US 12,242,195 B2
Method for manufacturing cured film and use of the same
Takashi Sekito, Kakegawa (JP); Shigemasa Nakasugi, Yamato (JP); Hiroshi Yanagita, Kakegawa (JP); and Taku Hirayama, Kakegawa (JP)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Appl. No. 17/605,852
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Apr. 24, 2020, PCT No. PCT/EP2020/061460
§ 371(c)(1), (2) Date Oct. 22, 2021,
PCT Pub. No. WO2020/216899, PCT Pub. Date Oct. 29, 2020.
Claims priority of application No. 2019-085991 (JP), filed on Apr. 26, 2019; and application No. 2019-186781 (JP), filed on Oct. 10, 2019.
Prior Publication US 2022/0221794 A1, Jul. 14, 2022
Int. Cl. G03F 7/11 (2006.01); C08G 61/10 (2006.01); C09D 165/00 (2006.01); G03F 7/09 (2006.01)
CPC G03F 7/11 (2013.01) [C08G 61/10 (2013.01); C09D 165/00 (2013.01); G03F 7/094 (2013.01); C08G 2261/124 (2013.01); C08G 2261/1424 (2013.01); C08G 2261/18 (2013.01); C08G 2261/228 (2013.01); C08G 2261/312 (2013.01); C08G 2261/3142 (2013.01)] 13 Claims
 
1. A method for manufacturing a resist layer above a cured film comprising:
(1) applying a composition (i) above a substrate;
(2) forming a hydrocarbon-containing film from the composition (i); and
(3) irradiating the hydrocarbon-containing film with plasma, electron beam and/or ion to form a cured film,
provided that the composition (i) comprises a hydrocarbon-containing compound (A) and a solvent (B); and
the hydrocarbon-containing compound (A) comprises a structural unit (A1-1) represented by the following formula (A1-1):

OG Complex Work Unit Chemistry
wherein,
Ar21 is a C6-50 aromatic hydrocarbon group;
R21 is a C6-50 aromatic hydrocarbon group, hydrogen, or a single bond bonded to another structural unit;
n21 is 0;
wherein R22 and R23 are not present;
wherein a single bond connects the two phenyl rings;
where, Ar21, and R21 contain no fused aromatic ring;
R12 is I, Br or CN; p11 is a number of 0 to 5, p12 is a number of 0 to 1, q11 is 0, r11 is a number of 0 to 5, s11 is a number of 0 to 5; and
p11, q11 and r11 do not become 0 simultaneously in one structural unit;
where, the intensity ratio of G band and D band R=ID/IG in Raman spectroscopy (measured with laser wavelength of 514.5 nm) of the cured film formed in the process (3) is 0.35 to 0.90;
wherein the hydrocarbon-containing compound (A) is a polymer comprising an aldehyde derivative when the polymer is synthesized from 0 to 30 mol % based on the sum of all components used in the synthesis;
wherein the process (3) comprises the following conditions:
in the case of plasma irradiation:
the atmosphere is N2, NF3, H2, fluorocarbon, rare gas, or a mixture of any of these; and/or
the RF discharge power is 1,000 to 10,000 W,
in the case of electron beam irradiation:
the acceleration voltage is 2 to 200 kV, and/or
the irradiation amount is 100 to 5,000 kGy,
in the case of ion irradiation:
the elemental species of the ion to be irradiated is hydrogen, boron, carbon, nitrogen, rare gas, or a mixture of any of these;
the acceleration voltage is 3 to 1000 kV; and/or
the irradiation amount is 1013 to 1018 ion/cm2.