CN109791356A - Photosensitive polymer combination, resin film, cured film, the manufacturing method of semiconductor device and semiconductor device - Google Patents
Photosensitive polymer combination, resin film, cured film, the manufacturing method of semiconductor device and semiconductor device Download PDFInfo
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- CN109791356A CN109791356A CN201780059665.1A CN201780059665A CN109791356A CN 109791356 A CN109791356 A CN 109791356A CN 201780059665 A CN201780059665 A CN 201780059665A CN 109791356 A CN109791356 A CN 109791356A
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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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/20—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with polyhydric phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
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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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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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
- G03F7/075—Silicon-containing compounds
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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
- G03F7/16—Coating processes; Apparatus therefor
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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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
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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
- G03F7/20—Exposure; Apparatus therefor
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
The present invention provides a kind of photosensitive polymer combination, and it includes phenolic resin (A), photoacid generator (B) and solvents with biphenol structural.
Description
Technical field
The present invention relates to photosensitive polymer combination, the manufacturing method of semiconductor device, resin film, cured film and semiconductors
Device.More specifically, it is related to a kind of photosensitive polymer combination, can be used as resisting used in the manufacture of semiconductor device
Lose agent, or the precursor as the heat-resistant resin used in semiconductor component surfaces protective film or interlayer dielectric.
The application is basic CLAIM OF PRIORITY at Patent 2016-220584 of Japanese publication on November 11st, 2016,
Its content is quoted herein.
Background technique
In the past, as surface protection film and interlayer dielectric etc. used in the semiconductor element formed in electronic component
When the material that uses, proposition has various resin combinations or photosensitive composite (for example, patent document 1).
A kind of photosensitive polymer combination is recorded in patent document 1, is contained in a solvent: there is biphenyl on main chain
The phenolic resin (A) of two based structures；Photoacid generator (B)；It is anti-by above-mentioned (B) acid generated or heat and above-mentioned (A) with that can utilize
The compound (C) answered.In patent document 1, it as phenolic resin (A), records containing two based structures of biphenyl being unsubstituted
Phenolic resin.
Existing technical literature
Patent document
Patent document 1: Japanese Unexamined Patent Publication 2012-123378 bulletin
Summary of the invention
Technical problems to be solved by the inivention
The cured resin film for being used to form surface protection film and interlayer dielectric of semiconductor device etc. can be by such as lower section
Formula obtains: by photosensitive polymer combination coated in resin film is obtained on substrate, by being exposed, developing to the resin film
And pattern is formed, then carrying out heating to the resin film for having formed pattern makes its solidification.In previous photosensitive polymer combination
In, the softening point of resin film obtained is low, therefore heat resistance is low, and pattern form can deform because of heating, accordingly, there exist
The case where can not being suitably used as the surface protection film or interlayer dielectric of semiconductor device.
According to the present invention for solving above-mentioned technical problem, it is capable of providing a kind of tree being capable of forming with excellent heat resistance
Adipose membrane and the photosensitive polymer combination of cured film, the resin film being made of the photosensitive polymer combination, the resin film
Cured film and semiconductor device including the cured film and filled using photosensitive polymer combination manufacture semiconductor
The method set.For solving the means of technical problem
In order to solve the above-mentioned technical problem the present inventor has made intensive studies, as a result complete comprising with lower section
The present invention of formula.
(1) a kind of photosensitive polymer combination, it includes:
Phenolic resin (A) with biphenol structural；
Photoacid generator (B)；With
Solvent.
(2) photosensitive polymer combination according to above-mentioned (1), wherein the phenolic resin (A), which has, is originated from biphenyl
Phenolic compounds in aldehyde compound, dihydroxymethyl compound, dimethoxy methyl compound and Dihaloalkyl compound
The structural unit of at least one kind of compound.
(3) photosensitive polymer combination according to above-mentioned (1) or (2), wherein the phenolic resin (A) is that have
By the resin for the structural unit that formula (1) indicates.
(in formula (1),
R11And R12Separately for selected from hydroxyl, halogen atom, carboxyl, carbon atom number 1~20 saturation or unsaturation
Alkyl, the alkane ether of carbon atom number 1~20, the saturated or unsaturated ester ring type group of carbon atom number 3~20 or carbon atom
1 valence substituent group in the organic group with aromatic structure of number 6~20, they can by ester bond, ehter bond, amido bond or
Carbonyl bond bonding,
P and q is separately 0~3 integer,
X1And Y1It is separately singly-bound or the fatty group selected from the carbon atom number 1~10 that can have unsaturated bond
Divalent in the organic group with aromatic structure of group, the ester ring type group of carbon atom number 3~20 and carbon atom number 6~20
Substituent group,
Wherein, Y1It is bonded with any of 2 phenyl ring).
(4) photosensitive polymer combination according to any one of above-mentioned (1) to (3), wherein the phenolic resin
(A) there is the constitutional repeating unit indicated by formula (2).
(in formula (2),
The integer that m is 2~10000,
R11And R12Separately for selected from hydroxyl, halogen atom, carboxyl, carbon atom number 1~20 saturation or unsaturation
Alkyl, the alkane ether of carbon atom number 1~20, the saturated or unsaturated ester ring type group of carbon atom number 3~20 or carbon atom
1 valence substituent group in the organic group with aromatic structure of number 6~20, they can by ester bond, ehter bond, amido bond or
Carbonyl bond bonding,
P and q is separately 0~3 integer,
X1And Y1It is separately singly-bound or the fatty group selected from the carbon atom number 1~10 that can have unsaturated bond
Divalent in the organic group with aromatic structure of group, the ester ring type group of carbon atom number 3~20 and carbon atom number 6~20
Substituent group,
Wherein, Y1It is bonded with any of 2 phenyl ring).
(5) photosensitive polymer combination according to any one of above-mentioned (1) to (4), wherein the photoacid generator
It (B) is the compound that acid is generated by the irradiation of the radioactive ray of the wavelength of 200~500nm.
(6) photosensitive polymer combination according to any one of above-mentioned (1) to (5) also includes that have can be with
The crosslinking agent (C) of the group of phenolic resin (A) reaction.
(7) photosensitive polymer combination according to any one of above-mentioned (1) to (6), wherein the phenolic resin
(A) weight average molecular weight of polystyrene conversion is 1000~100000.
(8) photosensitive polymer combination according to any one of above-mentioned (1) to (7), also includes silane coupling agent
(D)。
(9) photosensitive polymer combination according to any one of above-mentioned (1) to (8), also includes nonionic table
Face activating agent (E).
(10) photosensitive polymer combination according to any one of above-mentioned (1) to (9), also includes reaction promoter
(F)。
(11) a kind of manufacturing method of semiconductor device comprising following process:
The process of photosensitive polymer combination described in any one of above-mentioned (1) to (10) is applied on a semiconductor substrate；
The process to obtain photo-sensitive resin is thermally dried to the photosensitive polymer combination；
The process that the photo-sensitive resin is exposed by activating light；
Developed to the photo-sensitive resin after the exposure come the process for obtaining patterned resin layer；With
The process to obtain curing resin layer is heated to the patterned resin layer.
(12) a kind of resin film, the photosensitive polymer combination described in any one of above-mentioned (1) to (10) are constituted.
(13) cured film of resin film described in above-mentioned (12).
(14) a kind of semiconductor device comprising cured film described in above-mentioned (13).
Invention effect
In accordance with the invention it is possible to provide the photosensitive of a kind of resin film being capable of forming with excellent heat resistance or cured film
Property resin combination, the resin film being made of the photosensitive polymer combination, the cured film of the resin film and including described
The semiconductor device of cured film and the method for manufacturing semiconductor device using the photosensitive polymer combination.
Specific embodiment
In the following, embodiments of the present invention will be described.
(photosensitive polymer combination)
Photosensitive polymer combination according to the present embodiment includes that phenolic resin (A), the light with biphenol structural produce
Sour agent (B) and solvent.
In the resin combination of present embodiment, as phenolic resin (A), the resin, i.e. with biphenol structural is used
Phenolic resin with two based structures of biphenyl for being respectively provided at least one hydroxyl in phenyl, is made of above-mentioned composition as a result,
Resin film heat resistance improve.Therefore, the resin film being made of above-mentioned photosensitive polymer combination is being exposed, is being developed
High-resolution pattern can be formed on above-mentioned resin film when carrying out pattern formation.
(phenolic resin (A))
In one embodiment, phenolic resin (A), which has, is originated from diphenol compound and is selected from aldehyde compound, dihydroxy first
The structural unit of at least one kind of compound in based compound, dimethoxy methyl compound and Dihaloalkyl compound.In other words
It says, phenolic resin (A) can be by diphenol compound and selected from aldehyde compound, dihydroxymethyl compound, dimethoxy-methyl
The reaction for closing object and at least one kind of compound in Dihaloalkyl compound obtains.
In the present specification, " structure for being originated from (substance) " refers to the structure manufactured using above-mentioned substance, includes above-mentioned knot
The case where usual method confirmation that structure is able to use in the technical field and above structure are not available logical in the technical field
Both the case where Chang Fangfa confirm.
Such phenolic resin (A) does not need many and diverse process, is able to use commercially available starting monomer manufacture, therefore can
It is manufactured with low cost photosensitive polymer combination obtained.
Phenolic resin (A) can be manufactured using arbitrary known method.As manufacturing method, for example, xenol can be enumerated
The condensation reaction of compound and aldehyde compound, dihydroxymethyl compound, dimethoxy methyl compound or Dihaloalkyl compound.
As the diphenol compound that can be used in manufacturing phenolic resin (A), 2,2 '-xenols and 4,4 '-connection can be enumerated
Phenol and their isomers.These diphenol compounds can have substituent group, as the substituent, can enumerate hydroxyl,
Halogen, carboxyl, the saturated or unsaturated alkyl of carbon atom number 1~20, the alkane ether of carbon atom number 1~20, carbon atom number 3~
20 saturated or unsaturated ester ring type group or the organic group etc. with aromatic structure of carbon atom number 6~20.
Such diphenol compound can for example be illustrated by following compound, but be not limited to these.
As by with aldehyde compound that phenolic resin (A) is generated and above-mentioned reacting for diphenol compound, first can be enumerated
Aldehyde, acetaldehyde, propionic aldehyde, neovaleraldehyde, butyraldehyde, valeral, hexanal, trioxane, glyoxal, hexamethylene aldehyde, diphenyl acetaldehyde, ethyl butyraldehyde,
Benzaldehyde, cinnamic acid, diphenyl acetaldehyde, aldehyde benzoic acid methyl esters, 3- methyl-2-butene aldehyde, glyoxalic acid, 5- norbornene -2- formaldehyde,
Malonaldehyde, butanedial, glutaraldehyde, naphthaldehyde, terephthalaldehyde etc..
As by with dihydroxymethyl compound that phenolic resin (A) is generated and above-mentioned reacting for diphenol compound, can
Enumerate bis- (methylol) butyric acid of 2,2-, 1,3-PD, 2- benzyloxy -1,3-PD, 2,2-dimethyl-1,3-propanediol,
2,2- diethyl -1,3-PD, monoacetin, 2- methyl -2- nitro-1,3-propylene glycol, 5- norbornene -2,2- bis-
Methanol, 5- norbornene -2,3- dimethanol, pentaerythrite, 2-Phenyl-1,3-propanediol, trimethylolethane, trihydroxy methyl third
Bis- (methylol) durols of alkane, 3,6-, 2- nitro-terephthalyl alcohol, 1,10- dihydroxy decane, 1,12- dihydroxy 12
Bis- (methylol) hexamethylenes of alkane, Isosorbide-5-Nitrae-, bis- (methylol) cyclohexene of Isosorbide-5-Nitrae-, bis- (methylol) adamantane of 1,6-, Isosorbide-5-Nitrae-benzene diformazan
Bis- (methylol)-Isosorbide-5-Nitrae-dimethoxy benzenes of alcohol, 1,3- benzene dimethanol, 2,6-, bis- (the methylol)-paracresol of 2,6-, the bis- (hydroxyls of 2,3-
Methyl) naphthalene, bis- (methylol) naphthalenes of 2,6-, bis- (methylol) anthracenes of 1,8-, 2,2 '-bis- (methylol) diphenyl ether, 4,4 '-bis- (hydroxyl first
Base) diphenyl ether, 4,4 '-bis- (methylol) diphenylsulfides, 4,4 '-bis- (methylol) benzophenone, 4- hydroxymethyl-benzoic acid-
4 '-hydroxymethyl phenyls, 4- hydroxymethyl-benzoic acid -4 '-hydroxymethyl aniline, 4,4 '-bis- (methylol) phenylureas, 4,4 '-bis- (hydroxyl first
Base) euphorin, bis- (methylol) anthracenes of 1,8-, 4,4 '-bis- (methylol) biphenyl, 2,2 '-dimethyl -4,4 '-is bis-
Bis- (4- hydroxymethyl phenyl) propane of (methylol) biphenyl, 2,2- etc..
As by with dimethoxy-methyl chemical combination that phenolic resin (A) is generated and above-mentioned reacting for diphenol compound
Object, for example, bis- (methoxy) butyric acid of 2,2-, 1,3- dimethoxy-methyl propane, 2- benzyloxy -1,3- dimethoxy can be enumerated
Ylmethyl propane, 2,2- dimethyl -1,3- dimethoxy-methyl propane, 2,2- diethyl -1,3- dimethoxy-methyl propane, 2,
3- dimethoxy -1- propanol acetate, 2- methyl -2- nitro -1,3- dimethoxy-methyl propane, 5- norbornene -2,2- bis-
Methoxyl group methyl esters, 5- norbornene -2,3- dimethoxy methyl esters, four (methoxy) methane, 2- phenyl -1,3- dimethoxy
Bis- (methoxy) durols of methylpropane, trimethoxy-ethane, trimethoxypropane gave, 3,6-, 2- nitro-Isosorbide-5-Nitrae-are bis-
Bis- (methoxy) hexamethylenes of (methoxy) benzene, 1,10- dimethoxy decane, 1,12- dimethoxy dodecane, Isosorbide-5-Nitrae-
Bis- (methoxy) cyclohexene of alkane, Isosorbide-5-Nitrae-, bis- (methoxy) adamantane of 1,6-, bis- (methoxy) benzene of Isosorbide-5-Nitrae-, 1,
Bis- (methoxy)-Isosorbide-5-Nitrae-dimethoxy benzenes of 3- dimethoxy-methyl benzene, 2,6-, bis- (the methoxy)-paracresol of 2,6-,
2,3- bis- (methoxy) naphthalenes, bis- (methoxy) naphthalenes of 2,6-, bis- (methoxy) anthracenes of 1,8-, 2,2 '-bis- (methoxyl groups
Methyl) diphenyl ether, 4,4 '-bis- (methoxy) diphenyl ether, 4,4 '-bis- (methoxy) diphenylsulfides, 4,4 '-is bis-
(methoxy) benzophenone, 4- methoxy methyl yl benzoic acid -4 '-methoxymethylphenyl, 4- methoxy methyl yl benzoic acid -
4 '-methoxymethylanilinepers, 4,4 '-bis- (methoxy) phenylureas, 4,4 '-bis- (methoxy) phenylcarbamic acid second
Bis- (methoxy) anthracenes of ester, 1,8-, 4,4 '-bis- (methoxy) biphenyl, 2,2 '-dimethyl -4,4 '-bis- (methoxy methyls
Base) biphenyl, bis- (4- methoxymethylphenyl) propane of 2,2- etc..
As by with Dihaloalkyl compound that phenolic resin (A) is generated and above-mentioned reacting for diphenol compound, example
Such as, xylene dichloride, dichloromethyl dimethoxy benzene, dichloromethyl durol, dichloromethyl biphenyl, dichloromethane can be enumerated
Base-biphenyl carboxylic acids, dichloromethyl-diphenyl dicarboxylic acid, dichloromethyl-methyl biphenyl, dichloromethyl-dimethyl diphenyl, dichloromethane
Bis- (chloroethyl) ethers of base anthracene, ethylene glycol, bis- (chloroethyl) ethers of diethylene glycol, bis- (chloroethyl) ethers of triethylene glycol, tetraethylene glycol are double
(chloroethyl) ether etc..
Above compound can be used alone, two or more can also be applied in combination.
By being condensed above-mentioned diphenol compound and above-mentioned polymeric composition by dehydration or dehydrohalogenation, can obtain
Catalyst can be used in phenolic resin (A), when polymerization.As acidic catalyst, for example, hydrochloric acid, sulfuric acid, nitric acid, phosphorus can be enumerated
Acid, phosphorous acid, methanesulfonic acid, p-methyl benzenesulfonic acid, dimethyl sulfate, diethyl sulfuric acid, acetic acid, oxalic acid, 1- hydroxyl ethylidene -1,1 ' -
Di 2 ethylhexyl phosphonic acid, zinc acetate, boron trifluoride, boron trifluoride phenol complex, boron trifluoride ether complex etc..As alkali
Property catalyst, for example, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, three second can be enumerated
Base amine, pyridine, 4-N,N-dimethylaminopyridine, piperidines, piperazine, Isosorbide-5-Nitrae-diazabicyclo [2.2.2] octane, 1,8- diaza
Bicyclic [5.4.0] -7- hendecene, 1,5- diazabicyclo [4.3.0] -5- nonene, ammonia, hexa etc..
When carrying out the synthetic reaction of phenolic resin (A), can according to need using organic solvent.As what is be able to use
The concrete example of organic solvent, can enumerate bis- (2- methoxy ethyl) ethers, methyl cellosolve, ethyl cellosolve, propylene glycol monomethyl ether,
Propylene glycol methyl ether acetate, diethylene glycol dimethyl ether, dimethyl ether, cyclohexanone, cyclopentanone, toluene, dimethylbenzene,
Gamma-butyrolacton, n-methyl-2-pyrrolidone etc., but it is not limited to these.
Phenolic resin (A) may be to further use above-mentioned biphenyl phenolate within the scope of the effect of the invention
Close substance obtained from the phenolic compounds other than object is polymerize.
In one embodiment, the knot indicated by formula (1) can have by the phenolic resin (A) that above compound obtains
Structure unit.
In formula (1),
R11And R12Separately for selected from hydroxyl, halogen atom, carboxyl, carbon atom number 1~20 saturation or unsaturation
Alkyl, the alkane ether of carbon atom number 1~20, the saturated or unsaturated ester ring type group of carbon atom number 3~20 or carbon atom
1 valence substituent group in the organic group with aromatic structure of number 6~20, they can by ester bond, ehter bond, amido bond or
Carbonyl bond bonding,
P and q is separately 0~3 integer,
X1And Y1It is separately singly-bound or the fatty group selected from the carbon atom number 1~10 that can have unsaturated bond
Divalent in the organic group with aromatic structure of group, the ester ring type group of carbon atom number 3~20 and carbon atom number 6~20
Substituent group,
Wherein, Y1It is bonded with any of 2 phenyl ring.
In the structural unit for the formula (1) that above-mentioned phenolic resin (A) can have, include in biphenol structural, i.e. phenyl points
Not Ju You at least one hydroxyl two based structures of biphenyl, the resin being made of as a result, the composition comprising above-mentioned phenolic resin (A)
The heat resistance of film improves.Therefore, it carries out being exposed, develop to the resin film being made of above-mentioned photosensitive polymer combination
When pattern formation, high-resolution pattern can be formed on above-mentioned resin film.
It is preferred that R11And R12It is separately hydroxyl.
It is preferred that p and q are separately 0~2 integer.
It is preferred that X1And Y1It is separately singly-bound or the fat selected from the carbon atom number 1~10 that can have unsaturated bond
Divalent substituent group in race's group and the organic group with aromatic structure of carbon atom number 6~20.
X1And Y1In " aliphatic group that can have the carbon atom number 1~10 of unsaturated bond " can be straight chain, can also
To be branch.As carbon atom number, it is also possible to 1~7, is also possible to 1~5, can also be 1~3.As aliphatic group,
When for aliphatic alkyl, alkylidene, alkenylene, alkynylene etc. can be enumerated, wherein preferably alkylidene, for example, can lift
Methylene, ethylidene, propylidene etc. out.
X1And Y1In " organic group with aromatic structure of carbon atom number 6~20 " be also possible to carbon atom number 6~
14, it is also possible to carbon atom number 6~12, is also possible to carbon atom number 6~9, can also be carbon atom number 6~8.As " fragrance
Race's structure " can enumerate phenylene, biphenyl diyl, naphthalene-diyl etc., wherein preferably phenylene.
X1And Y1In " organic group with aromatic structure of carbon atom number 6~20 " be also possible to above-mentioned " to have
Having the aliphatic group of the carbon atom number 1~10 of unsaturated bond " divalent that is mutually bonded and is formed with above-mentioned " aromatic structure " takes
Dai Ji.
More preferable X1And Y1It is separately following organic group.
In above-mentioned formula, n is 0~20, preferably 0~10.
The structural unit indicated by above-mentioned formula (1) can be by above-mentioned diphenol compound and selected from aldehyde compound, dihydroxy first
The reaction of at least one kind of compound in based compound, dimethoxy methyl compound and Dihaloalkyl compound obtains.
In the present embodiment, phenolic resin (A) substantially has the repetitive unit indicated by formula (2).
Wherein, in formula (2), the integer that m is 1~10000, R11And R12, p and q and X1And Y1With the definition phase in formula (1)
Together.
Resin with the repeat unit structure indicated by formula (2) for example can be with the structure indicated by formula (3)
Resin.
In formula (3), l and m expression ratio of components, 1+m=1,0≤1≤1,0≤m≤1,
R11’、R12’、R11”And R12”Separately for selected from hydroxyl, halogen atom, carboxyl, carbon atom number 1~20 it is full
And/or the saturated or unsaturated ester ring type base of the alkane ether of unsaturated alkyl, carbon atom number 1~20, carbon atom number 3~20
1 valence substituent group in the organic group with aromatic structure of group or carbon atom number 6~20, they can pass through ester bond, ether
Key, amido bond or carbonyl bond bonding,
P and q is separately 0~3 integer,
X1’、Y1’、X1”And Y1”Separately for singly-bound or selected from the carbon atom number 1~10 that can have unsaturated bond
The organic group with aromatic structure of aliphatic group, the ester ring type group of carbon atom number 3~20 and carbon atom number 6~20
In divalent substituent group.
Those skilled in the art can understand phenolic aldehyde from the type of used diphenol compound and polymerizable compound
The above structure of resin (A).
In one embodiment, the weight average molecular weight (polystyrene conversion) of phenolic resin (A) is 1000~100000
Range, preferably 2000~50000 range, further preferably 3000~30000 range.Weight with above range
The dissolubility of the phenolic resin (A) of average molecular weight in a solvent is excellent, and the mechanical property of resin film obtained is excellent.
(photoacid generator (B))
As long as the photosensitive polymer combination of present embodiment can incude the radioactive ray such as ultraviolet light, electron beam, X-ray
And form the composition of resin pattern, there is no particular limitation, can be the photosensitive polymer combination of minus or eurymeric.Pass through
Containing photoacid generator (B) with the resin combination of photosensitive present embodiment, such as can be used as in semiconductor device
Manufacture used in resist.
Photoacid generator used in the photosensitive polymer combination of present embodiment (B) be the illuminated radioactive ray of induction and
Generate acid compound, be by irradiate preferably the wavelength of 200~500nm, particularly preferred 350~450nm wavelength radiation
Line and generate acid compound.As concrete example, photonasty diazoquinone compound, photonasty diazo naphthoquinone chemical combination can be enumerated
The salt such as object, diaryl iodonium salt, triarylsulfonium salt or sulfonium borate, 2- nitrobenzyl ester compounds, N- imino group sulphur
Ester compound, acid imide sulfonate compound, 2,6- bis- (trichloromethyls) a 1,3,5-triazines compound, dihydropyridine chemical combination
Object etc..These can be used alone, and can also use two or more simultaneously.Wherein, preferably sensitivity and solvent solubility is excellent
Different photonasty diazoquinone compound and photonasty diazo naphthoquinone compound.As their concrete example, phenolate conjunction can be enumerated
1,2- benzoquinones, two nitrine -4- sulphonic acid ester, 1,2- naphthoquinones, two nitrine -4- sulphonic acid ester, 1,2- naphthoquinones, the two nitrine -5- sulphonic acid ester of object
Deng.
Photoacid generator (B) is used, preferably with 3 relative to 100 weight % of phenolic resin (A) with the amount of 1~100 weight %
The amount of~50 weight % uses.
(solvent)
The photosensitive polymer combination of present embodiment can be to dissolve the varnish obtained in a solvent for mentioned component
Form use.As used solvent, n-methyl-2-pyrrolidone, gamma-butyrolacton, N, N- dimethylacetamide can be enumerated
Amine, dimethyl sulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, dibutyl ethylene glycol ether, propylene glycol monomethyl ether, dipropyl
Glycol monomethyl ether, propylene glycol methyl ether acetate, methyl lactate, ethyl lactate, butyl lactate, methyl-1,3- butanediol acetic acid
Ester, 1,3-BDO -3- monomethyl ether, methyl pyruvate, ethyl pyruvate and 3- methoxy methyl propionate etc., can be used alone
It can also be used in mixed way.
The usage amount of solvent is the 50 weight % of weight %~1000, preferably relative to 100 weight % of phenolic resin (A)
100 weight of weight %~500 %.By using solvent within the above range, it is excellent that the treatability that resin sufficiently dissolves can be made
Different varnish.
(crosslinking agent (C))
The photosensitive polymer combination of present embodiment may include with the base that can be reacted with above-mentioned phenolic resin (A)
The crosslinking agent (C) of group.Resin film is made in the photosensitive polymer combination using the present embodiment comprising crosslinking agent (C), it is right
It is exposed, develop make its patterning after when being heating and curing, which passes through the acid that is generated by photoacid generator (B)
Or the effect of heat, it is crosslinked with phenolic resin (A).The resin film obtained by the photosensitive polymer combination comprising crosslinking agent, passes through
Comprising the phenolic resin (A) with above structure, the deformation of the resin film for having formed pattern when being heating and curing is inhibited.And
And there is cured film obtained excellent heat resistance, electrical characteristics and mechanical property therefore can be used as in semiconductor device
Used in surface protection film and interlayer dielectric.
As can be in crosslinking agent used in the photosensitive polymer combination of present embodiment (C), it is preferable to use can
With the compound of phenolic resin (A) heat cross-linking.As the crosslinking agent (C) that can be used, following compound can be enumerated:
(1) compound containing the crosslinkable groups selected from one or more of methylol and alkoxy methyl: for example, benzene
Dimethanol, bis- (methylol) cresols, bis- (methylol) dimethoxy benzenes, bis- (methylol) diphenyl ether, bis- (methylol) hexichol first
Ketone, hydroxymethyl-benzoic acid methylol phenyl ester, bis- (methylol) biphenyl, bis- (methylol) biphenyl of dimethyl, bis- (methoxies)
Benzene, bis- (methoxy) cresols, bis- (methoxy) dimethoxy benzenes, bis- (methoxy) diphenyl ether, bis- (methoxyl groups
Methyl) benzophenone, methoxy methyl yl benzoic acid methoxy phenyl ester, bis- (methoxy) biphenyl, the bis- (methoxies of dimethyl
Ylmethyl) biphenyl；As commercial commodity, can enumerate CYMEL 300,301,303,370,325,327,701,266,267,
238,1141,272,202,1156,1158,1123,1170,1174, UFR65,300 (three Jing Qingte Co., Ltd. (Mitsui
Cytec Co., Ltd.) production), NIKALAC MX-270, -280, -290, NIKALAC MS-11, NIKALAC MW-30, -
100, -300, -390, -750 (Sanwa Chemical Co., Ltd (Sanwa Chemical Co., Ltd.) productions), the bis- (methoxies of Isosorbide-5-Nitrae -
Ylmethyl) benzene, 4,4 '-biphenyl dimethanols, 4,4 '-bis- (methoxy) biphenyl, commercially available 26DMPC, 46DMOC, DM-
(Asahi Organic Chem Ind (ASAHI YUKIZAI CORPORATION) is raw by BIPC-F, DM-BIOC-F, TM-BIP-A
Produce), DML-MBPC, DML-MBOC, DML-OCHP, DML-PC, DML-PCHP, DML-PTBP, DML-34X, DML-EP, DML-
POP, DML-OC, dihydroxymethyl-Bis-C, dihydroxymethyl-BisOC-P, DML-BisOC-Z, DML-BisOCHP-Z, DML-PFP,
DML-PSBP, DML-MB25, DML-MTrisPC, DML-Bis25X-34XL, DML-Bis25X-PCHP, 2,6- dimethoxy first
Base -4-TBP, 2,6- dimethoxy-methyl-paracresol, 2,6- diacetoxy methyl-paracresol, TriML-P,
(the Honshu TriML-35XL, TriML-TrisCR-HAP, HML-TPPHBA, HML-TPHAP, HMOM-TPPHBA, HMOM-TPHAP
Chemical industry Co., Ltd. (HONSHU CHEMICAL INDUSTRY CO., LTD.) production) etc..These compounds can be independent
Using or be used in mixed way.
(2) with the compound of epoxy group: for example, n-butyl glycidyl ether, 2- ethoxyhexyl glycidol ether, benzene
Base glycidol ether, allyl glycidyl ether, ethylene glycol diglycidylether, propylene glycol diglycidylether, neopentyl glycol
Diglycidyl ether, glycerine polyglycidyl ether, d-sorbite polyglycidyl ether, glycidol ether of bisphenol-A (or F) etc. contract
The ethylene oxidic esters such as water glycerin ether, adipic acid 2-glycidyl ester, o-phthalic acid diglycidyl ester, 3,4- epoxycyclohexyl
Methyl (3,4- 7-oxa-bicyclo[4.1.0) carboxylate, 3,4- epoxy -6- methylcyclohexylmethyl (3,4- epoxy -6- hexahydrotoluene) carboxylic
Acid esters, bis- (3,4- epoxy -6- methylcyclohexylmethyl) adipate esters, bicyclopentane allene oxide object, bis- (2,3- epoxide rings penta
Base) ether, Co., Ltd.'s Daicel (Daicel Corporation) production CELLOXIDE 2021, CELLOXIDE 2081,
The ester ring types epoxies, 2 such as CELLOXIDE 2083, CELLOXIDE 2085, CELLOXIDE 8000, EPOLEAD GT401,2 '-
(((((1- (4- (2- (4- (ethylene oxide -2- ylmethoxy) phenyl) propane -2- base) phenyl) ethane -1,1- diyl) it is bis- (4,
1- phenylene)) bis- (oxygroups)) bis- (methylene)) bis- (ethylene oxide)) (for example, Techmore VG3101L (Printec
Corporation production)), Epolite 100MF (chemical industry Co., Ltd., common prosperity society (KYOEISHA CHEMICAL Co.,
Ltd.) produce), the aliphatic polyglycidyls such as Epiol TMP (NOF Corp (NOF CORPORATION) production)
Ether, 1,1,3,3,5,5- vegolysen, bis- (3- (ethylene oxide -2- ylmethoxy) propyl) trisiloxanes of 5- are (for example, DMS-
E09 (Gelest, Inc. production))；
(3) with the compound of isocyanate group: for example, 4,4 '-methyl diphenylene diisocyanates, toluene diisocynate
Ester, 1,3- phenylene dimethylene diisocyanate, 4,4 '-diisocyanate of dicyclohexyl methyl hydride-, isophorone diisocyanate
Ester, hexamethylene diisocyanate；
(4) with the compound of dimaleoyl imino: for example, 4,4 '-diphenyl methane bismaleimide, phenyl first
Alkane maleimide, meta-phenylene bismaleimide, bisphenol-A Diphenyl Ether Bismaleimide, 3,3 '-dimethyl -5,5 '-two
4,4 '-diphenyl methane bismaleimide of ethyl-, 4- methyl-1,3- phenylene bismaleimide, 1,6 '-spans carry out acyl
Imines-(2,2,4- trimethyl) hexane, 4,4 '-Diphenyl Ether Bismaleimides, 4,4 '-diphenyl sulfone bismaleimide, 1,
Bis- (3- maleimidephenoxy) benzene of 3-, bis- (4- maleimidephenoxy) benzene of 1,3-.
The use level of crosslinking agent (C) in photosensitive polymer combination relative to 100 weight % of phenolic resin (A), be 1~
100 weight %, preferably 5~50 weight %.When use level is 1 weight % or more, the mechanical strength of heat cured film is good, when
Use level is 100 weight % hereinafter, composition having good stability under varnish state, and the machine of heat cured film obtained
Tool intensity is good.
(silane coupling agent (D))
The photosensitive polymer combination of present embodiment may include silane coupling agent (D).By the inclusion of silane coupling agent
(D), it when by above-mentioned photosensitive polymer combination coated in resin film is obtained on substrate, is improved with the adaptation of substrate.
As silane coupling agent (D), 3- glycidoxypropyltrimewasxysilane, 3- glycidoxypropyl can be enumerated
Hydroxypropyl methyl diethoxy silane, 3- glycidoxypropyl triethoxysilane, to styryltrimethoxysilane, 3-
Methacryloxypropylmethyl dimethoxysilane, 3- methacryloxypropyl trimethoxy silane, 3- methyl-prop
Alkene methyl diethoxy silane, 3- methacryloxypropyl, 3- acryloxy third
Base trimethoxy silane, N-2- (aminoethyl) -3- aminopropyltriethoxy dimethoxysilane, N-2- (aminoethyl) -3- aminopropyl three
Methoxy silane, N-2- (aminoethyl) -3- aminopropyl triethoxysilane, 3- aminopropyl trimethoxysilane, 3- aminopropyl three
Ethoxysilane, N- phenyl -3- aminopropyl trimethoxysilane, 3- mercapto hydroxypropyl methyl dimethoxysilane, 3- mercapto propyl front three
Oxysilane, bis- (triethoxy propyl) tetrasulfide, 3- isocyanate propyl triethoxysilanes and by making with amino
Silicon compound and acid dianhydride or anhydride reaction and the silicon compound etc. that obtains, but be not limited to these.Silane coupling agent
It can be used alone or be applied in combination.
The use level of silane coupling agent (D) in photosensitive polymer combination relative to 100 weight % of phenolic resin (A),
For 0.1~30 weight %, preferably 1~20 weight %.By using silane coupling agent (D) within the above range, can take into account
With the adaptation of substrate and the keeping quality of photosensitive polymer combination.
(nonionic surfactant (E))
The photosensitive polymer combination of present embodiment may include nonionic surfactant (E).By the inclusion of non-
Ionic surfactant (E) becomes above-mentioned photosensitive polymer combination coated in screening characteristics when obtaining resin film on substrate
It obtains well, coated film in homogeneous thickness can be obtained.Moreover, the residue or pattern when can prevent from developing to coated film are floating
It rises.
The nonionic surfactant used in photosensitive polymer combination (E) is, for example, comprising fluorine-based (for example, fluorine
Change alkyl) or silanol group compound or using siloxanes key as the compound of main framing.In the present embodiment, as
Nonionic surfactant (E), more preferably using comprising fluorine system surfactant or silicone based surfactants it is non-from
Sub- property surfactant particularly preferably uses fluorine system surfactant.As fluorine system surfactant, for example, DIC plants can be enumerated
Magafac F-171, F-173, F-444, F-470, F-471, F-475, F- of formula commercial firm (DIC CORPORATION) production
482, the Novec that F-477, F-554, F-556 and F-557, Sumitomo 3M Co., Ltd. (Sumitomo 3M Limited) produce
FC4430 and FC4432 etc., but it is not limited to these.
As the use level of surfactant when using surfactant, relative to 100 matter of alkaline soluble phenolic resin
Measure part, preferably 0.01~10 weight %.
(reaction promoter (F))
The photosensitive polymer combination of present embodiment may include reaction promoter (F).By the inclusion of reaction promoter
(F), the heat cross-linking of phenolic resin (A) and crosslinking agent for including in photosensitive polymer combination can be promoted.
As reaction promoter (F), nitrogenous 5-membered heterocycles compound can be used for example or generate sour change using heat
Close object.These may be used alone, and can also use a variety of combinations.As nitrogenous five that can be used as reaction promoter (F)
Element heterocycle compound, such as pyrroles, pyrazoles, imidazoles, 1,2,3-triazoles and 1,2,4- triazoles can be enumerated.In addition, as can be used as
Reaction promoter (F) generates the compound of acid using heat, such as can enumerate sulfonium salt, salt compounded of iodine, sulfonate, phosphate, boric acid
Salt and salicylate.From the viewpoint of the curability more effectively improved under low temperature, generated using heat in sour compound, more
One or both of sulfonate and borate are preferably comprised, it is especially excellent in the case where considering the heat resistance of cured film characteristic
Choosing includes borate.
(other additives)
It in the photosensitive polymer combination of present embodiment, can according to need, do not damaging effect of the invention
In range, the addition such as dissolution accelerator, antioxidant, filler, Photoepolymerizationinitiater initiater, end-capping reagent and sensitizer is further used
Object.
(manufacturing method of cured film)
Another mode of present embodiment provides a kind of manufacturing method of semiconductor device, and it includes following processes:
The process of the photosensitive polymer combination of aforementioned present invention is applied on a semiconductor substrate；
The process to obtain photo-sensitive resin is thermally dried to the photosensitive polymer combination；
The process that the photo-sensitive resin is exposed by activating light；
Developed to the photo-sensitive resin after the exposure come the process for obtaining patterned resin layer；With
The process to obtain curing resin layer is heated to the patterned resin layer.
In the following, an example to present embodiment is illustrated.
(forming method of film)
Firstly, the photosensitive polymer combination of present embodiment is coated on supporting mass or substrate, for example, being coated in silicon
In chip, ceramic substrate, aluminum substrate, SiC wafer, GaN wafer etc..Here, substrate also includes other than unprocessed substrate
Such as the substrate of semiconductor element or display body element is formed on surface.At this point, in order to ensure being formed by pattern and bearing
The water-fast cementability of body can also apply the bonding additives such as silane coupling agent on supporting mass or substrate in advance.Photoresist
Composition coating can by using spin coater spin coated, use the spraying coating of flush coater, dipping, printing, roller coating
Apply etc. come carry out.
Then, the prebake conditions for carrying out 30~600 seconds or so at 80~140 DEG C remove solvent, to form photonasty
The film of resin combination.As remove solvent after film thickness, preferably 1~500 μm.
(exposure process)
Then, the film obtained as described above is exposed.As the activation light of exposure, can be used for example
X-ray, electron beam, ultraviolet light, luminous ray etc., optimal wavelength are 200~500nm.From the resolution ratio of pattern and treatability
From the aspect of, preferred light source wavelength is the region of the g ray of mercury vapor lamp, h ray or i ray, be can be used alone, and can also be incited somebody to action
Light of more than two kinds is used in mixed way.As exposure device, particularly preferred contact float exposer, mirror surface projection are directed at exposer
Or stepping exposer.It after exposure, can according to need, film carried out 10~300 seconds or so again at 80~140 DEG C
Heating.
(developing procedure)
Then, the film after above-mentioned exposure is carried out being developed to relief pattern (relief pattern).It is aobvious at this
In shadow process, developer solution appropriate can be used, using such as infusion process, puddle (sheathed submergence) method (puddle method),
The methods of rotation spray coating is developed.By development, by exposure portion (in the case where eurymeric) or unexposed portion's (the case where minus
Under) removed from film dissolution, relief pattern can be obtained.
As developer solution, can be used for example:
The inorganic bases such as sodium hydroxide, sodium carbonate, sodium metasilicate, ammonia；
The organic amines such as ethamine, diethylamine, triethylamine, triethanolamine；
The aqueous solution of the quaternary ammonium salts such as tetramethylammonium hydroxide, tetrabutylammonium hydroxide etc.；
The organic solvents such as cyclopentanone, propylene glycol monomethyl ether, propylene glycol methyl ether acetate can add in these developer solutions
Added with such as water-miscible organic solvents such as methanol, ethyl alcohol or surfactant.
Wherein, preferred tetramethylammonium hydroxide aqueous solution.The concentration of tetramethylammonium hydroxide in above-mentioned aqueous solution is preferred
For 0.5~10 mass %, further preferably 1~5 mass %.
It after development, is cleaned using flushing liquor, removes developer solution, thus, it is possible to obtain relief pattern.As flushing
Liquid, for example, can by distilled water, methanol, ethyl alcohol, isopropanol, propylene glycol monomethyl ether etc. be used alone or two or more be applied in combination.
(heating process)
Finally, solidification relief pattern (solidification can be obtained by heating to the relief pattern obtained as described above
Film).Heating temperature is preferably 150 DEG C~500 DEG C, more preferably 150 DEG C~400 DEG C.Heating time can be 15~300 points
Clock.The heat treatment can be carried out by heating plate, baking oven, the temperature lifting type baking oven for capableing of set temperature program etc..As progress
Atmosphere gas when heat treatment, can be used air, and the inactive gas such as nitrogen, argon gas also can be used.It is needing more
In the case that low temperature is heat-treated, it can use vacuum pump etc. and heated under reduced pressure.
The relief pattern obtained from the photosensitive polymer combination of present embodiment, has little or no heater
Deformation in sequence, the shape of the relief pattern before being able to maintain heating, can obtain high-resolution solidification relief pattern.
(semiconductor device)
Can by by above-mentioned solidification relief pattern be used as surface protection film, interlayer dielectric, again wiring insulating film,
The protective film of upside-down mounting sheet devices protective film, device with projection cube structure, and the manufacturer with well known semiconductor device
Process step combinations in method, to manufacture semiconductor device.As described above, the solidification relief pattern of present embodiment can be with high-resolution
Rate production, therefore, the electricity using the semiconductor device of the solidification relief pattern are excellent in reliability.
Above, embodiments of the present invention are illustrated, but these are illustration of the invention, can also be used
Various compositions other than the above.The present invention is not limited to above embodiment, in the range of can be realized the object of the invention
Deformation, improvement etc. are comprising in the present invention.
Embodiment
In the following, the present invention is specifically described by embodiment and comparative example, but the present invention is not limited to this.
(synthesis example 1)
<synthesis of phenolic resin (A-1)>
To 4 mouthfuls of the glass system round-bottomed flask with thermometer, blender, material pouring inlet and drying nitrogen ingress pipe
It is interior, add 4, the 4 '-xenols of 186.2g (1.00mol), 134.6g (0.8mol) bis- (the methylol)-paracresol of 2,6-,
After the oxalic acid dihydrate of 6.3g (0.05mol) and the gamma-butyrolacton of 327g, on one side circulate nitrogen while the round bottom burnt
Bottle is placed in oil bath the polycondensation reaction for having carried out reaction solution while reflux at 100 DEG C 6 hours.It then, will be obtained anti-
It after answering liquid to be cooled to room temperature, adds the acetone of 436g and is stirred, until becoming uniform.It later, will be in round-bottomed flask
Reaction solution dropwise addition is mixed in the water of 10L, and resin component thus is precipitated.Then, it filters out and recycles resin component be precipitated
Later, it is dried in vacuo at 60 DEG C, the phenolic resin indicated by following formula (A-1) thereby is achieved.Phenolic aldehyde tree obtained
The weight average molecular weight of rouge (A-1) is 9,800.
(in formula (A-1), the key being bonded with biphenol structural is bonded with any of 2 phenyl ring).
(synthesis example 2)
<synthesis of phenolic resin (A-2)>
To 4 mouthfuls of the glass system round-bottomed flask with thermometer, blender, material pouring inlet and drying nitrogen ingress pipe
It is interior, add 4, the 4 '-xenols of 186.2g (1.00mol), bis- (methoxy) benzene of Isosorbide-5-Nitrae-, the 7.7g of 133.0g (0.8mol)
After the dithyl sulfate of (0.05mol) and the gamma-butyrolacton of 327g, on one side circulate nitrogen while the round-bottomed flask is placed in oil
The polycondensation reaction for having carried out reaction solution while reflux at 100 DEG C 6 hours.Then, reaction solution obtained is cooling
It to room temperature, adds the acetone of 436g and is stirred, until becoming uniform.Later, by the reaction drop in round-bottomed flask
Add and be mixed in the water of 10L, resin component thus is precipitated.Then, after filtering out and recycling resin component be precipitated, 60
It DEG C is dried in vacuo, the phenolic resin indicated by following formula (A-2) thereby is achieved.Phenolic resin (A-2) obtained
Weight average molecular weight is 12,300.
(in formula (A-2), the key being bonded with biphenol structural is bonded with any of 2 phenyl ring).
(synthesis example 3)
<synthesis of phenolic resin (A-3)>
To 4 mouthfuls of the glass system round-bottomed flask with thermometer, blender, material pouring inlet and drying nitrogen ingress pipe
It is interior, add 4, the 4 '-xenols of 186.2g (1.00mol), 193.9g (0.8mol) 4,4 '-bis- (methoxy) biphenyl,
After the dithyl sulfate of 7.7g (0.05mol) and the gamma-butyrolacton of 582g, on one side circulate nitrogen while the round-bottomed flask set
The polycondensation reaction for having carried out reaction solution while reflux at 100 DEG C 6 hours.Then, by reaction solution obtained
It after being cooled to room temperature, adds the acetone of 323g and is stirred, until becoming uniform.Later, by the reaction in round-bottomed flask
Drop, which adds, to be mixed in the water of 10L, and resin component thus is precipitated.Then, after filtering out and recycling resin component be precipitated,
It is dried in vacuo at 60 DEG C, the phenolic resin indicated by following formula (A 1) thereby is achieved.Phenolic resin (A- obtained
3) weight average molecular weight is 7,000.
(in formula (A-3), the key being bonded with biphenol structural is bonded with any of 2 phenyl ring).
(synthesis example 4)
<synthesis of phenolic resin (A-4)>
To 4 mouthfuls of the glass system round-bottomed flask with thermometer, blender, material pouring inlet and drying nitrogen ingress pipe
It is interior, add 2, the 2 '-xenols of 186.2g (1.00mol), 134.6g (0.8mol) bis- (the methylol)-paracresol of 2,6-,
After the oxalic acid dihydrate of 6.3g (0.05mol) and the gamma-butyrolacton of 327g, on one side circulate nitrogen while the round bottom burnt
Bottle is placed in oil bath the polycondensation reaction for having carried out reaction solution while reflux at 100 DEG C 6 hours.It then, will be obtained anti-
It after answering liquid to be cooled to room temperature, adds the acetone of 436g and is stirred, until becoming uniform.It later, will be in round-bottomed flask
Reaction solution dropwise addition is mixed in the water of 10L, and resin component thus is precipitated.Then, it filters out and recycles resin component be precipitated
Later, it is dried in vacuo at 60 DEG C, the phenolic resin indicated by following formula (A-4) thereby is achieved.Phenolic aldehyde tree obtained
The weight average molecular weight of rouge (A-4) is 7,700.
(in formula (A-4), the key being bonded with biphenol structural is bonded with any of 2 phenyl ring).
(synthesis example 5)
<synthesis of phenolic resin (A-5)>
To 4 mouthfuls of the glass system round-bottomed flask with thermometer, blender, material pouring inlet and drying nitrogen ingress pipe
It is interior, add the penta hydroxy group biphenyl (phloroglucide) of 234.2g (1.00mol), the bis- (methoxies of Isosorbide-5-Nitrae-of 133.0g (0.8mol)
Ylmethyl) benzene, the dithyl sulfate of 7.7g (0.05mol) and 375g gamma-butyrolacton after, on one side circulate nitrogen while be directed at this
Round-bottomed flask carries out oil bath, the polycondensation reaction for having carried out reaction solution while reflux at 100 DEG C 6 hours.Then, it will be obtained
Reaction solution be cooled to room temperature after, add the acetone of 500g and be stirred, until become uniform.Later, by round-bottomed flask
Interior reaction solution dropwise addition is mixed in the water of 10L, and resin component thus is precipitated.Then, it filters out and recycles resin be precipitated
It after ingredient, is dried in vacuo at 60 DEG C, the phenolic resin indicated by following formula (A-5) thereby is achieved.Phenol obtained
The weight average molecular weight of urea formaldehyde (A-5) is 22,000.
(in formula (A-5), the key being bonded with biphenol structural is bonded with any of 2 phenyl ring).
(synthesis example 6)
<synthesis of phenolic resin (A-6)>
To 4 mouthfuls of the glass system round-bottomed flask with thermometer, blender, material pouring inlet and drying nitrogen ingress pipe
It is interior, the first of addition 4, the 4 '-xenols of 186.2g (1.00mol), the paracresol of 86.5g (0.8mol), 24.0g (0.8mol)
After the gamma-butyrolacton of aldehyde, the oxalic acid dihydrate of 11.3g (0.09mol) and 308g, on one side circulate nitrogen while by the circle
Bottom flask is placed in oil bath the polycondensation reaction for having carried out reaction solution while reflux at 100 DEG C 6 hours.Then, it will be obtained
Reaction solution be cooled to room temperature after, add the acetone of 411g and be stirred, until become uniform.Later, by round-bottomed flask
Interior reaction solution dropwise addition is mixed in the water of 10L, and resin component thus is precipitated.Then, it filters out and recycles resin be precipitated
It after ingredient, is dried in vacuo at 60 DEG C, the phenolic resin indicated by following formula (A-6) thereby is achieved.Phenol obtained
The weight average molecular weight of urea formaldehyde (A-6) is 11,000.
(in formula (A-6), the key being bonded with biphenol structural is bonded with any of 2 phenyl ring).
(synthesis example 7)
<synthesis of phenolic resin (A-2)>
To 4 mouthfuls of the glass system round-bottomed flask with thermometer, blender, material pouring inlet and drying nitrogen ingress pipe
It is interior, add 4, the 4 '-xenols of 186.2g (1.00mol), dichloro-p-xylene, the 7.7g of 140.0g (0.8mol)
After the dithyl sulfate of (0.05mol) and the gamma-butyrolacton of 327g, on one side circulate nitrogen while the round-bottomed flask is placed in oil
The polycondensation reaction for having carried out reaction solution while reflux at 100 DEG C 6 hours.Then, reaction solution obtained is cooling
It to room temperature, adds the acetone of 436g and is stirred, until becoming uniform.Later, by the reaction drop in round-bottomed flask
Add and be mixed in the water of 10L, resin component thus is precipitated.Then, after filtering out and recycling resin component be precipitated, 60
It DEG C is dried in vacuo, the phenolic resin indicated by following formula (A-2) thereby is achieved.Phenolic resin (A-2) obtained
Weight average molecular weight is 13,500.
(in formula (A-2), the key being bonded with biphenol structural is bonded with any of 2 phenyl ring).
(preparation of photosensitive polymer combination)
For embodiment 1~11 and comparative example 1~2, it is prepared for photosensitive polymer combination as follows respectively.It is first
First, each ingredient cooperated according to table 1 is dissolved in gamma-butyrolacton (GBL) and is stirred in a nitrogen atmosphere so that after blending
Viscosity become about 500mPa.s after, be filtered with 0.2 μm of the polyethylene filter in aperture, varnish shape thereby is achieved
Photosensitive polymer combination.The details of each ingredient in table 1 is as described below.Unit in table 1 is mass parts.
<(A) phenolic resin>
(A-1) phenolic resin obtained by above-mentioned synthesis example 1
(A-2) phenolic resin obtained by above-mentioned synthesis example 2 or synthesis example 7
(A-3) phenolic resin obtained by above-mentioned synthesis example 3
(A-4) phenolic resin obtained by above-mentioned synthesis example 4
(A-5) phenolic resin obtained by above-mentioned synthesis example 5
(A-6) phenolic resin obtained by above-mentioned synthesis example 6
(A-7) (Sumitomo Bakelite Co (Sumitomo Bakelite Co., Ltd.) is raw for phenol resol resins
The PR-50731 of production, polystyrene conversion weight average molecular weight (Mw)=11,000)
(A-8) phenol biphenyl aralkyl resin (it is bright and chemical conversion Co., Ltd. (MEIWA PLASTIC INDUSTRIES,
LTD. MEH-7851, the polystyrene) produced converts weight average molecular weight (Mw)=2,000)
<(B) photoacid generator>
(B-1) naphthoquinone compound of the structure of following formula (B-1)
(B-2) naphthoquinone compound of the structure of following formula (B-2)
(B-3) CPI-210S (San-Apro Ltd. production)
<(C) crosslinking agent>
(C-1) NIKALAC MX-270 (Sanwa Chemical Co., Ltd's production)
(C-2) TML-BPA (Honshu Chemical Ind's production)
(C-3) CELLOXIDE 2021P (production of Co., Ltd.'s Daicel)
<(D) silane coupling agent>
(D-1) KBM-403 (production of Shin-Etsu Chemical Co., Ltd.)
(D-2) KBM-503 (production of Shin-Etsu Chemical Co., Ltd.)
(D-3) KBM-846 (Shin-Etsu Chemical Co..Ltd. production)
<(E) surfactant>
(E-1) F444 (Dainippon Ink Chemicals's production)
<(F) thermal acid generator, hot generated base alkaline agent>
(F-1) Sun-Aid SI-150 (three new chemical industry Co., Ltd. (Sanshin Chemical Industry
Co.Ltd. it) produces)
(F-2) UCAT SA506 (San-Apro Ltd. production)
<(G) phenolic compounds>
(G-1) penta hydroxy group biphenyl
(G-2) xenol
<(H) solvent>
(H-1) gamma-butyrolacton
<evaluation -1 (measurement of softening point) of phenolic resin>
To the phenolic resin of (A-1)~(A-8), softening point is measured according to JIS K 2207.Used device is strain
The ASP-M2SP of sensible section, formula commercial firm (MEITEC CORPORATION) production.Show the result in table 1.From figure when finally solidifying
From the aspect of case retention property, the higher the better for softening point.
<evaluation -2 (alkali-soluble evaluation) of phenolic resin>
The phenolic resin of (A-1)~(A-8) is dissolved in gamma-butyrolacton and obtains resin solution.Using spin coater, by institute
After the solution of acquisition is coated on 4 inch silicon wafers, using the prebake conditions of heating plate progress 3 minutes at 120 DEG C, film is obtained
Thick about 3 μm of film.Coated film obtained is impregnated 3 points at 23 DEG C in 2.38% tetramethylammonium hydroxide aqueous solution
Clock, it is thus identified that the dissolubility of film.Show the result in table 1.
[table 1]
<-1 (Examples 1 to 8, embodiment 10~11 and comparative example 1~2) of patterning evaluation>
After using spin coater to be coated on 8 inch silicon wafers respectively the photosensitive polymer combination obtained among the above,
Using the prebake conditions of heating plate progress 3 minutes at 120 DEG C, about 9.0 μm of film thickness of film is obtained.To the film, i ray is used
Stepper (NSR-4425i of Nikon Corp (Nikon Corporation) production), passes through Toppan Printing Co., Ltd
The mask of (TOPPAN PRINTING CO., LTD.) production (test chart No.1: describes the residual figure for having 0.88~50 μm of width
Case and pierced pattern), change light exposure and is irradiated.
Then, use 2.38% tetramethylammonium hydroxide aqueous solution as developer solution, adjust developing time and carry out 2 water
Hole (sheathed submergence) formula development (puddle development) make the difference of the film thickness after prebake conditions and the film thickness after development at
For 1.0 μm thus after exposure portion dissolution is removed, with pure water rinsing 10 seconds.It utilizes to be capable of forming 100 μm of square
Lowest exposure amount+the 100mJ/cm of through-hole pattern2Energy be exposed obtained from pattern, have rated the resolution of line pattern
Rate.Table 2 is shown in using result as pattern resolution (μm).In terms of making fine wiring, resolution ratio is the smaller the better.
<-2 (embodiments 9) of patterning evaluation>
After using spin coater to be coated on 8 inch silicon wafers respectively the photosensitive polymer combination obtained among the above,
Using the prebake conditions of heating plate progress 3 minutes at 120 DEG C, about 9.0 μm of film thickness of film is obtained.To the film, i ray is used
Stepper (NSR-4425i of Nikon Corp's production), the mask (test chart produced by Toppan Printing Co., Ltd
No.1: describe residual pattern and the pierced pattern for having 0.88~50 μm of width), change light exposure and is irradiated.
Then, baking processing in 2 minutes has been carried out at 100 DEG C using heating plate.Then, using 2.38% tetramethyl hydrogen
Aqueous ammonium is aoxidized as developer solution, carries out 30 seconds × 2 times puddle (sheathed submergence) formula developments to remove exposure portion dissolution
After going, with pure water rinsing 10 seconds.It utilizes to be capable of forming the lowest exposure amount+100mJ/cm of 5 μm of line2Energy carry out
Pattern obtained from exposure has rated the resolution ratio of line pattern.Table 2 is shown in using result as pattern resolution (μm).It is making
In terms of fine wiring, resolution ratio is the smaller the better.
<resolution ratio evaluation (embodiment 1~11, comparative example 1~2) after solidification>
Heating is put into figuratum chip by what is obtained in above-mentioned patterning evaluation -1 and patterning evaluation -2
In baking oven, circulate nitrogen on one side, on one side with 5 DEG C/min from room temperature to after 200 DEG C, in this state, 200 DEG C into
Row heat treatment in 60 minutes, is cooled to room temperature.Micro- sem observation is carried out with figuratum chip to what heating terminated, is had rated
The resolution ratio of line.Table 2 is shown in using result as resolution ratio (μm) after solidification.In terms of forming fine pattern, resolution ratio is smaller more
It is good.
<production of semiconductor device>
Using surface have aluminium circuit analog element chip, be respectively applied in a manner of eventually becoming 5 μm embodiment 1~
11 and comparative example 1~2 photosensitive polymer combination after, implement pattern process and make its solidification.Later, by each chip ruler
It is very little to be split, 16Pin DIP (Dual Inline Package: dual-inline package), which is mounted on, using conductive paste uses
Lead frame on after, utilize the semiconductor encapsulating epoxy resin EME-6300H of production (Sumitomo Bakelite Co) to carry out
Seal molding has produced semiconductor device.
<reliability evaluation -1 (electrical connectivity) of semiconductor device>
The electrical connection inspection of each 10 semiconductor devices obtained by the above method is carried out,
It all will be evaluated as A that electrical connection is not undesirable in all 10 semiconductor devices,
B will be evaluated as in the presence of electrical connection is undesirable in 1 or more semiconductor device in 10 semiconductor devices.
<reliability evaluation -2 (moisture-proof) of semiconductor device>
Each 10 semiconductor devices that will be obtained by the above method, are handled 168 hours under conditions of 85 DEG C/85% humidity
Later, impregnate 10 seconds in 260 DEG C of solder baths, then, implement high temperature, high humidity pressure cooker processing (125 DEG C, 2.3atm,
100% relative humidity), check electrical connection.
It all will be evaluated as A that electrical connection is not undesirable in all 10 semiconductor devices,
It will observe that electrical connection is undesirable in 1 or more semiconductor device in 10 semiconductor devices and be evaluated as B.
In the following, showing the table 2 for recording embodiment and comparative example.
Good alkali-soluble is shown by the film that phenolic resin (A-1)~(A-6) of embodiment is formed.The film
Softening point be 180 DEG C or more.These phenolic resin for example can be as used in the manufacture in semiconductor device as a result,
Resist.
Had by the film that phenolic resin (A-1)~(A-6) photosensitive polymer combination comprising embodiment is formed good
Good patternability.Semiconductor device including the cured film, electrical connectivity is not bad, and protects under high temperature and humidity
After depositing, also there is no bad caused by the corrosion as aluminium circuit.Therefore, it is contemplated that above-mentioned cured film can be filled as semiconductor
The interlayer dielectric set.
Industrial availability
The present invention is capable of providing the photonasty tree of a kind of resin film being capable of forming with excellent heat resistance and cured film
Oil/fat composition, the resin film being made of the photosensitive polymer combination, the cured film of the resin film and including the solidification
The semiconductor device of film and the method for manufacturing semiconductor device using the photosensitive polymer combination.
Claims (14)
1. a kind of photosensitive polymer combination, characterized by comprising:
Phenolic resin (A) with biphenol structural；
Photoacid generator (B)；With
Solvent.
2. photosensitive polymer combination according to claim 1, it is characterised in that:
The phenolic resin (A), which has, to be originated from diphenol compound and is selected from aldehyde compound, dihydroxymethyl compound, dimethoxy
The structural unit of at least one kind of compound in methyl compound and Dihaloalkyl compound.
3. photosensitive polymer combination according to claim 1 or 2, it is characterised in that:
The phenolic resin (A) is the resin with the structural unit indicated by formula (1),
In formula (1),
R11And R12Separately for selected from hydroxyl, halogen atom, carboxyl, carbon atom number 1~20 saturated or unsaturated alkane
Base, the alkane ether of carbon atom number 1~20, the saturated or unsaturated ester ring type group of carbon atom number 3~20 or carbon atom number 6~
1 valence substituent group in 20 organic group with aromatic structure, they can pass through ester bond, ehter bond, amido bond or carbonyl
Key bonding,
P and q is separately 0~3 integer,
X1And Y1It is separately singly-bound or aliphatic group, carbon selected from the carbon atom number 1~10 that can have unsaturated bond
Divalent in the ester ring type group of atomicity 3~20 and the organic group with aromatic structure of carbon atom number 6~20 replaces
Base,
Wherein, Y1It is bonded with any of 2 phenyl ring.
4. photosensitive polymer combination according to any one of claim 1 to 3, it is characterised in that:
The phenolic resin (A) has the constitutional repeating unit indicated by formula (2),
In formula (2),
The integer that m is 2~10000,
R11And R12Separately for selected from hydroxyl, halogen atom, carboxyl, carbon atom number 1~20 saturated or unsaturated alkane
Base, the alkane ether of carbon atom number 1~20, the saturated or unsaturated ester ring type group of carbon atom number 3~20 or carbon atom number 6~
1 valence substituent group in 20 organic group with aromatic structure, they can pass through ester bond, ehter bond, amido bond or carbonyl
Key bonding,
P and q is separately 0~3 integer,
X1And Y1It is separately singly-bound or aliphatic group, carbon selected from the carbon atom number 1~10 that can have unsaturated bond
Divalent in the ester ring type group of atomicity 3~20 and the organic group with aromatic structure of carbon atom number 6~20 replaces
Base,
Wherein, Y1It is bonded with any of 2 phenyl ring.
5. photosensitive polymer combination according to any one of claim 1 to 4, it is characterised in that:
The photoacid generator (B) is the compound that acid is generated by the irradiation of the radioactive ray of the wavelength of 200~500nm.
6. photosensitive polymer combination according to any one of claim 1 to 5, it is characterised in that:
Also comprising the crosslinking agent (C) with the group that can be reacted with the phenolic resin (A).
7. photosensitive polymer combination according to any one of claim 1 to 6, it is characterised in that:
The weight average molecular weight of the polystyrene conversion of the phenolic resin (A) is 1000~100000.
8. photosensitive polymer combination according to any one of claim 1 to 7, it is characterised in that:
Also include silane coupling agent (D).
9. photosensitive polymer combination according to any one of claim 1 to 8, it is characterised in that:
Also include nonionic surfactant (E).
10. photosensitive polymer combination according to any one of claim 1 to 9, it is characterised in that:
Also include reaction promoter (F).
11. a kind of manufacturing method of semiconductor device, which is characterized in that including following process:
The process of photosensitive polymer combination described in any one of claims 1 to 10 is applied on a semiconductor substrate；
The process to obtain photo-sensitive resin is thermally dried to the photosensitive polymer combination；
The process that the photo-sensitive resin is exposed by activating light；
Developed to the photo-sensitive resin after the exposure come the process for obtaining patterned resin layer；With
The process to obtain curing resin layer is heated to the patterned resin layer.
12. a kind of resin film, it is characterised in that:
The photosensitive polymer combination described in any one of claims 1 to 10 is constituted.
13. a kind of cured film, it is characterised in that:
The cured film is the cured film of resin film described in claim 12.
14. a kind of semiconductor device, it is characterised in that:
Including the cured film described in claim 13.
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| CN202211513979.3A CN115718406A (en) | 2016-11-11 | 2017-11-09 | Photosensitive resin composition for forming resist, resin film, cured film, and semiconductor device |
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| JP2016220584 | 2016-11-11 | ||
| PCT/JP2017/040412 WO2018088469A1 (en) | 2016-11-11 | 2017-11-09 | Photosensitive resin composition, resin film, cured film, semiconductor device production method, and semiconductor device |
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| CN202211513979.3A Pending CN115718406A (en) | 2016-11-11 | 2017-11-09 | Photosensitive resin composition for forming resist, resin film, cured film, and semiconductor device |
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| KR (1) | KR102004129B1 (en) |
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| CN114957575A (en) * | 2022-04-22 | 2022-08-30 | 上海极紫科技有限公司 | Modified phenolic resin, preparation method thereof and positive photoresist |
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| JP7340329B2 (en) | 2018-12-17 | 2023-09-07 | 旭化成株式会社 | Method for manufacturing photosensitive resin laminate and resist pattern |
| WO2021241581A1 (en) * | 2020-05-29 | 2021-12-02 | 住友ベークライト株式会社 | Photosensitive resin composition |
| WO2023095785A1 (en) * | 2021-11-26 | 2023-06-01 | 東レ株式会社 | Photosensitive resin composition, cured article, organic el display device, semiconductor device, and method for producing cured article |
| WO2023182136A1 (en) * | 2022-03-24 | 2023-09-28 | 住友ベークライト株式会社 | Positive-type photosensitive resin composition, cured film, and semiconductor device |
| WO2024081174A1 (en) * | 2022-10-10 | 2024-04-18 | Lam Research Corporation | Oxymethylene copolymers for transient surface protection during chemical vapor deposition |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101846882A (en) * | 2009-03-23 | 2010-09-29 | 太阳油墨制造株式会社 | Light solidifying/heat solidifying resin composition, dry film, solidfied material, printed circuit board (PCB) |
| CN103901719A (en) * | 2014-04-28 | 2014-07-02 | 无锡德贝尔光电材料有限公司 | Quick-drying-type carboxyl-containing photosensitive resin and preparation method thereof |
| WO2015137486A1 (en) * | 2014-03-13 | 2015-09-17 | 三菱瓦斯化学株式会社 | Compound, resin, base layer film-forming material for lithography, base layer film for lithography, pattern-forming method, and method for refining compound or resin |
| JP2016074874A (en) * | 2014-10-02 | 2016-05-12 | 信越化学工業株式会社 | Silicone skeleton-containing polymer compound and production method of the same, chemically amplified negative resist material, photocurable dry film and production method of the dry film, pattern forming method, laminate, and substrate |
| WO2016143635A1 (en) * | 2015-03-06 | 2016-09-15 | 三菱瓦斯化学株式会社 | Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and method for purifying compound or resin |
| WO2016158458A1 (en) * | 2015-03-30 | 2016-10-06 | 三菱瓦斯化学株式会社 | Resist base material, resist composition, and method for forming resist pattern |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3575095B2 (en) * | 1994-12-28 | 2004-10-06 | Ｊｓｒ株式会社 | Radiation-sensitive resin composition and protective film for optical device formed therefrom |
| US6768197B2 (en) * | 1999-12-27 | 2004-07-27 | Sumitomo Bakelite Company, Ltd | Hardening flux, soldering resist, semiconductor package reinforced by hardening flux, semiconductor device and method of producing semiconductor package and semiconductor device |
| CA2599153A1 (en) * | 2005-02-25 | 2006-08-31 | Nippon Kayaku Kabushiki Kaisha | Epoxy resin, hardenable resin composition containing the same and use thereof |
| JP4858714B2 (en) * | 2006-10-04 | 2012-01-18 | 信越化学工業株式会社 | Polymer compound, resist material, and pattern forming method |
| JP6026097B2 (en) | 2010-11-17 | 2016-11-16 | 旭化成株式会社 | Photosensitive resin composition for semiconductor element surface protective film or interlayer insulating film |
| JP5698184B2 (en) * | 2011-09-02 | 2015-04-08 | 信越化学工業株式会社 | Positive resist material and pattern forming method |
| SG11201401963QA (en) * | 2011-12-13 | 2014-09-26 | Hitachi Chemical Co Ltd | Photosensitive resin composition, method for manufacturing patterned cured film, and electronic component |
| KR20150015443A (en) * | 2012-04-24 | 2015-02-10 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | Epoxy resin composition, resin sheet, cured article, and phenoxy resin |
| CN104937493B (en) * | 2013-01-24 | 2019-11-08 | 日产化学工业株式会社 | Photoetching resistant upper layer film formation composition and manufacturing method for semiconductor device |
| JP6159548B2 (en) | 2013-03-27 | 2017-07-05 | 新日鉄住金化学株式会社 | Epoxy resin composition, resin sheet and cured epoxy resin |
| JP5981465B2 (en) * | 2014-01-10 | 2016-08-31 | 信越化学工業株式会社 | Negative resist material and pattern forming method using the same |
| JP6605828B2 (en) | 2015-03-30 | 2019-11-13 | 日鉄ケミカル＆マテリアル株式会社 | Polyvalent hydroxy resin, epoxy resin, production method thereof, epoxy resin composition and cured product thereof |
| JP6482650B2 (en) * | 2015-03-31 | 2019-03-13 | 富士フイルム株式会社 | Pattern forming method, photomask manufacturing method, and electronic device manufacturing method |
| CN108139674B (en) * | 2015-10-19 | 2021-09-28 | 日产化学工业株式会社 | Composition for forming resist underlayer film containing long-chain alkyl group-containing novolak |
-
2017
- 2017-11-09 WO PCT/JP2017/040412 patent/WO2018088469A1/en active Application Filing
- 2017-11-09 CN CN201780059665.1A patent/CN109791356A/en active Pending
- 2017-11-09 KR KR1020197008002A patent/KR102004129B1/en active IP Right Grant
- 2017-11-09 CN CN202211513979.3A patent/CN115718406A/en active Pending
- 2017-11-09 JP JP2018527247A patent/JP6489289B2/en active Active
- 2017-11-10 TW TW106139009A patent/TWI765933B/en active
-
2018
- 2018-12-25 JP JP2018241861A patent/JP2019070832A/en not_active Withdrawn
-
2020
- 2020-07-17 JP JP2020122881A patent/JP7111129B2/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101846882A (en) * | 2009-03-23 | 2010-09-29 | 太阳油墨制造株式会社 | Light solidifying/heat solidifying resin composition, dry film, solidfied material, printed circuit board (PCB) |
| WO2015137486A1 (en) * | 2014-03-13 | 2015-09-17 | 三菱瓦斯化学株式会社 | Compound, resin, base layer film-forming material for lithography, base layer film for lithography, pattern-forming method, and method for refining compound or resin |
| CN103901719A (en) * | 2014-04-28 | 2014-07-02 | 无锡德贝尔光电材料有限公司 | Quick-drying-type carboxyl-containing photosensitive resin and preparation method thereof |
| JP2016074874A (en) * | 2014-10-02 | 2016-05-12 | 信越化学工業株式会社 | Silicone skeleton-containing polymer compound and production method of the same, chemically amplified negative resist material, photocurable dry film and production method of the dry film, pattern forming method, laminate, and substrate |
| WO2016143635A1 (en) * | 2015-03-06 | 2016-09-15 | 三菱瓦斯化学株式会社 | Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and method for purifying compound or resin |
| WO2016158458A1 (en) * | 2015-03-30 | 2016-10-06 | 三菱瓦斯化学株式会社 | Resist base material, resist composition, and method for forming resist pattern |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114957575A (en) * | 2022-04-22 | 2022-08-30 | 上海极紫科技有限公司 | Modified phenolic resin, preparation method thereof and positive photoresist |
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| CN115718406A (en) | 2023-02-28 |
| JP6489289B2 (en) | 2019-03-27 |
| JP7111129B2 (en) | 2022-08-02 |
| JP2019070832A (en) | 2019-05-09 |
| TW201830138A (en) | 2018-08-16 |
| TWI765933B (en) | 2022-06-01 |
| KR20190034680A (en) | 2019-04-02 |
| WO2018088469A1 (en) | 2018-05-17 |
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| JPWO2018088469A1 (en) | 2018-11-15 |
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