CN112650025B - Positive photoresist composition and preparation method thereof - Google Patents
Positive photoresist composition and preparation method thereof Download PDFInfo
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- CN112650025B CN112650025B CN202011537008.3A CN202011537008A CN112650025B CN 112650025 B CN112650025 B CN 112650025B CN 202011537008 A CN202011537008 A CN 202011537008A CN 112650025 B CN112650025 B CN 112650025B
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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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Abstract
The invention provides a positive photoresist composition and a preparation method thereof, wherein the positive photoresist composition comprises the following raw material components in parts by mass: 10-30 parts of titanium dioxide modified phenolic resin, 1-5 parts of photosensitizer, 0.1-0.3 part of organosilicon leveling agent and 40-70 parts of organic solvent; wherein the titanium dioxide modified phenolic resin is phenolic resin with molecular chains grafted with nano titanium dioxide. The positive photoresist composition of the photoresist composition has the advantages of high photosensitive speed, high resolution, small line edge roughness and the like when being used for photoirradiation imaging.
Description
Technical Field
The invention relates to the technical field of photoetching, in particular to a positive photoresist composition and a preparation method thereof.
Background
Photoresist is a kind of corrosion-resistant film material with solubility changed after energy radiation such as light beam, electron beam, ion beam, etc., and has wide application in micro-processing of integrated circuits and semiconductor discrete devices. The photoresist is a key material in micro-machining technology because the photoresist is coated on semiconductor, conductor and insulator materials, the part left after exposure and development protects the bottom layer, and then etching is carried out by adopting an etchant to transfer the required micro-pattern from the mask plate to the substrate to be machined. Photoresists are classified into positive photoresists and negative photoresists according to the photochemical reaction mechanism: after exposure, the solubility of the photoresist in a developing solution is increased, and the photoresist with the same pattern as that of the mask is obtained; after exposure, the photoresist is reduced in solubility or even insoluble in a developing solution, resulting in what is called a negative photoresist having a pattern opposite to that of the reticle. Both photoresists have different fields of application, and positive photoresists are more common, accounting for more than 80% of the total photoresist.
With the improvement of integrated circuit integration and the reduction of processing line width, the development process from G line (436 nm) lithography, I line (365 nm) lithography to deep ultraviolet 248nm lithography and 193nm lithography is also applied to the photoresist corresponding to each exposure wavelength. With the variation of exposure wavelength, the composition and structure of the photoresist are also continuously changed, so that the comprehensive performance of the photoresist meets the requirements of the integrated process. However, currently, a phenol resin-diazonaphthoquinone positive type photoresist is used in the I-line lithography, and both photosensitivity and resolution thereof are to be improved.
Disclosure of Invention
Based on the technical problems in the background art, the invention provides a positive photoresist composition and a preparation method thereof, and the positive photoresist composition has the advantages of high photosensitive speed, high resolution, small line edge roughness and the like in the process of light irradiation imaging.
The positive photoresist composition provided by the invention comprises the following raw material components in parts by weight: 10-30 parts of titanium dioxide modified phenolic resin, 1-5 parts of photosensitizer, 0.1-0.3 part of organosilicon leveling agent and 40-70 parts of organic solvent;
wherein the titanium dioxide modified phenolic resin is phenolic resin with molecular chains grafted with nano titanium dioxide.
Preferably, the phenolic resin with the molecular chain grafted with the nano titanium dioxide is formed by condensation reaction of the phenolic resin and the nano titanium dioxide modified by the epoxy group-containing silane coupling agent.
Preferably, the phenolic resin is a resin obtained by condensing cresol and formaldehyde, and the molecular weight of the phenolic resin is 2000-20000.
Preferably, the nano titanium dioxide modified by the epoxy group-containing silane coupling agent is obtained by heating the epoxy group-containing silane coupling agent and the nano titanium dioxide in an alcohol solvent;
preferably, the epoxy group-containing silane coupling agent is at least one of 3-glycidoxypropyl trimethoxysilane, 3-glycidoxypropyl methyl diethoxysilane or 3-glycidoxypropyl triethoxysilane.
The phenolic resin with the molecular chain grafted with the nano titanium dioxide is prepared by carrying out ring-opening addition reaction on phenolic hydroxyl on the phenolic resin and epoxy on the nano titanium dioxide modified by the epoxy-containing silane coupling agent, so that the nano titanium dioxide modified by the epoxy-containing silane coupling agent is grafted on the phenolic resin, and the molecular chain of the phenolic resin is grafted with the nano titanium dioxide.
Preferably, the weight ratio of the phenolic resin to the nano titanium dioxide modified by the epoxy group-containing silane coupling agent is 7-12:1.
Preferably, the photosensitizer is an ester of 2,3, 4' -tetrahydroxybenzophenone and 2,1, 5-diazonaphthoquinone sulfonyl chloride or an ester of 2,2', 4' -tetrahydroxybenzophenone and 2,1, 5-diazonaphthoquinone sulfonyl chloride;
preferably, the degree of esterification of the esters is 50-80%.
Preferably, the organosilicon leveling agent is at least one of polydimethylsiloxane or silicone oil.
Preferably, the organic solvent is at least one of ethyl lactate, ethyl acetate, n-butyl acetate, ethylene glycol monomethyl ether, diethylene glycol dimethyl ether, propylene glycol methyl ether acetate, propylene glycol monomethyl ether or diethylene glycol monomethyl ether.
Preferably, the positive photoresist composition further comprises at least one of a colorant, a plasticizer, or a surfactant.
The preparation method of the positive photoresist composition comprises the following steps: and uniformly mixing the titanium dioxide modified phenolic resin, the photosensitizer, the organosilicon leveling agent and the organic solvent.
According to the positive photoresist composition provided by the invention, the titanium dioxide modified phenolic resin is introduced into the formula, so that the nano titanium dioxide can be effectively grafted on the phenolic film-forming resin when the photoresist composition forms a film, thereby not only improving the heat resistance of the phenolic film-forming resin, but also promoting the rapid and effective decomposition of the diazonium photosensitizer due to the light absorption property of the titanium dioxide, accelerating the damage of the hydrogen bond structure in the photoresist composition, and having the advantages of high light sensitivity, high resolution, small line edge roughness and the like when light irradiation imaging.
Detailed Description
The photoresist composition provided by the invention belongs to a phenolic resin-diazonaphthoquinone positive photoresist composition, and before exposure, phenolic hydroxyl groups of the phenolic resin and the diazonaphthoquinone can form a stable six-membered ring structure through hydrogen bonding, so that dissolution of the phenolic resin in a developing solution (such as tetramethylammonium hydroxide) is inhibited; after being irradiated by ultraviolet light, the diazo naphthoquinone in the exposure area is decomposed, the six-membered ring structure is destroyed, and the diazo naphthoquinone emits N 2 Forming ketene which forms indene carboxylic acid when meeting water and is easy to dissolve in dilute alkali water, the phenolic resin is self-dissolved in alkali water, and the dissolution promoting effect is generated, thus obtaining the resist film in the unexposed areaA retained positive image.
In the photoresist composition provided by the invention, the titanium dioxide modified phenolic resin is added, and the titanium dioxide is grafted with the titanium dioxide, so that the titanium dioxide can absorb the energy of ultraviolet light, a photosensitizer coupled with the phenolic resin is rapidly and effectively decomposed, and the damage of a hydrogen bond structure in the photoresist composition is accelerated, so that the photoresist composition has the advantages of high photosensitive speed, high resolution, small line edge roughness and the like in light irradiation imaging.
The photoresist composition can be used for forming a photoresist pattern by the following steps:
first, the photoresist composition of the present invention is coated on a substrate by a roll coating method or a spin coating method. The substrate is preferably made of an oxide such as silicon, aluminum, indium, or tin. In order to remove the residual solvent of the photoresist composition coated on the substrate, vacuum drying may be performed under reduced pressure.
Then, the soft baking treatment is performed at 80-130 ℃ so that the solid components in the photoresist composition are evaporated to the solvent without thermal decomposition. The concentration of the solvent is preferably minimized by soft baking until the thickness of the photoresist film on the substrate is less than 2 μm.
Thereafter, the substrate on which the photoresist film is formed is exposed, particularly to ultraviolet rays, using an appropriate mask or template, thereby forming a pattern of a desired shape. The substrate after exposure is fully immersed in an alkaline developing aqueous solution until all or most of the photoresist film at the exposed part is dissolved. The aqueous developer solution is preferably an aqueous solution of ammonium hydroxide or tetramethylammonium hydroxide.
Then, the substrate with the exposed portions dissolved and removed is taken out of the developing solution, and then subjected to a hard baking treatment, thereby improving the adhesiveness and chemical resistance of the photoresist film. This heat treatment is preferably performed at a temperature below the softening point of the photoresist film, i.e., in the temperature range of 90-150 ℃.
Finally, the developed substrate is treated with an etching solution or a gaseous plasma, and at this time, only the exposed portions of the substrate are treated, and the portions of the substrate that are not exposed are protected by the photoresist film. After the substrate is processed in this way, the photoresist film is removed by an appropriate stripper, so that a fine circuit pattern can be formed on the substrate.
The technical scheme of the present invention will be described in detail by means of specific examples, which should be explicitly set forth for illustration, but should not be construed as limiting the scope of the present invention.
Example 1
A positive photoresist composition comprising the following raw material components by weight: 20g of titanium dioxide modified phenolic resin, 2g of 2,3, 4' -tetrahydroxybenzophenone-1, 2-diazonaphthoquinone-5-sulfonate (average degree of esterification 60%), 0.2g of polydimethylsiloxane, 10g of n-butyl acetate and 50g of propylene glycol methyl ether acetate;
the titanium dioxide modified phenolic resin is synthesized by the following method: adding the phenolic resin, the nano titanium dioxide modified by the 3-glycidoxypropyl triethoxysilane and the diethylenetriamine in a weight ratio of 9:1:0.1 into toluene, uniformly mixing, heating to 110 ℃, stirring and reacting for 2 hours, and distilling to remove a solvent to obtain the titanium dioxide modified phenolic resin;
in the synthesis of the titanium dioxide modified phenolic resin, the phenolic resin is synthesized by the following method: adding 65 parts by weight of m-cresol, 35 parts by weight of p-cresol, 5 parts by weight of 3, 5-xylenol, 60 parts by weight of formalin solution (36.9 wt%) and 1 part by weight of oxalic acid into a reaction kettle, heating to 40 ℃ under the protection of nitrogen for reaction for 1h, then reacting at 60 ℃ for 2h, finally adding 1 part by weight of oxalic acid, heating to 100 ℃ for reaction for 4h, and distilling to remove water and unreacted monomers to obtain the phenolic resin;
the 3-glycidoxy propyl triethoxysilane modified nano titanium dioxide is synthesized by the following method: 1 part by weight of 3-glycidoxypropyl triethoxysilane is dissolved in ethanol, heated to 60 ℃ and stirred for 30min, then 5 parts by weight of nano titanium dioxide (the average particle size is 30 nm) is added, heated to 80 ℃ and stirred for 4h for reaction, and the solvent is removed, so that the nano titanium dioxide modified by the 3-glycidoxypropyl triethoxysilane is obtained.
Example 2
A positive photoresist composition comprising the following raw material components by weight: 10g of titanium dioxide modified phenolic resin, 1g of 2,2', 4' -tetrahydroxybenzophenone-1, 2-diazonaphthoquinone-5-sulfonate (average degree of esterification 60%), 0.3g of polydimethylsiloxane, 10g of ethylene glycol monomethyl ether and 30g of propylene glycol methyl ether acetate;
the titanium dioxide modified phenolic resin is synthesized by the following method: adding the phenolic resin, the nano titanium dioxide modified by the 3-glycidoxypropyl trimethoxysilane and the diethylenetriamine in a weight ratio of 7:1:0.1 into toluene, uniformly mixing, heating to 110 ℃, stirring and reacting for 2 hours, and distilling to remove a solvent to obtain the titanium dioxide modified phenolic resin;
in the synthesis of the titanium dioxide modified phenolic resin, the phenolic resin is synthesized by the following method: adding 55 parts by weight of m-cresol, 45 parts by weight of p-cresol, 60 parts by weight of formalin solution (36.9 wt%) and 1 part by weight of oxalic acid into a reaction kettle, heating to 40 ℃ under the protection of nitrogen for reaction for 1h, reacting at 60 ℃ for 2h, adding 1 part by weight of oxalic acid, heating to 100 ℃ for reaction for 4h, and distilling to remove water and unreacted monomers to obtain the phenolic resin;
the 3-glycidoxy propyl trimethoxy silane modified nano titanium dioxide is synthesized by the following method: 1 part by weight of 3-glycidoxypropyl trimethoxysilane is dissolved in ethanol, heated to 60 ℃ and stirred for 30min, then 5 parts by weight of nano titanium dioxide (the average particle size is 30 nm) is added, heated to 80 ℃ and stirred for 4h for reaction, and the solvent is removed, so that the nano titanium dioxide modified by the 3-glycidoxypropyl trimethoxysilane is obtained.
Example 3
A positive photoresist composition comprising the following raw material components by weight: 30g of titanium dioxide modified phenolic resin, 5g of 2,3, 4' -tetrahydroxybenzophenone-1, 2-diazonaphthoquinone-5-sulfonate (average degree of esterification 75%), 0.1g of silicone oil, 20g of diethylene glycol dimethyl ether and 50g of propylene glycol methyl ether acetate;
the titanium dioxide modified phenolic resin is synthesized by the following method: adding the phenolic resin, the nano titanium dioxide modified by the 3-glycidoxypropyl methyl diethoxy silane and the diethylenetriamine in a weight ratio of 12:9:0.1 into toluene, uniformly mixing, heating to 110 ℃, stirring and reacting for 2 hours, and distilling to remove a solvent to obtain the titanium dioxide modified phenolic resin;
in the synthesis of the titanium dioxide modified phenolic resin, the phenolic resin is synthesized by the following method: adding 65 parts by weight of m-cresol, 35 parts by weight of p-cresol, 5 parts by weight of 3, 5-xylenol, 60 parts by weight of formalin solution (36.9 wt%) and 1 part by weight of oxalic acid into a reaction kettle, heating to 40 ℃ under the protection of nitrogen for reaction for 1h, then reacting at 60 ℃ for 2h, finally adding 1 part by weight of oxalic acid, heating to 100 ℃ for reaction for 4h, and distilling to remove water and unreacted monomers to obtain the phenolic resin;
the 3-glycidoxy propyl methyl diethoxy silane modified nano titanium dioxide is synthesized by the following method: 1 part by weight of 3-glycidoxypropyl methyl diethoxy silane is dissolved in ethanol, heated to 60 ℃ and stirred for 30min, then 5 parts by weight of nano titanium dioxide (the average particle size is 30 nm) is added, heated to 80 ℃ and stirred for 4h for reaction, and the solvent is removed, so that the nano titanium dioxide modified by the 3-glycidoxypropyl methyl diethoxy silane is obtained.
Comparative example 1
A positive photoresist composition comprising the following raw material components by weight: 20g of phenolic resin, 3g of 2,3, 4' -tetrahydroxybenzophenone-1, 2-diazonaphthoquinone-5-sulfonate (average degree of esterification 60%), 0.2g of polydimethylsiloxane, 10g of n-butyl acetate and 50g of propylene glycol methyl ether acetate.
The phenolic resin is synthesized by the following method: adding 65 parts by weight of m-cresol, 35 parts by weight of p-cresol, 5 parts by weight of 3, 5-xylenol, 60 parts by weight of formalin solution (36.9 wt%) and 1 part by weight of oxalic acid into a reaction kettle, heating to 40 ℃ under the protection of nitrogen for reaction for 1h, reacting at 60 ℃ for 2h, finally adding 1 part by weight of oxalic acid, heating to 100 ℃ for reaction for 4h, and distilling to remove water and unreacted monomers to obtain the phenolic resin.
The preparation methods of the photoresist compositions described above with respect to examples 1 to 3 and comparative example 1 include: mixing phenolic resin, a photosensitizer, an organosilicon leveling agent and an organic solvent, and stirring for 4 hours at 50 ℃ to obtain the photoresist composition.
The photoresist compositions obtained from the above examples 1 to 3 and comparative example 1 were subjected to the following test, and the results are shown in table 1:
coating the photoresist compositions obtained in examples 1 to 3 and comparative example 1 on a silicon wafer using a spin coater, and then, drying the silicon wafer coated with the photoresist composition in vacuum and then baking at 100 ℃ for 60 seconds to obtain a photoresist layer having a thickness of 0.75 μm;
and (3) detecting the mask plate by adopting a standard L/S=1:1, respectively exposing the obtained photoresist layer by using a light source of an I line (with the wavelength of 365 nm), and then respectively developing the exposed photoresist layer by using a tetramethyl ammonium hydroxide solution with the mass fraction of 2.38w% as a developing solution for 60S to obtain a photoresist pattern.
1) Photosensitivity: expressed as the minimum exposure to give a 0.5 μm 1:1 isopipe pattern.
2) Resolution ratio: finding out the minimum line width, carrying out SEM test on the slice, and determining the size of the slice, namely the resolution.
3) Line edge roughness: observation with an electron microscope was performed according to the following criteria: good-the line edge is a straight line, and the edge is narrow; the difference-line edge is not a line, has a width, and is wide.
TABLE 1 test results of the photoresist compositions obtained corresponding to examples 1-3 and comparative examples 1-1
As can be seen from table 1 above, the photoresist compositions of the examples are significantly more excellent in terms of photospeed and resolution than the comparative examples.
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention.
Claims (9)
1. A positive photoresist composition is characterized by comprising the following raw material components in parts by weight: 10-30 parts of titanium dioxide modified phenolic resin, 1-5 parts of photosensitizer, 0.1-0.3 part of organosilicon leveling agent and 40-70 parts of organic solvent;
wherein the titanium dioxide modified phenolic resin is phenolic resin with molecular chains grafted with nano titanium dioxide;
the phenolic resin with the molecular chain grafted with the nano titanium dioxide is formed by ring-opening addition reaction of the phenolic resin and the nano titanium dioxide modified by the epoxy group-containing silane coupling agent;
the nano titanium dioxide modified by the epoxy group-containing silane coupling agent is obtained by heating the epoxy group-containing silane coupling agent and the nano titanium dioxide in an alcohol solvent;
the epoxy group-containing silane coupling agent is at least one of 3-glycidoxypropyl trimethoxy silane, 3-glycidoxypropyl methyl diethoxy silane or 3-glycidoxypropyl triethoxy silane.
2. The positive photoresist composition according to claim 1, wherein the phenolic resin is a cresol-formaldehyde condensed resin having a molecular weight of 2000-20000.
3. The positive photoresist composition according to claim 1, wherein the weight ratio of the phenolic resin to the nano titanium dioxide modified by the epoxy group-containing silane coupling agent is 7-12:1.
4. A positive photoresist composition according to any of claims 1-3, where the photosensitizer is an ester of 2,3, 4' -tetrahydroxybenzophenone and 2,1, 5-diazonaphthoquinone sulfonyl chloride or an ester of 2,2', 4' -tetrahydroxybenzophenone and 2,1, 5-diazonaphthoquinone sulfonyl chloride.
5. The positive photoresist composition according to claim 4, wherein the degree of esterification of the esterified substance is 50 to 80%.
6. A positive photoresist composition according to any of claims 1-3, wherein the silicone leveling agent is at least one of polydimethylsiloxane or silicone oil.
7. A positive photoresist composition according to any of claims 1-3, wherein the organic solvent is at least one of ethyl lactate, ethyl acetate, n-butyl acetate, ethylene glycol monomethyl ether, diethylene glycol dimethyl ether, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, or diethylene glycol monomethyl ether.
8. The positive photoresist composition of any one of claims 1-3, wherein the positive photoresist composition further comprises at least one of a colorant, a plasticizer, or a surfactant.
9. A method of preparing a positive photoresist composition according to any one of claims 1 to 8, comprising: and uniformly mixing the titanium dioxide modified phenolic resin, the photosensitizer, the organosilicon leveling agent and the organic solvent.
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| US6534235B1 (en) * | 2000-10-31 | 2003-03-18 | Kansai Research Institute, Inc. | Photosensitive resin composition and process for forming pattern |
| JP4295937B2 (en) * | 2000-12-05 | 2009-07-15 | 株式会社Ｋｒｉ | Active ingredient and photosensitive resin composition using the same |
| WO2002046841A1 (en) * | 2000-12-05 | 2002-06-13 | Kansai Research Institute. Inc. | Active components and photosensitive resin compositions containing the same |
| CN102432785B (en) * | 2011-09-14 | 2013-06-12 | 武汉理工大学 | Method for preparing in-situ dispersion nano polybasic graft modified phenolic resin |
| CN109062008B (en) * | 2018-08-21 | 2022-03-11 | 西陇科学股份有限公司 | Ultraviolet positive photoresist |
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