CN114167684A - Photoresist composition, preparation method and application thereof, and method for forming photoresist pattern - Google Patents
Photoresist composition, preparation method and application thereof, and method for forming photoresist pattern Download PDFInfo
- Publication number
- CN114167684A CN114167684A CN202111483647.0A CN202111483647A CN114167684A CN 114167684 A CN114167684 A CN 114167684A CN 202111483647 A CN202111483647 A CN 202111483647A CN 114167684 A CN114167684 A CN 114167684A
- Authority
- CN
- China
- Prior art keywords
- acid
- photoresist
- poly
- photoresist composition
- hydroxystyrene
- 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.)
- Pending
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 98
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims abstract description 43
- 229920001519 homopolymer Polymers 0.000 claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 claims abstract description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003431 cross linking reagent Substances 0.000 claims description 12
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 239000003377 acid catalyst Substances 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- KLJLQTJYNGGTIU-FOWTUZBSSA-N [(e)-1-phenylethylideneamino] benzoate Chemical compound C=1C=CC=CC=1C(/C)=N/OC(=O)C1=CC=CC=C1 KLJLQTJYNGGTIU-FOWTUZBSSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 claims description 7
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 6
- 230000005855 radiation Effects 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- VJDHKUHTYJLWPV-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-(2-methylprop-2-enoyloxy)piperidine-1-carboxylate Chemical compound C(C(=C)C)(=O)OC1CCN(CC1)C(=O)OCC1=C(C=CC=C1)[N+](=O)[O-] VJDHKUHTYJLWPV-UHFFFAOYSA-N 0.000 claims description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- UCRXZJYCOMRCER-UHFFFAOYSA-N 2-[n,n'-di(propan-2-yl)carbamimidoyl]-1,1,3,3-tetramethylguanidine Chemical compound CC(C)NC(=NC(C)C)N=C(N(C)C)N(C)C UCRXZJYCOMRCER-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 229940116333 ethyl lactate Drugs 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims description 4
- 229960001597 nifedipine Drugs 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- -1 tetramethylbiguanide n-butyltriphenylborate Chemical compound 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 238000011161 development Methods 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 238000005530 etching Methods 0.000 abstract description 9
- 238000004132 cross linking Methods 0.000 abstract description 8
- 238000001312 dry etching Methods 0.000 abstract description 8
- 125000006239 protecting group Chemical group 0.000 abstract description 8
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
- 238000000276 deep-ultraviolet lithography Methods 0.000 abstract description 3
- 230000036211 photosensitivity Effects 0.000 abstract description 3
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000002313 adhesive film Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 238000009616 inductively coupled plasma Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JHNRZXQVBKRYKN-VQHVLOKHSA-N (ne)-n-(1-phenylethylidene)hydroxylamine Chemical compound O\N=C(/C)C1=CC=CC=C1 JHNRZXQVBKRYKN-VQHVLOKHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001046 glycoluril group Chemical group [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/322—Aqueous alkaline compositions
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention provides a photoresist composition, a preparation method and application thereof, and a method for forming a photoresist pattern, and particularly relates to the technical field of photoresist. The photoresist composition comprises a poly-p-hydroxystyrene homopolymer and a photoinduced deactivator, and the mass ratio of the poly-p-hydroxystyrene homopolymer to the photoinduced deactivator is 100-600: 2-50. The weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is 1000-20000. The photoresist composition has strong photosensitivity, and after exposure by adopting a light source of 248nm deep ultraviolet lithography, the exposure dose can be reduced to 10mJ/cm under the film thickness of 500nm2The following. The poly-p-hydroxystyrene homopolymer has no protective group and can participate in crosslinking, so the poly-p-hydroxystyrene homopolymer has higher carbon atom content and obviously improves the dry etching resistanceThe etching ratio is improved, the production efficiency of customers is greatly improved, and the production cost is reduced.
Description
Technical Field
The invention relates to the technical field of photoresist, in particular to a photoresist composition, a preparation method and application thereof, and a method for forming a photoresist pattern.
Background
Deep ultraviolet positive photoresists for exposure to KrF excimer lasers (248nm) have wide and important applications in the market. The photoresist is mainly used for manufacturing chips with critical dimensions of 0.25-0.15 micrometers, and belongs to a neck clamp project.
The existing KrF photoresist system is mainly based on poly-p-hydroxystyrene and derivatives thereof, and the reaction mechanism of the KrF photoresist system is deprotection.Because the resin contains a large number of protecting groups and methacrylate monomers, the existence of the protecting groups reduces the content of carbon atoms in the adhesive film, and the content of the carbon atoms directly influences the dry etching resistance of the adhesive film, so that the dry etching resistance of the existing KrF positive photoresist cannot be continuously improved, and the technical effect is poor. Meanwhile, the protective group in the resin needs to be removed in the reaction, but the deprotection reaction needs more catalysts, so the exposure dose is usually 20-30 mJ/cm2The temperature cannot be continuously reduced, and the production efficiency of a chip factory is reduced.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
One of the objectives of the present invention is to provide a photoresist composition, which solves the technical problems of high exposure dose and poor dry etching resistance of the photoresist film in the prior art.
The second purpose of the present invention is to provide a method for preparing a photoresist composition, which has simple process, large handling capacity, suitability for mass production and low cost.
The invention also aims to provide the application of the photoresist composition in manufacturing integrated circuits, which improves the production efficiency of the integrated circuits and reduces the production cost.
The fourth objective of the present invention is to provide a method for forming a photoresist pattern, which ensures that the formed pattern meets the actual process requirements and realizes a better photoresist pattern.
In order to solve the technical problems, the invention adopts the following technical scheme:
in a first aspect of the invention, a photoresist composition is provided comprising a poly (p-hydroxystyrene) homopolymer and a photo-deactivator.
Wherein the mass ratio of the poly-p-hydroxystyrene homopolymer to the photoinduced deactivator is 100-600: 2-50.
Alternatively, the poly (p-hydroxystyrene) homopolymer has the structural formula:
wherein n is an integer greater than 1.
Preferably, the weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is 1000-20000.
Preferably, the photo-deactivator comprises at least one of acetophenone O-benzoyl oxime, nifedipine, 2-nitrophenylmethyl 4-methacryloxypiperidine-1-carboxylate, 1, 2-diisopropyl-3- [ bis (dimethylamino) methylene ] guanidine 2- (3-benzoylphenyl) propionate, and 1, 2-dicyclohexyl-4, 4,5,5 tetramethylbiguanide n-butyltriphenylborate.
Preferably, the composition comprises the following components in parts by mass: 10-60 parts of poly p-hydroxystyrene homopolymer, 2-20 parts of cross-linking agent, 0.2-5 parts of acid catalyst and 0.2-5 parts of photoinduced deactivator.
Preferably, the paint also comprises 5-90 parts of solvent by mass.
Optionally, the cross-linking agent comprises at least one of glycoluril, glycoluril derivatives, 1, 3-bis-methylol urea, 1, 3-dimethyl-2-imidazolidinone.
Preferably, the acidic catalyst comprises an organic acid and/or an inorganic acid.
Preferably, the organic acid comprises at least one of formic acid, acetic acid, propionic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid and p-toluenesulfonic acid.
Preferably, the inorganic acid includes at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and hydrofluoric acid.
Preferably, the solvent comprises an organic solvent.
Preferably, the organic solvent includes at least one of glycol methyl ether, propylene glycol methyl ether acetate, ethyl acetate, and ethyl lactate.
The second aspect of the present invention provides a method for preparing the photoresist composition, which comprises mixing the poly-p-hydroxystyrene homopolymer, the photo-deactivating agent, optionally the cross-linking agent, optionally the acid catalyst and optionally the solvent.
A third aspect of the invention provides the use of the photoresist composition in the manufacture of integrated circuits.
A fourth aspect of the present invention provides a method of forming a photoresist pattern, the method comprising the steps of:
step A: coating a photoresist composition on the target layer to form a photoresist layer;
and B: pre-baking the photoresist layer and then exposing the photoresist layer with actinic radiation to obtain an exposed photoresist layer;
and C: and (4) baking the exposed photoresist layer, adding a developing solution, and developing to obtain the photoresist pattern.
Optionally, the pre-baking temperature is 90-110 ℃.
Preferably, the pre-baking time is 30-90 s.
Preferably, the temperature of the intermediate drying is 120-.
Preferably, the baking time is 30-90 s.
Optionally, a pre-bake, post-exposure to actinic radiation in step B results in a photoresist layer to be exposed.
Preferably, the film thickness of the photoresist layer to be exposed is 500 nm.
Preferably, the developing solution is added in step C for development.
Preferably, the developer solution comprises a tetramethylammonium hydroxide solution, a potassium hydroxide solution or a sodium hydroxide solution.
Compared with the prior art, the invention has at least the following beneficial effects:
the photoresist composition provided by the invention uses a photoinduced deactivator to react with the poly-p-hydroxystyrene homopolymer, and the photoinduced deactivator generates intermediate substances to prevent the cross-linking reaction of the poly-p-hydroxystyrene homopolymer when being exposed, so that the photoresist composition is dissolved in a developing solution to form a positive image. The photoresist composition has strong photosensitivity, and after exposure by adopting a light source of 248nm deep ultraviolet lithography, the exposure dose can be reduced to 10mJ/cm under the film thickness of 500nm2The following. Upon exposure to light, the photoinactivation agent forms a basic compound that deactivates the acidic catalyst and does not catalyze the poly (p-hydroxystyrene) homopolymerThe silicon dioxide film has the advantages that the silicon dioxide film has a crosslinking reaction with a crosslinking agent, but can be subjected to the crosslinking reaction in a non-exposure area, and has a higher carbon atom content due to no protective group, so that the dry etching resistance is obviously improved, the etching ratio is improved, the production efficiency of customers is greatly improved, and the production cost is reduced.
The preparation method of the photoresist composition provided by the invention has the advantages of simple process, large processing capacity, suitability for mass production and low cost.
The application of the photoresist composition provided by the invention in manufacturing integrated circuits improves the production efficiency of the integrated circuits and reduces the production cost.
The method for forming the photoresist pattern ensures that the formed pattern meets the actual process requirement and realizes a better photoresist pattern.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. The components of embodiments of the present invention may be arranged and designed in a wide variety of different configurations.
In a first aspect of the invention, a photoresist composition is provided comprising a poly (p-hydroxystyrene) homopolymer and a photo-deactivator.
Wherein the mass ratio of the poly-p-hydroxystyrene homopolymer to the photoinduced deactivator is 100-600: 2-50.
The photoresist composition provided by the invention uses a photoinduced deactivator to react with the poly-p-hydroxystyrene homopolymer, and the photoinduced deactivator generates intermediate substances to prevent the cross-linking reaction of the poly-p-hydroxystyrene homopolymer when being exposed, so that the photoresist composition is dissolved in a developing solution to form a positive image. The photoresist composition has strong photosensitivity, and after exposure by adopting a light source of 248nm deep ultraviolet lithography, the exposure dose can be reduced to 10mJ/cm under the film thickness of 500nm2The following. The poly (p-hydroxystyrene) homopolymer has no protective group, can participate in crosslinking, and has high carbon contentThe atomic content obviously improves the dry etching resistance, improves the etching ratio, greatly improves the production efficiency of customers and reduces the production cost.
When the mass ratio of the poly-p-hydroxystyrene homopolymer to the photoinduced deactivator is lower than 100:50, the photoinduced deactivator cannot be normally dissolved in a solvent due to too high ratio, the uniformity of a photoresist film is reduced, and the dry etching resistance is reduced; when the mass ratio of the poly (p-hydroxystyrene) homopolymer to the photo-deactivator is higher than 600:2, the content of the photo-deactivator is too low to be effectively deactivated.
In some preferred embodiments of the present invention, the mass ratio of the poly (p-hydroxystyrene) homopolymer to the photo-deactivator is typically, but not limited to, 100:2, 100:30, 100:50, 200:2, 200:30, 200:50, 300:2, 300:30, 300:50, 400:2, 400:30, 400:50, 500:2, 500:30, 500:50, 600:2, 600:30, or 600: 50.
Alternatively, the poly (p-hydroxystyrene) homopolymer has the structural formula:
wherein n is an integer greater than 1.
Preferably, the weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is 1000-20000.
The poly-p-hydroxystyrene homopolymer used in the original 248nm positive photoresist system is acid-sensitive resin, contains a large amount of protecting groups, also contains a methacrylate monomer, can perform decomposition reaction under the action of acid and heat, and removes ester groups to generate hydrophilic acid groups, so that the material system is changed from oleophylic to hydrophilic, and images can be obtained by developing the material system.
The poly p-hydroxystyrene homopolymer selected by the invention does not contain a protective group after exposure, can participate in a crosslinking reaction, and has alkali solubility and excellent dry etching resistance.
When the weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is less than 1000, the molecular weight is too low to effectively crosslink to form macromolecules insoluble in an alkaline developer; when the weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is higher than 20000, it is difficult to dissolve in a solvent and cannot be used as a photoresist resin.
In some embodiments of the invention, the poly (p-hydroxystyrene) homopolymer has a weight average molecular weight of typically, but not limited to, 1000, 2000, 3000, 4000, 5000, 6000, 7000, 8000, 9000, 10000, 11000, 12000, 13000, 14000, 15000, 16000, 17000, 18000, 19000, or 20000.
Preferably, the photo-deactivator comprises at least one of acetophenone O-benzoyl oxime, nifedipine, 2-nitrophenylmethyl 4-methacryloxypiperidine-1-carboxylate, 1, 2-diisopropyl-3- [ bis (dimethylamino) methylene ] guanidine 2- (3-benzoylphenyl) propionate, and 1, 2-dicyclohexyl-4, 4,5,5 tetramethylbiguanide n-butyltriphenylborate.
Under the irradiation of ultraviolet light, the photoinduced deactivator generates a basic compound to perform a neutralization reaction with the acid catalyst, so that the acid catalyst is deactivated and the cross-linking reaction of the poly-p-hydroxystyrene homopolymer cannot be catalyzed. Therefore, in the ultraviolet light irradiation area, the poly p-hydroxystyrene homopolymer is not crosslinked and cured, and is dissolved in an alkaline developing solution to form a positive image in the non-exposure area, so that the fine pattern processing operation is completed.
In some embodiments of the invention, typical but non-limiting photoinducer deactivators are acetophenone O-benzoyl oxime, nifedipine, 2-nitrophenylmethyl 4-methacryloxypiperidine-1-carboxylate, 1, 2-diisopropyl-3- [ bis (dimethylamino) methylene ] guanidine 2- (3-benzoylphenyl) propionate, or 1, 2-dicyclohexyl-4, 4,5,5 tetramethylbiguanide n-butyltriphenylborate.
Preferably, the composition comprises the following components in parts by mass: 10-60 parts of poly p-hydroxystyrene homopolymer, 2-20 parts of cross-linking agent, 0.2-5 parts of acid catalyst and 0.2-5 parts of photoinduced deactivator.
Preferably, the paint also comprises 5-90 parts of solvent by mass.
In some preferred embodiments of the present invention, the mass fraction of the poly (p-hydroxystyrene) homopolymer is typically, but not limited to, 10 parts, 20 parts, 30 parts, 40 parts, 50 parts, or 60 parts; the mass portion of the crosslinking agent is typically, but not limited to, 2 parts, 5 parts, 10 parts, 15 parts, 18 parts, 19 parts or 20 parts; the mass portion of the acidic catalyst is typically, but not limited to, 0.2 parts, 0.5 parts, 1 part, 2 parts, 3 parts, 4 parts or 5 parts; the mass fraction of photo-deactivator is typically, but not limited to, 0.2 parts, 0.5 parts, 1 part, 2 parts, 3 parts, 4 parts or 5 parts.
Optionally, the cross-linking agent comprises at least one of glycoluril, glycoluril derivatives, 1, 3-bis-methylol urea, 1, 3-dimethyl-2-imidazolidinone.
The structural formula of glycoluril is
In some embodiments of the invention, the crosslinking agent is typically, but not limited to, glycoluril derivatives, 1, 3-bis-methylol urea, or 1, 3-dimethyl-2-imidazolidinone.
Preferably, the acidic catalyst comprises an organic acid and/or an inorganic acid.
In some embodiments of the invention, the acidic catalyst is typically, but not limited to, an organic acid.
In some embodiments of the invention, the acidic catalyst is typically, but not limited to, an inorganic acid.
In some embodiments of the invention, acidic catalysts are typically, but not limited to, organic and inorganic acids.
Preferably, the organic acid comprises at least one of formic acid, acetic acid, propionic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid and p-toluenesulfonic acid.
In some embodiments of the invention, the organic acid is typically, but not limited to, formic acid, acetic acid, propionic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, or p-toluenesulfonic acid.
Preferably, the inorganic acid includes at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and hydrofluoric acid.
In some embodiments of the invention, the inorganic acid is typically, but not limited to, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, or hydrofluoric acid.
Preferably, the solvent comprises an organic solvent.
Preferably, the organic solvent includes at least one of glycol methyl ether, propylene glycol methyl ether acetate, ethyl acetate, and ethyl lactate.
In some embodiments of the invention, the organic solvent is typically, but not limited to, glycol methyl ether, propylene glycol methyl ether acetate, ethyl acetate, or ethyl lactate.
The second aspect of the present invention provides a method for preparing the photoresist composition, which comprises mixing the poly-p-hydroxystyrene homopolymer, the photo-deactivating agent, optionally the cross-linking agent, optionally the acid catalyst and optionally the solvent.
The preparation method of the photoresist composition provided by the invention has the advantages of simple process, large processing capacity, suitability for mass production and low cost.
A third aspect of the invention provides the use of the photoresist composition in the manufacture of integrated circuits.
The application of the photoresist composition provided by the invention in manufacturing integrated circuits improves the production efficiency of the integrated circuits and reduces the production cost.
A fourth aspect of the present invention provides a method of forming a photoresist pattern, the method comprising the steps of:
step A: coating the photoresist composition according to any one of claims 1 to 5 or the photoresist composition prepared by the preparation method according to claim 6 on a target layer to form a photoresist layer;
and B: pre-baking the photoresist layer and then exposing the photoresist layer with actinic radiation to obtain an exposed photoresist layer;
and C: and (4) baking the exposed photoresist layer, adding a developing solution, and developing to obtain the photoresist pattern.
The method for forming the photoresist pattern ensures that the formed pattern meets the actual process requirement and realizes a better photoresist pattern.
Optionally, the pre-baking temperature is 90-110 ℃.
In some embodiments of the invention, the temperature of the pre-bake is typically, but not limited to, 90 ℃, 95 ℃, 100 ℃, 105 ℃ or 110 ℃.
Preferably, the pre-baking time is 30-90 s.
In some embodiments of the invention, the time of the pre-baking is 30s, 40s, 50s, 60s, 70s, 80s or 90 s.
Preferably, the temperature of the intermediate drying is 120-.
In some embodiments of the invention, the temperature of the medium baking is typically, but not limited to, 120 ℃, 125 ℃, 130 ℃, 135 ℃ or 140 ℃.
Preferably, the baking time is 30-90 s.
In some embodiments of the invention, the intermediate baking time is 30s, 40s, 50s, 60s, 70s, 80s, or 90 s.
Optionally, a pre-bake, post-exposure to actinic radiation in step B results in a photoresist layer to be exposed.
Preferably, the film thickness of the photoresist layer to be exposed is 500 nm.
Preferably, the developing solution is added in step C for development.
Preferably, the developer solution comprises a tetramethylammonium hydroxide solution.
In some embodiments of the present invention, the developer solution is typically, but not limited to, a tetramethylammonium hydroxide solution, a potassium hydroxide solution, or a sodium hydroxide solution.
The concentration of the tetramethylammonium hydroxide solution was 2.38 wt%.
Embodiments of the present invention will be described in detail below with reference to examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention.
The specifications and types of the raw materials used in the examples and comparative examples of the present invention are shown in the following table 1, and those who do not indicate specific conditions are performed according to the conventional conditions or conditions suggested by the manufacturer.
TABLE 1 raw material specification and model table
| Components | Model/specification | Manufacturer of the product |
| Poly (p-hydroxystyrene) resin | PHS-6 | Shenzhen Hanya Microelectronics Technology Co.,Ltd. |
| Glycolurils | CAS number 496-46-8 | Aladdin reagent |
| 1, 3-bis (hydroxymethyl) urea | CAS number 140-95-4 | Aladdin reagent |
| Acetic acid | CAS number 64-19-7 | Aladdin reagent |
| Acetophenone O-benzoyl oxime | CAS number 26060-56-0 | Aladdin reagent |
| Propylene glycol methyl ether acetate | CAS number 108-65-6 | Aladdin reagent |
| Ethanesulfonic acid | CAS number 7365-44-8 | Aladdin reagent |
| Sulfuric acid | Analytical purity | Yantai Far East Fine Chemical Co.,Ltd. |
| Propylene glycol methyl ether | CAS number 107-98-2 | Aladdin reagent |
Example 1
This example provides a photoresist composition obtained by uniformly mixing 20g of a polyhydroxystyrene resin having a weight average molecular weight of 10000, 2g of glycoluril, 0.18g of acetic acid, 0.44g of acetophenone O-benzoyl oxime, and 100g of propylene glycol methyl ether acetate, and filtering the mixture through a filter having a pore size of 0.05. mu.m.
Example 2
This example provides a photoresist composition, which is prepared by mixing 20g of polyhydroxystyrene resin with a weight average molecular weight of 10000, 2g of 1, 3-dimethylol urea, 0.2g of ethanesulfonic acid, 0.48g of acetophenone oxime-O-benzoyl and 100g of propylene glycol methyl ether acetate, and filtering the mixture with a filter membrane with a pore size of 0.05 μm.
Example 3
This example provides a photoresist composition obtained by uniformly mixing 20g of a polyhydroxystyrene resin having a weight average molecular weight of 10000, 1.2g of glycoluril, 0.2g of sulfuric acid, 0.5g of acetophenone oxime, and 100g of propylene glycol methyl ether, and filtering the mixture through a filter having a pore size of 0.05. mu.m.
Example 4
This example provides a photoresist composition obtained by uniformly mixing 20g of polyhydroxystyrene resin having a weight average molecular weight of 5000, 1.2g of glycoluril, 0.2g of sulfuric acid, 0.5g of acetophenone oxime-benzoyl and 100g of propylene glycol methyl ether, and filtering the mixture through a filter having a pore size of 0.05. mu.m.
Example 5
This example provides a photoresist composition, which is different from example 1 in that the weight average molecular weight of the poly-p-hydroxystyrene resin is 20000, and other raw materials and preparation methods are the same as example 1 and are not repeated herein.
Comparative example 1
The comparative example provides a photoresist composition, which is a deprotected KrF photoresist product, specifically SUN-KrF100, and StartIke as a manufacturer.
Test example 1
The photoresist compositions provided in examples 1 to 5 and comparative example 1 were spin-coated on the treated silicon wafer, respectively, and Prebaked (PAB) using a hot plate at a prebaking temperature of 100 c for a prebaking time of 60s while adjusting the rotation speed so that the film thickness after drying becomes 500 nm. After exposure by a KrF exposure machine (pattern size 200nm), the resultant was baked in a hot Plate (PEB) at a medium baking temperature of 130 ℃ for 60 seconds. Soaking and developing for 40s by using 2.38 wt% of tetramethylammonium hydroxide solution (TMAH), and cleaning by using deionized water to finish the photoetching process to obtain a positive image. The width of the lines in the resulting positive images was measured separately and the exposure dose was recorded when the line width was 200nm, as reported in table 2.
Test example 2
The silicon wafer substrate obtained in test example 1 was etched by inductively coupled plasma, the etching gas was carbon tetrafluoride, the flow rate was 40ml/min, the ICP power was 280W, the radio frequency power was 50W, the etching pressure was 0.4Pa, and etching was performed for 400s, the film thickness loss of the photoresist and the etching depth of the substrate were measured by a step profiler, the etching ratio was calculated from the film thickness loss/the substrate etching depth, and the results are recorded in table 2.
TABLE 2 lithography Performance data sheet
As can be seen from Table 2, examples 1-5 provided photoresist compositions having a lower exposure dose than the photoresist composition provided in comparative example 1, and had significantly better dry etch resistance than comparative example 1.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. A photoresist composition comprising a poly-p-hydroxystyrene homopolymer and a photo-deactivator;
wherein the mass ratio of the poly-p-hydroxystyrene homopolymer to the photoinduced deactivator is 100-600: 2-50.
2. The photoresist composition of claim 1, wherein the poly-p-hydroxystyrene homopolymer has the formula:
wherein n is an integer greater than 1;
preferably, the weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is 1000-20000.
3. The photoresist composition of claim 1, wherein the photo-deactivating agent comprises at least one of acetophenone O-benzoyl oxime, nifedipine, 2-nitrophenylmethyl 4-methacryloxypiperidine-1-carboxylate, 1, 2-diisopropyl-3- [ bis (dimethylamino) methylene ] guanidine 2- (3-benzoylphenyl) propionate, and 1, 2-dicyclohexyl-4, 4,5,5 tetramethylbiguanide n-butyltriphenylborate.
4. The photoresist composition according to claim 1, comprising the following components in parts by mass: 10-60 parts of poly-p-hydroxystyrene homopolymer, 2-20 parts of cross-linking agent, 0.2-5 parts of acid catalyst and 0.2-5 parts of photoinduced deactivator;
preferably, the paint also comprises 5-90 parts of solvent by mass.
5. The photoresist composition of claim 4, wherein the cross-linking agent comprises at least one of glycoluril, glycoluril derivatives, 1, 3-bis-methylol urea, and 1, 3-dimethyl-2-imidazolidinone;
preferably, the acidic catalyst comprises an organic acid and/or an inorganic acid;
preferably, the organic acid comprises at least one of formic acid, acetic acid, propionic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, and p-toluenesulfonic acid;
preferably, the inorganic acid includes at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and hydrofluoric acid;
preferably, the solvent comprises an organic solvent;
preferably, the organic solvent includes at least one of glycol methyl ether, propylene glycol methyl ether acetate, ethyl acetate, and ethyl lactate.
6. The method for preparing a photoresist composition according to any one of claims 1 to 5, wherein the poly-p-hydroxystyrene homopolymer, the photo-deactivating agent, optionally the cross-linking agent, optionally the acid catalyst, and optionally the solvent are mixed uniformly.
7. Use of a photoresist composition according to any one of claims 1 to 5 or prepared by the method of claim 6 in the manufacture of an integrated circuit.
8. A method of forming a photoresist pattern, the method comprising the steps of:
step A: coating the photoresist composition according to any one of claims 1 to 5 or the photoresist composition prepared by the preparation method according to claim 6 on a target layer to form a photoresist layer;
and B: pre-baking the photoresist layer and then exposing the photoresist layer with actinic radiation to obtain an exposed photoresist layer;
and C: and baking the exposed photoresist layer and developing to obtain the photoresist pattern.
9. The method of forming a photoresist pattern according to claim 8, wherein the temperature of the pre-baking is 90-110 ℃;
preferably, the pre-baking time is 30-90 s;
preferably, the temperature of the intermediate drying is 120-140 ℃;
preferably, the baking time is 30-90 s.
10. The method of forming a photoresist pattern according to claim 8, wherein a photoresist layer to be exposed is obtained before the exposure to actinic radiation after the prebaking in step B;
preferably, the film thickness of the photoresist layer to be exposed is 500 nm;
preferably, a developing solution is added in the step C for development;
preferably, the developer solution comprises a tetramethylammonium hydroxide solution, a potassium hydroxide solution or a sodium hydroxide solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111483647.0A CN114167684A (en) | 2021-12-07 | 2021-12-07 | Photoresist composition, preparation method and application thereof, and method for forming photoresist pattern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111483647.0A CN114167684A (en) | 2021-12-07 | 2021-12-07 | Photoresist composition, preparation method and application thereof, and method for forming photoresist pattern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114167684A true CN114167684A (en) | 2022-03-11 |
Family
ID=80483789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111483647.0A Pending CN114167684A (en) | 2021-12-07 | 2021-12-07 | Photoresist composition, preparation method and application thereof, and method for forming photoresist pattern |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114167684A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103309160A (en) * | 2013-07-03 | 2013-09-18 | 北京科华微电子材料有限公司 | Novel negative chemical amplified photoresist and imaging method thereof |
| CN110501875A (en) * | 2019-08-29 | 2019-11-26 | 合肥鑫晟光电科技有限公司 | Photoetching compositions, production method, substrate and display device |
| CN110998437A (en) * | 2017-02-24 | 2020-04-10 | A·P·G·罗宾森 | Multi-trigger photoresist compositions and methods |
| US20200247739A1 (en) * | 2017-02-23 | 2020-08-06 | Mitsubishi Gas Chemical Company, Inc. | Compound, resin, composition, pattern formation method, and purification method |
| CN112313580A (en) * | 2018-06-18 | 2021-02-02 | 荣昌化学制品株式会社 | Chemically amplified positive resist composition for pattern profile improvement |
-
2021
- 2021-12-07 CN CN202111483647.0A patent/CN114167684A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103309160A (en) * | 2013-07-03 | 2013-09-18 | 北京科华微电子材料有限公司 | Novel negative chemical amplified photoresist and imaging method thereof |
| US20200247739A1 (en) * | 2017-02-23 | 2020-08-06 | Mitsubishi Gas Chemical Company, Inc. | Compound, resin, composition, pattern formation method, and purification method |
| CN110998437A (en) * | 2017-02-24 | 2020-04-10 | A·P·G·罗宾森 | Multi-trigger photoresist compositions and methods |
| CN112313580A (en) * | 2018-06-18 | 2021-02-02 | 荣昌化学制品株式会社 | Chemically amplified positive resist composition for pattern profile improvement |
| CN110501875A (en) * | 2019-08-29 | 2019-11-26 | 合肥鑫晟光电科技有限公司 | Photoetching compositions, production method, substrate and display device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI417682B (en) | Method for producing a miniaturised pattern and treatment liquid for resist substrate using therewith | |
| KR101879173B1 (en) | Composition for forming fine pattern and method for forming fined pattern using same | |
| JP6865794B2 (en) | Composition for semiconductor resist and pattern formation method using it | |
| CN1828414B (en) | Polymer for forming anti-reflective coating | |
| JP2001109165A (en) | Performance forming method | |
| JP2617381B2 (en) | Positive photoresist composition | |
| JP4105106B2 (en) | Fine pattern forming method | |
| CN103988128A (en) | I-line photoresist composition and method for forming fine pattern using the same | |
| CN1074141C (en) | Low metal ions p-cresol oligomers and photosensitive compositions | |
| CN1827659B (en) | Polymer for forming anti-reflective coating | |
| WO2004087773A1 (en) | Auxiliary for forming fine pattern and process for producing the same | |
| KR20130046498A (en) | Self-crosslinking polymer, resist under-layer composition including the same, and method for forming pattern using the same | |
| JP2567984B2 (en) | Positive resist composition | |
| JP5057530B2 (en) | Positive photoresist composition and pattern forming method thereof | |
| JP2006188681A (en) | Organic polymer for forming organic antireflection film | |
| CN1828415B (en) | Polymer for forming anti-reflective coating | |
| JPH1165125A (en) | Pattern forming method | |
| JP3827762B2 (en) | Antireflection composition and resist pattern forming method | |
| CN114167684A (en) | Photoresist composition, preparation method and application thereof, and method for forming photoresist pattern | |
| KR20030035831A (en) | Chemical amplified type positive resist composition for liquid crystal element | |
| JP3135585B2 (en) | Positive photoresist composition containing 2,4-dinitro-1-naphthol | |
| CN111458979B (en) | Photoresist composition, preparation method and application thereof | |
| KR101803098B1 (en) | Positive photoresist composition | |
| CN113960881B (en) | KrF negative photoresist and preparation method and application thereof | |
| KR100363273B1 (en) | Photoresist composition for liquid crystal display circuit board |
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 |