Hardmask compositions and methods of forming patterns

Abstract

The present invention relates to a hard mask composition comprising a polymer including a moiety derived from a compound represented by Chemical Formula 1 and a solvent, and a method of forming a pattern using the same. In Chemical Formula 1, X 1 to X 3 , A 1 to A 3 , and L 1 to L 3 are defined as set forth in the specification.[Chemical Formula 1]

Description

[0001] [CROSS-REFERENCE TO RELATED APPLICATIONS]

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0181154, filed on December 22, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. TECHNICAL FIELD

[0003] A hard mask composition and a method of forming a pattern using the same are disclosed. BACKGROUND

[0004] Recently, the semiconductor industry has developed to ultra-fine technology having a pattern of several nanometers to several tens of nanometers in size. Such ultra-fine technology essentially requires an effective photolithography technology.

[0005] A typical photolithography technology involves forming a material layer on a semiconductor substrate, coating a photoresist layer on the material layer, performing exposure and development to form a photoresist pattern, and then etching the material layer using the photoresist pattern as a mask.

[0006] Nowadays, while a pattern needs to be formed in a small size, it is not easy to provide a fine pattern having an excellent profile only by the above-described typical photolithography technology. Therefore, an auxiliary layer called a hard mask layer can be formed between the material layer and the photoresist layer to provide a fine pattern. SUMMARY

[0007] Embodiments provide a hard mask composition including a polymer, which can be effectively applied to a hard mask layer.

[0008] Another embodiment provides a method of forming a pattern using the hard mask composition.

[0009] According to embodiments, a hard mask composition including a polymer and a solvent is provided, the polymer including a moiety derived from a compound represented by Chemical Formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In Chemical Formula 1,

[0013] X 1 to X 3 each independently is N or CR a wherein R ais hydrogen, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C30 alkenyl, a substituted or unsubstituted C2 to C30 alkynyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0014] A 1 to A 3 each independently is a substituted or unsubstituted C2 to C40 heterocyclic ring, and

[0015] L 1 to L 3 each independently is a single bond, a substituted or unsubstituted C6 to C30 arylene, or a combination thereof.

[0016] X 1 to X 3 may be the same.

[0017] A 1 to A 3 may each independently include a five-membered heterocyclic ring including a nitrogen atom.

[0018] A 1 to A 3 may each independently be a fused ring.

[0019] The compound represented by Chemical Formula 1 can be represented by Chemical Formula 2.

[0020] [Chemical Formula 2]

[0021]

[0022] In Chemical Formula 2,

[0023] X 1 to X 3 each independently is N or CR a , wherein R a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C30 alkenyl, a substituted or unsubstituted C2 to C30 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a substituted or unsubstituted C2 to C40 heterocyclic ring,

[0024] B 1 to B 6 each independently is a C6 to C30 aromatic ring,

[0025] L 1 to L 3 each independently is a single bond, a substituted or unsubstituted C6 to C30 arylene, or a combination thereof,

[0026] R 1to R 3 each independently is a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C30 alkenyl, a substituted or unsubstituted C2 to C30 alkynyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0027] m 1 to m 6 each independently is 0 or 1, and

[0028] n 1 to n 3 each independently is an integer from 0 to 4.

[0029] B 1 to B 6 may each independently be selected from any one of Group 1.

[0030] [Group 1]

[0031]

[0032] L 1 to L 3 may each independently be a single bond, a substituted or unsubstituted phenylene, or a divalent group comprising a substituted or unsubstituted phenyl moiety bonded by a single bond.

[0033] L 1 to L 3 may each independently be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted quaterphenylene, or a substituted or unsubstituted quinquephenylene.

[0034] L 1 to L 3 may each independently be represented by Chemical Formula 3.

[0035] [Chemical Formula 3]

[0036]

[0037] in Chemical Formula 3,

[0038] l is an integer from 0 to 4,

[0039] * is a point of attachment to other moieties in the compound represented by Chemical Formula 1.

[0040] m 1 and m 2 at least one of m 3 and m 4at least one of m and n can be 1, and m 5 at least one of m and n can be 1. 6 at least one of m and n can be 1.

[0041] The compound represented by Chemical Formula 1 can be represented by any one of Chemical Formula 4 to Chemical Formula 6.

[0042] [Chemical Formula 4]

[0043]

[0044] [Chemical Formula 5]

[0045]

[0046] [Chemical Formula 6]

[0047]

[0048] In Chemical Formula 4 to Chemical Formula 6,

[0049] X 1 to X 3 each independently is N or CR a , wherein R a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C30 alkenyl, a substituted or unsubstituted C2 to C30 alkynyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,

[0050] R 1 to R 3 each independently is a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C30 alkenyl, a substituted or unsubstituted C2 to C30 alkynyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof, and

[0051] l 1 to l 3 and n 1 to n 3 each independently is an integer of 0 to 4.

[0052] The compound represented by Chemical Formula 1 can be a first compound.

[0053] The polymer can include structural units obtained by reaction of a reaction mixture including: a first compound; and a second compound different from the first compound and including at least one carbonyl moiety, an ether moiety, or a combination thereof.

[0054] The second compound can include

[0055] at least one aldehyde group; or

[0056] at least two alkyl groups, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C2 to C30 alkenyloxy, substituted or unsubstituted C2 to C30 alkynyloxy, or a combination thereof.

[0057] The second compound can be represented by Chemical Formula 7 or Chemical Formula 8.

[0058] [Chemical Formula 7]

[0059]

[0060] In Chemical Formula 7,

[0061] A is hydrogen, a substituted or unsubstituted C6 to C40 aromatic ring, a substituted or unsubstituted C2 to C30 heterocyclic ring, or a combination thereof.

[0062] [Chemical Formula 8]

[0063]

[0064] In Chemical Formula 8,

[0065] D is a substituted or unsubstituted C6 to C40 aromatic ring, and

[0066] R 4 and R 5 are each independently a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C30 alkenyl, a substituted or unsubstituted C2 to C30 alkynyl, or a combination thereof.

[0067] A can be hydrogen or a substituted or unsubstituted one selected from Group 2.

[0068] [Group 2]

[0069]

[0070] In Group 2,

[0071] Y 1 and Y 2 are each independently hydrogen, C6 to C30 aryl, C2 to C30 heterocyclyl, or a combination thereof,

[0072] Z 1 to Z 5 are each independently a C6 to C30 aromatic ring, and

[0073] W 1 and W 2 are each independently BR b, NR c , O, S, PR d or P(=O)R e wherein R b through R e are each independently hydrogen, C1to C30alkyl, C2to C30alkenyl, C2to C30alkynyl, C1to C30heteroalkyl, C3to C30cycloalkyl, C3to C30cycloalkenyl, C6to C30aryl, C2to C30heterocyclyl, or combinations thereof.

[0074] D can be one substituted or unsubstituted selected from Group 3.

[0075] [Group 3]

[0076]

[0077] In Group 3,

[0078] W is a single bond, oxygen (-O-), sulfur (-S-), -SO2-, substituted or unsubstituted vinylene, carbonyl (-C(=O)-), CR g R h , NR i or combinations thereof, wherein R g through R i are each independently hydrogen, halogen, carboxyl, substituted or unsubstituted C2to C30oxoalkyl, substituted or unsubstituted C1to C30alkoxycarbonyl, substituted or unsubstituted C1to C30alkoxy, substituted or unsubstituted C1to C10alkyl, substituted or unsubstituted C1to C30alkenyl, substituted or unsubstituted C1to C30alkynyl, substituted or unsubstituted C1to C30heteroalkyl, substituted or unsubstituted C3to C30cycloalkyl, substituted or unsubstituted C3to C30cycloalkenyl, substituted or unsubstituted C6to C30aryl, substituted or unsubstituted C3to C30heterocyclyl, or combinations thereof,

[0079] p is an integer from 1 to 30, and

[0080] * is a point of attachment to other moieties in the second compound represented by Chemical Formula 8.

[0081] R 4 and R 5each independently can be a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted hexyl group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted propenyl group, a substituted or unsubstituted butenyl group, a substituted or unsubstituted pentenyl group, a substituted or unsubstituted hexenyl group, a substituted or unsubstituted ethynyl group, a substituted or unsubstituted propynyl group, a substituted or unsubstituted butynyl group, a substituted or unsubstituted pentynyl group, a substituted or unsubstituted hexynyl group, or a combination thereof.

[0082] The reaction mixture can further include a third compound different from the first compound and the second compound, and including a substituted or unsubstituted C6 to C40 aromatic ring, a substituted or unsubstituted C2 to C30 heterocyclic ring, or a combination thereof.

[0083] The third compound can include a substituted or unsubstituted C6 to C40 aromatic ring substituted with at least one hydroxyl group, an amine group, a substituted or unsubstituted C1 to C30 alkoxy group, or a combination thereof.

[0084] According to another embodiment, a method of forming a pattern includes: applying a hard mask composition on a material layer and heat-treating the resultant 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.

[0085] The solubility of the polymer and the etch resistance of the hard mask layer can be simultaneously ensured. DETAILED DESCRIPTION

[0086] Hereinafter, exemplary embodiments of the disclosure will be set forth in detail, and can be easily performed by those skilled in the art. However, the disclosure can be implemented in many different forms, and is not considered to be limited to the exemplary embodiments described herein.

[0087] "Substituted" as used herein, when not otherwise defined, means that a hydrogen atom of a compound is replaced with a substituent selected from deuterium, a halogen atom (F, Br, CI, or I), a hydroxyl group, a nitro group, a cyano group, an amino group, an azido group, a guanidinyl group, a hydrazine group, a hydrazono group, a carbonyl group, a carboxamide group, a thiol group, an ester group, a carboxyl group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C1to C30alkyl group, a C2to C30alkenyl group, a C2to C30alkynyl group, a C6to C30aryl group, a C7to C30arylalkyl group, a C1to C30alkoxy group, a C1to C20heteroalkyl group, a C3to C20heteroarylalkyl group, a C3to C30cycloalkyl group, a C3to C15cycloalkenyl group, a C6to C15cycloalkynyl group, a C2to C30heterocyclyl group, and combinations thereof.

[0088] Additionally, adjacent two substituents of a substituted hydroxyl group, a nitro group, a cyano group, an amino group, an azido group, a guanidinyl group, a hydrazine group, a hydrazono group, a carbonyl group, a carboxamide group, a thiol group, an ester group, a carboxyl group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C1to C30alkyl group, a C2to C30alkenyl group, a C2to C30alkynyl group, a C6to C30aryl group, a C7to C30arylalkyl group, a C1to C30alkoxy group, a C1to C30heteroalkyl group, a C3to C30heteroarylalkyl group, a C3to C30cycloalkyl group, a C3to C15cycloalkenyl group, a C6to C15cycloalkynyl group, and a C2to C30heterocyclyl group can be fused to form a ring. For example, a substituted C6to C30aryl group can be fused with another adjacent substituted C6to C30aryl group to form a substituted or unsubstituted fluorene ring.

[0089] "Hetero" as used herein means one to three heteroatoms selected from N, O, S, Se, and P.

[0090] Unless otherwise defined herein, "heteroalkyl" can have the concept including alkyl groups including ether moieties, and can include, for example, alkyl groups substituted with alkoxy, and specifically methoxymethoxy, methoxyethoxy, methoxypropoxy, methoxybutoxy, ethoxymethoxy, ethoxyethoxy, ethoxypropoxy, ethoxybutoxy, propoxymethoxy, propoxyethoxy, propoxypropoxy, propoxybutoxy, butoxymethoxy, butoxyethoxy, butoxypropoxy, or butoxybutoxy.

[0091] "Aryl" as used herein means a group comprising at least one hydrocarbon aromatic moiety, and includes hydrocarbon aromatic moieties connected by single bonds and directly or annularly fused to provide non-aromatic fused rings. Aryl groups can include monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) functional groups.

[0092] As used herein, the term "heterocyclic group" includes heteroaryl groups and may include at least one heteroatom selected from N, O, S, P, and Si to replace carbon (C) in a cyclic compound, such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0093] More specifically, the substituted or unsubstituted aryl group 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 fluorenyl group, a substituted or unsubstituted naphthacene 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 The present invention may be a fused ring of a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenyl group, a combination thereof, or a combination of the foregoing groups, but is not limited thereto.

[0094] More specifically, the substituted or unsubstituted heterocyclic group may be a substituted or unsubstituted furyl 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 pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridoindoleyl, substituted or unsubstituted benzopyridoxazinyl, substituted or unsubstituted benzopyridothiazolyl, substituted or unsubstituted 9,9-dimethyl-9,10-dihydroacridinyl, combinations thereof, or fused rings of combinations of the foregoing groups, but are not limited thereto.

[0095] As used herein, the term "combination" refers to a mixture or copolymerization when not otherwise specifically defined.

[0096] As used herein, the term "polymer" is intended to include oligomers and polymers.

[0097] Hereinafter, a hard mask composition according to an embodiment is set forth.

[0098] A hard mask composition according to an embodiment includes a polymer and a solvent.

[0099] The polymer can include a moiety derived from a compound including a core that is an aromatic ring or a heterocyclic ring, and a plurality of substituents substituted on the core and including a heterocyclic ring. The core can be a hexagonal ring, for example, a benzene ring or a hexagonal heterocyclic ring including at least one nitrogen atom. Since the compound including the moiety includes an aromatic ring and / or a heterocyclic ring having a high carbon content in both the core and the substituents, the polymer including the moiety derived from the compound can form a hard layer, thereby resulting in imparting high corrosion resistance.

[0100] For example, the plurality of substituents substituted on the core and including a heterocyclic ring can include a heterocyclic ring at a terminal end, and the number of substituents can be three. Accordingly, stacking interactions between polymers can be prevented, and attractive forces between polymers can be reduced, thereby the solubility of the polymer can be improved.

[0101] For example, the polymer can include a moiety derived from a compound represented by Chemical Formula 1.

[0102] [Chemical Formula 1]

[0103]

[0104] In Chemical Formula 1,

[0105] X 1 to X 3 each independently is N or CR a wherein R a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C30 alkenyl, a substituted or unsubstituted C2 to C30 alkynyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,

[0106] A 1 to A 3 each independently is a substituted or unsubstituted C2 to C40 heterocyclic ring, and

[0107] L 1 to L 3each independently is a single bond, a substituted or unsubstituted C6 to C30 arylene, or a combination thereof.

[0108] For example, X 1 to X 3 may be the same. For example, X 1 to X 3 may be N, or X 1 to X 3 may be CR a .

[0109] For example, R a may be hydrogen.

[0110] For example, A 1 to A 3 may include a five-membered heterocycle, and for example, A 1 to A 3 may each independently include a five-membered heterocycle including a nitrogen atom.

[0111] For example, A 1 to A 3 may each independently be a monocyclic or polycyclic ring, and for example, the polycyclic ring can be a fused ring.

[0112] In particular, A 1 to A 3 may each independently be a substituted or unsubstituted pyrrole, a substituted or unsubstituted indole, a substituted or unsubstituted carbazole, but are not limited thereto.

[0113] For example, A 1 to A 3 may be the same as or different from each other, but A 1 to A 3 may desirably be the same.

[0114] For example, in the definition of L 1 to L 3 , the substituted or unsubstituted C6 to C30 arylene can be a divalent non-fused aromatic ring group, a divalent fused aromatic ring group, a divalent group in which aromatic moieties are connected by a single bond, a divalent group in which each ring fused to two non-parallel sides of a benzene ring is fused, a divalent group in which each ring fused to two non-parallel sides of a benzene ring is connected by a single bond or a double bond, or a combination thereof.

[0115] For example, L 1 to L 3Each of the groups may independently be a single bond, a substituted or unsubstituted phenylene group, or a divalent group comprising a substituted or unsubstituted benzene moiety bonded via a single bond. This ensures high rotational freedom in the compound, and by ensuring high rotational freedom, it can be more efficiently applied to solution processes such as spin coating. Furthermore, since the aromatic and heterocyclic rings with high carbon contents are linked via a single bond, the carbon content of the polymer can be increased to form a hard layer, thereby imparting higher corrosion resistance.

[0116] For example, L 1 to L 3 and substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted quaterphenylene, or substituted or unsubstituted pentphenylene.

[0117] For example, L 1 to L 3 and substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted p-terphenylene, substituted or unsubstituted p-quaterphenylene, or substituted or unsubstituted p-pentaphenylene.

[0118] Specifically, L 1 to L 3 can be each independently represented by Chemical Formula 3.

[0119] [Chemical Formula 3]

[0120]

[0121] In Chemical Formula 3,

[0122] l is an integer from 0 to 4, and

[0123] * is a connection point with other parts in the compound represented by Chemical Formula 1.

[0124] For example, l can be an integer from 0 to 2, such as 0 or 1.

[0125] For example, L 1 to L 3 can be the same or different from each other, but L 1 to L 3 Desirably the same.

[0126] For example, the compound represented by Chemical Formula 1 may be represented by Chemical Formula 2.

[0127] [Chemical Formula 2]

[0128]

[0129] In Chemical Formula 2,

[0130] X 1 to X 3 and L 1 to L 3 each are the same as described above,

[0131] B 1 to B 6 each independently is a C6 to C30 aromatic ring,

[0132] R 1 to R 3 each independently is a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C30 alkenyl, a substituted or unsubstituted C2 to C30 alkynyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0133] m 1 to m 6 each independently is 0 or 1, and

[0134] n 1 to n 3 each independently is an integer from 0 to 4.

[0135] For example, B 1 to B 6 may each independently be a benzene ring; a fused ring in which two or more aromatic rings are fused; or a non-fused ring in which two or more aromatic rings are connected by a single bond.

[0136] For example, B 1 to B 6 may each independently be selected from any one of Group 1.

[0137] [Group 1]

[0138]

[0139] For example, B 1 to B 6 may be the same as or different from each other, and for example, B 1 to B 6 may be the same.

[0140] For example, B 1 to B 6 may each independently be benzene.

[0141] For example, at least one of m 1 and m 2 may be 1, m3 and m 4 At least one of can be 1, and m 5 and m 6 At least one of can be 1.

[0142] For example, m 1 and m 2 Can be 1, m 3 and m 4 Can be 1, and m 5 and m 6 Can be 1.

[0143] For example, m 1 to m 6 The owner of can all be 1.

[0144] For example, m 1 to m 6 The owner in can all be 0.

[0145] For example, n 1 to n 3 may each independently be an integer from 0 to 2, such as 0 or 1.

[0146] For example, n 1 to n 3 Can be the same or different from each other, but n 1 to n 3 may desirably be the same, for example, n 1 to n 3 The owner in can all be 0.

[0147] For example, the compound represented by Chemical Formula 1 may be represented by any one of Chemical Formulas 4 to 6.

[0148] [Chemical Formula 4]

[0149]

[0150] [Chemical Formula 5]

[0151]

[0152] [Chemical Formula 6]

[0153]

[0154] In Chemical Formulas 4 to 6,

[0155] X 1 to X 3 、R 1 to R 3 and n 1 to n3 each is the same as described above, and

[0156] l 1 to l 3 each independently is an integer from 0 to 4.

[0157] For example, l 1 to l 3 may each independently be an integer from 0 to 2, such as 0 or 1.

[0158] For example, l 1 to l 3 may be the same as or different from each other, but l 1 to l 3 may desirably be the same.

[0159] Hereinafter, the compound represented by Chemical Formula 1 is also referred to as a first compound.

[0160] The polymer can further include a moiety derived from a second compound different from the first compound and including at least one carbonyl moiety, ether moiety, or a combination thereof.

[0161] As one example, the polymer can include a structural unit obtained by reaction of a reaction mixture including: a first compound; and a second compound different from the first compound and including an organic group including at least one oxygen atom.

[0162] The organic group including at least one oxygen atom can be an organic group including at least one carbonyl moiety, ether moiety, or a combination thereof. Herein, the organic group including a carbonyl moiety can include, for example, a ketone group, aldehyde group, ester group, amide group, acyl group, carboxyl group, carbamate group, carbonate group, or a combination thereof; and the organic group including an ether moiety can include, for example, an alkyl group substituted with alkoxy, alkenoxy, alkynoxy, or a combination thereof.

[0163] For example, the second compound can include at least one aldehyde group; alkyl group substituted with alkoxy, alkenoxy, alkynoxy, or a combination thereof; or a combination thereof. Thus, the second compound can react with the first compound (and / or a third compound to be described later) to be bonded to form a secondary carbon, tertiary carbon, quaternary carbon, or a combination thereof, and in particular, the second compound can be bonded to form a secondary carbon, tertiary carbon, or a combination thereof. Herein, a secondary carbon is defined as a central carbon where two of the four bonds are each bonded to other carbons; a tertiary carbon is defined as a central carbon where three of the four bonds are each bonded to other carbons; and a quaternary carbon is defined as a central carbon where all four bonds are bonded to other carbons.

[0164] Accordingly, by further increasing the solubility in the solvent without deteriorating the excellent etch resistance of the polymer, the polymer can be prepared into a solution and effectively formed into a polymer layer by a solution process (e.g., spin coating). In addition, due to its high etch resistance, the formed polymer layer can reduce or prevent damage from an etching gas exposed in a subsequent etching process.

[0165] For example, the second compound can include at least one aldehyde group; or

[0166] may include at least two alkyl groups substituted with a substituted or unsubstituted C1 to C30 alkoxy, a substituted or unsubstituted C2 to C30 alkenyloxy, a substituted or unsubstituted C2 to C30 alkynyloxy, or a combination thereof.

[0167] For example, the second compound can include only one aldehyde group; or can include two alkyl groups substituted with a substituted or unsubstituted C1 to C30 alkoxy, a substituted or unsubstituted C2 to C30 alkenyloxy, a substituted or unsubstituted C2 to C30 alkynyloxy, or a combination thereof.

[0168] For example, the second compound can be represented by Chemical Formula 7 or Chemical Formula 8.

[0169] [Chemical Formula 7]

[0170]

[0171] In Chemical Formula 7,

[0172] A is hydrogen, a substituted or unsubstituted C6 to C40 aromatic ring, a substituted or unsubstituted C2 to C30 heterocyclic ring, or a combination thereof;

[0173] [Chemical Formula 8]

[0174]

[0175] In Chemical Formula 8,

[0176] D is a substituted or unsubstituted C6 to C40 aromatic ring, and

[0177] R 4 and R 5 are each independently a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C30 alkenyl, a substituted or unsubstituted C2 to C30 alkynyl, or a combination thereof.

[0178] The aromatic ring can be a benzene ring; a fused ring in which two or more aromatic rings are fused; or a non-fused ring in which two or more aromatic rings are connected by a single bond, a C1 to C5 alkylene, O, C(=O), or OC(=O).

[0179] A heterocycle is a monocycle comprising at least one heteroatom; a fused ring fused with two or more rings comprising at least one heteroatom; the rings comprising two or more at least one heteroatom can be non-fused rings connected by a single bond, C1 to C5 alkylene, O, C(=O), or OC(=O).

[0180] The substituted or unsubstituted C1 to C30 alkyl can be, for example, substituted or unsubstituted C1 to C20 alkyl, for example, substituted or unsubstituted C1 to C15 alkyl, for example, substituted or unsubstituted C1 to C10 alkyl, for example, substituted or unsubstituted C1 to C6 alkyl, for example, substituted or unsubstituted C1 to C4 alkyl, or a combination thereof. Specifically, the substituted or unsubstituted C1 to C30 alkyl can be substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted nonyl, substituted or unsubstituted decyl, or a combination thereof, but is not limited thereto.

[0181] The substituted or unsubstituted C2 to C20 alkenyl can be, for example, substituted or unsubstituted C2 to C15 alkenyl, for example, substituted or unsubstituted C2 to C10 alkenyl, for example, substituted or unsubstituted C2 to C8 alkenyl, or a combination thereof. Specifically, the substituted or unsubstituted C2 to C20 alkenyl can be substituted or unsubstituted ethenyl, substituted or unsubstituted propenyl, substituted or unsubstituted butenyl, substituted or unsubstituted pentenyl, substituted or unsubstituted hexenyl, substituted or unsubstituted heptenyl, substituted or unsubstituted octenyl, substituted or unsubstituted nonenyl, substituted or unsubstituted decenyl, or a combination thereof, but is not limited thereto.

[0182] The substituted or unsubstituted C2 to C20 alkynyl can be, for example, substituted or unsubstituted C2 to C15 alkynyl, for example, substituted or unsubstituted C2 to C10 alkynyl, for example, substituted or unsubstituted C2 to C8 alkynyl, or a combination thereof. Specifically, the substituted or unsubstituted C2 to C20 alkynyl can be substituted or unsubstituted ethynyl, substituted or unsubstituted propynyl, substituted or unsubstituted butynyl, substituted or unsubstituted pentynyl, substituted or unsubstituted hexynyl, substituted or unsubstituted heptynyl, substituted or unsubstituted octynyl, substituted or unsubstituted nonynyl, substituted or unsubstituted decynyl, or a combination thereof, but is not limited thereto.

[0183] For example, A can be a polycyclic ring, wherein the polycyclic ring can be a non-fused ring, a fused ring, or a combination thereof, but desirably a fused ring. Thus, a layer made of the polymer can provide a higher etch resistance to an etching gas.

[0184] For example, A can be one selected from Group 2, which is substituted or unsubstituted.

[0185] [Group 2]

[0186]

[0187] In Group 2,

[0188] Y 1 and Y 2 each independently is hydrogen, C6 to C30 aryl, C2 to C30 heterocyclyl, or a combination thereof,

[0189] Z 1 to Z 5 each independently is a C6 to C30 aromatic ring, and

[0190] W 1 and W 2 each independently is BR b , NR c , O, S, PR d , or P(=O)R e , wherein R b to R e each independently is hydrogen, C1 to C30 alkyl, C2 to C30 alkenyl, C2 to C30 alkynyl, C1 to C30 heteroalkyl, C3 to C30 cycloalkyl, C3 to C30 cycloalkenyl, C6 to C30 aryl, C2 to C30 heterocyclyl, or a combination thereof.

[0191] In Group 2, each moiety can be unsubstituted or substituted with one or more substituents. Herein, the substituents can be, for example, deuterium, halogen, hydroxyl, amino, carboxyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C1 to C30 alkylamino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C2 to C30 alkynyl, substituted or unsubstituted C1 to C30 heteroalkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof, but are not limited thereto.

[0192] For example, Y 1 and Y 2may each independently be hydrogen, phenyl, naphthyl, anthryl, phenanthryl, tetracenyl, pyrenyl, biphenyl, terphenyl, quaterphenyl, a combination thereof, or a combination of the foregoing fused rings, but are not limited thereto.

[0193] For example, Y 1 to Y 2 may be the same as or different from each other.

[0194] For example, Z 1 to Z 5 may each independently be benzene, naphthalene, anthracene, phenanthrene, fluorene, fluoranthene, acenaphthylene, acenaphthene, benzophenanthrene, pyrene, triphenylene, tetracene, benzofluoranthene, perylene, benzo pyrene, naphthanthrene, pentacene, benzoperylene, diphenylene, chrysene, or a combination thereof.

[0195] For example, Z 1 to Z 5 may be the same as or different from each other.

[0196] For example, Z 1 to Z 2 may be the same as or different from each other, and Z 4 to Z 5 may be the same as or different from each other.

[0197] For example, R b to R e may each independently be hydrogen or C1 to C30 alkyl, wherein the C1 to C30 alkyl is the same as described above.

[0198] For example, D can be one substituted or unsubstituted selected from Group 3. In the definition of Group 3, “substituted” means that it is further substituted with another substituent, and “unsubstituted” means that it is not further substituted with another substituent.

[0199] [Group 3]

[0200]

[0201] In Group 3,

[0202] W is a single bond, oxygen (-O-), sulfur (-S-), -SO2-, substituted or unsubstituted vinylene, carbonyl (-C(=O)-), CR g R h , NR i or a combination thereof, wherein R g to R ieach independently hydrogen, halogen, carboxyl, substituted or unsubstituted C2 to C30 oxoalkyl, substituted or unsubstituted C1 to C30 alkoxycarbonyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C30 alkenyl, substituted or unsubstituted C1 to C30 alkynyl, substituted or unsubstituted C1 to C30 heteroalkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C3 to C30 cycloalkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, or a combination thereof,

[0203] p is an integer from 1 to 30, and

[0204] * is a point of attachment to other moieties in the compound represented by Chemical Formula 8.

[0205] For example, p can be an integer from 1 to 20, such as an integer from 1 to 10, such as an integer from 1 to 5, such as an integer from 1 to 3, or such as 1 or 2.

[0206] For example, R 4 and R 5 may each independently be substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted ethenyl, substituted or unsubstituted propenyl, substituted or unsubstituted butenyl, substituted or unsubstituted pentenyl, substituted or unsubstituted hexenyl, substituted or unsubstituted ethynyl, substituted or unsubstituted propynyl, substituted or unsubstituted butynyl, substituted or unsubstituted pentynyl, substituted or unsubstituted hexynyl, or a combination thereof.

[0207] Without wishing to be bound by a particular theory, the moiety derived from the aforementioned second compound can be represented by Chemical Formula 9.

[0208] [Chemical Formula 9]

[0209]

[0210] In Chemical Formula 9,

[0211] Ar 1 is a divalent organic group comprising a substituted or unsubstituted C6 to C30 aromatic ring,

[0212] R 11 to R 14each independently hydrogen, deuterium, halogen, nitro, amino, hydroxyl, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof,

[0213] R 11 and R 12 each independently exist or are linked to each other to form a ring,

[0214] R 13 and R 14 each independently exist or are linked to each other to form a ring,

[0215] p 1 is 0 or 1, q 1 is an integer from 0 to 3, and

[0216] * is a point of attachment to other moieties in the polymer.

[0217] In the above definitions of Ar 1 , the aromatic ring can be a benzene ring; a fused ring in which two or more aromatic rings are fused; or a non-fused ring in which two or more aromatic rings are linked by a single bond, C1 to C5 alkylene, O, C(=O), or OC(=O).

[0218] For example, Ar 1 may be any one selected from the above Group 3, which is substituted or unsubstituted.

[0219] For example, at least two of R 11 to R 14 may be hydrogen, substituted or unsubstituted C6 to C30 aryl, or a combination thereof; for example, at least one of R 11 and R 12 may be hydrogen, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and at least one of R 13 and R 14 may be hydrogen, substituted or unsubstituted C6 to C30 aryl, or a combination thereof; or for example, R 11 to R 14 may each independently be hydrogen, substituted or unsubstituted C6 to C30 aryl, or a combination thereof. Herein, the substituted or unsubstituted C6 to C30 aryl is the same as described above.

[0220] For example, at least two of R 11 to R 14 may be hydrogen; or for example, at least one of R 11 and R 12 may be hydrogen, and at least one of R 13 and R 14 may be hydrogen. For example, R 11 to R14 The owner of each of them can be hydrogen.

[0221] For example, R 11 to R 14 Both of them may be hydrogen, and R 11 to R 14 The other two in R may be substituted or unsubstituted C6 to C30 aryl groups; for example, R 11 and R 12 One of them may be hydrogen, and R 11 and R 12 The other of may be a substituted or unsubstituted C6 to C30 aryl group, and R 13 and R 14 One of them may be hydrogen, and R 13 and R 14 The other of may be a substituted or unsubstituted C6 to C30 aryl group. Herein, the substituted or unsubstituted C6 to C30 aryl group is the same as described above.

[0222] For example, R 11 to R 14 At least two of the R 11 and R 12 At least one of them may be a substituted or unsubstituted C6 to C30 aryl group, and R 13 and R 14 At least one of may be a substituted or unsubstituted C6 to C30 aryl group. For example, R 11 to R 14 The owner in may be a substituted or unsubstituted C6 to C30 aryl group. Herein, the substituted or unsubstituted C6 to C30 aryl group is the same as described above.

[0223] For example, R 11 to R 14 can be the same or different from each other, for example, R 11 With R 12 may be the same or different from each other, and R 13 With R 14 They may be the same as or different from each other.

[0224] For example, R 11 and R 12 may exist independently of each other or may be combined with each other to form a ring, and R 13 and R 14 They may exist independently of each other or may be combined with each other to form a ring.

[0225] For example, q 1 It can be an integer from 0 to 2, and q1 may be 0 or 1.

[0226] when q 1 is an integer of 2 or more, the plurality of R 13 may be the same as or different from each other, and the plurality of R 14 may be the same as or different from each other.

[0227] For example, q 1 and p 1 may both be 0, and q 1 and p 1 may both be 1.

[0228] For example, Chemical Formula 9 can be represented by Chemical Formula 9-1 or Chemical Formula 9-2.

[0229] [Chemical Formula 9-1]

[0230]

[0231] [Chemical Formula 9-2]

[0232]

[0233] In Chemical Formula 9-1 and Chemical Formula 9-2, Ar 1 , R 11 to R 14 and * are the same as described above.

[0234] For example, Chemical Formula 9 can be one substituted or unsubstituted selected from Group A, but is not limited thereto.

[0235] [Group A]

[0236]

[0237] In the definition of Group A, "substituted" means that it is further substituted with another substituent, and "unsubstituted" means that it is not further substituted with another substituent.

[0238] The aforementioned polymer can further include a moiety derived from a third compound different from the first compound and the second compound and including a substituted or unsubstituted C6 to C40 aromatic ring, a substituted or unsubstituted C2 to C30 heterocyclic ring, or a combination thereof. Accordingly, the carbon content of the polymer can be further increased to form a hard polymer layer, thereby providing higher etch resistance.

[0239] For example, the foregoing reaction mixture can further include a third compound that is different from the foregoing first and second compounds and includes a substituted or unsubstituted C6to C40aromatic ring, a substituted or unsubstituted C2to C30heterocycle, or a combination thereof. The C6to C40aromatic ring and the substituted or unsubstituted C2to C30heterocycle can each be the same as described above.

[0240] For example, the third compound can include a polycyclic ring, where the polycyclic ring can be a non-fused ring, a fused ring, or a combination thereof, but desirably a fused ring. As a result, the layer made from the polymer can be imparted with a higher etch resistance to an etching gas.

[0241] For example, the third compound can include a substituted or unsubstituted naphthalene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted anthracene, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted benzanthracene, a substituted or unsubstituted fluoranthene, a substituted or unsubstituted acenaphthylene, a substituted or unsubstituted acenaphthene, a substituted or unsubstituted benzophenanthrene, a substituted or unsubstituted pyrene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted a substituted or unsubstituted benzofluoranthene, a substituted or unsubstituted perylene, a substituted or unsubstituted benzopyrene, a substituted or unsubstituted naphthanthrene, a substituted or unsubstituted pentacene, a substituted or unsubstituted benzo[ghi]perylene, a substituted or unsubstituted dibenzo[a,c]pyrene, a substituted or unsubstituted diphenylfluorene, a substituted or unsubstituted dinaphthylfluorene, a substituted or unsubstituted pyrrole, a substituted or unsubstituted imidazole, a substituted or unsubstituted indole, a substituted or unsubstituted carbazole, a substituted or unsubstituted benzimidazole, or a combination thereof.

[0242] For example, the third compound can include a substituted or unsubstituted C6to C40aromatic ring that is substituted with at least one hydroxyl group, an amine group, a substituted or unsubstituted C1to C30alkoxy group, or a combination thereof; or a substituted or unsubstituted C2to C30heterocycle that is substituted with at least one hydroxyl group, an amine group, a substituted or unsubstituted C1to C30alkoxy group, or a combination thereof.

[0243] For example, the third compound can include only a substituted or unsubstituted C6to C30aromatic ring that is substituted with a hydroxyl group, an amine group, a substituted or unsubstituted C1to C30alkoxy group, or a combination thereof; or can include only a substituted or unsubstituted C2to C30heterocycle that is substituted with a hydroxyl group, an amine group, a substituted or unsubstituted C1to C30alkoxy group, or a combination thereof.

[0244] Accordingly, it can be effectively applied to a solution process (e.g., spin coating) by increasing the solubility in a solvent, and can form a hard polymer layer by increasing the carbon content, thereby providing high etch resistance.

[0245] For example, at least one of the first compound, the second compound, and the third compound can include a fused ring; for example, at least one of the second compound and the third compound can include a fused ring; for example, both the second compound and the third compound can include a fused ring; or for example, all of the first compound, the second compound, and the third compound can include a fused ring.

[0246] For example, the content of the first compound can be about 5 mol% to 50 mol%, desirably about 10 mol% to 45 mol%, or about 20 mol% to 40 mol%, based on the total number of moles of the first compound, the second compound, and the third compound in the mixture forming the polymer.

[0247] For example, the content of the second compound can be about 20 mol% to about 90 mol%, desirably about 30 mol% to about 85 mol%, or about 40 mol% to 75 mol%, based on the total number of moles of the first compound, the second compound, and the third compound in the mixture forming the polymer.

[0248] For example, the content of the third compound can be about 5 mol% to about 50 mol%, desirably about 10 mol% to about 40 mol%, or about 15 mol% to about 30 mol%, based on the total number of moles of the first compound, the second compound, and the third compound in the mixture forming the polymer.

[0249] The polymer can be synthesized by a condensation reaction using the first compound, the second compound, and the third compound as reactants. For example, the polymer can be synthesized by first condensing the first compound and the second compound, and then performing a condensation reaction of the third compound. For example, the first compound and the second compound first undergo a condensation reaction, and then the third compound and the second compound alternately perform a condensation reaction, but the present disclosure is not limited thereto.

[0250] The polymer can include one or more of the aforementioned structural units, and each of the plurality of aforementioned structural units can have the same structure or a different structure, and the number and arrangement of the aforementioned structural units included in the polymer are not limited.

[0251] In the polymer according to the embodiment, a plurality of moieties derived from the aforementioned first compound can be included, a plurality of moieties derived from the aforementioned second compound can be included, and a plurality of moieties derived from the aforementioned third compound can be included. In the aforementioned polymer, the plurality of moieties derived from the aforementioned first compound can be the same as or different from each other, the plurality of moieties derived from the aforementioned second compound can be the same as or different from each other, and the plurality of moieties derived from the aforementioned third compound can be the same as or different from each other.

[0252] The polymer can further include one or two or more structural units different from the aforementioned structural units.

[0253] The polymer can have a weight average molecular weight of about 500 g / mol to about 200,000 g / mol. More specifically, the polymer can have a weight average molecular weight of about 700 g / mol to about 100,000 g / mol, about 800 g / mol to about 50,000 g / mol, or about 900 g / mol to about 10,000 g / mol. When the polymer has a weight average molecular weight within the range, the polymer can be optimized by adjusting the amount of carbon and solubility in a solvent.

[0254] On the other hand, the solvent used in the hard mask composition can be any solvent having sufficient solubility or dispersibility with respect to the polymer, and can include, for example, at least one selected from the group consisting of 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, gamma-butyrolactone, N,N-dimethylformamide, N,N-dimethylacetamide, methylpyrrolidone, methylpyrrolidinone, acetylacetone, and 3-ethoxypropyl acetate, but is not limited thereto.

[0255] The content of the polymer can be about 0.1 wt% to about 60 wt%, about 0.5 wt% to about 50 wt%, about 1 wt% to about 35 wt%, or about 23 wt% to 30 wt%, based on the total amount of the hard mask composition. When the polymer within the range is included, the thickness, surface roughness, and planarization of the hard mask can be controlled.

[0256] The hard mask composition can further include an additive of a surfactant, a crosslinking agent, a thermal acid generator, or a plasticizer.

[0257] The surfactant can include, for example, a fluoroalkyl-based compound, an alkylbenzenesulfonate, an alkylpyridinium salt, a polyethylene glycol, or a quaternary ammonium salt, but is not limited thereto.

[0258] The crosslinking agent can be, for example, a melamine-based, a substituted urea-based, or a polymer-based crosslinking agent. Desirably, the crosslinking agent can be a crosslinking agent having at least two crosslink-forming substituents, such as, for example, methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, or butoxymethylated thiourea, and the like.

[0259] The crosslinking agent can be a crosslinking agent having high heat resistance. The crosslinking agent having high heat resistance can be a compound including a crosslinking substituent containing an aromatic ring (e.g., a benzene ring or a naphthalene ring) in a molecule.

[0260] The thermal acid generator can be, for example, an acidic compound (e.g., p-toluenesulfonic acid, triflic acid, pyridine p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthyl carbonic acid, and the like) or / and 2,4,4,6-tetrabromocyclohexadienone, toluenesulfonic acid benzoin ester, 2-nitrobenzyl toluenesulfonic acid ester, other organic sulfonic acid alkyl esters, and the like, but is not limited thereto.

[0261] The additive can be contained in an amount of about 0.001 parts by weight to 40 parts by weight, about 0.01 parts by weight to 30 parts by weight, or about 0.1 parts by weight to 20 parts by weight, based on 100 parts by weight of the hard mask composition. Within the range, the solubility can be improved, while the optical properties of the hard mask composition are not changed.

[0262] According to another embodiment, an organic film produced using the hard mask composition is provided. The organic film can be formed, for example, by coating the hard mask composition on a substrate and performing a heat treatment on the hard mask composition to cure, and can include, for example, a hard mask layer, a planarization layer, a sacrificial layer, a filler, and the like, for electronic devices.

[0263] Hereinafter, a method of forming a pattern using the aforementioned hard mask composition is described.

[0264] The method of forming a pattern according to the embodiment includes forming a material layer on a substrate, applying a hard mask composition including the aforementioned polymer and a solvent on the material layer, performing a heat treatment on the hard mask composition to form a hard mask layer, forming a photoresist layer on the hard mask layer, performing an exposure and development on 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.

[0265] The substrate can be, for example, a silicon wafer, a glass substrate, or a polymer substrate.

[0266] The material layer is a material to be finally patterned, such as a metal layer (e.g., an aluminum layer and a copper layer), a semiconductor layer (e.g., a silicon layer), or an insulating layer (e.g., a silicon oxide layer and a silicon nitride layer). The material layer can be formed by a method such as a chemical vapor deposition (CVD) process.

[0267] The hard mask composition is the same as described above, and can be applied by spin coating in a solution form. In this context, the thickness of the hard mask composition is not particularly limited, but can be, for example, about to about

[0268] The heat treatment of the hard mask composition can be performed, for example, at about 100°C to about 1000°C for about 10 seconds to about 1 hour.

[0269] For example, the heat treatment of the hard mask composition can include a single heat treatment or multiple heat treatments.

[0270] For example, the heat treatment of the hard mask composition can be performed, for example, at about 100°C to about 1000°C for about 10 seconds to about 1 hour, and for example, the heat treatment can be performed in an atmosphere of air, or nitrogen or oxygen, at a concentration of about 1 wt% or less than 1 wt%.

[0271] For example, the heat treatment of the hard mask composition can successively include a primary heat treatment, for example, at about 100°C to about 1000°C for about 10 seconds to about 1 hour, and a secondary heat treatment, for example, at about 100°C to about 1000°C for about 10 seconds to about 1 hour. For example, the primary heat treatment and the secondary heat treatment can be performed in an atmosphere of air, or nitrogen or oxygen, at a concentration of about 1 wt% or less than 1 wt%.

[0272] For example, the formation of the hard mask layer can include ultraviolet (UV) / visible (Viscuring) and / or near infrared (IR) curing.

[0273] For example, the formation of the hard mask layer can include successively at least one or two or more selected from a primary heat treatment, a secondary heat treatment, UV / Viscuring, and near IR curing.

[0274] For example, the method can further include forming a silicon-containing thin layer on the hard mask layer. The silicon-containing thin layer can be formed of a material such as SiCN, SiOC, SiON, SiOCN, SiC, SiO, and / or SiN.

[0275] For example, the method can further include forming a bottom antireflective coating (BARC) on the upper surface of the silicon-containing thin layer or on the upper surface of the hard mask layer, before forming the photoresist layer.

[0276] Exposure of the photoresist layer can be performed by using, for example, ArF, KrF, or extreme violet (EUV). After exposure, a heat treatment can be performed at about 100°C to about 700°C.

[0277] The etching process of the exposed portion of the material layer can be performed by a dry etching process using an etching gas, and the etching gas can be, for example, CHF3, CF4, Cl2, BCl3, and a mixed gas thereof.

[0278] The etched material layer can be formed into a plurality of patterns, and the plurality of patterns can be metal patterns, semiconductor patterns, insulating patterns, etc., such as a variety of patterns of a semiconductor integrated circuit device.

[0279] Hereinafter, embodiments are illustrated in more detail with reference to examples. However, these examples are exemplary, and the scope of the present claims is not limited thereto.

[0280] Synthesis of polymer

[0281] Synthesis Example 1: Synthesis of Polymer 1

[0282] A tris-carbazolyl benzene represented by Chemical Formula 1a (17.21 g, 0.03 mol), a pyrene carboxaldehyde represented by Chemical Formula 7a (11.51 g, 0.05 mol), p-toluenesulfonic acid monohydrate (p-toluenesulfonic acid monohydrate, 7.61 g, 0.04 mol), and 1,4-dioxane (36.33 g) were put into a 500-ml flask, and stirred at 110°C to perform a reaction. A sample was taken from the polymerization reactant every one hour, and measured with respect to a weight average molecular weight. When the weight average molecular weight reached 4,200 g / mol to 4,500 g / mol, the reaction was quenched. After the polymerization reaction was completed, tetrahydrofuran (10 g), ethyl acetate (70 g), and distilled water (110 g) were added to remove an acid catalyst, and this operation was repeated three times. Subsequently, ethyl acetate (50 g) was added to extract an organic layer, and treated under reduced pressure. Subsequently, tetrahydrofuran (50 g) was added, and the mixture was added to hexane (300 g) to perform precipitation. Then, it was filtered and dried to remove 1,4-dioxane and a remaining monomer, thereby obtaining Polymer 1 (Mw (molecular weight): 4,800 g / mol).

[0283] [Chemical Formula 1a]

[0284]

[0285] [Chemical Formula 7a]

[0286]

[0287] Synthesis Example 2: Synthesis of Polymer 2

[0288] Tri-carbazolyl benzene represented by Chemical Formula 1a (11.47 g, 0.02 mol), pyrene carboxaldehyde represented by Chemical Formula 7a (11.51 g, 0.05 mol), 1-hydroxy pyrene (4.37 g, 0.02 mol), p-toluene sulfonic acid monohydrate (7.61 g, 0.04 mol), and 1,4-dioxane (34.96 g) were put into a 500 ml flask and stirred at 110°C to perform a reaction. A sample was taken from the polymerization reactant every one hour and measured with respect to weight average molecular weight. When the weight average molecular weight reached 3,100 g / mol to 3,300 g / mol, the reaction was quenched. After the polymerization reaction was completed, tetrahydrofuran (10 g), ethyl acetate (70 g), and distilled water (110 g) were added to remove the acid catalyst, and this operation was repeated three times. Subsequently, ethyl acetate (50 g) was added to extract the organic layer and treated under reduced pressure. Then, tetrahydrofuran (50 g) was added and the mixture was added to hexane (300 g) to precipitate, and then, filtered and dried to remove 1,4-dioxane and the remaining monomer, thereby obtaining Polymer 2 (Mw: 3,700 g / mol).

[0289] Synthesis Example 3: Synthesis of Polymer 3

[0290] Indolyl oxy benzene represented by Chemical Formula 1b (12.71 g, 0.03 mol), pyrene carboxaldehyde represented by Chemical Formula 7a (11.51 g, 0.05 mol), p-toluene sulfonic acid monohydrate (7.61 g, 0.04 mol), and 1,4-dioxane (31.83 g) were put into a 500 ml flask and stirred at 110°C to perform a reaction. A sample was taken from the polymerization reactant every one hour and measured with respect to weight average molecular weight. When the weight average molecular weight reached 3,800 g / mol to 4,100 g / mol, the reaction was quenched. After the polymerization reaction was completed, tetrahydrofuran (10 g), ethyl acetate (70 g), and distilled water (110 g) were added to remove the acid catalyst, and this operation was repeated three times. Subsequently, ethyl acetate (50 g) was added to extract the organic layer and treated under reduced pressure. Then, tetrahydrofuran (50 g) was added and the mixture was added to hexane (300 g) to precipitate, and then, filtered and dried to remove 1,4-dioxane and the remaining monomer, thereby obtaining Polymer 3 (Mw: 4,400 g / mol).

[0291] [Chemical Formula 1b]

[0292]

[0293] Synthesis Example 4: Synthesis of Polymer 4

[0294] Tri-carbazolyl benzene (6.88 g, 0.012 mol), tri-indolyl benzene represented by Chemical Formula 1b (5.08 g, 0.012 mol), pyrene carboxaldehyde represented by Chemical Formula 7a (9.21 g, 0.040 mol), p-toluenesulfonic acid monohydrate (6.09 g, 0.032 mol), and 1,4-dioxane (27.26 g) were put into a 500 mL flask, and stirred at 110°C to perform a reaction. Sampling was performed every one hour from the polymerization reactant, and measurement was performed with respect to the weight average molecular weight. After the polymerization reaction was completed, tetrahydrofuran (10 g), ethyl acetate (70 g), and distilled water (110 g) were added to remove the acid catalyst, and this operation was repeated three times. Subsequently, ethyl acetate (50 g) was added to extract the organic layer, and was treated under reduced pressure. Then, tetrahydrofuran (50 g) was added, and the mixture was added to hexane (300 g) to perform precipitation, and then, filtered and dried to remove 1,4-dioxane and the remaining monomer, thereby obtaining Polymer 4 (Mw: 4,600 g / mol).

[0295] Synthesis Example 5: Synthesis of Polymer 5

[0296] Tri-carbazolyl benzene represented by Chemical Formula 1a (17.21 g, 0.03 mol), 2,5-dimethoxy-p-xylene represented by Chemical Formula 8a (9.97 g, 0.06 mol), p-toluenesulfonic acid monohydrate (0.57 g, 3.0 mmol), and propylene glycol monomethyl ether acetate (27.75 g) were put into a 500 mL flask, and stirred at 110°C to perform a reaction. Sampling was performed every one hour from the polymerization reactant, and measurement was performed with respect to the weight average molecular weight. When the weight average molecular weight reached 2,800 g / mol to 3,000 g / mol, the reaction was quenched. After the polymerization reaction was completed, tetrahydrofuran (10 g), ethyl acetate (70 g), and distilled water (110 g) were added to remove the acid catalyst, and this operation was repeated three times. Subsequently, ethyl acetate (50 g) was added to extract the organic layer, and was treated under reduced pressure. Then, tetrahydrofuran (50 g) was added, and the mixture was added to hexane (300 g) to perform precipitation, and then, filtered and dried to remove propylene glycol monomethyl ether acetate and the remaining monomer, thereby obtaining Polymer 5 (Mw: 3,400 g / mol).

[0297] [Chemical Formula 8a]

[0298]

[0299] Synthesis Example 6: Synthesis of Polymer 6

[0300] Tri(9-carbazolyl)benzene represented by Chemical Formula 1a (17.21 g, 0.03 mol), paraformaldehyde (1.80 g, 0.06 mol), p-toluenesulfonic acid monohydrate (0.06 g, 0.3 mmol), and propylene glycol monomethyl ether acetate (44.50 g) were put into a 500 mL flask, and stirred at 65°C to perform a reaction. Sampling was performed from the polymerization reactant every one hour, and measurement was performed with respect to the weight average molecular weight. When the weight average molecular weight reached 2,700 g / mol to 2,900 g / mol, the reaction was quenched. After the polymerization reaction was completed, tetrahydrofuran (10 g), ethyl acetate (70 g), and distilled water (110 g) were added to remove the acid catalyst, and this operation was repeated three times. Subsequently, ethyl acetate (50 g) was added to extract the organic layer, and was treated under reduced pressure. Then, tetrahydrofuran (50 g) was added, and the mixture was added to hexane (300 g) to perform precipitation, and then, filtered and dried to remove propylene glycol monomethyl ether acetate and the remaining monomer, thereby obtaining Polymer 6 (Mw: 3,300 g / mol).

[0301] Comparative Synthesis Example 1: Synthesis of Polymer A

[0302] 1-hydroxypyrene (10.91 g, 0.05 mol), anthracene-9-carboxaldehyde (10.31 g, 0.05 mol), p-toluenesulfonic acid monohydrate (7.61 g, 0.04 mol), and 1,4-dioxane (28.80 g) were put into a 500 mL flask, and stirred at 110°C to perform a reaction. Sampling was performed from the polymerization reactant every one hour, and measurement was performed with respect to the weight average molecular weight. When the weight average molecular weight reached 2,700 g / mol to 2,900 g / mol, the reaction was quenched. After the polymerization reaction was completed, tetrahydrofuran (10 g), ethyl acetate (70 g), and distilled water (110 g) were added to remove the acid catalyst, and this operation was repeated three times. Subsequently, ethyl acetate (50 g) was added to extract the organic layer, and was treated under reduced pressure. Then, tetrahydrofuran (50 g) was added, and the mixture was added to hexane (300 g) to perform precipitation, and then, filtered and dried to remove 1,4-dioxane and the remaining monomer, thereby obtaining Polymer A (Mw: 3,200 g / mol) including a structural unit represented by Chemical Formula A.

[0303] [Chemical Formula A]

[0304]

[0305] Comparative Synthesis Example 2: Synthesis of Polymer B

[0306] 1-Hydroxypyrene (10.91 g, 0.05 mol), 2,5-dimethoxy-p-xylene (8.31 g, 0.05 mol), p-toluenesulfonic acid monohydrate (0.95 g, 0.005 mol), and propylene glycol monomethyl ether acetic acid (20.18 g) were placed in a 500 mL flask and stirred at 110°C for reaction. Samples were taken from the polymerization reaction every hour and measured for weight average molecular weight. When the weight average molecular weight reached 2,600 g / mol to 2,800 g / mol, the reaction was quenched. After the polymerization reaction was completed, tetrahydrofuran (10 g), ethyl acetate (70 g), and distilled water (110 g) were added to remove the acid catalyst, and this operation was repeated three times. Subsequently, ethyl acetate (50 g) was added to extract the organic layer, which was then treated under reduced pressure. Then, tetrahydrofuran (50 g) was added thereto, and the mixture was added to hexane (300 g) for precipitation, and then, filtered and dried to remove propylene glycol monomethyl ether acetic acid and remaining monomers, thereby obtaining a polymer B (Mw: 3,100 g / mol) including the structural unit represented by Chemical Formula B.

[0307] [Chemical Formula B]

[0308]

[0309] Comparative Synthesis Example 3: Synthesis of Polymer C

[0310] 9-Phenylcarbazole (12.17 g, 0.05 mol), pyrene carboxaldehyde (11.51 g, 0.05 mol) represented by Chemical Formula 7a, p-toluenesulfonic acid monohydrate (7.61 g, 0.04 mol), and 1,4-dioxane (31.29 g) were placed in a 500 mL flask and stirred at 110° C. to react. Samples were taken from the polymerization reaction every hour and measured for weight average molecular weight. When the weight average molecular weight reached 2,800 g / mol to 3,000 g / mol, the reaction was quenched. After the polymerization reaction was completed, tetrahydrofuran (10 g), ethyl acetate (70 g), and distilled water (110 g) were added thereto to remove the acid catalyst, and this operation was repeated three times. Subsequently, ethyl acetate (50 g) was added thereto to extract the organic layer, which was then treated under reduced pressure. Then, tetrahydrofuran (50 g) was added thereto, and the mixture was added to hexane (300 g) for precipitation, and then, filtered and dried to remove propylene glycol monomethyl ether acetic acid and remaining monomers, thereby obtaining a polymer C (Mw: 3,300 g / mol) including the structural unit represented by Chemical Formula C.

[0311] [Chemical Formula C]

[0312]

[0313] Preparation of hard mask composition

[0314] According to the polymers 1 to 6 and A to C of synthesis examples 1 to 6 and comparative synthesis examples 1 to 3, 1.4 g each was dissolved in 10 g of a mixed solvent of propylene glycol monomethyl ether acetate and cyclohexanone in a volume ratio of 7:3, and filtered with a 0.1 μm TEFLON (tetrafluoroethylene) filter, thereby preparing the hard mask compositions according to examples 1 to 6 and comparative examples 1 to 3.

[0315] Evaluation 1: solubility

[0316] The hard mask compositions according to examples 1 to 6 and comparative examples 1 to 3 were stirred at 50°C for 1 hour, and whether each composition was dissolved in the heated state at 50°C was checked. Subsequently, the hard mask compositions were cooled to room temperature of 25°C, and whether each polymer was dissolved at room temperature of 25°C was checked. Subsequently, the hard mask compositions were stirred at room temperature of 25°C for 6 hours each, and allowed to stand at the same room temperature of 25°C, and then whether each polymer was dissolved was checked.

[0317] The results are shown in Table 1.

[0318] (Table 1)

[0319] Solubility Example 1 ◎ Example 2 ◎ Example 3 ◎ Example 4 ○ Example 5 ◎ Example 6 ○ Comparative Example 1 △ Comparative Example 2 ○ Comparative Example 3 △

[0320] ◎: At room temperature of 25°C, no undissolved polymer was visually observed.

[0321] O: At room temperature of 25°C, no undissolved polymer was visually confirmed, but a small amount of undissolved polymer was visually confirmed after standing at room temperature of 25°C.

[0322] Δ: At the heated state of 50°C, no undissolved polymer was visually confirmed, but undissolved polymer was visually confirmed after standing at room temperature of 25°C.

[0323] X: Undissolved polymer was visually confirmed at the heated state of 50°C.

[0324] Referring to Table 1, the polymers 1 to 6 according to synthesis examples 1 to 6 showed improved solubility compared to the comparative polymers A to C according to comparative synthesis examples 1 to 3.

[0325] Evaluation 2: evaluation of etching resistance

[0326] The hard mask compositions according to examples 1 to 6 and comparative examples 1 to 3 were coated on a silicon wafer each, and heat-treated on a hot plate at about 400°C for 2 minutes to form a film of about 1000 A. thick organic film. Then, the organic film was dry-etched for 100 seconds by using CFx gas, and then the thickness of each organic film was measured again by a Field Emission-Scanning Electron Microscope (FE-SEM) (K-MAC).

[0327] According to the calculation equation 1, the bulk etch rate (BER) was calculated using the difference in thickness of the organic film before and after dry-etching and the etching time.

[0328] [Calculation Equation 1]

[0329]

[0330] The results are shown in Table 2.

[0331] (Table 2)

[0332]

[0333] : etch rate is less than

[0334] : etch rate is or more than and less than

[0335] : etch rate is or more than and less than

[0336] : etch rate is or more than

[0337] Referring to Table 2, the organic films formed by the hard mask compositions according to Examples 1 to 6, respectively, showed sufficient etch resistance to etching gas compared to the organic films formed by the hard mask compositions according to Comparative Examples 1 to 3, respectively, and thus improved etch resistance.

[0338] While the present application has been described in connection with what is presently considered to be the practical exemplary embodiments, it is to be understood that the application is not limited to the disclosed embodiments. On the contrary, the application is intended to cover various modifications and equivalent arrangements. Accordingly, the application is not to be considered as limited by the embodiments shown, but only by the appended claims.

Claims

1. A hard mask composition comprising: A polymer and a solvent, wherein the polymer includes a portion derived from a compound represented by Chemical Formula 2: [Chemical Formula 2] in, In Chemical Formula 2, X 1 to X 3 Each independently is N or CR a , where R a is hydrogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C2 to C30 alkynyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof, B 1 To B 6 are each independently a C6 to C30 aromatic ring, and L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof, R 1 to R 3 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclyl group, or a combination thereof, m 1 to m 6 are each independently 0 or 1, and n 1 to n 3 Each independently represents an integer from 0 to 4.

2. The hardmask composition according to claim 1, wherein X 1 to X 3 same.

3. The hard mask composition according to claim 1, wherein B 1 To B 6 Each is independently any one selected from Group 1: [Group 1] 4. The hard mask composition according to claim 1, wherein L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a divalent group including a substituted or unsubstituted benzene moiety bonded via a single bond.

5. The hard mask composition according to claim 1, wherein L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted quaterphenylene group, or a substituted or unsubstituted pentphenylene group.

6. The hardmask composition according to claim 1, wherein L 1 to L 3 Each is independently represented by Chemical Formula 3: [Chemical Formula 3] in, In Chemical Formula 3, l is an integer from 0 to 4, and * is a connection point with other parts in the compound represented by Chemical Formula 2.

7. The hard mask composition according to claim 1, wherein m 1 and m 2 At least one of is 1, m 3 and m 4 At least one of is 1, and m 5 and m 6 At least one of is 1.

8. The hard mask composition according to claim 1, wherein The compound represented by Chemical Formula 2 is a first compound, and The polymer includes structural units obtained by reacting a reaction mixture comprising: the first compound; and a second compound different from the first compound and including at least one carbonyl moiety, an ether moiety, or a combination thereof.

9. The hard mask composition according to claim 8, wherein The second compound includes: at least one aldehyde group; or At least two alkyl groups are substituted with a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkenyloxy group, a substituted or unsubstituted C2 to C30 alkynyloxy group, or a combination thereof.

10. The hardmask composition according to claim 8, wherein the second compound is represented by Chemical Formula 7 or Chemical Formula 8: [Chemical Formula 7] in, In Chemical Formula 7, A is hydrogen, a substituted or unsubstituted C6 to C40 aromatic ring, a substituted or unsubstituted C2 to C30 heterocyclic ring, or a combination thereof; [Chemical Formula 8] In Chemical Formula 8, D is a substituted or unsubstituted C6 to C40 aromatic ring, and R 4 and R 5 Each is independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof.

11. The hardmask composition according to claim 10, wherein A is hydrogen or a substituted or unsubstituted one selected from Group 2: [Group 2] in, In Group 2, Y 1 and Y 2 are each independently hydrogen, C6 to C30 aryl, C2 to C30 heterocyclic group or a combination thereof, Z 1 to Z 5 are each independently a C6 to C30 aromatic ring, and W 1 and W 2 Each is independently BR b NR c ,O,S,PR d or P(=O)R e , where R b to R e and each is independently hydrogen, C1 to C30 alkyl, C2 to C30 alkenyl, C2 to C30 alkynyl, C1 to C30 heteroalkyl, C3 to C30 cycloalkyl, C3 to C30 cycloalkenyl, C6 to C30 aryl, C2 to C30 heterocyclyl, or a combination thereof.

12. The hardmask composition according to claim 10, wherein D is a substituted or unsubstituted one selected from Group 3: [Group 3] in, In Group 3, W is a single bond, -O-, -S-, -SO2-, substituted or unsubstituted vinylene, -C(=O)-, CR g R h NR i or a combination thereof, wherein R g to R i and each is independently hydrogen, halogen, carboxyl, substituted or unsubstituted C2 to C30 oxoalkyl, substituted or unsubstituted C1 to C30 alkoxycarbonyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C30 alkenyl, substituted or unsubstituted C1 to C30 alkynyl, substituted or unsubstituted C1 to C30 heteroalkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C3 to C30 cycloalkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, or a combination thereof, p is an integer from 1 to 30, and * is a connection point with other parts in the second compound represented by Chemical Formula 8.

13. The hardmask composition according to claim 10, wherein R 4 and R 5 each is independently substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted vinyl, substituted or unsubstituted propenyl, substituted or unsubstituted butenyl, substituted or unsubstituted pentenyl, substituted or unsubstituted hexenyl, substituted or unsubstituted ethynyl, substituted or unsubstituted propynyl, substituted or unsubstituted butynyl, substituted or unsubstituted pentynyl, substituted or unsubstituted hexynyl, or a combination thereof.

14. The hardmask composition of claim 8, wherein the reaction mixture further comprises a third compound that is different from the first compound and the second compound and comprises a substituted or unsubstituted C6 to C40 aromatic ring, a substituted or unsubstituted C2 to C30 heterocyclic ring, or a combination thereof. 15 . The hardmask composition of claim 14 , wherein the third compound comprises a C6 to C40 aromatic ring that is substituted or unsubstituted with at least one hydroxyl group, an amine group, a substituted or unsubstituted C1 to C30 alkoxy group, or a combination thereof.

16. A hard mask composition comprising: A polymer and a solvent, the polymer including a portion derived from a compound represented by any one of Chemical Formulas 4 to 6: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] in, In Chemical Formulas 4 to 6, X 1 to X 3 Each independently is N or CR a , where R a is hydrogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C2 to C30 alkynyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof, R 1 to R 3 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclyl group, or a combination thereof, and l 1 to l 3 and n 1 to n 3 Each independently represents an integer from 0 to 4.

17. A method for forming a pattern, comprising: applying the hard mask composition according to claim 1 or claim 16 on a material layer and heat-treating the resultant 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.

Images