CN108003273B - PH response type polymer, preparation method thereof and photoresist composition - Google Patents
PH response type polymer, preparation method thereof and photoresist composition Download PDFInfo
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- CN108003273B CN108003273B CN201711338513.3A CN201711338513A CN108003273B CN 108003273 B CN108003273 B CN 108003273B CN 201711338513 A CN201711338513 A CN 201711338513A CN 108003273 B CN108003273 B CN 108003273B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
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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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/282—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing two or more oxygen atoms
Abstract
The invention provides a pH response type polymer, a preparation method thereof and a photoresist composition. The photoresist composition comprises the following components in percentage by weight: 1-10% of pH response type polymer with a structure shown in formula I or formula II, 5-30% of resin, 0.1-1% of photosensitizer and the balance of solvent, wherein m is an integer of 20-100, n is an integer of 20-100, x is an integer of 1-4, R1Is a methyl group or a hydrogen atom, R2Is methyl or hydrogen atom, and R is methyl or hydrogen atom. The photoresist composition has the characteristic of volume shrinkage under an acidic condition, can prevent undercut phenomenon in the etching process of films such as a grid electrode, a source electrode, a drain electrode, a metal oxide pixel electrode, a metal oxide active layer and the like, and reduces the incidence rate of short circuit type defects, thereby improving the product yield.
Description
Technical Field
The invention relates to the field of thin film transistor array manufacturing, in particular to a pH response type polymer and a pH response type photoresist composition.
Background
The photolithography process is an essential process in the process of manufacturing the thin film transistor array, and plays a role in pattern transfer. The designed mask pattern is transferred to the film by cleaning, photoresist coating, soft baking, exposure, developing, post baking and other processes, and then a target pattern is formed by etching and photoresist stripping processes.
The main component of the photoresist is a polymer composition containing photosensitive groups, and the photosensitive groups of the photoresist are chemically changed under the condition of ultraviolet irradiation, so that the solubility of the photosensitive parts and the light-shielding parts of the photoresist in a developing solution is different, and the pattern transfer is realized after the development.
The wet etching process is mainly suitable for etching a metal film layer and a metal oxide conductor or a semiconductor in the manufacturing process of the thin film transistor array. The wet etching process is isotropic etching, and the instant etching liquid not only can etch the metal film layer downwards, but also can perform diffusion etching in the horizontal direction. As shown in fig. 1, if the adhesion between the protective photoresist 12 on the metal film 11 and the metal film 11 is too large, an undercut (undercut) is likely to occur, and a slope or a curved surface is formed on the side surface of the metal film 11. The undercut is liable to cause the subsequent insulating dielectric film layer to break, resulting in poor short circuit and affecting the product yield.
Disclosure of Invention
In view of the disadvantages of the prior art, it is an object of the present invention to provide a pH-responsive photoresist composition that can be volume-shrunk in an acidic environment, thereby preventing the occurrence of undercut phenomenon.
In order to achieve the purpose, the invention adopts the following technical scheme:
a pH responsive polymer having the structure of formula I wherein m is an integer of 20 to 100, n is an integer of 20 to 100, x is an integer of 1 to 4, R1Is a methyl group or a hydrogen atom, R2Is methylOr a hydrogen atom.
In one embodiment of the pH responsive polymer of the present invention, m is an integer of 30 to 50 and n is an integer of 30 to 50.
The present invention also provides a method for preparing a pH-responsive polymer having the structure of formula i, comprising:
adding a (meth) acrylic acid monomer and a (meth) acrylic acid polyethylene glycol ester monomer to a dispersant;
adding an initiator; and
heating to initiate the polymerization of the (methyl) acrylic acid monomer and the (methyl) acrylic acid polyethylene glycol ester monomer to obtain the pH response type polymer with the structure shown in the formula I.
In one embodiment of the process of the present invention, the dispersant is N, N-dimethylformamide, N-dimethylacetamide, toluene, cyclohexanone, dioxane or N-methylpyrrolidone, and the initiator is azobisisobutyronitrile, azobisisoheptonitrile, dimethyl azobisisobutyrate, dibenzoyl peroxide, benzoyl peroxide tert-butyl peroxide or methyl ethyl ketone peroxide.
In another embodiment of the method of the present invention, the temperature of the heating is 70 to 110 ℃.
In another aspect, the present invention provides a pH responsive polymer having the structure of formula II wherein m is an integer of 20 to 100 and n is an integer of 20 to 100, R is a methyl group or a hydrogen atom.
In one embodiment of the pH responsive polymer of the present invention, m is an integer of 30 to 50 and n is an integer of 30 to 50.
The present invention also provides a method for preparing a pH-responsive polymer having the structure of formula ii, comprising:
carrying out esterification reaction on polyethylene glycol and 2-bromopropionyl bromide or 2-chloropropionyl chloride to obtain an intermediate product;
and mixing the intermediate product with (methyl) acrylic acid, heating under the action of a catalyst, and polymerizing to obtain the pH response type polymer with the structure of the formula II.
In one embodiment of the process of the present invention, the catalyst is cuprous bromide or cuprous chloride.
In another embodiment of the process of the present invention, the temperature of the heating is 50 to 120 ℃.
In another aspect, the present invention provides a photoresist composition, comprising, by weight: 1-10% of any one or more pH response type polymers, 5-30% of resin, 0.1-1% of photosensitizer and the balance of solvent.
In one embodiment of the photoresist composition of the present invention, the resin is a phenol resin or an acryl resin.
In another embodiment of the photoresist composition of the present invention, the photosensitizer is a diazonaphthoquinone photosensitizer, or a combination of one or more of nitroaniline, anthraquinone, benzophenone, and N-acetyl-4-nitronaphthylamine.
In another embodiment of the photoresist composition of the invention, the solvent is one or a combination of propylene glycol monomethyl ether acetate, N-methylpyrrolidone, glycol ethers, ethylene glycol alkyl ether acetate, diethylene glycol, ethoxyethyl acetate, dimethoxyacetaldehyde, propylene glycol methyl ether acetate, ethyl 3-ethoxypropionate, propylene glycol methyl ether, and ethylene glycol ethyl acetate.
In another embodiment of the photoresist composition of the invention, the photoresist composition further comprises 0.1-1% by weight of an additive, wherein the additive is one or more of a polymerization inhibitor, a leveling agent, a defoaming agent and a stabilizer.
The photoresist composition has the characteristic of volume shrinkage under an acidic condition, can prevent undercut phenomenon in the etching process of films such as a grid electrode, a source electrode, a drain electrode, a metal oxide pixel electrode, a metal oxide active layer and the like, and reduces the incidence rate of short circuit type defects, thereby improving the product yield.
Drawings
FIG. 1 is a diagram illustrating an undercut phenomenon in the prior art;
wherein the reference numerals are as follows:
11: metal film layer
12: photoresist
Detailed Description
The technical solution of the present invention is further explained below according to specific embodiments. The scope of protection of the invention is not limited to the following examples, which are set forth for illustrative purposes only and are not intended to limit the invention in any way.
It is to be understood that the drawings disclosed herein are not necessarily drawn to scale as actual devices or elements may be. The shapes and thicknesses of the embodiments may be exaggerated in the drawings in order to clearly show the features of the embodiments of the present disclosure. Furthermore, the structures and devices in the drawings are schematically depicted in order to clearly illustrate the features of the embodiments of the present disclosure.
In one embodiment, the present invention provides a pH-responsive polymer having the structure of formula i below.
The pH-responsive polymer with the structure of formula I is a poly (meth) acrylic acid-poly (meth) acrylic acid polyethylene glycol ester copolymer, wherein m is an integer of 20-100, preferably 30-50, n is an integer of 20-100, preferably 30-50, x is an integer of 1-4, R1Is a methyl group or a hydrogen atom, R2Is a methyl group or a hydrogen atom. The pH responsive polymer has a number average molecular weight of 5000 to 30000 g/mol.
The poly (meth) acrylic acid-poly (meth) acrylic acid polyethylene glycol ester copolymer of formula i can be prepared by the following reaction:
specifically, the (meth) acrylic acid monomer and the (meth) acrylic acid polyethylene glycol ester are added into the dispersant according to the preset ratio of m and n, then the initiator is added, and the mixture is heated to generate free radicals to initiate the polymerization of the two monomers, so that the pH response type polymer with the structure shown in the formula I is obtained.
The polyethylene glycol (meth) acrylate may be diethylene glycol (meth) acrylate, triethylene glycol (meth) acrylate, tetraethylene glycol (meth) acrylate, or pentaethylene glycol (meth) acrylate.
The dispersant used in the preparation process is one or more of N, N-dimethylformamide, N-dimethylacetamide, toluene, cyclohexanone, dioxane or N-methylpyrrolidone, the initiator used is one or more of AIBN (azobisisobutyronitrile), azobisisoheptonitrile, dimethyl azobisisobutyrate, BPO (dibenzoyl peroxide), benzoyl peroxide tert-butyl ester or methyl ethyl ketone peroxide, the heating temperature is 70-110 ℃, and the reaction time is about 5-10 hours.
In another embodiment, the present invention provides a pH-responsive polymer having the structure of formula ii below.
The pH response type polymer with the structure shown in the formula II is a poly (methyl) acrylic acid-polyethylene glycol copolymer, wherein m is an integer of 20-100, preferably 30-50, n is an integer of 20-100, preferably 30-50, and R is methyl or hydrogen atom. The pH responsive polymer has a number average molecular weight of 5000 to 30000 g/mol.
The poly (meth) acrylic acid-polyethylene glycol copolymer represented by formula ii can be prepared by the following reaction:
specifically, polyethylene glycol and 2-bromopropionyl bromide or 2-chloropropionyl chloride are added into triethylamine (EtN3) to carry out esterification reaction on the polyethylene glycol and the 2-bromopropionyl bromide or 2-chloropropionyl chloride to obtain an intermediate product, and then the intermediate product is mixed with a (methyl) acrylic acid monomer, heated under the action of a catalyst and polymerized to obtain the pH response type polymer with the structure of formula II.
The catalyst used in the preparation process can be cuprous bromide or cuprous chloride, the heating temperature is 50-120 ℃, and the reaction time is about 5-10 hours.
The photoresist composition comprises the following components in percentage by weight: 1-10% of pH response type polymer shown in formula I and/or formula II, 5-30% of resin, 0.1-1% of photosensitizer and the balance of solvent, preferably 5% of pH response type polymer, 25% of resin, 0.2% of photosensitizer and the balance of solvent.
The pH-responsive polymer represented by the formula I and the pH-responsive polymer represented by the formula II may be used either singly or as a mixture of both, and the mixing ratio of both is not limited.
When the photoresist composition is a positive photoresist, a phenolic resin can be used as a main resin in the photoresist, and a diazonaphthoquinone photosensitizer is matched. The phenol resin can be prepared by reacting a phenol compound with an aldehyde compound or a ketone compound in the presence of an acidic catalyst. Diazonaphthoquinone photosensitizer can be obtained by reacting diazonaphthoquinone sulfonyl halide compound with phenol compound in the presence of weak base.
When the photoresist composition is a negative photoresist, an acrylic resin can be used as a main resin in the photoresist, and one or more of nitroaniline, anthraquinone, benzophenone and N-acetyl-4-nitronaphthylamine can be used as a photosensitizer.
The solvent in the photoresist composition is one or a combination of more of propylene glycol monomethyl ether acetate, N-methyl pyrrolidone, glycol ether, ethylene glycol alkyl ether acetate, diethylene glycol, ethoxyethyl acetate, dimethoxyacetaldehyde, propylene glycol methyl ether acetate, ethyl 3-ethoxypropionate, propylene glycol methyl ether and ethylene glycol ethyl acetate, and can well dissolve the pH responsive polymer, resin and photosensitizer.
In order to further improve the performance of the photoresist composition, 0.1-1 wt% of additive can be added, and the additive is one or more of polymerization inhibitor, leveling agent, defoaming agent and stabilizer.
The polymerization inhibitor can be one or a combination of more of hydroquinone, 2-sec-butyl-4, 6-dinitrophenol, p-tert-butyl catechol and 2, 5-di-tert-butyl hydroquinone, the flatting agent can be acrylic compounds, organosilicon compounds, fluorocarbon compounds and the like, the defoaming agent can be emulsified silicone oil, high-carbon alcohol fatty acid ester compounds, polyoxyethylene polyoxypropylene pentaerythritol ether, polyoxyethylene polyoxypropylene amine ether, polyoxypropylene glycerol ether, polyoxypropylene polyoxyethylene glycerol ether, polydimethylsiloxane and the like, and the stabilizer can be at least one of isoamyl alcohol, n-hexyl alcohol, glycerol and n-hexane.
The preparation process of the photoresist composition is very simple, and the pH response type polymer, the resin, the photosensitizer and optional additives can be added into a solvent according to a proportion and can be completely dissolved to obtain the photoresist composition.
When the common photoresist is used for etching, if the adhesive force between the photoresist and the metal film surface is large, the etching liquid is difficult to drill between the photoresist and the metal film surface, the surface film surface is protected, but due to the action of gravity, the etching liquid can diffuse downwards and leftwards and rightwards, and the surface metal film layer has relatively less loss amount due to the protection of the photoresist, so that an undercut phenomenon is formed.
The photoresist composition is prepared from pH response type polymers, has the characteristic of volume shrinkage under an acidic condition, and has the advantages that after the photoresist contacts acidic etching liquid, the volume shrinkage is generated on the surfaces of metal and metal oxide, the photoresist protection part on the surface of a metal film is gradually reduced, the metal eaten by the etching liquid on the surface is gradually enlarged, so that the undercut phenomenon can not occur, the occurrence rate of short circuit type defects is reduced, and the product yield is improved.
When the thin film transistor array substrate is manufactured, the photoresist composition can be used for carrying out a Photo process (a photoetching process comprising photoresist coating, exposure and development) on a grid electrode, a source electrode, a drain electrode, a metal oxide pixel electrode, a metal oxide active layer and the like, and carrying out a wet etching process, so that the thin film transistor array substrate is manufactured.
The thin film transistor array substrate manufactured by the above photolithography process may be applicable to various display devices, such as LCDs or OLEDs.
It is to be understood that (meth) acrylic acid in the present invention means that it may be any one of acrylic acid and methacrylic acid.
Unless otherwise defined, all terms used herein have the meanings that are commonly understood by those skilled in the art.
The present invention will be described in further detail with reference to examples.
Examples
Example 1 preparation of pH responsive Polymer
30g of acrylic monomer and 96.5g of triethylene glycol acrylate monomer are added into 1000ml of cyclohexanone dispersant, 3.28g of initiator AIBN (azobisisobutyronitrile) is added, the mixture is heated to 90 ℃ and reacts to generate free radicals to initiate the polymerization of the two monomers, and the pH response type polymer with the structure of the formula I is obtained.
The number average molecular weight of the pH responsive polymer was found to be 11000 g/mol.
The reaction process is as follows.
Example 2 preparation of pH responsive Polymer
60g of polyethylene glycol (with the number average molecular weight of 6000) and 2.16g of 2-bromopropionyl bromide are added into 500mL of triethylamine (EtN3) to carry out esterification reaction on the polyethylene glycol and the 2-bromopropionyl bromide to obtain an intermediate product with a structure shown in a formula III.
Then, 61g of the intermediate product is mixed with 50g of acrylic acid monomer, 0.144g of cuprous bromide is added to the mixture to perform catalysis, the solvent is 1000mL of cyclohexanone, and the mixture is heated to 100 ℃ to initiate polymerization of the acrylic acid monomer, so that the pH response type polymer with the structure of the formula II is obtained.
The number average molecular weight of the pH responsive polymer was found to be 11500 g/mol.
The reaction process is as follows:
EXAMPLE 3 preparation of Photoresist composition
According to the weight percentage, 5 percent of the pH response type polymer prepared in the embodiment 1, 15 percent of phenolic resin, 0.2 percent of diazonaphthoquinone photosensitizer and 1 percent of additive are added into a solvent such as propylene glycol monomethyl ether acetate, and the photoresist composition is prepared after complete dissolution.
The photoresist composition was placed under an acidic condition at a pH of about 3.0, and the volume shrinkage thereof was measured to be 25%.
EXAMPLE 4 preparation of Photoresist composition
According to the weight percentage, 5 percent of the pH response type polymer prepared in the embodiment 2, 15 percent of phenolic resin, 0.2 percent of diazonaphthoquinone photosensitizer and 1 percent of additive are added into solvents such as propylene glycol monomethyl ether acetate and the like, and the photoresist composition is prepared after complete dissolution.
The photoresist composition was placed under an acidic condition at a pH of about 3.0, and the volume shrinkage thereof was measured to be 20%.
In summary, the photoresist composition of the invention has the property of volume shrinkage under acidic conditions, and can prevent undercut phenomenon during etching of metal or metal oxide film layers such as gate, source, drain, metal oxide pixel electrode, metal oxide active layer, etc., and reduce the occurrence rate of short circuit defects, thereby improving the product yield.
It should be noted by those skilled in the art that the described embodiments of the present invention are merely exemplary and that various other substitutions, alterations, and modifications may be made within the scope of the present invention. Accordingly, the present invention is not limited to the above-described embodiments, but is only limited by the claims.
Claims (6)
1. A photoresist composition comprising, by weight percent: 1-10% of pH response type polymer, 5-30% of resin, 0.1-1% of photosensitizer and the balance of solvent,
wherein the pH response type polymer has a structure shown in the following formula I,
wherein m is an integer of 20 to 100, n is an integer of 20 to 100, x is an integer of 1 to 4, R1Is a methyl group or a hydrogen atom, R2Is a methyl group or a hydrogen atom.
2. The photoresist composition of claim 1, where m is an integer from 30 to 50 and n is an integer from 30 to 50.
3. The photoresist composition of claim 1, wherein the resin is a phenolic resin or an acrylic resin.
4. The photoresist composition of claim 1, wherein the photosensitizer is a diazonaphthoquinone photosensitizer, or a combination of one or more of nitroaniline, anthraquinone, benzophenone, and N-acetyl-4-nitronaphthylamine.
5. The photoresist composition of claim 1, wherein the solvent is one or a combination of propylene glycol monomethyl ether acetate, N-methyl pyrrolidone, glycol ethers, ethylene glycol alkyl ether acetate, diethylene glycol, ethoxyethyl acetate, dimethoxyacetaldehyde, propylene glycol methyl ether acetate, ethyl 3-ethoxypropionate, propylene glycol methyl ether, and ethylene glycol ethyl acetate.
6. The photoresist composition according to any one of claims 1 to 5, further comprising 0.1-1% by weight of an additive which is a combination of one or more of a polymerization inhibitor, a leveling agent, a defoaming agent and a stabilizer.
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| CN102702987A (en) * | 2012-03-21 | 2012-10-03 | 北京京东方光电科技有限公司 | Frame sealant composition, liquid crystal pollution prevention method, liquid crystal display panel and display device |
| CN103145908A (en) * | 2013-03-25 | 2013-06-12 | 京东方科技集团股份有限公司 | Alkali soluble resin as well as preparation method and application thereof |
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