CN110989294B - Photosensitive resin composition, photosensitive resin layer, and electronic device - Google Patents
Photosensitive resin composition, photosensitive resin layer, and electronic device Download PDFInfo
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- CN110989294B CN110989294B CN201910924208.5A CN201910924208A CN110989294B CN 110989294 B CN110989294 B CN 110989294B CN 201910924208 A CN201910924208 A CN 201910924208A CN 110989294 B CN110989294 B CN 110989294B
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/008—Azides
- G03F7/0085—Azides characterised by the non-macromolecular additives
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
Abstract
The invention discloses a photosensitive resin composition, a photosensitive resin layer and an electronic device comprising the photosensitive resin layer, wherein the photosensitive resin composition comprises the following components: (a) an alkali-soluble resin; (B) a photosensitive diazoquinone compound; (C) A dissolution controlling agent comprising a first phenolic resin represented by chemical formula 1 and a second phenolic resin represented by chemical formula 2; and (D) a solvent, wherein the first phenolic resin and the second phenolic resin are included in a weight ratio of 10:90 to 30:70. In chemical formula 1 and chemical formula 2, each substituent is the same as defined in the specification.
Description
Cross-reference to related applications
The present application claims priority and rights of korean patent application No. 10-2018-011787 filed on the korean intellectual property office on day 10 and 2 of 2018, the entire contents of which are incorporated herein by reference.
Technical Field
The present disclosure relates to a photosensitive resin composition, a photosensitive resin layer using the same, and an electronic device.
Background
Polyimide resins, polybenzoxazole (polybenzoxazole) resins, and the like having improved heat resistance, electrical characteristics, and mechanical characteristics have been widely used for surface protective layers and interlayer insulating layers used in materials for display device panels and semiconductor devices. Because of the low solubility of these resins in various solvents, these resins are provided in compositions in which their precursors are dissolved in the solvent.
In recent years, the occurrence of environmental problems has demanded countermeasures against de-organic solvents, and various types of heat-resistant photosensitive resin materials which can be produced with an aqueous alkali solution in the same manner as in photoresists (photoresists) have been proposed.
Among them, a method has been proposed of using a photosensitive resin composition comprising a mixture of a hydroxypolyamide (polybenzoxazole precursor) resin, which is a heat-resistant resin after heat curing, soluble in an aqueous alkali solution and a photoacid generator such as a naphthoquinone diazide (naphthoquinone diazide) compound.
The photosensitive mechanism of the photosensitive resin composition utilizes exposing a photosensitive dinitroquinone (diazoquinone) compound to a dinitrobenzoquinone compound (i.e., photosensitive dinitroquinone compound) and a Polybenzoxazole (PBO) precursor in an unexposed portion, and thereby converting the photosensitive dinitroquinone compound into an indenecarboxylic acid (indene carboxylic acid) compound to increase the dissolution rate in an aqueous alkali solution. The difference in dissolution rate between the exposed and unexposed portions can be used to produce a relief pattern (relief pattern) made up of unexposed portions.
The photosensitive resin composition may be formed into a positive relief pattern by exposure to an aqueous alkali solution and development. Furthermore, the heat-curable film characteristics can be obtained by heating.
When the cured film is applied to a semiconductor device as a surface protective layer and an interlayer insulating layer, the cured film is required to have high reliability. Although there are many metrics to evaluate reliability, sensitivity and residual characteristics are particularly important. In addition, the cured relief pattern should have good shape, adequate alkali solubility, a small amount of residual film upon development, and excellent intimate contact characteristics with the substrate.
Disclosure of Invention
Embodiments provide a photosensitive resin composition having improved film residue ratio, sensitivity, and residue characteristics.
Another embodiment provides a photosensitive resin layer manufactured using the photosensitive resin composition.
Yet another embodiment provides an electronic device including a photosensitive resin layer.
Embodiments provide a photosensitive resin composition including: (a) an alkali-soluble resin; (B) a photosensitive diazoquinone compound; (C) A dissolution controlling agent comprising a first phenolic resin represented by chemical formula 1 and a second phenolic resin represented by chemical formula 2; and (D) a solvent, wherein the first phenolic resin and the second phenolic resin are included in a weight ratio of 10:90 to 30:70.
[ chemical formula 1]
[ chemical formula 2]
In the chemical formula 1 and the chemical formula 2,
R 1 to R 3 Each independently is a hydroxyl group or a substituted or unsubstituted C1 to C5 alkyl group,
p, q and r are each independently integers in the range of 0 to 3, and
a. b and c are each independently positive integers.
The second phenolic resin may be a block copolymer, a surrogate copolymer or a random copolymer.
The dissolution controlling agent may be contained in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the alkali-soluble resin.
The alkali-soluble resin may be a polyhydroxyamide (polyhydroxyamide) resin.
The photosensitive resin composition may contain 1 to 100 parts by weight of the photosensitive diazonium quinone compound, 0.1 to 20 parts by weight of the dissolution controlling agent, and 100 to 500 parts by weight of the solvent, based on 100 parts by weight of the alkali-soluble resin.
The photosensitive resin composition may further comprise the following additives: a dissolution control agent having a different structure than the first phenolic resin and the second phenolic resin, a sensitivity enhancer, a crosslinker, a diacid, an alkanolamine, a leveling agent, a coupling agent, a surfactant, an epoxy compound, a free radical polymerization initiator, a thermal latent acid generator, or a combination thereof.
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 encompassed in the following detailed description.
The photosensitive resin composition according to the embodiment can simultaneously improve film residue rate, sensitivity, and residual characteristics by the dissolution controlling agent comprising two different phenolic resins mixed in a specific ratio.
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are illustrative, the invention is not limited thereto and the invention is defined by the scope of the claims.
In the present specification, when no specific definition is provided otherwise, "alkyl" means C1 to C20 alkyl, "alkenyl" means C2 to C20 alkenyl, "cycloalkenyl" means C3 to C20 cycloalkenyl, "heterocycloalkenyl" means C2 to C20 heterocycloalkenyl, "aryl" means C6 to C20 aryl, "aralkyl" means C7 to C20 aralkyl, "alkylene" means C1 to C20 alkylene, "arylene" means C6 to C20 arylene, "alkylaryl" means C7 to C20 alkylarylene, "heteroaryl" means C5 to C20 heteroarylene, and "alkyleneoxy" means C1 to C20 alkyleneoxy.
In the present specification, when a specific definition is not otherwise provided, "substituted" means that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: a halogen atom (F, cl, br, or I), a hydroxyl group, a C1 to C20 alkoxy group, a nitro group, a cyano group, an amine group, an imino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamoyl group, a thiol group, an ester group, an ether group, a carboxyl group, or a salt thereof, a sulfonic acid group, or a salt thereof, a phosphoric acid group, or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C6 to C20 aryl group, a C3 to C20 cycloalkyl group, a C3 to C20 cycloalkenyl group, a C3 to C20 cycloalkynyl group, a C2 to C20 heterocycloalkyl group, a C2 to C20 heterocycloalkenyl group, a C2 to C20 heterocycloalkynyl group, a C5 to C20 heteroaryl group, or a combination thereof.
In the present specification, "hetero" means that at least one heteroatom of N, O, S and P is contained in a chemical formula when a specific definition is not otherwise provided.
In the present specification, "(meth) acrylate" means "acrylate" and "methacrylate" when a specific definition is not otherwise provided.
In the present specification, "combination" means mixing or copolymerization when no definition is provided otherwise. In addition, "copolymerization" refers to block copolymerization, alternative copolymerization, or random copolymerization, and "copolymer" refers to block copolymer, alternative copolymer, or random copolymer.
In the present specification, when a specific definition is not otherwise provided, an unsaturated bond includes a bond between other atoms, such as a carbonyl bond or an azo bond, and a multivalent bond (multi-bond) between carbon-carbon atoms.
In this specification, when a definition is not otherwise provided, when a chemical bond is not drawn at a position to be given in a chemical formula, hydrogen is bonded at the position.
In addition, in the present specification, when a definition is not otherwise provided, the term "onium" refers to a linking point (linking point) of the same or different atoms or chemical formulas.
A photosensitive resin composition according to an embodiment includes: (a) an alkali-soluble resin; (B) a photosensitive diazoquinone compound; (C) A dissolution controlling agent comprising a first phenolic resin and a second phenolic resin; and (D) a solvent, wherein the first phenolic resin is a polymer represented by chemical formula 1 and the second phenolic resin is a copolymer represented by chemical formula 2, and the first phenolic resin and the second phenolic resin are included in a weight ratio of 10:90 to 30:70.
[ chemical formula 1]
[ chemical formula 2]
In the chemical formula 1 and the chemical formula 2,
R 1 to R 3 Each independently is a hydroxyl group or a substituted or unsubstituted C1 to C5 alkyl group,
p, q and r are each independently integers in the range of 0 to 3, and
a. b and c are each independently positive integers.
When used as a protective layer or an insulating layer in a semiconductor or a display device, the photosensitive resin composition according to the embodiment is applied by coating a composition, UV exposing, developing, and curing the composition. Reliability, particularly film residue rate, sensitivity, and residue characteristics are very important for process materials, and thus the photosensitive resin composition according to an embodiment may use a dissolution controlling agent comprising a first phenolic resin and a second phenolic resin to improve both sensitivity and residue characteristics while maintaining an excellent film residue rate.
Hereinafter, each component is specifically described.
(C) Dissolution controlling agent
The dissolution controlling agent comprises two different types of phenolic resins. The phenolic resin includes a first phenolic resin represented by chemical formula 1 and a second phenolic resin represented by chemical formula 2, thereby improving sensitivity and residual characteristics while maintaining an excellent film residual rate.
In chemical formulas 1 and 2, a, b, and c refer to the number of moles and may be an integer of 1 to 1,000, for example, 1 to 500. That is, the second phenolic resin may be a copolymer in which the structural unit represented by chemical formula 2a and the structural unit represented by chemical formula 2b are contained in a molar ratio of b to c.
[ chemical formula 2a ]
[ chemical formula 2b ]
In chemical formula 2a and chemical formula 2b,
R 2 and R is 3 Each independently is a hydroxyl group or a substituted or unsubstituted C1 to C5 alkyl group, and
q and r are independently integers in the range of 0 to 3.
For example, chemical formula 1 may be represented by chemical formula 1-1, and chemical formula 2 may be represented by chemical formula 2-1.
[ chemical formula 1-1]
[ chemical formula 2-1]
In chemical formula 1-1 and chemical formula 2-1,
R 1 to R 3 Each independently is a hydroxyl group or a substituted or unsubstituted C1 to C5 alkyl group,
p, q and r are each independently integers in the range of 0 to 3, and
a. b and c are each independently positive integers.
The first phenolic resin and the second phenolic resin are included in a weight ratio of 10:90 to 30:70. When the first phenolic resin and the second phenolic resin are contained in the weight ratio range, it is easy to control the dissolution rate of TMAH, which will be described later, and at the same time improve the sensitivity and the residual characteristics while maintaining an excellent film residual rate. When the content of the first phenolic resin relative to the second phenolic resin is too small (e.g., first phenolic resin: second phenolic resin=5:95), the dissolution rate of TMAH becomes too fast and the film residue rate is uncontrollable, and as such, when the content of the first phenolic resin relative to the second phenolic resin is too large (e.g., first phenolic resin: second phenolic resin=35:65), the dissolution rate of TMAH is too slow, sensitivity is difficult to control, and accordingly, residues within the pattern may not be improved.
For example, the dissolution control agent may be included in an amount of 0.1 to 20 parts by weight, such as 1 to 15 parts by weight, such as 3 to 12 parts by weight, based on 100 parts by weight of the alkali-soluble resin. When the dissolution controlling agent is within the range, it is possible to ensure that the photosensitive resin composition has excellent sensitivity, resolution and residue removal characteristics, and a high-sensitivity pattern is formed after curing, and at the same time, heat resistance of the insulating layer can be improved.
(A) Alkali-soluble resin
The alkali-soluble resin may be a polyhydroxyamide resin, a polyimide resin, a bisphenol a resin, a bisphenol F resin, a (meth) acrylate resin, or a combination thereof.
The polyhydroxyamide resin may comprise structural units represented by chemical formula 4, and the polyimide resin may comprise structural units represented by chemical formula 5.
[ chemical formula 4]
In the chemical formula 4, the chemical formula is shown in the drawing,
X 1 is a tetravalent C6 to C30 aromatic organic radical which may be substituted or unsubstituted,
X 2 for substituted or unsubstituted divalent C6 to C30 aromatic organic radicals,
Y 1 and Y 2 Each independently is a substituted or unsubstituted C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic organic group, or a substituted or unsubstituted divalent C3 to C30 cycloaliphatic organic group, and
m1 is an integer from 2 to 1000, m2 is an integer from 0 to 500, and m 1/(m1+m2) >0.5.
[ chemical formula 5]
In the chemical formula 5, the chemical formula is shown in the drawing,
X 3 is a substituted or unsubstituted divalent C6 to C30 aromatic organic radical, a substituted or unsubstituted divalent C1 to C30 aliphatic organic radical, or a substituted or unsubstituted divalent C3 to C30 cycloaliphatic organic radical, and
Y 3 is a substituted or unsubstituted tetravalent C6 to C30 aromatic organic group, a substituted or unsubstituted tetravalent C1 to C30 aliphatic organic group, or a substituted or unsubstituted tetravalent C3 to C30 cycloaliphatic organic group.
In chemical formula 4, X 1 May be an aromatic organic group and may be a moiety derived from an aromatic diamine.
Examples of the aromatic diamine may be at least one selected from the group consisting of: 3,3 '-diamino-4, 4' -dihydroxybiphenyl, 4 '-diamino-3, 3' -dihydroxybiphenyl, bis (3-amino-4-hydroxyphenyl) propane, bis (4-amino-3-hydroxyphenyl) propane, bis (3-amino-4-hydroxyphenyl) sulfone, and bis (4-amino-3-hydroxyphenyl) sulfone, 2-bis (3-amino-4-hydroxyphenyl) -1, 3-hexafluoropropane 2, 2-bis (4-amino-3-hydroxyphenyl) -1, 3-hexafluoropropane 2, 2-bis (3-amino-4-hydroxy-5-trifluoromethylphenyl) hexafluoropropane, 2-bis (3-amino-4-hydroxy-6-trifluoromethylphenyl) hexafluoropropane, 2-bis (3-amino-4-hydroxy-2-trifluoromethylphenyl) hexafluoropropane, 2-bis (4-amino-3-hydroxy-5-trifluoromethylphenyl) hexafluoropropane, 2-bis (4-amino-3-hydroxy-6-trifluoromethylphenyl) hexafluoropropane, 2-bis (4-amino-3-hydroxy-2-trifluoromethylphenyl) hexafluoropropane, 2, 2-bis (3-amino-4-hydroxy-5-pentafluoroethyl phenyl) hexafluoropropane, 2- (3-amino-4-hydroxy-5-trifluoromethylphenyl) -2- (3-hydroxy-4-amino-5-trifluoromethylphenyl) hexafluoropropane, 2- (3-amino-4-hydroxy-5-trifluoromethylphenyl) -2- (3-hydroxy-4-amino-6-trifluoromethylphenyl) hexafluoropropane, 2- (3-amino-4-hydroxy-5-trifluoromethylphenyl) -2- (3-hydroxy-4-amino-2-trifluoromethylphenyl) hexafluoropropane, 2- (3-amino-4-hydroxy-2-trifluoromethylphenyl) -2- (3-hydroxy-4-amino-5-trifluoromethylphenyl) hexafluoropropane and 2- (3-amino-4-hydroxy-6-trifluoromethylphenyl) -2- (3-hydroxy-4-amino-5-trifluoromethylphenyl) hexafluoropropane are not limited thereto.
X 1 Examples of (a) may be a functional group represented by chemical formula 6 or chemical formula 7, but are not limited thereto.
[ chemical formula 6]
[ chemical formula 7]
In the chemical formula 6 and the chemical formula 7,
A 1 is single bond, O, CO, CR 47 R 48 、SO 2 Or S, wherein R 47 And R is 48 Each independently is a hydrogen atom or a substituted or unsubstitutedC1 to C30 alkyl, in particular C1 to C30 fluoroalkyl,
R 50 to R 52 Each independently is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 carboxyl, hydroxyl, or thiol group, and
n10 is an integer from 0 to 2, with the proviso that n11 and n12 are each independently an integer from 0 to 3.
X 2 Examples of (a) may be a functional group represented by chemical formula 8 or chemical formula 10, but are not limited thereto.
[ chemical formula 8]
[ chemical formula 10]
In the chemical formula 8 and the chemical formula 10,
R 53 、R 55 and R is 56 Each independently is a substituted or unsubstituted C1 to C30 alkyl group,
n13 is an integer of 0 to 4, n15 and n16 are each independently an integer of 0 to 3, and
A 2 is a single bond O, CR 47 R 48 CO, CONH, S or SO 2 Wherein R is 47 And R is 48 Each independently is a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group, specifically a C1 to C30 fluoroalkyl group.
In chemical formula 4, Y 1 And Y 2 May each independently be a divalent aromatic organic group, a divalent aliphatic organic group, or a divalent cycloaliphatic organic group, and may be part of a dicarboxylic acid or part of a dicarboxylic acid derivative. Specifically, Y 1 And Y 2 May each independently be a divalent aromatic organic group or a divalent cycloaliphatic organic group.
Specific examples of the dicarboxylic acid derivative may be 4,4 '-oxybenzoyl chloride (4, 4' -oxybenzoyl chloride), diphenoxydicarbonyl dichloride (diphenyloxydicarbonyl dichloride), bis (phenylcarbonyl chloride) sulfone (bis (phenylcarbonyl chloride) sulfone), bis (phenylcarbonyl chloride) ether (bis (phenylcarbonylchloride) ether), bis (phenylcarbonyl chloride) phenyl ketone (bis (phenylcarbonyl chloride) phenone), phthaloyl dichloride (phthaloyl dichloride), terephthaloyl dichloride (terephthaloyl dichloride), isophthaloyl dichloride (isophthaloyl dichloride), dicarbonyl dichloride (dicarbonyl dichloride), diphenyloxy dicarboxylate dibenzotriazole (diphenyloxy dicarboxylate dibenzotriazole), or a combination thereof, but are not limited thereto.
Y 1 And Y 2 Examples of (2) may be functional groups represented by chemical formulas 8 to 10, but are not limited thereto.
[ chemical formula 8]
[ chemical formula 9]
[ chemical formula 10]
In the chemical formulas 8 to 10,
R 53 to R 56 Each independently is a substituted or unsubstituted C1 to C30 alkyl group,
n13 and n14 are each independently an integer of 0 to 4, n15 and n16 are each independently an integer of 0 to 3, and
A 2 is a single bond O, CR 47 R 48 CO, CONH, S or SO 2 Wherein R is 47 And R is 48 Each independently is a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group, specifically a C1 to C30 fluoroalkyl group.
In the process of chemical conversionIn the formula 5, X 3 Is a divalent aromatic organic group, a divalent aliphatic organic group, or a divalent cycloaliphatic organic group. Specifically, X 3 Is a divalent aromatic organic group or a divalent cycloaliphatic organic group.
Specifically, X 3 May be a moiety derived from an aromatic diamine, a cycloaliphatic diamine, or a siliceous diamine. In this context, aromatic diamines, cycloaliphatic diamines, and siliceous diamines may be used alone or in combination of two or more.
Examples of aromatic diamines may be 3,4' -diaminodiphenyl ether, 4' -diaminodiphenyl ether, 3,4' -diaminodiphenyl methane, 4' -diaminodiphenyl sulfone, 4' -diaminodiphenyl sulfide, benzidine, m-phenylenediamine, p-phenylenediamine, 1, 5-naphthalenediamine, 2, 6-naphthalenediamine, bis [4- (4-aminophenoxy) phenyl ] sulfone, bis (3-aminophenoxy) phenyl sulfone, bis (4-aminophenoxy) biphenyl, bis [4- (4-aminophenoxy) phenyl ] ether, 1, 4-bis (4-aminophenoxy) benzene, or combinations thereof, including aromatic rings substituted with alkyl groups or halogens, but are not limited thereto.
Examples of the alicyclic diamine may be 1, 2-cyclohexyldiamine, 1, 3-cyclohexyldiamine, or a combination thereof, but are not limited thereto.
Examples of the silicon diamine may be bis (4-aminophenyl) dimethylsilane, bis (4-aminophenyl) tetramethylsiloxane, bis (p-aminophenyl) tetramethyldisiloxane, bis (gamma-aminopropyl) tetramethyldisiloxane, 1, 4-bis (gamma-aminopropyl dimethylsilyl) benzene, bis (4-aminobutyl) tetramethyldisiloxane, bis (gamma-aminopropyl) tetraphenyldisiloxane, 1, 3-bis (aminopropyl) tetramethyldisiloxane, or a combination thereof, but are not limited thereto.
In chemical formula 5, Y 3 Is a tetravalent aromatic organic group, a tetravalent aliphatic organic group or a tetravalent alicyclic organic group. Specifically, Y 3 Is a tetravalent aromatic organic group or a tetravalent alicyclic organic group.
Y 3 May be a moiety derived from an aromatic acid dianhydride or an alicyclic acid dianhydride. In this context, the aromatic acid dianhydride and the alicyclic acid dianhydride may be used aloneOr in a combination of two or more.
An example of the aromatic acid dianhydride may be benzophenone tetracarboxylic dianhydride (benzophenone tetracarboxylic dianhydride) (such as pyromellitic dianhydride (pyromellitic dianhydride)); benzophenone-3, 3', 4' -tetracarboxylic dianhydrides and the like; oxydiphthalic anhydrides (oxydiphthalic dianhydride) (e.g., 4' -oxydiphthalic anhydride); biphenyltetracarboxylic dianhydride (biphthalic dianhydride) (e.g., 3', 4' -biphenyltetracarboxylic dianhydride); (hexafluoro-isopropenyl) diphthalic anhydride diphthalic dianhydride) (e.g., 4' - (hexafluoro-isopropenyl) diphthalic anhydride); naphthalene-1, 4,5, 8-tetracarboxylic dianhydride; 3,4,9,10-perylenetetracarboxylic dianhydride (3, 4,9,10-perylenetetracarboxylic dianhydride) and the like, but is not limited thereto.
Examples of the alicyclic acid dianhydride may be 1,2,3, 4-cyclobutanetetracarboxylic dianhydride, 1,2,3, 4-cyclopentanetetracarboxylic dianhydride, 5- (2, 5-dioxatetrahydrofuranyl) -3-methyl-cyclohexane-1, 2-dicarboxylic anhydride, 4- (2, 5-dioxatetrahydrofuran-3-yl) -tetralin-1,2-dicarboxylic anhydride (4- (2, 5-dioxahydrofuran-3-yl) -tetralin-1,2-dicarboxylic anhydride), bicyclooctene-2, 3,5, 6-tetracarboxylic dianhydride, bicyclooctene-1, 2,4, 5-tetracarboxylic dianhydride, and the like, but are not limited thereto.
The alkali-soluble resin may be, for example, a polyhydroxyamide resin.
The alkali-soluble resin may have a weight average molecular weight (Mw) of 3,000 g/mole to 300,000 g/mole, and specifically 5,000 to 30,000 g/mole. When the alkali-soluble resin has a weight average molecular weight (Mw) within the range, a sufficient film residual ratio can be obtained in the non-exposed portion during development with an aqueous alkali solution, and effective patterning can be performed.
(B) Photosensitive diazoquinone compound
The photosensitive diazinoquinone compound may be a compound having a 1, 2-benzoquinone diazide structure or a 1, 2-naphthoquinone diazide structure.
The photosensitive diazonium quinone compound may include at least one selected from the compounds represented by chemical formula 11 and chemical formulas 13 to 15, but is not limited thereto.
[ chemical formula 11]
In the chemical formula 11, the chemical formula is shown in the drawing,
R 31 to R 33 Each independently is a hydrogen atom or a substituted or unsubstituted alkyl group, and specifically CH 3 ,
D 1 To D 3 Each independently is OQ, wherein Q is hydrogen, a functional group represented by chemical formula 12a or a functional group represented by chemical formula 12b, provided that Q cannot be hydrogen at the same time, and
n31 to n33 are each independently integers of 1 to 5.
[ chemical formula 12a ]
[ chemical formula 12b ]
[ chemical formula 13]
In the chemical formula 13, the chemical formula is shown in the drawing,
R 34 is a hydrogen atom or a substituted or unsubstituted alkyl group,
D 4 to D 6 Each independently is OQ, wherein Q may be the same as defined in chemical formula 11, an
n34 to n36 are each independently integers of 1 to 5.
[ chemical formula 14]
In the chemical formula 14, the chemical formula (I),
A 3 is CO or CR 500 R 501 Wherein R is 500 And R is 501 Each independently is a substituted or unsubstituted alkyl group,
D 7 to D 10 Each independently is a hydrogen atom, a substituted or unsubstituted alkyl group, OQ or NHQ, wherein Q is the same as defined in chemical formula 11,
n37, n38, n39 and n40 are each independently integers from 1 to 4, and
n37+n38 and n39+n40 are each independently integers lower than or equal to 5,
with the proviso that at least one of D7 to D10 is OQ, and one aromatic ring comprises one to three OQ, and the other aromatic ring comprises one to four OQ.
[ chemical formula 15]
In the chemical formula 15, the chemical formula of the catalyst,
R 35 to R 42 Each independently is a hydrogen atom or a substituted or unsubstituted alkyl group,
n41 and n42 are each independently an integer from 1 to 5, and specifically from 2 to 4, and
q is the same as defined in chemical formula 11.
The photosensitive diazonium quinone compound may be included in an amount of 1 to 100 parts by weight, for example, 5 to 50 parts by weight, based on 100 parts by weight of the alkali-soluble resin. When the photosensitive diazoquinone compound is contained in the above range, a pattern is well formed without residues from exposure, and film thickness loss during development can be prevented and thus a good pattern can be obtained.
(D) Solvent(s)
The photosensitive resin composition may contain a solvent capable of easily dissolving each of the following components: alkali-soluble resins, photosensitive diazoquinone compounds, dissolution control agents comprising a first phenolic resin and a second phenolic resin, and the like.
The solvent may be an organic solvent, specifically, but not limited to, N-methyl-2-pyrrolidone, γ -butyrolactone, N-dimethylacetamide, dimethyl sulfoxide, 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-butylene glycol acetate, 1, 3-butylene glycol-3-monomethyl ether, methyl pyruvate, ethyl pyruvate, methyl-3-methoxy propionate, or a combination thereof.
The solvent may be appropriately selected according to a process of forming the photosensitive resin layer, such as spin coating, slot die coating (slit die coating), and the like.
The solvent may be included in an amount of 100 parts by weight to 500 parts by weight, for example, 100 parts by weight to 400 parts by weight, based on 100 parts by weight of the alkali-soluble resin. When the solvent is contained within the range, the coating layer may have a sufficient thickness, and excellent solubility and coating characteristics are improved.
(F) Other additives
The photosensitive resin composition according to the embodiment may further include other additives.
The photosensitive resin composition may contain the following additives: a dissolution controlling agent having a different structure than the first phenolic resin and the second phenolic resin, a sensitivity enhancing agent, a crosslinking agent, a diacid (e.g., malonic acid), an alkanolamine (e.g., 3-amino-1, 2-propanediol), a leveling agent, a coupling agent, a surfactant, an epoxy compound, a free radical polymerization initiator, a thermal latent acid generator, or a combination thereof, in order to prevent strain of the film during coating, to improve leveling characteristics or to prevent residue generation due to non-development. The amount of additive used may be controlled depending on the desired characteristics.
For example, the coupling agent may have reactive substituents such as vinyl, carboxyl, methacryloxy, isocyanate, epoxy, and the like groups to improve the intimate contact characteristics with the substrate.
Examples of the coupling agent may be trimethoxysilylbenzoic acid, γ -methacryloxypropyl trimethoxysilane, vinyltriacetoxy silane, vinyltrimethoxysilane, γ -isocyanatopropyl triethoxysilane, γ -glycidoxypropyl trimethoxysilane, β - (3, 4-epoxycyclohexyl) ethyl trimethoxysilane and the like, and may be used alone or in the form of a mixture of two or more.
The coupling agent may be used in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the coupling agent is contained within the range, the close contact property, the storage ability and the like are improved.
For example, a surfactant is added to prevent strain of film thickness or improve developability, and the surfactant may include a fluorine-based surfactant and/or a silicone-based surfactant.
Examples of the fluorine-based surfactant may be commercially available fluorine-based surfactants such as BM chemical company (BM Chemie inc.)And->Makefir (MEGAFACE) F ∈ of Dajaponicum ink chemical Co., ltd (Dainippon Ink Kagaku Kogyo Co., ltd.)>Meigefis F->Meigefis F->Meigefis F->Meigefield F->Fowler-Nordheim (Fulored) of Sumitomo 3M Co., ltd>Fowler-Nordheim->Fowler-Nordheim->Fowler-NordheimSoulon (SURFLON) from Asahi Glass Co., ltd>Suo LongSoulon->Soulon->Soulon->Dongli Silicone Co., ltd.>And +.>And the like.
The silicone-based surfactant may be Pick (BYK) -307, pick-333, pick-361N, pick-051, pick-052, pick-053, pick-067A, pick-077, pick-301, pick-322, pick-325, and the like, which are commercially available from Pick chemistry (BYK Chem).
The surfactant may be used in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is contained within the range, coating uniformity can be ensured, strain may not be generated, and wetting on the ITO substrate or the glass substrate is improved.
The photosensitive resin composition may further comprise an epoxy compound and the like for improving the close contact force as additives. The epoxy compound may be an epoxy novolac acrylate resin, an ortho-cresol novolac epoxy resin, a phenol novolac epoxy resin, a tetramethyl biphenyl epoxy resin, a bisphenol a epoxy resin, an alicyclic epoxy resin, or a combination thereof.
When further comprising an epoxy compound, a radical polymerization initiator such as a peroxide initiator or an azo bis-type initiator may be further included.
The epoxy compound may be used in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is contained within the range, the storage ability, the close contact force, and other characteristics can be improved.
The photosensitive resin composition may further comprise a thermal latent acid generator. Examples of the thermal latent acid generator may be: arylsulfonic acids, such as p-toluenesulfonic acid or benzenesulfonic acid; perfluoroalkyl sulfonic acids, such as trifluoromethanesulfonic acid or trifluoromethanesulfonic acid; alkylsulfonic acids, such as methanesulfonic acid, ethanesulfonic acid, or butanesulfonic acid; or a combination thereof, but is not limited thereto.
The thermal latent acid generator is a catalyst for dehydration reaction and cyclization reaction of polybenzoxazole precursors (i.e., polyamides containing phenolic hydroxyl groups), and thus the cyclization reaction proceeds smoothly even if the curing temperature is lowered.
In addition, unless the characteristics are degraded, the photosensitive resin composition according to the embodiment may further include a predetermined amount of other additives such as an antioxidant, a stabilizer, and the like.
Another embodiment provides a photosensitive resin layer produced by exposing, developing and curing the aforementioned photosensitive resin composition.
Another embodiment provides an electronic device including a photosensitive resin layer.
The electronic device may be a semiconductor device.
The method for producing the photosensitive resin layer is as follows.
(1) Coating and layer formation
A photosensitive resin composition having a desired thickness is coated on a substrate such as a glass substrate or an ITO substrate subjected to a predetermined pretreatment using a spin coating or slit coating method, a roll coating method, a screen printing method, an applicator method, and the like. Subsequently, the coated substrate is heated at a temperature ranging from 70 ℃ to 150 ℃ for 1 to 10 minutes, thereby removing the solvent and forming a layer.
(2) Exposure to light
After a mask having a predetermined shape is placed to form a desired pattern, the obtained photosensitive resin layer is irradiated with active rays of 200 nm to 500 nm. Irradiation is performed by using a light source such as a mercury lamp having a low pressure, a high pressure, or an ultra-high pressure, a metal halide lamp, an argon laser, and the like. X-rays, electron beams, and the like may also be used as needed.
The exposure dose varies depending on the type of each component of the composition, the combination ratio thereof, and the dry film thickness, but is less than or equal to 500 millijoules per square centimeter (mJ/cm) when a high pressure mercury lamp is used 2 ) (according to 365 nm sensor).
(3) Development process
In the developing method, after the exposure step, the exposed portion is dissolved and removed by using a developing solution to leave only the non-exposed portion to obtain a pattern.
(4) Post-process (Post-process) process
The image pattern obtained by development in the above-described process is post-heated so as to obtain a pattern having improved heat resistance, light resistance, close contact characteristics, crack resistance, chemical resistance, high strength, and storage stability. For example, after development, the pattern may be heated in a convection oven at 250 ℃ for 1 hour.
Hereinafter, the present invention is described in more detail with reference to examples. However, these examples should not be construed as limiting the scope of the invention in any way.
(example)
(Synthesis of alkali-soluble resin)
12.4 g of 2, 2-bis (3-amino-4-hydroxyphenyl) -1, 3-hexafluoropropane was dissolved in 125 g of N-methyl-2-pyrrolidone (NMP) in a four-necked flask equipped with a stirrer, a temperature controller, a nitrogen syringe and a condenser while passing nitrogen therethrough.
When the solid was completely dissolved, 4.2 g of pyridine was added thereto as a catalyst, and a solution prepared by dissolving 9.4 g of 4,4' -oxybenzoyl chloride in 100 g of NMP was slowly added thereto in a dropwise manner for 30 minutes while the temperature was maintained at 0 to 5 ℃. When the addition was completed, the obtained mixture was reacted at 0 to 5 ℃ for 1 hour, and after the temperature was increased to room temperature, the reaction was performed for one hour.
Subsequently, 1.1 g of 5-norbornene-2, 3-dicarboxylic anhydride (5-norbernene-2, 3-dicarboxyl anhydride) was added thereto, and the obtained mixture was stirred at 70℃for 24 hours, thereby completing the reaction. The reaction mixture was put into a solution of water/methanol=10/1 (volume ratio) to produce a precipitate, and the precipitate was filtered, washed well, and dried at 80 ℃ for 24 hours or more under vacuum, thereby obtaining a polyhydroxyamide resin.
(polymerization of dissolution controlling agent)
Polymerization example 1: first phenolic resin
1.00 mol of m-cresol, 1.50 mol of p-cresol, 1.25 mol of salicylic acid, 0.002 mol of p-toluenesulfonic acid 1 hydrate and 100 g of propylene glycol monomethyl ether were mixed and stirred in a 1.0 liter flask at 70℃to obtain a mixed solution (reaction solution). The reaction solution obtained was heated to 120 ℃ in an oil bath. The reaction solution was stirred for 5 hours at 120 ℃ and then cooled to 60 ℃. When the reaction is completed, a mixture of water and methanol is used to remove the acid.
Polymerization example 2: second phenolic resin
1.00 mol of m-cresol, 1.50 mol of p-cresol, 0.50 mol of salicylic acid, 0.75 mol of formaldehyde, 0.002 mol of p-toluenesulfonic acid 1 hydrate and 100 g of propylene glycol monomethyl ether were mixed and stirred in a 1.0 liter flask at 70℃to dissolve solids and obtain a mixed solution (reaction solution). The reaction solution obtained was heated to 120 ℃ in an oil bath. The reaction solution was stirred for 5 hours at 120 ℃ and then cooled to 60 ℃. When the reaction is completed, a mixture of water and methanol is used to remove the acid.
(preparation of photosensitive resin composition)
Examples 1 to 4 and comparative examples 1 to 4
100 g of a polyhydroxyamide resin was dissolved in 300 g of Gamma Butyrolactone (GBL) solvent, and 30 g of a photosensitive dinitroquinone compound (mipoto TPD425, m Wang Shangye corporation (Miwon com co., ltd.)), a first phenolic resin and a second phenolic resin in the weight ratio shown in table 1 were dissolved therein, and then stirred until the solutions became uniform under yellow light. Next, the resulting solution was filtered with a 0.20 μm fluororesin filter to obtain a photosensitive resin composition.
TABLE 1
| Weight ratio of | First phenolic resin | Second phenolic resin |
| Example 1 | 10 | 90 |
| Example 2 | 15 | 85 |
| Example 3 | 20 | 80 |
| Example 4 | 30 | 70 |
| Comparative example 1 | 0 | 100 |
| Comparative example 2 | 5 | 95 |
| Comparative example 3 | 35 | 65 |
| Comparative example 4 | 100 | 0 |
Evaluation of
The photosensitive resin compositions according to examples 1 to 4 and comparative examples 1 to 4 were coated on aluminum deposition wafers, respectively, and heated (cured) on a 120 ℃ heating plate for 4 minutes to form cured films of 10 μm thickness. The cured films were evaluated for film residue rate, sensitivity, and residual characteristics, and the results are shown in table 2.
(evaluation 1: film residual Rate)
The difference in thickness before/after development was calculated as a film residue ratio.
(evaluation 2: sensitivity)
After development, the exposure dose showing a pattern size of 7 μm was calculated as sensitivity.
(evaluation 3: residue (float film (scum))
-O: after development, no composition remains in the perforation pattern.
-X: after development, the composition remains in the perforation pattern.
TABLE 2
Referring to table 1, the photosensitive resin composition according to the embodiment of the present invention can simultaneously improve sensitivity and residual characteristics and maintain an excellent film residual rate by using the first phenolic resin including the structural unit represented by chemical formula 1 and the second phenolic resin including the structural unit represented by chemical formula 2 as a dissolution controlling agent in a predetermined ratio.
While the invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not to be limited to the disclosed embodiments, but on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. The above embodiments are therefore to be understood as illustrative but not limiting in any way.
Claims (8)
1. A photosensitive resin composition comprising:
(A) An alkali-soluble resin;
(B) A photosensitive diazoquinone compound;
(C) A dissolution controlling agent comprising a first phenolic resin represented by chemical formula 1 and a second phenolic resin represented by chemical formula 2; and
(D) The solvent is used for the preparation of the aqueous solution,
wherein the weight ratio of the first phenolic resin to the second phenolic resin is from 10:90 to 30:70:
[ chemical formula 1]
[ chemical formula 2]
Wherein, in chemical formula 1 and chemical formula 2,
R 1 to R 3 Each independently is a hydroxyl group or a substituted or unsubstituted C1 to C5 alkyl group,
p, q and r are each independently integers in the range of 0 to 3, and
a. b and c are each independently positive integers.
2. The photosensitive resin composition according to claim 1, wherein the second phenolic resin is a block copolymer, a substitute copolymer, or a random copolymer.
3. The photosensitive resin composition according to claim 1, wherein the dissolution control agent is contained in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the alkali-soluble resin.
4. The photosensitive resin composition according to claim 1, wherein the alkali-soluble resin is a polyhydroxyamide resin.
5. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition comprises
Based on 100 parts by weight of the alkali-soluble resin,
1 to 100 parts by weight of the photosensitive diazonium quinone compound,
0.1 to 20 parts by weight of the dissolution controlling agent, and
100 to 500 parts by weight of the solvent.
6. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition further comprises the following additives: a dissolution control agent having a different structure than the first phenolic resin and the second phenolic resin, a sensitivity enhancer, a crosslinker, a diacid, an alkanolamine, a leveling agent, a coupling agent, a surfactant, an epoxy compound, a free radical polymerization initiator, a thermal latent acid generator, or a combination thereof.
7. A photosensitive resin layer produced using the photosensitive resin composition according to any one of claims 1 to 6.
8. An electronic device comprising the photosensitive resin layer according to claim 7.
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