# US 10,312,074 B2 · Method of producing layer structure, layer structure, and method of forming patterns

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- Number: US 10,312,074 B2
- Document ID: US10312074B2
- Status: Granted
- Kind: B2
- Application number: 14/740,456
- Filed: 2015-06-16
- Published: 2016-05-05
- Granted: 2019-06-04
- Earliest claimed: 2014-10-31
- Assignees: Samsung SDI Co., Ltd.
- Applicants: Samsung SDI Co., Ltd.
- Inventors: Min-Soo Kim; Hyun-Ji Song; Sun-Hae Kang; Sung-Min Kim; Sung-Hwan Kim; Young-Min Kim; Yun-Jun Kim; Hea-Jung Kim; Youn-Hee Nam; Jae-Yeol Baek; Byeri Yoon; Yong-Woon Yoon; Chung-Heon Lee; Seulgi Jeong; Yeon-Hee Jo; Seung-Hee Hong; Sun-Min Hwang; Won-Jong Hwang; Songse Yi; MyeongKoo Kim; Naery Yu
- Web page: https://patentgrep.com/patent/US10312074B2

## CPC

- H10P 14/683: {carbon-based polymeric organic materials, e.g. polyimides, poly cyclobutene or PVC}
- C08G 10/00: Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only
- C08G 12/00: Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen (aminophenols C08G8/16)
- C08G 73/0672: {with only one nitrogen atom in the ring}
- G03F 7/40: Treatment after imagewise removal, e.g. baking
- H10P 14/6342: {Liquid deposition, e.g. spin-coating, sol-gel techniques or spray coating}
- H10P 50/287: {by chemical means}
- H10P 76/405: {characterised by their composition, e.g. multilayer masks}
- H10P 95/08: {Planarisation of organic insulating materials}
- C08G 61/02: Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G 61/122: {derived from five- or six-membered heterocyclic compounds, other than imides}
- C08G 61/124: {with a five-membered ring containing one nitrogen atom in the ring}
- C08G 2261/124: alternating
- C08G 2261/135: Cross-linked structures
- C08G 2261/1422: containing OH groups
- C08G 2261/314: Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/3221: containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
- C08G 2261/3241: containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
- C08G 2261/3424: non-conjugated, e.g. paracyclophanes or xylenes
- C08G 2261/344: containing heteroatoms
- C08G 2261/76: crosslinking
- C08G 2261/90: Applications
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)

## Abstract

A method of producing a layer structure includes forming a first organic layer by applying a first composition including an organic compound on a substrate having a plurality of patterns, applying a solvent on the first organic layer to remove a part of the first organic layer, and applying a second composition including an organic compound on a remaining part of the first organic layer and forming a second organic layer through a curing process.

## Claims

### Claim 1

A method of producing a layer structure that includes a first organic layer and a second organic layer, the method comprising:
forming the first organic layer by applying a first composition including an organic compound on a substrate having a plurality of patterns such that the first organic layer is present inside a gap of the patterns;
applying a solvent on the first organic layer to remove a part of the first organic layer such that a remaining part of the first organic layer is present inside a part of the gap of the patterns; and
applying a second composition including an organic compound on the remaining part of the first organic layer, wherein the second composition is applied by spin-on coating, and forming the second organic layer through a curing process.

### Claim 2 (depends on 1)

The method as claimed in claim 1, wherein the solvent has solubility for the organic compound of the first composition.

### Claim 3 (depends on 1)

The method as claimed in claim 1, wherein the solvent includes γ-butyrolactone, δ-valerolactone, ethyllactate, ethyl-3-ethoxypropionate, propylene glycolmonomethyl ether acetate, β-hydroxyl β-methylbutyrate, methanol, ethanol, 1-propyl alcohol, 2-propyl alcohol, 2-butanol, ethylene glycol, propylene glycol, glycerol, 1,6-hexanediol, cyclo hexanediol, sorbitol, xylitol, 2-methyl-2,4-pentanediol, 1,3-butanediol, 1,4-butanediol, ethylene glycol monomethyl ether, diethylene glycol, dipropylene glycol, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol, poly(ethylene glycol), propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, ethylethoxy propionate, propylene glycol monomethyl ether propionate, ethylene glycol diacetate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, formamide, monomethylformamide, dimethyl formamide, acetamide, monomethylacetamide, dimethyl acetamide, monoethylacetamide, diethylacetamide, N-methylpyrrolidone, methoxy methyl propionate, methoxy ethyl propionate, methoxy propyl propionate, methoxy butyl propionate, ethoxy methyl propionate, ethoxy ethylpropionate, ethoxy propyl propionate, ethoxy butyl propionate, dimethyl sulfone, dimethyl sulfoxide, sulfolane, acetone, acetyl acetone, methylethyl ketone, methyl isobutyl ketone, or a combination thereof.

### Claim 4 (depends on 1)

The method as claimed in claim 1, wherein the solvent is applied in an amount of about 0.1 cc to about 100 cc.

### Claim 5 (depends on 1)

The method as claimed in claim 1, wherein the solvent is applied by spin-on coating, screen printing, slit coating, dipping, inkjet printing, casting, or spray coating.

### Claim 6 (depends on 1)

The method as claimed in claim 1, wherein forming the first organic layer further includes curing the first composition applied on the substrate.

### Claim 7 (depends on 6)

The method as claimed in claim 6, wherein curing after applying the first composition and curing after applying the second composition independently includes applying energy selected from heat, ultraviolet (UV) light, microwaves, sound waves, ultrasonic waves, or a combination thereof.

### Claim 8 (depends on 6)

The method as claimed in claim 6, wherein curing after applying the second composition is performed at a higher temperature than curing after applying the first composition.

### Claim 9 (depends on 8)

The method as claimed in claim 8, wherein:
curing after applying the second composition includes a first curing at about 20 to about 400° C. and a second curing at about 30 to about 500° C., and
the second curing temperature is higher than the first curing temperature.

### Claim 10 (depends on 1)

The method as claimed in claim 1, wherein:
the organic compound of the first composition has a carbon content of about 60 atomic % to about 96 atomic %, and
the organic compound of the second composition has a carbon content of about 60 atomic % to about 96 atomic %.

### Claim 11 (depends on 10)

The method as claimed in claim 10, wherein the organic compound of the first composition and the organic compound of the second composition independently include at least one substituted or unsubstituted aromatic cyclic group, a substituted or unsubstituted aliphatic cyclic group, a substituted or unsubstituted hetero aromatic cyclic group, a substituted or unsubstituted hetero aliphatic cyclic group, or a combination thereof.

### Claim 12 (depends on 10)

The method as claimed in claim 10, wherein the organic compound of the first composition and the organic compound of the second composition independently include an organic polymer, an organic monomer, or a combination thereof.

### Claim 13 (depends on 12)

The method as claimed in claim 12, wherein:
at least one of the organic compound of the first composition and the organic compound of the second composition includes the organic polymer, and
the organic polymer has a weight average molecular weight of about 500 to about 200,000.

### Claim 14 (depends on 12)

The method as claimed in claim 12, wherein:
at least one of the organic compound of the first composition and the organic compound of the second composition includes the organic monomer, and
the organic monomer has a molecular weight of about 50 to about 5,000.

### Claim 15 (depends on 12)

The method as claimed in claim 12, wherein at least one of the first composition and the second composition includes an additive.

### Claim 16 (depends on 15)

The method as claimed in claim 15, wherein:
the first composition includes about 0.001 to 40 parts by weight of the additive based on 100 parts by weight of the first composition, and
the second composition includes about 0.001 to 40 parts by weight of the additive based on 100 parts by weight of the second composition.

### Claim 17 (depends on 15)

The method as claimed in claim 15, wherein the additive includes a surfactant, a plasticizer, a cross-linking agent, a thermal acid generator (TAG), a photoacid generator (PAG), or a combination thereof.

### Claim 18 (depends on 17)

The method as claimed in claim 17, wherein:
the additive includes the cross-linking agent, and
the cross-linking agent includes methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, methoxymethylated thiourea, methoxymethylatedbenzene, butoxymethylatedbenzene, methoxymethylated phenol, butoxymethylated phenol, or a combination thereof.

### Claim 19 (depends on 12)

The method as claimed in claim 12, wherein:
the first composition further includes a first solvent,
the second composition further includes a second solvent, and
the first solvent and the second solvent each independently include propylene glycol, propylene glycol diacetate, methoxy propanediol, diethylene glycol, diethylene glycol butylether, tri(ethylene glycol)monomethylether, propylene glycol monomethylether, propylene glycol monomethylether acetate, cyclohexanone, ethyllactate, gamma-butyrolactone, N,N-dimethyl formamide, N,N-dimethyl acetamide, methylpyrrolidone, methylpyrrolidinone, acetylacetone, ethyl 3-ethoxypropionate, or a combination thereof.

### Claim 20 (depends on 1)

The method as claimed in claim 1, wherein the first organic layer and the second organic layer are hardmask layers.

### Claim 21 (depends on 1)

The method as claimed in claim 1, wherein the first composition and the second composition are independently applied to a thickness of about 300 Å to about 10 μm.

### Claim 22 (depends on 1)

The method as claimed in claim 1, wherein the first composition is applied by spin-on coating, screen printing, slit coating, dipping, inkjet printing, casting, or spray coating.

### Claim 23 (depends on 1)

The method as claimed in claim 1, wherein:
one surface of the substrate includes a first part having a plurality of patterns and a second part having no pattern, and
a sum of steps of the second organic layer is smaller than a sum of steps of the first organic layer.

### Claim 24 (depends on 1)

A layer structure obtained by the method as claimed in claim 1.

### Claim 25 (depends on 1)

A method of forming patterns, the method comprising
providing a layer structure obtained by the method as claimed in claim 1;
forming a silicon-containing thin layer on the layer structure;
forming a photoresist layer on the silicon-containing thin layer;
exposing and developing the photoresist layer to form a photoresist pattern; and
selectively removing the silicon-containing thin layer and the first organic layer, the second organic layer, or a combination thereof in the layer structure using the photoresist pattern.

### Claim 26 (depends on 25)

The method as claimed in claim 25, wherein the method further comprises forming a material layer on the substrate before forming the first organic layer.

### Claim 27 (depends on 26)

The method as claimed in claim 26, wherein the process of selectively removing the silicon-containing thin layer and the first organic layer, the second organic layer, or a combination thereof in the layer structure further includes etching an exposed material layer part.

### Claim 28 (depends on 25)

The method as claimed in claim 25, wherein the method further includes forming a bottom antireflective coating (BARC) before forming the photoresist layer.

### Claim 29 (depends on 25)

The method as claimed in claim 25, wherein the silicon-containing thin layer includes SiCN, SiOC, SiON, SiOCN, SiC, SiN, or a combination thereof.

### Claim 30 (depends on 25)

A semiconductor device produced according to the method of forming patterns as claimed in claim 25.

### Claim 31 (depends on 1)

The method as claimed in claim 1, wherein:
applying the solvent on the first organic layer includes removing a part of the first organic layer from inside the gap of the patterns,
applying the second composition including an organic compound on the remaining part of the first organic layer inside of the gap of the patterns includes applying the second composition inside the gap of the patterns, and
forming the second organic layer includes forming the second organic layer inside the gap of the patterns.