IP Library Patent Application 19332356
Patent Application
App. No. 19/332,356

ELECTROACTIVE COMPOUNDS, COMPOSITIONS INCLUDING THE SAME, AND PATTERN FORMATION METHODS

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Patent No.
US None
App. No.
19/332,356
Abstract

A composition including an acid-sensitive polymer comprising a first repeating unit derived from a monomer comprising an acid-decomposable group; a photoacid generator compound; a non-polymeric electron acceptor compound that has a greater electron affinity than an electron affinity of the photoacid generator compound, wherein the non-polymeric electron acceptor compound does not generate a photoacid, and wherein the non-polymeric electron acceptor compound does not comprise a plurality of diazonaphthoquinone (DNQ) groups; and a solvent, wherein the solvent is present in the composition in an amount greater than 50 weight percent, based on total weight of the composition, wherein the composition is a positive-acting EUV photoresist or an electron beam resist.

Claims (59)

1 . A composition, comprising:

an acid-sensitive polymer comprising a first repeating unit derived from a monomer comprising an acid-decomposable group;

a photoacid generator compound;

a non-polymeric electron acceptor compound that has a greater electron affinity than an electron affinity of the photoacid generator compound, wherein the non-polymeric electron acceptor compound does not generate a photoacid, and wherein the non-polymeric electron acceptor compound does not comprise a plurality of diazonaphthoquinone (DNQ) groups; and

a solvent, wherein the solvent is present in the composition in an amount greater than 50 weight percent, based on total weight of the composition,

wherein the composition is a positive-acting EUV photoresist or an electron beam resist.

2 . The composition of claim 1 , comprising two or more photoacid generator compounds, wherein the non-polymeric electron acceptor compound has a greater electron affinity than an electron affinity of each of the two or more photoacid generator compounds.

3 . The composition of claim 1 , further comprising a base-labile material, a base soluble material, or a combination thereof.

4 . The composition of claim 1 , wherein the photoacid generator compound comprises a first anion and the non-polymeric electron acceptor compound comprises a second anion, wherein the first anion and the second anion are structurally the same.

5 . The composition of claim 1 , wherein the acid-sensitive polymer further comprises a second repeating unit, and wherein the second repeating unit comprises a hydroxyaryl group.

6 . The composition of claim 1 , wherein the non-polymeric electron acceptor compound comprises a compound represented by one of Formulae (1) to (5):

wherein, in Formulae (1) to (5),

R 1 to R 25 , R 20a , and R 21a are each independently hydrogen, deuterium, halogen, nitro, amino, cyano, pyridinium, substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 1-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 2-30 heteroaryl, substituted or unsubstituted C 3-30 heteroarylalkyl, or substituted or unsubstituted C 3-30 alkylheteroaryl;

each of R 1 to R 25 , R 20a , and R 21a optionally further comprises one or more divalent linking groups as a part of its structure,

adjacent two or more of R 1 to R 10 optionally form a ring with each other via one or more divalent linking groups, adjacent two or more of R 11 to R 19 optionally form a ring with each other via one or more divalent linking groups, adjacent two or more R 20 optionally form a ring with each other via one or more divalent linking groups, adjacent two or more R 21 optionally form a ring with each other via one or more divalent linking groups, two or more of R 22 to R 25 optionally form a ring with each other via one or more divalent linking groups;

L 1 is a single bond or a divalent linking group;

L 2 is a single bond or a multivalent linking group;

p is an integer from 2 to 6;

n 1 is an integer from 0 to 4;

n 2 is an integer from 0 to 5;

X is a single bond or one or more divalent linking groups; and

A − and B − are each independently an organic anion, wherein A − and B − are optionally joined together to form a divalent organic anion.

7 . The composition of claim 1 , wherein the non-polymeric electron acceptor compound comprises a compound represented by one of Formula (6) to (26):

wherein, in Formula (6) to (26),

R 26 to R 81 are each independently hydrogen, deuterium, halogen, nitro, amino, cyano, pyridinium, substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 1-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 2-30 heteroaryl, substituted or unsubstituted C 3-30 heteroarylalkyl, or substituted or unsubstituted C 3-30 alkylheteroaryl;

each of R 26 to R 81 optionally further comprises one or more divalent linking groups as a part of its structure;

adjacent two or more of R 26 to R 31 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 32 to R 36 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 37 to R 40 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 41 to R 46 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 47 to R 51 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 54 to R 55 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 56 to R 57 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 58 to R 59 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 60 to R 61 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 64 to R 65 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 68 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 70 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 71 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 73 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 74 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 75 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 76 to R 77 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 78 to R 79 optionally form a ring with each other via one or more divalent linking groups; adjacent two or more of R 80 to R 81 optionally form a ring with each other via one or more divalent linking groups;

X − is an organic anion,

n1, n2, and n6 to n9 are each independently an integer from 0 to 4,

n4 and n5 are each independently an integer from 0 to 2,

each l is an integer from 0 to 4;

each k is an integer from 0 to 30;

each p is an integer from 0 to 4;

each q is an integer from 0 to 5;

each r is an integer from 0 to 4;

M is a transition metal; and

X, Y, and Z each independently comprises an electron withdrawing group.

8 . The composition of claim 1 , wherein the non-polymeric electron acceptor compound comprises a compound represented by one of Formulae (27A) to (30A):

wherein, in Formulae (27A) to (30A),

R 82 to R 93 are each independently hydrogen, deuterium, halogen, nitro, amino, cyano, pyridinium, substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 1-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 2-30 heteroaryl, substituted or unsubstituted C 3-30 heteroarylalkyl, or substituted or unsubstituted C 3-30 alkylheteroaryl;

each of R 82 to R 93 optionally further comprises one or more divalent linking groups as a part of its structure;

R 82 and R 83 optionally form a ring with each other via one or more divalent linking groups;

adjacent two or more of R 84 to R 87 optionally form a ring with each other via one or more divalent linking groups;

adjacent two or more of R 88 to R 91 optionally form a ring with each other via one or more divalent linking groups; and

x is 1 or 2.

9 . The composition of claim 1 , comprising two or more of the non-polymeric electron acceptor compounds, wherein the two or more of the non-polymeric electron acceptor compounds have a greater electron affinity than the electron affinity of the photoacid generator compound.

10 . The composition of claim 1 , wherein the photoacid generator compound comprises an onium salt.

11 . The composition of claim 1 , wherein the photoacid generator compound comprises a nonionic compound or a zwitterionic compound.

12 . The composition of claim 1 , wherein the photoacid generator compound is a photoacid generating polymer.

13 . A patterning forming method, comprising:

(a) applying a layer of the composition of claim 1 on a substrate;

(b) soft-baking the composition layer;

(c) exposing the soft-baked composition layer to EUV or electron beam activating radiation;

(d) post-exposure baking the composition layer; and

(e) developing the post-exposure baked composition layer to provide a resist relief image.

14 . The method of claim 13 , wherein the composition comprises two or more photoacid generator compounds, wherein the non-polymeric electron acceptor compound has a greater electron affinity than an electron affinity of each of the two or more photoacid generator compounds.

15 . The method of claim 13 , wherein the composition further comprises a base-labile material, a base soluble material, or a combination thereof.

16 . The method of claim 13 , wherein in the composition, the photoacid generator compound comprises a first anion and the non-polymeric electron acceptor compound comprises a second anion, wherein the first anion and the second anion are structurally the same.

17 . The method of claim 13 , wherein in the composition, the acid-sensitive polymer further comprises a second repeating unit, and wherein the second repeating unit comprises a hydroxyaryl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2026
From: LI, MINGQI; AQAD, EMAD; HERNANDEZ, KENNETH; KANG, DORIS; CUI, LI; LIU, SHENG; TREFONAS III, PETER
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 074238/0893 →