US 12,242,194 B2
Resist underlayer film-forming composition comprising epoxy adduct having long-chain alkyl group
Takafumi Endo, Toyama (JP); Daigo Saito, Toyama (JP); Ryo Karasawa, Toyama (JP); and Rikimaru Sakamoto, Toyama (JP)
Assigned to NISSAN CHEMICAL INDUSTRIES, LTD., Tokyo (JP)
Appl. No. 15/736,262
Filed by NISSAN CHEMICAL INDUSTRIES, LTD., Tokyo (JP)
PCT Filed Jun. 20, 2016, PCT No. PCT/JP2016/068283
§ 371(c)(1), (2) Date Dec. 13, 2017,
PCT Pub. No. WO2017/002653, PCT Pub. Date Jan. 5, 2017.
Claims priority of application No. 2015-133817 (JP), filed on Jul. 2, 2015.
Prior Publication US 2018/0181001 A1, Jun. 28, 2018
Int. Cl. G03F 7/11 (2006.01); C08G 59/18 (2006.01); C09D 5/00 (2006.01); C09D 163/00 (2006.01); G03F 7/004 (2006.01); G03F 7/09 (2006.01); G03F 7/16 (2006.01); G03F 7/20 (2006.01); G03F 7/26 (2006.01); H01L 21/308 (2006.01)
CPC G03F 7/11 (2013.01) [C08G 59/182 (2013.01); C08G 59/184 (2013.01); C08G 59/186 (2013.01); C09D 5/006 (2013.01); C09D 163/00 (2013.01); G03F 7/0045 (2013.01); G03F 7/091 (2013.01); G03F 7/094 (2013.01); G03F 7/16 (2013.01); G03F 7/2002 (2013.01); G03F 7/2037 (2013.01); G03F 7/26 (2013.01); H01L 21/3081 (2013.01); H01L 21/3086 (2013.01)] 8 Claims
 
1. A resist underlayer film-forming composition for covering a stepped substrate comprising
an epoxy adduct (C), and
an acid or an acid generator,
wherein the epoxy adduct (C) is obtained by reacting an epoxy group-containing compound (A) having four epoxy groups with an epoxy adduct-forming compound (B) having an epoxy addition reactive group, wherein one or both of the epoxy group-containing compound (A) and the epoxy adduct-forming compound (B) contain an optionally branched alkyl group having a carbon atom number of three or more,
wherein the epoxy group-containing compound (A) is a compound having a structure of formula (1):

OG Complex Work Unit Chemistry
wherein PA comprises a compound and the

OG Complex Work Unit Chemistry
 of the structure of formula (1) is a unit structure, and wherein PA does not comprise a polymer,
wherein the compound of PA comprises an aliphatic or aromatic hydrocarbon,
wherein the aliphatic or aromatic hydrocarbon optionally comprises an oxygen atom, a nitrogen atom, or a combination thereof,
Ep is a group of formula 1A or 1B:

OG Complex Work Unit Chemistry
wherein a dotted line is a bond,
n1 is 1, n2 and n3 are each an integer of 0 or 1, and n4 is 4,
wherein the epoxy adduct-forming compound (B) is at least one compound selected from the group consisting of carboxylic acid (B1), carboxylic anhydride (B2), a phenol compound (B3), a hydroxyl group-containing compound (B4), a thiol compound (B5), an amino compound (B6), and an imide compound (B7), wherein
the carboxylic acid (B1) is a compound of formula (2):

OG Complex Work Unit Chemistry
wherein R1 is an optionally branched alkyl group having a carbon atom number of 3 to 19, Ar1 is a C6-40 arylene group optionally having a substituent, n5 and n6 are each an integer of 0 or 1, n7 is an integer of 1, and n8 is an integer of 1 or 2,
the carboxylic anhydride (B2) is a compound of formula (3):

OG Complex Work Unit Chemistry
wherein Aa is an acid anhydride group, R2 is an optionally branched alkyl group having a carbon atom number of 3 to 19, Ar2 is a C6-40 arylene group optionally having a substituent, n9 and n10 are each an integer of 0 or 1, and n11 is an integer of 1;
the phenol compound (B3) is a compound of formula (4):

OG Complex Work Unit Chemistry
wherein R3 is an optionally branched alkyl group having a carbon atom number of 3 to 19, Ar3 is a C6-40 arylene group optionally having a substituent, n12 is an integer of 0 or 1, n13 is an integer of 1, n14 is an integer of 1, and n15 is an integer of 1 to 3,
the hydroxyl group-containing compound (B4) is a compound of formula (5):

OG Complex Work Unit Chemistry
wherein R4 is an optionally branched alkyl group having a carbon atom number of 3 to 19, n16 is an integer of 1 to 3, and n17 is an integer of 1,
the thiol compound (B5) is a compound of formula (6):

OG Complex Work Unit Chemistry
wherein R5 is an optionally branched alkyl group having a carbon atom number of 3 to 19, Ar4 is a C6-40 arylene group optionally having a substituent, n18 and n19 are each an integer of 0 or 1, n20 is an integer of 1, and n21 is an integer of 1 to 3,
the amino compound (B6) is a compound of formula (7):

OG Complex Work Unit Chemistry
wherein Ab is a primary amino group, a secondary amino group, or a tertiary amino group, R6 is an optionally branched alkyl group having a carbon atom number of 3 to 19, Ar5 is a C6-40 arylene group optionally having a substituent, n22 and n23 are each an integer of 0 or 1, n24 is an integer of 1, and n25 is an integer of 1 to 3, and
the imide compound (B7) is a compound of formula (8):

OG Complex Work Unit Chemistry
wherein Ac is an imido group having active hydrogen, R7 is an optionally branched alkyl group having a carbon atom number of 3 to 19, Ar6 is a C6-40 arylene group optionally having a substituent, n26 and n27 are each an integer of 0 or 1, n28 is an integer of 1, and n29 is an integer of 1.