Cyclic compound, process for production of the cyclic compound, radiation-sensitive composition, and method for formation of resist pattern
A cyclic compound represented by formula (1): wherein L, R 1 , R′, and m are as defined in the specification. The cyclic compound of formula (1) is highly soluble to a safety solvent, highly sensitive, and capable of forming resist patterns with good profile. Therefore, the cyclic compound is useful as a component of a radiation-sensitive composition.
1. A cyclic compound represented by formula (1):
wherein each L is independently a single bond or a divalent organic group selected from the group consisting of a linear or branched alkylene group having 1 to 20 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, an arylene group having 6 to 24 carbon atoms, —O—, —OC(═O)—, —OC(═O)—O—, —N(R 5 )—C(═O)— wherein R 5 is hydrogen or an alkyl group having 1 to 10 carbon atoms, —N(R 5 )—C(═O)O— wherein R 5 is as defined above, —S—, —SO—, —SO 2 —, and a combination of any of preceding groups;
each R 1 is independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, cyano group, nitro group, hydroxyl group, a heterocyclic group, a halogen, carboxyl group, glycidyl group, an alkylsilyl group having 1 to 20 carbon atoms, or hydrogen atom, with the proviso that at least one of R 1 is glycidyl group and another at least one of R 1 is hydrogen atom;
each R′ is independently an aryl group represented by the following formula:
wherein R 4 is a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, cyano group, nitro group, a heterocyclic group, carboxyl group, hydroxyl group, glycidyl group, or an alkylsilyl group having 1 to 20 carbon atoms, and p is an integer of 1 to 5; and
each m is an integer of 1 to 4.
2. The cyclic compound according to claim 1 , represented by formula (2):
wherein R 1 , R 4 , p, and m are as defined above, X 2 is a hydrogen or halogen atom, m 5 is an integer of 0 to 3, and m+m 5 =4.
3. The cyclic compound according to claim 1 , having a molecular weight of 800 to 5000.
4. A method of producing the cyclic compound according to claim 1 , which comprises subjecting at least one aldehyde compound (A1) and at least one phenol compound (A2) to condensation reaction, to obtain a cyclic compound (A); and subjecting the cyclic compound (A) and at least one epihalohydrin (A3) to dehydrohalogenation reaction.
5. The method according to claim 4 , wherein the aldehyde compound (A1) has 1 to 4 formyl groups and 2 to 59 carbon atoms, and the phenol compound (A2) has 1 to 3 phenolic hydroxyl groups and 6 to 15 carbon atoms.
6. The method according to claim 4 , wherein the cyclic compound (A) has a molecular weight of 700 to 5000.
7. The method according to claim 4 , wherein by the dehydrohalogenation reaction between the cyclic compound (A) and the at least one epihalohydrin (A3), at least one phenolic hydroxyl group of the cyclic compound (A) is converted to glycidyloxy group while maintaining another at least one phenolic hydroxyl group unchanged.
8. A radiation-sensitive composition comprising the cyclic compound according to claim 1 and a solvent.
9. The radiation-sensitive composition according to claim 8 , comprising 1 to 80% by weight of a solid component and 20 to 99% by weight of a solvent.
10. The radiation-sensitive composition according to claim 9 , wherein a content of the cyclic compound is 50 to 99.999% by weight of a total weight of the solid component.
11. The radiation-sensitive composition according to claim 8 , further comprising an acid generator (C) which directly or indirectly generates acid upon exposure to any radiation selected from the group consisting of visible light, ultraviolet ray, excimer laser, electron beam, extreme ultraviolet ray (EUV), X-ray, and ion beam.
12. The radiation-sensitive composition according to claim 8 , further comprising an acid crosslinking agent (G).
13. The radiation-sensitive composition according to claim 8 , further comprising an acid-diffusion controller (E).
14. The radiation-sensitive composition according to claim 8 , wherein the cyclic compound is represented by formula (2):
wherein R 1 , R 4 , p, and m are as defined above, X 2 is a hydrogen or halogen atom, m 5 is an integer of 0 to 3, and m+m 5 =4.
15. The radiation-sensitive composition according to claim 8 , wherein the cyclic compound is selected from the group consisting of compounds represented by formulae (6-5) to (6-8):
wherein R 12 is glycidyl group or hydrogen atom, with the proviso that at least one R 12 is glycidyl group and another at least one of R 12 is hydrogen atom.
16. The radiation-sensitive composition according to claim 9 , wherein the solid component comprises 50 to 99.4% by weight of the cyclic compound, 0.001 to 49% by weight of the acid generator (C), 0.5 to 49% by weight of the acid crosslinking agent (G), 0.001 to 49% by weight of the acid-diffusion controller (E), and 0 to 49% by weight of an optional component (F), each based on the solid component.
17. The radiation-sensitive composition according to claim 8 , capable of forming an amorphous film by spin coating.
18. The radiation-sensitive composition according to claim 17 , wherein a dissolving speed of the amorphous film into a 2.38% by weight aqueous solution of tetramethylammonium hydroxide at 23° C. is 10 Å/s or more.
19. A method of forming resist pattern, which comprises a step of coating the radiation-sensitive composition according to claim 8 on a substrate, thereby forming a resist film; a step of exposing the resist film to radiation; and a step of developing the exposed resist film.
20. A resist material comprising the compound of claim 1 .