Polymer containing photoacid generator

Patent metadata

Field	Value
Publication number	US-11970557-B2
Application number	US-201916977739-A
Country	US
Kind code	B2
Filing date	Oct 31, 2019
Priority date	Oct 31, 2018
Publication date	Apr 30, 2024
Grant date	Apr 30, 2024

Abstract

A polymer capable of securing pattern uniformity in a photoresist pattern, the polymer containing a photoacid generator by including a structure unit represented by Chemical Formula 1a; and a structure unit represented by Chemical Formula 1b as shown in the specification.

First claim

The invention claimed is:

1. A polymer (A) comprising:
a structure unit represented by Chemical Formula 1a; and
a structure unit represented by Chemical Formula 1c:

wherein, in the Chemical Formulae 1a and 1c,
M1 is an organic cation, and M2 is an organic anion;
L1 and L2 are the same as or different from each other, and each independently any one group selected from the first group consisting of a linear or branched alkylene group; a divalent saturated hydrocarbon ring group; a divalent aromatic hydrocarbon group; a divalent saturated heteroring group; a divalent aromatic heteroring group; a divalent ring group having at least two rings fused, each ring being selected from a saturated hydrocarbon ring, an aromatic hydrocarbon, a saturated heteroring and an aromatic heteroring; —O—; —C(═O)—; —C(═O)O—; —C(═O)N(R19)-; —N(R19)-; —S—; —S(═O)—; —S(═O) 2 —; and —S(═O) 2 O—, or a functional group linking two or more of the groups selected from the first group, and R19 is hydrogen; deuterium; an alkyl group; a saturated hydrocarbon ring group; or an aromatic hydrocarbon group, and two or more R19s are the same as or different from each other;
L1 and L2 are the same as or different from each other, and each independently optionally further substituted with deuterium; a halogen group; a hydroxyl group; an oxo group (═O); or an alkyl group;
n1 is an integer of 0 or greater, and when n1 is 2 or greater, L1s are the same as or different from each other;
n2 is an integer of 0 or greater, and when n2 is 2 or greater, L2s are the same as or different from each other;
Y2, R1, R2 and R3 are each independently any one group selected from the second group consisting of hydrogen; deuterium; a halogen group; a nitrile group; an alkyl group; a saturated hydrocarbon ring group; an aromatic hydrocarbon group; a saturated heteroring group; an aromatic heteroring group; a ring group having at least two rings fused, each ring being selected from a saturated hydrocarbon ring, an aromatic hydrocarbon, a saturated heteroring and an aromatic heteroring; —OR; —OC(═O)R; —C(═O)R; —C(═O)OR; —C(═O)NR 2 ; —NR 2 ; —SR; —S(═O)R; —S(═O) 2 R; and —S(═O) 2 OR, or a functional group linking two or more of the groups selected from the second group, and R is hydrogen; deuterium; an alkyl group; a saturated hydrocarbon ring group; an aromatic hydrocarbon group; a saturated heteroring group; an aromatic heteroring group; or a ring group having at least two or more rings fused, each ring being selected from a saturated hydrocarbon ring, an aromatic hydrocarbon, a saturated heteroring and an aromatic heteroring, two or more Rs being the same as or different from each other; and
R1 to R3 and Y2 are the same as or different from each other and each independently optionally further substituted with deuterium; a halogen group; a hydroxyl group;
an oxo group (═O); or an alkyl group,
R4 and R5 are the same as or different from each other, and each independently have the same definition as R1; and
b1 is 0 or 1, b2 is 0 or 1, and a sum of b1 and b2 is 1.

2. The polymer (A) of claim 1 , wherein M1 is represented by any one functional group represented by Chemical Formulae a-1 to a-3:

in the Chemical Formulae a-1 to a-3,
represents a site linked to L2;
R11 to R14 are the same as or different from each other, and each independently hydrogen; a linear or branched alkyl group; a saturated hydrocarbon ring group; an aromatic hydrocarbon group; a saturated heteroring group; an aromatic heteroring group; or a ring group having two or more rings fused, each ring being selected from a saturated hydrocarbon ring, an aromatic hydrocarbon, a saturated heteroring and an aromatic heteroring,
R11 to R14 being each independently optionally further substituted with deuterium; a halogen group; a hydroxyl group; an alkoxy group; an oxo group (═O); or an alkyl group;
c1 is an integer of 0 or greater, and when c1 is 2 or greater, R13s are the same as or different from each other; and
c2 is an integer of 1 to 10.

3. The polymer (A) of claim 1 , wherein M2-Y2 is represented by Chemical Formula 10:

in the Chemical Formula 10,
R15 and R16 are the same as or different from each other and each independently a halogen group;
a10 is an integer of 1 to 5, and when a10 is 2 or greater, the two or more R15s and R16s are each the same as or different from each other;
L11 and L12 are the same as or different from each other, and each independently any one group selected from the third group consisting of a single bond; a linear or branched alkylene group; a divalent saturated hydrocarbon ring group; a divalent aromatic hydrocarbon group; a divalent saturated heteroring group; a divalent aromatic heteroring group; a divalent ring group having two or more rings fused, each ring selected from a saturated hydrocarbon ring, an aromatic hydrocarbon, a saturated heteroring and an aromatic heteroring; —O—; —C(═O)—; —C(═O)O—; —C(═O)N(R19)-; —N(R19)-; —S—; —S(═O)—; —S(═O) 2 —; and —S(═O) 2 O—, or a group linking two or more of the groups selected from the third group, and R19 is hydrogen; deuterium; an alkyl group; a saturated hydrocarbon ring group; or an aromatic hydrocarbon group, two or more R19s being the same as or different from each other;
R17 is a saturated hydrocarbon ring group; and
L11, L12 and R17 are the same as or different from each other, and each independently optionally further substituted with deuterium; a halogen group; a hydroxyl group; an oxo group (═O); or an alkyl group.

4. The polymer (A) of claim 1 , wherein R3 is represented by Chemical Formula 4:

in the Chemical Formula 4,
R10 is any one group selected from the fourth group consisting of deuterium; a halogen group; a linear or branched alkyl group; a haloalkyl group; a saturated hydrocarbon ring group; an aromatic hydrocarbon group; a saturated heteroring group; an aromatic heteroring group; a ring group having two or more rings fused, each ring being selected from a saturated hydrocarbon ring, an aromatic hydrocarbon, a saturated heteroring and an aromatic heteroring; —OR′; —OC(═O)R′; —C(═O)R′; —C(═O)OR′; —C(═O)NR′ 2 ; —NR′ 2 ; —SR′; —S(═O)R′; —S(═O) 2 R′; and —S(═O) 2 OR′, or a group linking two or more of the groups selected from the fourth group, and R′ is hydrogen; deuterium; an alkyl group; a saturated hydrocarbon ring group; an aromatic hydrocarbon group; a saturated heteroring group; an aromatic heteroring group; or a ring group having at least two rings fused, each ring being selected from a saturated hydrocarbon ring, an aromatic hydrocarbon, a saturated heteroring and an aromatic heteroring, two or more R's being the same as or different from each other, and R10 is optionally further substituted with an oxo group.

5. The polymer (A) of claim 1 , wherein the polymer (A) is a random copolymer comprising the structure unit represented by the Chemical Formula 1a; and the structure unit represented by the Chemical Formula 1c.

6. The polymer (A) of claim 1 , comprising 80 mol % to 99.9 mol % of the structure unit represented by the Chemical Formula 1a based on the total structure units included in the polymer (A).

7. The polymer (A) of claim 1 , comprising 0.1 mol % t

Assignees

• Lg Chemical Ltd

Inventors

• Kim Jihye
• Chun Sung Ho
• Lim Minyoung

Classifications

• C08F232/02 Primary

  having no condensed rings · CPC title

• C08F8/34

  Introducing sulfur atoms or sulfur-containing groups · CPC title

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/0395

  the macromolecular compound having a backbone with alicyclic moieties · CPC title