CN114031736A - Modified phenolic resin for photoresist, preparation method thereof and photoresist composition - Google Patents
Modified phenolic resin for photoresist, preparation method thereof and photoresist composition Download PDFInfo
- Publication number
- CN114031736A CN114031736A CN202111556168.7A CN202111556168A CN114031736A CN 114031736 A CN114031736 A CN 114031736A CN 202111556168 A CN202111556168 A CN 202111556168A CN 114031736 A CN114031736 A CN 114031736A
- Authority
- CN
- China
- Prior art keywords
- phenolic resin
- photoresist
- compound
- formula
- molar ratio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- 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
- C08G8/28—Chemically modified polycondensates
- C08G8/32—Chemically modified polycondensates by organic acids or derivatives thereof, e.g. fatty oils
-
- 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
Abstract
The invention belongs to the technical field of photoresist microelectronic chemistry, and discloses a modified phenolic resin for photoresist, a preparation method thereof and a photoresist composition, wherein the modified phenolic resin comprises a polymer structure shown in a formula I, wherein n and m are molar ratio, n is more than or equal to 0.09 and less than or equal to 0.91, m is more than or equal to 0.09 and less than or equal to 0.91, and n + m is 1; the R is1And R2Are each independently H, CH3、CH2CH3、CH2CH2CH3One or more of (a). The invention improves the solubility of the phenolic resin, and simultaneously, the compound shown in the formula III is introduced into the side chain structure of the phenolic resin, so that the heat resistance of the phenolic resin is further improved. The photoresist composition prepared from the modified phenolic resin has excellent sensitivity and resolution.
Description
Technical Field
The invention relates to the technical field of photoresist microelectronic chemistry, in particular to a modified phenolic resin for photoresist, a preparation method thereof and a photoresist composition.
Background
Photoresist is a core material for manufacturing integrated circuits, and is also a key factor affecting the performance, yield and reliability of integrated circuits. Photoresists can be classified into positive photoresists and negative photoresists according to their chemical reaction mechanism and development principle. The exposed regions of a positive photoresist can undergo photolytic reactions that degrade the photoresist into species that can be dissolved in a developer. The exposed areas of the negative photoresist may undergo a crosslinking reaction and may not be soluble in a developer, while the non-exposed areas may be soluble in a developer.
The G/I line photoresist takes linear phenolic resin as main resin and diazonaphthoquinone as photosensitizer, and the pattern of the mask is transferred and copied to the wafer through photoetching process procedures such as exposure, development and the like. The linear phenolic resin has strong dry and wet corrosion resistance, but the glass transition temperature of the linear phenolic resin is lower, the heat resistance is insufficient, and the heat resistance temperature of the photoresist required in most of the microelectronic processing technology at present is 200 ℃ or even higher. However, the heat resistance of the general linear phenolic resin is insufficient, the migration of the catalyst is increased in the photoetching process, the circuit device with higher resolution cannot be met, and the photoetching pattern deformation can occur in the conventional phenolic resin at the temperature higher than 140 ℃ to influence the resolution of the photoresist. In the fabrication of integrated circuits, the resolution of the photoresist directly affects the precision performance of the lithographic device. How to improve the photoresist photoetching efficiency and the resolution ratio under the condition of ensuring the pattern quality is the key point of the current photoresist product formula development.
Disclosure of Invention
In order to solve the technical problems, the invention provides a modified phenolic resin for a photoresist, a preparation method thereof and a photoresist composition.
The technical scheme of the invention is as follows:
a modified phenolic resin for photoresist, comprising a polymer structure represented by formula I:
wherein n and m are molar ratio, n is more than or equal to 0.09 and less than or equal to 0.91, m is more than or equal to 0.09 and less than or equal to 0.91, and n + m is 1;
the R is1And R2Are each independently H, CH3、CH2CH3、CH2CH2CH3One or more of (a).
Preferably, 0.1. ltoreq. n.ltoreq.0.8, more preferably 0.2. ltoreq. n.ltoreq.0.5.
A preparation method of modified phenolic resin for photoresist comprises the following steps:
(1) under the conditions of protective atmosphere and no water, adding the phenolic resin shown in the formula II, the compound shown in the formula III and a catalyst into an organic solvent, uniformly stirring, and reacting;
(2) after the reaction is finished, precipitating in water or normal hexane or a water-ethanol mixed solvent, filtering, drying a filter cake, dissolving the filter cake in an organic solvent, precipitating again in water or normal hexane or a water-ethanol mixed solvent, filtering, and drying the filter cake to obtain the modified phenolic resin for the photoresist;
the structures of the phenolic resin of the formula II and the compound of the formula III are as follows:
the R is1And R2Are each independently H, CH3、CH2CH3、CH2CH2CH3One or more of (a).
Preferably, the catalyst in step (1) is one or more of 4-Dimethylaminopyridine (DMAP), 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDC), Dicyclohexylcarbodiimide (DCC), N' -Carbonyldiimidazole (CDI).
Preferably, the molar ratio of the compound of formula III to the phenolic resin in step (1) is 0.2 to 0.4; the reaction temperature is 20-40 ℃, and the reaction time is 10-24 hours.
Preferably, the phenolic resin formula II is a polymer obtained by condensation polymerization of a cresol compound and an aldehyde compound, wherein the cresol compound includes one or more of m-cresol, p-cresol, ortho-cresol, xylenol and trimethylphenol; the aldehyde compound comprises one or more of formaldehyde, acetaldehyde and propionaldehyde; the molecular weight of the phenolic resin is 1000-20000g/mol, the preferred molecular weight is 2000-10000g/mol, and the more preferred molecular weight is 3000-8000 g/mol.
Preferably, the organic solvent used in steps (1) and (2) is one or more of N, N-Dimethylformamide (DMF), N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, dioxane, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, methyl isobutyl ketone, cyclopentanone, cyclohexanone, methyl ethyl ketone, diheptanone, ethyl lactate, butyl acetate, and neopentyl acetate.
A photoresist composition comprises, by mass, 10-50 parts of the modified phenolic resin, 0.5-10 parts of a photosensitizer, 0.1-10 parts of an auxiliary agent and 60-90 parts of an organic solvent.
The photosensitizer is prepared by reacting diazonaphthoquinone with a compound with a plurality of phenolic hydroxyl groups; wherein the molar ratio of the polyphenol hydroxyl compound to the diazonaphthoquinone is 1: 1-1: 4, preferably 1: 2-1: 3.
the diazonaphthoquinone comprises 2-diazo-1-naphthoquinone-4-sulfonyl chloride and 2-diazo-1-naphthoquinone-5-sulfonyl chloride; the polyphenol hydroxyl compound comprises one or more of 2, 3, 4-trihydroxydiphenylmethane, 2, 3, 4, 4' -tetrahydroxydiphenylmethane, 2, 3, 4-trihydroxybenzophenone, 2', 4, 4' -tetrahydroxybenzophenone, 2, 3, 4, 4' -tetrahydroxybenzophenone, 2', 3, 4-tetrahydroxybenzophenone and 2, 3', 4, 4' -tetrahydroxybenzophenone. Preferred are 2, 3, 4-trihydroxybenzophenone and 2, 3, 4, 4' -tetrahydroxybenzophenone.
Preferably, the photosensitizer comprises one or more of the following compounds G1, G2, G3 and G4, wherein the compound G1 is prepared from 2, 3, 4, 4' -tetrahydroxybenzophenone and 2-diazo-1 naphthoquinone-4-sulfonyl chloride in a molar ratio of 1: 2, and the compound G2 is prepared by reacting 2, 3, 4, 4' -tetrahydroxybenzophenone and 2-diazo-1-naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1: 4, and the compound G3 is prepared by mixing 2, 3, 4-trihydroxybenzophenone and 2-diazo-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1: 2, and the compound G4 is prepared by mixing 2, 3, 4-trihydroxybenzophenone and 2-diazo-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1: 3, reacting.
The auxiliary agent comprises one or more of epoxy compounds, ester compounds, ether compounds, polyhydroxy compounds, anthracene compounds and polymers thereof.
Preferably, the auxiliary agent is one or more of butyl lactate, 4, 4- (1-isopropylidene) bis (2, 6-bismethylphenol), 2', 4, 4' -tetrahydroxybenzophenone, 2, 3, 4, 4 '-tetrahydroxybenzophenone, 2', 4 '-dihydroxypropiophenone, 2, 4' -dihydroxydiphenylmethane, dibutyl phthalate, 9-anthracenol, 1, 8-bis (hydroxymethyl) anthracene, 9- (2-hydroxyethyl) anthracene, 9, 10-bis (chloromethyl) anthracene, 2-anthracenecarboxylic acid, 9, 10-diphenylanthracene, 9-phenylanthracene, 9- (1-naphthyl) anthracene.
Preferably, the organic solvent comprises one or more of anisole, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, methyl isobutyl ketone, cyclopentanone, cyclohexanone, methyl ethyl ketone, diheptanone, ethyl lactate, ethyl acetate, butyl acetate, neopentyl acetate, xylene, and toluene. Preferred is one or more of propylene glycol methyl ether acetate, propylene glycol methyl ether and ethyl lactate.
In addition, the components of the photoresist composition may further include a leveling agent, etc., and the kind and amount of the leveling agent are not particularly limited in the present invention, and the leveling agent can reduce the surface tension of the photoresist composition, promote the uniform distribution of the photoresist layer prepared from the photoresist composition, and prevent the occurrence of spots or scars, etc.
The method of formulating the photoresist composition is not particularly limited and may include the steps of: adding the phenolic resin, the photosensitizer, the plasticizer, the additive and the organic solvent into a light-proof glass ware according to the formula proportion in sequence, and shaking for 12-96 hours in a light-proof manner to fully dissolve the phenolic resin, the photosensitizer, the plasticizer, the additive and the organic solvent; then filtering the photoresist solution by using a filter with the diameter of 0.5 micron or less; the filtrate was collected in a light-shielding glass to obtain a photoresist composition.
The resolution test method is not particularly limited: gluing the 2-inch wafer by using a glue spreader, adjusting the rotating speed of spin coating according to the thickness of the photoresist layer, and baking and hardening after the spin coating is finished to form the photoresist layer with a certain thickness; under 365nm radiation, the mask is provided with a line width of 3-0.1 μm, and the ratio of the line width to the grating spacing is 1: 1-1: 5, carrying out exposure; then, development was carried out with 2.38 wt% aqueous tetramethylammonium hydroxide solution; the minimum line width that can be clearly observed after development.
The baking and hardening temperature is 50-150 ℃, the baking and hardening time is 0.5-5min, the preferable temperature is 90-100 ℃, and the baking and hardening time is 30-60 s.
The development time is 10-180s, preferably 30-60 s.
The photoresist composition described in the present application can be applied to a G-line photoresist or an I-line photoresist.
The phenolic resin is the most core material in the G/I line photoresist, and the modified phenolic resin is designed and synthesized by the invention. Compared with the prior art, the invention has the following advantages:
(1) the invention improves the solubility of the phenolic resin, and simultaneously, the compound shown in the formula III is introduced into the side chain structure of the phenolic resin, so that the heat resistance of the phenolic resin is further improved.
(2) The photoresist composition prepared from the modified phenolic resin has excellent sensitivity and resolution.
Drawings
FIG. 1 is a cross-sectional view of example 2 after exposure with a resolution of 0.35 μm.
FIG. 2 is a cross-sectional view of example 3 after exposure with a resolution of 0.45 μm.
FIG. 3 is a DSC two-shot temperature rise test curve of example 7, with a temperature rise rate of 10 deg.C/min.
FIG. 4 is a DSC two-shot temperature rise test curve of example 8, with a temperature rise rate of 10 deg.C/min.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the embodiments of the present invention are not limited thereto, and may be carried out with reference to conventional techniques for process parameters not particularly noted.
Example 1
Under a nitrogen-filled condition, 10g of a phenol resin (formula II, R)1Is H, R2Is CH3) 0.5 equivalent (equivalent ratio of phenolic resin hydroxyl group to hydroxyl group of phenolic resin) of cholic acid (formula III), 0.1 equivalent of DBU and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried, which was repeated twice to obtain a modified phenol resin (formula I, n ═ 0.42, and m ═ 0.58). The DSC test result shows that the glass transition temperature (T) of the phenolic resing) From 98 ℃ to 124 ℃.
Example 2
Under a nitrogen-filled condition, 10g of a phenol resin (formula II, R)1Is H, R2Is CH3) 0.3 equivalent of cholic acid (formula III), 0.3 equivalent of DCC, 0.1 equivalent of DMAP and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried, which was repeated twice to obtain a modified phenol resin (formula I, n ═ 0.25, m ═ 0.75). The DSC test result shows that the phenolic resin TgFrom 98 ℃ to 118 ℃.
Example 3
Under a nitrogen-filled condition, 10g of a phenol resin (formula II, R)1Is H, R2Is CH3) 0.8 equivalent of cholic acid (formula III), 0.8 equivalent of CDI and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried, which was repeated twice to obtain a modified phenol resin (formula I, n ═ 0.69, and m ═ 0.31). The DSC test result shows that the phenolic resin TgFrom 98 ℃ to 125 ℃.
Example 4
Under a nitrogen-filled condition, 10g of a phenol resin (formula II, R)1Is H, R2Is CH3) 0.1 equivalent of cholic acid (formula III), 0.2 equivalent of CDI and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried, which was repeated twice to obtain a modified phenol resin (formula I, n ═ 0.09, m ═ 0.91). The DSC test result shows that the phenolic resin TgFrom 98 ℃ to 106 ℃.
Example 5
Under a nitrogen-filled condition, 10g of a phenol resin (formula II, R)1Is H, R2Is CH3) 0.4 equivalent cholic acid (formula III), 0.4 equivalent EDC, 0.1 equivalent DMAP and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried, which was repeated twice to obtain a modified phenol resin (formula I, n ═ 0.35, m ═ 0.65). The DSC test result shows that the phenolic resin TgFrom 98 ℃ to 120 ℃.
Example 6
Under a nitrogen-filled condition, 10g of a phenol resin (formula II, R)1Is H, R2Is CH3) 1.0 equivalent of cholic acid (formula III), 1.0 equivalent of CDI and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried, which was repeated twice to obtain a modified phenol resin (formula I, n ═ 0.89, m ═ 0.11). The DSC test result shows that the phenolic resin TgFrom 98 ℃ to 125 ℃.
Example 7
Under a nitrogen-filled condition, 10g of a phenol resin (formula II, R)1Is H, R2Is CH3) 0.55 equivalent cholic acid (formula III), 5.5 equivalent CDI and 20mL of anhydrous DMF solventThe mixture was stirred at room temperature for 12 hours in a reaction flask, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried, which was repeated twice to obtain a modified phenol resin (formula I, n ═ 0.49, m ═ 0.51). The DSC test result shows that the phenolic resin TgFrom 98 ℃ to 124 ℃.
Example 8
Under a nitrogen-filled condition, 10g of a phenol resin (formula II, R)1Is H, R2Is CH3) 0.9 equivalent of cholic acid (formula III), 5.5 equivalents of CDI and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a mixed solvent of water/ethanol (6/4, v/v), filtered, and the filter cake was dried, which was repeated twice to obtain a modified phenol resin (formula I, n ═ 0.78, m ═ 0.22). The DSC test result shows that the phenolic resin TgFrom 98 ℃ to 125 ℃.
Example 9
The modified phenol resins and phenol resins of examples 1 to 8 were used as the main resins of the photoresists, and the specific components of the photoresists were 100 parts of (modified) phenol resin, 15 parts of photosensitizer G2, 0.5 part of leveling agent FC-4430, 0.5 part of crosslinking agent 2, 4' -dihydroxypropiophenone dissolved in 400 parts of Propylene Glycol Methyl Ether Acetate (PGMEA), and then filtered with 0.45 μm and 0.22 μm filters, respectively, to obtain the photoresist compositions. The resolution of the resulting photoresist was tested as follows: taking a wafer with the surface coated with silicon dioxide, spin-coating the photoresist obtained by the method on the surface, coating the photoresist with the thickness of 1.5 mu m, heating at 100 ℃ for 1min, baking and hardening to form a photoresist layer with a certain thickness; under 365nm radiation, the mask is provided with a line width of 3-0.1 μm, and the ratio of the line width to the grating spacing is 1: 1-1: 5, carrying out exposure; then, the resultant was developed for 60 seconds using 2.38% tetramethylammonium hydroxide aqueous solution as a developer, and the resultant was washed with deionized water to fix the image, and the micro-pattern was subjected to a resolution test using a scanning electron microscope, and the results are detailed in table 1.
TABLE 1
Remarking: phenolic resin of formula II R1Is H, R2Is CH3。
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A modified phenolic resin for photoresist, characterized in that it comprises a polymer structure represented by formula I:
wherein n and m are molar ratio, n is more than or equal to 0.09 and less than or equal to 0.91, m is more than or equal to 0.09 and less than or equal to 0.91, and n + m is 1;
the R is1And R2Are each independently H, CH3、CH2CH3、CH2CH2CH3One or more of (a).
2. The modified phenolic resin for photoresist according to claim 1, wherein n is 0.2. ltoreq. n.ltoreq.0.4.
3. A preparation method of modified phenolic resin for photoresist is characterized by comprising the following steps:
(1) under the conditions of protective atmosphere and no water, adding the phenolic resin shown in the formula II, the compound shown in the formula III and a catalyst into an organic solvent, uniformly stirring, and reacting;
(2) after the reaction is finished, precipitating in water or normal hexane or a water-ethanol mixed solvent, filtering, drying a filter cake, dissolving the filter cake in an organic solvent, precipitating again in water or normal hexane or a water-ethanol mixed solvent, filtering, and drying the filter cake to obtain the modified phenolic resin for the photoresist;
the structures of the phenolic resin of the formula II and the compound of the formula III are as follows:
the R is1And R2Are each independently H, CH3、CH2CH3、CH2CH2CH3One or more of (a).
4. The method according to claim 2, wherein the catalyst in the step (1) is one or more selected from the group consisting of 4-dimethylaminopyridine, 1, 8-diazabicyclo [5.4.0] undec-7-ene, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, dicyclohexylcarbodiimide, and N, N' -carbonyldiimidazole.
5. The method according to claim 3, wherein the molar ratio of the compound of formula III to the phenolic resin in step (1) is 0.2 to 0.4; the reaction temperature is 20-40 ℃, and the reaction time is 10-24 hours.
6. The preparation method according to claim 2, 3 or 4, wherein the phenolic resin formula II is a polymer obtained by condensation polymerization of a cresol compound and an aldehyde compound, wherein the cresol compound comprises one or more of m-cresol, p-cresol, ortho-cresol, xylenol and trimethylphenol; the aldehyde compound comprises one or more of formaldehyde, acetaldehyde and propionaldehyde; the molecular weight of the phenolic resin is 1000-20000g/mol, the preferred molecular weight is 2000-10000g/mol, and the more preferred molecular weight is 3000-8000 g/mol.
7. The method according to claim 2, 3 or 4, wherein the organic solvent used in steps (1) and (2) is one or more selected from the group consisting of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, dioxane, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, methyl isobutyl ketone, cyclopentanone, cyclohexanone, methyl ethyl ketone, diheptone, ethyl lactate, butyl acetate and neopentyl acetate.
8. A photoresist composition is characterized by comprising 10-50 parts of the modified phenolic resin of claim 1 or 2, 0.5-10 parts of a photosensitizer, 0.1-10 parts of an auxiliary agent and 60-90 parts of an organic solvent in parts by mass.
9. The photoresist composition of claim 8, wherein the sensitizer comprises one or more of the following compounds G1, G2, G3, and G4, wherein compound G1 is prepared from 2, 3, 4, 4' -tetrahydroxybenzophenone and 2-diazo-1-naphthoquinone-4-sulfonyl chloride in a molar ratio of 1: 2, and the compound G2 is prepared by reacting 2, 3, 4, 4' -tetrahydroxybenzophenone and 2-diazo-1-naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1: 4, and the compound G3 is prepared by mixing 2, 3, 4-trihydroxybenzophenone and 2-diazo-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1: 2, and the compound G4 is prepared by mixing 2, 3, 4-trihydroxybenzophenone and 2-diazo-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1: 3, reacting.
10. The photoresist composition according to claim 8 or 9, wherein the auxiliary is butyl lactate, 4, 4- (1-isopropylidene) bis (2, 6-bis-methylphenol), 2', 4, 4' -tetrahydroxybenzophenone, 2, 3, 4, 4 '-tetrahydroxybenzophenone, 2', one or more of 4 '-dihydroxypropiophenone, 2, 4' -dihydroxydiphenylmethane, dibutyl phthalate, 9-anthracenol, 1, 8-bis (hydroxymethyl) anthracene, 9- (2-hydroxyethyl) anthracene, 9, 10-bis (chloromethyl) anthracene, 2-anthracenecarboxylic acid, 9, 10-diphenylanthracene, 9-phenylanthracene, 9- (1-naphthyl) anthracene;
the organic solvent comprises one or more of anisole, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, methyl isobutyl ketone, cyclopentanone, cyclohexanone, methyl ethyl ketone, diheptanone, ethyl lactate, ethyl acetate, butyl acetate, neopentyl acetate, xylene and toluene. Preferred is one or more of propylene glycol methyl ether acetate, propylene glycol methyl ether and ethyl lactate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111556168.7A CN114031736B (en) | 2021-12-17 | 2021-12-17 | Modified phenolic resin for photoresist, preparation method thereof and photoresist composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111556168.7A CN114031736B (en) | 2021-12-17 | 2021-12-17 | Modified phenolic resin for photoresist, preparation method thereof and photoresist composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114031736A true CN114031736A (en) | 2022-02-11 |
| CN114031736B CN114031736B (en) | 2023-10-10 |
Family
ID=80147128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111556168.7A Active CN114031736B (en) | 2021-12-17 | 2021-12-17 | Modified phenolic resin for photoresist, preparation method thereof and photoresist composition |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114031736B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116731270A (en) * | 2023-06-14 | 2023-09-12 | 北京理工大学 | Functional phenolic resin, preparation method thereof and application thereof in perovskite quantum dot patterning |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6480944A (en) * | 1987-09-24 | 1989-03-27 | Hitachi Ltd | Photosensitive resin composition |
| US20030104310A1 (en) * | 2001-11-30 | 2003-06-05 | Dentinger Paul M. | Photosensitive dissolution inhibitors and resists based on onium salt carboxylates |
| US20070231734A1 (en) * | 2005-09-29 | 2007-10-04 | Allen Robert D | Low activation energy dissolution modification agents for photoresist applications |
| CN101230122A (en) * | 2008-02-27 | 2008-07-30 | 深圳市容大电子材料有限公司 | Anhydride modified alkyd resin and photoresist composition obtained thereby |
| US20080318156A1 (en) * | 2006-02-16 | 2008-12-25 | Shinji Tanaka | Adamantane Based Molecular Glass Photoresists for Sub-200 Nm Lithography |
| KR20090037172A (en) * | 2007-10-11 | 2009-04-15 | 주식회사 엘지화학 | Cholate-based compound and negative-type photoresist resin composition comprising the same |
| CN112094392A (en) * | 2019-06-17 | 2020-12-18 | 山东圣泉新材料股份有限公司 | Phenolic resin and preparation method and application thereof |
| CN112679653A (en) * | 2020-12-28 | 2021-04-20 | 甘肃华隆芯材料科技有限公司 | Photoresist film-forming resin and preparation method of photoresist composition thereof |
| CN113461885A (en) * | 2021-08-09 | 2021-10-01 | 北京彤程创展科技有限公司 | Phenolic resin for photoresist and preparation method thereof |
-
2021
- 2021-12-17 CN CN202111556168.7A patent/CN114031736B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6480944A (en) * | 1987-09-24 | 1989-03-27 | Hitachi Ltd | Photosensitive resin composition |
| US20030104310A1 (en) * | 2001-11-30 | 2003-06-05 | Dentinger Paul M. | Photosensitive dissolution inhibitors and resists based on onium salt carboxylates |
| US20070231734A1 (en) * | 2005-09-29 | 2007-10-04 | Allen Robert D | Low activation energy dissolution modification agents for photoresist applications |
| US20080318156A1 (en) * | 2006-02-16 | 2008-12-25 | Shinji Tanaka | Adamantane Based Molecular Glass Photoresists for Sub-200 Nm Lithography |
| KR20090037172A (en) * | 2007-10-11 | 2009-04-15 | 주식회사 엘지화학 | Cholate-based compound and negative-type photoresist resin composition comprising the same |
| CN101230122A (en) * | 2008-02-27 | 2008-07-30 | 深圳市容大电子材料有限公司 | Anhydride modified alkyd resin and photoresist composition obtained thereby |
| CN112094392A (en) * | 2019-06-17 | 2020-12-18 | 山东圣泉新材料股份有限公司 | Phenolic resin and preparation method and application thereof |
| CN112679653A (en) * | 2020-12-28 | 2021-04-20 | 甘肃华隆芯材料科技有限公司 | Photoresist film-forming resin and preparation method of photoresist composition thereof |
| CN113461885A (en) * | 2021-08-09 | 2021-10-01 | 北京彤程创展科技有限公司 | Phenolic resin for photoresist and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| LEONARD V. INTERRANTE 等, 上海交通大学出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116731270A (en) * | 2023-06-14 | 2023-09-12 | 北京理工大学 | Functional phenolic resin, preparation method thereof and application thereof in perovskite quantum dot patterning |
| CN116731270B (en) * | 2023-06-14 | 2023-12-01 | 北京理工大学 | Functional phenolic resin, preparation method thereof and application thereof in perovskite quantum dot patterning |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114031736B (en) | 2023-10-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN114031736B (en) | Modified phenolic resin for photoresist, preparation method thereof and photoresist composition | |
| JP2942484B2 (en) | High contrast, high thermal stability positive photoresist | |
| JP3660195B2 (en) | Photoresist composition and method for forming semiconductor pattern using the same | |
| KR100465664B1 (en) | Sensitive radiation-sensitive resin composition | |
| CN114137795A (en) | Photoresist composition and application thereof | |
| TW201910363A (en) | Polymer, resin composition, resin film, method for producing patterned resin film, and electronic component | |
| CN112684661B (en) | Photoresist composition and preparation method thereof | |
| JP4053402B2 (en) | Positive photoresist composition for LCD production and method for forming resist pattern | |
| JP3978885B2 (en) | Radiation sensitive resin composition | |
| JP3060440B2 (en) | Positive resist composition | |
| JPH0356960A (en) | Positive type photoresist composition | |
| JP2574692B2 (en) | Positive photoresist composition | |
| KR100862018B1 (en) | Positive resist composition and patterning process | |
| KR100846084B1 (en) | Positive photoresist composition | |
| JP3633119B2 (en) | Radiation sensitive resin composition | |
| JP2811663B2 (en) | Radiation-sensitive resin composition | |
| JPH0527430A (en) | Positive photoresist composition | |
| JPH0237348A (en) | Positive type photosensitive resin composition | |
| JP3671608B2 (en) | Radiation sensitive resin composition | |
| JP3265689B2 (en) | Photosensitive agent, method for producing the same, and positive resist composition using the same | |
| CN117148668A (en) | EUV/EB photoresist, preparation method and application thereof | |
| JPH0519466A (en) | Positive type photoresist composition | |
| JP3976101B2 (en) | Method for producing quinonediazidosulfonate, and positive photoresist composition containing quinonediazidosulfonate produced by the method | |
| JP3690015B2 (en) | Radiation sensitive resin composition | |
| CN117872678A (en) | Photosensitive resin composition, photosensitive element, and method for producing laminate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |