Photosensitive or radiation-sensitive resin compositions, photosensitive or radiation-sensitive films, pattern forming methods, methods for manufacturing electronic devices, compounds, and resins.

Abstract

Provided is an actinic-ray-sensitive or radiation-sensitive resin composition that, when forming an ultra-fine pattern (for example a line and space pattern of 30 nm or less, a hole pattern with a hole diameter of 30 nm or less, or the like), is superior in terms of roughness performance, and that can suppress the occurrence of defects in a pattern. Said actinic-ray-sensitive or radiation-sensitive resin composition contains: a resin that has a repeating unit derived from a compound represented by general formula (1); and a compound that generates an acid when irradiated with actinic rays or radiation.

Claims

1. (A) A resin having repeating units derived from a compound represented by the following formula (1), or repeating units derived from a compound represented by M-78, M-79, or M-87 below, (B) Compounds that generate acid upon irradiation with active light or radiation, A photosensitive or radiation-sensitive resin composition containing the following: 【Chemistry 1】 In formula (1), A represents a polymerizable group. L represents a divalent linking group having a halogen atom, and the divalent linking group is -COO-, -CO-, -O-, alkylene group, cycloalkylene group, arylene group, or a linking group in which multiple of these are linked. R ３ The symbol represents a halogen atom, amino group, thiol group, or organic group. R ４ This represents a hydrogen atom. n represents an integer greater than or equal to 1. m represents an integer greater than or equal to 0. p represents 0. However, n, m, and p satisfy the relationship n + m ≤ 5 + 2p. If m represents an integer greater than or equal to 2, then multiple R ３ They may be the same or different. If n represents an integer of 2 or greater, there may be multiple R ４ They may be the same or very different. However, L and OR ４ And are in the meta or para position. 【Chemistry 2】

2. The photosensitive or radiation-sensitive resin composition according to claim 1, wherein the compound represented by formula (1) is the compound represented by the following formula (2). 【Transformation 3】 In formula (2), A is the same as A in equation (1) above. L １ The '-' represents -COO-, -CO-, -O-, alkylene group, cycloalkylene group, arylene group, or a divalent linked group formed by linking multiple of these groups. R １ This represents a halogen atom or an organic group containing a halogen atom. R ２ The symbol represents a hydrogen atom, halogen atom, hydroxyl group, amino group, thiol group, or organic group. R ３ 、R ４ 、n, m, and p are each synonymous with R ３ 、R ４ 、n, m, and p in formula (1). However, -L １ -C(R １ ) (Caution ２ ) - and OR ４ And are in the meta or para position.

3. The photosensitive or radiation-sensitive resin composition according to claim 2, wherein the compound represented by formula (2) is the compound represented by the following formula (3). 【Chemistry 4】 In formula (3), X represents a hydrogen atom or an organic group. R １ and R ２ These are, respectively, R in formula (2) above. １ and R ２ It is synonymous with [the above]. L ２ The symbol represents a single bond, or a -COO-, -CO-, -O-, alkylene group, cycloalkylene group, arylene group, or a divalent linked group formed by the linking of multiple such groups. R ３ , R ４ n, m, and p are, respectively, R in formula (1) above. ３ , R ４ It is synonymous with n, m, and p. However, -C(=O)O-L ２ -C(R １ ) (Caution ２ ) - and OR ４ And are in the meta or para position.

4. The photosensitive or radiation-sensitive resin composition according to any one of claims 1 to 3, wherein the compound (B) is an onium salt.

5. The photosensitive or radiation-sensitive resin composition according to any one of claims 1 to 4, wherein the resin (A) further comprises repeating units represented by the following formula (4). 【Transformation 5】 In formula (4), X １１ represents a hydrogen atom, halogen atom, hydroxyl group, or organic group. R １１ Each of these independently represents an alkyl group. １１ They may combine to form a ring.

6. A photosensitive or radiation-sensitive film formed from a photosensitive or radiation-sensitive resin composition according to any one of claims 1 to 5.

7. A step of forming a photosensitive or radiation-sensitive film on a substrate using the photosensitive or radiation-sensitive resin composition described in any one of claims 1 to 5, A step of exposing the aforementioned photosensitive or radiation-sensitive film, A step of developing the exposed light-sensitive or radiation-sensitive film using a developing solution to form a pattern, A pattern forming method having the following characteristics.

8. A method for manufacturing an electronic device, comprising the pattern formation method described in claim 7.

9. A compound represented by the following formula (2), or a compound represented by M-78, M-79, or M-87 below. 【Transformation 6】 In formula (2), A represents a polymerizable group. L １ The '-' represents -COO-, -CO-, -O-, alkylene group, cycloalkylene group, arylene group, or a divalent linked group formed by linking multiple of these groups. R １ This represents a halogen atom or an organic group containing a halogen atom. R ２ The symbol represents a hydrogen atom, halogen atom, hydroxyl group, amino group, thiol group, or organic group. R ３ The symbol represents a halogen atom, amino group, thiol group, or organic group. R ４ This represents a hydrogen atom. n represents an integer greater than or equal to 1. m represents an integer greater than or equal to 0. p represents 0. However, n, m, and p satisfy the relationship n + m ≤ 5 + 2p. If m represents an integer greater than or equal to 2, then multiple R ３ They may be the same or different. If n represents an integer of 2 or greater, there may be multiple R ４ They may be the same or very different. However, -L １ -C(R １ ) (Caution ２ ) - and OR ４ And are in the meta or para position. 【Transformation 7】

10. The compound according to claim 9, wherein the compound represented by formula (2) is the compound represented by the following formula (3). 【Transformation 8】 In formula (3), X represents a hydrogen atom or an organic group. R １ and R ２ These are, respectively, R in formula (2) above. １ and R ２ It is synonymous with [the above]. L ２ The symbol represents a single bond, or a -COO-, -CO-, -O-, alkylene group, cycloalkylene group, arylene group, or a divalent linked group formed by the linking of multiple such groups. R ３ , R ４ n, m, and p are, respectively, R in formula (2) above. ３ , R ４ It is synonymous with n, m, and p. However, -C(=O)O-L ２ -C(R １ ) (Caution ２ ) - and OR ４ And are in the meta or para position.

11. A resin having repeating units derived from the compound described in claim 9 or 10.

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