CN114031736B - 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 PDF

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CN114031736B
CN114031736B CN202111556168.7A CN202111556168A CN114031736B CN 114031736 B CN114031736 B CN 114031736B CN 202111556168 A CN202111556168 A CN 202111556168A CN 114031736 B CN114031736 B CN 114031736B
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phenolic resin
compound
photoresist
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modified phenolic
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CN114031736A (en
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季生象
刘亚栋
李小欧
农美凤
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Huangpu Institute of Materials
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/28Chemically modified polycondensates
    • C08G8/32Chemically modified polycondensates by organic acids or derivatives thereof, e.g. fatty oils
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials

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Abstract

The application belongs to the technical field of photoresist microelectronics 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, n and m are molar ratio, n is more than or equal to 0.09 and less than or equal to 0.91,0.09 and m is less than or equal to 0.91, and n+m=1; the R is 1 And R is 2 H, CH each independently of the other 3 、CH 2 CH 3 、CH 2 CH 2 CH 3 One or more of the following. The application improves the solubility of the phenolic resin, and simultaneously introduces the compound shown in the formula III into the side chain structure of the phenolic resin, thereby further improving the heat resistance of the phenolic resin. The photoresist composition prepared from the modified phenolic resin has excellent sensitivity and resolution.

Description

Modified phenolic resin for photoresist, preparation method thereof and photoresist composition
Technical Field
The application relates to the technical field of photoresist microelectronics chemistry, in particular to a modified phenolic resin for photoresist, a preparation method thereof and a photoresist composition.
Background
Photoresist is a core consumable material for integrated circuit fabrication and is also a critical factor affecting integrated circuit performance, yield and reliability. Photoresists can be classified into positive photoresists and negative photoresists according to the chemical reaction mechanism and development principle of the photoresist. The exposed areas of the positive photoresist undergo a photolytic reaction that degrades the photoresist into a substance that is soluble in the developer. The exposed areas of the negative photoresist undergo a crosslinking reaction and are insoluble in the developer, and the unexposed areas are soluble in the developer.
The G/I line photoresist uses linear phenolic resin as main resin and diazonaphthoquinone as sensitizer, and the pattern of mask is transferred and copied onto the wafer through exposure, development and other photoetching process. The linear phenolic resin has strong dry corrosion resistance and wet corrosion resistance, but the linear phenolic resin has lower glass transition temperature and insufficient heat resistance, and the heat resistance temperature of the photoresist required in most microelectronic processing technologies at the day before is 200 ℃ or higher. However, the heat resistance of the general phenolic novolac 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 conventional phenolic novolac resin can deform the photoetching pattern at a 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. Under the condition of ensuring the quality of the pattern, improving the photoetching efficiency and resolution of the photoresist is an important point of the development of the current photoresist product formula.
Disclosure of Invention
In order to solve the technical problems, the application provides a modified phenolic resin for photoresist, a preparation method thereof and a photoresist composition.
The technical scheme of the application is as follows:
a modified phenolic resin for photoresist comprising a polymer structure of formula I:
wherein n and m are molar ratios, n is more than or equal to 0.09 and less than or equal to 0.91,0.09 and m is more than or equal to 0.91, and n+m=1;
the R is 1 And R is 2 H, CH each independently of the other 3 、CH 2 CH 3 、CH 2 CH 2 CH 3 One or more of the following.
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 protective atmosphere and anhydrous condition, adding the phenolic resin of the formula II, the compound of the formula III and the catalyst into an organic solvent, and uniformly stirring to react;
(2) After the reaction is finished, precipitating in water or normal hexane or water ethanol mixed solvent, filtering, drying a filter cake, dissolving the filter cake in an organic solvent, and precipitating, filtering and drying the filter cake again in water or normal hexane or water ethanol mixed solvent to obtain the modified phenolic resin for photoresist;
the phenolic resin of the formula II and the compound of the formula III have the following structures:
the R is 1 And R is 2 H, CH each independently of the other 3 、CH 2 CH 3 、CH 2 CH 2 CH 3 One or more of the following.
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 phenolic resin in step (1) is from 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 formed by condensation polymerization of cresol compounds and aldehyde compounds, wherein the cresol compounds comprise one or more of m-cresol, p-cresol, o-cresol, xylenol and tricresyl; the aldehyde compound comprises one or more of formaldehyde, acetaldehyde and propionaldehyde; the molecular weight of the phenolic resin is 1000-20000g/mol, preferably 2000-10000g/mol, more preferably 3000-8000g/mol.
Preferably, the organic solvent used in steps (1) and (2) is one or more of N, N-Dimethylformamide (DMF), N-dimethylacetamide, dimethylsulfoxide, 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.
The 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 sensitizer is prepared by reacting diazonaphthoquinone with a compound with a plurality of phenolic hydroxyl groups; wherein, the mol ratio of the polyphenol hydroxyl compound to the diazonaphthoquinone is 1:1-1:4, preferably 1:2-1:3.
the diazonaphthoquinone comprises 2-diazonaphthoquinone-1-naphthoquinone-4-sulfonyl chloride and 2-diazonaphthoquinone-1-naphthoquinone-5-sulfonyl chloride; the polyphenol hydroxyl compound comprises 2,3, 4-trihydroxy diphenyl methane, 2,3, 4' -tetrahydroxy diphenyl methane, 2,3, 4-trihydroxy diphenyl ketone, 2',4,4' -tetrahydroxybenzophenone, 2,3, 4' -tetrahydroxybenzophenone, 2',3, 4-tetrahydroxybenzophenone, 2,3', 4' -tetrahydroxybenzophenone. Preferred are 2,3, 4-trihydroxybenzophenone and 2,3, 4' -tetrahydroxybenzophenone.
Preferably, the sensitizer comprises one or more of the following compounds G1, G2, G3 and G4, wherein the compound G1 is prepared from 2,3, 4' -tetrahydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride in a molar ratio of 1:2, and the compound G2 is prepared by 2,3, 4' -tetrahydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:4, and the compound G3 is prepared from 2,3, 4-trihydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:2, and the compound G4 is prepared by 2,3, 4-trihydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:3, reacting to obtain the product.
The auxiliary agent comprises one or more of epoxy compounds, esters compounds, ethers compounds, polyhydroxy compounds, anthracene compounds and polymers thereof.
Preferably, the auxiliary is one or more of butyl lactate, 4- (1-isopropylidene) bis (2, 6-bisphenol), 2',4' -tetrahydroxybenzophenone, 2,3,4 '-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-anthranilic acid, 9, 10-diphenyl anthracene, 9-phenyl anthracene, 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 are one or more of propylene glycol methyl ether acetate, propylene glycol monomethyl ether and ethyl lactate.
In addition, the components of the photoresist composition may further include a leveling agent, etc., and the type and amount of the leveling agent are not particularly limited in the present application, 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 spots or scars, etc.
The preparation method of the photoresist composition is not particularly limited, and may include the steps of: sequentially adding phenolic resin, a photosensitizer, a plasticizer, an additive and an organic solvent into a light-proof glassware according to the formula proportion, and vibrating for 12-96 hours in a light-proof manner to fully dissolve the materials; then filtering the photoresist solution with a filter of 0.5 μm or less; the filtrate was collected in a light-shielding glass to obtain a photoresist composition.
The resolution test method is not particularly limited: using a gumming machine to carry out gumming on a 2-inch wafer, 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; at 365nm radiation, the reticle is provided with a linewidth of 3-0.1 μm, the ratio of linewidth to grating pitch being 1:1-1:5, exposing; then, development was performed with 2.38wt% aqueous tetramethylammonium hydroxide; the minimum line width that can be clearly observed after development.
The baking hardening temperature is 50-150deg.C, the time is 0.5-5min, the preferable temperature is 90-100deg.C, and the time is 30-60s.
The development time is 10 to 180s, preferably 30 to 60s.
The photoresist composition of the present application can be applied to G-line photoresist or I-line photoresist.
The phenolic resin is the core material in the G/I line photoresist, and the application designs and synthesizes a modified phenolic resin. Compared with the prior art, the application has the following advantages:
(1) The application improves the solubility of the phenolic resin, and simultaneously introduces the compound shown in the formula III into the side chain structure of the phenolic resin, thereby further improving the heat resistance of the phenolic resin.
(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 microns.
FIG. 2 is a cross-sectional view of example 3 after exposure with a resolution of 0.45 microns.
FIG. 3 is a DSC secondary temperature rise test curve of example 7 at a temperature rise rate of 10deg.C/min.
FIG. 4 is a DSC secondary temperature rise test curve of example 8 at a temperature rise rate of 10deg.C/min.
Detailed Description
The present application will be described in further detail with reference to specific examples, but embodiments of the present application are not limited thereto, and may be performed with reference to conventional techniques for process parameters that are not specifically noted.
Example 1
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) Cholic acid (formula III), 0.5 times equivalent DBU and 20mL anhydrous DMF solvent (0.1 times equivalent of the ratio of the equivalents of hydroxyl groups of the phenolic resin to the equivalents of hydroxyl groups of the phenolic resin, all mentioned below) 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 dried to a filter cake. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.42, m=0.58). DSC test results showed that the glass transition temperature (T g ) Increasing from 98 ℃ to 124 ℃.
Example 2
10g of phenolic resin was charged with nitrogen(formula II, R) 1 Is H, R 2 Is CH 3 ) 0.3 times equivalent of cholic acid (formula III), 0.3 times equivalent of DCC, 0.1 times equivalent of DMAP and 20mL of anhydrous DMF solvent are added into 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 is dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.25, m=0.75). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 118 ℃.
Example 3
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 0.8 times equivalent of cholic acid (formula III), 0.8 times 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 water/ethanol (6/4, v/v) mixed solvent, filtered, and dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.69, m=0.31). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 125 ℃.
Example 4
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 0.1 times equivalent of cholic acid (formula III), 0.2 times 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 water/ethanol (6/4, v/v) mixed solvent, filtered, and dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.09, m=0.91). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 106 ℃.
Example 5
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 0.4 times the equivalent of cholic acid (formula III), 0.4 times the equivalentTo a reaction flask, 0.1-fold equivalent of DMAP and 20mL of anhydrous DMF solvent were added, 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 water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.35, m=0.65). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 120 ℃.
Example 6
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 1.0 times equivalent of cholic acid (formula III), 1.0 times 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 water/ethanol (6/4, v/v) mixed solvent, filtered, and dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.89, m=0.11). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 125 ℃.
Example 7
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 0.55 times equivalent of cholic acid (formula III), 5.5 times 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 water/ethanol (6/4, v/v) mixed solvent, filtered, and dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.49, m=0.51). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 124 ℃.
Example 8
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 0.9 times equivalent of cholic acid (formula III), 5.5 times equivalent of CDI and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, and mixed in water/ethanol (6/4, v/v)Precipitating in solvent, filtering, and drying filter cake. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.78, m=0.22). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 125 ℃.
Example 9
The modified phenolic resins and phenolic resins of examples 1 to 8 were used as main resins of photoresists, the specific components of the photoresists were 100 parts of (modified) phenolic resin, 15 parts of photosensitizer G2,0.5 part of leveling agent FC-4430,0.5 parts 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 photoresist compositions. The resolution of the resulting photoresist was tested as follows: taking a wafer with silicon dioxide coated on the surface, 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, and baking for hardening to form a photoresist layer with a certain thickness; at 365nm radiation, the reticle is provided with a linewidth of 3-0.1 μm, the ratio of linewidth to grating pitch being 1:1-1:5, exposing; then, the corresponding patterns were obtained by developing with 2.38% aqueous tetramethylammonium hydroxide as a developer for 60 seconds, washing and fixing with deionized water, and resolution testing was performed on the micropatterns using a scanning electron microscope, and the results are shown in Table 1 in detail.
TABLE 1
Remarks: phenolic resin of formula II, R 1 Is H, R 2 Is CH 3
The above examples are preferred embodiments of the present application, but the embodiments of the present application are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present application should be made in the equivalent manner, and the embodiments are included in the protection scope of the present application.

Claims (12)

1. The application of the modified phenolic resin in preparing photoresist is characterized in that the modified phenolic resin comprises a polymer structure shown in a formula I:
wherein n and m are molar ratios, n is more than or equal to 0.09 and less than or equal to 0.69,0.31 and m is more than or equal to 0.91, and n+m=1;
the R is 1 And R is 2 H, CH each independently of the other 3 、CH 2 CH 3 、CH 2 CH 2 CH 3 One or more of the following.
2. The use according to claim 1, wherein 0.2.ltoreq.n.ltoreq.0.4.
3. The use according to claim 1 or 2, characterized in that the preparation method of the modified phenolic resin comprises the following steps:
(1) Under the protective atmosphere and anhydrous condition, adding the phenolic resin of the formula II, the compound of the formula III and the catalyst into the organic solvent A, and uniformly stirring to react;
(2) After the reaction is finished, precipitating in water or normal hexane or water ethanol mixed solvent, filtering, drying a filter cake, dissolving the filter cake in an organic solvent A, and precipitating, filtering and drying the filter cake again in water or normal hexane or water ethanol mixed solvent to obtain the modified phenolic resin for photoresist;
the phenolic resin of the formula II and the compound of the formula III have the following structures:
the R is 1 And R is 2 H, CH each independently of the other 3 、CH 2 CH 3 、CH 2 CH 2 CH 3 One or more of the following.
4. The use according to claim 3, wherein the catalyst in step (1) is one or more of 4-dimethylaminopyridine, 1, 8-diazabicyclo [5.4.0] undec-7-ene, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, dicyclohexylcarbodiimide, N' -carbonyldiimidazole.
5. The use according to claim 4, wherein the molar ratio of the compound of formula III to phenolic resin in step (1) is from 0.2 to 0.4; the reaction temperature is 20-40 ℃ and the reaction time is 10-24 hours.
6. The use according to claim 5, wherein the phenolic resin of formula II is a polymer obtained by condensation polymerization of a cresol compound and an aldehyde compound, the cresol compound comprising one or more of m-cresol, p-cresol, o-cresol, xylenol and tricresyl; the aldehyde compound comprises one or more of formaldehyde, acetaldehyde and propionaldehyde; the molecular weight of the phenolic resin is 1000-20000g/mol.
7. The use according to claim 6, wherein the phenolic resin has a molecular weight of 2000-10000g/mol.
8. The use according to claim 7, wherein the phenolic resin has a molecular weight of 3000-8000g/mol.
9. The method according to claim 6, wherein the organic solvent A used in the steps (1) and (2) is one or more of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, 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.
10. A photoresist composition, which is characterized by comprising 10-50 parts of the modified phenolic resin according to any one of claims 1-9, 0.5-10 parts of a photosensitizer, 0.1-10 parts of an auxiliary agent and 60-90 parts of an organic solvent B in mass fraction.
11. The photoresist composition according to claim 10, wherein the sensitizer comprises one or more of the following compounds G1, G2, G3 and G4, wherein the compound G1 is composed of 2,3, 4' -tetrahydroxybenzophenone and 2-diazonaphthoquinone-1-4-sulfonyl chloride in a molar ratio of 1:2, and the compound G2 is prepared by 2,3, 4' -tetrahydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:4, and the compound G3 is prepared from 2,3, 4-trihydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:2, and the compound G4 is prepared by 2,3, 4-trihydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:3, reacting to obtain the product.
12. The photoresist composition according to claim 10 or 11, wherein the adjuvant is one or more of butyl lactate, 4- (1-isopropylidene) bis (2, 6-bisphenol), 2',4' -tetrahydroxybenzophenone, 2,3,4 '-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-anthranilic acid, 9, 10-diphenylanthracene, 9-phenylanthracene, 9- (1-naphthyl) anthracene;
the organic solvent B 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.
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6480944A (en) * 1987-09-24 1989-03-27 Hitachi Ltd Photosensitive resin composition
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
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

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6969576B2 (en) * 2001-11-30 2005-11-29 Sandia National Laboratories Photosensitive dissolution inhibitors and resists based on onium salt carboxylates
US7358029B2 (en) * 2005-09-29 2008-04-15 International Business Machines Corporation Low activation energy dissolution modification agents for photoresist applications
JP2009527019A (en) * 2006-02-16 2009-07-23 コーネル・リサーチ・ファンデーション・インコーポレイテッド Adamantane-based molecular glass photoresist for lithography below 200 nm

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6480944A (en) * 1987-09-24 1989-03-27 Hitachi Ltd Photosensitive resin composition
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)

* Cited by examiner, † Cited by third party
Title
Leonard V. Interrante 等.《先进材料化学》.上海交通大学出版社,2013,(第1版),第93页. *

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