US 7,575,846 B2
Resist polymer and resist composition
Hikaru Momose, Kanagawa (Japan); Atsushi Ootake, Kanagawa (Japan); Akifumi Ueda, Kanagawa (Japan); Tadayuki Fujiwara, Tokyo (Japan); Masaru Takeshita, Kanagawa (Japan); Ryotaro Hayashi, Kanagawa (Japan); and Takeshi Iwai, Kanagawa (Japan)
Assigned to Mitsubishi Rayon Co., Ltd., Tokyo (Japan)
Appl. No. 10/543,914
PCT Filed Jan. 29, 2004, PCT No. PCT/JP2004/000813
§ 371(c)(1), (2), (4) Date Jul. 29, 2005,
PCT Pub. No. WO2004/067592, PCT Pub. Date Aug. 12, 2004.
Claims priority of application No. 2003-024238 (JP), filed on Jan. 31, 2003; application No. 2003-136303 (JP), filed on May 14, 2003; application No. 2003-344750 (JP), filed on Oct. 02, 2003; and application No. 2003-401988 (JP), filed on Dec. 01, 2003.
Prior Publication US 2006/0127801 A1, Jun. 15, 2006
Int. Cl. G03C 1/73 (2006.01); G03F 7/039 (2006.01); C08F 120/70 (2006.01); C08F 24/00 (2006.01)
U.S. Cl. 430—270.1  [430/910; 430/326; 526/297; 526/298; 526/281; 526/282; 526/270] 15 Claims
 
1. A resist polymer, which comprises a constitutional unit represented by formula (1-1) indicated below, a constitutional unit having an acid-dissociable group, and a constitutional unit having a lactone skeleton that is represented by at least one selected from the group consisting of formulas (4-1), (4-2), (4-3), (4-5), (4-6), and (4-10) indicated below:

OG Complex Work Unit Drawing
wherein, in formula (1-1), R01 represents a hydrogen atom or a methyl group; R03 represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms; and each of A01 and A02 independently represents a hydrogen atom, or a linear or branched alkyl group having 1 to 4 carbon atoms, or A01 and A02 together represent —O—, —S—, —NH—, or an alkylene chain having 1 to 6 carbon atoms,

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing
wherein, in formula (4-1), R41 represents a hydrogen atom or a methyl group; each of R401 and R402 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a hydroxy group, a carboxy group, or a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, or R401 and R402 together represent —O—, —S—, —NH—, or a —(CH2)j— chain wherein j represents an integer between 1 and 6; i represents 0 or 1; X5 represents a linear or branched alkyl group having 1 to 6 carbon atoms that may have, as a substituent, at least one selected from the group consisting of a hydroxy group, a carboxy group, an acyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, a cyano group, and an amino group, a hydroxy group, a carboxy group, an acyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, or an amino group; and n5 represents an integer between 0 and 4, and m represents 1 or 2, provided that when n5 is 2 or greater, X5 may be a plurality of different groups,
wherein, in formula (4-2), R42 represents a hydrogen atom or a methyl group; each of R201 and R202 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a hydroxy group, a carboxy group, or a carboxy group esterified with alcohol having 1 to 6 carbon atoms; A1 and A2 together represent —O—, —S—, —NH—, a —(CH2)k— chain wherein k represents an integer between 1 and 6; X6 represents a linear or branched alkyl group having 1 to 6 carbon atoms that may have, as a substituent, at least one selected from the group consisting of a hydroxy group, a carboxy group, an acyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, a cyano group, and an amino group, a hydroxy group, a carboxy group, an acyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, or an amino group; and n6 represents an integer between 0 and 4, provided that when n6 is 2 or greater, X6 may be a plurality of different groups,
wherein, in formula (4-3), R43 represents a hydrogen atom or a methyl group; each of R203 and R204 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a hydroxy group, a carboxy group, or a carboxy group esterified with alcohol having 1 to 6 carbon atoms; each of A3 and A4 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a hydroxy group, a carboxy group, or a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, or A3 and A4 together represent —O—, —S—, —NH—, or a —(CH2)1— chain wherein 1 represents an integer between 1 and 6; X7 represents a linear or branched alkyl group having 1 to 6 carbon atoms that may have, as a substituent, at least one selected from the group consisting of a hydroxy group, a carboxy group, an acyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, a cyano group, and an amino group, a hydroxy group, a carboxy group, an acyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, or an amino group; and n7 represents an integer between 0 and 4, provided that when n7 is 2 or greater, X7 may be a plurality of different groups,
wherein, in formula (4-5), R45 represents a hydrogen atom or a methyl group; each of R8 and R9 independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms; each of R52, R62, and R72 independently represents a hydrogen atom or a methyl group; each of Y12, Y22, and Y32 independently represents —CH2— or —CO—O—, and at least one of them represents —CO—O—; X9 represents a linear or branched alkyl group having 1 to 6 carbon atoms that may have, as a substituent, at least one selected from the group consisting of a hydroxy group, a carboxy group, an acyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, a cyano group, and an amino group, a hydroxy group, a carboxy group, an acyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, or an amino group; and n9 represents an integer between 0 and 4, provided that when n9 is 2 or greater, X9 may be a plurality of different groups,
wherein, in formula (4-6), R46 represents a hydrogen atom or a methyl group; R10 represents a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms; each of R53, R63, and R73 independently represents a hydrogen atom or a methyl group; each of Y13, Y23, and Y33 independently represents —CH2— or —CO—O—, and at least one of them represents —CO—O—; X10 represents a linear or branched alkyl group having 1 to 6 carbon atoms that may have, as a substituent, at least one selected from the group consisting of a hydroxy group, a carboxy group, an acyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, a cyano group, and an amino group, a hydroxy group, a carboxy group, an acyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, or an amino group; and n10 represents an integer between 0 and 4, provided that when n10 is 2 or greater, X10 may be a plurality of different groups, and
wherein, in formula (4-10), each of R91, R92, R93, and R94 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a hydroxy group, a carboxy group, or a carboxy group that is esterified with alcohol having 1 to 6 carbon atoms, or R91 and R92 together represent —O—, —S—, —NH—, or a —(CH2)t— chain wherein t represents an integer between 1 and 6; and m1 represents 1 or 2.