Dry photoresist or hard mask for EUV lithography

Abstract

Disclosed are organometallic compounds, compositions, and dry photoresists or hard masks for extreme ultraviolet (EUV) lithography. The organometallic compounds comprise at least one bismuth element selected from Bi(III) and Bi(V). The organometallic compounds also comprise at least one C1-C6 alkyl ligand and at least one terminal or bridging ligand A (O, S, or NR, where the R group in NR is H or C1-C6 alkyl) bonded to the bismuth element. Methods for preparing dry photoresist or hard mask compositions and methods for forming patterned material features on a substrate using the compositions are also disclosed.

Description

[Technical Field]

[0001] This disclosure relates to photoresist materials for extreme ultraviolet (EUV) lithography, and more specifically, to organometallic compounds for dry photoresists or hard masks. [Background technology]

[0002] A photoresist is a photosensitive material that resists the action of a certain chemical substance in a desired area after photoimaging and subsequent processing. Examples of photoresists for deep ultraviolet (DUV) and EUV lithography at the 7nm and 5nm technology nodes include polymer-based chemically amplified photoresists and organometallic photoresists. Organometallic photoresists contain organotin compounds, which, upon EUV exposure, dissociate the organotin-C bond, resulting in changes in solubility or the generation of volatile products. Hard masks are materials used in semiconductor processing as etching masks, replacing polymer or other organic "soft" resist materials.

[0003] However, currently available chemically amplified photoresists for EUV lithography may have limitations in resolution and pattern quality due to stochastic effects and the relatively long diffusion distance of acids. Dry photoresists and hard masks can be more sensitive than chemically amplified photoresists. Examples of dry photoresist or hard mask platforms include organotin precursors, tetramethyltin, and tin halide precursors, tin(IV) bromide. However, these can present processing challenges due to their processing window. For example, tetramethyltin has a low boiling point and evaporates rapidly from the wafer surface when placed under vacuum at room temperature. In addition, its vapor pressure of around 100 Pa at room temperature makes it difficult to control the sublimation of tin(IV) bromide.

[0004] Currently available chemically amplified photoresists also have drawbacks in terms of toxicity and chemical waste due to the use of fluorinated photoacid generators. Existing dry photoresist or hard mask platforms may have similar drawbacks due to the use of organotin compounds and / or bromine or chlorine reaction products. Furthermore, mitigating the process integration risks associated with these platforms is a challenge. [Overview of the project]

[0005] Embodiments of this disclosure relate to organometallic compounds for dry photoresists or hard masks for EUV lithography. The organometallic compounds comprise at least one bismuth element selected from Bi(III) and Bi(V). The organometallic compounds also have at least one terminal or bridging ligand A bonded to the bismuth element. Ligand A is O, S, or NR, where the R group in NR is H or C1-C6 alkyl. The organometallic compounds also have at least one C1-C6 alkyl ligand bonded to the bismuth element. In some embodiments, the organometallic compounds may be represented by general formulas (I), (II), (III), (IV), (V), (VI), and (VII). [ka] Equation (I), [ka] Formula (II), [ka] Formula (III), [ka] Formula (IV), [ka] Formula (V), [ka] Formula (VI), and [ka] Formula (VII), Here, in general formulas (I), (II), (III), (IV), (V), (VI), and (VII), A represents O, S, or NR; each of R1, R2, R3, R4, R5, R6, R7, and R8 represents an optionally substituted linear or branched C1-C6 alkyl, an optionally substituted C3-C6 cycloalkyl, or an optionally substituted C3-C6 heterocycloalkyl; n is an integer from 1 to 4; m is an integer from 2 to 5; and R in NR represents H, an optionally substituted linear or branched C1-C6 alkyl, an optionally substituted C3-C6 cycloalkyl, or an optionally substituted C3-C6 heterocycloalkyl. Organometallic compounds may enable more sensitive and environmentally friendly photoresists or hard masks than existing materials.

[0006] Further embodiments relate to a method for preparing a dry photoresist or hard mask composition for EUV lithography, including the step of providing an organometallic compound. Additional embodiments relate to a dry photoresist or hard mask composition comprising an organometallic compound, and a dry photoresist or hard mask for EUV lithography comprising the composition.

[0007] Additional embodiments relate to a method for forming patterned material features. The method includes the steps of providing a material surface on a substrate and forming a layer of dry photoresist or hard mask composition on the material surface. The method also includes the step of irradiating the dry photoresist or hard mask layer in a patterned manner with energy rays to form a pattern of irradiated / exposed areas in the dry photoresist or hard mask layer. Then, a portion of the dry photoresist or hard mask layer is selectively removed to form an exposed portion of the material surface. The patterned material features are formed by etching or ion implanting the exposed portion of the material. [Brief explanation of the drawing]

[0008] The drawings included in this application are incorporated herein and form part of this specification. They illustrate embodiments of the disclosure and, together with the description, serve to illustrate the principles of the disclosure. The drawings are illustrative of specific embodiments and do not limit the disclosure.

[0009] [Figure 1] This graph shows the photon absorption cross-sections of all natural elements at 92 eV.

[0010] [Figure 2] A set of chemical structure diagrams (a) to (j) representing organometallic compounds for dry photoresists or hard masks for EUV lithography, according to several embodiments.

[0011] [Figure 3A] The first set of chemical structure diagrams (a) to (o) represent single, linear, and cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography according to several embodiments, where Bi is in oxidation state (III).

[0012] [Figure 3B] A second set of chemical structure diagrams (p) to (ad) representing single, linear, and cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography according to some embodiments are shown, where Bi is in oxidation state (V).

[0013] [Figure 4-1] Figure 4A shows a set of chemical structure diagrams illustrating single organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (I) and (IV), according to several embodiments. [Figure 4-2]Figure 4B shows a set of chemical structure diagrams illustrating single organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (I) and (IV), according to several embodiments. [Figure 4-3] Figures 4C and 4D are a set of chemical diagrams showing single organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (I) and (IV), according to several embodiments. [Figure 5] Figures 5A and 5B are a set of chemical diagrams showing single organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (I) and (IV), according to several embodiments.

[0014] [Figure 6] Figures 6A and 6B are a set of chemical diagrams showing linear organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (II), (V), and (VI), according to several embodiments. [Figure 7] Figures 7A and 7B are a set of chemical diagrams showing linear organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (II), (V), and (VI), according to several embodiments.

[0015] [Figure 8A] Here is a set of chemical diagrams showing cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (III) and (VII), according to several embodiments. [Figure 8B] Here is a set of chemical diagrams showing cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (III) and (VII), according to several embodiments. [Figure 9A]Here is a set of chemical diagrams showing cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (III) and (VII), according to several embodiments. [Figure 9B] Here is a set of chemical diagrams showing cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (III) and (VII), according to several embodiments.

[0016] [Figure 10A] Here is a set of chemical diagrams showing cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (III) and (VII), according to several embodiments. [Figure 10B] Here is a set of chemical diagrams showing cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (III) and (VII), according to several embodiments. [Figure 11A] Here is a set of chemical diagrams showing cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (III) and (VII), according to several embodiments. [Figure 11B] Here is a set of chemical diagrams showing cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (III) and (VII), according to several embodiments.

[0017] [Figure 12] This flowchart shows a process for forming patterned material features on a substrate using a dry photoresist or hard mask composition, according to several embodiments.

[0018] While the invention is suitable for various modifications and alternative forms, such types are illustrated and described in detail in the drawings. However, it should be understood that the intent is not to limit the invention to the specific embodiments described. Rather, the invention is intended to encompass all modifications, equivalents, and alternatives within the spirit and scope of the invention. [Modes for carrying out the invention]

[0019] This disclosure relates to photoresist materials for extreme ultraviolet (EUV) lithography, and more specifically, to organometallic compounds for dry photoresists or hard masks.

[0020] The descriptions of the various embodiments of this disclosure are for illustrative purposes only and are not intended to be exhaustive or limitful to the embodiments disclosed. Many modifications and variations will be apparent to those skilled in the art without departing from the scope and spirit of the embodiments described. The terminology used herein has been selected to best describe the principles of the embodiments, their practical applications or technical improvements to the art found in the market, or to enable other persons skilled in the art to understand the embodiments disclosed herein.

[0021] Unless otherwise specified, the following terms used in this application, including in the specification and claims, are given the following definitions: When used in the specification and appended claims, the singular forms “a,” “an,” and “the” include multiple subjects unless the context clearly indicates otherwise. When used herein, the term “comprising” means that the designated component is essential, but other components may be added and further included in the composition. When used herein, the term “consisting of,” as used pursuant to this disclosure, generally means that the total amount of the components of the composition is 100%, indicating that the subject matter is limited and may only include the expressly stated limitations. Whenever “comprising” is referred to, it is intended to include both the meaning as a substitute, i.e., it may mean either “comprising” or “consisting of,” unless the context clearly indicates otherwise.

[0022] The terms “compound” or “compounds of the disclosure” refer to all compounds encompassed in structural formulas (I) through (VII) or structural formulas (a) through (ad) disclosed herein, including each subgenus and all specific compounds within the formula whose structures are disclosed herein. Compounds may be identified by either their chemical structure and / or chemical name. Where the chemical structure and / or chemical name are inconsistent, the chemical structure shall determine the uniqueness of the compound.

[0023] As used herein, the term “at least one alkyl” means that the organometallic compounds relating to this disclosure may contain one alkyl ligand, or two, three, four, five, six, or more alkyl ligands, which may be the same or different. As further defined below, the number of alkyl ligands depends on the oxidation state, i.e., the valence, of the Bi element in the organometallic compound, and on whether the organometallic compound is linear or cyclic.

[0024] As used herein, the term “aliphatic” includes the terms alkyl, alkenyl, or alkynyl.

[0025] As used herein, the “alkyl” group refers to an aliphatic saturated hydrocarbon group containing one to eight (e.g., one, two, three, four, five, six, seven, or eight) carbon atoms. Alkyl groups can be linear, branched, cyclic, or any combination thereof. Unless specifically limited herein, the terms “alkyl,” and their derivatives such as “alkoxy” or “thioalkyl,” as used herein, include linear, branched, and cyclic parts within that scope. When an alkyl radical is further bonded to another atom, it becomes an alkylene radical or alkylene group. In other words, the term “alkylene” also refers to a divalent linear or branched alkyl group. For example, -CH2CH3 is ethyl, while -CH2CH2- is ethylene. The term “alkylene” refers to a saturated linear or branched divalent hydrocarbon radical obtained by removing two hydrogen atoms from a single carbon atom or from two different carbon atoms of a starting alkane, either alone or as part of another substituent.

[0026] In preferred modifications relating to this disclosure, the linear or branched alkyl or alkylene group comprises one to eight carbon atoms. In other even more preferred modifications, the linear or branched alkyl or alkylene group comprises one to six carbon atoms. More preferred relating to this disclosure are saturated linear or branched C1 to C6 alkyl groups or saturated linear or branched C1 to C6 alkylene groups. Most preferred are linear or branched alkyl or alkyl or alkylene groups having one to four carbon atoms. Preferred alkyl radicals / partial alkyl groups include, but are not limited to, C1 to C6 alkyl groups, including methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl. The alkyl or alkylene groups as defined above may be substituted with one or more substituents, as shown below. The terms “alkyl” or “alkylene” further include radicals or groups having any degree of saturation, such as groups having only carbon-carbon single bonds (“alkyl” or “alkylene”), groups having one or more carbon-carbon double bonds (“alkenyl”), radicals having one or more carbon-carbon triple bonds (“alkynyl”), and groups having a mixture of carbon-carbon single, double, and / or triple bonds.

[0027] The term “alkenyl” as used in this disclosure refers to an unsaturated linear or branched monovalent hydrocarbon radical having at least one carbon-carbon double bond (C=C double bond), either alone or as part of another substituent. The radical may be in either a cis or trans conformation around the double bond. Thus, the term “alkenyl” also includes the corresponding cis / trans isomers. In preferred modifications of this disclosure, the linear or branched alkenyl group contains two to eight carbon atoms. In other preferred modifications, the linear or branched alkenyl group contains two to six carbon atoms. In even more preferred modifications, the linear or branched alkenyl group contains two to four carbon atoms. Preferred in this disclosure are mono- or diunsaturated linear or branched C2 to C6 alkenyl groups. Typical alkenyl radicals or alkenyl groups include, but are not limited to, ethenyl; propenyl such as prop-1-en-1-yl, prop-1-en-2-yl, prop-2-en-1-yl(allyl), prop-2-en-2-yl, cycloprop-1-en-1-yl, cycloprop-2-en-1-yl; butenyl such as but-1-en-1-yl, but-1-en-2-yl, 2-methylprop-1-en-1-yl, but-2-en-1-yl, but-2-en-2-yl, but-1,3-dien-1-yl, but-1,3-dien-2-yl, and similar groups. The alkenyl groups defined above may be substituted with or without one or more substituents, as shown below.

[0028] The term “alkynyl” as used in this disclosure refers to an unsaturated linear or branched monovalent hydrocarbon radical having at least one carbon-carbon triple bond (C≡C triple bond), either alone or as part of another substituent. In preferred modifications as used in this disclosure, the linear or branched alkynyl group contains two to eight carbon atoms. In other preferred modifications, the alkynyl group contains two to six carbon atoms. In even more preferred modifications, the alkynyl group contains two to four carbon atoms. The most preferred as used in this disclosure are mono- or diunsaturated linear or branched C2 to C6 alkynyl groups. Typical alkynyl radicals / parts or alkynyl groups include, but are not limited to, ethynyl; propynyl such as prop-1-in-1-yl, prop-2-in-1-yl; butynyl such as buta-1-in-1-yl, buta-1-in-3-yl, buta-3-in-1-yl, and similar groups. The alkynyl group as defined above may be further substituted with one or more substituents, as shown below.

[0029] The term “alkoxy” as used in this disclosure means a linear or branched radical of formula -OR, either alone or as part of another substituent, where R is alkyl or substituted alkyl as defined herein. In preferred modifications of this disclosure, the linear or branched alkoxy group comprises one to eight carbon atoms. In other preferred modifications, the linear or branched alkoxy group comprises one to six carbon atoms. In even more preferred modifications, the linear or branched alkoxy group comprises one to four carbon atoms. In some embodiments, the most preferred is a linear or branched C1 to C6 alkoxy group. Typical alkoxy radicals / partial or alkoxy groups include C1 to C4 alkoxys such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy; as well as pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, and 1-methylpentoxy The alkoxy groups include C1 to C6 alkoxy groups such as xy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, or 1-ethyl-2-methylpropoxy. The alkoxy groups as defined above may be further substituted.

[0030] The terms "alkylthio" or "thioalkoxy" refer to the radical of formula -SR, either alone or as part of another substituent, where R is alkyl or substituted alkyl, as defined herein.

[0031] In this specification, the terms “alkyl” or “alkylene” also include heteroalkyl radicals or heteroalkyl groups. The term “heteroalkyl” refers to an alkyl group in which one or more carbon atoms are independently replaced by the same or another heteroatom, or by the same or another heteroatomic group, either by itself or as part of another substituent. Examples of heteroatom groups that may be included in these groups include, but are not limited to, -O-, -S-, -OO-, -SS-, -OS-, -NR-, =NN=, -N=N-, -N=NNR-, BR-, PR-, -P(O)2-, -POR-, -OP(O)2-, -SO-, -SO2-, -SR2OR-, -S(O)NR-, -S(O)2NR-, and similar groups, where R is independently, as defined herein, hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, or substituted heteroarylalkyl. Heteroatoms or heteroatom groups may be located at any internal position of the alkyl group.

[0032] As used herein, the term “cyclic” means an aliphatic ring compound or group comprising at least three carbon atoms, where all bonds between adjacent pairs of atoms may be of the single bond designation type (with two electrons), or some of them may be double or triple bonds (with four or six electrons, respectively). As used herein, the “cycloalkyl” group means a saturated carbon ring of three to eight (e.g., three, four, five, six, seven, or eight) carbon atoms. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Cycloalkyl groups as defined above may or may not be substituted with one or more substituents, as shown below.

[0033] As used herein, the term "heterocycloalkyl" refers to a saturated non-aromatic cyclic monovalent hydrocarbon radical in which one or more carbon atoms are independently replaced by the same or different heteroatoms, either alone or as part of another substituent. Exemplary heteroatoms that replace carbon atoms include, but are not limited to, N, B, P, O, S, Si, and the like. Exemplary heterocycloalkyl groups include, but are not limited to, groups derived from epoxides, aziridines, thiiranes, imidazolidines, morpholines, piperazines, piperidines, pyrazolidines, pyrrolidones, quinuclidines, and the like.

[0034] The heterocycloalkyl moiety can occur as a monocyclic compound having only a single ring. Preferably, the term "heterocycloalkyl" encompasses 3- to 7-membered, saturated, mono- or poly-unsaturated heterocycloalkyl radicals containing one, two, three, or four heteroatoms selected from the group consisting of O, N, and S. One or more heteroatoms may be at any position in the heterocycloalkyl ring. In one preferred variation, the term "heterocycloalkyl" includes 3- to 7-membered monocyclic heterocycloalkyl radicals. In another even more preferred variation, the heterocycloalkyl radical includes 3, 4, 5, 6, 7, or 8-membered monocyclic heterocycloalkyl radicals.

[0035] Typical heterocycloalkyl radicals include azilidinyl, oxyranil, thyranil, azetidinyl, oxetanil, thietanil, 2-tetrahydrofuranil, 3-tetrahydrofuranil, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl Includes, but is not limited to, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, and similar ring members comprising one or two nitrogen atoms and / or one oxygen or sulfur atom, or 3 to 6 member saturated heterocycloalkyls containing one or two oxygen and / or sulfur atoms.

[0036] The heterocycloalkyl residues or heterocycloalkyl groups defined above may be substituted with one or more substituents, or they may not be substituted with one or more substituents, as shown below.

[0037] As used herein, the terms "amine" or "amino" include compounds in which a nitrogen atom is covalently bonded to at least one carbon or heteroatom. The terms "amine" or "amino" also include -NH2 and also include a substituent moiety. The terms "amine" or "amino" include "alkylamino" and include groups and compounds in which nitrogen is bonded to at least one additional alkyl group. As used herein, the term "imino" group or residue means a divalent group =NR, where R represents either H or an alkyl group as defined herein. In some embodiments, the imino group can be either a terminal group or a bridging ligand in a general formula as defined herein that is bonded to a Bi(III) or Bi(V) element by a double bond.

[0038] As used herein, an "alkoxy" group refers to an alkyl - O - group, where "alkyl" is as defined above. The term "alkylthio" includes linear alkylthio, branched alkylthio, cycloalkylthio, cyclic alkylthio, heteroatom - unsubstituted alkylthio, heteroatom - substituted alkylthio, heteroatom - unsubstituted C n - alkylthio, and heteroatom - substituted C n - alkylthio. In certain embodiments, lower alkylthio is contemplated.

[0039] The term "halogen" residue / portion or group refers to F, Cl, Br, or I, either alone or as part of another substituent.

[0040] The phrase "optionally substituted" is used in the same sense as the phrase "unsubstituted or substituted". As described herein, the compounds of the present disclosure can be optionally substituted with one or more substituents such as those generally described above or exemplified in a particular class, subclass, and species of the present disclosure. As described herein, any of the above - mentioned moieties or those introduced below can be optionally substituted with one or more substituents described herein.

[0041] In the context of this disclosure, the term “substitution” means that one or more hydrogen atoms of an intended radical or group are independently replaced with the same or different substituents. In addition, the term “substitution” specifically provides one or more substituents, e.g., two, three, or more, that are commonly used in the art. However, it is generally known that substituents should be selected so as not to adversely affect the useful properties or functions of the compound.

[0042] Preferred substituents in the context of this disclosure preferably include halogen groups, perfluoroalkyl groups, perfluoroalkoxy groups, alkyl groups, alkenyl groups, alkynyl groups, hydroxyl groups, oxo groups, mercapto groups, alkylthio groups, alkoxy groups, aryl or heteroaryl groups, aryloxy or heteroaryloxy groups, arylalkyl or heteroarylalkyl groups, arylalkoxy or heteroarylalkoxy groups, amino groups, alkyl and dialkylamino groups, carbamoyl groups, alkylcarbonyl groups, carboxyl groups, alkoxycarbonyl groups, alkylaminocarbonyl groups, dialkylaminocarbonyl groups, arylcarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, cycloalkyl groups, cyano groups, C1 to C6 alkylthio groups, arylthio groups, nitro groups, keto groups, acyl groups, boronic acid or vonyl groups, phosphoric acid or phosphonyl groups, sulfamyl groups, sulfonyl groups, sulfinyl groups, and combinations thereof.

[0043] Substituents or groups of substituents useful for substituting saturated carbon atoms in the indicated group or radical are more preferably halogens, hydroxyls, alkyls, alkenyls, alkynyls, alkoxyls, -NH2, aminos (primary, secondary, or tertiary), nitros, thiols, thioethers, imines, cyanos, amides, phosphonates, phosphines, carboxyls, thiocarbonyls, sulfonyls, sulfonamides, ketones, aldehydes, esters, acetyls, acetoxys, carbamoyls, oxygen (O); haloalkyls (e.g., trifluoromethyl); aminoacyls and aminoalkyls, carbocyclic cycloalkyls which may be monocyclic or condensed or uncondensed polycyclic (e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl), or This includes, but is not limited to, heterocycloalkyls that may be monocyclic or condensed or non-condensed polycyclic (e.g., pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, or thiadinyl), carbocyclic or heterocyclic, monocyclic or condensed or non-condensed polycyclic aryls (e.g., phenyl, naphthyl, pyrrolyl, indolyl, furanil, thiophenyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, pyrazinyl, pyridadinyl, pyrimidinyl, benzimidazolyl, benzothiophenyl, or benzofuranil), -CO2CH3, -CONH2, -OCH2CONH2; -SO2NH2, -OCHF2, -CF3, and -OCF3.

[0044] Modifications or derivatives of the compounds disclosed herein are intended to be useful in the methods and compositions of this disclosure. Derivatives may be prepared, and the properties of such derivatives may be assayed for their desired properties by any method known to those skilled in the art. In some embodiments, “derivative” refers to a chemically modified compound that still retains the desired effect of the compound before chemical modification.

[0045] Since conventional materials and processing techniques can be employed in various embodiments, such conventional embodiments are not described in detail herein. For example, the selection of suitable solvents, photosensitizers, pigments, fillers, antistatic agents, flame retardants, defoamers, light stabilizers, and antioxidants can be carried out in conventional ways.

[0046] Next, looking at an overview of the technology specifically relating to aspects of this disclosure, examples of photoresists for far-ultraviolet (DUV) and EUV lithography at 7nm and 5nm technology nodes include polymer-based chemically amplified photoresists and organometallic photoresists such as organotin photoresists. These photoresist platforms may include photoacid generators and acid-unstable polymers. The acid-unstable protecting groups of these polymers can be removed by acid, resulting in alkali-soluble or volatile compounds. Organometallic photoresist platforms are also used. For example, EUV exposure can dissociate organotin Sn-C bonds, resulting in solubility changes or the generation of volatile products.

[0047] Generally, photoresists for far-ultraviolet (DUV) and EUV lithography at the 7nm and 5nm technology nodes were typically polymer-based chemically amplified photoresists. These photoresist platforms contain photoacid generators (PAGs) and acid-unstable polymers. The acid-unstable protecting groups of these polymers can be removed by acid, resulting in alkali-soluble or volatile compounds. Organometallic photoresist platforms, such as organotin photoresists, are also used. For example, EUV exposure can dissociate the Sn-C bond in organotin photoresists, resulting in changes in solubility or the generation of volatile products.

[0048] A key characteristic of photoresists is their sensitivity. Sensitivity is the amount of UV light required to print a feature onto the photoresist. Currently available chemically amplified photoresists for EUV lithography may have insufficient sensitivity for various applications.

[0049] Another important metric for photoresists is their resolution or pattern quality. Currently available chemically amplified photoresists for EUV lithography may have limited resolution and pattern quality due to stochastic effects related to the relatively small number of absorbed photons and the relatively long diffusion distance of the acid.

[0050] Organometallic photoresists are more sensitive than chemically amplified photoresists. Examples of organometallic photoresists for EUV lithography include organotin clusters, which are applied by chemical vapor deposition (CVD) or atomic layer deposition (ALD). In these examples, EUV exposure dissociates the Sn-C bond and inorganic SnO x Cluster crosslinking can occur. This leads to a change in solubility, where the unexposed material is soluble in an alkaline solvent, while the exposed material is not. These photoresist platforms may be more sensitive in EUV than state-of-the-art chemically amplified photoresists, but further performance improvements are needed.

[0051] Dry photoresists or hard masks for EUV lithography can also be more sensitive than chemically amplified photoresists. An exemplary dry photoresist or hard mask platform includes an organotin precursor, tetramethyltin, or tin halide precursor, and tin(IV) bromide. During EUV exposure, the Sn-C or Sn-Br bond dissociates, resulting in Sn metal and ethane or bromine, respectively. Ethane and bromine are volatile under the processing conditions of the EUV scanner. Therefore, only the Sn metal is left behind. This photoresist platform can be more sensitive in EUV than chemically amplified photoresists, although the processing window becomes a challenge. Tetramethyltin is a low-boiling-point liquid and evaporates quickly from the wafer surface when under vacuum at room temperature. Tin(IV) bromide has a vapor pressure of around 100 Pa at room temperature, and controlling the sublimation of tin(IV) bromide is difficult.

[0052] Furthermore, increasing attention is being paid to the toxicity and chemical waste of photoresists. To date, legislation has been enacted to control and phase out the use of fluorinated materials such as perfluorocarbons and sulfur hexafluoride. Regulatory bodies are scrutinizing the use of fluorinated materials, and it is anticipated that international measures regarding these materials will be taken as a result. Currently available chemically amplified photoresists for DUV and EUV lithography generally have drawbacks in terms of toxicity and chemical waste, due to the use of fluorinated photoacid generators.

[0053] Organometallic photoresist platforms and dry photoresist or hard mask platforms generally do not contain fluorine; however, existing platforms often suffer from similar drawbacks due to the incorporation of organotin compounds and / or bromine or chlorine reaction products, both of which are strong oxidizing agents. Furthermore, while existing dry photoresists or hard masks for EUV lithography generally have high sensitivity, mitigating process integration risks remains a challenge.

[0054] Therefore, there is a need for photoresists for EUV lithography that are highly sensitive, have good resolution / pattern quality, produce low toxicity / chemical waste, and have low process integration risk. Disclosed herein are organometallic compounds that, in some embodiments, can address these and other challenges. The disclosed organometallic compounds can be formulated into dry photoresist or hard mask compositions that may be useful in lithography processes, particularly when EUV irradiation is used.

[0055] In some embodiments, the organometallic compound comprises at least one terminal or bridging ligand (A) and at least one bismuth (Bi(III) or Bi(V)) element bonded to at least one C1-to-C6 alkyl ligand. The metallic element bismuth has a large absorption cross-section for EUV photons. Examples of terminal ligands may include oxo, thioxo, and imino (=NR), and examples of bridging ligands may include oxygen, sulfur, and amino (-N(R)-). The R group or R residue in NR may be H, as defined herein, or an alkyl ligand such as an alkyl ligand bonded to a Bi(III) or Bi(V) element.

[0056] The disclosed organometallic compounds for dry photoresists or hard masks for EUV lithography may offer advantages over existing materials (see above) in terms of toxicity and chemical waste. For example, the disclosed compounds are fluorine-free, in contrast to currently available chemically amplified photoresists that use fluorinated PAG. In addition, the disclosed compounds are tin-free, in contrast to currently available organometallic photoresists and dry photoresists or hard masks for EUV lithography.

[0057] The disclosed organometallic compounds for dry photoresists or hard masks for EUV lithography may also have advantages over existing materials with respect to resolution or pattern quality. The disclosed organometallic molecules have a high melting point temperature, and accordingly, a high activation energy for diffusion. Thus, the disclosed molecules may have a low diffusion coefficient under the processing conditions in an EUV scanner. Moreover, the disclosed organometallic molecules have a high density, and accordingly, a low shrinkage when inorganic clusters crosslink due to EUV exposure.

[0058] The organometallic molecules for dry photoresists or hard masks for EUV lithography taught herein may have a high absorption cross-section for photons in EUV. Thus, the disclosed compounds may have high sensitivity in EUV. The disclosed organometallic molecules for dry photoresists or hard masks for EUV lithography may also reduce the process integration risk. For example, the disclosed compounds are solids with a high melting point temperature and a very low vapor pressure under the conditions (vacuum) seen in EUV scanners.

[0059] FIG. 1 is a graph showing the photon absorption cross-section μ at 92 eV for all natural elements. In order to devise materials that can be used to increase the sensitivity of photoresists for EUV lithography, it is essential to understand and recognize the microscopic mechanisms that cause photon absorption events in EUV, in contrast to the mechanisms in DUV. a For devising materials that can be used to increase the sensitivity of photoresists for EUV lithography, it is essential to understand and recognize the microscopic mechanisms that cause photon absorption events in EUV, in contrast to the mechanisms in DUV.

[0060] DUV (193 nm, 6 eV) photon absorption is determined by the molecular orbitals of the photoresist material. The absorbed photons can directly and selectively cause resonance electron transitions in the photoacid generator, resulting in the generation of acid. The sensitivity of chemically amplified photoresists for DUV lithography can be improved by adjusting the molecular structure of the photoacid generator. On the other hand, EUV (13.5 nm, 92 eV, soft X-ray) photon absorption is determined by the atomic composition of the photoresist material rather than the molecular structure.

[0061] The absorption of photons in a layer of thickness d is given by 1-exp(-n μ). a The photon absorption cross-section of the photoresist at 92 eV is given by d), where n is the number of atoms per unit volume in the layer. To increase the photon absorption cross-section of the photoresist at 92 eV, elements having a large absorption cross-section at this photon energy can be added to the photoresist composition. For example, the elements In, Sn, Sb, Te, Bi, Sb, and Po have large absorption cross-sections for EUV photons. Of these, bismuth (Bi) may have advantages in terms of toxicity, stability, and cost.

[0062] In this specification, organometallic compounds for dry photoresists or hard masks for EUV lithography include metal element Bi in oxidation state (III) or metal element Bi in oxidation state (V). By providing metal element Bi having ligand A, the melting point temperature of the molecule can be increased, and consequently, the activation energy of the molecule for diffusion can be increased, and therefore the diffusion coefficient of the molecule under processing conditions in an EUV scanner can be reduced.

[0063] The C1 to C6 alkyl ligands of organometallic compounds can be selected such that the reaction products formed during EUV exposure are volatile under processing conditions in the EUV scanner, excluding inorganic clusters (Bi=O clusters, Bi=S clusters, Bi=N clusters, Bi-O clusters, Bi-S clusters, or Bi-N clusters). EUV exposure can dissociate Bi-C and NR bonds in organometallic compounds. Upon dissociation, alkyl groups can become radicals, and inorganic Bi=O clusters, Bi=S clusters, Bi=N clusters, Bi-O clusters, Bi-S clusters, or Bi=N clusters can be crosslinked. The resulting C1 to C6 alkyl radicals react in pairs to form volatile and evaporative C2 to C12 alkyl species. For example, when the alkyl ligand is methyl or ethyl, the volatile products are ethane or butane, respectively. Non-volatile crosslinked inorganic clusters may remain on the substrate as reaction products after the evaporation of volatile organoalkyl species.

[0064] Organometallic compounds can be represented by general formulas (I), (II), (III), (IV), (V), (VI), and (VII). [ka] Equation (I), [ka] Formula (II), [ka] Formula (III), [ka] Formula (IV), [ka] Formula (V), [ka] Formula (VI), and [ka] Formula (VII), Here, in general formulas (I), (II), (III), (IV), (V), (VI), and (VII), A represents O, S, or NR; each of R1, R2, R3, R4, R5, R6, R7, and R8 represents an optionally substituted linear or branched C1-C6 alkyl, an optionally substituted C3-C6 cycloalkyl, or an optionally substituted C3-C6 heterocycloalkyl; n is an integer from 1 to 4; m is an integer from 2 to 5; and R in NR represents H, or any optionally substituted linear or branched C1-C6 alkyl, an optionally substituted C3-C6 cycloalkyl, or an optionally substituted C3-C6 heterocycloalkyl.

[0065] In preferred modifications, the organometallic compound is a single compound relating to general formula (I), where Bi is in the oxidized state (III), or a single compound relating to general formula (IV), where Bi is in the oxidized state (V). In more preferred modifications, the organometallic compound is a linear acyclic compound relating to general formula (II), (V), or (VI), where n is an integer from 1 to 3. Most preferably, n is 1 or 2. Even more preferably, the organometallic compound is a cyclic compound relating to general formula (III) or (VII), where m is an integer from 2 to 4. Most preferably, m is 2 or 3.

[0066] In some embodiments, in organometallic compounds represented by any one of the general formulas (I) to (VII) specified above, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, or RN are optionally substituted linear or branched C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, or optionally substituted C3-C6 heterocycloalkyl groups, particularly optionally substituted linear C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, or optionally substituted C3-C6 heterocycloalkyl groups.

[0067] In further embodiments, in organometallic compounds represented by any one of the general formulas (I) to (VII) specified above, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, or RN are optionally substituted linear or branched C1-C5 alkyl groups, optionally substituted C3-C5 cycloalkyl groups, or optionally substituted C3-C5 heterocycloalkyl groups, particularly optionally substituted linear C1-C5 alkyl groups, optionally substituted C3-C5 cycloalkyl groups, or optionally substituted C3-C5 heterocycloalkyl groups.

[0068] In further embodiments, in organometallic compounds represented by any one of the general formulas (I) to (VII) specified above, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, or RN are optionally substituted linear or branched C1-C4 alkyl groups, optionally substituted C3 or C4 cycloalkyl groups, or optionally substituted C3 or C4 heterocycloalkyl groups, in particular optionally substituted linear C1-C4 alkyl groups, optionally substituted C3 or C4 cycloalkyl groups, or optionally substituted C3 or C4 heterocycloalkyl groups.

[0069] In further embodiments, in organometallic compounds represented by any one of the general formulas (I) to (VII) specified above, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, or RN are optionally substituted linear or branched C1 to C3 alkyl groups, optionally substituted C3 cycloalkyl groups, or optionally substituted C3 heterocycloalkyl groups, particularly optionally substituted linear C1 to C3 alkyl groups, optionally substituted C3 cycloalkyl groups, or optionally substituted C3 heterocycloalkyl groups.

[0070] In additional embodiments, in organometallic compounds represented by any one of the general formulas (I) to (VII) specified above, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, or RN are optionally substituted C1 or C2 alkyl groups.

[0071] In organometallic compounds represented by any one of the general formulas (I) to (VII) identified above, R1, R2, R3, R4, R5, R6, R7, R8, or RN may be identical or different from each other. For ease of synthesis, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, or RN may be identical.

[0072] In a preferred embodiment, the organometallic compound is represented by one of the general formulas (a) to (j) shown in Figure 2. In a more preferred embodiment, the organometallic compound is represented by one of the formulas (a) to (o) shown in Figure 3A, or one of the formulas (p) to (ad) shown in Figure 3B. The compounds shown in Figures 3A and 3B include single, linear, and cyclic organometallic compounds relating to the general formulas (I), (II), (III), (IV), (VI), or (VII), where A = O, S, or NR, and n is 1 or 2, or m is 2 or 3.

[0073] Figure 2 shows a set of chemical structural diagrams representing organometallic compounds (a) through (j) for dry photoresists or hard masks for EUV lithography according to several embodiments. In compounds (a), (b), (c), (d), and (e), Bi is in oxidation state (III), and in compounds (f), (g), (h), (i), and (j), Bi is in oxidation state (V). In compounds (a) to (j), A represents a species selected from the group consisting of O, S, and NR; and the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, and R3 / 3 independently represent an optionally substituted linear or branched C1-C6 alkyl, an optionally substituted C3-C6 cycloalkyl, or an optionally substituted C3-C6 heterocycloalkyl. In NR, R represents H, or any optionally substituted linear or branched C1-C6 alkyl, an optionally substituted C3-C6 cycloalkyl, or an optionally substituted C3-C6 heterocycloalkyl. Note that in chemical structural diagrams, ligands shown as, for example, "R1,1" may be written as "R1 / 1".

[0074] In a more preferred modification, in an organometallic compound represented by any one of formulas (a) to (j) in Figure 2, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, or R3 / 3 are optionally substituted linear or branched C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, or optionally substituted C3-C6 heterocycloalkyl groups, particularly optionally substituted linear C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, or optionally substituted C3-C6 heterocycloalkyl groups.

[0075] In a more preferred modification, in an organometallic compound represented by any one of formulas (a) to (j) in Figure 2, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, or R3 / 3 are optionally substituted linear or branched C1-C5 alkyl groups, optionally substituted C3-C5 cycloalkyl groups, or optionally substituted C3-C5 heterocycloalkyl groups, particularly optionally substituted linear C1-C5 alkyl groups, optionally substituted C3-C5 cycloalkyl groups, or optionally substituted C3-C5 heterocycloalkyl groups.

[0076] In a more preferred modification, in an organometallic compound represented by any one of the general formulas (a) to (j) in Figure 2, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, or R3 / 3 are optionally substituted linear or branched C1-C4 alkyl groups, optionally substituted C3-C4 cycloalkyl groups, or optionally substituted C3-C4 heterocycloalkyl groups, particularly optionally substituted linear C1-C4 alkyl groups, optionally substituted C3 or C4 cycloalkyl groups, or optionally substituted C3 or C4 heterocycloalkyl groups.

[0077] In a more preferred modification, in an organometallic compound represented by any one of the general formulas (a) to (j) in Figure 2, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, or R3 / 3 are optionally substituted linear or branched C1 to C3 alkyl groups, optionally substituted C3 cycloalkyl groups, or optionally substituted C3 heterocycloalkyl groups, particularly optionally substituted linear C1 to C3 alkyl groups, optionally substituted C3 cycloalkyl groups, or optionally substituted C3 heterocycloalkyl groups.

[0078] In a more preferred modification, in an organometallic compound represented by any one of the general formulas (a) to (j) in Figure 2, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, or R3 / 3 are optionally substituted C1 or C2 alkyl groups.

[0079] Figure 3A shows a set of chemical structure diagrams (a) to (o) representing single, linear, and cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography according to several embodiments, where Bi is in oxidation state (III). In Figure 3A: (a) In general formula (I), A is O; (b) In general formula (II), A is O and n=1; (c) In general formula (II), A is O and n=2; (d) In general formula (III), A is O and m=2; (e) In general formula (III), A is O and m=3; (f) In general formula (I), A is S; (g) In general formula (II), A is S and n=1; (h) In general formula (II), A is S and n=2; (i) In general formula (III), A is S and m = 2; (j) In general formula (III), A is S and m = 3; (k) In general formula (I), A is NR; (l) In general formula (II), A is NR and n=1; (m) In general formula (II), A is NR and n=2; (n) In general formula (III), A is NR and m=2; and (o) In general formula (III), A is NR and m=3.

[0080] In the general formulas (a) to (o) shown in Figure 3A, R1, R2, R3, R4, R1 / 1, R1 / 2, R1 / 3, RN / 1, RN / 2, and RN / 3 can independently represent an optionally substituted linear or branched C1-C6 alkyl group, an optionally substituted C3-C6 cycloalkyl group, or an optionally substituted C3-C6 heterocycloalkyl group.

[0081] In a more preferred modification, in an organometallic compound represented by any one of formulas (a) to (o) in Figure 3A, the alkyl ligands R1, R1 / 1, R1 / 2, R1 / 3, RN / 1, RN / 2, and RN / 3 are optionally substituted linear or branched C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, or optionally substituted C3-C6 heterocycloalkyl groups, particularly optionally substituted linear C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, or optionally substituted C3-C6 heterocycloalkyl groups.

[0082] In a more preferred modification, in an organometallic compound represented by any one of formulas (a) to (o) in Figure 3A, the alkyl ligands R1, R1 / 1, R1 / 2, R1 / 3, RN / 1, RN / 2, and RN / 3 are optionally substituted linear or branched C1-C5 alkyl groups, optionally substituted C3-C5 cycloalkyl groups, or optionally substituted C3-C5 heterocycloalkyl groups, particularly optionally substituted linear C1-C5 alkyl groups, optionally substituted C3-C5 cycloalkyl groups, or optionally substituted C3-C5 heterocycloalkyl groups.

[0083] In a more preferred modification, in an organometallic compound represented by any one of formulas (a) to (o) in Figure 3A, the alkyl ligands R1, R1 / 1, R1 / 2, R1 / 3, RN / 1, RN / 2, and RN / 3 are optionally substituted linear or branched C1 to C4 alkyl groups, optionally substituted C3 to C4 cycloalkyl groups, or optionally substituted C3 to C4 heterocycloalkyl groups, particularly optionally substituted linear C1 to C4 alkyl groups, optionally substituted C3 or C4 cycloalkyl groups, or optionally substituted C3 or C4 heterocycloalkyl groups.

[0084] In a more preferred modification, in an organometallic compound represented by any one of formulas (a) to (o) in Figure 3A, the alkyl ligands R1, R1 / 1, R1 / 2, R1 / 3, RN / 1, RN / 2, and RN / 3 are optionally substituted linear or branched C1 to C3 alkyl groups, optionally substituted C3 cycloalkyl groups, or optionally substituted C3 heterocycloalkyl groups, particularly optionally substituted linear C1 to C3 alkyl groups, optionally substituted C3 cycloalkyl groups, or optionally substituted C3 heterocycloalkyl groups.

[0085] In a more preferred modification, in the organometallic compound represented by any one of formulas (a) to (o) in Figure 3A, the alkyl ligands R1, R1 / 1, R1 / 2, R1 / 3, RN / 1, RN / 2, and RN / 3 are optionally substituted C1 or C2 alkyl groups.

[0086] Figure 3B shows a set of chemical structure diagrams (p) to (ad) representing single, linear, and cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography according to several embodiments, where Bi is in the oxidation state (V). In Figure 3B: (p) In general formula (IV), A is O; (q) In general formula (VI), A is O and n=1; (r) In general formula (VI), A is O and n=2; (s) In general formula (VII), A is O and m=2; (t) In general formula (VII), A is O and m=3; (u) In general formula (IV), A is S; (v) In general formula (VI), A is S and n=1; (w) In general formula (VI), A is S and n=2; (x) In general formula (VII), A is S and m=2; (y) In general formula (VII), A is S and m = 3; (z) In general formula (IV), A is NR; (aa) In general formula (VI), A is NR and n=1; (ab) In general formula (VI), A is NR and n=2; (ac) In general formula (VII), A is NR and m=2; and (ad) In general formula (VII), A is NR and m=3.

[0087] In the general formulas (p) to (ad) shown in Figure 3B, where the bismuth element is Bi(V), each of R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 independently represents an arbitrarily substituted linear or branched C1 to C6 alkyl, an arbitrarily substituted C3 to C6 cycloalkyl, or an arbitrarily substituted heterocycloalkyl.

[0088] In a more preferred modification, in an organometallic compound represented by any one of formulas (p) to (ad) in Figure 3B, the alkyl ligands R1, R2, R3, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 are optionally substituted linear or branched C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, or optionally substituted C3-C6 heterocycloalkyl groups, particularly optionally substituted linear C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, or optionally substituted C3-C6 heterocycloalkyl groups.

[0089] In a more preferred modification, in an organometallic compound represented by any one of formulas (p) to (ad) in Figure 3B, the alkyl ligands R1, R2, R3, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 are optionally substituted linear or branched C1-C5 alkyl groups, optionally substituted C3-C5 cycloalkyl groups, or optionally substituted C3-C5 heterocycloalkyl groups, particularly optionally substituted linear C1-C5 alkyl groups, optionally substituted C3-C5 cycloalkyl groups, or optionally substituted C3-C5 heterocycloalkyl groups.

[0090] In a more preferred modification, in an organometallic compound represented by any one of formulas (p) to (ad) in Figure 3B, the alkyl ligands R1, R2, R3, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 are optionally substituted linear or branched C1-C4 alkyl groups, optionally substituted C3-C4 cycloalkyl groups, or optionally substituted C3-C4 heterocycloalkyl groups, particularly optionally substituted linear C1-C4 alkyl groups, optionally substituted C3 or C4 cycloalkyl groups, or optionally substituted C3 or C4 heterocycloalkyl groups.

[0091] In a more preferred modification, in an organometallic compound represented by any one of formulas (p) to (ad) in Figure 3B, the alkyl ligands R1, R2, R3, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 are optionally substituted linear or branched C1 to C3 alkyl groups, optionally substituted C3 cycloalkyl groups, or optionally substituted C3 heterocycloalkyl groups, particularly optionally substituted linear C1 to C3 alkyl groups, optionally substituted C3 cycloalkyl groups, or optionally substituted C3 heterocycloalkyl groups.

[0092] In a more preferred modification, in the organometallic compound represented by any one of formulas (p) to (ad) in Figure 3B, the alkyl ligands R1, R2, R3, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 are optionally substituted C1 or C2 alkyl groups.

[0093] Figures 4A to 5B are a set of chemical structure diagrams showing single organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (I) and (IV), according to several embodiments.

[0094] Figures 4A and 4B show particularly preferred single organometallic compounds represented by general formula (I) or (IV), where Bi is in oxidation state (III) or (V), A is O, S, or NR, and alkyl ligands R1, R2, and R3 are linear C1 to C4 alkyl groups (e.g., methyl, ethyl, propyl, or butyl). In Figure 4A: (a) Methylbismutanone; (b) Ethylbismutanone; (c) Propylbismutanone; (d) Butylbismutanone; (e) Methylbismutanthion; (f) Ethylbismutanthion; (g) Propylbismuththione; (h) Butylbismuththione; (i) Bi-Methylbismuthimine; (j) Bi-Ethylbismuthimine; (k) Bi-Propylbismuthimine; and (l) Bi-Butylbismuthimine. In Figure 4B: (a) Trimethyl-λ 5 -Bismuthon; (b) Triethyl-λ 5 -Bismuthon; (c) Tripropyl-λ 5 -Bismuthon; (d) Tributyl-λ 5 -Bismuthon; (e) Trimethyl-λ 5 -Bismuththione; (f) Triethyl-λ 5 -Bismuththione; (g) Tripropyl-λ 5 -Bismuththione; (h) Tributyl-λ 5 -Bismuththione; (i) Bi,Bi,Bi-Trimethyl-λ 5 -Bismuthimine; (j) Bi,Bi,Bi-Triethyl-λ 5 -Bismuthimine; (k) Bi,Bi,Bi-Tripropyl-λ 5 -Bismuthimine; and (l) Bi,Bi,Bi-Tributyl-λ 5 -Bismuthimine.

[0095] Figures 4C and 4D show particularly preferred single organometallic compounds represented by general formulas (I) and (IV), where Bi is in the oxidation state (III) or (V), A is O, S, or N-R, and the alkyl ligands R1, R2, and R3 are branched C3 or C4 alkyl (e.g., isopropyl or tert-butyl). In Figure 4C: (a) Propane-2-irbismutanone; (b)tert-butylbismutanone; (c) Propane-2-irbismutanthion; (d) tert-butylbismutanthion; (e) Bi-propane-2-ilbismutanimine; and (f)Bi-tert-butylbismutaneimine. In Figure 4D: (a) Tri(propane-2-yl)-λ 5 -Bismutanon; (b) Tri(tert-butyl)-λ 5 -Bismutanon; (c) Tri(propane-2-yl)-λ 5 - Bismutantion; (d) Tri(tert-butyl)-λ 5 - Bismutantion; (e)Bi,Bi,Bi-tri(propane-2-yl)-λ 5 -bismutanimin; and (f)Bi,Bi,Bi-tri(tert-butyl)-λ 5 -Bisumutanimin.

[0096] Figures 5A and 5B show preferred single organometallic compounds represented by general formula (I) or (IV), where Bi is in oxidation state (III) or (V), A is O, S, or NR, and alkyl ligands R1, R2, and R3 are cyclic C3 or C4 alkyl (e.g., cyclopropyl or cyclobutyl). In Figure 5A: (a) Cyclopropyl bismutanone; (b) Cyclobutylbismutanone; (c) Cyclopropyl bismutanthion; (d) Cyclobutylbismutanthion; (e) Bi-cyclopropylbismutanimine; and (f) Bi-cyclobutylbismutaneimine. In Figure 5B: (a) Tricyclopropyl-λ5 -Bismutanon; (b) Tricyclobutyl-λ 5 -Bismutanon; (c) Tricyclopropyl-λ 5 - Bismutantion; (d) Tricyclobutyl-λ 5 - Bismutantion; (e)Bi,Bi,Bi-tricyclopropyl-λ 5 -bismutanimin; and (f)Bi,Bi,Bi-tricyclobutyl-λ 5 -Bisumutanimin.

[0097] Figures 6A to 7B are a set of chemical structure diagrams showing linear organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (II), (V), and (VI), according to several embodiments.

[0098] Figures 6A and 6B show particularly preferred linear organometallic compounds represented by general formulas (II), (V), or (VI), where Bi is in oxidation state (III) or (V); A is O, S, or NR; n is 1 or 2; and alkyl ligands R1, R2, R3, R4, R5, R6, R7, and R8 are methyl groups. In further embodiments, the alkyl ligands may be ethyl, propyl, or butyl. In Figure 6A: (a) Dimethylbismutanyloxy(dimethyl)bismutane; (b) Bis(dimethylbismutanyloxy)(methyl)bismutane; (c) Dimethylbismutanylsulfanyl(dimethyl)bismutan; (d) Bis(dimethylbismutanylsulfanyl)(methyl)bismutane; (e) bis(dimethylbismutanyl)amine; and (f) Dimethylbismutanylamino(methyl)bismutanyl(dimethylbismutanyl)amine. In Figure 6B: (a) Tetramethyl-λ5 -bismutanyloxy(tetramethyl)-λ 5 -Bismutan; (b) Bis(tetramethyl-λ) 5 -bismutanyloxy)(trimethyl)-λ 5 -Bismutan; (c) Tetramethyl-λ 5 -bismutanylsulfanil(tetramethyl)-λ 5 -Bismutan; (d) Bis(tetramethyl-λ) 5 -bismutanylsulfanyl)(trimethyl)-λ 5 -Bismutan; (e) Bis(tetramethyl-λ) 5 -bismutanyl)amine; and (f) Tetramethyl-λ 5 -bismutanylamino(trimethyl)-λ 5 -bismutanyl)(tetramethyl-λ) 5 -Bismutanyl)amine.

[0099] Figures 7A and 7B show preferred linear organometallic compounds represented by general formulas (II), (V), or (VI), where Bi is in oxidation state (III) or (V); A is O, S, or NR; n is 1 or 2; and alkyl ligands R1, R2, R3, R4, R5, R6, R7, and R8 are cyclopropyl. In further embodiments, the alkyl ligand may be cyclobutyl. In Figure 7A: (a) Dicyclopropyl bismutanyloxy(dicyclopropyl)bismutan; (b) Bis(dicyclopropylbismutanyloxy)(cyclopropyl)bismutane; (c) Dicyclopropylbismutanylsulfanyl(dicyclopropyl)bismutan; (d) Bis(dicyclopropylbismutanylsulfanyl)(cyclopropyl)bismutane; (e) bis(dicyclopropylbismutanyl)amine; and (f) Dicyclopropylbismutanylamino(cyclopropyl)bismutanyl(dicyclopropylbismutanyl)amine. In Figure 7B: (a) Tetracyclopropyl-λ 5 -Bismutanyloxy(tetracyclopropyl)-λ 5 -Bismutan; (b) Bis(tetracyclopropyl-λ) 5 -bismutanyloxy)(tricyclopropyl)-λ 5 -Bismutan; (c) Tetracyclopropyl-λ 5 -Bismutanylsulfanil(tetracyclopropyl)-λ 5 -Bismutan; (d) Bis(tetracyclopropyl-λ) 5 -bismutanylsulfanil)(tricyclopropyl)-λ 5 -Bismutan; (e) Bis(tetracyclopropyl-λ) 5 -bismutanyl)amine; and (f) Tetracyclopropyl-λ 5 -Bismutanylamino(tricyclopropyl-λ) 5 -bismutanil)(tetracyclopropyl-λ 5 -Bismutanyl)amine.

[0100] Figures 8A to 9B are a set of chemical diagrams showing cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (III) and (VII), according to several embodiments.

[0101] Figures 8A and 8B show particularly preferred cyclic organometallic compounds represented by general formula (III) or (VII), where Bi is oxidation state (III) or (V); A is O, S, or NR; m is 2; and the alkyl ligands R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, and R3 / 2 are methyl, ethyl, propyl, or butyl. In Figure 8A: (a) 2,4-dimethyl-1,3,2,4-dioxadibismethane; (b) 2,4-diethyl-1,3,2,4-dioxadibismethane; (c) 2,4-dipropyl-1,3,2,4-dioxadibismethane; (d) 2,4-dibutyl-1,3,2,4-dioxadibismethane; (e) 2,4-dimethyl-1,3,2,4-dithiadibismethane; (f) 2,4-diethyl-1,3,2,4-dithiadibismethane; (g) 2,4-dipropyl-1,3,2,4-dithiadibismethane; (h)2,4-dibutyl-1,3,2,4-dithiadibismethane; (i) 2,4-dimethyl-1,3,2,4-diazadibismethane; (j)2,4-diethyl-1,3,2,4-diazadibismethane; (k)2,4-dipropyl-1,3,2,4-diazadibismethane; and (l) 2,4-dibutyl-1,3,2,4-diazadibismethane. In Figure 8B: (a) 2,2,2,4,4,4-Hexamethyl-1,3,2,4-Dioxadi-λ 5 -Bismethane; (b) 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dioxadi-λ 5 -Bismethane; (c) 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dioxadi-λ 5 -Bismethane; (d) 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Dioxadi-λ 5 -Bismethane; (e) 2,2,2,4,4,4-Hexamethyl-1,3,2,4-Dithiadi-λ 5 -Bismethane; (f) 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dithiadi-λ 5 -Bismethane; (g) 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dithiadi-λ 5 -Bismethane; (h)2,2,2,4,4,4-Hexabutyl-1,3,2,4-Dithiadi-λ 5 -Bismethane; (i) 2,2,2,4,4,4-Hexamethyl-1,3,2,4-Diazazi-λ 5 -Bismethane; (j)2,2,2,4,4,4-Hexaethyl-1,3,2,4-Diazazi-λ 5 -Bismethane; (k)2,2,2,4,4,4-Hexapropyl-1,3,2,4-Diazazi-λ 5 -bismethane; and (l)2,2,2,4,4,4-Hexabutyl-1,3,2,4-Diazazi-λ 5 - Bismethane.

[0102] Figures 9A and 9B show preferred cyclic organometallic compounds represented by general formula (III) or (VII), where Bi is oxidation state (III) or (V); A is O, S, or NR; m is 2; and the alkyl ligands R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, and R3 / 2 are cyclopropyl or cyclobutyl. In Figure 9A: (a) 2,4-dicyclopropyl-1,3,2,4-dioxadibismethane; (b) 2,4-dicyclobutyl-1,3,2,4-dioxadibismethane; (c) 2,4-dicyclopropyl-1,3,2,4-dithiadibismethane; (d) 2,4-dicyclobutyl-1,3,2,4-dithiadibismethane; (e) 2,4-dicyclopropyl-1,3,2,4-diazabismethane; and (f) 2,4-dicyclobutyl-1,3,2,4-diazadibismethane. In Figure 9B: (a) 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dioxadi-λ 5 -Bismethane; (b) 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Dioxadi-λ 5 -Bismethane; (c) 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dithiadi-λ 5 -Bismethane; (d) 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Dithiadi-λ 5 -Bismethane; (e) 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Diazazi-λ 5 -bismethane; and (f) 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Diazazi-λ 5 - Bismethane.

[0103] Figures 10A to 11B are a set of chemical structure diagrams showing cyclic organometallic compounds for dry photoresists or hard masks for EUV lithography, represented by general formulas (III) and (VII), according to several embodiments.

[0104] Figures 10A and 10B show particularly preferred cyclic organometallic compounds represented by general formula (III) or (VII), where Bi is oxidation state (III) or (V); A is O, S, or NR; m is 3; and the alkyl ligands R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, and R3 / 2 are methyl, ethyl, propyl, or butyl. In Figure 10A: (a) 2,4,6-trimethyl-1,3,5,2,4,6-trioxatribissane; (b) 2,4,6-triethyl-1,3,5,2,4,6-trioxatribissane; (c) 2,4,6-tripropyl-1,3,5,2,4,6-trioxatribissane; (d) 2,4,6-tributyl-1,3,5,2,4,6-trioxatribissane; (e) 2,4,6-trimethyl-1,3,5,2,4,6-trithiatribissane; (f) 2,4,6-triethyl-1,3,5,2,4,6-trithiatribissane; (g) 2,4,6-tripropyl-1,3,5,2,4,6-trithiatribissane; (h)2,4,6-tributyl-1,3,5,2,4,6-trithiatribissane; (i) 2,4,6-trimethyl-1,3,5,2,4,6-triazatribissane; (j)2,4,6-triethyl-1,3,5,2,4,6-triazatribissane; (k)2,4,6-tripropyl-1,3,5,2,4,6-triazatribissane; and (l)2,4,6-tributyl-1,3,5,2,4,6-triazatribissane. In Figure 10B: (a) 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxatri-λ 5 - Bisman; (b) 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 - Bisman; (c) 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ 5 - Bisman; (d) 2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-trioxatri-λ 5 - Bisman; (e) 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 - Bisman; (f) 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 - Bisman; (g) 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ 5 - Bisman; (h)2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-trithiatri-λ5 - Bisman; (i) 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatry-λ 5 - Bisman; (j)2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatri-λ 5 - Bisman; (k)2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatri-λ 5 -Bisman; and (l)2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-triazatry-λ 5 - Bisman.

[0105] Figures 11A and 11B show preferred cyclic organometallic compounds represented by general formula (III) or (VII), where Bi is oxidation state (III) or (V); A is O, S, or NR; m is 3; and the alkyl ligands R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, and R3 / 2 are cyclopropyl or cyclobutyl. In Figure 11A: (a) 2,4,6-tricyclopropyl-1,3,5,2,4,6-trioxatribissane; (b) 2,4,6-tricyclobutyl-1,3,5,2,4,6-trioxatribissane; (c) 2,4,6-tricyclopropyl-1,3,5,2,4,6-trithiatribissane; (d) 2,4,6-Tricyclobutyl-1,3,5,2,4,6-Tritiatribissane; (e) 2,4,6-tricyclopropyl-1,3,5,2,4,6-triazatribissane; and (f) 2,4,6-Tricyclobutyl-1,3,5,2,4,6-Triazatribissane. In Figure 11B: (a) 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 - Bisman; (b) 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trioxatri-λ 5 - Bisman; (c) 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ 5 - Bisman; (d) 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trithiatri-λ 5 - Bisman; (e) 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatri-λ 5 -Bisman; and (f) 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-triazatry-λ 5 - Bisman.

[0106] When A is NR, in the aforementioned preferred organometallic compounds of general formulas (I) to (VII), R or the R group (RN / 1, RN / 2, or RN / 3) is one of the following: H; a linear C1 to C4 alkyl such as methyl, ethyl, propyl, or butyl; or a branched C3 or C4 alkyl such as isopropyl or tert-butyl; or a cyclic C3 or C4 alkyl such as cyclopropyl or cyclobutyl. Preferably, R is the same as the alkyl ligand of the organometallic compound.

[0107] In the disclosed organometallic compounds for dry photoresists or hard masks for EUV lithography, the organometallic compound comprises Bi; one of a terminal oxo ligand, terminal thioxo ligand, terminal imino ligand, oxygen bridging ligand, sulfur bridging ligand, or aminoalkyl bridging ligand; and a C1 to C4 alkyl ligand, the molecular composition and structure can be advantageously selected as follows: (i) At room temperature, the diffusion coefficient of the molecules should be low. Therefore, the composition and structure of the molecules can be selected such that their melting point temperature is high. By means of a terminal oxo ligand, a terminal thioxo ligand, a terminal imino ligand, an oxygen-bridging ligand, a sulfur-bridging ligand, or an amino-bridging ligand, the melting point temperature of the molecules is substantially higher than room temperature even when the alkyl ligand is methyl (C1). By increasing the alkyl ligand length from C1 to C4, the melting point temperature can be further adjusted (e.g., to about 180 K). (ii) During EUV exposure, the Bi-C bond and the N-C bond dissociate, and an inorganic Bi=O cluster, a Bi-O cluster, a Bi=S cluster, a Bi-S cluster, a Bi=N cluster, or a Bi-N cluster crosslinks. The clusters are non-volatile. (iii) The alkyl ligand can be selected such that the reaction product during EUV exposure is volatile under the processing conditions in an EUV scanner, except for a Bi=O cluster, a Bi-O cluster, a Bi=S cluster, a Bi-S cluster, a Bi=N cluster, or a Bi-N cluster. Therefore, C1 to C4 alkyl ligands are preferred. (iv) The shrinkage due to the volatilization of the species during EUV exposure should be moderate. Therefore, C1 to C3 alkyl ligands are even more preferred as the alkyl ligand.

[0108] Regarding the diffusion coefficient (i), the diffusion coefficient in a solid is generally well predicted by exp(E A / kT) depending on the Arrhenius equation, where the activation energy E A for diffusion is proportional to the melting point temperature of the solid in a first-order approximation. Due to the exponential correlation between the diffusion coefficient and the melting point temperature, it has been found that the melting point temperature of organometallic molecules can be very important for selecting preferred organometallic molecules.

[0109] Therefore, preferred are organometallic molecules that are solids with a very low vapor pressure under the vacuum conditions found in an EUV scanner because of their high melting point temperature.

[0110] Melting point temperature T of a class of bismuthano organic metal molecules for dry photoresist or hard mask for EUV lithography M A reasonable estimate for can be obtained by considering and realizing the boiling point temperatures T B of the series of organometallic molecules tetraalkylstannane, trialkylstibane, and trialkylbismuthane. For example, the melting point temperature T M of dimethyloxotin is about 380 °C.

[0111] For tetramethylstannane and tetrapropylstannane, the respective boiling point temperatures T B are about 80 °C and 220 °C, and for trimethylstibane and tripropylstibane, the respective boiling point temperatures T B are about 80 °C and 210 °C, and for trimethylbismuthane and tripropylbismuthane, the respective boiling point temperatures T B are about 100 °C and 220 °C. It has been experimentally determined that tetraalkylstannane, trialkylstibane, and trialkylbismuthane organometallic molecules function similarly. Also, it has been experimentally found that for organometallic molecules with propyl ligands, the boiling point temperature T B increases by at least about 120 K compared to organometallic molecules with methyl ligands.

[0112] Based on these observations, the melting point temperature T M is about 380 °C when R is a C1 alkyl (e.g., trimethyl-λ 5 -bismuthano; 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxadi-λ 5 -bismethane; and 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismane), and about 500 °C when R is a C2 alkyl (e.g., triethyl-λ 5 -bismuthano; 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadi-λ 5 -bismethane; and 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ5 When R is C3 alkyl (e.g., tripropyl-λ), at approximately 440°C, R is C3 alkyl (e.g., tripropyl-λ). 5 -bismutanone; tri(propane-2-yl)-λ 5 -Bismutanone;tricyclopropyl-λ 5 -Bismutanone; 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dioxadi-λ 5 -Bismethane; 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dioxadi-λ 5 -Bismethane; 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismann; and 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 When R is C4 alkyl (e.g., tributyl-λ), it can reach approximately 500°C, and R is C4 alkyl (e.g., tributyl-λ). 5 -bismutanone; tri(tert-butyl)-λ 5 -Bismutanone;tricyclobutyl-λ 5 -Bismutanone; 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Dioxadi-λ 5 -Bismethane; 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Dioxadi-λ 5 -Bismethane; 2,2,2,4,4,4,6,6,6-Nonabutyl-1,3,5,2,4,6-Trioxatri-λ 5 -bisman; and 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trioxatri-λ 5 It was estimated that the temperature would reach approximately 560°C when the bismann (-) state was present.

[0113] Sulfide compounds generally have a melting point T similar (but slightly lower) to that of their corresponding oxides. M For example, Bi2S3 and Bi2O3 have melting points T of approximately 775°C and approximately 817°C, respectively. M It has the following characteristics: Therefore, the corresponding bismutanon for dry photoresist or hard mask for EUV lithography, and λ 5- Bismutanone, bismutanthion, λ 5 - Bismutanthion, bismutanimine, λ 5 -Bismutaneimine, 1,3,2,4-dioxadibismethane, 1,3,2,4-dioxadi-λ 5 -Bismethane, 1,3,5,2,4,6-trioxatribissane, 1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 1,3,2,4-Dithiadibismethane, 1,3,2,4-Dithiadi-λ 5 -Bismethane, 1,3,5,2,4,6-Trichiatribissane, 1,3,5,2,4,6-Trichiatri-λ 5 -Bisman, 1,3,2,4-diazadibismethane, 1,3,2,4-diazadi-λ 5 -Bismethane, 1,3,5,2,4,6-triazatlybissane, and 1,3,5,2,4,6-triazatly-λ 5 - Bismann organometallic molecules have similar melting point temperatures T M It was reasonable to assume that it had [this characteristic].

[0114] In a preferred embodiment, the organometallic compound for the dry photoresist or hard mask for EUV lithography has a melting point of at least 100°C. In a more preferred embodiment, the melting point of the organometallic compound is in the range of 300°C to 600°C. Such organometallic compounds are solids with very low vapor pressure under the vacuum conditions found in EUV scanners. Therefore, in terms of diffusion coefficient, the alkyl ligand or R group in the organometallic compound as defined in detail above is preferably a linear or branched C1 to C4 alkyl or a cyclic C1 to C4 alkyl, more preferably a linear or branched C2 to C4 alkyl or a cyclic C3 or C4 alkyl.

[0115] Regarding the bond dissociation (ii) of (Bi-C), abu initio gas-phase simulations of the bond energy (uniform dissociation energy) of organobismuth(V) molecules were performed at the Perdew-Burke-Esnzerof theory and the Perdew-Burke-Esnzerof and double-zeta valence polarizations (PBE / DZVP) theory levels. These simulations provide a detailed understanding of the predicted relative sensitivity of organometallic molecules for dry photoresists or hard masks for EUV lithography. In the following chemical formulas, Me refers to a methyl group, Et refers to an ethyl group, Pr refers to a propyl group, Bu refers to a butyl group, iPr refers to an isopropyl group, tBu refers to a tert-butyl group, cPr refers to a cyclopropyl group, and cBu refers to a cyclobutyl group.

[0116] trimethyl-λ 5 -Bismutanone, triethyl-λ 5 -Bismutanone, tripropyl-λ 5 -Bismutanone and tributyl-λ 5 -Simulations of the binding energy of bismutanone (Figure 4B) yielded the following: trimethyl-λ 5 - Bismutanone Bi-Me: 32kcal / mol Triethyl-λ 5 - Bismutanone Bi-Et: 29kcal / mol Tripropyl-λ 5 - Bismutanone Bi-Pr: 30kcal / mol Tributyl-λ 5 - Bismutanone Bi-Bu: 30kcal / mol

[0117] Tri(propane-2-yl)-λ 5 -Bismutanone and tri(tert-butyl)-λ 5 -Simulations of the binding energy of bismutanone (Figure 4D) yielded the following: Tri(propane-2-yl)-λ 5- Bismutanone Bi-iPr: 25kcal / mol Tri(tert-butyl)-λ 5 - Bismutanone Bi-tBu: 21kcal / mol

[0118] Due to their high bond energies, the compounds shown in Figure 4B may be preferable to those shown in Figure 4D.

[0119] Cyclopropyldimethyl-λ 5 -Bismutanone, tricyclopropyl-λ 5 -Bismutanone, cyclobutyldimethyl-λ 5 -Bismutanone and tricyclobutyl-λ 5 -Simulations of the binding energy of bismutanone (Figure 5B) yielded the following: Cyclopropyldimethyl-λ 5 - Bismutanone Bi-cPr: 35kcal / mol; Bi-Me: 33kcal / mol Tricyclopropyl-λ 5 - Bismutanone Bi-cPr: 35kcal / mol Cyclobutyldimethyl-λ 5 - Bismutanone Bi-cBu: 27kcal / mol; Bi-Me: 33kcal / mol Tricyclobutyl-λ 5 - Bismutanone Bi-cBu: 26kcal / mol

[0120] The λ shown in Figures 4B, 4D, and 5B 5 Based on the above-determined binding energies for the bismutanthion molecule series, it was found that the binding energies of the "bismutanthion" type molecules are identical to those of the corresponding "bismutanone" type molecules, within the limits of experimental uncertainty.

[0121] Organometallic compounds for dry photoresists or hard masks for EUV lithography, having a four-membered ring (Figures 8B and 9B) or a six-membered ring (Figures 10B and 11B), each have Bialkyl bond energies similar to the corresponding "bismutanone" type molecules shown in Figures 4B and 5B.

[0122] Organometallic compounds with bond energies of less than 30 kcal / mol (e.g., the compounds shown in Figure 4D) may be more unstable. Therefore, organometallic compounds with bond energies of less than 30 kcal / mol may be preferred in some embodiments.

[0123] In some embodiments, from the viewpoint of bond dissociation, the alkyl ligand or R group(s) in the organometallic compound as defined in detail above may preferably be a linear C1 to C4 alkyl, isobutyl (branched C4 alkyl), or cyclic C3 alkyl. For example, methyl (C1 alkyl) or cyclopropyl (cyclic C3 alkyl) may be preferred. In further embodiments, isopropyl (branched C3 alkyl), tert-butyl (C4 branched alkyl), sec-butyl (branched C4 alkyl), and cyclobutyl (cyclic C4 alkyl) may be preferred.

[0124] Regarding reaction product (iii), during EUV exposure, the Bi-C and NC bonds in the organometallic molecule dissociate, and inorganic Bi=O clusters, Bi=S clusters, Bi-O clusters, Bi-S clusters, Bi=N clusters, and Bi-N clusters crosslink (the clusters are non-volatile), and organic radicals react in pairs. For example, in trimethyloxobisumutane, the decomposition chemical reaction is n C3H9OBi→(BiO) n The reaction can proceed via +3n / 2C2H6. In trimethyloxobisumutane, a methyl radical reacts with it to form ethane. In another example, in tricyclobutyloxobisumutane, the decomposition reaction proceeds via nC 12 H 21 OBi→(BiO) n +3n / 2 C8H 14This can proceed by the following: In tricyclobutyloxobisumutane, cyclobutyl radicals react in pairs to form cyclobutylcyclobutane. Examples of organic products formed by paired radical reactions in some embodiments are as follows:

[0125] When R is methyl (C1 alkyl), the product of the paired radical reaction is ethane (C2), and its boiling point temperature at atmospheric pressure is T B The temperature is -89°C, and the vapor pressure at room temperature is approximately 4200 kPa. When R is ethyl (C2 alkyl), the product of the paired radical reaction is butane (C4), and its boiling point temperature at atmospheric pressure is T B The temperature is -1°C, and the room temperature vapor pressure is approximately 220 kPa.

[0126] When R is propyl (C3 alkyl), the product of the paired radical reaction is hexane (C6), with a boiling point temperature of T B The temperature is 69°C, and the vapor pressure at room temperature is approximately 20 kPa. When R is isopropyl (C3 alkyl), the product of the paired radical reaction is 2,4-dimethylpentane (C6), and its boiling point temperature at atmospheric pressure is T B The temperature is 80°C, and the room temperature vapor pressure is approximately 10 kPa. When R is cyclopropyl (C3 alkyl), the product of the paired radical reaction is cyclopropylcyclopropane (C6), and its boiling point temperature at atmospheric pressure is T B The temperature is approximately 70°C, and the room temperature vapor pressure is approximately 20kPa.

[0127] When R is butyl (C4 alkyl), the product of the paired radical reaction is octane (C8), with a boiling point temperature of T B The temperature is 126°C, and the vapor pressure at room temperature is approximately 2 kPa. When R is isobutyl (C4 alkyl), the product of the paired radical reaction is 2,2,4,4-tetramethylpentane (C8), with a boiling point temperature of T B The temperature is 122°C, and the room temperature vapor pressure is approximately 2 kPa. When R is cyclobutyl (C4 alkyl), the product of the paired radical reaction is cyclobutylcyclobutane (C8), with a boiling point temperature of T BThe temperature is approximately 130, and the room temperature vapor pressure is approximately 2 kPa.

[0128] EUV generating scanners, such as the ASML TWINSCAN NXE:3400C (manufactured by ASML Holding NV), typically have a background pressure of about 1 Pa. Therefore, linear or branched C2-C8 alkyl molecules and cyclic C6-C8 alkyl molecules are volatile under the processing conditions in the EUV scanner. Thus, from the viewpoint of reaction products, the alkyl ligand or R group in the organometallic compound as defined in detail above is preferably linear or branched C1-C4 alkyl or cyclic C3 or C4 alkyl. More preferably, at least one alkyl ligand or R group is linear or branched C1-C3 alkyl or cyclic C3 alkyl.

[0129] Regarding shrinkage (iv) during EUV exposure, numerical simulations of the molar volume of organobismuth(V) molecules were performed to gain an understanding of the shrinkage caused by the volatilization of the species during EUV exposure of disclosed organometallic molecules for dry photoresists or hard masks for EUV lithography.

[0130] trimethyl-λ 5 -Bismutanone, triethyl-λ 5 -Bismutanone, tripropyl-λ 5 -Bismutanone and tributyl-λ 5 -Bismutanone (Figure 4B), and tricyclopropyl-λ 5 -Bismutanone and tricyclobutyl-λ 5 - The ratio of the Bi=O cluster volume to the organic bismuth (V) molecular volume of bismuthtanone (Figure 5B) is as follows: trimethyl-λ 5 - Bismuthanone Volume ratio: 0.51 Triethyl-λ 5 - Bismuthanone Volume ratio: 0.35 Tricyclopropyl-λ 5 - Bismuthanone Volume ratio: 0.30 Tripropyl-λ 5- Bismuthanone Volume ratio: 0.27 Tricyclobutyl-λ 5 - Bismuthanone Volume ratio: 0.25 Tributyl-λ 5 - Bismuthanone Volume ratio: 0.22

[0131] trimethyl-λ 5 -Bismutanthion, triethyl-λ 5 -Bismutanthion, tripropyl-λ 5 -Bismutanthion and tributyl-λ 5 - Bismutanthion (Figure 4B), and tricyclopropyl-λ 5 -Bismutanthion and tricyclobutyl-λ 5 - The ratio of the Bi=S cluster volume to the organic bismuth (V) molecular volume of bismuth tanthion (Figure 5B) is as follows: trimethyl-λ 5 - Bismutanthion Volume ratio: 0.53 Triethyl-λ 5 - Bismutanthion Volume ratio: 0.38 Tricyclopropyl-λ 5 - Bismutanthion Volume ratio: 0.33 Tripropyl-λ 5 - Bismutanthion Volume ratio: 0.29 Tricyclobutyl-λ 5 - Bismutanthion Volume ratio: 0.27 Tributyl-λ 5 - Bismutanthion Volume ratio: 0.24

[0132] Hexaalkyl-1,3,2,4-dioxadi-λ 5 -Bismethane (m=2) and nonaalkyl-1,3,5,2,4,6-trioxatri-λ 5 - The ratio of the Bi=O cluster volume to the organic bismuth (V) molecular volume of bismann (m=3) is, within the range of experimental uncertainty, the corresponding trialkyl-λ 5 -Identical to the bismutanone molecule. Hexaalkyl-1,3,2,4-dithiadi-λ 5-Bismethane (m=2) and nonaalkyl-1,3,5,2,4,6-trithiatri-λ 5 - The ratio of the Bi=S cluster volume to the organic bismuth (V) molecular volume of bismann (m=3) is, within the range of experimental uncertainty, the corresponding trialkyl-λ 5 -Identical to the bismutanthion molecule. Based on these ratios, from the viewpoint of shrinkage, at least one alkyl ligand or R group in the organometallic compound as defined in detail above is preferably a linear or branched C1 to C3 alkyl or a cyclic C3 alkyl. More preferably, the R group is a C1 or C2 alkyl in some embodiments.

[0133] Due to the above properties / effects, organometallic compounds for dry photoresists or hard masks for EUV lithography are preferably methylbismutanone, ethylbismutanone, propylbismutanone, butylbismutanone, methylbismutanthion, ethylbismutanthion, propylbismutanthion, butylbismutanthion, Bi-methylbismutanimine, Bi-ethylbismutanimine, Bi-propylbismutanimine, Bi-butylbismutanimine, trimethyl-λ 5 -Bismutanone, triethyl-λ 5 -Bismutanone, tripropyl-λ 5 -Bismutanone, tributyl-λ 5 -Bismutanone, trimethyl-λ 5 -Bismutanthion, triethyl-λ 5 -Bismutanthion, tripropyl-λ 5 -Bismutanthion, tributyl-λ 5 -Bismutanthion, Bi,Bi,Bi-trimethyl-λ 5 -Bismutanimine, Bi,Bi,Bi-triethyl-λ 5 -Bismutaneimine, Bi,Bi,Bi-tripropyl-λ 5 -Bismutaneimine, Bi,Bi,Bi-tributyl-λ 5-Bismutanimine, propane-2-ylbismutanone, tert-butylbismutanone, propane-2-ylbismutanthion, tert-butylbismutanthion, Bi-propane-2-ylbismutanimine, Bi-tert-butylbismutanimine, tri(propane-2-yl)-λ 5 -Bismutanone, tri(tert-butyl)-λ 5 -bismutanone, tri(propane-2-yl)-λ 5 -Bismutanthion, tri(tert-butyl)-λ 5 -Bismutanthion, Bi,Bi,Bi-tri(propane-2-yl)-λ 5 -Bismutaneumimine, Bi,Bi,Bi-tri(tert-butyl)-λ 5 - Bismutanimine, cyclopropylbismutanone, cyclobutylbismutanone, cyclopropylbismutanthion, cyclobutylbismutanthion, Bi-cyclopropylbismutanimine, Bi-cyclobutylbismutanimine, tricyclopropyl-λ 5 -Bismutanone, tricyclobutyl-λ 5 -Bismutanone, tricyclopropyl-λ 5 -Bismutanthion, tricyclobutyl-λ 5 -Bismutanthion, Bi,Bi,Bi-tricyclopropyl-λ 5 -Bismutaneimine, Bi,Bi,Bi-tricyclobutyl-λ 5-Bismutanimine, Dimethylbismutanyloxy(dimethyl)bismutan, Bis(dimethylbismutanyloxy)(methyl)bismutan, Dimethylbismutanylsulfanyl(dimethyl)bismutan, Bis(dimethylbismutanylsulfanyl)(methyl)bismutan, Bis(dimethylbismutanyl)amine, Dimethylbismutanylamino(methyl)bismutanyl(dimethylbismutanyl)amine, Diethylbismutanyloxy(diethyl)bismutan, Bis(diethylbismutanyloxy)(ethyl)bismutan, Diethylbismutanylsulfanyl(diethyl)bismutan, Bis(diethylbismutanylsulfanyl)(ethyl)bismutan, Bis(diethylbismutanyl)amine, Diethylbismutanylamino(ethyl)bismutanyl(diethylbismutanyl)amine, Dipro Pyrbismutanyloxy(dipropyl)bismutan, bis(dipropylbismutanyloxy)(propyl)bismutan, dipropylbismutanylsulfanyl(dipropyl)bismutan, bis(dipropylbismutanylsulfanyl)(propyl)bismutan, bis(dipropylbismutanyl)amine, dipropylbismutanylamino(propyl)bismutanyl(dipropylbismutanyl)amine, dibutylbismutanyloxy(dibutyl)bismutan, bis(dibutylbismutanyloxy)(butyl)bismutan, dibutylbismutanylsulfanyl(dibutyl)bismutan, bis(dibutylbismutanylsulfanyl)(butyl)bismutan, bis(dibutylbismutanylamine), dibutylbismutanylamino(butyl)bismutanyl(dibutylbismutanyl, tetramethyl-λ 5 -bismutanyloxy(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyloxy)(trimethyl)-λ 5 -Bismutane, tetramethyl-λ 5 -bismutanylsulfanil(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanylsulfanyl)(trimethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyl)amine, tetramethyl-λ5 -bismutanylamino(trimethyl)-λ 5 -bismutanyl)(tetramethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanyloxy(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanyloxy)(triethyl)-λ 5 -Bismutane, tetraethyl-λ 5 -bismutanylsulfanyl(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanylsulfanyl)(triethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanylamino(triethyl)-λ 5 -bismutanyl)(tetraethyl-λ) 5 -Bismutanyl)amine, tetrapropyl-λ 5 -bismutanyloxy(tetrapropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -bismutanyloxy)(tripropyl)-λ 5 -Bismutane, tetrapropyl-λ 5 -Bismutanylsulfanil(tetrapropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -bismutanylsulfanil)(tripropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -Bismutanyl)amine, tetrapropyl-λ 5 -bismutanylamino(tripropyl)-λ 5 -bismutanil)(tetrapropyl-λ 5 -bismutanyl)amine, tetrabutyl-λ 5 -bismutanyloxy(tetrabutyl)-λ 5 -Bismutane, bis(tetrabutyl-λ) 5 -bismutanyloxy)(tributyl)-λ 5-Bismutane, tetrabutyl-λ 5 -bismutanylsulfanil(tetrabutyl)-λ 5 -Bismutane, bis(tetrabutyl-λ) 5 -bismutanylsulfanyl)(tributyl)-λ 5 -Bismutane, bis(tetrabutyl-λ) 5 -bismutanyl)amine, tetrabutyl-λ 5 -bismutanylamino(tributyl)-λ 5 -bismutanil)(tetrabutyl-λ) 5 -bismutanyl)amine, dicyclopropylbismutanyloxy(dicyclopropyl)bismutan, bis(dicyclopropylbismutanyloxy)(cyclopropyl)bismutan, dicyclopropylbismutanylsulfanyl(dicyclopropyl)bismutan, bis(dicyclopropylbismutanylsulfanyl)(cyclopropyl)bismutan, bis(dicyclopropylbismutanyl)amine, dicyclopropylbismutanylamino(cyclopropyl)bismutanyl(dicyclopropylbismutanyl)amine, dicyclobutylbismutanyloxy(dicyclobutyl)bismutan, bis(dicyclobutylbismutanyloxy)(cyclobutyl)bismutan, dicyclobutylbismutanylsulfanyl(dicyclobutyl)bismutan, bis(dicyclobutylbismutanylsulfanyl)(cyclobutyl)bismutan, bis(dicyclobutylbismutanyl)amine, dicyclobutylbismutanylamino(cyclobutyl)bismutanyl(dicyclobutylbismutanyl)-amine, tetracyclopropyl-λ 5 -Bismutanyloxy(tetracyclopropyl)-λ 5 -Bismutane, bis(tetracyclopropyl-λ) 5 -bismutanyloxy)(tricyclopropyl)-λ 5 -Bismutane, tetracyclopropyl-λ 5 -Bismutanylsulfanil(tetracyclopropyl)-λ 5 -Bismutane, bis(tetracyclopropyl-λ) 5 -bismutanylsulfanil)(tricyclopropyl)-λ 5 -Bismutane, bis(tetracyclopropyl-λ)5 -bismutanyl)amine, tetracyclopropyl-λ 5 -Bismutanylamino(tricyclopropyl)-λ 5 -bismutanil)(tetracyclopropyl-λ 5 -bismutanyl)amine, tetracyclobutyl-λ 5 -bismutanyloxy(tetracyclobutyl)-λ 5 -Bismutane, bis(tetracyclobutyl-λ) 5 -bismutanyloxy)(tricyclobutyl)-λ 5 -Bismutane, tetracyclobutyl-λ 5 -bismutanylsulfanil(tetracyclobutyl)-λ 5 -Bismutane, bis(tetracyclobutyl-λ) 5 -bismutanylsulfanil)(tricyclobutyl)-λ 5 -Bismutane, bis(tetracyclobutyl-λ) 5 -bismutanyl)amine, tetracyclobutyl-λ 5 -bismutanylamino(tricyclobutyl)-λ 5 -bismutanil)(tetracyclobutyl-λ) 5 -Bismutanyl)amine, 2,4-dimethyl-1,3,2,4-dioxadibismethane, 2,4-diethyl-1,3,2,4-dioxadibismethane, 2,4-dipropyl-1,3,2,4-dioxadibismethane, 2,4-dibutyl-1,3,2,4-dioxadibismethane, 2,4-dimethyl-1,3,2,4-dithiadibismethane, 2,4-diethyl-1,3,2,4-dithiadibismethane, 2,4-dipropyl- 1,3,2,4-Dithiadibismethane, 2,4-Dibutyl-1,3,2,4-Dithiadibismethane, 2,4-Dimethyl-1,3,2,4-Dizadibismethane, 2,4-Diethyl-1,3,2,4-Dizadibismethane, 2,4-Dipropyl-1,3,2,4-Dizadibismethane, 2,4-Dibutyl-1,3,2,4-Dizadibismethane, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dioxadi-λ 5-Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,4-dicyclopropyl-1,3,2,4-dioxadivismethane, 2,4-dicyclobutyl-1,3,2,4-dioxa Dibismethane, 2,4-dicyclopropyl-1,3,2,4-dithiadibismethane, 2,4-dicyclobutyl-1,3,2,4-dithiadibismethane, 2,4-dicyclopropyl-1,3,2,4-diazabismethane, 2,4-dicyclobutyl-1,3,2,4-diazadibismethane, 2,2,2,4,4,4-hexacyclopropyl-1,3,2,4-dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Dithiadi-λ 5-Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-triethyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-tripropyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-tributyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiatribissane, 2,4,6-triethyl-1,3,5,2,4,6-trithiatribissane, 2,4,6-tripropyl-1,3, 5,2,4,6-Tritiatribissane, 2,4,6-Tributyl-1,3,5,2,4,6-Tritiatribissane, 2,4,6-Trimethyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Triethyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Tripropyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Tributyl-1,3,5,2,4,6-Triazatribissane, 2,2,2,4,4,6,6,6-Nonamethyl-1,3,5,2,4,6-Trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ 5-Bismann, 2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-triazatry-λ 5 -bissman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trioxatribissman, 2,4,6-tricyclobutyl-1,3,5,2,4,6-trioxatribissman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trithiatribissman, 2,4,6-tricyclobutyl-1,3,5,2,4,6-trithiatribissman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-triazatribissman, 2,4,6-tricyclobutyl-1,3,5,2,4,6-triazatribissman, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismann, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ 5 -bismann, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatri-λ 5 -Bisman, and 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-triazatry-λ 5 - Can be selected from Bisman.

[0134] In a more preferred modification, the organometallic compound for the dry photoresist or hard mask for EUV lithography can be selected from the following: methylbismutanone, ethylbismutanone, propylbismutanone, methylbismutanthion, ethylbismutanthion, propylbismutanthion, Bi-methylbismutanimine, Bi-ethylbismutanimine, Bi-propylbismutanimine, trimethyl-λ 5 -Bismutanone, triethyl-λ 5 -Bismutanone, tripropyl-λ 5 -Bismutanone, trimethyl-λ 5 -Bismutanthion, triethyl-λ 5 -Bismutanthion, tripropyl-λ 5 -Bismutanthion, Bi,Bi,Bi-trimethyl-λ 5 -Bismutanimine, Bi,Bi,Bi-triethyl-λ 5 -Bismutaneimine, Bi,Bi,Bi-tripropyl-λ 5 - Bismutanimine, cyclopropylbismutanone, cyclopropylbismutanthion, Bi-cyclopropylbismutanimine, tricyclopropyl-λ 5 -Bismutanone, tricyclopropyl-λ 5 -Bismutanthion, Bi,Bi,Bi-tricyclopropyl-λ 5-Bismutanimine, Dimethylbismutanyloxy(dimethyl)bismutan, Bis(dimethylbismutanyloxy)(methyl)bismutan, Dimethylbismutanylsulfanyl(dimethyl)bismutan, Bis(dimethylbismutanylsulfanyl)(methyl)bismutan, Bis(dimethylbismutanyl)amine, Dimethylbismutanylamino(methyl)bismutanyl(dimethylbismutanyl)amine, Diethylbismutanyloxy(diethyl)bismutan, Bis(diethylbismutanyloxy)(ethyl)bismutan, Diethylbismutanylsulfanyl(diethyl)bismutan, Bis(diethylbis Mutanylsulfanyl(ethyl)bismutan, bis(diethylbismutanyl)amine, diethylbismutanylamino(ethyl)bismutanyl(diethylbismutanyl)amine, dipropylbismutanyloxy(dipropyl)bismutan, bis(dipropylbismutanyloxy)(propyl)bismutan, dipropylbismutanylsulfanyl(dipropyl)bismutan, bis(dipropylbismutanylsulfanyl)(propyl)bismutan, bis(dipropylbismutanyl)amine, dipropylbismutanylamino(propyl)bismutanyl(dipropylbismutanyl)amine, tetramethyl-λ 5 -bismutanyloxy(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyloxy)(trimethyl)-λ 5 -Bismutane, tetramethyl-λ 5 -bismutanylsulfanil(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanylsulfanyl)(trimethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyl)amine, tetramethyl-λ 5 -bismutanylamino(trimethyl)-λ 5 -bismutanyl)(tetramethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanyloxy(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ)5 -bismutanyloxy)(triethyl)-λ 5 -Bismutane, tetraethyl-λ 5 -bismutanylsulfanyl(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanylsulfanyl)(triethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanylamino(triethyl)-λ 5 -bismutanyl)(tetraethyl-λ) 5 -Bismutanyl)amine, tetrapropyl-λ 5 -bismutanyloxy(tetrapropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -bismutanyloxy)(tripropyl)-λ 5 -Bismutane, tetrapropyl-λ 5 -Bismutanylsulfanil(tetrapropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -bismutanylsulfanil)(tripropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -Bismutanyl)amine, tetrapropyl-λ 5 -bismutanylamino(tripropyl)-λ 5 -bismutanil)(tetrapropyl-λ 5 -bismutanyl)amine, dicyclopropylbismutanyloxy(dicyclopropyl)bismutan, bis(dicyclopropylbismutanyloxy)(cyclopropyl)bismutan, dicyclopropylbismutanylsulfanyl(dicyclopropyl)bismutan, bis(dicyclopropylbismutanylsulfanyl)(cyclopropyl)bismutan, bis(dicyclopropylbismutanyl)amine, dicyclopropylbismutanylamino(cyclopropyl)bismutanyl(dicyclopropylbismutanyl)amine, tetracyclopropyl-λ 5 -Bismutanyloxy(tetracyclopropyl)-λ 5-Bismutane, bis(tetracyclopropyl-λ) 5 -bismutanyloxy)(tricyclopropyl)-λ 5 -Bismutane, tetracyclopropyl-λ 5 -Bismutanylsulfanil(tetracyclopropyl)-λ 5 -Bismutane, bis(tetracyclopropyl-λ) 5 -bismutanylsulfanil)(tricyclopropyl)-λ 5 -Bismutane, bis(tetracyclopropyl-λ) 5 -bismutanyl)amine, tetracyclopropyl-λ 5 -Bismutanylamino(tricyclopropyl)-λ 5 -bismutanil)(tetracyclopropyl-λ 5 -Bismutanyl)amine, 2,4-dimethyl-1,3,2,4-dioxadibismethane, 2,4-diethyl-1,3,2,4-dioxadibismethane, 2,4-dipropyl-1,3,2,4-dioxadibismethane, 2,4-dimethyl-1,3,2,4-dithiadibismethane, 2,4-diethyl-1,3,2,4-dithiadibismethane, 2,4-dipropyl-1,3,2,4-dithiadibismethane, 2,4-dimethyl-1,3,2,4-diazadibismethane, 2,4-diethyl-1,3,2,4-diazadibismethane, 2,4-dipropyl-1,3,2,4-diazadibismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazadi-λ 5-Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,4-dicyclopropyl-1,3,2,4-dioxadibismethane, 2,4-dicyclopropyl-1,3,2,4-dithiadibismethane, 2,4-dicyclopropyl-1,3,2,4-diazabismethane, 2,2,2,4,4,4-hexacyclopropyl-1,3,2,4-dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-triethyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-tripropyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-triethyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-Tripropyl-1,3,5,2,4,6-Tritiatribissane, 2,4,6-Trimethyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Triethyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Tripropyl-1,3,5,2,4,6-Triazatribissane, 2,2,2,4,4,4,6,6,6-Nonamethyl-1,3,5,2,4,6-Trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatry-λ 5 -Bisman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trioxatribisman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trithiatribisman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-triazatribisman, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ 5 -Bisman, and 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatry-λ 5 - Bisman.

[0135] In the most preferred modification, the organometallic compound for the dry photoresist or hard mask for EUV lithography can be selected from the following: methylbismutanone, ethylbismutanone, methylbismutanthion, ethylbismutanthion, Bi-methylbismutanimine, Bi-ethylbismutanimine, trimethyl-λ 5 -Bismutanone, triethyl-λ 5 -Bismutanone, trimethyl-λ 5 -Bismutanthion, triethyl-λ 5 -Bismutanthion, Bi,Bi,Bi-trimethyl-λ 5 -Bismutanimine, Bi,Bi,Bi-triethyl-λ 5-Bismutanimine, Dimethylbismutanyloxy(dimethyl)bismutan, Bis(dimethylbismutanyloxy)(methyl)bismutan, Dimethylbismutanylsulfanyl(dimethyl)bismutan, Bis(dimethylbismutanylsulfanyl)(methyl)bismutan, Bis(dimethylbismutanyl)amine, Dimethylbismutanylamino(methyl)bismutanyl(dimethylbismutanyl)amine, Diethylbismutanyloxy(diethyl)bismutan, Bis(diethylbismutanyloxy)(ethyl)bismutan, Diethylbismutanylsulfanyl(diethyl)bismutan, Bis(diethylbismutanylsulfanyl)(ethyl)bismutan, Bis(diethylbismutanyl)amine, Diethylbismutanylamino(ethyl)bismutanyl(diethylbismutanyl)amine, Tetramethyl-λ 5 -bismutanyloxy(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyloxy)(trimethyl)-λ 5 -Bismutane, tetramethyl-λ 5 -bismutanylsulfanil(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanylsulfanyl)(trimethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyl)amine, tetramethyl-λ 5 -bismutanylamino(trimethyl)-λ 5 -bismutanyl)(tetramethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanyloxy(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanyloxy)(triethyl)-λ 5 -Bismutane, tetraethyl-λ 5 -bismutanylsulfanyl(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanylsulfanyl)(triethyl)-λ 5-Bismutane, bis(tetraethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanylamino(triethyl)-λ 5 -bismutanyl)(tetraethyl-λ) 5 -bismutanyl)amine, 2,4-dimethyl-1,3,2,4-dioxadibismethane, 2,4-diethyl-1,3,2,4-dioxadibismethane, 2,4-dimethyl-1,3,2,4-dithiadibismethane, 2,4-diethyl-1,3,2,4-dithiadibismethane, 2,4-dimethyl-1,3,2,4-diazadibismethane, 2,4-diethyl-1,3,2,4-diazadibismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-triethyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiatribissane, 2,4,6-triethyl-1,3,5,2,4,6-trithiatribissane, 2,4,6-trimethyl-1,3,5,2,4,6-triazatribissane, 2,4,6-triethyl-1,3,5,2,4,6-triazatribissane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5-Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann and 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatry-λ 5 - Bisman.

[0136] For the synthesis of organometallic compounds for dry photoresists or hard masks for EUV lithography, an example concerning trimethylbismutine oxide compounds is described. A benzene solution of trimethylbismutine dichloride (1.072 g, 3.3 mmol) was mixed with a freshly prepared aqueous solution of silver oxide (0.773 g, 3.3 mmol), and the resulting mixture was stirred in the dark at room temperature for 5 hours. The benzene layer was separated by decantation, placed on a molecular sieve for 12 hours, filtered, and condensed by evaporation. By slowly adding petroleum ether, trimethylbismutine oxide (40%) precipitated from the condensed benzene.

[0137] Organometallic compounds for dry photoresists or hard masks for EUV lithography can be combined with solvents. Examples of such solvents may include ethers (e.g., tetrahydrofuran), glycol ethers (e.g., 2-methoxyethyl ether (diglym)), ethylene glycol monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate (PGMEA), etc.), aromatic hydrocarbons (e.g., toluene, xylene, benzene, etc.), ketones (e.g., methyl isobutyl ketone, 2-heptanone, cycloheptanone, cyclohexanone, etc.), esters (e.g., ethyl lactate, ethoxyethylpropionic acid, etc.), and similar compounds. Solvent systems comprising mixtures of two or more of the aforementioned solvents are also contemplated herein.

[0138] Embodiments of the present disclosure may include dry photoresist or hard mask compositions for EUV lithography comprising at least one of the organometallic compounds described herein, as well as dry photoresist or hard masks comprising such compositions. In some embodiments, the disclosed organometallic compounds can undergo chemical transformation upon exposure of the dry photoresist or hard mask composition, particularly upon EUV irradiation, thereby creating a difference in solubility of the dry photoresist or hard mask between exposed and unexposed areas.

[0139] In some embodiments, the content of organometallic compounds in the photoresist or hard mask composition is preferably about 5 to 95% by weight, more preferably 10 to 90% by weight, and most preferably 20 to 80% by weight, based on the total weight of the photoresist or hard mask for EUV lithography. The photoresist or hard mask composition may contain a solvent or solvent mixture capable of dissolving the organometallic compounds. Examples of such solvents include, but are not limited to, ethers, glycol ethers, aromatic hydrocarbons, ketones, esters, and similar (see above). In addition, the photoresist or hard mask composition for EUV lithography may also contain other components such as photosensitizers, pigments, fillers, antistatic agents, flame retardants, defoamers, light stabilizers, antioxidants, or other additives. Combinations or mixtures of these other components may be used if desired.

[0140] Figure 12 is a flowchart of a process 100, according to several embodiments, for forming patterned material features on a substrate using a dry photoresist or hard mask composition. Process 100 may include a lithography process for creating patterned material layer structures, such as metal wiring lines, holes for contacts or vias, insulating areas (e.g., damascene trenches or shallow trench isolations), trenches for capacitor structures, and ion-implanted semiconductor structures for transistors, which may be used in integrated circuit devices.

[0141] A material surface can be provided on the substrate, as shown in operation 110. The substrate can be any suitable substrate conventionally used in processes involving photoresists. For example, the substrate may be silicon, silicon oxide, aluminum, aluminum oxide, gallium arsenide, ceramic, quartz, copper, or a combination thereof, comprising multiple layers. The material surface may include a metal conductive layer, a ceramic insulating layer, a semiconductor layer, or other materials, depending on the stage of the manufacturing process and the desired material to be set in the finished product.

[0142] A layer of the disclosed dry photoresist or hard mask composition can be formed on a material surface. This is shown in operation 120. By patterning the layer with energy rays, a pattern of irradiation / exposure regions can be created in the dry photoresist or hard mask layer. This is shown in operation 130. In some embodiments, the energy rays used to pattern the photoresist composition are EUV rays. When exposed with EUV irradiation, organometallic compounds can crosslink and create an insoluble network that remains on the substrate as a patterned material layer structure. Then, a portion of the layer can be selectively removed to form an exposed portion of the material surface. This is shown in operation 140. In some embodiments, after exposure, a photoresist structure with the desired pattern can be obtained or developed by a dry photoresist processing step. Examples of dry photoresist processing steps that can be used may include thermal processing steps, plasma ashing, plasma etching, and the like.

[0143] In other embodiments, after exposure, a photoresist structure with the desired pattern can be obtained or developed by contacting the photoresist layer with an alkaline aqueous solution, which selectively dissolves the areas of the photoresist exposed to irradiation (or the unexposed areas in the case of a negative photoresist) in the case of a positive photoresist. Some alkaline aqueous solutions or developers contain an aqueous solution of tetramethylammonium hydroxide. The resulting lithographic structure on the substrate can then be dried and all remaining developer removed. If a topcoat is used, it can be dissolved by the developer at this stage.

[0144] Process 100 may also include a step of forming patterned material features by etching or ion implanting exposed portions of the material. This is shown in operation 150. Patterns from the photoresist structure can be transferred to exposed portions of the substrate substrate material by etching with a suitable etching solution using techniques known in the art. In some embodiments, the transfer is performed by reactive ion etching or wet etching. Once the desired pattern has been transferred, all remaining photoresist can be removed using conventional stripping techniques. Alternatively, the pattern can be transferred by ion implantation to form a pattern of ion-implanted material.

[0145] Although the invention has been described with reference to specific embodiments, it should be understood that the invention is not limited to these examples, and many variations of these embodiments can be readily conceived by those skilled in the art after reading this disclosure. Therefore, the invention can be further illustrated, without limitation, by the following embodiments. The following embodiments may include preferred embodiments. Accordingly, as used herein, the term “clause” may refer to such “preferred embodiments.”

[0146] Clause 1: An organometallic compound for dry photoresist or hard mask for EUV lithography comprising: at least one Bi(III) and Bi(V) element; at least one terminal or bridging ligand A bonded to the Bi(III) and Bi(V) element, wherein ligand A is O, S, or NR, and the R group in NR is selected from the group consisting of H and C1 to C6 alkyl; and at least one C1 to C6 alkyl ligand bonded to the Bi(III) and Bi(V) element.

[0147] Clause 2: An organometallic compound according to Clause 1, having general formula (I), (II), (III), (IV), (V), (VI), or (VII) as shown above, where A represents an element selected from the group consisting of O, S, and NR; R1, R2, R3, R4, R5, R6, R7, or R8 independently represent an unsubstituted or substituted linear or branched C1-C6 alkyl, an unsubstituted or substituted C3-C6 cycloalkyl, or an unsubstituted or substituted C3-C6 heterocycloalkyl; n is an integer from 1 to 4; m is an integer from 2 to 5; and R in NR represents H, or any of the following: an unsubstituted or substituted linear or branched C1-C6 alkyl, an unsubstituted or substituted C3-C6 cycloalkyl, or an unsubstituted or substituted C3-C6 heterocycloalkyl.

[0148] Clause 3: The organometallic compounds described in Clause 2, where n is an integer from 1 to 3 and m is an integer from 2 to 4.

[0149] Clause 4: The organometallic compound is represented by any one of the formulas (a) to (o) shown in Figure 3A, where R1, R2, R3, R4, R1 / 1, R1 / 2, R1 / 3, RN / 1, RN / 2, and RN / 3 independently represent an unsubstituted or substituted linear or branched C1-C6 alkyl, an unsubstituted or substituted C3-C6 cycloalkyl, or an unsubstituted or substituted C3-C6 heterocycloalkyl; or the organometallic compound is represented by any one of the formulas (p) to (ad) shown in Figure 3B An organometallic compound according to any one of claims 1 to 3, represented by any one of the following: R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3, independently of each other, representing an unsubstituted or substituted linear or branched C1 to C6 alkyl, an unsubstituted or substituted C3 to C6 cycloalkyl, or an unsubstituted or substituted C3 to C6 heterocycloalkyl.

[0150] Clause 5: An organometallic compound according to any one of Clauses 2 to 4, wherein R1, R2, R3, R4, R5, R6, R7, and R8 in general formulas (I) to (VII) or R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 in general formulas (a) to (ad) is an unsubstituted or substituted linear or branched C1 to C5 alkyl, an unsubstituted or substituted C3 to C5 cycloalkyl, or an unsubstituted or substituted C3 to C5 heterocycloalkyl, in particular an unsubstituted or substituted linear C1 to C5 alkyl.

[0151] Clause 6: An organometallic compound according to any one of Clauses 2 to 5, wherein R1, R2, R3, R4, R5, R6, R7, and R8 in general formulas (I) to (VII) or R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 in general formulas (a) to (ad) is an unsubstituted or substituted linear or branched C1 to C4 alkyl, an unsubstituted or substituted C3 or C4 cycloalkyl, or an unsubstituted or substituted C3 or C4 heterocycloalkyl, in particular an unsubstituted or substituted linear C1 to C4 alkyl.

[0152] Clause 7: An organometallic compound according to any one of Clauses 2 to 6, wherein R1, R2, R3, R4, R5, R6, R7, and R8 in general formulas (I) to (VII) or R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 in general formulas (a) to (ad) is an unsubstituted or substituted linear or branched C1 to C3 alkyl, an unsubstituted or substituted C3 cycloalkyl, or an unsubstituted or substituted C3 heterocycloalkyl, in particular an unsubstituted or substituted linear C1 to C3 alkyl.

[0153] Clause 8: An organometallic compound according to any one of Clauses 2 to 7, wherein R1, R2, R3, R4, R5, R6, R7, and R8 in general formulas (I) to (VII) or R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 in general formulas (a) to (ad) are unsubstituted or substituted C1 or C2 alkyl groups.

[0154] Clause 9: R1, R2, R3, R4, R5, R6, R7, and R8 in general formulas (I) to (VII) or R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 in general formulas (a) to (ad) are organometallic compounds as described in any one of Clauses 2 to 8, which are either identical or different from each other.

[0155] Clause 10: The organometallic compound according to any one of Clauses 1 to 9, wherein the organometallic compound has a melting point of at least 100°C, particularly in the range of 300°C to 600°C.

[0156] Clause 11: The organometallic compound according to any one of Clauses 1 to 10, wherein the organometallic compound has a dissociation energy of at least 30 kcal / mol.

[0157] Clause 12: The organometallic compounds are methylbismutanone, ethylbismutanone, propylbismutanone, butylbismutanone, methylbismutanthion, ethylbismutanthion, propylbismutanthion, butylbismutanthion, Bi-methylbismutanimine, Bi-ethylbismutanimine, Bi-propylbismutanimine, Bi-butylbismutanimine, trimethyl-λ 5 -Bismutanone, triethyl-λ 5 -Bismutanone, tripropyl-λ 5 -Bismutanone, tributyl-λ 5 -Bismutanone, trimethyl-λ 5-Bismutanthion, triethyl-λ 5 -Bismutanthion, tripropyl-λ 5 -Bismutanthion, tributyl-λ 5 -Bismutanthion, Bi,Bi,Bi-trimethyl-λ 5 -Bismutanimine, Bi,Bi,Bi-triethyl-λ 5 -Bismutaneimine, Bi,Bi,Bi-tripropyl-λ 5 -Bismutaneimine, Bi,Bi,Bi-tributyl-λ 5 -Bismutanimine, propane-2-ylbismutanone, tert-butylbismutanone, propane-2-ylbismutanthion, tert-butylbismutanthion, Bi-propane-2-ylbismutanimine, Bi-tert-butylbismutanimine, tri(propane-2-yl)-λ 5 -Bismutanone, tri(tert-butyl)-λ 5 -bismutanone, tri(propane-2-yl)-λ 5 -Bismutanthion, tri(tert-butyl)-λ 5 -Bismutanthion, Bi,Bi,Bi-tri(propane-2-yl)-λ 5 -Bismutaneumimine, Bi,Bi,Bi-tri(tert-butyl)-λ 5 - Bismutanimine, cyclopropylbismutanone, cyclobutylbismutanone, cyclopropylbismutanthion, cyclobutylbismutanthion, Bi-cyclopropylbismutanimine, Bi-cyclobutylbismutanimine, tricyclopropyl-λ 5 -Bismutanone, tricyclobutyl-λ 5 -Bismutanone, tricyclopropyl-λ 5 -Bismutanthion, tricyclobutyl-λ 5 -Bismutanthion, Bi,Bi,Bi-tricyclopropyl-λ 5 -Bismutaneimine, Bi,Bi,Bi-tricyclobutyl-λ 5-Bismutanimine, Dimethylbismutanyloxy(dimethyl)bismutan, Bis(dimethylbismutanyloxy)(methyl)bismutan, Dimethylbismutanylsulfanyl(dimethyl)bismutan, Bis(dimethylbismutanylsulfanyl)(methyl)bismutan, Bis(dimethylbismutanyl)amine, Dimethylbismutanylamino(methyl)bismutanyl(dimethylbismutanyl)amine, Diethylbismutanyloxy(diethyl)bismutan, Bis(diethylbismutanyloxy)(ethyl)bismutan, Diethylbismutanylsulfanyl(diethyl)bismutan, Bis(diethylbismutanylsulfanyl)(ethyl)bismutan, Bis(diethylbismutanyl)amine, Diethylbismutanylamino(ethyl)bismutanyl(diethylbismutanyl)amine, Dipro Pyrbismutanyloxy(dipropyl)bismutan, bis(dipropylbismutanyloxy)(propyl)bismutan, dipropylbismutanylsulfanyl(dipropyl)bismutan, bis(dipropylbismutanylsulfanyl)(propyl)bismutan, bis(dipropylbismutanyl)amine, dipropylbismutanylamino(propyl)bismutanyl(dipropylbismutanyl)amine, dibutylbismutanyloxy(dibutyl)bismutan, bis(dibutylbismutanyloxy)(butyl)bismutan, dibutylbismutanylsulfanyl(dibutyl)bismutan, bis(dibutylbismutanylsulfanyl)(butyl)bismutan, bis(dibutylbismutanylamine), dibutylbismutanylamino(butyl)bismutanyl(dibutylbismutanyl, tetramethyl-λ 5 -bismutanyloxy(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyloxy)(trimethyl)-λ 5 -Bismutane, tetramethyl-λ 5 -bismutanylsulfanil(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanylsulfanyl)(trimethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyl)amine, tetramethyl-λ5 -bismutanylamino(trimethyl)-λ 5 -bismutanyl)(tetramethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanyloxy(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanyloxy)(triethyl)-λ 5 -Bismutane, tetraethyl-λ 5 -bismutanylsulfanyl(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanylsulfanyl)(triethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanylamino(triethyl)-λ 5 -bismutanyl)(tetraethyl-λ) 5 -Bismutanyl)amine, tetrapropyl-λ 5 -bismutanyloxy(tetrapropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -bismutanyloxy)(tripropyl)-λ 5 -Bismutane, tetrapropyl-λ 5 -Bismutanylsulfanil(tetrapropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -bismutanylsulfanil)(tripropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -Bismutanyl)amine, tetrapropyl-λ 5 -bismutanylamino(tripropyl)-λ 5 -bismutanil)(tetrapropyl-λ 5 -bismutanyl)amine, tetrabutyl-λ 5 -bismutanyloxy(tetrabutyl)-λ 5 -Bismutane, bis(tetrabutyl-λ) 5 -bismutanyloxy)(tributyl)-λ 5-Bismutane, tetrabutyl-λ 5 -bismutanylsulfanil(tetrabutyl)-λ 5 -Bismutane, bis(tetrabutyl-λ) 5 -bismutanylsulfanyl)(tributyl)-λ 5 -Bismutane, bis(tetrabutyl-λ) 5 -bismutanyl)amine, tetrabutyl-λ 5 -bismutanylamino(tributyl)-λ 5 -bismutanil)(tetrabutyl-λ) 5 -bismutanyl)amine, dicyclopropylbismutanyloxy(dicyclopropyl)bismutan, bis(dicyclopropylbismutanyloxy)(cyclopropyl)bismutan, dicyclopropylbismutanylsulfanyl(dicyclopropyl)bismutan, bis(dicyclopropylbismutanylsulfanyl)(cyclopropyl)bismutan, bis(dicyclopropylbismutanyl)amine, dicyclopropylbismutanylamino(cyclopropyl)bismutanyl(dicyclopropylbismutanyl)amine, dicyclobutylbismutanyloxy(dicyclobutyl)bismutan, bis(dicyclobutylbismutanyloxy)(cyclobutyl)bismutan, dicyclobutylbismutanylsulfanyl(dicyclobutyl)bismutan, bis(dicyclobutylbismutanylsulfanyl)(cyclobutyl)bismutan, bis(dicyclobutylbismutanyl)amine, dicyclobutylbismutanylamino(cyclobutyl)bismutanyl(dicyclobutylbismutanyl)-amine, tetracyclopropyl-λ 5 -Bismutanyloxy(tetracyclopropyl)-λ 5 -Bismutane, bis(tetracyclopropyl-λ) 5 -bismutanyloxy)(tricyclopropyl)-λ 5 -Bismutane, tetracyclopropyl-λ 5 -Bismutanylsulfanil(tetracyclopropyl)-λ 5 -Bismutane, bis(tetracyclopropyl-λ) 5 -bismutanylsulfanil)(tricyclopropyl)-λ 5 -Bismutane, bis(tetracyclopropyl-λ)5 -bismutanyl)amine, tetracyclopropyl-λ 5 -Bismutanylamino(tricyclopropyl)-λ 5 -bismutanil)(tetracyclopropyl-λ 5 -bismutanyl)amine, tetracyclobutyl-λ 5 -bismutanyloxy(tetracyclobutyl)-λ 5 -Bismutane, bis(tetracyclobutyl-λ) 5 -bismutanyloxy)(tricyclobutyl)-λ 5 -Bismutane, tetracyclobutyl-λ 5 -bismutanylsulfanil(tetracyclobutyl)-λ 5 -Bismutane, bis(tetracyclobutyl-λ) 5 -bismutanylsulfanil)(tricyclobutyl)-λ 5 -Bismutane, bis(tetracyclobutyl-λ) 5 -bismutanyl)amine, tetracyclobutyl-λ 5 -bismutanylamino(tricyclobutyl)-λ 5 -bismutanil)(tetracyclobutyl-λ) 5 -Bismutanyl)amine, 2,4-dimethyl-1,3,2,4-dioxadibismethane, 2,4-diethyl-1,3,2,4-dioxadibismethane, 2,4-dipropyl-1,3,2,4-dioxadibismethane, 2,4-dibutyl-1,3,2,4-dioxadibismethane, 2,4-dimethyl-1,3,2,4-dithiadibismethane, 2,4-diethyl-1,3,2,4-dithiadibismethane, 2,4-dipropyl- 1,3,2,4-Dithiadibismethane, 2,4-Dibutyl-1,3,2,4-Dithiadibismethane, 2,4-Dimethyl-1,3,2,4-Dizadibismethane, 2,4-Diethyl-1,3,2,4-Dizadibismethane, 2,4-Dipropyl-1,3,2,4-Dizadibismethane, 2,4-Dibutyl-1,3,2,4-Dizadibismethane, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dioxadi-λ 5-Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,4-dicyclopropyl-1,3,2,4-dioxadibismethane, 2,4-dicyclobutyl-1,3,2,4-dioxadibismethane, 2,4-dicyclopropyl-1,3,2,4-dithiadibismethane, 2,4-dicyclobutyl Lu-1,3,2,4-Dithiadibismethane, 2,4-Dicyclopropyl-1,3,2,4-Dizadibismethane, 2,4-Dicyclobutyl-1,3,2,4-Dizadibismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Dithiadi-λ 5-Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-triethyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-tripropyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-tributyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiatribissane, 2,4,6-triethyl-1,3,5,2,4,6-trithiatribissane, 2,4,6-tripropyl-1,3, 5,2,4,6-Tritiatribissane, 2,4,6-Tributyl-1,3,5,2,4,6-Tritiatribissane, 2,4,6-Trimethyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Triethyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Tripropyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Tributyl-1,3,5,2,4,6-Triazatribissane, 2,2,2,4,4,6,6,6-Nonamethyl-1,3,5,2,4,6-Trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ 5-Bismann, 2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-triazatry-λ 5 -bissman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trioxatribissman, 2,4,6-tricyclobutyl-1,3,5,2,4,6-trioxatribissman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trithiatribissman, 2,4,6-tricyclobutyl-1,3,5,2,4,6-trithiatribissman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-triazatribissman, 2,4,6-tricyclobutyl-1,3,5,2,4,6-triazatribissman, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismann, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ 5 -bismann, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatri-λ 5 -Bisman, and 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-triazatry-λ 5 - An organometallic compound selected from the group consisting of bismann, as described in any one of clauses 1 to 11.

[0158] Clause 13: The organometallic compounds include methylbismutanone, ethylbismutanone, propylbismutanone, methylbismutanthion, ethylbismutanthion, propylbismutanthion, Bi-methylbismutanimine, Bi-ethylbismutanimine, Bi-propylbismutanimine, and trimethyl-λ 5 -Bismutanone, triethyl-λ 5 -Bismutanone, tripropyl-λ 5 -Bismutanone, trimethyl-λ 5 -Bismutanthion, triethyl-λ 5 -Bismutanthion, tripropyl-λ 5 -Bismutanthion, Bi,Bi,Bi-trimethyl-λ 5 -Bismutanimine, Bi,Bi,Bi-triethyl-λ 5 -Bismutaneimine, Bi,Bi,Bi-tripropyl-λ 5 - Bismutanimine, cyclopropylbismutanone, cyclopropylbismutanthion, Bi-cyclopropylbismutanimine, tricyclopropyl-λ 5 -Bismutanone, tricyclopropyl-λ 5 -Bismutanthion, Bi,Bi,Bi-tricyclopropyl-λ 5-Bismutanimine, Dimethylbismutanyloxy(dimethyl)bismutan, Bis(dimethylbismutanyloxy)(methyl)bismutan, Dimethylbismutanylsulfanyl(dimethyl)bismutan, Bis(dimethylbismutanylsulfanyl)(methyl)bismutan, Bis(dimethylbismutanyl)amine, Dimethylbismutanylamino(methyl)bismutanyl(dimethylbismutanyl)amine, Diethylbismutanyloxy(diethyl)bismutan, Bis(diethylbismutanyloxy)(ethyl)bismutan, Diethylbismutanylsulfanyl(diethyl)bismutan, Bis(diethylbis Mutanylsulfanyl(ethyl)bismutan, bis(diethylbismutanyl)amine, diethylbismutanylamino(ethyl)bismutanyl(diethylbismutanyl)amine, dipropylbismutanyloxy(dipropyl)bismutan, bis(dipropylbismutanyloxy)(propyl)bismutan, dipropylbismutanylsulfanyl(dipropyl)bismutan, bis(dipropylbismutanylsulfanyl)(propyl)bismutan, bis(dipropylbismutanyl)amine, dipropylbismutanylamino(propyl)bismutanyl(dipropylbismutanyl)amine, tetramethyl-λ 5 -bismutanyloxy(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyloxy)(trimethyl)-λ 5 -Bismutane, tetramethyl-λ 5 -bismutanylsulfanil(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanylsulfanyl)(trimethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyl)amine, tetramethyl-λ 5 -bismutanylamino(trimethyl)-λ 5 -bismutanyl)(tetramethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanyloxy(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ)5 -bismutanyloxy)(triethyl)-λ 5 -Bismutane, tetraethyl-λ 5 -bismutanylsulfanyl(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanylsulfanyl)(triethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanylamino(triethyl)-λ 5 -bismutanyl)(tetraethyl-λ) 5 -Bismutanyl)amine, tetrapropyl-λ 5 -bismutanyloxy(tetrapropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -bismutanyloxy)(tripropyl)-λ 5 -Bismutane, tetrapropyl-λ 5 -Bismutanylsulfanil(tetrapropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -bismutanylsulfanil)(tripropyl)-λ 5 -Bismutane, bis(tetrapropyl-λ) 5 -Bismutanyl)amine, tetrapropyl-λ 5 -bismutanylamino(tripropyl)-λ 5 -bismutanil)(tetrapropyl-λ 5 -bismutanyl)amine, dicyclopropylbismutanyloxy(dicyclopropyl)bismutan, bis(dicyclopropylbismutanyloxy)(cyclopropyl)bismutan, dicyclopropylbismutanylsulfanyl(dicyclopropyl)bismutan, bis(dicyclopropylbismutanylsulfanyl)(cyclopropyl)bismutan, bis(dicyclopropylbismutanyl)amine, dicyclopropylbismutanylamino(cyclopropyl)bismutanyl(dicyclopropylbismutanyl)amine, tetracyclopropyl-λ 5 -Bismutanyloxy(tetracyclopropyl)-λ 5-Bismutane, bis(tetracyclopropyl-λ) 5 -bismutanyloxy)(tricyclopropyl)-λ 5 -Bismutane, tetracyclopropyl-λ 5 -Bismutanylsulfanil(tetracyclopropyl)-λ 5 -Bismutane, bis(tetracyclopropyl-λ) 5 -bismutanylsulfanil)(tricyclopropyl)-λ 5 -Bismutane, bis(tetracyclopropyl-λ) 5 -bismutanyl)amine, tetracyclopropyl-λ 5 -Bismutanylamino(tricyclopropyl)-λ 5 -bismutanil)(tetracyclopropyl-λ 5 -Bismutanyl)amine, 2,4-dimethyl-1,3,2,4-dioxadibismethane, 2,4-diethyl-1,3,2,4-dioxadibismethane, 2,4-dipropyl-1,3,2,4-dioxadibismethane, 2,4-dimethyl-1,3,2,4-dithiadibismethane, 2,4-diethyl-1,3,2,4-dithiadibismethane, 2,4-dipropyl-1,3,2,4-dithiadibismethane, 2,4-dimethyl-1,3,2,4-diazadibismethane, 2,4-diethyl-1,3,2,4-diazadibismethane, 2,4-dipropyl-1,3,2,4-diazadibismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazadi-λ 5-Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,4-dicyclopropyl-1,3,2,4-dioxadibismethane, 2,4-dicyclopropyl-1,3,2,4-dithiadibismethane, 2,4-dicyclopropyl-1,3,2,4-diazabismethane, 2,2,2,4,4,4-hexacyclopropyl-1,3,2,4-dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-triethyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-tripropyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-triethyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-Tripropyl-1,3,5,2,4,6-Tritiatribissane, 2,4,6-Trimethyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Triethyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Tripropyl-1,3,5,2,4,6-Triazatribissane, 2,2,2,4,4,4,6,6,6-Nonamethyl-1,3,5,2,4,6-Trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatry-λ 5 -Bisman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trioxatribisman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trithiatribisman, 2,4,6-tricyclopropyl-1,3,5,2,4,6-triazatribisman, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ 5 -Bisman, and 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatry-λ 5 - Selected from the group consisting of bismann, preferably methylbismutanone, ethylbismutanone, methylbismutanthion, ethylbismutanthion, Bi-methylbismutanimine, Bi-ethylbismutanimine, trimethyl-λ 5 -Bismutanone, triethyl-λ 5 -Bismutanone, trimethyl-λ 5 -Bismutanthion, triethyl-λ 5 -Bismutanthion, Bi,Bi,Bi-trimethyl-λ 5 -Bismutanimine, Bi,Bi,Bi-triethyl-λ 5-Bismutanimine, Dimethylbismutanyloxy(dimethyl)bismutan, Bis(dimethylbismutanyloxy)(methyl)bismutan, Dimethylbismutanylsulfanyl(dimethyl)bismutan, Bis(dimethylbismutanylsulfanyl)(methyl)bismutan, Bis(dimethylbismutanyl)amine, Dimethylbismutanylamino(methyl)bismutanyl(dimethylbismutanyl)amine, Diethylbismutanyloxy(diethyl)bismutan, Bis(diethylbismutanyloxy)(ethyl)bismutan, Diethylbismutanylsulfanyl(diethyl)bismutan, Bis(diethylbismutanylsulfanyl)(ethyl)bis Mutan, bis(diethylbismutanyl)amine, diethylbismutanylamino(ethyl)bismutanyl(diethylbismutanyl)amine, tetramethyl-λ 5 -bismutanyloxy(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyloxy)(trimethyl)-λ 5 -Bismutane, tetramethyl-λ 5 -bismutanylsulfanil(tetramethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanylsulfanyl)(trimethyl)-λ 5 -Bismutane, bis(tetramethyl-λ) 5 -bismutanyl)amine, tetramethyl-λ 5 -bismutanylamino(trimethyl)-λ 5 -bismutanyl)(tetramethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanyloxy(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanyloxy)(triethyl)-λ 5 -Bismutane, tetraethyl-λ 5 -bismutanylsulfanyl(tetraethyl)-λ 5 -Bismutane, bis(tetraethyl-λ) 5 -bismutanylsulfanyl)(triethyl)-λ 5-Bismutane, bis(tetraethyl-λ) 5 -bismutanyl)amine, tetraethyl-λ 5 -bismutanylamino(triethyl)-λ 5 -bismutanyl)(tetraethyl-λ) 5 -bismutanyl)amine, 2,4-dimethyl-1,3,2,4-dioxadibismethane, 2,4-diethyl-1,3,2,4-dioxadibismethane, 2,4-dimethyl-1,3,2,4-dithiadibismethane, 2,4-diethyl-1,3,2,4-dithiadibismethane, 2,4-dimethyl-1,3,2,4-diazadibismethane, 2,4-diethyl-1,3,2,4-diazadibismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dioxadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dithiadi-λ 5 -Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazadi-λ 5 -Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Diazazi-λ 5 -Bismethane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-triethyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiatribissane, 2,4,6-triethyl-1,3,5,2,4,6-trithiatribissane, 2,4,6-trimethyl-1,3,5,2,4,6-triazatribissane, 2,4,6-triethyl-1,3,5,2,4,6-triazatribissane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5-Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismann, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatry-λ 5 -Bismann and 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatry-λ 5 - An organometallic compound selected from the group consisting of bismann, as described in Clause 12.

[0159] Clause 14: Use of an organometallic compound as described in any one of Clauses 1 to 13 for preparing a dry photoresist or hard mask composition for EUV lithography.

[0160] Clause 16: The dry photoresist or hard mask composition according to Clause 15, comprising the organometallic compound in an amount of 5 to 95% by weight, particularly in an amount of 10 to 90% by weight, and more specifically in an amount of 20 to 80% by weight, based on the total weight of the photoresist composition.

[0161] Clause 17: The dry photoresist or hard mask composition according to Clause 15 or 16, further comprising a solvent.

[0162] Clause 18: A dry photoresist or hard mask composition as described in any one of Clauses 15 to 17.

[0163] Clause 19: A method for forming a patterned material feature on a substrate, comprising the steps of: providing a material surface on the substrate; forming a layer of a dry photoresist or hard mask composition according to any one of Clauses 15 to 17 on the material surface; irradiating the dry photoresist or hard mask layer in a pattern with energy rays to create a pattern of irradiated / exposed areas in the dry photoresist or hard mask layer; selectively removing a portion of the dry photoresist or hard mask layer to form an exposed portion of the material surface; and etching or ion implanting the exposed portion of the material to form the patterned material feature.

[0164] Clause 20: The method according to Clause 19, wherein the step of selectively removing a portion of the dry photoresist or hard mask layer is performed using a technique selected from the group consisting of a thermal process step, a plasma ashing step, and a plasma etching process step.

Claims

1. Organometallic compounds for dry photoresists or hard masks for EUV lithography, At least one bismuth element selected from the group consisting of Bi(III) and Bi(V); At least one terminal or bridging ligand A bonded to the bismuth element, wherein the bridging ligand A is selected from the group consisting of O, S, and N-R, and the R group in N-R is selected from the group consisting of H and C1 to C6 alkyl groups; and At least one C1 to C6 alkyl ligand bonded to the bismuth element Organometallic compounds, including those containing this compound.

2. The general formula is selected from the following group: 【Chemistry 1】 Equation (I), 【Chemistry 2】 Formula (II), 【Transformation 3】 Formula (III), 【Chemistry 4】 Formula (IV), 【Transformation 5】 Formula (V), 【Transformation 6】 Formula (VI), and 【Transformation 7】 Formula (VII), Here, in the general formulas (I), (II), (III), (IV), (V), (VI), and (VII), A represents a species selected from the group consisting of O, S, and N-R; R1, R2, R3, R4, R5, R6, R7, and R8 represent alkyl ligands selected from the group consisting of optionally substituted linear or branched C1 to C6 alkyl groups, optionally substituted C3 to C6 cycloalkyl groups, and optionally substituted C3 to C6 heterocycloalkyl groups; n is an integer between 1 and 4; m is an integer from 2 to 5; and, In N-R, R represents a species selected from the group consisting of H, optionally substituted linear C1-C6 alkyl groups, optionally substituted branched C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, and optionally substituted C3-C6 heterocycloalkyl groups. The organometallic compound according to claim 1.

3. The organometallic compound according to claim 2, wherein n is an integer from 1 to 3, and m is an integer from 2 to 4.

4. The organometallic compound has a formula selected from the group consisting of formulas (a) to (ad): 【Transformation 8】 【Chemistry 9】 Here, in the general formulas (a) to (o), R1, R2, R3, R4, R1 / 1, R1 / 2, R1 / 3, RN / 1, RN / 2, and RN / 3 are independently selected from the group consisting of optionally substituted linear or branched C1 to C6 alkyl groups, optionally substituted C3 to C6 cycloalkyl groups, and optionally substituted C3 to C6 heterocycloalkyl groups; In the general formulas (p) to (ad) above, R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 are independently selected from the group consisting of optionally substituted linear or branched C1 to C6 alkyl groups, optionally substituted C3 to C6 cycloalkyl groups, and optionally substituted C3 to C6 heterocycloalkyl groups. The organometallic compound according to claim 2.

5. R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 in the above general formulas (a) to (ad) are selected from the group consisting of optionally substituted linear C1 to C5 alkyl groups, optionally substituted branched C1 to C5 alkyl groups, optionally substituted C3 to C5 cycloalkyl groups, and optionally substituted C3 to C5 heterocycloalkyl groups. The organometallic compound according to claim 4.

6. R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 in the above general formulas (a) to (ad) are selected from the group consisting of optionally substituted linear C1 to C4 alkyl groups, optionally substituted branched C1 to C4 alkyl groups, optionally substituted C3 or C4 cycloalkyl groups, and optionally substituted C3 or C4 heterocycloalkyl groups. The organometallic compound according to claim 4.

7. R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 in the above general formulas (a) to (ad) are selected from the group consisting of optionally substituted linear C1 to C3 alkyl groups, optionally substituted branched C1 to C3 alkyl groups, optionally substituted C3 cycloalkyl groups, and optionally substituted C3 heterocycloalkyl groups. The organometallic compound according to claim 4.

8. In the general formulas (a) to (ad), R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 are selected from the group consisting of optionally substituted C1 alkyl and optionally substituted C2 alkyl. The organometallic compound according to claim 4.

9. In the above general formulas (a) to (ad), R1, R2, R3, R4, R5, R6, R7, R8, R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, R3 / 2, R1 / 3, R2 / 3, R3 / 3, RN / 1, RN / 2, and RN / 3 are all the same. The organometallic compound according to claim 4.

10. The organometallic compound has a melting point of at least 100°C. The organometallic compound according to claim 1.

11. The organometallic compound has a melting point in the range of 300°C to 600°C. The organometallic compound according to claim 10.

12. The organometallic compound has a dissociation energy of at least 30 kcal / mol The organometallic compound according to claim 1.

13. The aforementioned organometallic compound is Methylbismutanone, Ethylbismutanone, Propylbismutanone, Butylbismutanone, Methylbismutanthion, Ethylbismutanthion, Propylbismutanthion, Butylbismutanthion, Bi-methylbismutanimine, Bi-ethylbismutanimine, Bi-propylbismutanimine, Bi-butylbismutanimine, trimethyl-λ ５ - Bismutanon, Triethyl-λ ５ - Bismutanon, Tripropyl-λ ５ - Bismutanon, Tributyl-λ ５ - Bismutanon, trimethyl-λ ５ - Bismutantion, Triethyl-λ ５ - Bismutantion, Tripropyl-λ ５ - Bismutantion, Tributyl-λ ５ - Bismutantion, Bi, Bi, Bi-trimethyl-λ ５ -bismuthaneimine, Bi,Bi,Bi-triethyl-λ ５ - Bisumtanimin, Bi,Bi,Bi-tripropyl-λ ５ - Bisumtanimin, Bi,Bi,Bi-tributyl-λ ５ - Bisumtanimin, Propane-2-Irbismutanone, tert-butylbismutanone, Propane-2-Irbismutanthion, tert-butylbismutanthion, Bi-propane-2-irbismutanimine, B-tert-butylbismutanimine, Tri(propane-2-yl)-λ ５ - Bismutanon, Tri(tert-butyl)-λ ５ - Bismutanon, Tri(propane-2-yl)-λ ５ - Bismutantion, Tri(tert-butyl)-λ ５ - Bismutantion, Bi, Bi, Bi-tri(propane-2-yl)-λ ５ - Bisumtanimin, Bi, Bi, Bi-tri(tert-butyl)-λ ５ - Bisumtanimin, Cyclopropyl bismutanone, Cyclobutylbismutanone, Cyclopropylbismutanthion, Cyclobutylbismutanthion, Bi-cyclopropylbismutanimine, Bi-cyclobutylbismutanimine, Tricyclopropyl-λ ５ - Bismutanon, Tricyclobutyl-λ ５ - Bismutanon, Tricyclopropyl-λ ５ - Bismutantion, Tricyclobutyl-λ ５ - Bismutantion, Bi,Bi,Bi-tricyclopropyl-λ ５ - Bisumtanimin, Bi,Bi,Bi-tricyclobutyl-λ ５ - Bisumtanimin, Dimethylbismutanyloxy(dimethyl)bismutane, Bis(dimethylbismutanyloxy)(methyl)bismutane, Dimethylbismutanylsulfanyl(dimethyl)bismutan, Bis(dimethylbismutanylsulfanyl)(methyl)bismutan, Bis(dimethylbismutanyl)amine, Dimethylbismutanylamino(methyl)bismutanyl(dimethylbismutanyl)amine, Diethylbismutanyloxy(diethyl)bismutan, Bis(diethylbismutanyloxy)(ethyl)bismutane, Diethylbismutanylsulfanyl(diethyl)bismutan, Bis(diethylbismutanylsulfanyl)(ethyl)bismutan, Bis(diethylbismutanyl)amine, Diethylbismutanylamino(ethyl)bismutanyl(diethylbismutanyl)amine, Dipropylbismutanyloxy(dipropyl)bismutan, Bis(dipropylbismutanyloxy)(propyl)bismutane, Dipropylbismutanylsulfanil(dipropyl)bismutan, Bis(dipropylbismutanylsulfanyl)(propyl)bismutane, Bis(dipropylbismutanyl)amine, Dipropylbismutanylamino(propyl)bismutanyl(dipropylbismutanyl)amine, Dibutylbismutanyloxy(dibutyl)bismutan, Bis(dibutylbismutanyloxy)(butyl)bismutane, Dibutylbismutanylsulfanil(dibutyl)bismutan, Bis(dibutylbismutanylsulfanil)(butyl)bismutane, Bis(dibutylbismutanyl)amine, Dibutylbismutanylamino(butyl)bismutanyl(dibutylbismutanyl, Tetramethyl-λ ５ -Bismutanyloxy(tetramethyl)-λ ５ - Bismutan, Bis(tetramethyl-λ) ５ -bismutanyloxy)(trimethyl)-λ ５ - Bismutan, Tetramethyl-λ ５ -Bismutanylsulfanyl(tetramethyl)-λ ５ - Bismutan, Bis(tetramethyl-λ) ５ -Bismutanylsulfanyl)(trimethyl)-λ ５ - Bismutan, Bis(tetramethyl-λ) ５ - Bismutanylamine, Tetramethyl-λ ５ -Bismutanylamino(trimethyl)-λ ５ -bismutanyl) (tetramethyl-λ ５ - Bismutanylamine, Tetraethyl-λ ５ -Bismutanyloxy(tetraethyl)-λ ５ - Bismutan, Bis(tetraethyl-λ) ５ -Bismutanyloxy)(triethyl)-λ ５ - Bismutan, Tetraethyl-λ ５ -Bismutanylsulfanyl(tetraethyl)-λ ５ - Bismutan, Bis(tetraethyl-λ) ５ -Bismutanylsulfanyl)(triethyl)-λ ５ - Bismutan, Bis(tetraethyl-λ) ５ - Bismutanylamine, Tetraethyl-λ ５ -Bismutanylamino(triethyl)-λ ５ -Bismutanyl)(tetraethyl-λ ５ - Bismutanylamine, Tetrapropyl-λ ５ -Bismutanyloxy(tetrapropyl)-λ ５ - Bismutan, Bis(tetrapropyl-λ) ５ -Bismutanyloxy)(tripropyl)-λ ５ - Bismutan, Tetrapropyl-λ ５ -Bismutanylsulfanil(tetrapropyl)-λ ５ - Bismutan, Bis(tetrapropyl-λ) ５ -Bismutanylsulfanil)(tripropyl)-λ ５ - Bismutan, Bis(tetrapropyl-λ) ５ - Bismutanylamine, Tetrapropyl-λ ５ -Bismutanylamino(tripropyl)-λ ５ -Bismutanyl)(tetrapropyl-λ ５ - Bismutanylamine, Tetrabutyl-λ ５ -Bismutanyloxy(tetrabutyl)-λ ５ - Bismutan, Bis(tetrabutyl-λ) ５ -Bismutanyloxy)(tributyl)-λ ５ - Bismutan, Tetrabutyl-λ ５ -Bismutanylsulfanil(tetrabutyl)-λ ５ - Bismutan, Bis(tetrabutyl-λ) ５ -Bismutanylsulfanyl)(tributyl)-λ ５ - Bismutan, Bis(tetrabutyl-λ) ５ - Bismutanylamine, Tetrabutyl-λ ５ -Bismutanylamino(tributyl)-λ ５ -Bismutanyl)(tetrabutyl-λ ５ - Bismutanylamine, Dicyclopropylbismutanyloxy(dicyclopropyl)bismutan, Bis(dicyclopropylbismutanyloxy)(cyclopropyl)bismutane, Dicyclopropylbismutanylsulfanil(dicyclopropyl)bismutan, Bis(dicyclopropylbismutanylsulfanyl)(cyclopropyl)bismutane, Bis(dicyclopropylbismutanyl)amine, Dicyclopropylbismutanylamino(cyclopropyl)bismutanyl(dicyclopropylbismutanyl)amine, Dicyclobutylbismutanyloxy(dicyclobutyl)bismutane, Bis(dicyclobutylbismutanyloxy)(cyclobutyl)bismutane, Dicyclobutylbismutanylsulfanil (dicyclobutyl)bismutan, Bis(dicyclobutylbismutanylsulfanil)(cyclobutyl)bismutane, Bis(dicyclobutylbismutanyl)amine, Dicyclobutylbismutanylamino(cyclobutyl)bismutanyl(dicyclobutylbismutanyl)amine, Tetracyclopropyl-λ ５ -Bismutanyloxy(tetracyclopropyl)-λ ５ - Bismutan, Bis(tetracyclopropyl-λ) ５ -Bismutanyloxy)(tricyclopropyl)-λ ５ - Bismutan, Tetracyclopropyl-λ ５ - Bismutanylsulfanil(tetracyclopropyl)-λ ５ - Bismutan, Bis(tetracyclopropyl-λ) ５ -Bismutanylsulfanil)(tricyclopropyl)-λ ５ - Bismutan, Bis(tetracyclopropyl-λ) ５ - Bismutanylamine, Tetracyclopropyl-λ ５ -Bismutanylamino(tricyclopropyl)-λ ５ -Bismutanyl)(tetracyclopropyl-λ ５ - Bismutanylamine, Tetracyclobutyl-λ ５ -Bismutanyloxy(tetracyclobutyl)-λ ５ - Bismutan, Bis(tetracyclobutyl-λ) ５ -Bismutanyloxy)(tricyclobutyl)-λ ５ - Bismutan, Tetracyclobutyl-λ ５ -bismuthanylthio(tetracyclobutyl)-λ ５ -bismuthane, Bis(tetracyclobutyl-λ) ５ -Bismutanylsulfanil)(tricyclobutyl)-λ ５ - Bismutan, Bis(tetracyclobutyl-λ) ５ - Bismutanylamine, Tetracyclobutyl-λ ５ -Bismutanylamino(tricyclobutyl)-λ ５ -Bismutanyl)(tetracyclobutyl-λ ５ - Bismutanylamine, 2,4-dimethyl-1,3,2,4-dioxadibismethane, 2,4-diethyl-1,3,2,4-dioxadibismethane, 2,4-dipropyl-1,3,2,4-dioxadibismethane, 2,4-Dibutyl-1,3,2,4-Dioxadibismethane, 2,4-dimethyl-1,3,2,4-dithiadibismethane, 2,4-diethyl-1,3,2,4-dithiadibismethane, 2,4-dipropyl-1,3,2,4-dithiadibismethane, 2,4-Dibutyl-1,3,2,4-Dithiadibismethane, 2,4-dimethyl-1,3,2,4-diazadibismethane, 2,4-diethyl-1,3,2,4-diazadibismethane, 2,4-dipropyl-1,3,2,4-diazadibismethane, 2,4-Dibutyl-1,3,2,4-Diazazibismethane, 2,2,2,4,4,4 - Hexamethyl - 1,3,2,4 - dioxadi - λ ５ - bis(methane), 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexabutyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,4-dicyclopropyl-1,3,2,4-dioxadibismethane, 2,4-Dicyclobutyl-1,3,2,4-Dioxadibismethane, 2,4-dicyclopropyl-1,3,2,4-dithiadibismethane, 2,4-Dicyclobutyl-1,3,2,4-Dithiadibismethane 2,4-dicyclopropyl-1,3,2,4-diazabismethane, 2,4-Dicyclobutyl-1,3,2,4-Diazazibismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexacyclobutyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-triethyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-tripropyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-tributyl-1,3,5,2,4,6-trioxatribissane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-triethyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-tripropyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-tributyl-1,3,5,2,4,6-trithiatribissane, 2,4,6-trimethyl-1,3,5,2,4,6-triazatribissane, 2,4,6-triethyl-1,3,5,2,4,6-triazatribismane, 2,4,6-tripropyl-1,3,5,2,4,6-triazatribissane, 2,4,6-tributyl-1,3,5,2,4,6-triazaltribissane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatry-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatry-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonabutyl-1,3,5,2,4,6-triazatry-λ ５ - Bisman, 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Trioxatribissane, 2,4,6-Tricyclobutyl-1,3,5,2,4,6-Trioxatribissane, 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Tritiatribismane 2,4,6-Tricyclobutyl-1,3,5,2,4,6-Tritiatribissane, 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Triazatribissane, 2,4,6-Tricyclobutyl-1,3,5,2,4,6-Triazatribissane, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatri-λ ５ - Bisman, and 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-triazatry-λ ５ - Bisman An organometallic compound according to claim 1, selected from the group consisting of the following.

14. The aforementioned organometallic compound is Methylbismutanone, Ethylbismutanone, Propylbismutanone, Methylbismutanthion, Ethylbismutanthion, Propylbismutanthion, Bi-methylbismutanimine, Bi-ethylbismutanimine, Bi-propylbismutanimine, trimethyl-λ ５ - Bismutanon, Triethyl-λ ５ - Bismutanon, Tripropyl-λ ５ - Bismutanon, trimethyl-λ ５ - Bismutantion, Triethyl-λ ５ - Bismutantion, Tripropyl-λ ５ - Bismutantion, Bi,Bi,Bi-trimethyl-λ ５ - Bisumtanimin, Bi,Bi,Bi-triethyl-λ ５ - Bisumtanimin, Bi,Bi,Bi-tripropyl-λ ５ - Bisumtanimin, Cyclopropyl bismutanone, Cyclopropylbismutanthion, Bi-cyclopropylbismutanimine, Tricyclopropyl-λ ５ - Bismutanon, Tricyclopropyl-λ ５ - Bismutantion, Bi,Bi,Bi-tricyclopropyl-λ ５ - Bisumtanimin, Dimethylbismutanyloxy(dimethyl)bismutane, Bis(dimethylbismutanyloxy)(methyl)bismutane, Dimethylbismutanylsulfanyl(dimethyl)bismutan, Bis(dimethylbismutanylsulfanyl)(methyl)bismutan, Bis(dimethylbismutanyl)amine, Dimethylbismutanylamino(methyl)bismutanyl(dimethylbismutanyl)amine, Diethylbismutanyloxy(diethyl)bismutan, Bis(diethylbismutanyloxy)(ethyl)bismutane, Diethylbismutanylsulfanyl(diethyl)bismutan, Bis(diethylbismutanylsulfanyl)(ethyl)bismutan, Bis(diethylbismutanyl)amine, Diethylbismutanylamino(ethyl)bismutanyl(diethylbismutanyl)amine, Dipropylbismutanyloxy(dipropyl)bismutan, Bis(dipropylbismutanyloxy)(propyl)bismutane, Dipropylbismutanylsulfanil(dipropyl)bismutan, Bis(dipropylbismutanylsulfanyl)(propyl)bismutane, Bis(dipropylbismutanyl)amine, Dipropylbismutanylamino(propyl)bismutanyl(dipropylbismutanyl)amine, Tetramethyl-λ ５ -Bismutanyloxy(tetramethyl)-λ ５ - Bismutan, Bis(tetramethyl-λ) ５ -bismutanyloxy)(trimethyl)-λ ５ - Bismutan, Tetramethyl-λ ５ -Bismutanylsulfanyl(tetramethyl)-λ ５ - Bismutan, Bis(tetramethyl-λ) ５ -Bismutanylsulfanyl)(trimethyl)-λ ５ - Bismutan, Bis(tetramethyl-λ) ５ - Bismutanylamine, Tetramethyl-λ ５ -Bismutanylamino(trimethyl)-λ ５ -bismutanyl) (tetramethyl-λ ５ - Bismutanylamine, Tetraethyl-λ ５ -Bismutanyloxy(tetraethyl)-λ ５ - Bismutan, Bis(tetraethyl-λ) ５ -Bismutanyloxy)(triethyl)-λ ５ - Bismutan, Tetraethyl-λ ５ -Bismutanylsulfanyl(tetraethyl)-λ ５ - Bismutan, Bis(tetraethyl-λ) ５ -Bismutanylsulfanyl)(triethyl)-λ ５ - Bismutan, Bis(tetraethyl-λ) ５ - Bismutanylamine, Tetraethyl-λ ５ -Bismutanylamino(triethyl)-λ ５ -Bismutanyl)(tetraethyl-λ ５ - Bismutanylamine, Tetrapropyl-λ ５ -Bismutanyloxy(tetrapropyl)-λ ５ - Bismutan, Bis(tetrapropyl-λ) ５ -Bismutanyloxy)(tripropyl)-λ ５ - Bismutan, Tetrapropyl-λ ５ -Bismutanylsulfanil(tetrapropyl)-λ ５ - Bismutan, Bis(tetrapropyl-λ) ５ -Bismutanylsulfanil)(tripropyl)-λ ５ - Bismutan, Bis(tetrapropyl-λ) ５ - Bismutanylamine, Tetrapropyl-λ ５ -Bismutanylamino(tripropyl)-λ ５ -Bismutanyl)(tetrapropyl-λ ５ - Bismutanylamine, Dicyclopropylbismutanyloxy(dicyclopropyl)bismutan, Bis(dicyclopropylbismutanyloxy)(cyclopropyl)bismutane, Dicyclopropylbismutanylsulfanil(dicyclopropyl)bismutan, Bis(dicyclopropylbismutanylsulfanyl)(cyclopropyl)bismutane, Bis(dicyclopropylbismutanyl)amine, Dicyclopropylbismutanylamino(cyclopropyl)bismutanyl(dicyclopropylbismutanyl)amine, Tetracyclopropyl-λ ５ -Bismutanyloxy(tetracyclopropyl)-λ ５ - Bismutan, Bis(tetracyclopropyl-λ) ５ -Bismutanyloxy)(tricyclopropyl)-λ ５ - Bismutan, Tetracyclopropyl-λ ５ - Bismutanylsulfanil(tetracyclopropyl)-λ ５ - Bismutan, Bis(tetracyclopropyl-λ) ５ -Bismutanylsulfanil)(tricyclopropyl)-λ ５ - Bismutan, Bis(tetracyclopropyl-λ) ５ - Bismutanylamine, Tetracyclopropyl-λ ５ -Bismutanylamino(tricyclopropyl)-λ ５ -Bismutanyl)(tetracyclopropyl-λ ５ - Bismutanylamine, 2,4-dimethyl-1,3,2,4-dioxadibismethane, 2,4-diethyl-1,3,2,4-dioxadibismethane, 2,4-dipropyl-1,3,2,4-dioxadibismethane, 2,4-dimethyl-1,3,2,4-dithiadibismethane, 2,4-diethyl-1,3,2,4-dithiadibismethane, 2,4-dipropyl-1,3,2,4-dithiadibismethane, 2,4-dimethyl-1,3,2,4-diazadibismethane, 2,4-diethyl-1,3,2,4-diazadibismethane, 2,4-dipropyl-1,3,2,4-diazadibismethane, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexapropyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,4-dicyclopropyl-1,3,2,4-dioxadibismethane, 2,4-dicyclopropyl-1,3,2,4-dithiadibismethane, 2,4-dicyclopropyl-1,3,2,4-diazabismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexacyclopropyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-triethyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-tripropyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-triethyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-tripropyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-trimethyl-1,3,5,2,4,6-triazatribissane, 2,4,6-triethyl-1,3,5,2,4,6-triazatribismane, 2,4,6-tripropyl-1,3,5,2,4,6-triazatribissane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatry-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatry-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatri-λ ５ - Bisman, 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Trioxatribissane, 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Tritiatribismane 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Triazatribissane, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, and 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatri-λ ５ - Bisman An organometallic compound according to claim 13, selected from the group consisting of the following.

15. The aforementioned organometallic compound is Methylbismutanone, Ethylbismutanone, Methylbismutanthion, Ethylbismutanthion, Bi-methylbismutanimine, Bi-ethylbismutanimine, trimethyl-λ ５ - Bismutanon, Triethyl-λ ５ - Bismutanon, trimethyl-λ ５ - Bismutantion, Triethyl-λ ５ - Bismutantion, Bi,Bi,Bi-trimethyl-λ ５ - Bisumtanimin, Bi,Bi,Bi-triethyl-λ ５ - Bisumtanimin, Dimethylbismutanyloxy(dimethyl)bismutane, Bis(dimethylbismutanyloxy)(methyl)bismutane, Dimethylbismutanylsulfanyl(dimethyl)bismutan, Bis(dimethylbismutanylsulfanyl)(methyl)bismutan, Bis(dimethylbismutanyl)amine, Dimethylbismutanylamino(methyl)bismutanyl(dimethylbismutanyl)amine, Diethylbismutanyloxy(diethyl)bismutan, Bis(diethylbismutanyloxy)(ethyl)bismutane, Diethylbismutanylsulfanyl(diethyl)bismutan, Bis(diethylbismutanylsulfanyl)(ethyl)bismutan, Bis(diethylbismutanyl)amine, Diethylbismutanylamino(ethyl)bismutanyl(diethylbismutanyl)amine, Tetramethyl-λ ５ -Bismutanyloxy(tetramethyl)-λ ５ - Bismutan, Bis(tetramethyl-λ) ５ -bismutanyloxy)(trimethyl)-λ ５ - Bismutan, Tetramethyl-λ ５ -Bismutanylsulfanyl(tetramethyl)-λ ５ - Bismutan, Bis(tetramethyl-λ) ５ -Bismutanylsulfanyl)(trimethyl)-λ ５ - Bismutan, Bis(tetramethyl-λ) ５ - Bismutanylamine, Tetramethyl-λ ５ -Bismutanylamino(trimethyl)-λ ５ -bismutanyl) (tetramethyl-λ ５ - Bismutanylamine, Tetraethyl-λ ５ -Bismutanyloxy(tetraethyl)-λ ５ - Bismutan, Bis(tetraethyl-λ) ５ -Bismutanyloxy)(triethyl)-λ ５ - Bismutan, Tetraethyl-λ ５ -Bismutanylsulfanyl(tetraethyl)-λ ５ - Bismutan, Bis(tetraethyl-λ) ５ -Bismutanylsulfanyl)(triethyl)-λ ５ - Bismutan, Bis(tetraethyl-λ) ５ - Bismutanylamine, Tetraethyl-λ ５ -Bismutanylamino(triethyl)-λ ５ -Bismutanyl)(tetraethyl-λ ５ - Bismutanylamine, 2,4-dimethyl-1,3,2,4-dioxadibismethane, 2,4-diethyl-1,3,2,4-dioxadibismethane, 2,4-dimethyl-1,3,2,4-dithiadibismethane, 2,4-diethyl-1,3,2,4-dithiadibismethane, 2,4-dimethyl-1,3,2,4-diazadibismethane, 2,4-diethyl-1,3,2,4-diazadibismethane, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dioxadi-λ ５ - Bismethane, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Dithiadi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,2,2,4,4,4-Hexaethyl-1,3,2,4-Diazazi-λ ５ - Bismethane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-triethyl-1,3,5,2,4,6-trioxatribismane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-triethyl-1,3,5,2,4,6-trithiatribismane, 2,4,6-trimethyl-1,3,5,2,4,6-triazatribissane, 2,4,6-triethyl-1,3,5,2,4,6-triazatribismane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ ５ - Bisman, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatry-λ ５ - Bisman, and 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatry-λ ５ - Bisman An organometallic compound according to claim 14, selected from the group consisting of the following.

16. A method for preparing a dry photoresist or hard mask composition for EUV lithography, The process includes the step of providing an organometallic compound, wherein the organometallic compound is: At least one bismuth element selected from the group consisting of Bi(III) and Bi(V); At least one terminal or bridging ligand A bonded to the bismuth element, wherein the bridging ligand A is selected from the group consisting of O, S, and N-R, and the R group in N-R is selected from the group consisting of H and C1 to C6 alkyl groups; and The bismuth element has at least one C1 to C6 alkyl ligand bonded to it. method.

17. A dry photoresist or hard mask composition for EUV lithography, The organometallic compound comprises: At least one bismuth element selected from the group consisting of Bi(III) and Bi(V); At least one terminal or bridging ligand A bonded to the bismuth element, wherein the bridging ligand A is selected from the group consisting of O, S, and N-R, and the R group in N-R is selected from the group consisting of H and C1 to C6 alkyl groups; and The bismuth element has at least one C1 to C6 alkyl ligand bonded to it, Dry photoresist or hard mask composition.

18. The dry photoresist or hard mask composition according to claim 17, wherein the organometallic compound is in an amount selected from the group consisting of 5 to 95% by weight, 10 to 90% by weight, and 20 to 80% by weight, based on the total weight of the composition.

19. The dry photoresist or hard mask composition according to claim 17, further comprising a solvent.

20. The organometallic compound has a general formula selected from the group consisting of the following: 【Chemistry 10】 Equation (I), 【Chemistry 11】 Formula (II), 【Chemistry 12】 Formula (III), 【Chemistry 13】 Formula (IV), 【Chemistry 14】 Formula (V), 【Chemistry 15】 Formula (VI), and 【Chemistry 16】 Formula (VII), Here, in the general formulas (I), (II), (III), (IV), (V), (VI), and (VII), A represents a species selected from the group consisting of O, S, and N-R; R1, R2, R3, R4, R5, R6, R7, and R8 represent alkyl ligands selected from the group consisting of optionally substituted linear C1-C6 alkyl groups, optionally substituted branched C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, and optionally substituted C3-C6 heterocycloalkyl groups; n is an integer between 1 and 4; m is an integer from 2 to 5; and, In N-R, R represents a species selected from the group consisting of H, optionally substituted linear C1-C6 alkyl groups, optionally substituted branched C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, and optionally substituted C3-C6 heterocycloalkyl groups. The dry photoresist or hard mask composition according to claim 17.

21. A dry photoresist or hard mask for EUV lithography, A dry photoresist or hard mask composition comprising an organometallic compound, wherein the organometallic compound is: At least one bismuth element selected from the group consisting of Bi(III) and Bi(V); At least one terminal or bridging ligand A bonded to the bismuth element, wherein the bridging ligand A is selected from the group consisting of O, S, and N-R, and the R group in N-R is selected from the group consisting of H and C1 to C6 alkyl groups; and The bismuth element has at least one C1 to C6 alkyl ligand bonded to it. Dry photoresist or hard mask.

22. The organometallic compound has a general formula selected from the group consisting of the following: 【Chemistry 17】 Equation (I), [Chemistry 18] Formula (II), 【Chemistry 19】 Formula (III), 【Chemistry 20】 Formula (IV), 【Chemistry 21】 Formula (V), 【Chemistry 22】 Formula (VI), and 【Chemistry 23】 Formula (VII), Here, in the general formulas (I), (II), (III), (IV), (V), (VI), and (VII), A represents a species selected from the group consisting of O, S, and N-R; R1, R2, R3, R4, R5, R6, R7, and R8 represent alkyl ligands selected from the group consisting of optionally substituted linear C1-C6 alkyl groups, optionally substituted branched C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, and optionally substituted C3-C6 heterocycloalkyl groups; n is an integer between 1 and 4; m is an integer from 2 to 5; and, In N-R, R represents a species selected from the group consisting of H, optionally substituted linear C1-C6 alkyl groups, optionally substituted branched C1-C6 alkyl groups, optionally substituted C3-C6 cycloalkyl groups, and optionally substituted C3-C6 heterocycloalkyl groups. The dry photoresist or hard mask according to claim 21.

23. A method for forming patterned material features on a substrate, A step of providing a material surface on the substrate; The step of forming a layer of a dry photoresist or hard mask composition having an organometallic compound on the surface of the material, wherein the organometallic compound is: At least one bismuth element selected from the group consisting of Bi(III) and Bi(V); At least one terminal or bridging ligand A bonded to the bismuth element, wherein the bridging ligand A is selected from the group consisting of O, S, and N-R, and the R group in N-R is selected from the group consisting of H and C1 to C6 alkyl groups; and Having at least one C1 to C6 alkyl ligand bonded to the bismuth element; A step of irradiating the layer in a patterned manner with energy rays to form a pattern of irradiated / exposed regions in the layer; A step of selectively removing a portion of the layer to form an exposed portion of the material surface; and The step of etching or ion implanting the exposed portion of the material surface to form the patterned material feature. Methods that include...

24. The method according to claim 23, wherein the step of selectively removing a portion of the layer is performed using a technique selected from the group consisting of a thermal process step, a plasma ashing step, and a plasma etching process step.

25. The method according to claim 23, wherein the energy rays include extreme ultraviolet (EUV) irradiation.

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