and
(D) A photosensitive resin composition containing an organic solvent.
The x of the general formula (I) is 1 with respect to 100% of the total area of the peak detected at the detector wavelength of 254 nm by the liquid chromatography method of the compound represented by the general formula (I) (c). The area of the peak for the compound is 80-92%, the area of the peak for the compound where x is 3 is 7 to 15%, and the area of the peak for the compound where x is 5 is 1-5%. Moreover, the compound represented by the general formula (I) is (a) a photosensitive resin composition containing 10 parts by mass or more and 30 parts by mass or less with respect to 100 parts by mass of an alkali-soluble resin.

In the formula, R ⁴ , R ⁵ , R ⁷ , and R ⁸ independently have a hydroxyl group, a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a carboxyl group, and 1 to 4 carbon atoms. Indicates one of the ester groups of. R ⁶ represents a hydroxyl group, a hydrogen atom, an alkyl group selected from 1 to 7 carbon atoms, or a hydroxybenzyl group, and at least one R ⁶ is a hydroxyl group. The plurality of R ⁴ , R ⁵ , and R ⁶ may be the same or different. x represents an integer of 1-5.

According to the present invention, it is possible to obtain a photosensitive resin composition capable of suppressing film burr during development while having high sensitivity.

The photosensitive resin composition of the present invention is
(A) Alkali-soluble resin and
(B) Naftquinone diazide esterified product and
(C) The compound represented by the general formula (I) and
(D) A photosensitive resin composition containing an organic solvent.
The x of the general formula (I) is 1 with respect to 100% of the total area of the peak detected at the detector wavelength of 254 nm by the liquid chromatography method of the compound represented by the general formula (I) (c). The area of the peak for the compound is 80-92%, the area of the peak for the compound where x is 3 is 7 to 15%, and the area of the peak for the compound where x is 5 is 1-5%. A photosensitive resin composition containing 10 parts by mass or more and 30 parts by mass or less of the compound represented by the general formula (I) with respect to 100 parts by mass of (a) alkali-soluble resin.

In the formula, R ⁴ , R ⁵ , R ⁷ , and R ⁸ independently have a hydroxyl group, a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a carboxyl group, and 1 to 4 carbon atoms. Indicates one of the ester groups of. R ⁶ represents a hydroxyl group, a hydrogen atom, an alkyl group selected from 1 to 7 carbon atoms, or a hydroxybenzyl group, and at least one R ⁶ is a hydroxyl group. The plurality of R ⁴ , R ⁵ , and R ⁶ may be the same or different. x represents an integer of 1-5.

The photosensitive resin composition of the present invention contains (a) an alkali-soluble resin.
Examples of the alkali-soluble resin include polyimide, polybenzoxazole, and precursors thereof, a radically polymerizable polymer having acrylic acid, a phenol-novolac resin, polyhydroxystyrene, and polysiloxane. Further, the alkali solubility may be adjusted by protecting the acidic groups of these resins.

The alkali-soluble resin refers to a resin having an acidic group that is soluble in alkali, and such a resin includes choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, and water in addition to tetramethylammonium hydroxide. It dissolves in an alkaline aqueous solution such as sodium oxide, potassium hydroxide, and sodium carbonate. Two or more of these resins may be contained.

Among them, from the viewpoint of chemical resistance, polyimide, polybenzoxazole and / or a precursor thereof are preferable, and polyimide and / or a polyimide precursor is more preferable. The polyimide precursor undergoes an imidization reaction in which the amic acid moiety is closed by firing at about 200 ° C., and the polybenzoxazole precursor undergoes an oxazoleization reaction in which the hydroxyamide moiety is closed by firing at about 300 ° C., resulting in volume shrinkage. Has the property of The photosensitive resin composition using these precursor resins can obtain a forward-tapered pattern by heating when obtaining a cured film after obtaining a fine pattern by an exposure / developing step. This forward taper shape pattern is excellent in coating properties of the upper electrode when used as an insulating film of an organic EL element, can prevent disconnection, and can improve the reliability of the element.

Polyimide and polybenzoxazole are resins having a cyclic structure of an imide ring or an oxazole ring in the main chain structure. The weight average molecular weight is preferably 5,000 to 500,000, more preferably 10,000 to 100,000, and even more preferably 15,000 to 400,000.

Polyimide can be obtained by reacting a tetracarboxylic acid, a corresponding tetracarboxylic dianhydride, a tetracarboxylic dianester dichloride, or the like with a diamine, a diisocyanate compound, or a trimethylsilylated diamine, and the tetracarboxylic acid residue and the diamine residue can be obtained. Has a group. For example, it can be obtained by dehydrating and closing the ring of polyamic acid, which is one of the polyimide precursors obtained by reacting tetracarboxylic dianhydride with diamine, by heat treatment. Alternatively, it can also be obtained by adding a dehydration condensing agent such as carboxylic acid anhydride or dicyclohexylcarbodiimide or a base such as triethylamine as a ring-closing catalyst, and dehydrating and ring-closing by chemical heat treatment. Alternatively, it can also be obtained by adding a weakly acidic carboxylic acid compound and dehydrating and ring-closing by heat treatment at a low temperature of 100 ° C. or lower.

Polybenzoxazole can be obtained by reacting a bisaminophenol compound with a dicarboxylic acid, a dicarboxylic acid chloride, a dicarboxylic acid active ester, or the like, and has a dicarboxylic acid residue and a bisaminophenol residue. For example, it can be obtained by dehydrating and closing the ring of polyhydroxyamide, which is one of the polybenzoxazole precursors obtained by reacting a bisaminophenol compound with a dicarboxylic acid, by heat treatment. Alternatively, it can be obtained by adding anhydrous phosphoric acid, a base, a carbodiimide compound, or the like and dehydrating and closing the ring by chemical treatment.

The polyimide precursor and the polybenzoxazole precursor are resins having an amide bond in the main chain, and are dehydrated and closed by heat treatment or chemical treatment to obtain the above-mentioned polyimide or polybenzoxazole. The weight average molecular weight is preferably 5,000 to 500,000, more preferably 10,000 to 100,000, and even more preferably 15,000 to 400,000. Examples of the polyimide precursor include polyamic acid, polyamic acid ester, polyamic acid amide, polyisoimide and the like, and polyamic acid and polyamic acid ester are preferable. Examples of the polybenzoxazole precursor include polyhydroxyamide, polyaminoamide, polyamide, polyamideimide and the like, and polyhydroxyamide is preferable.

Polyimides, polybenzoxazoles, and their precursors have OR ²⁷ , SO ₃ R ²⁷ , CONR ²⁷ R ²⁸ , COOR ²⁷ , SO ₂ NR ^{27 in} acid or diamine residues from the standpoint of solubility in aqueous alkaline solutions. It preferably has an acidic group such as R ²⁸ or an acidic group derivative, and more preferably has a hydroxyl group. R ²⁷ and R ²⁸ represent hydrogen atoms or monovalent organic groups having 1 to 20 carbon atoms, which may be the same or different. The acidic group refers to the case where R ²⁷ and R ²⁸ are all hydrogen atoms, and the acidic group derivative refers to the case where R ²⁷ or R ²⁸ contains a monovalent organic group having 1 to 20 carbon atoms. Examples of the organic group include an alkyl group, an alkoxyl group and an ester group.

Preferred structures of the tetracarboxylic acid residue of polyimide and the polyimide precursor and the dicarboxylic acid residue of polybenzoxazole and the polybenzoxazole precursor include the following structures and some of these hydrogen atoms having 1 to 1 carbon atoms. Examples thereof include a structure in which 1 to 4 are substituted with 20 alkyl groups, fluoroalkyl groups, alkoxyl groups, ester groups, nitro groups, cyano groups, fluorine atoms and chlorine atoms.

However, J is a direct _{bond, -COO -, - CONH -,} - CH 2 -, - C 2 H 4 -, - O -, - C 3 H 6 -, - C 3 F 6 -, - SO 2 -, _{-S -, - Si (CH 3} ) 2 -, - O-Si (CH 3) 2 -O -, - C 6 H 4 -, - C 6 H 4 -O-C 6 H 4 -, - C 6 _{H 4 -C 3 H 6 -C 6} H 4 - or _{-C 6 H 4 -C 3 F 6} -C 6 H 4 - shows a.

Preferred structures of polyimide, the diamine residue of the polyimide precursor and the polybenzoxazole, and the bisaminophenol residue of the polybenzoxazole precursor include the following structures and some of these hydrogen atoms having 1 to 20 carbon atoms. Examples thereof include a structure in which 1 to 4 are substituted with an alkyl group, a fluoroalkyl group, an alkoxyl group, an ester group, a nitro group, a cyano group, a fluorine atom and a chlorine atom.

However, J is a direct _{bond, -COO -, - CONH -,} - CH 2 -, - C 2 H 4 -, - O -, - C 3 H 6 -, - C 3 F 6 -, - SO 2 -, _{-S -, - Si (CH 3} ) 2 -, - O-Si (CH 3) 2 -O -, - C 6 H 4 -, - C 6 H 4 -O-C 6 H 4 -, - C 6 _{H 4 -C 3 H 6 -C 6} H 4 - or _{-C 6 H 4 -C 3 F 6} -C 6 H 4 - shows a. R ¹ represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.

Further, it is preferable to seal the ends of polyimide, polybenzoxazole, and their precursors with a monoamine having a hydroxyl group, a carboxyl group, a sulfonic acid group or a thiol group, an acid anhydride, an acid chloride or a monocarboxylic acid. Moreover, you may seal using these 2 or more types. By having the above-mentioned group at the resin terminal, the dissolution rate of the resin in an alkaline aqueous solution can be easily adjusted within a preferable range.

Preferred examples of monoamines are 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-amino. Naphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 2-hydroxy-3-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy -6-Aminonaphthalene, 1-carboxy-5-aminonaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3- Aminobenzoic acid, 4-aminobenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 2-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid, 4-aminobenzenesulfonic acid, 3-amino- 4,6-Dihydroxypyrimidine, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-amino-4-terbutylphenol, 2-aminothiophenol, 3-aminothiophenol, 4-aminothiophenol, etc. Can be mentioned.

Preferred examples of acid anhydrides, acid chlorides and monocarboxylic acids include phthalic acid anhydride, maleic anhydride, nadic acid, cyclohexanedicarboxylic acid anhydride, acid anhydrides such as 3-hydroxyphthalic acid anhydride, and 3-carboxyphenol. , 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene, 1-mercapto-7 Monocarboxylic acids such as −carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, 3-carboxybenzene sulfonic acid, 4-carboxybenzene sulfonic acid and their carboxyl groups were acid chlorided. Monoic acid chloride compound, terephthalic acid, phthalic acid, maleic acid, cyclohexanedicarboxylic acid, 1,5-dicarboxynaphthalene, 1,6-dicarboxynaphthalene, 1,7-dicarboxynaphthalene, 2,6-dicarboxynaphthalene, etc. Obtained by reacting a monoacid chloride compound in which only one carboxyl group of the dicarboxylic acids in the above is acid chloride, a monoacid chloride compound with N-hydroxybenzotriazole or N-hydroxy-5-norbornene-2,3-dicarboxyimide. The active ester compound to be used can be mentioned.

The content of the terminal encapsulant such as monoamine, acid anhydride, acid chloride, and monocarboxylic acid described above is preferably in the range of 0.1 to 60 mol% of the number of moles of the acid component monomer or the diamine component monomer charged. More preferably ~ 50 mol%. Within such a range, it is possible to obtain a photosensitive resin composition having an appropriate viscosity of the solution when the photosensitive resin composition is applied and having excellent film physical properties.
Further, a polymerizable functional group may be provided at the end of the resin. Examples of the polymerizable functional group include an ethylenically unsaturated group, an acetylene group, a methylol group, an alkoxymethyl group and the like.

The end sealant introduced into the resin can be easily detected by the following method. For example, a resin into which an end-capping agent has been introduced is dissolved in an acidic solution, decomposed into a diamine component and an acid component, which are constituent units of the resin, and this is measured by gas chromatography (GC) or NMR to obtain a terminal. The sealant can be easily detected. Apart from this, the resin into which the terminal encapsulant has been introduced can be directly detected by pyrolysis gas chromatography (PGC) or infrared spectrum and ¹³ C-NMR spectrum measurement.
(A) The proportion of polyimide, polybenzoxazole and / or precursors thereof in the alkali-soluble resin is preferably 30% by weight or more.
Further, the proportion of the alkali-soluble resin (a) in the photosensitive resin composition is preferably 3 to 50% by weight.

The present invention contains (b) a naphthoquinone diazide esterified product.
(B) As the naphthoquinone diazide esterified product, a polyhydroxy compound in which quinone diazide sulfonic acid is bonded by an ester, a polyamino compound in which quinone diazide sulfonic acid is conjugated with a sulfonamide bond, and a polyhydroxypolyamino compound in which quinone diazide sulfonic acid is esterified. Examples thereof include those having a bond and / or a sulfonamide bond.

It is preferable that 50 mol% or more of all the functional groups of these polyhydroxy compounds and polyamino compounds are substituted with quinonediazide. As the quinone diazide, any of a 5-naphthoquinone diazidosulfonyl group and a 4-naphthoquinone diazidosulfonyl group are preferably used. Further, a naphthoquinone diazidosulfonyl ester compound having a 4-naphthoquinone diazidosulfonyl group and a 5-naphthoquinone diazidosulfonyl group may be contained in the same molecule, or a 4-naphthoquinone diazidosulfonyl ester compound and a 5-naphthoquinone diazidosulfonyl ester compound may be contained. Both may be contained.
The proportion of the (b) naphthoquinone diazide esterified product in the photosensitive resin composition is preferably 1 to 30% by weight.

The present invention includes (c) a compound represented by the general formula (I).

In the formula, R ⁴ , R ⁵ , R ⁷ , and R ⁸ independently have a hydroxyl group, a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a carboxyl group, and 1 to 4 carbon atoms. Indicates one of the ester groups of. R ⁶ represents a hydroxyl group, a hydrogen atom, an alkyl group selected from 1 to 7 carbon atoms, or a hydroxybenzyl group, and at least one R ⁶ is a hydroxyl group. The plurality of R ⁴ , R ⁵ , and R ⁶ may be the same or different. x represents an integer of 1-5.

(C) The compound represented by the general formula (I) contains 80 to 92% of the component of the component (c) in which the x is 1 in the general formula (I) and 7 to 7 to the component in which x is 3. It contains 15% and contains 1 to 5% or more of a component having x of 5.
(C) The purity of the compound represented by the general formula (I) can be determined by a liquid chromatography method. Specifically, in high performance liquid chromatography, an ODS column was used as the column and acetonitrile was used as the developing solvent, and the total area of the peaks detected at the detector wavelength of 254 nm was set to 100%, and each structural component was determined from the area ratio of each peak. The ratio (purity) of is calculated.

The fact that the compound represented by the general formula (I) contains 80 to 92% of the component in which x is 1 means that the purity of the compound represented by the general formula (I) is 80 to 92%. .. It is preferable that 81 to 84% of the component in which x is 1 in the general formula (I) is contained. When the compound represented by the general formula (I) is 80% or more, a photosensitive resin composition having excellent storage stability and an appropriate viscosity of the solution can be obtained.
Further, the compound represented by the general formula (I) contains 7 to 15% of the components represented by the general formula (I) in which x is 3. It is preferable that 12 to 15% or more of the components having x of 3 represented by the general formula (I) are contained. It contains 1 to 5% of components having x of 5 represented by the general formula (I). It is preferable that 4 to 5% or more of the components having x of 5 represented by the general formula (I) are contained. If the component of x 3 represented by the general formula (I) is 7% or more and the component of x 5 represented by the general formula (I) is 1% or more, the photosensitive resin composition is generally used. Even if the amount of the compound represented by the formula (I) added is small, sufficient photosensitive characteristics can be imparted. Further, the film at the time of development has a content of a component having x of 3 represented by the general formula (I) of 15% or less and a component having x of 5 represented by the general formula (I) of 5% or less. The decrease can be suppressed.

Preferred compounds of the compound represented by the general formula (I) in which x is 1 are 2,6-bis (2,4-dihydroxybenzyl) -4-methylphenol and 2,6-bis (2,4). −Dihydroxybenzyl) -4-ethylphenol and 2,6-bis (2,4-dihydroxybenzyl) -4-tert-butylphenol and the like can be mentioned.

Examples of a method for obtaining a phenolic hydroxyl group-containing compound having such a purity include a method of reacting 2,6-bis (hydroxymethyl) -4-methylphenol with resorcinol and 2,6-bis (hydroxymethyl) -4-. There are a method of reacting tert-butylphenol with resorcinol and a method of reacting 2,6-bis (hydroxymethyl) -4-ethylphenol with resorcinol.

Hereinafter, the component of the compound represented by the general formula (1) in which x is 1 is referred to as a trinuclear body, a component in which x is 3 is referred to as a pentucleolus, and a component in which x is 5 is referred to as a component 7 nucleoluus.

The photosensitive resin composition preferably contains (c) a phenolic hydroxyl group-containing compound in an amount of 10 parts by mass or more and 30 parts by mass or less with respect to 100 parts by mass of (a) alkali-soluble resin, and (a) alkali-soluble resin 100. It is more preferable to contain 15 parts by mass or more and 25 parts by mass or less with respect to parts by mass.
By increasing the amount to 10 parts by mass or more, a resin having excellent solubility in an organic solvent can be obtained. Further, 30 parts by mass or less is more preferable in order to develop with less film loss and in a short time.

The photosensitive resin composition preferably contains (c) a phenolic hydroxyl group-containing compound in an amount of 10 parts by mass or more and 70 parts by mass or less with respect to 100 parts by mass of (b) a naphthoquinone diazide esterified product, and (c) a phenolic hydroxyl group. It is more preferable that the contained compound is contained in an amount of 25 parts by mass or more and 50 parts by mass or less with respect to 100 parts by mass of the (b) naphthoquinone diazide esterified product.
By containing 10 parts by mass or more, the phenolic hydroxyl group-containing compound can interact with the naphthoquinone diazide esterified product to further improve the sensitivity of the positive photosensitive resin composition. Further, in order to reduce film loss and improve pattern processability, 70 parts by mass or less is preferable.

The photosensitive resin composition of the present invention contains (d) an organic solvent. Specifically, ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and ethylene glycol dibutyl ether, and ethylene glycol monoethyl ether. Acetates, propylene glycol monomethyl ether acetate, propyl acetate, butyl acetate, isobutyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, methyl lactate, ethyl lactate, butyl lactate and other acetates, acetylacetone, methylpropyl Ketones such as ketones, methylbutyl ketones, methylisobutylketones, cyclopentanone, 2-heptanone, butyl alcohol, isobutyl alcohol, pentanol, 4-methyl-2-pentanol, 3-methyl-2-butanol, 3- Alcohols such as methyl-3-methoxybutanol and diacetone alcohol, aromatic hydrocarbons such as toluene and xylene, N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N, N-dimethylformamide, N , N-Dimethylacetamide, dimethylsulfoxide, γ-butyrolactone and the like. Two or more of these may be used.

The photosensitive resin composition may contain a cross-linking agent.
As the cross-linking agent, 46DMOC, 46DMOEP (trade name, manufactured by Asahi Organic Materials Industry Co., Ltd.), DMOM-PTBP (trade name, manufactured by Honshu Chemical Industry Co., Ltd.), "Nicarac" (registered trademark) MX-290 (commodity) Name, Sanwa Chemical Co., Ltd., BA type benzoxazine, Bm type benzoxazine (trade name, manufactured by Shikoku Kasei Kogyo Co., Ltd.), TriML-P, TriML-35XL (trade name, Honshu Chemical Co., Ltd.) Industrial Co., Ltd.), TM-BIP-A (trade name, Asahi Organic Materials Industry Co., Ltd.), TML-BP, TML-HQ, TML-pp-BPF, TML-BPA, TMOM-BP (trade name) , Honshu Chemical Industry Co., Ltd., Nicarac MX-280, Nicarac MX-270 (trade name, manufactured by Sanwa Chemical Co., Ltd.), HML-TPPHBA, HML-TPHAP, HMOM-TPPHBA, HMOM-TPHAP (trade name) , Made by Honshu Chemical Industry Co., Ltd.).
These thermal cross-linking agents can (a) cross-link the alkali-soluble resin and other additive components to enhance the chemical resistance and hardness of the cured film.

The photosensitive resin composition may contain an adhesion improver. Examples of the adhesion improver include an alkoxysilane-containing aromatic amine compound, an aromatic amide compound, and an aromatic-free silane compound. Two or more of these may be contained. By containing these compounds, the adhesiveness between the film and the substrate after firing or curing can be improved. Specific examples of the alkoxysilane-containing aromatic amine compound and the aromatic amide compound are shown below. In addition to this, it may be a compound obtained by reacting an aromatic amine compound with an alkoxyl group-containing silicon compound. For example, an aromatic amine compound and a group that reacts with an amino group such as an epoxy group or a chloromethyl group may be used. Examples thereof include a compound obtained by reacting a possessing alkoxysilane compound.

The photosensitive resin composition may contain a surfactant, and can improve the coatability with the substrate.
Surfactants include fluorine-based surfactants such as Florard (trade name, manufactured by Sumitomo 3M Co., Ltd.), "Megafuck (registered trademark)" (manufactured by DIC Co., Ltd.), and Sulflon (trade name, manufactured by Asahi Glass Co., Ltd.). Surfactants, KP341 (trade name, manufactured by Shinetsu Chemical Industry Co., Ltd.), DBE (trade name, manufactured by Chisso Co., Ltd.), Granol (trade name, manufactured by Kyoeisha Chemical Co., Ltd.), BYK (Big Chemie Co., Ltd.) ) And other organic siloxane surfactants, and polyflow (trade name, manufactured by Kyoeisha Chemical Co., Ltd.) and other acrylic polymer surfactants.

Next, a method for producing the photosensitive resin composition will be described. For example, a photosensitive resin composition is obtained by dissolving the components (a) to (d) and, if necessary, a thermochromic compound, an organic pigment, a dye, an adhesion improver, an adhesion improver, a surfactant, or the like. be able to. Examples of the melting method include stirring and heating. When heating, the heating temperature is preferably set within a range that does not impair the performance of the photosensitive resin composition, and is usually room temperature to 80 ° C. Further, the dissolution order of each component is not particularly limited, and for example, there is a method of sequentially dissolving compounds having low solubility. In addition, for components that easily generate bubbles during stirring and dissolution, such as surfactants and some adhesion improvers, by dissolving other components and then adding them last, the other components are poorly dissolved due to the generation of bubbles. Can be prevented.

The obtained photosensitive resin composition is preferably filtered using a filtration filter to remove dust and particles. A filter hole diameter in the range of 0.01 μm to 0.8 μm can be appropriately used. The material of the filtration filter includes polypropylene (PP), polyethylene (PE), nylon (NY), polytetrafluoroethylene (PTFE) and the like, but polyethylene and nylon are preferable.

Next, a method for producing a cured film using the photosensitive resin composition of the present invention will be described. As the substrate, Si, ceramics, gallium arsenic, metal, glass, metallic oxide insulating film, silicon nitride, ITO and the like are generally used, but the substrate is not limited thereto. Examples of the coating method of the photosensitive resin composition include a spin coating method, a slit coating method, a dip coating method, a spray coating method, and a printing method. The coating film thickness varies depending on the coating method, the solid content concentration of the composition, the viscosity, and the like, but is usually applied so that the film thickness after drying is 0.1 to 150 μm.

Next, the substrate coated with the photosensitive resin composition is dried to obtain a photosensitive resin film. Drying is preferably carried out in the range of 50 ° C. to 150 ° C. for 1 minute to several hours using an oven, a hot plate, infrared rays or the like.

Next, a method of forming a pattern from the obtained photosensitive resin film will be described. The chemical line is irradiated through a mask having a desired pattern on the photosensitive resin film. Chemical rays used for exposure include ultraviolet rays, visible rays, electron beams, X-rays, etc., but in the present invention, it is preferable to use i-rays (365 nm), h-rays (405 nm), and g-rays (436 nm) of mercury lamps. ..

After exposure, a desired pattern is formed by removing the exposed portion with a developer. The developing solution includes tetramethylammonium, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, and dimethylaminoethyl. An aqueous solution of an alkaline compound such as methacrylate, cyclohexylamine, ethylenediamine and hexamethylenediamine is preferable. In some cases, these alkaline aqueous solutions are mixed with polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, γ-butyrolactone and dimethylacrylamide, methanol, ethanol, etc. Alcohols such as isopropanol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, and ketones such as cyclopentanone, cyclohexanone, isobutyl ketone and methyl isobutyl ketone may be added alone or in combination of several types. Good. After development, it is common to rinse with water. Here, too, alcohols such as ethanol and isopropyl alcohol, and esters such as ethyl lactate and propylene glycol monomethyl ether acetate may be added to water for rinsing.

Next, the pattern of the obtained photosensitive resin film is heated to obtain a cured film. For example, a method of heat-treating at 120 to 400 ° C. for 1 minute to 10 hours, a method of heat-treating at a low temperature of about room temperature to 100 ° C. by adding a curing catalyst, and a method of heat-treating at a low temperature of about room temperature to 100 ° C. by ultrasonic wave or electromagnetic wave treatment. Examples include a method of curing.

The cured film obtained by curing the photosensitive resin composition is a surface protective film or interlayer insulating film for semiconductor devices such as LSIs, an insulating film for organic EL elements, a flattening film for TFT substrates for display elements, and a wiring protective film for circuit substrates. , It can be preferably used for applications such as on-chip microlenses of solid-state image sensors and flattening films for various displays and solid-state image sensors.

Hereinafter, the present invention will be described with reference to Examples and the like, but the present invention is not limited to these examples. The photosensitive resin composition in the examples was evaluated by the following method.

(1) Preparation of Photosensitive Resin Composition Film A photosensitive resin composition (hereinafter referred to as varnish) is applied onto a 6-inch silicon wafer so that the film thickness after prebaking is 10 μm, and then a hot plate (Tokyo Electron) is applied. A photosensitive resin composition film was obtained by prebaking at 100 ° C. for 3 minutes using Mark-7) manufactured by Co., Ltd.

(2) Method for measuring film thickness A Lambda Ace STM-602 manufactured by Dainippon Screen Mfg. Co., Ltd. was used, and the measurement was performed with a refractive index of 1.63.

(3) Exposure A reticle with a cut pattern is set in an exposure machine (all-wavelength stepper Spectrum 3e manufactured by Ultratech Co., Ltd.), and the amount of exposure to the photosensitive resin composition coating of the above method (1). All wavelength exposure was performed at 500 mJ / cm ² (i-line conversion).

(4) Bake after exposure The photosensitive resin composition film after exposure of the above method (3) was heat-treated at 100 ° C. for 1 minute using a hot plate (Mark-7 manufactured by Tokyo Electron Limited). ..

(5) Development The photosensitive resin composition film baked after the exposure of the above method (4) was subjected to 2. Tetramethylammonium hydroxide at 50 rpm using a Mark-7 developing device manufactured by Tokyo Electron Limited. A 38% aqueous solution was sprayed for 10 seconds. Then, the mixture was allowed to stand at 0 rpm for 80 seconds, rinsed with water at 400 rpm, shaken off at 3000 rpm for 10 seconds, and dried to obtain a film after development.

(6) Measurement of residual film ratio The residual film ratio was calculated according to the following formula.
Residual film ratio (%) = film thickness after development ÷ film thickness after prebaking × 100.

(7) the standing time of the evaluation exposure sensitivity to post-exposure bake of 60 minutes, exposure to an exposure amount in the range of 50-1200mJ / cm ² at 25 mJ / cm ² increments to calculate the residual film rate after development The minimum exposure amount was set as the exposure amount when the residual film ratio became constant.

(8) Evaluation of chemical resistance The developed film prepared by the above method (5) at an exposure amount of 500 mJ / cm ² was left to stand for 0 minutes from exposure to post-exposure baking in an inert oven INH-21CD (Koyo Thermo System). A heat treatment was performed at 280 ° C. for 60 minutes under a nitrogen stream (oxygen concentration of 20 ppm or less) using a product manufactured by Co., Ltd. This cure film was immersed in a stripping solution 106 manufactured by Tokyo Ohka Kogyo Co., Ltd. at 50 ° C. for 10 minutes, and the film thickness before and after the treatment was measured to determine the amount of film thickness reduction.

(Synthesis Example 1) Synthesis of hydroxyl group-containing diamine compound (HA) 18.3 g (0.05) of 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (manufactured by Central Glass Co., Ltd., BAHF) (Mole) was dissolved in 100 mL of acetone and 17.4 g (0.3 mol) of propylene oxide (manufactured by Tokyo Kasei Co., Ltd.) and cooled to −15 ° C. A solution prepared by dissolving 20.4 g (0.11 mol) of 3-nitrobenzoyl chloride (manufactured by Tokyo Kasei Co., Ltd.) in 100 mL of acetone was added dropwise thereto. After completion of the dropping, the mixture was stirred at −15 ° C. for 4 hours and then returned to room temperature. The precipitated white solid was filtered off and vacuum dried at 50 ° C.

30 g of the obtained white solid was placed in a 300 mL stainless autoclave, dispersed in 250 mL of methyl cell solve, and 2 g of 5% palladium-carbon (manufactured by Wako Pure Chemical Industries, Ltd.) was added. Hydrogen was introduced into this with a balloon, and the reduction reaction was carried out at room temperature. After about 2 hours, the reaction was terminated after confirming that the balloon did not deflate any more. After completion of the reaction, the palladium compound as a catalyst was removed by filtration, and the mixture was concentrated on a rotary evaporator to obtain a hydroxyl group-containing diamine compound (HA) represented by the following formula.

(Synthesis Example 2) Synthesis of Novolac Resin Under a dry nitrogen stream, m-cresol 108.0 g (1.00 mol), 37 wt% formaldehyde aqueous solution 75.5 g (formaldehyde 0.93 mol), oxalic acid dihydrate 0 After charging .63 g (0.005 mol) and 264 g of methyl isobutyl ketone, the mixture was immersed in an oil bath and a polycondensation reaction was carried out for 4 hours while refluxing the reaction solution. Then, the temperature of the oil bath was raised over 3 hours, and then the pressure in the flask was reduced to remove volatile components, and the mixture was cooled to room temperature to obtain a novolak resin.

(Synthesis Example 3) Synthesis of quinonediazide compound I 21.22 g (0.05 mol) and 5-naphthoquinonediazide sulfonyl acid chloride 26.86 g of TrisP-PA (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) under a dry nitrogen stream. (0.10 mol), 13.43 g (0.05 mol) of 4-naphthoquinonediazidesulfonyl acid chloride was dissolved in 50 g of 1,4-dioxane and brought to room temperature. To this, 15.18 g of triethylamine mixed with 50 g of 1,4-dioxane was added dropwise so that the temperature inside the system did not exceed 35 ° C. After the dropping, the mixture was stirred at 30 ° C. for 2 hours. The triethylamine salt was filtered and the filtrate was added to water. Then, the precipitated precipitate was collected by filtration. This precipitate was dried in a vacuum dryer to obtain quinonediazide compound I represented by the following formula.

(Synthesis Example 4) Synthesis of quinonediazide compound II 15.31 g (0.05 mol) of TrisP-HAP (trade name, manufactured by Honshu Kagaku Kogyo Co., Ltd.) and 40.28 g (0) of 5-naphthoquinonediazidesulfonyl acid chloride under a dry nitrogen stream. .15 mol) was dissolved in 450 g of 1,4-dioxane to bring it to room temperature, and a quinonediazide compound II represented by the following formula was obtained in the same manner as in Synthesis Example 3.

(Synthesis Example 5) Synthesis of phenolic hydroxyl group-containing compound I 150 g of paraformaldehyde was added to 100 g of 4-methylphenol, a 25% aqueous solution of TMAH was added thereto, and the reaction was carried out at 50 ° C. for 7 hours, and then 180 ml of methanol and 285 ml of ion-exchanged water were added. The mixture was cooled to 10 ° C. or lower and crystallized to obtain 2,6-bis (hydroxymethyl) -4-methylphenol.
180 g of resorcinol is added to 15 g of this 2,6-bis (hydroxymethyl) -4-methylphenol, 1.0 g of hydrochloric acid and 60 ml of ion-exchanged water are added thereto, and the reaction is carried out at 50 ° C. for 4 hours, followed by ion exchange with 10 ml of methanol. 300 ml of water was added and cooled to 10 ° C. or lower, and crystal precipitation was carried out to obtain a phenolic hydroxyl group-containing compound I which is a white crystal. The purity of the obtained phenolic hydroxyl group-containing compound was detected by high performance liquid chromatography manufactured by Shimadzu Corporation, using an ODS column as the column and acetonitrile as the developing solvent at a detector wavelength of 254 nm. From the area ratio of each peak, it was 81% for trinuclear bodies, 14% for 5 nuclei, and 5% for 7 nuclei.

(Synthesis Example 6) Synthesis of Phenolic Hydroxyl Group-Containing Compound II 190 g of paraformaldehyde is added to 100 g of 4-tert-butylphenol, a 25% aqueous solution of TMAH is added thereto, the reaction is carried out at 50 ° C. for 8 hours, and then 180 ml of methanol and 285 ml of ion-exchanged water are added. Then, the mixture was cooled to 10 ° C. or lower and crystallized to obtain 2,6-bis (hydroxymethyl) -4-tert-butylphenol.
It was produced in the same manner as in Synthesis Example 3 except that 230 g of resorcinol was added to 15 g of this 2,6-bis (hydroxymethyl) -4-tert-butylphenol. The purity of the obtained phenolic hydroxyl group-containing compound was 91% trinuclear, 7% pentanucleus, and 2% 7 nuclei.

(Synthesis Example 7) Synthesis of phenolic hydroxyl group-containing compound III 165 g of paraformaldehyde was added to 100 g of 4-ethylphenol to produce 2,6-bis (hydroxymethyl) -4-ethylphenol in the same manner as in Synthesis Example 3. ..
It was produced in the same manner as in Synthesis Example 3 except that 215 g of resorcinol was added to 15 g of this 2,6-bis (hydroxymethyl) -4-ethylphenol. The purity of the obtained phenolic hydroxyl group-containing compound was determined by the same method as in Synthesis Example 5. The purity was 86% for trinuclear bodies, 10% for 5 nuclei, and 4% for 7 nuclei.

(Synthesis Example 8) Synthesis of phenolic hydroxyl group-containing compound IV 120 g of resorcinol was added to 15 g of 2,6-bis (hydroxymethyl) -4-methylphenol, and the same as in Synthesis Example 5 was produced. The purity of the obtained phenolic hydroxyl group-containing compound was determined by the same method as in Synthesis Example 5. The purity was 51% for 3 nucleoli, 30% for 5 nucleoli, and 19% for 7 nucleoli.

(A phenolic hydroxyl group-containing compound that is not a compound represented by the general formula (I))
In addition to the above synthesis examples, TrisP-HAP (manufactured by Honshu Chemical Industry Co., Ltd.), TRISP-PA-MF (manufactured by Honshu Chemical Industry Co., Ltd.) and TekP-4HBPA (manufactured by Toyo Synthetic Co., Ltd.) are used as phenolic hydroxyl group-containing compounds. used.

(Example 1)
Under a dry nitrogen air stream, 57.4 g (0.095 mol) of the hydroxyl group-containing diamine and 1.24 g (0.005 mol) of SiDA obtained in Synthesis Example 1 were dissolved in 200 g of NMP. To this, 31.0 g of ODPA (manufactured by Manac Inc., 0.1 mol) was added, and the mixture was stirred at 40 ° C. for 2 hours. Then, a solution of 7.14 g (0.06 mol) of dimethylformamide dimethyl acetal (DFA manufactured by Mitsubishi Rayon Co., Ltd.) diluted with 5 g of NMP was added dropwise over 10 minutes. After the dropping, stirring was continued at 40 ° C. for 2 hours. After the stirring was completed, the solution was poured into 2 L of water, and the precipitate of the polymer solid was collected by filtration. Further, the mixture was washed 3 times with 2 L of water, and the collected polymer solid was dried in a vacuum dryer at 50 ° C. for 72 hours to obtain a polyamic acid polymer.

10 g of the polyamic acid polymer thus obtained was weighed, and 3 g of the phenolic hydroxyl group-containing compound I obtained in Synthesis Example 5 and 3.5 g of the quinonediazide compound I obtained in Synthesis Example 3 were dissolved in 20 g of gamma butyrolactone for exposure. A varnish with a sex resin composition was obtained. Using the obtained varnish, a photosensitive resin composition film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Example 2)
As the phenolic hydroxyl group-containing compound, 1.5 g of the phenolic hydroxyl group-containing compound II obtained in Synthesis Example 6 and 1.5 g of the quinonediazide compound I obtained in Synthesis Example 4 were used in the same manner as in Example 1. , Got a varnish. Using the obtained varnish, a photosensitive resin composition film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Example 3)
A varnish was obtained in the same manner as in Example 1 except that 1 g of the phenolic hydroxyl group-containing compound III obtained in Synthesis Example 7 and 11 g of the quinonediazide compound I obtained in Synthesis Example 3 were used as the phenolic hydroxyl group-containing compound. It was. Using the obtained varnish, a photosensitive resin composition film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Example 4)
The varnish was the same as in Example 1 except that 1.5 g of the phenolic hydroxyl group-containing compound I obtained in Synthesis Example 5 and 3 g of the quinonediazide compound I obtained in Synthesis Example 3 were used as the phenolic hydroxyl group-containing compound. Got Using the obtained varnish, a photosensitive resin composition film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Example 5)
As the phenolic hydroxyl group-containing compound, 1.5 g of the phenolic hydroxyl group-containing compound I obtained in Synthesis Example 5 and 8.5 g of the quinone diazide compound I obtained in Synthesis Example 3 were used in the same manner as in Example 1. , Got a varnish. Using the obtained varnish, a photosensitive resin composition film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Example 6)
As the phenolic hydroxyl group-containing compound, 1.5 g of the phenolic hydroxyl group-containing compound I obtained in Synthesis Example 5 and 13.5 g of the quinone diazide compound I obtained in Synthesis Example 3 were used in the same manner as in Example 1. , Got a varnish. Using the obtained varnish, a photosensitive resin composition film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Example 7)
32.9 g (0.09 mol) of BAHF was dissolved in 500 g of NMP under a dry nitrogen stream. To this, 31.0 g (0.1 mol, ODPA manufactured by Manac Inc.) of 3,3', 4,4'-diphenyl ether tetracarboxylic dianhydride was added together with 50 g of NMP, and the mixture was stirred at 30 ° C. for 2 hours. Then, 2.18 g (0.02 mol, manufactured by Tokyo Kasei Co., Ltd.) of 3-aminophenol was added, and stirring was continued at 40 ° C. for 2 hours. Further, 5 g of pyridine (manufactured by Tokyo Kasei Co., Ltd.) is diluted with 30 g of toluene (manufactured by Tokyo Kasei Co., Ltd.), added to the solution, and a cooling tube is attached to remove water from the system by azeotropic distillation. The reaction was carried out at a temperature of 120 ° C. for 2 hours and further at 180 ° C. for 2 hours. When the temperature of this solution dropped to room temperature, the solution was poured into 3 L of water to obtain a white powder. This powder was collected by filtration and further washed with water three times. After washing, the white powder was dried in a vacuum dryer at 50 ° C. for 72 hours. In this way, a polyimide polymer powder was obtained.

A photosensitive resin composition obtained by dissolving 1.5 g of the phenolic hydroxyl group-containing compound I obtained in Synthesis Example 5 and 8.5 g of the quinone diazide compound I obtained in Synthesis Example 3 in 10 g of this polyimide polymer powder in 20 g of gamma butyrolactone. I got the varnish. Using the obtained varnish, a photosensitive resin composition film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Example 8)
Weigh 10 g of the novolak resin obtained in Synthesis Example 2, and dissolve 1.5 g of the phenolic hydroxyl group-containing compound I obtained in Synthesis Example 5 and 8.5 g of the quinone diazide compound I obtained in Synthesis Example 3 in 20 g of gamma butyrolactone. The varnish of the photosensitive resin composition was obtained. Using the obtained varnish, a photosensitive resin film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Comparative Example 1)
Weighing 10 g of the novolak resin obtained in Synthesis Example 2, 3.5 g of the phenolic hydroxyl group-containing compound IV obtained in Synthesis Example 8 and 4.4 g of the quinone diazide compound I obtained in Synthesis Example 3 were dissolved in 20 g of gamma butyrolactone. The varnish of the photosensitive resin composition was obtained. Using the obtained varnish, a photosensitive resin film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Comparative Example 2)
The photosensitive resin composition was the same as in Example 7 except that 0.5 g of TRISP-HAP (manufactured by Honshu Chemical Industry Co., Ltd.) and 5.5 g of the quinone diazide compound I obtained in Synthesis Example 4 were used as the phenolic hydroxyl group-containing compound. I got a varnish of things. Using the obtained varnish, a photosensitive resin composition film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Comparative Example 3)
As the phenolic hydroxyl group-containing compound, 4.0 g of TRISP-PA-MF (manufactured by Honshu Chemical Industry Co., Ltd.) and 4.4 g of the quinonediazide compound I obtained in Synthesis Example 3 were used, and the varnish was prepared in the same manner as in Example 1. Obtained. Using the obtained varnish, a photosensitive resin composition film was prepared on a silicon wafer, exposed, developed, and heat-treated to evaluate the sensitivity, residual film ratio, and chemical resistance of the varnish.

(Comparative Example 4)
A varnish was obtained in the same manner as in Example 8 except that 0.5 g of TekP-4HBPA (manufactured by Honshu Chemical Industry Co., Ltd.) and 5.5 g of the quinonediazide compound II obtained in Synthesis Example 4 were used as the phenolic hydroxyl group-containing compound. It was. Using the obtained varnish, a photosensitive resin composition film was prepared, exposed and developed on a silicon wafer as described above, and the sensitivity and residual film ratio of the varnish were evaluated.

The compositions and evaluation results of Examples 1 to 8 and Comparative Examples 1 to 4 are shown in Tables 1 and 2.

Claims (8)

(A) Alkali-soluble resin and
(B) Naftquinone diazide esterified product and
(C) The compound represented by the general formula (I) and
(D) A photosensitive resin composition containing an organic solvent.
The x of the general formula (I) is 1 with respect to 100% of the total area of the peak detected at the detector wavelength of 254 nm by the liquid chromatography method of the compound represented by the general formula (I) (c). The area of the peak for the compound is 80-92%, the area of the peak for the compound where x is 3 is 7 to 15%, and the area of the peak for the compound where x is 5 is 1-5%. A photosensitive resin composition containing 10 parts by mass or more and 30 parts by mass or less of the compound represented by the general formula (I) with respect to 100 parts by mass of (a) alkali-soluble resin.

(In the formula, R ⁴ , R ⁵ , R ⁷ , and R ⁸ independently have a hydroxyl group, a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a carboxyl group, and 1 to 1 carbon atoms. Indicates any of the ester groups of 4. R ⁶ independently represents a hydroxyl group, a hydrogen atom, an alkyl group selected from 1 to 7 carbon atoms, or a hydroxybenzyl group, and at least one R ⁶ is a hydroxyl group. A plurality of R ⁴ , R ⁵ , and R ⁶ may be the same or different. X indicates an integer of 1 to 5.) The component of the compound represented by the general formula (I) in which x is 1 is 2,6-bis (2,4-dihydroxybenzyl) -4-methylphenol and 2,6-bis (2,). The photosensitive resin composition according to claim 1, which is any one of 4-dihydroxybenzyl) -4-ethylphenol and 2,6-bis (2,4-dihydroxybenzyl) -4-tert-butylphenol. (B) The photosensitive resin composition according to claim 1 or 2, which contains the component (c) in a range of 10 parts by mass or more and 50 parts by mass or less with respect to 100 parts by mass of the naphthoquinone diazide esterified product. The photosensitive resin composition according to any one of claims 1 to 3, wherein the alkali-soluble resin is a polyimide and / or a polyimide precursor. A method for producing a cured film, which comprises a step of applying the photosensitive resin composition according to any one of claims 1 to 4 to a substrate and drying it, a step of exposing it, a step of developing it using an alkaline developer, and a step of heat treatment. .. A cured film obtained by curing the photosensitive resin composition according to any one of claims 1 to 4. A display device having a flattening film and a display element in this order on a substrate on which a thin film transistor (TFT) is formed, wherein the flattening film is the cured film according to claim 6. The display device according to claim 7, wherein the display element is an organic electroluminescence element.