US 12,032,289 B2
Polymer, chemically amplified resist composition and patterning process
Masahiro Fukushima, Joetsu (JP); Masayoshi Sagehashi, Joetsu (JP); and Emiko Ono, Joetsu (JP)
Assigned to Shin-Etsu Chemical Co., Ltd., Tokyo (JP)
Filed by Shin-Etsu Chemical Co., Ltd., Tokyo (JP)
Filed on Sep. 16, 2020, as Appl. No. 17/022,368.
Claims priority of application No. 2019-175739 (JP), filed on Sep. 26, 2019.
Prior Publication US 2021/0096465 A1, Apr. 1, 2021
Int. Cl. G03F 7/038 (2006.01); C08F 212/14 (2006.01); C08F 220/28 (2006.01); C08F 220/40 (2006.01); C09D 125/18 (2006.01); C09D 133/08 (2006.01); C09D 133/14 (2006.01); G03F 7/039 (2006.01)
CPC G03F 7/0388 (2013.01) [C08F 212/24 (2020.02); C08F 220/283 (2020.02); C08F 220/40 (2013.01); C09D 125/18 (2013.01); C09D 133/08 (2013.01); C09D 133/14 (2013.01); G03F 7/039 (2013.01)] 10 Claims
 
1. A resist composition comprising a polymer consisting of recurring units having an acid labile group containing a multiple bond, recurring units having a phenolic hydroxyl group, recurring units adapted to generate an acid upon exposure, and recurring units having the formula (d1) or (d2),
wherein the recurring units having an acid labile group containing a multiple bond have the formula (a):

OG Complex Work Unit Chemistry
wherein RA is each independently hydrogen, fluorine, methyl or trifluoromethyl,
X1 is a single bond, phenylene group, naphthylene group or (backbone)-C(═O)—O—X11—, X11 is a C1-C10 aliphatic hydrocarbylene group which may contain a hydroxyl moiety, ether bond, ester bond or lactone ring, or a phenylene or naphthylene group,
AL1 is an acid labile group having the formula (a1) or (a2):

OG Complex Work Unit Chemistry
wherein R1 to R8 are each independently hydrogen or a C1-C20 hydrocarbyl group which may contain a heteroatom, with the proviso that not both R1 and R2 are hydrogen at the same time and not both R6 and R7 are hydrogen at the same time, a pair of R1 and R2, R1 and R3, R3 and R4, R4 and R5, R6 and R7, or R6 and R8 may bond together to form an aliphatic ring with the carbon atom(s) to which they are attached or the carbon atoms to which they are attached and the intervening carbon atom,
wherein the recurring units adapted to generate an acid upon exposure have the formula (c1), (c2) or (c3):

OG Complex Work Unit Chemistry
wherein RA is each independently hydrogen, fluorine, methyl or trifluoromethyl,
Z1 is a single bond or phenylene group,
Z2 is a single bond, —C(═O)—O—Z21—, —C(═O)—NH—Z21— or —O—Z21—, —Z21 is a C1-C6 aliphatic hydrocarbylene group, phenylene group or a divalent group obtained from combination thereof, which may contain a carbonyl moiety, ester bond, ether bond or hydroxyl moiety,
Z3 is a single bond, phenylene, naphthylene, or (backbone)-C(═O)—O—Z31—, Z31 is a C1-C10 aliphatic hydrocarbylene group which may contain a hydroxyl moiety, ether bond, ester bond or lactone ring, or phenylene or naphthylene group,
Z4 is a single bond or —Z41—C(═O)—O—, Z41 is a C1-C20 hydrocarbylene group which may contain a heteroatom,
Z5 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, —C(═O)—O—Z51—, —C(═O)—NH—Z51— or —O—Z51—, Z51 is a C1-C6 aliphatic hydrocarbylene group or phenylene group, which may contain a carbonyl moiety, ester bond, ether bond or hydroxyl moiety,
R21 and R22 are each independently a C1-C20 hydrocarbyl group which may contain a heteroatom, R21 and R22 may bond together to form a ring with the sulfur atom to which they are attached,
L1 is a single bond, ether bond, ester bond, carbonyl group, sulfonic acid ester bond, carbonate bond or carbamate bond,
Rf1 and Rf2 are each independently fluorine or a C1-C6 fluoroalkyl group,
Rf3 and Rf4 are each independently hydrogen, fluorine or a C1-C6 fluoroalkyl group,
M− is a non-nucleophilic counter ion,
A+ is an onium cation, and
k is an integer of 0 to 3,
wherein A+ is a cation having the formula (c4) or (c5):

OG Complex Work Unit Chemistry
wherein R31, R32 and R33 are each independently a C1-C20 hydrocarbyl group which may contain a heteroatom, R31 and R32 may bond together to form a ring with the sulfur atom to which they are attached, R34 and R35 are each independently a C1-C20 hydrocarbyl group which may contain a heteroatom,

OG Complex Work Unit Chemistry
wherein RA is each independently hydrogen, fluorine, methyl or trifluoromethyl,
X1 is a single bond, phenylene group, naphthylene group or (backbone)-C(═O)—O—X11—, X11 is a C1-C10 aliphatic hydrocarbylene group which may contain a hydroxyl moiety, ether bond, ester bond or lactone ring, or a phenylene or naphthylene group,
Y1 is a single bond or (backbone)-C(═O)—O—,
AL2 and AL3 are each independently an acid labile group free of multiple bond,
R41 is halogen, cyano, a C1-C20 hydrocarbyl group which may contain a heteroatom, C1-C20 hydrocarbyloxy group which may contain a heteroatom, C2-C20 hydrocarbylcarbonyl group which may contain a heteroatom, C2-C20 hydrocarbylcarbonyloxy group which may contain a heteroatom, or C2-C20 hydrocarbyloxycarbonyl group which may contain a heteroatom, and
p is an integer of 0 to 4.