TWI708998B - Photosensitive resin composition, photosensitive resin layer and electronic device using the same - Google Patents

Abstract

Disclosed are a photosensitive resin composition including (A) an alkali soluble resin; (B) a photosensitive diazoquinone compound; (C) a compound represented by Chemical Formula 1; and (D) a solvent, a photosensitive resin layer manufactured using the same, and an electronic device including the photosensitive resin layer.

Description

Photosensitive resin composition, photosensitive resin layer using the same, and electronic device

This application claims the priority and rights of Korean Patent Application No. 10-2018-0104743 filed with the Korean Intellectual Property Office on September 03, 2018, and the entire content of the application is incorporated herein by reference.

The present invention relates to a photosensitive resin composition, a photosensitive resin layer and an electronic device using the photosensitive resin composition.

Polyimide resins, polybenzoxazole resins, and the like, which have improved heat resistance, electrical characteristics, and mechanical characteristics, have been widely used in surface protective layers and interlayer insulating layers used in materials for display device panels and semiconductor devices. Since these resins have low solubility in various solvents, these resins are usually provided with compositions in which their precursors are dissolved in the solvent.

In recent years, the emergence of environmental problems has required countermeasures against de-organic solvents, and various types of heat-resistant photosensitive resin materials that can be developed with alkaline aqueous solutions in the same manner as photoresists have been proposed.

Among them, there has been proposed a method of using a photosensitive resin composition comprising a mixture of a hydroxypolyamide resin soluble in an alkaline aqueous solution and a photoacid generator such as a naphthoquinonediazide compound The hydroxy polyamide resin is a heat-resistant resin after thermal curing.

The photosensitive mechanism of the photosensitive resin composition utilizes exposure of the photosensitive quinone diazide compound to the naphthoquinonediazide compound (that is, another photosensitive quinone diazide compound) and polybenzoxazole (polybenzoxazole, PBO) precursor, and thereby convert the photosensitive quinone diazide compound into an indene carboxylic acid compound to increase the dissolution rate in the alkaline aqueous solution. The difference in dissolution rate between the exposed part and the unexposed part can be used to produce a relief pattern composed of the unexposed part.

The photosensitive resin composition can form a positive relief pattern by exposure and development with an alkaline aqueous solution. In addition, thermally cured film characteristics can be obtained by heating.

However, in the manufacturing process of semiconductors and the like, fine processing is performed, and the interval between patterns becomes shorter. Therefore, when the amount of layer reduction becomes larger during development, in the unexposed part adjacent to the exposed part of the opening, the dissolution rate of the unexposed part is smaller, but during the development, the developing solution will contact the sides of the layer and Upper side. Therefore, the shape of the pattern becomes too thin, thereby reducing the reliability of the semiconductor package in the manufacturing process of the semiconductor device.

Therefore, it is necessary to carry out development with almost no dissolution of the unexposed parts (this phenomenon is called the residual rate of the developed film). However, when the residual rate of the developed film increases, a high exposure dose is required for the phenomenon of the exposed portion (this is called low sensitivity).

Therefore, a method of adding a separate additive to the heat-resistant resin precursor has been proposed as a method of increasing the film residual rate (developing control) and the sensitivity of development during development. However, with the conventionally used individual additives, the improvement of post-development improvement is not satisfactory, and there is a limit to meet the recent demand for high sensitivity to improve the output of the characteristics of photosensitive materials.

Therefore, research continues to develop photosensitive resin compositions that can solve these problems.

An embodiment provides a photosensitive resin composition capable of improving sensitivity by using a dissolution control agent having a specific structure to improve developability.

Another embodiment provides a photosensitive resin layer manufactured using the photosensitive resin composition.

Another embodiment provides an electronic device including a photosensitive resin layer.

在化學式1中， L¹ 是單鍵或經取代或未經取代的C1到C20伸烷基， R¹ 是經取代或未經取代的C3到C20脂族環基或經取代或未經取代的C6到C20芳環基，其條件是脂族環基並不包含不飽和鍵，以及 R² 到R⁴ 各自獨立地為羥基或C1到C10三氟烷基，其條件是R² 到R⁴ 中的至少一個是羥基且R² 到R⁴ 中的至少一個是C1到C10三氟烷基。 R¹ 可以是經取代或未經取代的C3到C20環烷基或經取代或未經取代的C6到C20芳基。 R¹ 是未經取代的C3到C20環烷基、經C1到C10烷基取代的C3到C20環烷基、經羥基取代的C3到C20環烷基、未經取代的C6到C20芳基、經C1到C10烷基取代的C6到C20芳基或經羥基取代的C6到C20芳基。 R² 和R⁴ 可各自獨立地為C1到C10三氟烷基，且R³ 可為羥基。An embodiment provides a photosensitive resin composition comprising: (A) an alkali-soluble resin; (B) a photosensitive quinone diazide compound; (C) a compound represented by Chemical Formula 1; and (D) a solvent. [Chemical formula 1]

In Chemical Formula 1, L ¹ is a single bond or a substituted or unsubstituted C1 to C20 alkylene group, and R ¹ is a substituted or unsubstituted C3 to C20 aliphatic cyclic group or a substituted or unsubstituted C6 to C20 aromatic ring group, provided that the aliphatic ring group does not contain an unsaturated bond, and R ² to R ⁴ are each independently a hydroxyl group or a C1 to C10 trifluoroalkyl group, provided that R ² to R ⁴ At least one of is a hydroxyl group and at least one of R ² to R ⁴ is a C1 to C10 trifluoroalkyl group. R ¹ may be a substituted or unsubstituted C3 to C20 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group. R ¹ is unsubstituted C3 to C20 cycloalkyl, C3 to C20 cycloalkyl substituted with C1 to C10 alkyl, C3 to C20 cycloalkyl substituted with hydroxyl, unsubstituted C6 to C20 aryl, A C6 to C20 aryl group substituted with a C1 to C10 alkyl group or a C6 to C20 aryl group substituted with a hydroxyl group. R ² and R ⁴ may each independently be a C1 to C10 trifluoroalkyl group, and R ³ may be a hydroxyl group.

The content of the compound represented by Chemical Formula 1 may be 1 part by weight to 30 parts by weight based on 100 parts by weight of the alkali-soluble resin.

[化學式3]

[化學式4]

[化學式5]

[化學式6]

The compound represented by Chemical Formula 1 may be represented by one of Chemical Formula 2 to Chemical Formula 6. [Chemical formula 2]

[Chemical formula 3]

[Chemical formula 4]

[Chemical formula 5]

[Chemical formula 6]

The alkali-soluble resin may be a polybenzoxazole precursor, a polyimide precursor, or a combination thereof.

The photosensitive resin composition may include 1 part by weight to 50 parts by weight of the photosensitive quinone diazide compound, 1 part by weight to 30 parts by weight of the compound represented by Chemical Formula 1, and 100 parts by weight to 300 parts by weight based on 100 parts by weight of the alkali-soluble resin. Parts by weight of solvent.

The photosensitive resin composition may further include additives, the additives being diacids, alkanolamines, leveling agents, silane coupling agents, surfactants, epoxy compounds, radical polymerization initiators, thermal latent acid generators, or Its combination.

Another embodiment provides a photosensitive resin layer manufactured using the photosensitive resin composition.

Another embodiment provides an electronic device including a photosensitive resin layer.

Other embodiments of the present invention are included in the following specific embodiments.

The photosensitive resin composition according to an embodiment can improve sensitivity due to the improvement of developability by using a dissolution control agent having a specific structure.

Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present invention is not limited thereto and the present invention is defined by the scope of application practice.

In this specification, when no other specific definition is provided, "alkyl" refers to C1 to C20 alkyl, the term "alkenyl" refers to C2 to C20 alkenyl, and the term "cycloalkenyl" refers to C3 to C20 ring Alkenyl, the term "heterocyclenyl" refers to a C3 to C20 heterocycloalkenyl, the term "aryl" refers to a C6 to C20 aryl group, the term "aralkyl" refers to a C7 to C20 aralkyl group, the term " Alkylene" refers to C1 to C20 alkylene, the term "arylene" refers to C6 to C20 arylene, the term "alkyl aryl" refers to C7 to C20 alkyl aryl, the term "heteroaryl" Group" refers to a C3 to C20 heteroaryl group, and the term "alkoxy" refers to a C1 to C20 alkoxy group.

In this specification, when a specific definition is not provided otherwise, "substituted" means replacing at least one hydrogen atom by a substituent selected from the following: halogen atom (F, Cl, Br or I), hydroxyl, C1 to C20 alkane Oxy, nitro, cyano, amino, amino, azido, formamidino, hydrazino, hydrazino, carbonyl, carbamyl, thiol, ester, ether, carboxyl or salts thereof , Sulfonic acid group or its salt, phosphoric acid or its salt, C1 to C20 alkyl, C2 to C20 alkenyl, C2 to C20 alkynyl, C6 to C20 aryl, C3 to C20 cycloalkyl, C3 to C20 cycloalkenyl , C3 to C20 cycloalkynyl, C2 to C20 heterocycloalkyl, C2 to C20 heterocycloalkenyl, C2 to C20 heterocycloalkynyl, C3 to C20 heteroaryl or a combination thereof.

In this specification, when no specific definition is provided otherwise, "hetero" means that at least one heteroatom among N, O, S, and P is included in the chemical formula.

In this specification, when no specific definition is provided separately, "(meth)acrylate" means "acrylate" and "methacrylate".

In this specification, when no definition is provided otherwise, the term "combination" means mixing or copolymerization. In addition, "copolymerization" refers to block copolymerization, substitution copolymerization or random copolymerization, and "copolymer" refers to block copolymer, substitution copolymer or random copolymer.

In this specification, when a specific definition is not otherwise provided, the unsaturated bond includes a bond between other atoms such as a carbonyl bond or an azo bond, and a multiple bond between carbon-carbon atoms.

In this specification, when no other definition is provided, hydrogen is bonded at the position that should be given when the chemical bond is not shown in the chemical formula.

In addition, in this specification, when no definition is provided otherwise, "*" refers to the point of bonding with the same atom or chemical formula or different atoms or chemical formulas.

在化學式1中， L¹ 是單鍵或經取代或未經取代的C1到C20伸烷基， R¹ 是經取代或未經取代的C3到C20脂族環基或經取代或未經取代的C6到C20芳環基，其條件是脂族環基並不包含不飽和鍵。 R² 到R⁴ 各自獨立地為羥基或C1到C10三氟烷基，其條件是R² 到R⁴ 中的至少一個是羥基且R² 到R⁴ 中的至少一個是C1到C10三氟烷基。A photosensitive resin composition according to an embodiment includes: (A) an alkali-soluble resin; (B) a photosensitive quinone diazide compound; (C) a compound represented by Chemical Formula 1; and (D) a solvent. [Chemical formula 1]

In Chemical Formula 1, L ¹ is a single bond or a substituted or unsubstituted C1 to C20 alkylene group, and R ¹ is a substituted or unsubstituted C3 to C20 aliphatic cyclic group or a substituted or unsubstituted C6 to C20 aromatic ring groups, provided that the aliphatic ring groups do not contain unsaturated bonds. R ² to R ⁴ are each independently a hydroxyl group or a C1 to C10 alkyl trifluoromethyl, with the proviso that R ² to R ⁴ is hydroxy at least one of R ² to R ⁴ and at least one is a C1 to C10 trifluoroalkyl base.

When the photosensitive resin composition according to an embodiment is used as a protective film or insulating layer in a semiconductor or a display device, the composition is applied by coating the composition, UV exposure, development, and curing. For the characteristics of the process material, sensitivity is very important for the increase in throughput, and therefore, compared with conventional references, by using the compound represented by Chemical Formula 1 as the dissolution control agent, the photosensitive resin composition according to an embodiment Objects can greatly improve sensitivity.

In the following, each ingredient is specifically described.

(C) Compound represented by chemical formula 1

The photosensitive resin composition according to an embodiment can greatly improve sensitivity and heat resistance by including the chemical represented by Chemical Formula 1 as a dissolution control agent. Specifically, when a photosensitive resin composition containing a compound represented by Chemical Formula 1 as a dissolution control agent is developed with an alkaline aqueous solution, the dissolution rate and sensitivity of the exposed portion are significantly increased to improve developability, and thus achieve high resolution Patterning and high heat resistance.

For example, in Chemical Formula 1, R ¹ may be a substituted or unsubstituted C3 to C20 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group.

For example, R ¹ can be unsubstituted C3 to C20 cycloalkyl, C3 to C20 cycloalkyl substituted with C1 to C10 alkyl, C3 to C20 cycloalkyl substituted with hydroxy, and unsubstituted C6 To C20 aryl, C6 to C20 aryl substituted with C1 to C10 alkyl or C6 to C20 aryl substituted with hydroxy.

For example, R ¹ may be a C3 to C20 cycloalkyl group substituted with a hydroxyl group or a C6 to C20 aryl group substituted with a hydroxyl group. When R ¹ has a hydroxyl group as a substituent, the sensitivity can be improved more than a group without a substituent or having a methyl group or the like as a substituent.

For example, L ¹ may be a substituted or unsubstituted C1 to C20 alkylene group. When L ¹ is an alkylene group, the sensitivity can be improved more than a single bond.

For example, in Chemical Formula 1, R ² and R ⁴ may each independently be a C1 to C10 trifluoroalkyl group, and R ³ may be a hydroxyl group.

For example, based on 100 parts by weight of the alkali-soluble resin, the content of the compound represented by Chemical Formula 1 may be 1 part by weight to 30 parts by weight. When the compound represented by Chemical Formula 1 is included within the amount range, sensitivity can be improved.

[化學式3]

[化學式4]

[化學式5]

[化學式6]

For example, the compound represented by Chemical Formula 1 may be represented by one of Chemical Formula 2 to Chemical Formula 6, but is not limited thereto. [Chemical formula 2]

[Chemical formula 3]

[Chemical formula 4]

[Chemical formula 5]

[Chemical formula 6]

(A) Alkali-soluble resin

The alkali-soluble resin used in the photosensitive resin composition may be a polybenzoxazole precursor, a polyimide precursor, a novolak resin, a bisphenol A resin, a bisphenol F resin, and a (meth)acrylate resin. Or a combination thereof, and in one embodiment, a polybenzoxazole precursor, a polyimide precursor, or a combination thereof can be used as the alkali-soluble resin, but the type of the alkali-soluble resin is not limited.

[化學式8]

The polybenzoxazole precursor includes a repeating unit represented by Chemical Formula 7 or a repeating unit represented by Chemical Formula 7 and Chemical Formula 8, and may have a thermally polymerizable functional group at at least one terminal. [Chemical formula 7]

[Chemical formula 8]

在化學式9中， R₂₃ 到R₂₆ 各自獨立地為經取代或未經取代的C1到C20烷基、經取代或未經取代的C6到C20芳基、經取代或未經取代的C1到C20烷氧基或羥基， R₂₇ 和R₂₈ 各自獨立地為經取代或未經取代的C1到C20伸烷基或經取代或未經取代的C6到C20伸芳基，以及 k是範圍介於1到50的整數。In Chemical Formula 7 and Chemical Formula 8, X ₁ is an aromatic organic group or a tetravalent aliphatic organic group, Y ₁ and Y ₂ are each independently an aromatic organic group or a divalent aliphatic organic group, and X ₂ Is an aromatic organic group, a divalent aliphatic organic group, a divalent alicyclic organic group, or an organic group having a structure represented by Chemical Formula 9. [Chemical formula 9]

In Chemical Formula 9, R ₂₃ to R ₂₆ are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C20 Alkoxy or hydroxy, R ₂₇ and R ₂₈ are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group, and k is in the range of 1. Integer to 50.

The type of the polybenzoxazole precursor is not particularly limited and may be a random copolymer, a block copolymer, or an alternative copolymer.

In addition, when the polybenzoxazole precursor includes the repeating unit represented by Chemical Formula 7 and the repeating unit represented by Chemical Formula 8, the content of the repeating unit represented by Chemical Formula 8 may be greater than 50 mole%, for example, greater than or equal to 60 mole%. Ear% and less than 100 mol%.

For example, X ₁ can be a moiety derived from: 3,3'-diamino-4,4'-dihydroxybiphenyl, 4,4'-diamino-3,3'-dihydroxybiphenyl, Bis(3-amino-4-hydroxyphenyl)propane, bis(4-amino-3-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)sulfonate, bis(4-amino-3- Hydroxyphenyl) sulfide, 2,2-bis(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis(4-amino-3 -Hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2'-bis(3-amino-4-hydroxy-5-trifluoromethylphenyl)hexafluoropropane, 2,2'-bis(3-amino-4-hydroxy-6-trifluoromethylphenyl)hexafluoropropane, 2,2'-bis(3-amino-4-hydroxy-2-trifluoromethylbenzene Yl)hexafluoropropane, 2,2'-bis(4-amino-3-hydroxy-5-trifluoromethylphenyl)hexafluoropropane, 2,2'-bis(4-amino-3-hydroxy-6 -Trifluoromethylphenyl)hexafluoropropane, 2,2'-bis(4-amino-3-hydroxy-2-trifluoromethylphenyl)hexafluoropropane, 2,2'-bis(3-amino) -4-hydroxy-5-pentafluoroethylphenyl)hexafluoropropane, 2-(3-amino-4-hydroxy-5-trifluoromethylphenyl)-2'-(3-amino-4-hydroxy -5-Pentafluoroethylphenyl)hexafluoropropane, 2-(3-amino-4-hydroxy-5-trifluoromethylphenyl)-2'-(3-hydroxy-4-amino-5-tri Fluoromethylphenyl)hexafluoropropane, 2-(3-amino-4-hydroxy-5-trifluoromethylphenyl)-2'-(3-hydroxy-4-amino-6-trifluoromethylbenzene Yl)hexafluoropropane, 2-(3-amino-4-hydroxy-5-trifluoromethylphenyl)-2'-(3-hydroxy-4-amino-2-trifluoromethylphenyl)hexafluoro Propane, 2-(3-amino-4-hydroxy-2-trifluoromethylphenyl)-2'-(3-hydroxy-4-amino-5-trifluoromethylphenyl)hexafluoropropane, 2- (3-Amino-4-hydroxy-6-trifluoromethylphenyl)-2'-(3-hydroxy-4-amino-5-trifluoromethylphenyl)hexafluoropropane, 2,6-bis[ [[5-[1-(Amino-4-hydroxyphenyl)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-hydroxyphenyl]amino]methyl]- 4-cresol and its combination, but not limited thereto.

[化學式11]

在化學式10和化學式11中， A₁ 可選自O、CO、CR₈ R₉ 、SO₂ 、S以及單鍵， R₈ 和R₉ 可各自獨立地選自氫和經取代或未經取代的烷基，且優選地，R₈ 和R₉ 為氟烷基， R₅ 到R₇ 可各自獨立地選自氫、經取代或未經取代的烷基、羥基、羧酸基以及硫醇基， n₁ 可為以是1到2的整數，以及 n₂ 和n₃ 可各自獨立地為1到3的整數。In addition, X ₁ may be a part represented by a compound represented by Chemical Formula 10 and Chemical Formula 11. [Chemical formula 10]

[Chemical formula 11]

In Chemical Formula 10 and Chemical Formula 11, A ₁ may be selected from O, CO, CR ₈ R ₉ , SO ₂ , S, and a single bond, and R ₈ and R ₉ may each independently be selected from hydrogen and substituted or unsubstituted Alkyl group, and preferably, R ₈ and R ₉ are fluoroalkyl groups, R ₅ to R ₇ may each independently be selected from hydrogen, substituted or unsubstituted alkyl groups, hydroxyl groups, carboxylic acid groups and thiol groups, n ₁ may be an integer of 1 to 2, and n ₂ and n ₃ may each independently be an integer of 1 to 3.

In addition, X ₂ can be derived from aromatic diamines, silyl diamines, and alicyclic diamines.

Specific examples of aromatic diamines may be 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diamino Diphenylmethane, 4,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2 ,6-Naphthalenediamine, bis(4-aminophenoxyphenyl) sulfite, bis(3-aminophenoxyphenyl) sulfite, bis(4-aminophenoxy)biphenyl, bis[4- (4-aminophenoxy)phenyl]ether, 1,4-bis(4-aminophenoxy)benzene and the like, but not limited thereto. In addition, these aromatic diamine monomers may be used alone or in the form of a mixture thereof.

Specific examples of silicon diamine can be bis(4-aminophenyl)dimethyl silane, bis(4-aminophenyl)tetramethylsiloxane, bis(p-aminophenyl)tetramethyldisiloxane , Bis(γaminopropyl)tetramethyldisiloxane, 1,4-bis(γaminopropyldimethylsilyl)benzene, bis(4-aminobutyl)tetramethyldisiloxane , Bis(γaminopropyl)tetraphenyldisiloxane, 1,3-bis(aminopropyl)tetramethyldisiloxane and the like, but not limited thereto.

Specific examples of the alicyclic diamine may be cyclohexyl diamine, methylene bicyclohexyl amine, and the like, but are not limited thereto.

In addition, the aromatic diamine, silyldiamine, and alicyclic diamine may be used alone or in the form of a mixture thereof, and the aromatic diamine, silyldiamine, and alicyclic diamine may be appropriately mixed.

Y ₁ and Y ₂ may be part of a dicarboxylic acid or a dicarboxylic acid derivative, for example.

A specific example of the dicarboxylic acid may be Y(COOH) ₂ (wherein Y is the same as Y ₁ and Y ₂ ).

Examples of dicarboxylic acid derivatives include carbonyl halide derivatives or active compounds of active ester derivatives obtained by reacting Y(COOH) ₂ with 1-hydroxy-1,2,3-benzotriazole. Examples of dicarboxylic acid derivatives may be compounds selected from the group consisting of 4,4'-oxydiphenylcarboxylic acid chloride, diphenoxydicarboxylic acid chloride, bis(phenylcarboxylic acid chloride) chloride, bis(benzene Carboxylic acid chloride) ether, bis(phenyl carboxylic acid chloride) phenyl ketone, phthalic acid dichloride, terephthalic acid dichloride, isophthalic acid dichloride, formic acid dichloride, diphenoxy dicarboxylic acid Acid benzotriazole and combinations thereof.

[化學式13]

[化學式14]

在化學式12到化學式14中， R₁₀ 到R₁₃ 可各自獨立地為氫或經取代或未經取代的烷基， n₆ 、n₈ 以及n₉ 可各自獨立地為1到4的整數，n₇ 可為1到3的整數，以及 A₂ 可以是O、CR₁₄ R₁₅ 、CO、CONH、S或SO₂ ,其中R₁₄ 和R₁₅ 可各自獨立地為氫、經取代或未經取代的烷基，或氟烷基。In addition, Y ₁ and Y ₂ may be represented by one of Chemical Formula 12 to Chemical Formula 14. [Chemical formula 12]

[Chemical formula 13]

[Chemical formula 14]

In Chemical Formula 12 to Chemical Formula 14, R ₁₀ to R ₁₃ may each independently be hydrogen or a substituted or unsubstituted alkyl group, n ₆ , n ₈ and n ₉ may each independently be an integer of 1 to 4, and n ₇ can be an integer from 1 to 3, and A ₂ can be O, CR ₁₄ R ₁₅ , CO, CONH, S, or SO ₂ , where R ₁₄ and R ₁₅ can each independently be hydrogen, substituted or unsubstituted Alkyl, or fluoroalkyl.

In addition, the polybenzoxazole precursor may have a thermally polymerizable functional group derived from a reactive end-capping monomer at one or both ends of the branched chain.

The reactive end-capping monomer may be a monoamine with a double bond, a monoanhydride with a double bond, or a combination thereof.

The monoamine having a double bond may be toluidine, dimethylaniline, ethylaniline, aminophenol, aminobenzyl alcohol, aminoindene, aminoacetophenone, or a combination thereof, but is not limited thereto.

[化學式16]

[化學式17]

The monoacid anhydride having a double bond may be 5-norbornene-2,3-dicarboxylic acid anhydride of chemical formula 15, 3,6-epoxy-1,2,3,6-tetrahydrophthalic acid of chemical formula 16. Acid anhydride, isobutenyl succinic anhydride of chemical formula 17, maleic anhydride, aconitic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, cis-1,2,3,6-tetrahydrophthalic anhydride Formic anhydride, itaconic anhydride (IA), citraconic anhydride (CA), 2,3-dimethylmaleicanhydride (DMMA) or a combination thereof, but not limited to this. [Chemical formula 15]

[Chemical formula 16]

[Chemical formula 17]

在化學式18中，R₁₆ 是H、CH₂ COOH或CH₂ CHCHCH₃ 。 [化學式19]

在化學式19中，R₁₇ 和R₁₈ 各自獨立地為H或CH₃ 。 [化學式20]

[化學式21]

在化學式21中，R₁₉ 是H或CH₃ ，且R₂₀ 是CH₂ 或氧原子。 [化學式22]

在化學式22中，R₂₁ 和R₂₂ 各自獨立地為H、CH₃ 或OCOCH₃ 。In addition, Chemical Formulas 18 to 22 are examples of thermally polymerizable functional groups located at the ends of the polybenzoxazole precursor, and the thermally polymerizable functional groups may be crosslinked during the heating process. [Chemical formula 18]

In Chemical Formula 18, R ₁₆ is H, CH ₂ COOH, or CH ₂ CHCHCH ₃ . [Chemical formula 19]

In Chemical Formula 19, R ₁₇ and R ₁₈ are each independently H or CH ₃ . [Chemical formula 20]

[Chemical formula 21]

In Chemical Formula 21, R ₁₉ is H or CH ₃ , and R ₂₀ is CH ₂ or an oxygen atom. [Chemical formula 22]

In Chemical Formula 22, R ₂₁ and R ₂₂ are each independently H, CH ₃ or OCOCH ₃ .

The polybenzoxazole precursor may have a weight average molecular weight (Mw) of 3,000 g/mole to 300,000 g/mole. When the weight average molecular weight is within the range, sufficient physical properties and excellent solubility in organic solvents can be obtained, and handling is easy.

[化學式24]

The polyimide precursor may include repeating units represented by Chemical Formula 23 and Chemical Formula 24. When the repeating unit represented by Chemical Formula 23 is included, the resin can be quickly cured at high temperature, and when the repeating unit represented by Chemical Formula 24 is included, thermal characteristics can be improved during curing at high temperature. [Chemical formula 23]

[Chemical formula 24]

In Chemical Formulas 23 to 24, X ₃ is an aromatic organic group or a divalent alicyclic organic group, Y ₃ and Y ₄ are each independently an aromatic organic group or a tetravalent alicyclic organic group, and X ₄ Is an aromatic organic group, a divalent alicyclic organic group, or a functional group represented by Chemical Formula 9, and R ₁₀₀ to R ₁₀₃ are each independently hydrogen or a substituted or unsubstituted C1 to C20 alkyl group.

In the photosensitive resin composition, when the sum of the repeating unit represented by Chemical Formula 23 and the repeating unit represented by Chemical Formula 24 is 100 mol%, 5 mol% to 50 mol% of the compound represented by Chemical Formula 23 may be included. The repeating unit and 50 mol% to 95 mol% of the repeating unit represented by Chemical Formula 24.

The polyimide precursor may have a weight average molecular weight (Mw) of 3,000 g/mol to 300,000 g/mol.

(B) Photosensitive quinone diazide compound

The photosensitive quinone diazide compound may be a compound having a 1,2-benzoquinonediazide structure or a 1,2-naphthoquinonediazide structure.

在化學式71中， R³¹ 到R³³ 可各自獨立地為氫原子或經取代或未經取代的烷基，並且確切地為CH₃ ， D¹ 到D³ 可以各自獨立地為OQ，其中Q可以是氫原子，或由化學式72a表示的官能團或由化學式72b表示的官能團，其條件是Q並不同時為氫原子，以及 n31到n33可各自獨立地為1到5的整數。 [化學式72a]

[化學式72b]

[化學式73]

在化學式73中， R³⁴ 是氫原子或經取代或未經取代的烷基， D⁴ 到D⁶ 可各自獨立地為OQ，其中Q可與化學式71中所定義的相同，以及 n34到n36可各自獨立地為1到5的整數。 [化學式74]

在化學式74中， A³ 為CO或CR⁵⁰⁰ R⁵⁰¹ ，其中R⁵⁰⁰ 和R⁵⁰¹ 可各自獨立地為經取代或未經取代的烷基， D⁷ 到D¹⁰ 可各自獨立地為氫原子、經取代或未經取代的烷基、OQ或NHQ，其中Q與化學式71中所定義的相同， n37、n38、n39以及n40可各自獨立地為1到4的整數，以及 n37+n38和n39+n40可各自獨立地為小於或等於5的整數， 其條件是D⁷ 到D¹⁰ 中的至少一個可以是OQ，且一個芳環可包含一個到三個OQ，且另一芳環可包含一個到四個OQ。 [化學式75]

在化學式75中， R₃₅ 到R₄₂ 可各自獨立地為氫原子或經取代或未經取代的烷基， n41和n42可各自獨立地為1到5的整數，例如2到4，以及 Q可與化學式71中所定義的相同。Examples of the photosensitive quinone diazide compound may be compounds represented by Chemical Formula 71 and Chemical Formula 73 to Chemical Formula 75, but are not limited thereto. [Chemical formula 71]

In Chemical Formula 71, R ³¹ to R ³³ may each independently be a hydrogen atom or a substituted or unsubstituted alkyl group, and are specifically CH ₃ , and D ¹ to D ³ may each independently be OQ, where Q may Is a hydrogen atom, or a functional group represented by chemical formula 72a or a functional group represented by chemical formula 72b, provided that Q is not a hydrogen atom at the same time, and n31 to n33 may each independently be an integer of 1 to 5. [Chemical formula 72a]

[Chemical formula 72b]

[Chemical formula 73]

In Chemical Formula 73, R ³⁴ is a hydrogen atom or a substituted or unsubstituted alkyl group, D ⁴ to D ⁶ may each independently be OQ, wherein Q may be the same as defined in Chemical Formula 71, and n34 to n36 may be Each independently is an integer from 1 to 5. [Chemical formula 74]

In the chemical formula 74, A ³ is CO or CR ⁵⁰⁰ R ⁵⁰¹ , wherein R ⁵⁰⁰ and R ⁵⁰¹ may each independently be a substituted or unsubstituted alkyl group, and D ⁷ to D ¹⁰ may each independently be a hydrogen atom, A substituted or unsubstituted alkyl group, OQ, or NHQ, where Q is the same as defined in Chemical Formula 71, n37, n38, n39, and n40 may each independently be an integer from 1 to 4, and n37+n38 and n39+n40 May be each independently an integer less than or equal to 5, provided that at least one of D ⁷ to D ¹⁰ may be OQ, and one aromatic ring may contain one to three OQ, and the other aromatic ring may contain one to four OQ. [Chemical formula 75]

In the chemical formula 75, R ₃₅ to R ₄₂ may each independently be a hydrogen atom or a substituted or unsubstituted alkyl group, n41 and n42 may each independently be an integer of 1 to 5, such as 2 to 4, and Q may Same as defined in Chemical Formula 71.

Based on 100 parts by weight of the alkali-soluble resin, the content of the photosensitive quinone diazide compound may be 1 part by weight to 50 parts by weight, for example, 1 part by weight to 30 parts by weight. When the photosensitive quinone diazoxide compound is included in the range, a pattern is formed well without residue by exposure, and film thickness loss during development can be prevented and thus a good pattern can be provided.

(D) Solvent

The photosensitive resin composition includes a solvent capable of easily dissolving each component, such as a compound represented by Chemical Formula 1, an alkali-soluble resin, a photosensitive quinone diazide compound, and other additives to be described later.

The solvent can be an organic solvent, specifically, N-methyl-2-pyrrolidone, gamma-butyrolactone (gamma-butyrolactone), N,N-dimethyl acetamide, dimethyl sulfide, diethylene glycol Dimethyl ether, 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-butanediol acetate, 1,3-butanediol-3-monomethyl ether, methyl pyruvate, ethyl pyruvate, methyl-3-methoxy propionate or its Combination, but not limited to this.

The solvent can be appropriately selected depending on the process of forming the photosensitive resin layer such as spin coating, slot die coating, and the like.

Based on about 100 parts by weight of the alkali-soluble resin, the solvent may be used in an amount of 100 parts by weight to 300 parts by weight, for example, 100 parts by weight to 250 parts by weight. When a solvent in the range is used, a film having a sufficient thickness can be obtained, and solubility and coating properties can be improved.

(E) Other additives

The photosensitive resin composition according to an embodiment may further include other additives.

The photosensitive resin composition may further contain other additives, such as diacids (such as malonic acid), alkanolamines (such as 3-amino-1,2-propanediol), leveling agents, silane coupling agents, surfactants, cyclic Oxygen compounds, radical polymerization initiators, thermal latent acid generators, or combinations thereof, in order to prevent stains or spots, adjust leveling properties, or prevent residues due to non-development during coating. The amount of additives can be adjusted according to the required characteristics.

For example, the silane coupling agent may have reactive substituents such as vinyl groups, carboxyl groups, methacryloxy groups, isocyanate groups, epoxy groups and the like in order to improve the close contact properties with the substrate.

Examples of silane coupling agents can be trimethoxysilyl benzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyl triethoxysilane, vinyl trimethoxysilane, γ-isocyanate Propyl triethoxy silane, γ-glycidoxy propyl trimethoxy silane, β-(3,4-epoxycyclohexyl) ethyl trimethoxy silane and the like, and can be used alone or in two Use in the form of a mixture of one or more than two.

Based on 100 parts by weight of the photosensitive resin composition, the content of the silane coupling agent may be 0.01 parts by weight to 10 parts by weight. When the silane coupling agent is included in the range, the close contact property, storage ability, and the like are improved.

For example, a surfactant is added to prevent strain of the film thickness or improve developability, and the surfactant may include a fluorine-based surfactant and/or a silicone-based surfactant.

Examples of fluorine-based surfactants may be commercially available fluorine-based surfactants, such as: BM-1000 ^® and BM-1100 ^® (BM Chemie Inc.); MEGAFACE F 142D ^® , F 172 ^® , F 173 ^® , F 183 ^® and F 554 ^® (Dainippon Ink Kagaku Kogyo Co., Ltd.); FULORAD FC-135 ^® , Fowlerard FC-170C ^® , Fowlerard FC-430 ^® and Fowlerard FC-431 ^® (Sumitomo 3M Co., Ltd.); SURFLON S-112 ^® , Sauron S-113 ^® , Sauron S-131 ^® , Sauron S-141 ^® and Sauron S-145 ^® (Asahi Glass Co., Ltd.); and SH-28PA ^® , SH-190 ^® , SH-193 ^® , SZ-6032 ^® and SF-8428 ^® and the like (Toray Silicone Co., Ltd.).

Silicone surfactants can be BYK-307, BYK-333, BYK-361N, BYK-051, BYK-052, BYK-053, BYK-067A, BYK-077, BYK-301, BYK-322, BYK- 325, BYK-378 and the like, which are manufactured by BYK Chem and are commercially available.

The surfactant may be used in an amount of 0.001 parts by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is included in the range, coating uniformity can be ensured, stains may not be generated, and the wetting on the ITO substrate or the glass substrate can be improved.

The photosensitive resin composition may further contain epoxy compounds and the like for improving close contact force as additives. The epoxy compound can be epoxy novolac acrylic carboxylate resin, o-cresol novolac epoxy resin, phenol novolac epoxy resin, tetramethyl biphenyl epoxy resin, bisphenol A epoxy resin, grease Cyclo epoxy resin or a combination thereof.

When an epoxy compound is further included, a radical polymerization initiator such as a peroxide initiator or an azobis-based initiator may be further included.

The epoxy compound may be used in an amount of 0.01 parts by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is included in the range, storage capacity, close contact force, and other characteristics can be improved.

The photosensitive resin composition may further include a thermal latent acid generator. Examples of the thermal latent acid generator may be: arylsulfonic acid, such as p-toluenesulfonic acid or benzenesulfonic acid; perfluoroalkylsulfonic acid, such as trifluoromethanesulfonic acid or trifluorobutanesulfonic acid; alkylsulfonic acid, For example, methanesulfonic acid, ethanesulfonic acid or butanesulfonic acid; or a combination thereof, but not limited thereto.

The thermal latent acid generator is a catalyst for the dehydration reaction and the cyclization reaction of the polybenzoxazole precursor (ie, polyamide containing phenolic hydroxyl group), and therefore, the cyclization reaction can be performed smoothly even if the curing temperature is lowered .

In addition, unless performance is degraded, the photosensitive resin composition according to an embodiment may further include a predetermined amount of other additives such as antioxidants, stabilizers, and the like.

Another embodiment provides a photosensitive resin layer manufactured by exposing, developing, and curing the photosensitive resin composition.

The method of manufacturing the said photosensitive resin layer is as follows.

(1) Coating and layer formation

Use a spin coating method or a slit coating method, a roll coating method, a screen printing method, an applicator method, and the like to coat a photosensitive resin composition on a substrate subjected to a predetermined pretreatment (such as a glass substrate or an ITO substrate) To a desired thickness, and then the coated substrate is heated at a temperature ranging from 70°C to 150°C for 1 minute to 10 minutes to remove the solvent and form a layer.

(2) Exposure

After placing a mask having a predetermined shape, the obtained photosensitive resin layer is irradiated with active rays of 200 nm to 500 nm to form a desired pattern. Irradiation is performed by using light such as a mercury lamp, a metal halide lamp, an argon laser, etc. having low pressure, high pressure, or ultrahigh pressure. X-rays, electrons, and the like can also be used as needed.

The amount of exposure depends on the type of each component of the composition, its combination ratio and the thickness of the dry film. However, when using a high-pressure mercury lamp, it is less than or equal to 500 millijoules/square centimeter (mJ/cm ² ) (by 365 nm Sensor).

(3) Development

In the development method, after the exposure step, the exposed part is dissolved and removed by using a developing solution, leaving only the unexposed part to obtain a pattern.

(4) Post-processing process

The image pattern obtained by development in the above process is post-heated to obtain a pattern with improved heat resistance, light resistance, close contact properties, crack resistance, chemical resistance, high strength, and storage stability. For example, after development, the pattern can be heated in a convection oven at 250°C for 1 hour.

In the following, examples of this case are described. However, these examples are not construed as limiting the scope of the present invention in any sense.

( Instance )

( Alkali-soluble resin : Polybenzoxazole Synthesis of precursors )

Preparation example 1

Dissolve 67 grams of 2,2-bis(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane in 370 grams of N-methyl in a four-neck flask -2-pyrrolidone (N-methyl-2-pyrrolidone, NMP) while nitrogen passes through it. The four-neck flask is equipped with a stirrer, a temperature controller, a nitrogen injector and a condenser.

When the solid was completely dissolved, 26 grams of pyridine was added as a catalyst, and another solution prepared by dissolving 49 grams of 4,4'-oxydibenzoyl chloride in 370 grams of NMP was in a dropwise manner Add slowly to the four-neck flask for 30 minutes while keeping the temperature at 0°C to 5°C. After the addition is complete, the reaction is performed at 0°C to 5°C for 1 hour, and after the temperature is raised to room temperature, the reaction is further performed for 3 hours.

7.5 g of 5-norbornene-2,3-dicarboxylic anhydride was added thereto, and after the resulting mixture was stirred at 80°C for 24 hours, the reaction was completed. The reaction mixture was placed in a solution of water/methanol=10/1 (volume ratio) to produce a precipitate, and the precipitate was filtered, washed sufficiently with water, and vacuum dried at 80°C for more than or equal to 24 hours to obtain polybenzoxone Azole precursors.

(Preparation of photosensitive resin composition)

Instance 1

[化學式A]

在化學式A中，Q¹ 、Q² 以及Q³ 中的兩個經

取代，以及另一個為氫原子。30 g of the polybenzoxazole precursor according to Preparation Example 1 was added to 52 g of gamma-butyrolactone (gamma-butyrolactone, GBL) dissolved in it as a solvent, and 1.5 g of it was represented by chemical formula 2. Compound (1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-ol, Chemtek Product List), 4.5 g of the photosensitive compound with the structure of formula A Quinone diazide compound (MIPHOTO TPA517, Miwon Commercial Co., Ltd), 0.6 g of silane coupling agent (KBM-573; Shin-Etsu Chemical Co., Ltd.) , Ltd)) and 0.009 grams of silicone surfactants (BYK-378; BYK Chemicals) were added and dissolved in it, and the solution was filtered with a 0.45 micron fluororesin screening program to obtain a photosensitive resin composition. [Chemical formula 2]

[Chemical formula A]

In chemical formula A, two of Q ¹ , Q ² and Q ³ are

Substitution, and the other is a hydrogen atom.

Instance 2

The photosensitive resin composition was prepared according to the same method as in Example 1, except that 3 g (instead of 1.5 g) of the compound represented by Chemical Formula 2 and 55 g (instead of 52 g) of γ-butyrolactone were used (GBL).

Example 3

The photosensitive resin composition was prepared according to the same method as in Example 1, except that 4.5 g (instead of 1.5 g) of the compound represented by Chemical Formula 2 was used, and 57 g (instead of 52 g) of γ-butyrolone Esters (GBL).

Example 4

A photosensitive resin composition was prepared according to the same method as in Example 1, except that the compound represented by Chemical Formula 3 (4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl) Ethyl]phenol, Aldrich), in place of the compound represented by Chemical Formula 2. [Chemical formula 3]

Example 5 A photosensitive resin composition was prepared according to the same method as Example 4, except that 3 g (instead of 1.5 g) of the compound represented by Chemical Formula 3 was used, and 55 g (instead of 52 g) of γ- Butyrolactone (GBL).

Example 6 A photosensitive resin composition was prepared according to the same method as Example 4, except that 4.5 g (instead of 1.5 g) of the compound represented by Chemical Formula 3 was used, and 57 g (instead of 52 g) of γ- Butyrolactone (GBL).

Example 7 A photosensitive resin composition was prepared according to the same method as Example 1, except that the compound represented by Chemical Formula 4 (4-hydroxy-α,α-bis(trifluoromethyl)-cyclohexanemethanol, SMS ) Substitute the compound represented by Chemical Formula 2. [Chemical formula 4]

Example 8 A photosensitive resin composition was prepared according to the same method as Example 7, except that 3 g (instead of 1.5 g) of the compound represented by Chemical Formula 4 was used, and 55 g (instead of 52 g) of γ- Butyrolactone (GBL).

Example 9 A photosensitive resin composition was prepared according to the same method as Example 7, except that 4.5 g (instead of 1.5 g) of the compound represented by Chemical Formula 4 was used, and 57 g (instead of 52 g) of γ- Butyrolactone (GBL).

Example 10 A photosensitive resin composition was prepared according to the same method as Example 1, except that the compound represented by Chemical Formula 5 (2-benzyl-1,1,1,3,3,3-hexafluoro-2 -Propanol, Chemieliva Pharmaceutical Product List (Chemieliva Pharmaceutical Product List) replaces the compound represented by Chemical Formula 2. [Chemical formula 5]

Example 11 A photosensitive resin composition was prepared according to the same method as Example 10, except that 3 g (instead of 1.5 g) of the compound represented by Chemical Formula 5 was used, and 55 g (instead of 52 g) of γ- Butyrolactone (GBL).

Example 12 A photosensitive resin composition was prepared according to the same method as Example 10, except that 4.5 g (instead of 1.5 g) of the compound represented by Chemical Formula 5 was used, and 57 g (instead of 52 g) of γ- Butyrolactone (GBL).

Example 13 A photosensitive resin composition was prepared according to the same method as Example 1, except that the compound represented by Chemical Formula 6 (2-methyl-α,α-bis(trifluoromethyl)-benzyl alcohol, Shanghai Chemical Industry The product list (Shanghai Chemhere Product List) replaces the compound represented by Chemical Formula 2. [Chemical formula 6]

Example 14 A photosensitive resin composition was prepared according to the same method as Example 13, except that 3 g (instead of 1.5 g) of the compound represented by Chemical Formula 6 was used, and 55 g (instead of 52 g) of γ- Butyrolactone (GBL).

Example 15 A photosensitive resin composition was prepared according to the same method as Example 13, except that 4.5 g (instead of 1.5 g) of the compound represented by Chemical Formula 6 was used, and 57 g (instead of 52 g) of γ- Butyrolactone (GBL).

Comparative Example 1 prepared a photosensitive resin composition according to the same method as Example 1, except that the compound represented by Chemical Formula 2 was not used, and 51 g (instead of 52 g) of γ-butyrolactone (GBL) was used.

Comparative Example 2 A photosensitive resin composition was prepared according to the same method as Example 1, except that the compound represented by the chemical formula C-1 (2-(bicyclo[2.2.1]heptane-5-en-2-yl (Methyl)-1,1,1,3,3,3-hexafluoro-2-propanol, Aldrich) instead of the compound represented by Chemical Formula 2. [Chemical formula C-1]

Comparative Example 3 prepared a photosensitive resin composition according to the same method as in Example 1, except that the compound represented by the chemical formula C-2 (Cas No.: 1965-09-9, 1717, CheMall) was used instead of The compound represented by Chemical Formula 2. [Chemical formula C-2]

Evaluation 1 : Sensitivity assessment

The photosensitive resin compositions according to Examples 1 to 15 and Comparative Examples 1 to 3 were respectively coated on an 8-inch wafer and heated on a hot plate at 120° C. for 4 minutes to form a 10 micron thick film. The film was subjected to the following operations: while changing the exposure amount by using masks with different sizes of patterns, exposure was performed with an i-line stepper (NSR i11D, Nikon Corp); at room temperature 2. Developed in 38% TMAH aqueous solution for 50/50 seconds (2 coverings) to dissolve the exposed part; and washed with pure water for 30 seconds to form a pattern. The film was cured at 280°C for 60 minutes under a nitrogen atmosphere.

Each thickness of the film was measured by using ST-5000 (K-MAC Corp), and its CD was measured using S-9260 (Hitachi Ltd). The sensitivity was evaluated by measuring the exposure of the 7-micron perforation pattern and the CD. The results are shown in Table 1.

Evaluation 2 : Mechanical properties

Each photosensitive resin composition according to Examples 1 to 15 and Comparative Examples 1 to 3 was spin-coated on a glass plate, and heat-treated in an oven at 180°C for 60 minutes, and then at 300°C under a stream of nitrogen Heat treatment for 60 minutes to form a 10 micron film, and form an outer sheath on the edge for peeling off the film with water. The peeling film was dried at 100° C. for 30 minutes to remove water, and then the film was cut into a size of 100 mm×10 mm with reference to ASTM-D882. UTM analysis was used to measure elongation at break, and the results are shown in Table 1. [Table 1]

According to Table 1, by using a compound having a specific structure as a dissolution control agent, the photosensitive resin composition according to an example exhibits improved sensitivity.

Although the present invention has been described in conjunction with what is currently regarded as a practical example of the exemplary embodiment, it should be understood that the present invention is not limited to the disclosed embodiments, but on the contrary, the present invention intends to cover the spirit and spirit included in the scope of the attached application. Various modifications and equivalent configurations within the scope. Therefore, the above-mentioned embodiments should be understood as exemplary but not limiting the present invention in any way.

no.

no.

no.

Claims (9)

A photosensitive resin composition comprising: (A) an alkali-soluble resin, wherein the alkali-soluble resin is a polybenzoxazole precursor, a polyimide precursor or a combination thereof; (B) a photosensitive quinone diazide compound (C) a compound represented by Chemical Formula 1, wherein the content of the compound represented by Chemical Formula 1 is 1 to 30 parts by weight based on 100 parts by weight of the alkali-soluble resin; and (D) a solvent:

Wherein, in the chemical formula 1, L ¹ is a single bond or a substituted or unsubstituted C1 to C20 alkylene group, and R ¹ is a substituted or unsubstituted C3 to C20 aliphatic cyclic group or a substituted or unsubstituted C3 to C20 aliphatic cyclic group A substituted C6 to C20 aromatic ring group, provided that the aliphatic ring group does not include an unsaturated bond, and R ² to R ⁴ are each independently a hydroxyl group or a C1 to C10 trifluoroalkyl group, provided that R ² At least one of to R ⁴ is a hydroxyl group and at least one of R ² to R ⁴ is a C1 to C10 trifluoroalkyl group. The photosensitive resin composition according to claim 1, wherein R ¹ is a substituted or unsubstituted C3 to C20 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group. The photosensitive resin composition according to the first item of the patent application, wherein R ¹ is an unsubstituted C3 to C20 cycloalkyl group, a C3 to C20 cycloalkyl group substituted with a C1 to C10 alkyl group, and a hydroxyl group substituted C3 to C20 cycloalkyl, unsubstituted C6 to C20 aryl, C6 to C20 aryl substituted with C1 to C10 alkyl, or C6 to C20 aryl substituted with hydroxy. The photosensitive resin composition as described in claim 1, wherein R ² and R ⁴ are each independently a C1 to C10 trifluoroalkyl group, and R ³ is a hydroxyl group. The photosensitive resin composition according to item 1 of the patent application, wherein the compound represented by Chemical Formula 1 is represented by one of Chemical Formula 2 to Chemical Formula 6:

[Chemical formula 4]

The photosensitive resin composition according to item 1 of the scope of patent application, wherein based on 100 parts by weight of the alkali-soluble resin, the photosensitive resin composition includes: 1 part by weight to 50 parts by weight of the photosensitive resin A quinone diazide compound; 1 part by weight to 30 parts by weight of the compound represented by Chemical Formula 1; and 100 parts by weight to 300 parts by weight of the solvent. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition further includes an additive selected from the group consisting of diacids, alkanolamines, leveling agents, silane coupling agents, and surface active agents. Agents, epoxy compounds, radical polymerization initiators, thermal latent acid generators, and combinations thereof. A photosensitive resin layer manufactured using the photosensitive resin composition described in any one of the first to seventh items in the scope of the patent application. An electronic device comprising the photosensitive resin layer as described in item 8 of the scope of patent application.