Acetal-based compound, acetal-based prepolymer, acetal-based polymer, and photoresist composition comprising the same

Patent metadata

Field	Value
Publication number	US-12503433-B2
Application number	US-202218055959-A
Country	US
Kind code	B2
Filing date	Nov 16, 2022
Priority date	Dec 6, 2021
Publication date	Dec 23, 2025
Grant date	Dec 23, 2025

Abstract

An acetal-based compound represented by Formula 1, an acetal-based prepolymer, an acetal-based polymer, and a photoresist composition including the samewherein in Formula 1, R1 to R10, G, a, and b are as defined in the detailed description, and * indicates a linking site.

First claim

What is claimed is:

1 . An acetal-based prepolymer which is a polymerization product of the acetal-based compound, a first polymerizable monomer having a polar group, and a second polymerizable monomer having an acid labile group,
wherein the acetal-based compound is represented by Formula 1:

wherein, in Formula 1,
R 1 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C8-C60 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted C1-C60 monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —P(═S)(Q 1 )(Q 2 ),
Q 1 to Q 3 are each independently hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group unsubstituted or substituted with deuterium, —F, cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C1-C60 heterocyclic group unsubstituted or substituted with deuterium, —F, cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C7-C60 arylalkyl group unsubstituted or substituted with deuterium, —F, cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; or a C2-C60 heteroarylalkyl group unsubstituted or substituted with deuterium, —F, cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof,
with an exception that both R 1 and R 2 are hydrogen (in other words, neither R 1 nor R 2 are both hydrogen),
a and b are each independently 0 or an integer of 1 to 10,
G is a group represented by Formula 2 or Formula 2a,

wherein, in Formula 2 and Formula 2a, R 4 is an unsubstituted or substituted C1-C60 alkyl group or an unsubstituted or substituted C1-C60 aryl group,
R 3 and R 5 to R 8 are each independently hydrogen, or an unsubstituted or substituted C1-C20 alkyl group,
* indicates a linking site, and
k is 0 or 1.

2 . The acetal-based prepolymer of claim 1 , wherein the first polymerizable monomer having a polar group is a compound represented by Formula 4:

wherein, in Formula 4, R 11 to R 13 are each independently a hydrogen, a C1-30 alkyl group, or a C6-C60 aryl group,
R 14 to R 18 are each independently hydrogen, a C1-C60 alkyl group, a C1-C60 alkoxy group, a cyano group, a hydroxyl group, a halogen, a halogen-substituted C1-C60 alkyl group, an acetal group, R′C(═O)O—, wherein R′ is H or a C1-C20 alkyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C8-C60 monovalent non-aromatic condensed polycyclic group, or a C1-C60 monovalent non-aromatic condensed heteropolycyclic group,
optionally, at least two adjacent R 14 to R 18 are linked to form a ring, and
at least one of R 14 to R 18 is a polar group.

3 . The acetal-based prepolymer of claim 2 , wherein the polar group is a hydroxyl group, an acetal group, or R′C(═O)O—, wherein R′ is H or a C1-C20 alkyl group.

4 . The acetal-based prepolymer of claim 1 , wherein the second polymerizable monomer having an acid labile group is a compound represented by Formula 5:

wherein, in Formula 5, R 21 , R 22 , and R 23 are each independently a hydrogen or a C1-C60 alkyl group, and
R 24 is an acid labile group.

5 . The acetal-based prepolymer of claim 4 , wherein the acid labile group is a tertbutyl group, a tert-amyl group, or a hydrocarbon group having a C4-C60 alicyclic structure.

6 . The acetal-based prepolymer of claim 4 , wherein the acid labile group is an unsubstituted or substituted group A selected from an adamantyl group, a noradamantyl group, a decalin residue, a tricyclodecanyl group, a tetracyclododecanyl group, a norbornyl group, a cedrol group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecanyl group, or a cyclododecanyl group.

7 . The acetal-based prepolymer of claim 1 , wherein the acetal-based prepolymer is a compound represented by Formula 6:

wherein, in Formula 6, A 1 and A 2 are each independently H, or —C(═O)R 3 , where R 3 is a C1-C60 alkyl group,
Z 1 and Z 2 are each independently —SH,

and * indicates a binding site,
R is a C1-C30 alkyl group, R 2 is a C1-C30 alkyl group, a and b are each independently 0 or an integer of 1 to 10, R 11 , R 12 , and R 13 are each independently hydrogen, a C1-30 alkyl group or a C6-C60 aryl group, R 21 , R 22 , and R 23 are each independently hydrogen or a C1-C60 alkyl group, and a1, b1, a2, and b2 are each independently an integer from 1 to 10,000.

8 . The acetal-based prepolymer of claim 1 , wherein the acetal-based prepolymer is an acetal-based prepolymer represented by Formula 6-1:

wherein, in Formula 6-1, A1 and A2 are each independently H or —C(═O)R 3 , wherein R 3 is a C1-C60 alkyl group,
Z 1 and Z 2 are each independently —SH,

and * indicates a binding site,
R is a C1-C30 alkyl group, and a1, b1, a2, and b2 indicate the degrees of polymerization and are each independently a number from 1 to 10,000.

9 . The acetal-based prepolymer of claim 1 , wherein the acetal-based prepolymer is a compound represented by Formula 6-2, a compound represented by Formula 6-3, or a compound represented by Formula 6-4:

wherein, in Formulae 6-2, 6-3, and 6-4, a1, b1, a2, and b2 are each independently a number from 1 to 10,000.

10 . The acetal-based prepolymer of claim 1 , wherein the acetal-based prepolymer has a weight average molecular weight of about 1,500 grams per mole to about 20,000 grams per mole.

11 . An acetal-based polymer which is a chain extension reaction product of the acetal-based prepolymer of claim 5 and

Assignees

• Samsung Electronics Co Ltd
• Inha Ind Partnership Inst

Inventors

• Ahn Chanjae
• Kim Myungwoong
• Kwak Yoonhyun
• An Sol

Classifications

• C08G75/14

  Polysulfides · CPC title

• C08G18/6225

  Polymers of esters of acrylic or methacrylic acid · CPC title

• C08G18/3206

  aliphatic · CPC title

• C08G18/73

  acyclic · CPC title

• C08G18/246

  containing also tin-carbon bonds · CPC title