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CN-118812400-B - Non-chemical amplification type polyphenyl substituted adamantane derivative single-molecule resin photoresist and preparation method and application thereof

CN118812400BCN 118812400 BCN118812400 BCN 118812400BCN-118812400-B

Abstract

The invention discloses a polyphenyl substituted adamantane derivative single-molecule resin shown in a formula IA, and a preparation method and application thereof. The polyphenyl substituted adamantane derivative single-molecule resin has good solubility in various polar solvents, is suitable for being made into films, has high decomposition temperature, and can well meet the requirements of photoetching technology.

Inventors

  • CHEN JINPING
  • WANG ZHIHAO
  • LI YI
  • ZENG YI
  • YU TIANJUN

Assignees

  • 中国科学院理化技术研究所

Dates

Publication Date
20260512
Application Date
20230421

Claims (10)

  1. 1. A compound of formula IA: IA Wherein R 1 ,R 2 ,R 3 ,R 4 are identical or different and are selected independently of one another from H or ; Ra is selected from H, OH, -OS (O) 2 -C n ,C n is selected from C 1-12 alkyl, halo C 1-12 alkyl, -C 6-20 aryl-Rb, -5-20 membered heteroaryl-Rb, rb is selected from halogen, C 1-12 alkyl, C 1-12 alkoxy or halo C 1-12 alkyl; m is 1,2,3,4 or 5; Provided that at least 2 of R 1 ,R 2 ,R 3 ,R 4 are selected from And (2) and At least 1 Ra is-OS (O) 2 -C n .
  2. 2. The compound of claim 1, wherein Ra is selected from H, OH, -OS (O) 2 -C n ,C n is selected from C 1-6 alkyl, halogenated C 1-6 alkyl, -C 6-12 aryl-Rb, -5-12 membered heteroaryl-Rb, rb is selected from halogen, C 1-6 alkyl, C 1-6 alkoxy or halogenated C 1-6 alkyl; m is 1,2,3,4 or 5; And is also provided with At least 2 of which are-OS (O) 2 -C n .
  3. 3. The compound of claim 2, wherein formula IA is selected from the structures of formula I, formula II, or formula III: in formula I, formula II or formula III, ra are the same or different and each independently represents a hydrogen atom, a hydroxyl group or-OS (O) 2 -C n , provided that each 1 At least 1 of the plurality of Ra substituents of (C) are-OS (O) 2 -C n and C n is selected from C 1-6 alkyl, halo C 1-6 alkyl, -C 6-12 aryl-Rb, -5-12 membered heteroaryl-Rb, rb being selected from halo, C 1-6 alkyl, C 1-6 alkoxy or halo C 1-6 alkyl.
  4. 4. A compound according to any one of claims 1 to 3, wherein each 1 A kind of electronic device Wherein 1 Ra substituent is-OS (O) 2 -C n , and the others are H; or 2 Ra substituents are-OS (O) 2 -C n , the others being H; or three are all-OS (O) 2 -C n and C n is selected from the group consisting of C 1-3 alkyl, halogenated C 1-3 alkyl, -C 6-12 aryl-C 1-3 alkyl, -5-12 membered heteroaryl-C 1-3 alkyl.
  5. 5. A compound according to any one of claims 1-3, wherein the compound is selected from the group consisting of: 。
  6. 6. A photoresist composition comprising a compound of any one of claims 1-5.
  7. 7. The photoresist composition of claim 6, wherein the photoresist composition is a positive or negative photoresist composition comprising a compound of formula IA and a photoresist solvent.
  8. 8. The photoresist composition of claim 6 or 7, wherein the photoresist composition comprises, in mass percent: the compound according to any one of claim 1 to 5, 90-99Wt% of photoresist solvent.
  9. 9. The photoresist composition of claim 8, wherein the photoresist solvent is selected from one or more of methyl isobutyl ketone, propylene glycol monomethyl ether acetate, ethyl lactate, acetonitrile, acetone, ethylene glycol monomethyl ether, and cyclohexanone.
  10. 10. Use of the photoresist composition of any one of claims 6 to 9 in 248nm lithography, 254nm lithography, 193nm lithography, extreme ultraviolet lithography or electron beam lithography.

Description

Non-chemical amplification type polyphenyl substituted adamantane derivative single-molecule resin photoresist and preparation method and application thereof Technical Field The invention belongs to the technical field of materials, and in particular relates to a polyphenyl substituted adamantane derivative single-molecule resin and non-chemical amplification type photoresist composition. Background Photoresist, also called photoresist, is a kind of corrosion-resistant film material with solubility changed after being irradiated by ultraviolet light, electron beam or ion beam, and is widely used in micro-processing of integrated circuits and semiconductor discrete devices. The photoresist is a key material in the device micromachining technology because the photoresist is coated on the surface of a semiconductor, a conductor or an insulator, the part left after exposure and development protects the bottom layer, and then the required micropattern can be transferred from the mask plate to the substrate to be processed by etching with an etchant. With the rapid development of the semiconductor industry, the requirements for the resolution of photolithography technology are also increasing. While the resolution of photolithography is closely related to the properties of the photoresist material, in addition to the lithographic apparatus. High performance photoresists can achieve higher resolution. Conventional photoresists are usually chemically amplified photoresists and mainly comprise acid-sensitive polymer main materials, acid generators, additives and the like. The problems of uneven distribution of each component, acid diffusion, post baking delay and the like are also caused by the characteristics of multiple components and chemical amplification, although the sensitivity is high. In contrast, non-chemically amplified resists are typically composed of only a light-sensitive host material, with a direct solubility shift occurring before and after exposure, thereby avoiding these problems with chemically amplified resists. Non-chemically amplified photoresists also typically exhibit higher resolution and small line edge roughness. In addition, the traditional photoresist main body material adopts polymer resin with molecular weight of 5000-15000 daltons, and the polymer resin generally affects the resolution and edge roughness of the photoetching pattern due to the reasons of too large molecular volume, polydisperse molecular weight, winding of molecular chains and the like, so that the high-resolution photoetching requirement cannot be met. Therefore, it is desirable to provide a non-chemically amplified single-molecule resin with a molecular size as small as possible, and a photoresist material with good film forming properties and thermal stability, to meet the requirements of high resolution lithography. Disclosure of Invention An object of the present invention is to provide a polyphenyl substituted adamantane derivative single molecule resin. It is another object of the present invention to provide a photoresist composition comprising the polyphenyl substituted adamantane derivative single molecule resin. In order to achieve the above purpose, the invention adopts the following technical scheme: a compound of formula IA: Wherein R 1,R2,R3,R4 are identical or different and are selected independently of one another from H or Ra is selected from H, OH, -OS (O) 2-Cn,Cn is selected from C 1-12 alkyl, halo C 1-12 alkyl, -C 6-20 aryl-Rb, -5-20 membered heteroaryl-Rb, rb is selected from nitro, cyano, halo, C 1-12 alkyl, C 1-12 alkoxy or halo C 1-12 alkyl; m is 1,2,3,4 or 5; Provided that at least 1 of R 1,R2,R3,R4 is selected from And is also provided withAt least 1 Ra is-OS (O) 2-Cn. According to an embodiment of the invention, ra is selected from H, OH, -OS (O) 2-Cn,Cn is selected from C 1-6 alkyl, halogenated C 1-6 alkyl, -C 6-12 aryl-Rb, -5-12 membered heteroaryl-Rb, rb is selected from nitro, cyano, halogen, C 1-6 alkyl, C 1-6 alkoxy or halogenated C 1-6 alkyl; m is 1,2,3,4 or 5; And is also provided with At least 2 of which are-OS (O) 2-Cn. According to some specific embodiments of the invention, formula IA is selected from the structures shown in formula I, formula II or formula III: in formula I, formula II or formula III, ra are the same or different and each independently represents a hydrogen atom, a hydroxyl group or-OS (O) 2-Cn, provided that each 1 At least 1 of the plurality of Ra substituents of (C) is-OS (O) 2-Cn and C n is selected from C 1-6 alkyl, halo C 1-6 alkyl, -C 6-12 aryl-Rb, -5-12 membered heteroaryl-Rb, rb being selected from nitro, cyano, halo, C 1-6 alkyl, C 1-6 alkoxy or halo C 1-6 alkyl. In some specific embodiments, every 1A kind of electronic deviceIn which 1Ra substituent is-OS (O) 2-Cn and the others are H, or 2 Ra substituents are-OS (O) 2-Cn and the others are H, or three are-OS (O) 2-Cn and C n is selected from C 1-3 alkyl, halogenated C 1-3 alkyl (e.g., perfluoro sub