KR101821735B1 - Organic layer composition, organic layer, and method of forming patterns - Google Patents

Organic layer composition, organic layer, and method of forming patterns Download PDF

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KR101821735B1
KR101821735B1 KR1020150039217A KR20150039217A KR101821735B1 KR 101821735 B1 KR101821735 B1 KR 101821735B1 KR 1020150039217 A KR1020150039217 A KR 1020150039217A KR 20150039217 A KR20150039217 A KR 20150039217A KR 101821735 B1 KR101821735 B1 KR 101821735B1
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KR20160112847A (en
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권효영
김승현
남궁란
남연희
도미니아 라뜨웰
문수현
정현일
허유미
송현지
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삼성에스디아이 주식회사
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • 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
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • 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
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement

Abstract

A first polymer comprising a moiety represented by formula (1), a second polymer comprising a moiety represented by formula (2), and an organic film composition comprising a solvent, an organic film prepared from the organic film composition, And a method for forming a pattern using the same.
The definitions of the above formulas (1) and (2) are as described in the specification.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic film composition, an organic film, and a method of forming a pattern,

An organic film composition, an organic film prepared using the organic film composition, and a pattern forming method using the organic film composition.

BACKGROUND ART [0002] In recent years, the semiconductor industry has developed into an ultrafine technology having a pattern of a few to a few nanometers in a pattern of a size of several hundred nanometers. Effective lithographic techniques are essential to realize this ultrafine technology.

A typical lithographic technique involves forming a material layer on a semiconductor substrate, coating a photoresist layer thereon, exposing and developing the photoresist layer to form a photoresist pattern, and etching the material layer using the photoresist pattern as a mask do.

In recent years, as the size of a pattern to be formed decreases, it is difficult to form a fine pattern having a good profile only by the typical lithographic technique described above. Accordingly, a fine pattern can be formed by forming an organic film called a hardmask layer between the material layer to be etched and the photoresist layer.

The hard mask layer acts as an interlayer to transfer the fine pattern of the photoresist to the material layer through the selective etching process. Therefore, the hard mask layer needs to have heat resistance and resistance to erosion resistance so as to withstand the multiple etching process.

Meanwhile, it has recently been proposed that the hard mask layer is formed by a spin-on coating method instead of the chemical vapor deposition method. The spin-on coating method is not only easy to process but also can improve gap-fill and planarization properties. In order to realize a fine pattern, it is necessary to form multiple patterns. In this case, the embedding characteristic of embedding the pattern in the film without voids is required. Further, in the case where there is a step on the substrate to be processed, or in the case where a pattern dense portion and an area having no pattern exist together on the wafer, it is necessary to planarize the film surface by the underlayer film.

There is a demand for an organic film material which can satisfy the properties required for the hard mask layer described above.

One embodiment provides an organic film composition capable of not only improving film density and corrosion resistance but also ensuring excellent solubility.

Other embodiments provide organic films with excellent mechanical and planarization properties.

Another embodiment provides a method of forming a pattern using the organic film composition.

According to one embodiment, there is provided an organic film composition comprising a first polymer comprising a moiety represented by the following formula (1), a second polymer comprising a moiety represented by the following formula (2), and a solvent.

[Chemical Formula 1]

Figure 112015027780420-pat00001

In Formula 1,

A 1 and A 2 each independently represent a divalent group derived from any one of the compounds listed in Group 1 below,

A 3 and A 4 are each independently a ring group containing at least one substituted or unsubstituted benzene ring,

m is 0 or 1;

[Group 1]

Figure 112015027780420-pat00002

In the group 1,

R 1 , R 2 And R 3 is each independently selected from the group consisting of hydrogen, a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group,

Z 1 to Z 6 each independently represent a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group , A substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, or a combination thereof,

a, b, c, d, e and f are each independently an integer of 0 to 2;

(2)

Figure 112015027780420-pat00003

In Formula 2,

B 1 and B 2 are each independently a ring group containing at least one substituted or unsubstituted benzene ring,

B 3 and B 4 are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof,

n is 0 or 1;

In the above formulas (1) and (2), "*"

In Formula 1, A 3 and A 4 each independently may be any of the groups listed in Group 2 below.

[Group 2]

Figure 112015027780420-pat00004

In the group 2,

X 1 and X 2 are each independently a substituted or unsubstituted C6 to C50 arylene group, A substituted or unsubstituted C1 to C10 alkylene oxide-containing group, or a combination thereof,

Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C30 aryl group,

Z 7 to Z 10 each independently represent a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group , A substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, or a combination thereof,

g, h, i and j are each independently an integer of 0 to 2,

k is an integer of 1 to 3,

"*" Is the connection point.

In the group 2, X 1 and X 2 are each independently a substituted or unsubstituted C6 to C50 arylene group, and the C6 to C50 arylene group may be a divalent group derived from any one of the compounds listed in Group 3 below .

[Group 3]

Figure 112015027780420-pat00005

In the group 2, Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, and the C6 to C30 aryl group may be a monovalent group derived from any one of the compounds listed in the group 3.

In the group 1, R 1 , R 2 And R 3 may be each independently hydrogen, or a substituted or unsubstituted phenyl group.

In Formula 2, B 1 and B 2 each independently represent a cyclic group including at least two substituted or unsubstituted benzene rings, and the cyclic group including at least two benzene rings may be a group selected from the group consisting of the compounds listed in Group 4 Or a bivalent group derived from any one of them.

[Group 4]

Figure 112015027780420-pat00006

In Formula 2, B 3 and B 4 may each independently be selected from the following Group 5.

[Group 5]

Figure 112015027780420-pat00007

In the group 5,

R 11 And R 22 are each independently selected from the group consisting of a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,

a1 and a2 each independently represent an integer of 0 to 2,

L x is -O-, -S-, -S = O-, -SO 2 -, -NH-, -C = O-, -CH 2 -, - (CH 3) 2 C-, - (CF 3 ) 2 C-, or a combination thereof,

* Is the connection point.

The first polymer may be represented by any one of the following formulas (1-1) to (1-4).

[Formula 1-1]

Figure 112015027780420-pat00008

[Formula 1-2]

Figure 112015027780420-pat00009

[Formula 1-3]

Figure 112015027780420-pat00010

[Formula 1-4]

Figure 112015027780420-pat00011

In the above Formulas 1-1 to 1-4,

Each R 4 is independently hydrogen, a hydroxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

Z 11 To Z 17 are each independently a hydroxy group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkyl alkenyl group, a substituted or unsubstituted C1 to C20 alkyl A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Or a substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, or a combination thereof,

k, l, m, n, o, p, and q are each independently an integer of 0 to 2,

n 0 is an integer from 2 to 300,

* Is the connection point.

The second polymer may be represented by any one of the following formulas (2-1) to (2-4).

[Formula 2-1]

Figure 112015027780420-pat00012

[Formula 2-2]

Figure 112015027780420-pat00013

[Formula 2-3]

Figure 112015027780420-pat00014

[Chemical Formula 2-4]

Figure 112015027780420-pat00015

In the above Formulas (2-1) to (2-4)

R 33 To R 66 are each independently a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,

a3 to a6 each independently represent an integer of 0 to 2,

n 1 is an integer of 2 to 300,

* Is the connection point.

The weight average molecular weight of the first polymer and the weight average molecular weight of the second polymer may each independently be 500 to 200,000.

The first polymer and the second polymer may be contained in the organic film composition in a weight ratio of 97: 3 to 3:97.

The first polymer and the second polymer may be contained in the organic film composition in a weight ratio of 9: 1 to 1: 9.

The first polymer and the second polymer may be contained in an amount of 0.1 wt% to 50 wt% based on the total amount of the organic film composition.

According to another embodiment, there is provided an organic film in which the above-mentioned organic film composition is cured to be formed.

The organic layer may include a hard mask layer.

According to another embodiment, there is provided a method of manufacturing a semiconductor device, comprising: providing a material layer on a substrate; applying the organic film composition on the material layer; heat treating the organic film composition to form a hard mask layer; Containing thin film layer; forming a photoresist layer on the silicon-containing thin film layer; exposing and developing the photoresist layer to form a photoresist pattern; Selectively removing the hard mask layer and exposing a portion of the material layer, and etching the exposed portion of the material layer.

The step of applying the organic film composition may be performed by a spin-on coating method.

The heat treatment may be performed at a temperature of 100 ° C to 500 ° C.

And forming a bottom anti-reflective layer (BARC) before the step of forming the photoresist layer.

It is possible to provide an organic film which can secure both corrosion resistance and planarization characteristics.

Fig. 1 is a reference diagram for explaining calculation formula 2 for evaluating planarization characteristics.

Hereinafter, exemplary embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.

Unless otherwise defined herein, "substituted" means that the hydrogen atom in the compound is a halogen atom (F, Br, Cl, or I), a hydroxy group, an alkoxy group, a nitro group, a cyano group, an amino group, A thio group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, A C3 to C30 heteroaryl group, a C3 to C30 heteroaryl group, a C3 to C30 cycloalkyl group, a C3 to C30 aryl group, a C7 to C30 arylalkyl group, a C1 to C30 alkoxy group, a C1 to C20 heteroalkyl group, a C2 to C20 hetero aryl group, Substituted with a substituent selected from the group consisting of a cycloalkenyl group, a C 6 to C 15 cycloalkynyl group, a C 2 to C 30 heterocycloalkyl group, and combinations thereof.

In addition, unless otherwise defined herein, "hetero" means containing 1 to 3 heteroatoms selected from N, O, S and P.

Also, unless otherwise defined herein, '*' refers to the point of attachment of a compound or moiety.

Further, the "monovalent group derived from the A compound" means a monovalent group formed by substituting one hydrogen in the A compound. For example, a monovalent group derived from a benzene group is a phenyl group. Further, the term "bivalent group derived from A compound" means a bivalent group in which two hydrogen atoms in A compound are substituted to form two connecting points. For example, a divalent group derived from a benzene group becomes a phenylene group.

An organic film composition according to one embodiment will be described below.

An organic film composition according to one embodiment comprises a first polymer comprising a moiety represented by the following formula (1), a second polymer comprising a moiety represented by the following formula (2), and a solvent.

[Chemical Formula 1]

Figure 112015027780420-pat00016

In Formula 1,

A 1 and A 2 each independently represent a divalent group derived from any one of the compounds listed in Group 1 below,

A 3 and A 4 are each independently a ring group containing at least one substituted or unsubstituted benzene ring,

m is 0 or 1;

[Group 1]

Figure 112015027780420-pat00017

In the group 1,

R 1 , R 2 And R 3 is each independently selected from the group consisting of hydrogen, a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group,

Z 1 to Z 6 each independently represent a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group , A substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, or a combination thereof,

a, b, c, d, e and f are each independently an integer of 0 to 2;

In Group 1, the connection point of each compound is not particularly limited.

(2)

Figure 112015027780420-pat00018

In Formula 2,

B 1 and B 2 are each independently a ring group containing at least one substituted or unsubstituted benzene ring,

B 3 and B 4 are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof,

n is 0 or 1;

In the above formulas (1) and (2), "*"

The organic film composition includes a polymer formed by blending the first polymer and the second polymer.

First, the first polymer will be described.

The first polymer has a structure in which benzylic hydrogen of benzene is minimized and a ring parameter is maximized. By including such a first polymer, the organic film composition can secure excellent corrosion awareness.

The first polymer may include a plurality of moieties represented by Formula 1, and the plurality of moieties may have the same structure or different structures.

R 1 and R 2 which represent a functional group bonded to a nitrogen (N) atom in the above formula (1) And R 3 may be, for example, each independently hydrogen, or a substituted or unsubstituted phenyl group, but is not limited thereto.

A 3 and A 4 each representing a cyclic group containing at least one benzene ring in Formula 1 may independently be any of the groups listed in the following Group 2, but the present invention is not limited thereto.

[Group 2]

Figure 112015027780420-pat00019

In the group 2,

X 1 and X 2 are each independently a substituted or unsubstituted C6 to C50 arylene group, A substituted or unsubstituted C1 to C10 alkylene oxide-containing group, or a combination thereof,

Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C30 aryl group,

Z 7 to Z 10 each independently represent a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group , A substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, or a combination thereof,

g, h, i and j are each independently an integer of 0 to 2,

k is an integer of 1 to 3,

"*" Is the connection point.

The first polymer may comprise at least one of tertiary carbon and quaternary carbon within the monomer structure. In the present specification, a tertiary carbon is a carbon in which three positions of four hydrogens bonded to a carbon are substituted with groups other than hydrogen, and a quaternary carbon is a carbon in which all four of four hydrogen bonded to the carbon are hydrogen Is a carbon in a form substituted with another group.

When a polymer containing this type of carbon is used in an organic film composition, the solubility of the hard mask layer can be improved, which is advantageous for application to a spin-on coating method. Part of the compound containing the tertiary carbon or the quaternary carbon is as listed in the above group 2.

For example, in Group 2, X 1 and X 2 may each independently be a substituted or unsubstituted C6 to C50 arylene group, wherein the C6 to C50 arylene group may be any one of the compounds listed in Group 3 below But it is not limited thereto.

[Group 3]

Figure 112015027780420-pat00020

For example, in the group 2, Y 1 and Y 2 may each independently be a substituted or unsubstituted C6 to C30 aryl group, wherein the C6 to C30 aryl group is derived from any one of the compounds listed in Group 3 But it is not limited thereto.

In the group 3, it is needless to say that the connection point of each ring group is not particularly limited.

In the group 2, when X 1 , X 2 , Y 1 and Y 2 are groups derived from any one of the compounds listed in the group 3, they may be in a form in which at least one hydrogen is substituted by another substituent. The substituent may be, for example, a hydroxy group, a methoxy group, an ethoxy group, a C1 to C10 alkyl group, a C6 to C30 aryl group, or a combination thereof, but is not limited thereto and may be selected depending on the physical properties It is natural to be able to.

Next, the second polymer contained in the organic film composition will be described.

The second polymer may include a plurality of moieties represented by Formula 2, and the plurality of moieties may have the same structure or different structures.

In Formula 2, B 1 and B 2 are each independently a substituted or unsubstituted cyclic group containing at least one or two or more benzene rings, wherein the cyclic group containing at least two benzene rings is, for example, But is not limited to, a bivalent group derived from any one of the listed compounds.

[Group 4]

Figure 112015027780420-pat00021

In Formula 2, when B 1 and B 2 are each independently a bivalent group derived from any one of the compounds listed in Group 4, they may be in a form in which at least one hydrogen is substituted with another substituent. The substituent may be, for example, a hydroxy group, a methoxy group, an ethoxy group, a C1 to C10 alkyl group, a C6 to C30 aryl group, or a combination thereof, but is not limited thereto and may be selected depending on the physical properties It is natural to be able to.

For example, in Formula 2, B 3 and B 4 may each independently be selected from the following Group 5, but the present invention is not limited thereto.

[Group 5]

Figure 112015027780420-pat00022

In the group 5,

R 11 And R 22 are each independently selected from the group consisting of a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,

a1 and a2 each independently represent an integer of 0 to 2,

L x is -O-, -S-, -S = O-, -SO 2 -, -NH-, -C = O-, -CH 2 -, - (CH 3) 2 C-, - (CF 3 ) 2 C-, or a combination thereof,

* Is the connection point.

Since the organic film composition includes the first polymer having the structure of tertiary carbon and / or quaternary carbon, excellent solubility can be secured even if the ring parameter of the polymer is increased. Further, the organic film composition includes the second polymer together with the first polymer so that a void volume between the first polymer generated due to the tertiary carbon and / or the fourth carbon of the first polymer during film formation ) Is filled by the second polymer, so that the mechanical properties and corrosion resistance can be further improved.

For example, the first polymer may be represented by any one of the following formulas (1-1) to (1-4), but is not limited thereto.

[Formula 1-1]

Figure 112015027780420-pat00023

[Formula 1-2]

Figure 112015027780420-pat00024

 [Formula 1-3]

Figure 112015027780420-pat00025

[Formula 1-4]

Figure 112015027780420-pat00026

In the above Formulas 1-1 to 1-4,

Each R 4 is independently hydrogen, a hydroxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

Z 11 To Z 17 are each independently a hydroxy group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkyl alkenyl group, a substituted or unsubstituted C1 to C20 alkyl A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Or a substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, or a combination thereof,

k, l, m, n, o, p, and q are each independently an integer of 0 to 2,

n 0 is an integer from 2 to 300,

* Is the connection point.

For example, the second polymer may be represented by any one of the following general formulas (2-1) to (2-4), but is not limited thereto.

[Formula 2-1]

Figure 112015027780420-pat00027

[Formula 2-2]

Figure 112015027780420-pat00028

[Formula 2-3]

[Chemical Formula 2-4]

Figure 112015027780420-pat00030

In the above Formulas (2-1) to (2-4)

R 33 To R 66 are each independently a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,

a3 to a6 each independently represent an integer of 0 to 2,

n 1 is an integer of 2 to 300,

* Is the connection point.

For example, the weight average molecular weight of the first polymer and the weight average molecular weight of the second polymer may be independently from 500 to 200,000, and the weight average molecular weight of the first and second polymers may be in the range (For example, a hard mask composition) and the solubility in a solvent.

On the other hand, the solvent used in the organic film composition is not particularly limited as long as it has sufficient solubility or dispersibility to the first and second polymers, and examples thereof include propylene glycol, propylene glycol diacetate, methoxypropanediol, diethylene glycol , Diethylene glycol butyl ether, tri (ethylene glycol) monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, ethyl lactate, gamma-butyrolactone, N, , N, N-dimethylacetamide, methylpyrrolidone, methylpyrrolidinone, acetylacetone, and ethyl 3-ethoxypropionate.

The first and second polymers may be included in an amount of about 0.1 to 50% by weight based on the total amount of the organic film composition. By including the first and second polymers in the above range, the thickness, surface roughness and leveling of the organic film can be controlled.

The first and second polymers may be included in a weight ratio of about 97: 3 to 3:97, such as about 9: 1 to 1: 9, about 7: 3 to 3: 7, about 6: 4 to 4: , Or about 5: 5 by weight, but this is by no means limitative.

The organic film composition may further include additives such as a surfactant, a crosslinking agent, a thermal acid generator, and a plasticizer.

The surfactant may be, for example, an alkylbenzenesulfonate, an alkylpyridinium salt, a polyethylene glycol, or a quaternary ammonium salt, but is not limited thereto.

Examples of the cross-linking agent include melamine-based, substitution-based, or polymer-based ones. Preferably, as the crosslinking agent having at least two crosslinking substituents, for example, methoxymethylated glycoluril, butoxymethylated glyceryl, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxy Methylated benzoguanamine, a methoxymethylated urea, a butoxymethylated urea, a methoxymethylated thioether, or a methoxymethylated thioether.

As the crosslinking agent, a crosslinking agent having high heat resistance can be used. As the crosslinking agent having a high heat resistance, a compound containing a crosslinking forming substituent group having an aromatic ring (for example, a benzene ring or a naphthalene ring) in the molecule can be used.

The acid generator may be an acidic compound such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid or naphthalenecarboxylic acid and / , 4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and other organic sulfonic acid alkyl esters, but are not limited thereto.

The additive may be included in an amount of about 0.001 to 40 parts by weight based on 100 parts by weight of the organic film composition. By including it in the above range, the solubility can be improved without changing the optical properties of the organic film composition.

According to another embodiment, there is provided an organic film produced using the organic film composition described above. The organic layer may be in the form of a hardened layer, for example, a hard mask layer, a planarization layer, a sacrificial layer, a filler, etc., and an organic thin film used for electronic devices, .

Hereinafter, a method of forming a pattern using the organic film composition described above will be described.

The method of forming a pattern according to one embodiment includes the steps of providing a material layer on a substrate, applying the above-described organic film composition on the material layer, heat treating the organic film composition to form a hard mask layer, Forming a silicon-containing thin film layer on the silicon-containing thin film layer, forming a photoresist layer on the silicon-containing thin film layer, exposing and developing the photoresist layer to form a photoresist pattern, Selectively removing the thin film layer and the hard mask layer and exposing a portion of the material layer, and etching the exposed portion of the material layer.

The substrate may be, for example, a silicon wafer, a glass substrate, or a polymer substrate.

The material layer is a material to be finally patterned and may be a metal layer such as aluminum, copper, or the like, a semiconductor layer such as silicon, or an insulating layer such as silicon oxide, silicon nitride, or the like. The material layer may be formed by, for example, a chemical vapor deposition method.

The organic film composition is as described above, and may be prepared in a solution form and applied by a spin-on coating method. At this time, the coating thickness of the organic film composition is not particularly limited, but may be applied to a thickness of about 50 to 10,000 ANGSTROM.

The heat treatment of the organic film composition may be performed at about 100 to 500 DEG C for about 10 seconds to 1 hour.

The silicon-containing thin film layer may be formed of a material such as SiCN, SiOC, SiON, SiOCN, SiC and / or SiN.

Further, a bottom anti-reflective coating (BARC) may be further formed on the silicon-containing thin film layer before the step of forming the photoresist layer.

The step of exposing the photoresist layer may be performed using, for example, ArF, KrF or EUV. Further, after the exposure, the heat treatment process may be performed at about 100 to 500 ° C.

The step of etching the exposed portion of the material layer may be performed by dry etching using an etching gas, and the etching gas may be, for example, CHF 3 , CF 4 , Cl 2 , BCl 3 and a mixed gas thereof.

The etched material layer may be formed in a plurality of patterns, and the plurality of patterns may be a metal pattern, a semiconductor pattern, an insulation pattern, or the like, and may be applied to various patterns in a semiconductor integrated circuit device, for example.

Hereinafter, embodiments of the present invention will be described in detail with reference to examples. The following examples are for illustrative purposes only and are not intended to limit the scope of the invention.

Synthetic example

( Synthetic example  1 to 4: Synthesis of first polymer)

Synthetic example  One

The flask was charged with 1H-indole (11.7 g, 0.1 mol), 9-fluorenone (18 g, 0.1 mol), p-toluenesulfonic acid monohydrate (9.5 g, 0.05 mol) and 1,4-dioxane (91 g) were added, followed by stirring at 100 ° C. A sample was taken at intervals of 1 hour from the polymerization reaction product thus obtained, and the reaction was completed when the weight average molecular weight of the sample was 2000 to 3000. After completion of the reaction, 100 g of hexane was added to extract 1,4-dioxane. Methanol was added to the reaction mixture, and the resulting precipitate was filtered. The remaining monomer was removed using methanol to obtain a polymer represented by the following formula 1aa (weight average molecular weight Mw) = 2500).

(1aa)

Figure 112015027780420-pat00031

Synthetic example  2

2-phenyl-1H-indole (19.3 g, 0.1 mol), 9-fluorenone (18 g, 0.1 mol), p-toluenesulfonic acid hydrate (9.5 g, 0.05 mol) and 1,4-dioxane (91 g) were used to obtain a polymer represented by the following formula (1bb) (weight average molecular weight (Mw) = 2300).

≪ RTI ID = 0.0 &

Figure 112015027780420-pat00032

Synthetic example  3

After 4,4'-dibromobiphenyl (1 g, 3.2 mmol) was dissolved in tetrahydrofuran (20 mL), n-BuLi 2.5M (n-BuLi 2.5M in hexane) ) Was slowly added dropwise. After 30 minutes, 9-Fluorenone (1.2 g, 6.4 mmol) dissolved in THF was slowly added dropwise and the mixture was stirred at room temperature for 15 hours. The resulting reaction solution was adjusted to pH = 7 with 1N hydrochloric acid, extracted with EtOAc, and then the solvent was removed. The product was subjected to column chromatography separation to obtain the following compound S1 (synthesis of formula S1).

Figure 112015027780420-pat00033

Synthesis was then carried out using 1H-indole (5.9 g, 50 mmol), compound S1 (25.7 g, 50 mmol), p-toluenesulfonic acid hydrate (4.7 g, 25 mmol) and 1,4- Using the same method as in Example 1, a polymer represented by the formula 1cc was obtained (weight average molecular weight (Mw) = 2900).

[Formula 1cc]

Figure 112015027780420-pat00034

Synthetic example  4

Dibenzo [a, c] carbazole (8.0 g, 30 mmol), the compound S1 (15.4 g, 30 mmol), p- toluenesulfonic acid hydrate (5.7 g, 30 mmol) and 1,4-dioxane (117 g) were used to obtain a polymer represented by the formula (1dd) (weight average molecular weight (Mw) = 2800).

[Chemical Formula 1dd]

Figure 112015027780420-pat00035

( Synthetic example  5 to 8: synthesis of second polymer)

Synthetic example  5

28.33 g (0.2 mol) of 1-naphthol, 28.32 g (0.14 mol) of pyrene and 12.0 g (0.34 mol) of paraformaldehyde were fed into a 500 ml flask. Subsequently, 0.19 g (0.34 mol) of p-toluenesulfonic acid monohydrate was dissolved in 162 g of propylene glycol monomethyl ether acetate (PGMEA) to prepare a solution. The solution was then charged into the flask and stirred at 90 to 100 ° C for 5 to 12 hours Lt; / RTI > Samples were taken from the polymerization reactants at intervals of 1 hour, and the reaction was completed when the weight average molecular weight of the sample was 3500 to 4000.

After completion of the polymerization reaction, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into 40 g of distilled water and 400 g of methanol, stirred vigorously, and allowed to stand. The supernatant was removed, and the precipitate was dissolved in 80 g of propylene glycol monomethyl ether acetate (PGMEA). After stirring vigorously with 320 g of methanol, the solution was allowed to stand (first step). The resulting supernatant was again removed and the precipitate was dissolved in 80 g of propylene glycol monomethyl ether acetate (PGMEA) (2nd order). The primary and secondary processes were referred to as a one-time purification process, and this purification process was performed three times in total. The purified polymer was dissolved in 80 g of propylene glycol monomethyl ether acetate (PGMEA), and methanol and distilled water remaining in the solution were removed under reduced pressure to obtain a polymer represented by the formula (2aa) (weight average molecular weight (Mw) = 4200) .

[Formula 2aa]

Figure 112015027780420-pat00036

Synthetic example  6

10 g (0.055 mol) of 1-hydroxypylene and 9.14 (mol) of 4,4-methoxymethylbenzene were sequentially added to a 500 ml flask and dissolved in 43 g of propylene glycol monomethyl ether acetate (PGMEA). Thereafter, 0.12 g (0.025 mol) of diethylsulfite was added, followed by stirring at 90 to 120 ° C for about 5 to 10 hours. Samples were taken from the polymerization reactants at intervals of 1 hour, and the reaction was completed when the weight average molecular weight of the sample was 4,200 to 5,000.

Thereafter, the purification process was carried out in the same manner as in Synthesis Example 5 to obtain a polymer represented by the formula (2bb) (weight average molecular weight (Mw) = 5100).

(2bb)

Figure 112015027780420-pat00037

Synthetic example  7

350.41 g (1 mol) of 9.9-bishydroxyphenylfluorene, 3.08 g (0.02 mol) of diethyl sulfate and 350 g of propylene glycol monomethyl ether were placed in a 3 L four-necked flask equipped with a mechanical stirrer and a cooling tube, And the mixture was stirred while maintaining the temperature at 115 ° C to completely dissolve it. After 10 minutes, 166.22 g (1 mol) of 1,4-bismethoxymethylbenzene was added dropwise and the reaction was carried out at the same temperature for 15 hours. 2.99 g of triethanolamine as a neutralizing agent was added to terminate the reaction. After completion of the reaction, the acid was removed using a water / methanol mixture, and then the low molecular weight compound containing oligomers and monomers was removed using methanol to obtain a polymer represented by the formula 2cc (Mw = 8,800, dispersion degree = 1.9).

[Formula 2cc]

Figure 112015027780420-pat00038

Synthetic example  8

The reaction was carried out in the same manner as in Synthesis Example 7, except that 242.31 g (1 mol) of 4.4'-bismethoxymethyl-biphenyl was used instead of 166.22 g (1 mol) of 1,4-bismethoxymethylbenzene, To obtain a polymer to be displayed (Mw = 10,500, dispersion degree = 1.9).

[Chemical Formula 2dd]

Figure 112015027780420-pat00039

Hard mask  Preparation of composition

Example  One

The first polymer obtained in Synthesis Example 1 and the second polymer obtained in Synthesis Example 5 were blended at a ratio of 50:50 (weight ratio) to form a novel polymer. 1 g of the obtained novel polymer was dissolved in 1 g of a mixed solvent of propylene glycol monoethylehter acetate (PGMEA) and ethyl lactate (EL) (7: 3 (v / v)), And filtered through a Teflon filter to produce a hard mask composition.

Example  2 to 4

A hard mask composition was prepared in the same manner as in Example 1 except that the second polymer obtained in Synthesis Examples 6 to 8 was used instead of the second polymer obtained in Synthesis Example 5, respectively.

Example  5 to 8

A hard mask composition was prepared in the same manner as in Examples 1 to 4 except that the first polymer obtained in Synthesis Example 2 was used instead of the first polymer obtained in Synthesis Example 1.

Example  9-12

A hard mask composition was prepared in the same manner as in Examples 1 to 4 except that the first polymer obtained in Synthesis Example 3 was used instead of the first polymer obtained in Synthesis Example 1.

Example  13 to 16

A hard mask composition was prepared in the same manner as in Examples 1 to 4 except that the first polymer obtained in Synthesis Example 4 was used instead of the first polymer obtained in Synthesis Example 1.

Comparative Example  1 to 4

A hard mask composition was prepared in the same manner as in Example 1 except that each of the polymers obtained in Synthesis Examples 1 to 4 was used alone instead of the blended new polymer.

Comparative Example  5 to 8

A hard mask composition was prepared in the same manner as in Example 1 except that each of the polymers obtained in Synthesis Examples 5 to 8 was used alone instead of the blended new polymer.

The compositions of the hard mask compositions according to Examples 1 to 16 and Comparative Examples 1 to 8 are shown in Table 1.

The first polymer The second polymer Example 1 (1aa) Formula 2aa Example 2 2bb Example 3 2cc Example 4 2dd Example 5 1bb Formula 2aa Example 6 2bb Example 7 2cc Example 8 2dd Example 9 1cc Formula 2aa Example 10 2bb Example 11 2cc Example 12 2dd Example 13 1dd Formula 2aa Example 14 2bb Example 15 2cc Example 16 2dd Comparative Example 1 (1aa) - Comparative Example 2 1bb - Comparative Example 3 1cc - Comparative Example 4 1dd - Comparative Example 5 - Formula 2aa Comparative Example 6 - 2bb Comparative Example 7 - 2cc Comparative Example 8 - 2dd

evaluation

Rating 1: Film density

The hard mask composition according to Examples 1 and 4 to 16 and Comparative Examples 1 to 4 was spin-on coated on a silicon wafer and heat treated at 400 ° C for 12 minutes by a hot plate to form a thin film having a thickness of 1,000 Å. And the film density of the thin film was measured.

The results are shown in Table 2.

Film density (g / cm 3 ) Example 1 1.29 Example 4 1.26 Example 5 1.29 Example 6 1.27 Example 7 1.26 Example 8 1.27 Example 9 1.26 Example 10 1.25 Example 11 1.27 Example 12 1.26 Example 13 1.24 Example 14 1.28 Example 15 1.22 Example 16 1.25 Comparative Example 1 1.20 Comparative Example 2 1.19 Comparative Example 3 1.18 Comparative Example 4 1.16

Referring to Table 2, it can be seen that the thin films formed from the hard mask compositions according to Examples 1 and 4 to 16 have a higher level of film density than the thin films according to Comparative Examples 1 to 4.

Evaluation 2: Awareness of corrosion

The hard mask composition according to Examples 1, 3, 5, 8, 9, and 16 and Comparative Examples 1 to 8 was spin-on coated on a silicon wafer to a thickness of 4,000 A and heat treated at 400 ° C for 2 minutes on a hot plate to form a thin film And the thickness of the thin film was measured. Subsequently, the thin film was dry-etched using CF 4 gas and N 2 / O 2 mixed gas, and then the thickness of the thin film was measured again. The bulk etch rate (BER) was calculated from the thickness and etch time of the thin film before and after dry etching according to the following equation.

[Equation 1]

(Initial thin film thickness - thin film thickness after etching) / etching time (Å / s)

The results are shown in Table 3.

Bulk etch rate (Å / sec) N 2 O 2 etch CF 4 etch Example 1 24.3 24.0 Example 3 25.2 23.9 Example 5 24.0 23.8 Example 8 24.2 24.1 Example 9 23.9 24.2 Example 16 22.9 24.0 Comparative Example 1 26.3 25.1 Comparative Example 2 25.6 24.9 Comparative Example 3 26.1 26.3 Comparative Example 4 26.8 26.7 Comparative Example 5 28.4 30.2 Comparative Example 6 27.6 29.32 Comparative Example 7 28.1 30.5 Comparative Example 8 29.0 31.0

Referring to Table 3, it can be seen that the thin films formed from the hard mask compositions according to Examples 1, 3, 5, 8, 9, and 16 have a sufficient etch resistance to etching gas as compared with the thin films according to Comparative Examples 1 to 8, It can be confirmed that the characteristics are improved.

Evaluation 3: Gap-fill characteristic and planarization characteristic

The hard mask composition according to Examples 1, 4 to 16 and Comparative Examples 1 to 8 was spin-on coated to a thickness of 1700 Å on a silicon wafer having a pattern formed thereon, and baked at 400 ° C. for 120 seconds to form a thin film.

The gap-fill characteristic was determined by observing the cross section of the pattern with a scanning electron microscope (SEM) to determine voids. The planarization characteristic was measured using a thin film thickness meter of K-MAC Co., Ltd. The thickness of the thin film around the pattern was measured and numerically expressed by the equation 2 shown in Fig. The smaller the difference between h1 and h2, the better the planarization.

The results are shown in Table 4.

Planarization characteristics Gap Fill Character
(with or without void) aspect ratio
(1: 2) aspect ratio
(1:15) Example 1 4.52 70.23 void None Example 4 5.49 68.15 void None Example 5 6.25 78.98 void None Example 6 5.23 76.3 void None Example 7 4.88 67.52 void None Example 8 5.99 69.63 void None Example 9 7.56 76.23 void None Example 10 6.98 75.12 void None Example 11 7.69 67.23 void None Example 12 8.52 76.23 void None Example 13 7.36 75.32 void None Example 14 8.05 79.45 void None Example 15 7.48 76.32 void None Example 16 7.99 81.12 void None Comparative Example 1 9.6 90.21 void occurrence Comparative Example 2 9.8 87.56 void occurrence Comparative Example 3 10.0 89.66 void occurrence Comparative Example 4 10.98 91.33 void occurrence Comparative Example 5 14.36 98.66 void occurrence Comparative Example 6 12.15 90.36 void None Comparative Example 7 13.21 93.48 void None Comparative Example 8 15.83 99.43 void None

Referring to Table 4, it can be seen that the thin films formed from the hard mask compositions according to Examples 1 and 4 to 16 have improved gap-fill and planarization properties compared to the thin films formed from the hard mask composition according to Comparative Examples 1 to 8 . Especially, It can be seen that the thin films formed from the hard mask compositions according to Examples 1 and 4 to 16 have excellent planarization characteristics even at deep depths of the pattern (aspect ratio 1:15).

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, And falls within the scope of the invention.

Claims (19)

A first polymer comprising a moiety represented by Formula 1 below,
A second polymer comprising a moiety represented by the following formula (2), and
menstruum
: ≪ / RTI >
[Chemical Formula 1]
Figure 112017114521871-pat00040

In Formula 1,
A 1 and A 2 are each independently a divalent group derived from any one of the compounds listed in Group 1a below,
A 3 and A 4 are each independently a ring group containing at least one substituted or unsubstituted benzene ring,
m is 0 or 1;
[Group 1a]
Figure 112017114521871-pat00057

In the group 1a,
R 1 , R 2 and R 3 is each independently selected from the group consisting of hydrogen, a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group,
Z 1 to Z 6 each independently represent a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group , A substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, or a combination thereof,
a, b, c, d, e and f are each independently an integer of 0 to 2;
(2)
Figure 112017114521871-pat00042

In Formula 2,
B 1 and B 2 are each independently a ring group containing at least one substituted or unsubstituted benzene ring,
B 3 and B 4 are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof,
n is 0 or 1;
In the above formulas (1) and (2), "*" The method of claim 1,
In Formula 1, A 3 and A 4 are each independently any one of the groups listed in the following Group 2:
[Group 2]
Figure 112015027780420-pat00043

In the group 2,
X 1 and X 2 are each independently a substituted or unsubstituted C6 to C50 arylene group, A substituted or unsubstituted C1 to C10 alkylene oxide-containing group, or a combination thereof,
Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C30 aryl group,
Z 7 to Z 10 each independently represent a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group , A substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, or a combination thereof,
g, h, i and j are each independently an integer of 0 to 2,
k is an integer of 1 to 3,
"*" Is the connection point. 3. The method of claim 2,
In the group 2, X 1 and X 2 are each independently a substituted or unsubstituted C6 to C50 arylene group, and the C6 to C50 arylene group is an organic group which is a divalent group derived from any one of the compounds listed in Group 3 below Composition:
[Group 3]
Figure 112015027780420-pat00044
 3. The method of claim 2,
In the group 2, Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, and the C6 to C30 aryl group is a monovalent group derived from any one of the compounds listed in Group 3 below. :
[Group 3]
Figure 112015027780420-pat00045
 The method of claim 1,
In the group 1, R 1 , R 2 And And R 3 are each independently hydrogen or a substituted or unsubstituted phenyl group. The method of claim 1,
In the formula (2), B 1 and B 2 are each independently a substituted or unsubstituted cyclic group containing at least two benzene rings, and the cyclic group containing at least two benzene rings may be any of the compounds listed in Group 4 An organic film composition which is a bivalent group derived from one of:
[Group 4]
Figure 112015027780420-pat00046
 The method of claim 1,
Wherein B 3 and B 4 in Formula 2 are independently selected from the following Group 5:
[Group 5]
Figure 112015027780420-pat00047

In the group 5,
R 11 And R 22 are each independently selected from the group consisting of a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,
a1 and a2 each independently represent an integer of 0 to 2,
L x is -O-, -S-, -S = O-, -SO 2 -, -NH-, -C = O-, -CH 2 -, - (CH 3) 2 C-, - (CF 3 ) 2 C-, or a combination thereof,
* Is the connection point. The method of claim 1,
Wherein the first polymer is represented by any one of the following formulas (1-1) to (1-4):
[Formula 1-1]
Figure 112015027780420-pat00048

[Formula 1-2]
Figure 112015027780420-pat00049

[Formula 1-3]
Figure 112015027780420-pat00050

[Formula 1-4]
Figure 112015027780420-pat00051

In the above Formulas 1-1 to 1-4,
Each R 4 is independently hydrogen, a hydroxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
Z 11 To Z 17 are each independently a hydroxy group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkyl alkenyl group, a substituted or unsubstituted C1 to C20 alkyl A substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Or a substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, or a combination thereof,
k, l, m, n, o, p, and q are each independently an integer of 0 to 2,
n 0 is an integer from 2 to 300,
* Is the connection point. The method of claim 1,
Wherein the second polymer is represented by any one of the following formulas (2-1) to (2-4):
[Formula 2-1]
Figure 112015027780420-pat00052

[Formula 2-2]
Figure 112015027780420-pat00053

[Formula 2-3]
Figure 112015027780420-pat00054

[Chemical Formula 2-4]
Figure 112015027780420-pat00055

In the above Formulas (2-1) to (2-4)
R 33 To R 66 are each independently a hydroxyl group, a methoxy group, an ethoxy group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,
a3 to a6 each independently represent an integer of 0 to 2,
n 1 is an integer of 2 to 300,
* Is the connection point. The method of claim 1,
Wherein the weight average molecular weight of the first polymer and the weight average molecular weight of the second polymer are independently 500 to 200,000. The method of claim 1,
Wherein the first polymer and the second polymer are contained in a weight ratio of 97: 3 to 3:97. 12. The method of claim 11,
Wherein the first polymer and the second polymer are contained in a weight ratio of 9: 1 to 1: 9. The method of claim 1,
Wherein the first polymer and the second polymer are contained in an amount of 0.1 wt% to 50 wt% based on the total amount of the organic film composition. An organic film formed by curing an organic film composition according to any one of claims 1 to 13. The method of claim 14,
Wherein the organic film comprises a hard mask layer. Providing a layer of material over the substrate,
Applying the organic film composition according to any one of claims 1 to 13 on the material layer,
Heat treating the organic film composition to form a hard mask layer,
Forming a silicon-containing thin film layer on the hard mask layer,
Forming a photoresist layer on the silicon-containing thin film layer,
Exposing and developing the photoresist layer to form a photoresist pattern
Selectively removing the silicon-containing thin film layer and the hard mask layer using the photoresist pattern and exposing a portion of the material layer, and
Etching the exposed portion of the material layer
≪ / RTI > 17. The method of claim 16,
Wherein the step of applying the organic film composition is performed by a spin-on coating method. 17. The method of claim 16,
Wherein the heat treatment is performed at a temperature of 100 ° C to 500 ° C. 17. The method of claim 16,
Further comprising forming a bottom anti-reflective layer (BARC) before the step of forming the photoresist layer.
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