Photoresist developer and method of developing photoresist

Patent metadata

Field	Value
Publication number	US-12487527-B2
Application number	US-202418631832-A
Country	US
Kind code	B2
Filing date	Apr 10, 2024
Priority date	Nov 13, 2017
Publication date	Dec 2, 2025
Grant date	Dec 2, 2025

Abstract

A photoresist developer includes a solvent having Hansen solubility parameters of 15<δ d <25, 10<δ p <25, and 6<δ p <30; an acid having an acid dissociation constant, pKa, of −15<pKa<4, or a base having a pKa of 40>pKa>9.5; and a chelate.

First claim

What is claimed is:

1 . A method of manufacturing a semiconductor device, comprising:
forming a resist layer on a substrate; crosslinking one or more regions of the resist layer by selectively exposing the resist to actinic radiation; and removing the one or more regions of the resist regions that were crosslinked by applying a liquid composition to the resist layer, wherein the liquid composition comprises: a solvent having Hansen solubility parameters of 15<δ d <25, 10<δ p <25, and 6<δ h <30; an acid selected from the group consisting of ethanedioic acid, methanoic acid, 2-hydroxypropanoic acid, 2-hydroxybutanedioic acid, citric acid, uric acid, trifluoromethanesulfonic acid, benzenesulfonic acid, ethanesulfonic acid, methanesulfonic acid, oxalic acid, maleic acid, carbonic acid, oxoethanoic acid, 2-hydroxyethanoic acid, propanedioic acid, butanedioic acid, 3-oxobutanoic acid, hydroxylamine-o-sulfonic acid, formamidinesulfinic acid, methylsulfamic acid, sulfoacetic acid, 1,1,2,2-tetrafluoroethanesulfonic acid, 1,3-propanedisulfonic acid, nonafluorobutane-1-sulfonic acid, 5-sulfosalicylic acid, nitric acid, sulfuric acid, hydrochloric acid, and combinations thereof; and a chelate selected from a group consisting of ethylenediamine-N,N′-disuccinic acid (EDDS), diethylenetriaminepentaacetic acid (DTPA), polyaspartic acid, trans-1,2-cyclohexanediamine-N,N,N′,N′-tetraacetic acid monohydrate, and combinations thereof.

2 . The method according to claim 1 , wherein a concentration of the chelate is 0.001 wt. % to 20 wt. % based on a total weight of the liquid composition.

3 . The method according to claim 1 , wherein a concentration of the solvent is from about 60 wt. % to about 99 wt. % based on a total weight of the liquid composition.

4 . The method according to claim 1 , wherein a concentration of the acid is from about 0.001 wt. % to about 20 wt. % based on a total weight of the liquid composition.

5 . The method according to claim 1 , wherein the liquid composition is at a temperature of about 25° C. to about 75° C. when it is applied to the resist layer.

6 . A method of manufacturing a semiconductor device, comprising:
forming a layer to be patterned over a substrate; forming a photoresist layer over the layer to be patterned; selectively exposing the photoresist layer to actinic radiation to form exposed regions of the photoresist layer thereby crosslinking the photoresist layer in the exposed regions; applying a developer to the selectively exposed photoresist layer to remove the exposed regions of the photoresist layer and expose regions of the layer to be patterned, wherein the developer comprises:
a first solvent comprising at least one from the group consisting of dimethyl sulfoxide, acetone, ethylene glycol, methanol, ethanol, propanol, propanediol, water, 4-methyl-2-pentanone, hydrogen peroxide, isopropanol, and butyldiglycol;
an acid having an acid dissociation constant, pKa, of −15<pKa<4, or a base having a pKa of 40>pKa>9.5; and
a chelate selected from a group consisting of ethylenediamine-N,N′-disuccinic acid (EDDS), diethylenetriaminepentaacetic acid (DTPA), polyaspartic acid, trans-1,2-cyclohexanediamine-N,N,N′,N′-tetraacetic acid monohydrate, and combinations thereof; and
etching exposed regions of the layer to be patterned.

7 . The method according to claim 6 , wherein the layer to be patterned is a metallization layer or a dielectric layer.

8 . The method according to claim 6 , wherein a concentration of the chelate is 0.001 wt. % to 20 wt. % based on a total weight of the developer.

9 . The method according to claim 6 , wherein a concentration of the first solvent is from about 60 wt. % to about 99 wt. % based on a total weight of the developer.

10 . The method according to claim 6 , wherein a concentration of the acid is from about 0.001 wt. % to about 20 wt. % based on a total weight of the developer.

11 . The method according to claim 6 , wherein the developer is at a temperature of about 25° C. to about 75° C. when it is applied to the photoresist layer.

12 . A composition, comprising:
a first solvent having Hansen solubility parameters of 15<δ d <25, 10<δ p <25, and 6<δ h <30; an acid selected from the group consisting of ethanedioic acid, 2-hydroxypropanoic acid, 2-hydroxybutanedioic acid, uric acid, trifluoromethanesulfonic acid, ethanesulfonic acid, methanesulfonic acid, oxalic acid, maleic acid, carbonic acid, oxoethanoic acid, 2-hydroxyethanoic acid, propanedioic acid, butanedioic acid, 3-oxobutanoic acid, hydroxylamine-o-sulfonic acid, formamidinesulfinic acid, methylsulfamic acid, sulfoacetic acid, 1,1,2,2-tetrafluoroethanesulfonic acid, 1,3-propanedisulfonic acid, nonafluorobutane-1-sulfonic acid, 5-sulfosalicylic acid, and combinations thereof; and a chelate selected from a group consisting of ethylenediamine-N,N′-disuccinic acid (EDDS), diethylenetriaminepentaacetic acid (DTPA), polyaspartic acid, trans-1,2-cyclohexanediamine-N,N,N′,N′-tetraacetic acid monohydrate, and combinations thereof.

13 . The composition of claim 12 , wherein a concentration of the chelate is 0.001 wt. % to 20 wt. % based on a total weight of the composition.

14 . The composition of claim 12 , wherein a concentration of the first solvent is from about 60 wt. % to about 99 wt. % based on a total weight of the composition.

15 . The composition of claim 12 , wherein a concentration of the acid is from about 0.001 wt. % to about 20 wt. % based on a total weight of the composition.

16 . The composition of claim 12 , further comprising a surfactant selected from the group consisting of sodium stearate, 4-(5-dodecyl) benzenesulfonate, ammonium lauryl sulfate, sodium lauryl sulfate, sodium laureth sulfate, sodium myreth sulfate, dioctyl sodium sulfosuccinate, perfluorooctanesulfonate, perfluorobutanesulfonate, alkyl-aryl ether phosphate, alkyl ether phosphates, sodium lauroyl sarcosinate, perfluoronononanoate, perfluorooctanoate, octenidine dihydrochloride, cetrimonium bromide, cetylpyridinium chloride, benzalkonium chloride, benzethonium chloride, dimethyldioctadecylammonium chloride, dioctadecyldimethylammonium bromide, 3-[(3-cholamidopropyl) dimethylammonio]-1-propanesulfonate, cocamidopropyl hydroxysultaine, cocamidopropyl betaine, phospholipidsphosphatidylserine, phosphatidylethanolamine, phosphatidylcholine, sphingomyelins, octaethylene glycol monodecyl ether, pentaethylene glycol monodecyl ether, polyethoxylated tallow amine, cocamide monoethanolamine, cocamide diethanolamine, glycerol monostearate, glycerol monolaurate, sorbitan monolaurate, sorbitan monostearate, sorbitan tristearate, and combinations thereof.

17 . The composition of claim 16 , wherein a concentration of the surfactant is from 0.001 wt. % to 1 wt. % based on a total weight of the composition.

18 . The composition of claim 12 , further comprising a second solvent different from the first solvent, wherein the second solvent is selected from the group consisting of water, hexane, heptane, octane, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, trichloroethylene, critical carbon dioxide, methanol, ethanol, propanol, butanol, diethyl ether, dipropyl ether, dibutyl ether, ethyl vinyl ether, dioxane, propylene oxide, tetrahydrofuran, cellosolve, methyl cellosolve, butyl cellosolve, methyl carbitol, diethylene glycol monoethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, pyridine, formamide, and N,N-dimethyl formamide.

Assignees

• Taiwan Semiconductor Mfg Co Ltd

Inventors

• Zi An-Ren
• Lin Chin-Hsiang
• Chang Ching-Yu
• Cheng Yahru

Classifications

• H10P76/204

  of organic photoresist masks · CPC title

• H10P14/68

  Organic materials, e.g. photoresists · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title

• G03F7/0382

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title

• G03F7/32

  Liquid compositions therefor, e.g. developers · CPC title