Hard mask composition, hard mask layer, and method of forming pattern

Abstract

A hardmask composition, a hardmask layer manufactured from the hardmask composition, and a method of forming a pattern using the hardmask layer manufactured from the hardmask composition, the hardmask composition comprising: a polymer including a structural unit represented by the following Chemical Formula 1; solvent, [Chemical Formula 1] # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0103085 filed in the Korean Intellectual Property Office on August 7, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Various embodiments relate to a hard mask composition, a hard mask layer, and a method of forming a pattern. Background Art

[0004] Recently, the semiconductor industry has developed ultrafine technology with patterns ranging from several nanometers to tens of nanometers in size. This ultrafine technology can utilize effective photolithography technology.

[0005] Some photolithography techniques may include: providing a material layer on a semiconductor substrate; coating a photoresist layer on the material layer; exposing and developing the photoresist layer to provide a photoresist pattern; and etching the material layer using the photoresist pattern as a mask.

[0006] As the pattern to be formed is miniaturized, it may be difficult to provide a fine pattern with an excellent profile using only some photolithography techniques. Therefore, an auxiliary layer called a hard mask layer may be formed between the material layer and the photoresist layer to provide a fine pattern. Summary of the invention

[0007] The embodiment may be implemented by providing a hard mask composition, the hard mask composition comprising: a polymer including a structural unit represented by Chemical Formula 1; and a solvent,

[0008] [Chemical formula 1]

[0009]

[0010] Wherein in Chemical Formula 1, A is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, wherein two or more substituted or unsubstituted aromatic groups or substituted or unsubstituted heteroaromatic groups are connected by a single bond or -CR x R y - a linked group, or a combination thereof, wherein R x and R y are each independently a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group, R x With R y are separated or connected to form a condensed ring, B is a group represented by Chemical Formula 2, and * is a connection point,

[0011] [Chemical formula 2]

[0012]

[0013] In chemical formula 2, X 1 and X 2 each independently represents a substituted or unsubstituted C1 to C20 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C20 saturated or unsaturated alicyclic hydrocarbon group, a substituted or unsubstituted C1 to C20 saturated or unsaturated heteroaliphatic hydrocarbon group, a substituted or unsubstituted C2 to C20 saturated or unsaturated heteroalicyclic hydrocarbon group, a substituted or unsubstituted C6 to C30 aromatic group, a substituted or unsubstituted C6 to C30 heteroaromatic group, or a combination thereof, X 1 With X 2 are separated or connected to each other to form a substituted or unsubstituted C3 to C30 hydrocarbon ring group, R 1 to R 4 are independently deuterium, hydroxyl, halogen, -NR a R b or a combination thereof, wherein R a and R b each is independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C3 to C20 heterocycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C6 to C20 heteroaryl group, m1 to m4 are each independently an integer from 0 to 4, and n1 and n2 are each independently an integer from 1 to 4.

[0014] A may be a substituted or unsubstituted C6 to C20 aromatic group, wherein two or more substituted or unsubstituted C6 to C20 aromatic rings are connected by a single bond or -CR x R y - a part for connection, or a combination thereof, wherein R x and R y are each independently a substituted or unsubstituted C6 to C10 aromatic ring, R x With R y are separated or connected to form a fused ring.

[0015] A may be a substituted or unsubstituted group that is part of Group 1 or part of Group 2,

[0016] [Group 1]

[0017]

[0018] [Group 2]

[0019]

[0020] In Group 2, Z and Z' can each independently be -O-, -S-, -P- or -NR c -, where R c is hydrogen, deuterium or substituted or unsubstituted C1 to C5 alkyl.

[0021] In chemical formula 2, X 1 and X 2 may each independently be a substituted or unsubstituted C1 to C20 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C20 saturated or unsaturated alicyclic hydrocarbon group, a substituted or unsubstituted C6 to C30 aromatic ring group, or a combination thereof, and X 1 With X 2 The connection may be made to form a substituted or unsubstituted C3 to C20 hydrocarbon cyclic group.

[0022] In chemical formula 2, X 1 and X 2 may each independently be a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and X 1 With X 2 The connection may be made to form a substituted or unsubstituted C3 to C20 hydrocarbon cyclic group.

[0023] In chemical formula 2, R 1 to R 4 Each of m1 to m4 may be independently deuterium, a hydroxyl group, a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and each of m1 to m4 may be independently an integer of 0 to 2.

[0024] In chemical formula 2, X 1 and X 2 may be each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, wherein X 1 With X 2 The connection is made to form a substituted or unsubstituted C3 to C20 hydrocarbon cyclic group, m1 to m4 may each be 0, and n1 and n2 may each independently be 1 or 2.

[0025] Chemical Formula 2 can be represented by one of Chemical Formula 2-1 to Chemical Formula 2-5:

[0026] [Chemical formula 2-1]

[0027]

[0028] [Chemical formula 2-2]

[0029]

[0030] [Chemical formula 2-3]

[0031]

[0032] [Chemical formula 2-4]

[0033]

[0034] [Chemical formula 2-5]

[0035]

[0036] In Chemical Formula 2-1 to Chemical Formula 2-5, * is a connection point.

[0037] Chemical formula 1 can be represented by one of Chemical formula 1-1 to Chemical formula 1-7, [Chemical formula 1-1]

[0038]

[0039] [Chemical formula 1-2]

[0040]

[0041] [Chemical formula 1-3]

[0042]

[0043] [Chemical formula 1-4]

[0044]

[0045] [Chemical formula 1-5]

[0046]

[0047] [Chemical formula 1-6]

[0048]

[0049] [Chemical formula 1-7]

[0050]

[0051] In Chemical Formula 1-1 to Chemical Formula 1-7, * is a connection point.

[0052] The polymer may have a weight average molecular weight of about 1,000 g / mol to about 200,000 g / mol.

[0053] The polymer may be included in an amount of about 0.1 wt % to about 30 wt % based on the total weight of the hardmask composition.

[0054] The solvent may include propylene glycol, propylene glycol diacetate, methoxypropylene glycol, diethylene glycol, diethylene glycol butyl ether, tri(ethylene glycol) monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, ethyl lactate, γ-butyrolactone, N,N-dimethylformamide, N,N-dimethylacetamide, methylpyrrolidone, acetylacetone or ethyl 3-ethoxypropionate.

[0055] The embodiment may be implemented by providing a hard mask layer including a cured product of the hard mask composition according to the embodiment.

[0056] An embodiment can be implemented by providing a method for forming a pattern, the method comprising: providing a material layer on a substrate; applying a hard mask composition according to an embodiment to the material layer; thermally treating the hard mask composition to form a hard mask layer; forming a photoresist layer on the hard mask layer; exposing and developing the photoresist layer to form a photoresist pattern; selectively removing the hard mask layer using the photoresist pattern to expose a portion of the material layer; and etching the exposed portion of the material layer.

[0057] Forming the hard mask layer may include performing a heat treatment at about 100° C. to about 1,000° C. BRIEF DESCRIPTION OF THE DRAWINGS

[0058] Various features will be apparent to those skilled in the art by describing in detail various exemplary embodiments with reference to the accompanying drawings, in which:

[0059] Figure 1 is a reference diagram showing a level difference of a hard mask layer for explaining a method of evaluating planarization characteristics. DETAILED DESCRIPTION

[0060] Exemplary embodiments will now be described more fully below with reference to the accompanying drawings; however, the embodiments may be implemented in different forms and should not be construed as limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete and will fully convey exemplary implementations to those skilled in the art.

[0061] In the accompanying drawings, the sizes of the layers and regions may be exaggerated for clarity of illustration. It should also be understood that when a layer or element is referred to as being "on" another layer or element, the layer or element may be directly on the other layer or element, or there may be intervening layers. In addition, it should also be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or there may be one or more intervening layers.

[0062] When no definition is otherwise provided, "substituted" as used herein may refer to a hydrogen atom of a compound being replaced by a substituent selected from the group consisting of a halogen atom (F, Br, Cl, or I), a hydroxyl group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido group, an amidino group, a hydrazine group, a hydrazo group, a carbonyl group, a carbamoyl group, a thiol group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a vinyl group, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C6 to C30 aryl group, a C7 to C30 arylalkyl group, a C9 to C30 allylaryl group, a C1 to C30 alkoxy group, a C1 to C20 heteroalkyl group, a C3 to C20 heteroarylalkyl group, a C3 to C30 cycloalkyl group, a C3 to C15 cycloalkenyl group, a C6 to C15 cycloalkynyl group, a C3 to C30 heterocycloalkyl group, or a combination thereof. As used herein, hydrogen substitution (—H) may include deuterium substitution (—D) or tritium substitution (—T). For example, any hydrogen in any compound described herein may be protium, deuterium, or tritium (e.g., based on natural substitution or artificial substitution). As used herein, the term “or” is not necessarily an exclusive term, for example, “A or B” will include A, B, or A and B.

[0063] In addition, two adjacent substituents among a substituted halogen atom (F, Br, Cl, or I), a hydroxyl group, a nitro group, a cyano group, an amino group, an azido group, an amidino group, a hydrazine group, a hydrazone group, a carbonyl group, a carbamoyl group, a thiol group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1 to C30 alkyl group, a C2 to C30 alkenyl group, a C2 to C30 alkynyl group, a C6 to C30 aryl group, a C7 to C30 arylalkyl group, a C1 to C30 alkoxy group, a C1 to C20 heteroalkyl group, a C3 to C20 heteroarylalkyl group, a C3 to C30 cycloalkyl group, a C3 to C15 cycloalkenyl group, a C6 to C15 cycloalkynyl group, a C2 to C30 heterocyclyl group may be fused to form a ring.

[0064] When no definition is otherwise provided, the "aromatic hydrocarbon" used herein refers to a group having one or more hydrocarbon aromatic components, including a form in which the hydrocarbon aromatic components are linked by a single bond, a non-aromatic fused ring form in which the hydrocarbon aromatic components are directly or indirectly fused, or a combination thereof, as well as a non-fused aromatic hydrocarbon ring, a fused aromatic hydrocarbon ring.

[0065] More specifically, the substituted or unsubstituted aromatic hydrocarbon may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fused tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryl group, a substituted or unsubstituted indenyl group, a combination thereof, or a fused ring of a combination of the foregoing groups, but is not limited thereto.

[0066] When no definition is otherwise provided, "hetero" as used herein means containing one or more heteroatoms selected from N, O, S, Se and P.

[0067] When no definition is otherwise provided, "heteroaromatic" as used herein means containing at least one atom selected from N, O, S, Se and P in an aromatic hydrocarbon ring.

[0068] More specifically, the substituted or unsubstituted heteroaromatic group may be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzthiazinyl group), substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, pyridoindolyl, benzopyridooxazinyl, benzopyridothiazinyl, 9,9-dimethyl-9,10-dihydroacridinyl, combinations thereof, or fused rings of the above groups, but are not limited thereto.

[0069] When no specific definition is otherwise provided, the term "combination" used herein means mixing or copolymerization.

[0070] As used herein, "polymer" may include both oligomers and polymers.

[0071] Unless otherwise specified in this specification, the “weight average molecular weight” is measured by dissolving a powder sample in tetrahydrofuran (THF) and then using Agilent Technologies' 1200 series Gel Permeation Chromatography (GPC) (column is Shodex Company LF-804, standard sample is Showa Company polystyrene).

[0072] The hard mask composition according to some embodiments may include, for example: a polymer including a structural unit represented by Chemical Formula 1; and a solvent.

[0073] [Chemical formula 1]

[0074]

[0075] In Chemical Formula 1, A may be or may include, for example, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted aromatic group or a heteroaromatic group in which two or more substituted or unsubstituted aromatic groups or heteroaromatic groups are connected by a single bond or -CR x R y - a connected group, or a combination thereof. x and R y Each of R and R may be independently, for example, a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group. x and R y The substituted or unsubstituted aromatic group or the substituted or unsubstituted heteroaromatic group may be separated or may be linked to form a condensed ring.

[0076] B may be, for example, a group represented by Chemical Formula 2.

[0077] * is the connection point,

[0078] [Chemical formula 2]

[0079]

[0080] In chemical formula 2, X 1 and X 2Each independently may be or include, for example, a substituted or unsubstituted C1 to C20 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C20 saturated or unsaturated alicyclic hydrocarbon group, a substituted or unsubstituted C1 to C20 saturated or unsaturated heteroaliphatic hydrocarbon group, a substituted or unsubstituted C2 to C20 saturated or unsaturated heteroalicyclic hydrocarbon group, a substituted or unsubstituted C6 to C30 aromatic ring group, a substituted or unsubstituted C6 to C30 heteroaromatic ring group, or a combination thereof. In an implementation, X 1 With X 2 They may be separated or may be connected to each other to form a substituted or unsubstituted C3 to C30 hydrocarbon ring group.

[0081] R 1 to R 4 may be or include, for example, deuterium, a hydroxyl group, a halogen atom, -NR a R b or a combination thereof, wherein R a and R b and may each independently be hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C3 to C20 heterocycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 heteroaryl group.

[0082] m1 to m4 may each independently be an integer of 0 to 4, for example.

[0083] n1 and n2 may each independently be an integer of 1 to 4, for example.

[0084] In an implementation, the composition may include a polymer including a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, or a connecting portion of these groups in its structural unit, thereby increasing the carbon content in the polymer and ensuring etching resistance. In an implementation, a group represented by Chemical Formula 2 may be included, and the flexibility within the polymer may be increased. The flexible structure may help increase the free volume of the polymer, which may not only help to increase the solubility of the polymer in the solvent, but also reduce the glass transition temperature (Tg) of the composition. In an implementation, the reflow during baking of the composition may be increased, thereby improving the gap filling characteristics and planarization characteristics of the hard mask layer formed by the composition.

[0085] In practice, A may be, for example, a substituted or unsubstituted C6 to C20 aromatic group, wherein two or more substituted or unsubstituted C6 to C20 aromatic groups are connected by a single bond or -CR x R y - a group for connection, or a combination thereof, wherein R x and R y Each independently may be a substituted or unsubstituted C6 to C10 aromatic ring, wherein these aromatic rings may be connected to form a condensed ring. In an implementation manner, A may be, for example, a substituted or unsubstituted group of a part of Group 1 or a part of Group 2. In an implementation manner, A may be, for example, a substituted or unsubstituted group of a part of Group 1.

[0086] [Group 1]

[0087]

[0088] [Group 2]

[0089]

[0090] In Group 2, Z and Z' can each independently be, for example, -O-, -S-, -P- or -NR c -, where R c It may be, for example, hydrogen, deuterium, or a substituted or unsubstituted C1 to C5 alkyl group.

[0091] In an implementation, A may be or may include, for example, benzene, naphthalene, anthracene, phenanthrene, pyrene, a fluorene derivative, indole, carbazole, or benzocarbazole, which may be substituted or unsubstituted.

[0092] In the implementation method, in the chemical formula 2, X 1 and X 2 Each of them may be independently, for example, a substituted or unsubstituted C1 to C20 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C20 saturated or unsaturated alicyclic hydrocarbon group, a substituted or unsubstituted C6 to C30 aromatic ring group, or a combination thereof. 1 and X 2 The connection may be made to form a substituted or unsubstituted C3 to C20 hydrocarbon cyclic group or hydrocarbon cyclic group. 1 and X 2 Each of them may be, for example, independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof. In the implementation mode, X 1 With X 2 The connection may be made to form a substituted or unsubstituted C3 to C20 hydrocarbon cyclic group or hydrocarbon ring group.

[0093] Connect via X 1 With X 2 In the substituted or unsubstituted C3 to C20 hydrocarbon ring group formed, the cycloalkyl group, cycloalkenyl group, cycloalkynyl group or aromatic ring may exist alone, or two or more hydrocarbon rings may be condensed. 1 and X 2 may be an alkyl group, and X 1 With X 2 Can be linked to form cyclopentane, cyclohexane, etc. In practice, X 1 and X 2 Can be an aromatic group, such as X 1 and X 2 Each may be a phenyl group, and two carbon atoms present in the ortho position of the carbon atom of the phenyl group may be connected to the quaternary carbon, X 1 and X 2 The connection to the quaternary carbon is made through a single bond to form fluorene, and the hydrocarbon ring group may be substituted or unsubstituted.

[0094] In the implementation, X 1 With X 2 Can exist independently or separately, or X 1 With X 2 Can be connected and exist as a part or group. In the implementation mode, by X 1 The structure and X 2 By appropriately adjusting the structure of to adjust the flexibility of the structural unit represented by Chemical Formula 2, the solubility of a polymer including the structural unit in a solvent can be adjusted.

[0095] In an implementation, in Formula 2, R 1 to R 4 Each of them may be independently, for example, deuterium, a hydroxyl group, a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, such as a hydroxyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C1 to C10 alkyl group, or a combination thereof. In an implementation, in Formula 2, R 1 to R 4 Each independently may be, for example, a hydroxyl group.

[0096] In an implementation, in Chemical Formula 2, m1 to m4 may each independently be an integer such as 0 to 4, 0 to 2, 0 or 1, or 0.

[0097] In an implementation manner, in Chemical Formula 2, n1 and n2 may each independently be an integer of, for example, 1 to 4, 1 to 3, or 1 or 2. By adjusting n1 and n2, the flexibility within the structural unit may be adjusted, and the solubility of a polymer including the structural unit in a solvent may be adjusted.

[0098] In an implementation, Chemical Formula 2 may be represented by, for example, one of Chemical Formula 2-1 to Chemical Formula 2-5.

[0099] [Chemical formula 2-1]

[0100]

[0101] [Chemical formula 2-2]

[0102]

[0103] [Chemical formula 2-3]

[0104]

[0105] [Chemical formula 2-4]

[0106]

[0107] [Chemical formula 2-5]

[0108]

[0109] In Chemical Formula 2-1 to Chemical Formula 2-5, * is a connection point.

[0110] In an implementation, Chemical Formula 1 may be represented by, for example, one of Chemical Formula 1-1 to Chemical Formula 1-7.

[0111] [Chemical formula 1-1]

[0112]

[0113] [Chemical formula 1-2]

[0114]

[0115] [Chemical formula 1-3]

[0116]

[0117] [Chemical formula 1-4]

[0118]

[0119] [Chemical formula 1-5]

[0120]

[0121] [Chemical formula 1-6]

[0122]

[0123] [Chemical formula 1-7]

[0124]

[0125] In Chemical Formula 1-1 to Chemical Formula 1-7, * is a connection point.

[0126] The polymer may have a weight average molecular weight of, for example, about 1,000 g / mol to about 200,000 g / mol. In practice, the polymer may have a weight average molecular weight of, for example, about 1,000 g / mol to about 150,000 g / mol, about 1,000 g / mol to about 100,000 g / mol, about 1,200 g / mol to about 50,000 g / mol, or about 1,200 g / mol to about 10,000 g / mol. By making the weight average molecular weight within the above range, the carbon content and solubility in the solvent of the hard mask composition including the above polymer can be adjusted and optimized.

[0127] The polymer may be included in an amount of, for example, about 0.1 wt % to about 30 wt % based on the total weight of the hard mask composition. In an implementation, the polymer may be included in an amount of, for example, about 0.2 wt % to about 30 wt %, about 0.5 wt % to about 30 wt %, about 1 wt % to about 30 wt %, about 1.5 wt % to about 25 wt %, or about 2 wt % to about 20 wt %. By including the polymer within the above range, the thickness, surface roughness, and planarization degree of the hard mask may be easily adjusted.

[0128] The hard mask composition may include a solvent. In an implementation, the solvent may include, for example, propylene glycol, propylene glycol diacetate, methoxypropylene glycol, diethylene glycol, diethylene glycol butyl ether, tri(ethylene glycol) monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, ethyl lactate, γ-butyrolactone, N,N-dimethylformamide, N,N-dimethylacetamide, methyl pyrrolidone, acetylacetone, ethyl 3-ethoxypropionate, or a similar solvent. In an implementation, the solvent may include a suitable solvent having sufficient solubility or dispersibility for the polymer.

[0129] The hard mask composition may further include additives such as a surfactant, a cross-linking agent, a thermal acid generator, or a plasticizer.

[0130] The surfactant may include, for example, a fluoroalkyl compound, an alkylbenzenesulfonate, an alkylpyridinium salt, polyethylene glycol, a quaternary ammonium salt, or the like.

[0131] The crosslinking agent may include, for example, melamine, substituted urea or a polymer crosslinking agent. In practice, the crosslinking agent may be a crosslinking agent having at least two crosslinking substituents, such as methoxymethylated glycouryl, butoxymethylated glycoluryl, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea or butoxymethylated thiourea.

[0132] In an implementation, as the crosslinking agent, a crosslinking agent having high heat resistance may be used. The crosslinking agent having high heat resistance may include a compound containing a crosslinking substituent having an aromatic ring (eg, a benzene ring or a naphthalene ring) in a molecule.

[0133] The thermal acid generator may include, for example, an acid compound (e.g., p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthoic acid) or 2,4,4,6-tetrabromocyclohexadienonone, benzoin tosylate, 2-nitrobenzyl tosylate or other organic alkyl sulfonates.

[0134] According to some embodiments, a hard mask layer including a cured product of the aforementioned hard mask composition may be provided.

[0135] Hereinafter, a method of forming a pattern using the aforementioned hard mask composition is described.

[0136] According to some embodiments, the method of forming a pattern may include: providing a material layer on a substrate; applying a hard mask composition comprising the aforementioned polymer and a solvent to the material layer; thermally treating the hard mask composition to form a hard mask layer; forming a photoresist layer on the hard mask layer; exposing and developing the photoresist layer to form a photoresist pattern; selectively removing the hard mask layer using the photoresist pattern to expose a portion of the material layer; and etching the exposed portion of the material layer.

[0137] 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, such as a metal layer (e.g., an aluminum layer or a copper layer), a semiconductor layer (e.g., a silicon layer), or an insulating layer (e.g., a silicon oxide layer or a silicon nitride layer). The material layer may be formed by a method such as a chemical vapor deposition (CVD) process.

[0138] The hard mask composition may be the same as described above and may be applied by spin coating from a solution. In practice, the hard mask composition may be applied to a thickness of, for example, about To date

[0139] The hard mask composition may be thermally treated at about 100° C. to about 1,000° C. for about 10 seconds to about 1 hour. In an implementation, the thermal treatment of the hard mask composition may include a plurality of thermal treatment processes, such as a first thermal treatment process and a second thermal treatment process.

[0140] In an implementation, the heat treatment of the hard mask composition may include, for example, performing a heat treatment process at about 100° C. to about 1,000° C. for about 10 seconds to about 1 hour. In an implementation, the heat treatment may be performed in an air atmosphere or a nitrogen atmosphere or in an atmosphere with an oxygen concentration of 1 wt % or less.

[0141] In an implementation, the heat treatment of the hard mask composition may include, for example, a first heat treatment process, which is performed at about 100°C to about 1,000°C, about 100°C to about 800°C, about 100°C to about 500°C, or about 150°C to about 400°C for, for example, about 30 seconds to about 1 hour, about 30 seconds to about 30 minutes, about 30 seconds to about 10 minutes, or about 30 seconds to about 5 minutes.

[0142] In an implementation, the heat treatment of the hard mask composition may include, for example, a second heat treatment process, which is continuously performed at about 100° C. to 1,000° C., about 300° C. to about 1,000° C., about 500° C. to about 1,000° C., about 500° C. to about 600° C. for, for example, about 30 seconds to about 1 hour, about 30 seconds to about 30 minutes, about 30 seconds to about 10 minutes, or about 30 seconds to about 5 minutes. In an implementation, the first heat treatment process and the second heat treatment process may be performed in an air or nitrogen atmosphere, or may be performed in an atmosphere having an oxygen concentration of 1 wt % or less.

[0143] By performing at least one of the steps of heat-treating the hard mask composition at a high temperature, for example, 200° C. or higher, high etching resistance capable of withstanding etching gas and chemical liquid exposed in subsequent processes including an etching process may be exhibited.

[0144] In an implementation, the formation of the hard mask layer may include an ultraviolet (UV) / visible light (Vis) curing process or an infrared ray (IR) curing process.

[0145] In an implementation, the formation of the hard mask layer may include a first heat treatment process, a second heat treatment process, a UV / Vis curing process, or a near IR curing process, or may include two or more processes in succession.

[0146] In an implementation, the method may further include forming a silicon-containing thin layer on the hard mask layer. The silicon-containing thin layer may be formed of, for example, SiCN, SiOC, SiON, SiOCN, SiC, SiO, SiN, etc.

[0147] In an implementation, the method may further include: before forming the photoresist layer, forming a bottom antireflective coating (BARC) on the silicon-containing thin layer or on the hard mask layer.

[0148] In an implementation, the exposure of the photoresist layer may be performed using, for example, ArF, KrF, or extreme ultraviolet (EUV). After the exposure, a heat treatment may be performed at about 100° C. to about 700° C.

[0149] In an implementation, the etching process of the exposed portion of the material layer may be performed by a dry etching process using an etching gas, and the etching gas may be, for example, N 2 / O 2 , CHF 3 CF 4 , Cl 2 , BCl 3 or a mixture of gases.

[0150] The etched material layer may be formed into a plurality of patterns, and the plurality of patterns may include metal patterns, semiconductor patterns, insulating patterns, or the like, such as various patterns of semiconductor integrated circuit devices.

[0151] The following examples and comparative examples are provided to highlight the characteristics of one or more embodiments, but it should be understood that the examples and comparative examples should not be interpreted as limiting the scope of the embodiments, and the comparative examples should not be interpreted as exceeding the scope of the embodiments. In addition, it should be understood that the embodiments are not limited to the specific details set forth in the examples and comparative examples.

[0152] Synthesis of compounds

[0153] Synthesis example 1

[0154] 1,1-bis(4-hydroxyphenyl)cyclohexane (80.5 g, 0.3 mol), 4-fluorobenzaldehyde (74.5 g, 0.6 mol), potassium carbonate (82.9 g, 0.6 mol) and 400 ml of anhydrous N,N-dimethylformamide (DMF) were placed in a flask and stirred for 14 hours at 140 ° C in nitrogen. When the reaction was completed, the reactants were cooled to ambient temperature and slowly added dropwise to cold water (1,000 ml). The resulting solid was filtered and then washed twice with 500 ml of water and methanol aqueous solution (water: MeOH = 5: 1, 200 ml), and the residual solvent was removed under reduced pressure to obtain compound 1a represented by chemical formula 1a.

[0155] [Chemical formula 1a]

[0156]

[0157] Compound 1a (95.3 g, 0.2 mol) was dissolved in dichloromethane: MeOH (1:1, 500 ml), and sodium borohydride (22.7 g, 0.6 mol) was slowly added thereto at ambient temperature over 20 minutes, and then stirred at ambient temperature for 5 hours. When the reaction was complete, after removing about half of the solvent under reduced pressure, the organic layer was extracted with 600 ml of ethyl acetate, and the remaining solvent was removed, thereby obtaining compound 1b represented by chemical formula 1b.

[0158] [Chemical formula 1b]

[0159]

[0160] Compound 1b (48.0 g, 0.1 mol) was dissolved in 150 ml of anhydrous DMF, and sodium hydride (7.2 g, 0.3 mol) was slowly added thereto while blowing nitrogen, and then stirred for another 30 minutes at ambient temperature. Subsequently, iodomethane (71.0 g, 0.5 mol) was slowly added dropwise to the reactant, and then stirred for another 3 hours at ambient temperature.

[0161] When the reaction was completed, the organic layer was extracted therefrom using 500 mL of ethyl acetate by column chromatography, and the remaining solvent was removed under reduced pressure to obtain Compound 1 represented by Chemical Formula A.

[0162] [Chemical formula A]

[0163]

[0164] Synthesis example 2

[0165] Compound 2 represented by Chemical Formula B was obtained in the same manner as in Synthesis Example 1, except that 3-fluorobenzaldehyde (0.6 mol) was used instead of 4-fluorobenzaldehyde.

[0166] [Chemical formula B]

[0167]

[0168] Synthesis example 3

[0169] Compound 3 represented by Chemical Formula C was obtained in the same manner as in Synthesis Example 1, except that 1,1-bis(4-hydroxyphenyl)cyclopentane (0.3 mol) was used instead of 1,1-bis(4-hydroxyphenyl)cyclohexane.

[0170] [Chemical formula C]

[0171]

[0172] Synthesis example 4

[0173] Compound 1a (95.3 g, 0.2 mol), 3-chloroperbenzoic acid (mCPBA) (86.3 g, 0.5 mol) and 200 ml of chloroform were placed in a flask and stirred at ambient temperature for 4 hours. When the reaction was completed, after removing the solvent under reduced pressure, the solid generated therein was filtered and removed, and the resulting filtrate was purified by column chromatography to obtain Compound 4a represented by Chemical Formula 4a.

[0174] [Chemical formula 4a]

[0175]

[0176] Compound 4 represented by Chemical Formula D was obtained in the same manner as in Synthesis Example 1, except that Compound 4a (0.3 mol) was used instead of 1,1-bis(4-hydroxyphenyl)cyclohexane.

[0177] [Chemical formula D]

[0178]

[0179] Synthesis example 5

[0180] Compound 5 represented by Chemical Formula E was obtained in the same manner as in Synthesis Example 1, except that bisphenol A (0.3 mol) was used instead of 1,1-bis(4-hydroxyphenyl)cyclohexane.

[0181] [Chemical formula E]

[0182]

[0183] Synthesis example 6

[0184] Compound 6 represented by Chemical Formula F was obtained in the same manner as in Synthesis Example 1, except that 9,9-bis(4-hydroxyphenyl)fluorene (0.3 mol) was used instead of 1,1-bis(4-hydroxyphenyl)cyclohexane.

[0185] [Chemical formula F]

[0186]

[0187] Polymer synthesis

[0188] Polymerization Example 1

[0189] 9,9-bis(6-hydroxy-2-naphthyl)fluorene (22.5 g, 0.05 mol), compound 1 (25.4 g, 0.05 mol), diethyl sulfate (0.15 g), propylene glycol monomethyl ether acetate (PGMEA, 150 g) were placed in a flask in sequence, and then stirred at 90°C for 6 hours for polymerization. When the reaction was completed, the reactants were added to 40 g of distilled water and 200 g of methanol, and then stirred vigorously and allowed to stand. Subsequently, after removing the supernatant, the resulting precipitate was dissolved in 80 g of propylene glycol monomethyl ether acetate, and then stirred with 200 g of methanol and allowed to stand. This purification process was performed twice more, the purified polymer was dissolved in 80 g of PGMEA, and the remaining solvent was removed under reduced pressure, thereby obtaining a polymer 1 comprising a structural unit represented by chemical formula 1-1. (weight average molecular weight = 3000 g / mol)

[0190] [Chemical formula 1-1]

[0191]

[0192] Polymerization Example 2

[0193] A polymer 2 including a structural unit represented by Chemical Formula 1-2 was obtained in the same manner as in Polymerization Example 1 except that 0.05 mol of 1-hydroxypyrene was used instead of 9,9-bis(6-hydroxy-2-naphthyl)fluorene. (Weight average molecular weight = 3000 g / mol)

[0194] [Chemical formula 1-2]

[0195]

[0196] Polymerization Example 3

[0197] Polymer 3 including the structural unit represented by Chemical Formula 1-3 was obtained in the same manner as in Polymerization Example 1 except that Compound 2 was used instead of Compound 1. (Weight average molecular weight = 3000 g / mol)

[0198] [Chemical formula 1-3]

[0199]

[0200] Polymerization Example 4

[0201] Polymer 4 including the structural unit represented by Chemical Formula 1-4 was obtained in the same manner as in Polymerization Example 1 except that Compound 3 was used instead of Compound 1. (Weight average molecular weight = 3000 g / mol)

[0202] [Chemical formula 1-4]

[0203]

[0204] Polymerization Example 5

[0205] Polymer 5 including the structural unit represented by Chemical Formula 1-5 was obtained in the same manner as in Polymerization Example 1 except that Compound 4 was used instead of Compound 1. (Weight average molecular weight = 3000 g / mol)

[0206] [Chemical formula 1-5]

[0207]

[0208] Polymerization Example 6

[0209] Polymer 6 including the structural unit represented by Chemical Formula 1-6 was obtained in the same manner as in Polymerization Example 1 except that Compound 5 was used instead of Compound 1. (Weight average molecular weight = 3000 g / mol)

[0210] [Chemical formula 1-6]

[0211]

[0212] Polymerization Example 7

[0213] Polymer 7 including the structural unit represented by Chemical Formula 1-7 was obtained in the same manner as in Polymerization Example 1 except that Compound 6 was used instead of Compound 1. (Weight average molecular weight = 3000 g / mol)

[0214] [Chemical formula 1-7]

[0215]

[0216] Comparative Polymerization Example 1

[0217] 28.83 g (0.2 mol) of 1-naphthol, 41.4 g (0.15 mol) of benzoperylene and 12.08 g (0.4 mol) of p-formaldehyde were placed in a three-necked flask, and 0.57 g (0.003 mol) of p-toluenesulfonic acid monohydrate was dissolved in 163 g of PGMEA, and then stirred at 60 ° C for 18 hours for polymerization. When the reaction was completed, the reactants were added to 40 g of distilled water and 400 g of methanol, and then stirred vigorously and allowed to stand. Subsequently, after removing the supernatant, the resulting precipitate was dissolved in 80 g of PGMEA, and then 320 g of methanol was used for vigorous stirring and allowed to stand. This purification process was carried out twice more, the purified polymer was dissolved in 80 g of PGMEA, and the methanol and distilled water remaining in the solution were removed under reduced pressure. Then, 1 liter of tetrahydrofuran was added to the concentrated solution, and then slowly dropped into a beaker containing 1 liter of hexane while stirring to form a precipitate, and thereby a comparative polymer 1 including a structural unit represented by Chemical Formula X was obtained. (Weight average molecular weight (Mw) = 4,000 g / mol, polydispersity (PD) = 1.75)

[0218] [Chemical formula X]

[0219]

[0220] Comparative Polymerization Example 2

[0221] Comparative polymer 2 including a structural unit represented by Chemical Formula Y was obtained in the same manner as in Polymerization Example 1 except that 4,4′-bis(methoxymethyl)diphenyl ether was used instead of Compound 1. (Weight average molecular weight (Mw)=3000 g / mol)

[0222] [Chemical formula Y]

[0223]

[0224] Preparation of hard mask composition

[0225] Examples 1 to 7 and Comparative Examples 1 to 2

[0226] 3.5 g of each of Polymer 1 to Polymer 7 and Comparative Polymer 1 and Comparative Polymer 2 of Polymerization Examples 1 to 7 and Comparative Polymer 1 and Comparative Polymer 2 were dissolved in 10 g of a mixed solvent of PGMEA and cyclohexanone in a volume ratio of 7:3, and then filtered using a syringe filter to prepare a hard mask composition solution.

[0227] Evaluation 1: Evaluation of heat resistance

[0228] Each of the hard mask compositions according to Examples 1 to 7 and Comparative Examples 1 and 2 was coated on a silicon wafer, and heat treated on a hot plate at 150° C. for 2 minutes, and then cut into pellets using a knife, and subjected to thermogravimetric (TGA) analysis under elevated temperature conditions in air. The results are shown in Table 1. In Table 1, T 95 Indicates the temperature at which the remaining weight reaches 95% of the initial weight, and T 90 Indicates the temperature at which the remaining weight reaches 90% of the initial weight.

[0229] [Table 1]

[0230] <![CDATA[T 95 (℃)]]> <![CDATA[T 90 (℃)]]> Example 1 418 459 Example 2 411 449 Example 3 410 458 Example 4 400 451 Example 5 420 460 Example 6 385 446 Example 7 390 449 Comparative Example 1 328 367 Comparative Example 2 383 437

[0231] Referring to Table 1, the hard mask layers formed of the compositions according to Examples 1 to 7 exhibited higher thermal decomposition temperatures than the hard mask layers formed of the compositions according to Comparative Examples 1 and 2. The hard mask layers of Examples exhibited superior heat resistance compared to the hard mask layers of Comparative Examples.

[0232] Evaluation 2: Gap Fill and Planarization Characteristics

[0233] Each of the hard mask compositions of Examples 1 to 7 and Comparative Examples 1 and 2 was coated on a patterned wafer, and then heat-treated on a hot plate at 400° C. for 2 minutes, thereby forming a 2,000 angstrom-thick hard mask layer. Figure 1 is a reference diagram exemplarily showing steps of a hard mask layer to explain a method of evaluating planarization characteristics.

[0234] The planarization characteristics were evaluated by measuring the thickness at three random points on the non-patterned portion of the substrate using a film thickness gauge manufactured by K-MAC Co., Ltd. and calculating the average value h 1 , and furthermore measure the film thickness at three random points on the patterned portion of the substrate and calculate its average value h 2 , and thus calculate the step (|h 1 -h 2 |). Stairs(|h 1 -h 2 The smaller |) is, the better the planarization characteristics are.

[0235] The gap-filling property was evaluated by observing the cross section of the pattern using a scanning electron microscope (SEM) to check whether a void was generated, and the results are shown in Table 2.

[0236] [Table 2]

[0237]

[0238]

[0239] Referring to Table 2, the hard mask layers formed from the hard mask compositions according to Examples 1 to 7 exhibited h 1 With h 2 The difference between the hard mask layers of Comparative Examples 1 and 2 was relatively small, and no voids were observed in the pattern. In contrast, the hard mask layers formed from the hard mask compositions according to Comparative Examples 1 and 2 exhibited a relatively small difference between the hard mask layers of Comparative Examples 1 and 2. 1 With h 2 The difference between φ and φ was relatively large, and at the same time, voids were observed within the pattern in the case of Comparative Example 1. In other words, the hard mask layer formed of the hard mask composition of Example exhibited excellent planarization characteristics as well as excellent gap-fill characteristics.

[0240] In summary, there is a continuous trend to reduce chip size in the semiconductor industry. For this reason, the line width of the patterned resist in photolithography must be tens of nanometers. Therefore, the height of the line width that can withstand the resist pattern may be limited, and there is a situation where the resist does not have sufficient tolerance in the etching step. In order to compensate for this, an auxiliary layer called a hard mask layer can be used between the material layer to be etched and the photoresist layer. Such a hard mask layer is used as an interlayer (interlayer) for transferring the fine pattern of the photoresist by selective etching, and therefore the hard mask layer is required to have etching resistance and cross-linking properties to withstand the etching process required for pattern transfer.

[0241] Some hard mask layers can be formed by chemical or physical deposition methods, and may have low economic efficiency due to large-scale equipment and high process costs. Therefore, spin coating techniques for forming hard mask layers have been developed recently. Spin coating techniques may be a process that is easier to perform than some other methods, and hard mask layers formed by spin coating techniques may exhibit excellent gap filling properties and planarization properties. However, in hard mask layers formed using spin coating techniques, the required etch resistance may be slightly reduced. Therefore, spin coating techniques may be used to apply hard mask compositions to ensure etch resistance equivalent to that of hard mask layers formed in chemical or physical deposition methods.

[0242] Therefore, in order to improve the etching resistance of the hard mask layer, research on maximizing the carbon content of the hard mask composition is being conducted. However, as the carbon content of the polymer included in the hard mask composition is maximized, the solubility of the compound in the solvent may decrease. Therefore, the carbon content of the polymer included in the hard mask composition should be maximized to improve the etching resistance of the hard mask layer formed therefrom, and the polymer must have good solubility in the solvent.

[0243] The hard mask composition according to some embodiments may include a polymer including an aromatic hydrocarbon group or a heteroaromatic group, thereby increasing the carbon content in the polymer and ensuring the etching resistance of the hard mask layer formed thereby. At the same time, by including a portion having high flexibility in the polymer, the solubility of the polymer in a solvent is increased, so that the gap filling and planarization characteristics of the hard mask layer formed by the composition can be improved, and the heat resistance can be improved.

[0244] One or more embodiments may provide a hard mask composition that can be effectively applied to a hard mask layer.

[0245] The hard mask composition according to some embodiments may have excellent solubility in a solvent and may be effectively applied to a hard mask layer.

[0246] A hard mask layer formed of the hard mask composition according to some embodiments may help ensure excellent heat resistance while simultaneously ensuring gap filling characteristics and planarization characteristics.

[0247] Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used and should be interpreted in a general and illustrative sense only and not for purposes of limitation. In some cases, it will be apparent to one of ordinary skill in the art at the time this application is filed that features, characteristics, and / or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless otherwise specifically stated. Therefore, it will be understood by one of ordinary skill in the art that various changes in form and detail may be made without departing from the spirit and scope of the invention as set forth in the claims above.

Claims

1. A hard mask composition comprising: A polymer including a structural unit represented by Chemical Formula 1; and Solvents, [Chemical formula 1] Wherein in Chemical Formula 1, A is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, or a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group in which two or more substituted or unsubstituted aromatic groups or substituted or unsubstituted heteroaromatic groups are connected by a single bond or -CR x R y - a linked group, or a combination thereof, wherein R x and R y are each independently a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group, R x With R y are separated or connected to form a fused ring, B is a group represented by Chemical Formula 2, and * is the connection point, [Chemical formula 2] Wherein in Chemical Formula 2, X 1 and X 2 each independently represents a substituted or unsubstituted C1 to C20 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C20 saturated or unsaturated alicyclic hydrocarbon group, a substituted or unsubstituted C1 to C20 saturated or unsaturated heteroaliphatic hydrocarbon group, a substituted or unsubstituted C2 to C20 saturated or unsaturated heteroalicyclic hydrocarbon group, a substituted or unsubstituted C6 to C30 aromatic group, a substituted or unsubstituted C6 to C30 heteroaromatic group, or a combination thereof, X 1 With X 2 are separated or connected to each other to form a substituted or unsubstituted C3 to C30 hydrocarbon ring group, R 1 to R 4 are independently deuterium, hydroxyl, halogen, -NR a R b or a combination thereof, wherein R a and R b each independently represents hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C3 to C20 heterocycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 heteroaryl group, m1 to m4 are each independently an integer from 0 to 4, and n1 and n2 are each independently an integer of 1 to 4.

2. The hardmask composition according to claim 1, wherein A is a substituted or unsubstituted C6 to C20 aromatic group, wherein two or more substituted or unsubstituted C6 to C20 aromatic rings are connected by a single bond or -CR x R y - a part for connection, or a combination thereof, wherein R x and R y are each independently a substituted or unsubstituted C6 to C10 aromatic ring, R x With R y are separated or connected to form a fused ring.

3. The hard mask composition according to claim 1, wherein: A is a substituted or unsubstituted group of a moiety of Group 1 or a moiety of Group 2, [Group 1] [Group 2] In Group 2, Z and Z' are each independently -O-, -S-, -P- or -NR c -, where R c is hydrogen, deuterium or substituted or unsubstituted C1 to C5 alkyl.

4. The hard mask composition according to claim 1, wherein in Chemical Formula 2, X 1 and X 2 are each independently a substituted or unsubstituted C1 to C20 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C20 saturated or unsaturated alicyclic hydrocarbon group, a substituted or unsubstituted C6 to C30 aromatic ring group, or a combination thereof, and X 1 With X 2 The connection is made to form a substituted or unsubstituted C3 to C20 hydrocarbon ring group.

5. The hard mask composition according to claim 1, wherein in Chemical Formula 2, X 1 and X 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and X 1 With X 2 The connection is made to form a substituted or unsubstituted C3 to C20 hydrocarbon ring group.

6. The hard mask composition according to claim 1, wherein in Chemical Formula 2, R 1 to R 4 are each independently deuterium, a hydroxyl group, a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and m1 to m4 are each independently an integer from 0 to 2.

7. The hard mask composition according to claim 1, wherein in Chemical Formula 2, X 1 and X 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, wherein X 1 With X 2 are connected to form a substituted or unsubstituted C3 to C20 hydrocarbon ring group, m1 to m4 are each 0, and n1 and n2 are each independently 1 or 2.

8. The hard mask composition according to claim 1, wherein: Chemical Formula 2 is represented by one of Chemical Formula 2-1 to Chemical Formula 2-5: [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] [Chemical formula 2-4] [Chemical formula 2-5] In Chemical Formula 2-1 to Chemical Formula 2-5, * is a connection point.

9. The hard mask composition according to claim 1, wherein: Chemical formula 1 is represented by one of Chemical formula 1-1 to Chemical formula 1-7, [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] [Chemical formula 1-6] [Chemical formula 1-7] In Chemical Formula 1-1 to Chemical Formula 1-7, * is a connection point. 10 . The hardmask composition of claim 1 , wherein the polymer has a weight average molecular weight of about 1,000 to about 200,000 g / mol. 11 . The hardmask composition of claim 1 , wherein the polymer is included in an amount of 0.1 wt % to 30 wt % based on the total weight of the hardmask composition.

12. The hardmask composition according to claim 1, wherein the solvent comprises propylene glycol, propylene glycol diacetate, methoxypropylene glycol, diethylene glycol, diethylene glycol butyl ether, tri(ethylene glycol) monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, ethyl lactate, γ-butyrolactone, N,N-dimethylformamide, N,N-dimethylacetamide, methylpyrrolidone, acetylacetone or ethyl 3-ethoxypropionate. 13 . A hard mask layer comprising a cured product of the hard mask composition according to claim 1 .

14. A method for forming a pattern, the method comprising: providing a material layer on a substrate; applying the hard mask composition according to claim 1 to the material layer; thermally treating the hard mask composition to form a hard mask layer; forming a photoresist layer on the hard mask layer; exposing and developing the photoresist layer to form a photoresist pattern; selectively removing the hard mask layer using the photoresist pattern to expose a portion of the material layer; as well as The exposed portion of the material layer is etched. 15 . The method of claim 14 , wherein forming the hard mask layer comprises performing a heat treatment at 100° C. to 1,000° C.

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