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CN-122011922-A - Bottom anti-reflection coating composition and preparation and application thereof

CN122011922ACN 122011922 ACN122011922 ACN 122011922ACN-122011922-A

Abstract

The invention provides a bottom anti-reflection coating composition, and preparation and application thereof. The bottom anti-reflection coating composition comprises a polyorthoester resin containing phenolic hydroxyl groups, wherein the structure of the polyorthoester resin containing phenolic hydroxyl groups is shown as a formula I. The bottom antireflective coating composition of the invention has high photosensitivity, low development residue, excellent antireflective properties and good process compatibility. Formula I.

Inventors

  • JI CHANGWEI
  • ZHANG AIQIANG
  • CHEN RENZHI
  • YE JIANFENG
  • WU JIALONG
  • JIANG YIMIN

Assignees

  • 嘉庚创新实验室
  • 闽晨星电子材料(厦门)有限公司

Dates

Publication Date
20260512
Application Date
20260409

Claims (13)

  1. 1. A bottom antireflective coating composition comprising a phenolic hydroxyl group-containing polyorthoester resin having the structure of formula I: A formula I; Wherein at least one of R 1 、R 2 comprises a phenolic hydroxyl structure-containing group comprising at least one of a phenolic hydroxyl structure-containing C 6~24 aryl, C 7~40 aralkyl, C 7~40 alkaryl, fluorenyl, a polyphenyl structure linked by a bridge; n is an integer of 10 to 500; Wherein the sum p of the number of moles p 1 of R 1 including the group having a phenolic hydroxyl group structure and the number of moles p 2 of R 2 including the group having a phenolic hydroxyl group structure, calculated as the total number of moles of R 1 and R 2 , is 10% m≤p≤70% m.
  2. 2. The bottom antireflective coating composition of claim 1, wherein at least one of R 1 、R 2 comprises a group that does not contain a phenolic hydroxyl structure; Wherein the group free of phenolic hydroxyl structure comprises at least one of C 1-10 alkyl, C 3-10 cycloalkyl and C 1-10 ether.
  3. 3. The bottom antireflective coating composition of claim 1, wherein said phenolic hydroxyl group containing moiety is selected from one or more of the following: , , , , , , , , , , , , , , , , , , 。
  4. 4. the bottom antireflective coating composition according to claim 2, wherein said groups free of phenolic hydroxyl structures are selected from one or more of the following: , , , , 。
  5. 5. The bottom antireflective coating composition according to claim 1, wherein the polyorthoester resin comprising phenolic hydroxyl groups has a Mw of 500 to 30000g/mol, and/or The PDI of the polyorthoester resin containing phenolic hydroxyl groups is 1.5-5.
  6. 6. The bottom antireflective coating composition of claim 5, wherein said polyorthoester resin comprising phenolic hydroxyl groups has a Mw of 1000 to 10000g/mol, and/or The PDI of the polyorthoester resin containing phenolic hydroxyl groups is 1.9-3.5.
  7. 7. The bottom antireflective coating composition of claim 1, further comprising at least one of a crosslinker, photoacid generator, other additives, solvents; wherein the other additive is at least one selected from leveling agent and quenching agent.
  8. 8. The bottom antireflective coating composition of claim 7, wherein said bottom antireflective coating composition comprises, in parts by weight: 1-10 parts of polyorthoester resin containing phenolic hydroxyl groups; 0.05-5 parts of cross-linking agent; 0.01-2 parts of photoacid generator; 0.0001-0.1 part of other additives, and 85-98 Parts of solvent.
  9. 9. The bottom antireflective coating composition according to claim 7, wherein said crosslinking agent is a polyfunctional vinyl ether compound, and/or The photoacid generator is an ionic photoacid generator and/or a nonionic photoacid generator, and/or The solvent is at least one selected from ketone solvents, ester solvents, ether solvents and aromatic hydrocarbon solvents.
  10. 10. The bottom antireflective coating composition according to claim 9, wherein said crosslinking agent is selected from at least one of ethylene glycol divinyl ether, 1, 4-butanediol divinyl ether, 1, 6-hexanediol divinyl ether, triethylene glycol divinyl ether, cyclohexanedimethanol divinyl ether, and/or The photoacid generator is selected from diphenyliodonium triflate, diphenyliodonium camphorsulfonate, diphenyliodonium perfluoro-1-butanesulfonate, diphenyliodonium perfluorooctanesulfonate, 4-methoxyphenyl iodonium trifluoromethane sulfonate, bis (4-tert-butylphenyl) iodonium tetrafluoroborate, bis (4-tert-butylphenyl) iodonium hexafluorophosphate, bis (4-tert-butylphenyl) iodonium trifluoromethane sulfonate, bis (4-tert-butylphenyl) iodonium perfluoro-1-butanesulfonate, bis (4-tert-butylphenyl) iodonium camphorsulfonate, bis (4-tert-butylphenyl) iodonium perfluorooctanesulfonate, triphenylsulfonium hexafluorophosphate, 4-methoxyphenyl iodonium triflate p-tolyl diphenylsulfonium triflate salt 4-Methoxyphenyl iodonium trifluoromethane sulfonate, p-tolyldiphenylsulfonium trifluoromethane sulfonate, and p-toluyldiphenyl sulfonium perfluorooctane sulfonate p-tolyldiphenylsulfonium perfluoro-1-butanesulfonate, p-tolyldiphenylsulfonium camphorsulfonate, 2,4, 6-trimethylphenyldiphenylsulfonium trifluoromethanesulfonate, 4-tert-butylphenyldiphenylsulfonium trifluoromethanesulfonate, 4-phenylphenylthiodiphenylsulfonium hexafluorophosphate, 1- (2-naphthaloylmethyl) thiolonium trifluoromethanesulfonate, 4-hydroxy-1-naphthyldimethylbenzylsulfonium trifluoromethanesulfonate, 2-methyl-4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2,4, 6-tris (trichloromethyl) -1,3, 5-triazine, 2-phenyl-4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2- (4-chlorophenyl) -4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2- (4-methoxyphenyl) -4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2- (4-methoxy-1-naphthyl) -4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2- (benzo [ d ] [1,3] dioxol-5-yl) -4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2- (4-methoxystyryl) -4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2- (3, 4, 5-trimethoxystyryl) -4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2- (3, 4-dimethoxystyryl) -4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2- (2-methoxystyryl) -4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2- (4-Ding Yangben vinyl) -4, 6-bis (trichloromethyl) -1,3, 5-triazine, 2- (4-pentoxystyryl) -4, 6-bis (trichloromethyl) -1,3, 5-triazine, diphenyldisulfone, di-p-tolyldisulfone, bis (phenylsulfonyl) diazomethane, bis (4-chlorophenylsulfonyl) diazomethane, bis (p-tolylsulfonyl) diazomethane, bis (4-t-butylphenylsulfonyl) diazomethane, bis (2, 4-xylylsulfonyl) diazomethane, bis (cyclohexylsulfonyl) diazomethane, (benzoyl) (phenylsulfonyl) diazomethane, 1-benzoyl-1-phenylmethyl p-toluenesulfonate, 2-benzoyl-2-hydroxy-2-phenylethyl p-toluenesulfonate, 1,2, 3-benzenetriyl trimethyl trimethsulfonate, 2, 6-dinitrophenyl methyl p-toluenesulfonate, 2-nitrobenzyl p-toluenesulfonate, 4-nitrobenzyl p-toluenesulfonate, N- (phenylsulfonyloxy) succinimide, N- (trifluoromethylsulfonyloxy) succinimide, N- (perfluoro-1-butanesulfonic acid) succinimide, N- (perfluorooctanesulfonic acid) succinimide, N- (perfluoro-1-butanesulfonic acid) phthalimide, N- (trifluoromethylsulfonyloxy) phthalimide, N- (perfluorooctanesulfonic acid) phthalimide, At least one of N- (trifluoromethylsulfonyloxy) -5-norbornene-2, 3-dicarboxyimide, N- (perfluoro-1-butanesulfonic acid) -5-norbornene-2, 3-dicarboxyimide, N- (perfluorooctanesulfonic acid) -5-norbornene-2, 3-dicarboxyimide, N- (trifluoromethylsulfonyloxy) naphthylmethylene, N- (perfluoro-1-butanesulfonic acid) naphthylmethylene, N- (perfluorooctanesulfonic acid) naphthylmethylene, N- (10-camphorsulfonyloxy) naphthylmethylene, and/or The leveling agent is at least one selected from acrylic leveling agent, organic silicon leveling agent and fluorocarbon leveling agent, and/or The quencher is amine compound and/or photobase generator, and/or The solvent is at least one selected from propylene glycol methyl ether acetate, propylene glycol monoacetate, ethylene glycol methyl ether acetate, ethylene glycol diacetate, propylene glycol methyl ether, propylene glycol monoethyl ether, ethylene glycol methyl ether diacetate, butyl acetate, neopentyl acetate, ethyl lactate, methyl ethyl ketone, methyl isobutyl ketone, gamma-butyrolactone, dioxane, N-dimethylformamide, N-dimethylacetamide and dimethyl sulfoxide.
  11. 11. A method of manufacturing a semiconductor, comprising: A lithographic image formed using the bottom antireflective coating composition of any one of claims 1 to 10 developed in an alkaline aqueous developer.
  12. 12. The method of claim 11, wherein the aqueous base developer is selected from the group consisting of tetramethyl ammonium hydroxide (TMAH), potassium hydroxide, and sodium hydroxide in water.
  13. 13. A semiconductor device, characterized in that it is manufactured using the method of claim 11 or 12.

Description

Bottom anti-reflection coating composition and preparation and application thereof Technical Field The invention belongs to the photoetching technology in the field of microelectronic manufacturing, and particularly relates to a Bottom Anti-reflective coating (BARC) composition used in a photoetching process, in particular to a photodegradable Bottom Anti-reflective coating composition which can be developed by an alkaline aqueous solution after exposure, and preparation and application thereof. Background Along with the continuous shrinkage of the feature size of integrated circuits, the wavelength of the exposure light source is also shortened (e.g. KrF, arF), and the reflected light on the high refractive index substrate (e.g. silicon, polysilicon, metal) interferes with the incident light, resulting in standing wave effect and wobble effect in the photoresist, which seriously affects the pattern resolution and the control accuracy of Critical Dimension (CD). To suppress this reflection, a bottom antireflective coating (BARC) is typically applied between the photoresist and the substrate. Conventional BARC materials are mostly crosslinked organic polymers, which need to be removed after development by an additional dry etching (e.g. plasma etching) step. This increases process complexity, cost and time. In addition, dry etching may cause damage to the underlying substrate and may cause pattern distortion due to etch selectivity problems. To simplify the process, a developable BARC has been developed. Such BARCs can be removed along with the photoresist in the exposed areas during the photoresist development step without the need for a separate dry etch. The developable BARCs of the prior art are based on acid-catalyzed chemical amplification reactions, for example, systems of hydroxyl-containing resins with acid-labile crosslinkers such as melamine resins. After acid production by exposure, the acid catalyzes the cleavage of the cross-links during Post Exposure Bake (PEB), which causes the exposed areas to change from insoluble to soluble. However, such systems have some inherent drawbacks: 1. The photosensitivity is insufficient and a higher exposure dose is required to generate enough acid to completely break the crosslinked network. 2. Development residues-since the polymer backbone itself is not broken, dissociation of the crosslinking sites alone may not be sufficient to completely dissolve the macromolecular chains, and "scum" (Scum) which is difficult to remove is easily formed on the substrate surface, resulting in defects. 3. The process window is narrow, PEB temperature and time have obvious influence on the decrosslinking reaction, and the improper control is easy to cause pattern defects. Accordingly, there is a strong need in the art to develop a new developable BARC that has high photosensitivity and can be thoroughly removed after development without leaving any residue. Disclosure of Invention The invention aims to overcome the defects of the prior art and provide a novel alkali water developable bottom anti-reflection coating composition. The composition utilizes the unique acid-catalyzed degradation characteristics of polyorthoester polymers to achieve high sensitivity "chemical bond cleavage" imaging, rather than conventional "de-crosslinking" imaging, thereby ensuring development residue-free. A new generation of lithographic pattern modifying materials is provided for advanced semiconductor manufacturing. In order to achieve the above purpose, the invention adopts the following technical scheme: in a first aspect, the present invention provides a bottom antireflective coating composition comprising a polyorthoester resin comprising phenolic hydroxyl groups, the polyorthoester resin comprising phenolic hydroxyl groups having the structure shown in formula I: I is a kind of Wherein at least one of R 1、R2 comprises a phenolic hydroxyl structure-containing group comprising at least one of a phenolic hydroxyl structure-containing C 6~24 aryl, C 7~40 aralkyl, C 7~40 alkaryl, fluorenyl, a polyphenyl structure linked by a bridge; n is an integer of 10 to 500; Wherein the sum p of the number of moles p 1 of R 1 including the group having a phenolic hydroxyl group structure and the number of moles p 2 of R 2 including the group having a phenolic hydroxyl group structure, calculated as the total number of moles of R 1 and R 2, is 10% m≤p≤70% m. According to the bottom antireflective coating composition of the first aspect, at least one of R 1、R2 comprises a group that does not contain a phenolic hydroxyl structure; Wherein the group free of phenolic hydroxyl structure comprises at least one of C 1-10 alkyl, C 3-10 cycloalkyl and C 1-10 ether. The bottom antireflective coating composition according to the first aspect, the phenolic hydroxyl structure containing group is selected from one or more of the following: ,,,,,,,,,,,,,,,,,,。 the bottom antireflective coating composition according to the