Dry photoresist or hard mask for EUV lithography

Abstract

The present application discloses an organometallic compound for extreme ultraviolet (EUV) lithography, a composition, and a dry photoresist or hard mask. The organometallic compound contains at least one bismuth element selected from the group consisting of Bi (III) and Bi (V). The organometallic compound also comprises at least one C1 to C6 alkyl ligand bonded to the bismuth element and at least one terminal or bridging ligand A (O, S or N-R, where the R group in N-R is H or C1 to C6 alkyl). Methods of making the dry photoresist or hardmask compositions and methods of using the compositions to form patterned material features on a substrate are also disclosed.

Description

Background Technology

[0001] The disclosure of this invention relates to photoresist materials for extreme ultraviolet (EUV) lithography and, more specifically, to organometallic compounds for dry photoresists or hard masks.

[0002] Photoresist is a photosensitive material that blocks the action of certain chemicals in desired areas after photoimaging and subsequent processing. Examples of photoresists used in deep ultraviolet (DUV) and EUV lithography for 7-nm and 5-nm technology nodes include polymer-based chemically amplified photoresists and metal-organic photoresists. Metal-organic photoresists include organotin compounds, where EUV exposure causes the dissociation of the organotin Sn-C bonds, resulting in changes in solubility or the generation of volatile products. Hard masks are used as etching masks in semiconductor processing as an alternative to polymers or other organic "soft" resist materials.

[0003] However, currently available chemically amplified photoresists for EUV lithography can be limited in resolution and pattern quality due to the stochastic effects of acids and relatively long diffusion lengths. 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 bromide (IV). However, these can present challenging processing windows. For example, tetramethyltin has a low boiling point and evaporates rapidly from the wafer surface when evacuated at room temperature. Additionally, the sublimation of tin bromide (IV) can be difficult to manage due to its near-room-temperature vapor pressure of 100 Pa.

[0004] Currently available chemically amplified photoresists have drawbacks in terms of toxicity and chemical waste due to their use of photoacid generators. Existing dry photoresists or hard mask platforms suffer from similar drawbacks due to the use of organotin compounds and / or from bromine or chlorine reaction products. Furthermore, mitigating the process integration risks associated with these platforms is challenging. Summary of the Invention

[0005] Embodiments of this invention relate to organometallic compounds for use in dry photoresists or hard masks for EUV lithography. The organometallic compound contains at least one bismuth element selected from Bi(III) and Bi(V). The organometallic compound also contains at least one terminal or bridging ligand A bonded to the bismuth element. Ligand A is O, S, or NR, and the R group in NR is H or a C1 to C6 alkyl group. The organometallic compound contains at least one C1 to C6 alkyl ligand bonded to the bismuth element. In some embodiments, the organometallic compound may be represented by general formulas (I), (II), (III), (IV), (V), (VI), and (VII):

[0006]

[0007] General formula (I),

[0008]

[0009] General formula (II),

[0010]

[0011] General formula (III),

[0012]

[0013] General formula (IV),

[0014]

[0015] General formula (V),

[0016]

[0017] General formula (VI), and

[0018]

[0019] General formula (VII),

[0020] In formulas (I), (II), (III), (IV), (V), (VI), and (VII), A can represent O, S, or NR; each of R1, R2, R3, R4, R5, R6, R7, and R8 can represent an optionally substituted linear or branched C1 to C6 alkyl, an optionally substituted C3 to C6 cycloalkyl, or an optionally substituted C3 to C6 heterocyclic alkyl; n can be an integer from 1 to 4; m can be an integer from 2 to 5; and R in NR can represent H, an optionally substituted linear or branched C1 to C6 alkyl, an optionally substituted C3 to C6 cycloalkyl, or an optionally substituted C3 to C6 heterocyclic alkyl. Organometallic compounds enable more sensitive and environmentally friendly photoresists or hard masks compared to existing materials.

[0021] Further embodiments relate to a method for preparing a dry photoresist or hard mask composition for EUV lithography, the method comprising providing an organometallic compound. Additional embodiments relate to a dry photoresist or hard mask composition comprising the organometallic compound, and a dry photoresist or hard mask for EUV lithography comprising the composition.

[0022] Another embodiment relates to a method for forming patterned material features. The method includes providing a material surface on a substrate and forming a layer of dry photoresist or hard mask composition over the material surface. The method also includes patterning the dry photoresist or hard mask layer with energy rays to form a pattern of radiation exposure regions within the dry photoresist or hard mask layer. A portion of the dry photoresist or hard mask layer is then selectively removed to form exposed portions of the material surface. Patterned material features are formed by etching or ion implantation of the exposed portions of the material. Brief description of the attached diagram

[0023] The accompanying drawings included in this application are incorporated in and form part of the specification. They illustrate embodiments of the disclosure and, together with the specification, serve to explain the principles of the disclosure. The drawings are merely illustrative representations of certain embodiments and do not limit the scope of the disclosure.

[0024] Figure 1 This is a diagram of the photon absorption mode cross-sections for all natural elements at 92 eV.

[0025] Figure 2 These are, according to some implementation schemes, complete sets of chemical structure diagrams (a) to (j) of organometallic compounds used for dry photoresist or hard masks in EUV lithography.

[0026] Figure 3A According to some embodiments, there are first sets of chemical structure diagrams (a) to (o) of single, linear or cyclic organometallic compounds for use in dry photoresist or hard masks for EUV lithography, wherein Bi is in the oxidation state (III).

[0027] Figure 3B According to some embodiments, there is a second set of chemical structure diagrams (p) to (ad) representing a single, linear or cyclic organometallic compound used for dry photoresist or hard mask for EUV lithography, wherein Bi is in the oxidation state (V).

[0028] Figure 4A-5B This is a set of chemical structure diagrams of individual organometallic compounds, represented by general formulas (I) and (IV), used for dry photoresist or hard masks for EUV lithography, according to some implementation schemes.

[0029] Figures 6A-7B This is a set of chemical structure diagrams illustrating linear organometallic compounds for EUV lithography dry photoresists or hard masks, represented by general formulas (II), (V), and (VI), according to some implementation schemes.

[0030] Figures 8A-9BThis is a set of chemical structure diagrams illustrating, according to some implementation schemes, the cyclic organometallic compounds represented by general formulas (III) and (VII) used for EUV lithography dry photoresist or hard masks.

[0031] Figure 10A-11B This is a set of chemical structure diagrams illustrating, according to some implementation schemes, the cyclic organometallic compounds represented by general formulas (III) and (VII) used for EUV lithography dry photoresist or hard masks.

[0032] Figure 12 This is a flowchart illustrating a method for forming patterned material features on a substrate using a dry photoresist or hard mask composition, according to some embodiments.

[0033] While the invention is readily adaptable to various modifications and alternatives, the specific details of which have been illustrated by way of example in the accompanying drawings and will be described in detail, it should be understood that the invention is not limited to the specific embodiments described. Rather, the invention is intended to cover all modifications, equivalents, and alternatives that fall within the spirit and scope of the invention. Invention Details

[0035] The disclosure of this invention relates to photoresist materials for extreme ultraviolet (EUV) lithography and, more specifically, to organometallic compounds for use in dry photoresists or hard masks.

[0036] The description of various embodiments of the disclosed invention is presented for illustrative purposes but is not intended to be exhaustive or limited to the disclosed embodiments. Many modifications and variations will be apparent to those skilled in the art without departing from the scope and spirit of the described embodiments. The terminology used in this application is chosen to best explain the principles of the embodiments, practical application, or technical improvements relative to technologies found in the market, or to enable those skilled in the art to understand the embodiments disclosed in this application.

[0037] Unless otherwise stated, the following terms used in this application, including the specification and claims, have the definitions given below. It should be noted that, as used in the specification and appended claims, the singular forms “a,” “an,” and “the” include plural references unless otherwise clearly indicated. The term “comprising” as used in this application means that the mentioned component is essential, but other components may be added and still contained in the composition. The term “composed of,” as used in this application, as in the disclosure of the invention, generally means that the total amount of the components in the composition adds up to 100% and implies a closed subject matter that may include explicitly listed limitations. Whenever “comprising” is mentioned, it is intended to cover both meanings as alternatives, namely, that the meaning can be “comprising” or “composed of,” unless otherwise clearly indicated.

[0038] The term "compound" or "compound of the disclosure of this invention" refers to all compounds covered by the general structural formulas (I) to (VII) disclosed in this application or by the general structural formulas (a) to (r) disclosed in this application, and includes every subgenus and all specific compounds whose structures are within the general formulas disclosed in this application. Compounds can be identified by their chemical structure and / or chemical name. When chemical structure and chemical name conflict, the chemical structure determines the nature of the compound.

[0039] The term "at least one alkyl group" as used in this application means that the organometallic compound according to the disclosure of the present invention may contain one alkyl ligand or two, three, four, five, six, or even more alkyl ligands, which may be the same or different. The number of alkyl ligands depends on the oxidation state of the Bi element in the organometallic compound, i.e., the numerical value of the valence, and depends on whether the organometallic compound is linear or cyclic, as further explained below.

[0040] The term "aliphatic" as used in this invention encompasses the terms alkyl, alkenyl, or alkynyl.

[0041] As used in this invention, the term "alkyl" refers to a saturated aliphatic hydrocarbon group comprising 1 to 8 (e.g., 1, 2, 3, 4, 5, 6, 7, or 8) carbon atoms. Alkyl groups can be straight-chain, branched, cyclic, or any combination thereof. Unless otherwise specifically defined, the term "alkyl" and the derived terms "alkoxy" and "thioalkyl," as used herein, encompass straight-chain, branched, and cyclic components within their scope. If an alkyl residue is further bonded to another atom, it becomes an alkylene residue 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," alone or as part of another substituent, refers to a saturated linear or branched divalent hydrocarbon residue obtained by removing two hydrogen atoms from a single carbon atom or two different carbon atoms of a starting alkane.

[0042] In a preferred embodiment of the present invention, the linear or branched alkyl group or alkylene group comprises 1 to 8 carbon atoms. In other, still more preferred embodiments, the linear or branched alkyl group or alkylene group comprises 1 to 6 carbon atoms. More preferably according to the present disclosure are saturated linear or branched C1 to C6 alkyl groups or saturated linear or branched C1 to C6 alkylene groups. Most preferably are linear or branched alkyl groups or alkylene groups having 1 to 4 carbon atoms. Preferred alkyl residues / components or 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-methylpropyl The alkyl or alkylene groups defined above may be unsubstituted or substituted by one or more of the substituents shown below. The term "alkyl" or "alkylene" further includes residues 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"), residues having one or more carbon-carbon triple bonds ("alkynyl"), and groups having a mixture of carbon-carbon single, double, and / or triple bonds.

[0043] The term "alkenyl" alone or as part of another substituent according to the present invention refers to an unsaturated linear or branched monovalent hydrocarbon residue having at least one carbon-carbon double bond (C=C double bond). The residue can be in a cis or trans configuration around the double bond. Thus, the term "alkenyl" also includes the corresponding cis / trans isomers. In a preferred variation according to the present invention, the linear or branched alkenyl group comprises 2 to 8 carbon atoms. In other preferred variations, the linear or branched alkenyl group comprises 2 to 6 carbon atoms. In still further preferred variations, the linear or branched alkenyl group comprises 2 to 4 carbon atoms. According to the present disclosure, mono- or di-unsaturated linear or branched C2 to C6 alkenyl groups are preferred. Typical alkenyl residues or alkenyl groups include, but are not limited to, vinyl groups; propenyl groups such as propyl-1-en-1-yl, propyl-1-en-2-yl, propyl-2-en-1-yl (allyl), propyl-2-en-2-yl, cyclopropen-1-en-1-yl, cyclopropen-2-en-1-yl; butenyl groups such as buten-1-en-1-yl, buten-1-en-2-yl, 2-methyl-propyl-1-en-1-yl, buten-2-en-1-yl, buten-2-en-2-yl, buten-1,3-dien-1-yl, buten-1,3-dien-2-yl, and the like. The alkenyl groups defined above may be unsubstituted or substituted by one or more substituents as shown below.

[0044] The term "alkynyl" alone or as part of another substituent according to the present invention refers to an unsaturated linear or branched monovalent hydrocarbon residue having at least one carbon-carbon triple bond (C≡C triple bond). In a preferred embodiment according to the present invention, the linear or branched alkynyl group comprises 2 to 8 carbon atoms. In other preferred embodiments, the alkynyl group comprises 2 to 6 carbon atoms. In still further preferred embodiments, the alkynyl group comprises 2 to 4 carbon atoms. Most preferably according to the present disclosure is a mono- or di-unsaturated linear or branched C2 to C6 alkynyl group. Typical alkynyl residues / components or alkynyl groups include, but are not limited to, ethynyl; propynyl, such as prop-1-yn-1-yl, prop-2-yn-1-yl, etc.; butynyl, such as but-1-yn-1-yl, but-1-yn-3-yl, but-3-yn-1-yl, and the like. The alkynyl group as defined above may be further substituted by one or more substituents as shown below.

[0045] The term "alkoxy" alone or as part of another substituent according to the disclosure of the present invention refers to a linear or branched residue of the general formula -OR, wherein R is an alkyl or substituted alkyl group as defined herein. In a preferred embodiment according to the disclosure of the present invention, the linear or branched alkoxy group comprises 1 to 8 carbon atoms. In other preferred embodiments, the linear or branched alkoxy group comprises 1 to 6 carbon atoms. In still further preferred embodiments, the linear or branched alkoxy group comprises 1 to 4 carbon atoms. Most preferably, in some embodiments, it is a linear or branched C1 to C6 alkoxy group. Typical alkoxy residues / components or alkoxy groups include C1 to C6 alkoxy groups, including C1 to C4 alkoxy groups such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy; and pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyl... Oxide groups, including 1-methylpentoxy, 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 defined above may be further substituted.

[0046] The terms “alkylthio” or “thioalkoxy” alone or as part of another substituent represent residues of the general formula -SR, where R is an alkyl or substituted alkyl group as defined in this application.

[0047] In this application, the terms "alkyl" or "alkylene" also include heteroalkyl residues or heteroalkyl groups. The term "heteroalkyl" refers to an alkyl group either on its own or as part of other substituents, wherein one or more carbon atoms are independently replaced by the same or another heteroatom or by the same or another heteroatom group. Examples of heteroatomic 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 the like, wherein R is independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cyclohexaalkyl, substituted cyclohexaalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, or substituted heteroarylalkyl, as defined in this application. The heteroatom or heteroatomic group may be located at any internal position of the alkyl group.

[0048] As used in this application, the term "cyclic" refers to an aliphatic cyclic compound or group containing at least three carbon atoms, and the bonds between paired adjacent atoms can all be single bonds of a specified type (involving two electrons), or some of them can be double or triple bonds (with four or six electrons, respectively). The term "cycloalkyl" as used in this invention refers to a saturated carbon ring with 3 to 8 (e.g., 3, 4, 5, 6, 7, or 8) carbon atoms. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Cycloalkyl groups as defined above can be unsubstituted or substituted by one or more substituents shown below.

[0049] As used in this application, the term "heterocyclic alkyl" refers alone or as part of another substituent to a saturated, non-aromatic, cyclic monovalent hydrocarbon residue in which one or more carbon atoms are independently replaced by the same or different heteroatoms. Typical carbon atoms used for substitution include, but are not limited to, N, B, P, O, S, Si, etc. Typical heterocyclic alkyl groups include, but are not limited to, groups derived from epoxides, azirines, cyclothioethanes, imidazolines, morpholines, piperazines, piperidines, pyrazolidines, pyrrolidones, quinine rings, and the like.

[0050] Heterocyclic alkyl components can appear as monocyclic compounds having only a single ring. Preferably, the term "heterocyclic alkyl" covers ternary to 7-membered, saturated, mono-, or polyunsaturated heterocyclic alkyl residues containing one, two, three, or four heteroatoms selected from O, N, and S. The heteroatoms or heteroatoms can occupy any position on the heterocyclic alkyl ring. In a preferred variant, the term "heterocyclic alkyl" includes ternary to 7-membered monocyclic heterocyclic alkyl residues. In other, still more preferred, variations include ternary, quaternary, pentacetic, hexavalent, 7-, or octacetic monocyclic heterocyclic alkyl residues.

[0051] Typical heterocyclic alkyl residues include, but are not limited to, tri- to six-membered saturated heterocyclic alkyl groups containing one or two nitrogen atoms and / or one oxygen or sulfur atom, or one or two oxygen and / or sulfur atoms as ring members, including aziridinyl, ethylene oxide, cyclothioethane, aziridine, oxadiazolyl, thiobutyranyl, thiobutyranyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothiophenyl, 3-tetrahydrothiophenyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isooxazolyl, 4-isooxazolyl, 5-isooxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrrolidinyl Alzolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 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-dioxane-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiophenyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperidinyl and analogues.

[0052] Heterocyclic alkyl residues or heterocyclic alkyl groups, as defined above, may be unsubstituted or substituted by one or more substituents as shown below.

[0053] The term "amine" or "amino" as used in this application includes compounds in which a nitrogen atom is covalently bonded to at least one carbon or heteroatom. The term "amine" or "amino" also includes -NH2 and also includes substituted components. The term includes "alkylamino," which includes groups and compounds in which nitrogen is bonded to at least one additional alkyl group. The term "imino" as used in this application signifies a divalent group =NR, where R represents H or an alkyl group as defined in this application. In some embodiments, the imino group may be a terminal group or bridging ligand of the general formula as defined in this application, bonded by a double bond to an element Bi(III) or Bi(V).

[0054] As used in this application, the term "alkoxy" refers to an alkyl-O- group, where "alkyl" is as defined previously. The term "alkyl thio" includes straight-chain alkyl thio, branched-chain alkyl thio, cycloalkyl thio, cyclic alkyl thio, heteroatom-unsubstituted alkyl thio, heteroatom-substituted alkyl thio, and heteroatom-unsubstituted C-... n -alkyl thiolated and heteroatom-substituted C n -Alkyl thiolation. In some embodiments, lower alkyl thiolation is contemplated.

[0055] The term "halogen" refers to a residue / component or group, either alone or as part of another substituent, such as F, Cl, Br, or I.

[0056] The phrase “optionally substituted” may be used interchangeably with the phrase “unsubstituted or substituted”. As described in this application, the compounds of the disclosures of this invention may be optionally substituted with one or more substituents, as generally described above, or as exemplified by the specific classes, subclasses, and substances of the disclosures of this invention. As described in this application, any of the components described above or those introduced below may be optionally substituted with one or more substituents described in this application.

[0057] In the context of this disclosure, the term "substitution" means that one or more hydrogen atoms of the indicated residue or group are independently replaced by the same or different substituents. Furthermore, the term "substitution" specifically refers to one or more, such as two, three, or more, substituents commonly used in the art. However, it is generally known that substituents should be selected such that they do not adversely affect the useful properties or function of the compound.

[0058] Suitable substituents in the context of this invention 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, alkyl carbonyl groups, carboxyl groups, alkoxy carbonyl groups, alkylamino carbonyl groups, dialkylamino carbonyl groups, aryl carbonyl groups, aryloxy carbonyl groups, alkyl sulfonyl groups, aryl sulfonyl groups, cycloalkyl groups, cyano groups, C1 to C6 alkyl thio groups, aryl thio groups, nitro groups, ketol groups, acyl groups, borate esters or borate esters, phosphate esters or phosphonyl groups, aminosulfonyl groups, sulfonyl groups, sulfinyl groups, and combinations thereof.

[0059] Substituents or substituent groups used to replace the saturated carbon atom in the indicated group or residue more preferably include, but are not limited to, halogens, hydroxyl groups, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, -NH2 groups, amino groups (primary, secondary, or tertiary), nitro groups, thiols, thioethers, imine groups, cyano groups, amide groups, phosphonates, phosphine groups, carboxyl groups, thiocarbonyl groups, sulfonyl groups, sulfonamide groups, ketones, aldehydes, esters, acetyl groups, acetoxy groups, carbamoyl groups, oxygen (O); haloalkyl groups (e.g., trifluoromethyl); aminoacyl and aminoalkyl groups, carbocyclic cycloalkyl groups, which may be monocyclic or fused or non-fused polycyclic (e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl), or heterocyclic alkyl groups, which may It can be a monocyclic or fused or unfused polycyclic compound (e.g., pyrrolyl, piperidinyl, piperazinyl, morpholinyl, or thiazinyl), a carbocyclic or heterocyclic compound, a monocyclic or fused or unfused polycyclic aryl compound (e.g., phenyl, naphthyl, pyrrolyl, indolyl, furanyl, thiophene, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, pyrazinyl, pyridazinyl, pyrimidinyl, benzimidazolyl, benzothiophene, or benzofuranyl), -CO2CH3, -CONH2, -OCH2CONH2; -SO2NH2, -OCHF2, -CF3, -OCF3.

[0060] Modified or derivative versions of the compounds disclosed herein are envisioned to be usable in the methods and compositions disclosed herein. Derivatives can be prepared and their properties can be evaluated for their desired performance using any method known to those skilled in the art. In some respects, “derivative” refers to a chemically modified compound that retains the desired effects of the compound prior to chemical modification.

[0061] In various embodiments, conventional materials and processing techniques can be conceived and therefore are not described in detail in this application. For example, the selection of suitable solvents, photosensitizers, pigments, fillers, antistatic agents, flame retardants, defoamers, light stabilizers, and antioxidants can be carried out in a conventional manner.

[0062] Turning now to a more specific overview of the techniques relating to aspects of the disclosure of this invention, examples of photoresists used in deep ultraviolet (DUV) and EUV lithography for 7-nm and 5-nm technology nodes include polymer-based chemically amplified photoresists and organometallic photoresists, such as organotin photoresists. These photoresist platforms may include photoacid generators and acid-insecure polymers. The acid-insecure protecting groups of such polymers can be removed by acid, resulting in alkali-soluble or volatile compounds. Organometallic photoresist platforms are also used. For example, EUV exposure can cause dissociation of the Sn-C bonds in organotin, resulting in changes in solubility or the generation of volatile products.

[0063] Typically, photoresists used for deep ultraviolet (DUV) and EUV lithography at 7-nm and 5-nm technology nodes are polymer-based chemically amplified photoresists. These photoresist platforms include photoacid generators (PAGs) and acid-insecure polymers. The acid-insecure protecting groups of such 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 cause the dissociation of Sn-C bonds in organotin, leading to changes in solubility or the generation of volatile products.

[0064] A key metric for photoresists is their sensitivity. Sensitivity is the required UV dose to print features in the photoresist. Currently available chemically amplified photoresists for EUV lithography may not be sensitive enough for a wide range of applications.

[0065] Another key metric for photoresists is their resolution, or pattern quality. Currently available chemically amplified photoresists for EUV lithography are limited in resolution and pattern quality due to the random effects involving a relatively small number of absorbed photons and the relatively long diffusion length of the acid.

[0066] Metal-organic photoresists can be more sensitive than chemically amplified photoresists. Examples of metal-organic photoresists for EUV lithography include organotin clusters, which can be applied via chemical vapor deposition (CVD) or atomic layer deposition (ALD). In these examples, EUV exposure can induce the dissociation of Sn-C bonds and inorganic SnO. x Cluster cross-linking. This leads to changes in solubility, with unexposed materials soluble in alkaline solvents and exposed materials insoluble. Although these photoresist platforms may be more sensitive in EUV than existing chemically amplified photoresists, further performance improvements are still sought.

[0067] Dry photoresists or hard masks for EUV lithography can also be more sensitive than chemically amplified photoresists. Examples of dry photoresist or hard mask platforms include organotin precursors, tetramethyltin, or tin halide precursors, tin (IV) bromide. During EUV exposure, the Sn-C or Sn-Br bond dissociates, resulting in Sn metal and, respectively, ethane or bromine. Ethane and bromine are volatile under EUV scanner processing conditions. Therefore, only Sn metal remains. Although such photoresist platforms may have higher sensitivity in EUV than chemically amplified photoresists, the processing window is challenging. Tetramethyltin is a low-boiling-point temperature liquid and evaporates rapidly from the wafer surface when vented at room temperature. Tin (IV) bromide has a near-room-temperature vapor pressure of 100 Pa, and managing the sublimation of tin (IV) bromide is challenging.

[0068] Furthermore, the toxicity and chemical waste associated with photoresists are increasingly becoming a concern. Previously, regulations were developed to control and gradually reduce fluorinated materials such as perfluorocarbons (PFOCs) and sulfur hexafluoride (SF6). It is expected that regulatory bodies will carefully review the use of fluorinated materials and the international actions to be followed regarding these materials. Currently available chemically amplified photoresists for DUV and EUV lithography have drawbacks in terms of toxicity and chemical waste due to the use of fluorinated photoacid generators.

[0069] Although metal-organic photoresist platforms and dry photoresist or hard mask platforms are generally fluorine-free, current platforms suffer from similar drawbacks due to the introduction of organotin compounds and / or bromine or chlorine reaction products, both of which are strong oxidants. Furthermore, while existing dry photoresists or hard masks for EUV lithography typically offer high sensitivity, mitigating process integration risks remains challenging.

[0070] Therefore, there is a need for photoresists for EUV lithography that possess high sensitivity, good resolution / pattern quality, low toxicity / chemical waste, and low process integration risk. This application discloses organometallic compounds that, in some embodiments, address these and other challenges. The disclosed organometallic compounds can be formulated as dry photoresist or hard mask compositions suitable for lithography processes, particularly when using EUV irradiation.

[0071] In some embodiments, the organometallic compound comprises at least one bismuth (Bi(III) or Bi(V)) element bonded to at least one terminal or bridging ligand (A) and at least one C1 to C6 alkyl ligand. The metallic element bismuth has a large absorption mode cross section for EUV photons. Examples of terminal ligands may include oxo, thionyl, 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 or an alkyl ligand, such as an alkyl ligand bonded to Bi(III) or Bi(V) element as defined herein.

[0072] The disclosed organometallic compounds for dry photoresists or hard masks used in EUV lithography 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 using fluorinated PAGs. Furthermore, the disclosed compounds are tin-free, in contrast to currently available organometallic photoresists and dry photoresists or hard masks used in EUV lithography.

[0073] The disclosed organometallic compounds for dry photoresists or hard masks used in EUV lithography also offer advantages over existing materials in terms of resolution and pattern quality: the disclosed organometallic molecules have high melting temperatures and, consequently, high activation energies for diffusion. Therefore, the disclosed molecules can exhibit low diffusion coefficients under EUV scanner processing conditions. Furthermore, the disclosed organometallic molecules possess high density and, consequently, low shrinkage when inorganic clusters crosslink during EUV exposure.

[0074] The organometallic molecules taught in this application for use in dry photoresists or hard masks for EUV lithography can have a high absorption mode cross-section for photons in EUV. Therefore, the disclosed compounds can have high sensitivity in EUV. The disclosed organometallic molecules for dry photoresists or hard masks for EUV lithography can also have low process integration risk: for example, the disclosed compounds have high melting point temperatures and are solids with very low vapor pressures under the conditions (vacuum) found in EUV scanners.

[0075] Figure 1 This shows the photon absorption mode cross section µ of all natural elements at 92 eV. a The figure shows that, in order to design materials that can be used to increase the sensitivity of photoresists for EUV lithography, it is crucial to understand and recognize the microscopic mechanisms that induce photon absorption activity in EUV, in contrast to those in DUV.

[0076] DUV (193nm, 6eV) photon absorption is determined by the molecular orbitals of the photoresist material. Absorbed photons can directly and selectively induce resonant electronic transitions in the photoacid generator, leading to acid generation. The sensitivity of chemically amplified photoresists for DUV lithography can be increased by adjusting the molecular structure of the photoacid generator. EUV (13.5nm, 92eV, soft X-ray) photon absorption, on the other hand, is determined by the atomic composition of the photoresist material, rather than its molecular structure.

[0077] The absorption of photons in a layer of thickness d is determined by 1 - exp(-n µ). a d) is given, where n is the number of atoms per unit volume in the layer. To increase the 92-eV photon absorption mode cross-section of the photoresist, elements with a large absorption mode cross-section at this photon energy can be added to the photoresist composition. For example, elements In, Sn, Sb, Te, Bi, Sb, and Po have large absorption mode cross-sections for EUV photons. Among these, bismuth (Bi) can be advantageous in terms of toxicity, stability, and cost.

[0078] In this application, the organometallic compound used for dry photoresist or hard mask in EUV lithography includes metal element Bi in its oxidation state (III) or metal element Bi in its oxidation state (V). Providing ligand A to metal element Bi can increase the melting point temperature of the molecule, and consequently, increase the activation energy for diffusion of the molecule, thus reducing the diffusion coefficient of the molecule under processing conditions in an EUV scanner.

[0079] The reaction products formed by C1 to C6 alkyl ligands of organometallic compounds during EUV exposure can be selected. These products, except for inorganic clusters (Bi=O, Bi=S, Bi=N, Bi-O, Bi-S, or Bi-N clusters), are volatile under EUV scanner processing conditions. EUV exposure causes the dissociation of Bi-C and NR bonds in the organometallic compound. Upon dissociation, the alkyl groups can become free radicals and crosslink with inorganic Bi=O, Bi=S, Bi=N, Bi-O, Bi-S, or Bi=N clusters. The resulting C1 to C6 alkyl residues then pair and react with each other to form C2 to C12 alkyl substances, which are volatile and evaporable. For example, when the alkyl ligand is methyl or ethyl, the volatile products are ethane or butane, respectively. After the volatile organic alkyl substances evaporate, the non-volatile crosslinked inorganic clusters can remain on the substrate as reaction products.

[0080] Organometallic compounds can be represented by general formulas (I), (II), (III), (IV), (V), (VI), and (VII):

[0081]

[0082] General formula (I),

[0083]

[0084] General formula (II),

[0085]

[0086] General formula (III),

[0087]

[0088] General formula (IV),

[0089]

[0090] General formula (V),

[0091]

[0092] General formula (VI), and

[0093]

[0094] General formula (VII),

[0095] In general formulas (I), (II), (III), (IV), (V), (VI), and (VII), A may represent O, S, or NR; each of R1, R2, R3, R4, R5, R6, R7, and R8 may represent an optionally substituted linear or branched C1 to C6 alkyl, an optionally substituted C3 to C6 cycloalkyl, or an optionally substituted C3 to C6 heterocyclic alkyl; n may be an integer from 1 to 4; m may be an integer from 2 to 5; and R in NR may represent H or an optionally substituted linear or branched C1 to C6 alkyl, an optionally substituted C3 to C6 cycloalkyl, or an optionally substituted C3 to C6 heterocyclic alkyl.

[0096] In a preferred embodiment, the organometallic compound is a single compound according to general formula (I), wherein Bi is in oxidation state (III), or a single compound according to general formula (IV), wherein Bi is in oxidation state (V). In a more preferred embodiment, the organometallic compound is a linear, acyclic compound according to general formula (II), (V), or (VI), wherein 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 according to general formula (III) or (VII), wherein m is an integer from 2 to 4. Most preferably, m is 2 or 3.

[0097] In some embodiments, in the organometallic compound 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 C6 alkyl, optionally substituted C3 to C6 cycloalkyl, or optionally substituted C3 to C6 heterocyclic alkyl, particularly optionally substituted linear C1 to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, or optionally substituted C3 to C6 heterocyclic alkyl.

[0098] In a further embodiment, in the organometallic compound 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 C5 alkyl, optionally substituted C3 to C5 cycloalkyl, or optionally substituted C3 to C5 heterocyclic alkyl, particularly optionally substituted linear C1 to C5 alkyl, optionally substituted C3 to C5 cycloalkyl, or optionally substituted C3 to C5 heterocyclic alkyl.

[0099] In a further embodiment, in the organometallic compound 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 C4 alkyl, optionally substituted C3 or C4 cycloalkyl, or optionally substituted C3 or C4 heterocyclic alkyl, particularly optionally substituted linear C1 to C4 alkyl, optionally substituted C3 or C4 cycloalkyl, or optionally substituted C3 or C4 heterocyclic alkyl.

[0100] In a further embodiment, in the organometallic compound 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, optionally substituted C3 cycloalkyl, or optionally substituted C3 heterocyclic alkyl, particularly optionally substituted linear C1 to C3 alkyl, optionally substituted C3 cycloalkyl, or optionally substituted C3 heterocyclic alkyl.

[0101] In another embodiment, in the organometallic compound 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.

[0102] In organometallic compounds represented by any one of the general formulas (I) to (VII) specified above, R1, R2, R3, R4, R5, R6, R7, R8, or RN may be the same as or different from each other. For ease of synthesis, the alkyl ligands R1, R2, R3, R4, R5, R6, R7, R8, or RN may be the same.

[0103] In a preferred embodiment, the organometallic compound is composed of Figure 2 Any one of the general formulas (a) to (j) shown is represented. In a further preferred embodiment, the organometallic compound is derived from... Figure 3A Any one of the general formulas (a) to (o) shown Figure 3B Any one of the general formulas (p) to (ad) shown in the figure. Figure 3A and 3B The compounds shown include single, linear and cyclic organometallic compounds according to general formulas (I), (II), (III), (IV), (VI), or (VII), wherein A = O, S or NR, and n is 1 or 2, or m is 2 or 3.

[0104] Figure 2This is a set of chemical structure diagrams of organometallic compounds (a) to (j) for use in dry photoresists or hard masks for EUV lithography, according to some 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)-(j), A may represent a substance selected from O, S, and NR; and 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 may independently represent optionally substituted linear or branched C1 to C6 alkyl groups, optionally substituted C3 to C6 cycloalkyl groups, or optionally substituted C3 to C6 heterocycloalkyl groups. In NR, R can represent H or optionally substituted linear or branched C1 to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, or optionally substituted C3 to C6 heterocycloalkyl.

[0105] In a more preferred variation, in which... Figure 2 In any of the organometallic compounds represented by general formulas (a) to (j), 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 C6 alkyl, optionally substituted C3 to C6 cycloalkyl, or optionally substituted C3 to C6 heterocyclic alkyl, particularly optionally substituted linear C1 to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, or optionally substituted C3 to C6 heterocyclic alkyl.

[0106] In a more preferred variation, in which... Figure 2 In any of the organometallic compounds represented by general formulas (a) to (j), 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 C5 alkyl, optionally substituted C3 to C5 cycloalkyl, or optionally substituted C3 to C5 heterocyclic alkyl, particularly optionally substituted linear C1 to C5 alkyl, optionally substituted C3 to C5 cycloalkyl, or optionally substituted C3 to C5 heterocyclic alkyl.

[0107] In a more preferred variation, in which... Figure 2In any of the organometallic compounds represented by general formulas (a) to (j), 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 C4 alkyl, optionally substituted C3 to C4 cycloalkyl, or optionally substituted C3 to C4 heterocyclic alkyl, particularly optionally substituted linear C1 to C4 alkyl, optionally substituted C3 or C4 cycloalkyl, or optionally substituted C3 or C4 heterocyclic alkyl.

[0108] In a further optimized variation, in which... Figure 2 In any of the organometallic compounds represented by general formulas (a) to (j), 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, optionally substituted C3 cycloalkyl, or optionally substituted C3 heterocyclic alkyl, particularly optionally substituted linear C1 to C3 alkyl, optionally substituted C3 cycloalkyl, or optionally substituted C3 heterocyclic alkyl.

[0109] In even better variations, in which... Figure 2 In any of the organometallic compounds represented by general formulas (a) to (j), 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.

[0110] Figure 3A These are sets of chemical structure diagrams (a) to (o) representing single, linear, or cyclic organometallic compounds used in dry photoresists or hard masks for EUV lithography, wherein Bi is in the oxidation state (III), according to some embodiments. Figure 3A middle:

[0111] (a) In general formula (I), A is O;

[0112] (b) In general formula (II), A is O and n=1;

[0113] (c) In general formula (II), A is O and n=2;

[0114] (d) In general formula (III), A is O and m=2;

[0115] (e) In general formula (III), A is O and m=3;

[0116] (f) In general formula (I), A is S;

[0117] (g) In general formula (II), A is S and n=1;

[0118] (h) In general formula (II), A is S and n=2;

[0119] (i) In general formula (III), A is S and m=2;

[0120] (j) In general formula (III), A is S and m=3;

[0121] (k) In general formula (I), A is NR;

[0122] (l) In general formula (II), A is NR and n=1;

[0123] (m) In general formula (II), A is NR and n=2;

[0124] (n) In general formula (III), A is NR and m=2; and

[0125] (o) In general formula (III), A is NR and m=3.

[0126] exist Figure 3A In the general formulas (a) to (o) shown, R1, R2, R3, R4, R1 / 1, R1 / 2, R1 / 3, RN / 1, RN / 2, and RN / 3 can independently represent optionally substituted linear or branched C1 to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, or optionally substituted C3 to C6 heterocycloalkyl.

[0127] In a more preferred variation, Figure 3A In any of the organometallic compounds represented by general formulas (a) to (o), 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 C6 alkyl, optionally substituted C3 to C6 cycloalkyl, or optionally substituted C3 to C6 heterocyclic alkyl, particularly optionally substituted linear C1 to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, or optionally substituted C3 to C6 heterocyclic alkyl.

[0128] In a more preferred variation, Figure 3A In any of the organometallic compounds represented by general formulas (a) to (o), 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 C5 alkyl, optionally substituted C3 to C5 cycloalkyl, or optionally substituted C3 to C5 heterocyclic alkyl, particularly optionally substituted linear C1 to C5 alkyl, optionally substituted C3 to C5 cycloalkyl, or optionally substituted C3 to C5 heterocyclic alkyl.

[0129] In a more preferred variation, Figure 3A In any of the organometallic compounds represented by general formulas (a) to (o), 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, optionally substituted C3 to C4 cycloalkyl, or optionally substituted C3 to C4 heterocyclic alkyl, particularly optionally substituted linear C1 to C4 alkyl, optionally substituted C3 or C4 cycloalkyl, or optionally substituted C3 or C4 heterocyclic alkyl.

[0130] In a further optimized variation, Figure 3A In any of the organometallic compounds represented by general formulas (a) to (o), 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, optionally substituted C3 cycloalkyl, or optionally substituted C3 heterocyclic alkyl, particularly optionally substituted linear C1 to C3 alkyl, optionally substituted C3 cycloalkyl, or optionally substituted C3 heterocyclic alkyl.

[0131] In even better variations, Figure 3A In any of the organometallic compounds represented by general formulas (a) to (o), 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.

[0132] Figure 3B These are sets of chemical structure diagrams (p) to (ad) representing single, linear, or cyclic organometallic compounds used in dry photoresists or hard masks for EUV lithography, wherein Bi is in an oxidized state (V), according to some embodiments. Figure 3B middle:

[0133] (p) In general formula (IV), A is O;

[0134] (q) In general formula (VI), A is O and n=1;

[0135] (r) In general formula (VI), A is O and n=2;

[0136] (s) In general formula (VII), A is O and m=2;

[0137] (t) In general formula (VII), A is O and m=3;

[0138] (u) In general formula (IV), A is S;

[0139] (v) In general formula (VI), A is S and n=1;

[0140] (w) In general formula (VI), A is S and n=2;

[0141] (x) In general formula (VII), A is S and m=2;

[0142] (y) In general formula (VII), A is S and m=3;

[0143] (z) In general formula (IV), A is NR;

[0144] (aa) In general formula (VI), A is NR and n=1;

[0145] (ab) In general formula (VI), A is NR and n=2;

[0146] (ac) In general formula (VII), A is NR and m=2; and

[0147] (ad) In general formula (VII), A is NR and m=3.

[0148] exist Figure 3B In the general formulas (p) to (ad) shown, the bismuth element is Bi(V), and 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 can independently represent an optionally substituted linear or branched C1 to C6 alkyl, an optionally substituted C3 to C6 cycloalkyl, or an optionally substituted heterocyclic alkyl.

[0149] In a more preferred variation, in which... Figure 3B In any of the organometallic compounds represented by general formulas (p) to (ad), 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 C6 alkyl, optionally substituted C3 to C6 cycloalkyl, or optionally substituted C3 to C6 heterocyclic alkyl, particularly optionally substituted linear C1 to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, or optionally substituted C3 to C6 heterocyclic alkyl.

[0150] In a more preferred variation, in which... Figure 3BIn any of the organometallic compounds represented by general formulas (p) to (ad), 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 C5 alkyl, optionally substituted C3 to C5 cycloalkyl, or optionally substituted C3 to C5 heterocyclic alkyl, particularly optionally substituted linear C1 to C5 alkyl, optionally substituted C3 to C5 cycloalkyl, or optionally substituted C3 to C5 heterocyclic alkyl.

[0151] In a more preferred variation, in which... Figure 3B In any of the organometallic compounds represented by general formulas (p) to (ad), 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 C4 alkyl, optionally substituted C3 to C4 cycloalkyl, or optionally substituted C3 to C4 heterocyclic alkyl, particularly optionally substituted linear C1 to C4 alkyl, optionally substituted C3 or C4 cycloalkyl, or optionally substituted C3 or C4 heterocyclic alkyl.

[0152] In a further optimized variation, in which... Figure 3B In any of the organometallic compounds represented by general formulas (p) to (ad), 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, optionally substituted C3 cycloalkyl, or optionally substituted C3 heterocyclic alkyl, particularly optionally substituted linear C1 to C3 alkyl, optionally substituted C3 cycloalkyl, or optionally substituted C3 heterocyclic alkyl.

[0153] In even better variations, in which... Figure 3B In any of the organometallic compounds represented by general formulas (p) to (ad), 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.

[0154] Figure 4A-5B Based on some implementation schemes, this describes a set of chemical structure diagrams of individual organometallic compounds, represented by general formulas (I) and (IV), used for dry photoresist or hard masks for EUV lithography.

[0155] Figure 4A and4B This shows a particularly preferred single organometallic compound represented by general formula (I) or (IV), wherein 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 (e.g., methyl, ethyl, propyl or butyl).

[0156] exist Figure 4A middle:

[0157] (a) bismuthanone;

[0158] (b) Ethylbismuth ketone;

[0159] (c) Propylbismuth ketone;

[0160] (d) Butylbismuth ketone;

[0161] (e) bismuthanethione;

[0162] (f) Ethylbismuthylthione;

[0163] (g) Propylbismuthylthione;

[0164] (h) Butylbismuthylthione;

[0165] (i) Bi-methylbismuthaneimine;

[0166] (j)Bi-ethylbismuth alkylimine;

[0167] (k)Bi-propylbismuthaneimine; and

[0168] (l)Bi-Butylbismuthaneimine.

[0169] exist Figure 4B middle:

[0170] (a) Trimethyl-λ 5 - Bismuth ketone;

[0171] (b) Triethyl-λ 5 - Bismuth ketone;

[0172] (c) Tripropyl-λ 5 - Bismuth ketone;

[0173] (d) Tributyl-λ 5 - Bismuth ketone;

[0174] (e)trimethyl-λ 5 - Bismuthylthione;

[0175] (f) Triethyl-λ 5 - Bismuthylthione;

[0176] (g) Tripropyl-λ 5 - Bismuthylthione;

[0177] (h)tributyl-λ 5 - Bismuthylthione;

[0178] (i)Bi,Bi,Bi-trimethyl-λ 5 -bismuthaneimine;

[0179] (j)Bi,Bi,Bi-triethyl-λ 5 -bismuthaneimine;

[0180] (k)Bi,Bi,Bi-tripropyl-λ 5 -bismuthaneimine; and

[0181] (l)Bi,Bi,Bi-tributyl-λ 5 -Bismuthaneimine.

[0182] Figure 4C and 4D The particularly preferred single organometallic compounds are represented by general formulas (I) and (IV), wherein Bi is in oxidation state (III) or (V), A is O, S or NR, and alkyl ligands R1, R2 and R3 are branched C3 or C4 alkyl (e.g., isopropyl or tert-butyl).

[0183] exist Figure 4C middle:

[0184] (a) Propan-2-ylbismuth ketone;

[0185] (b) tert-butylbismuth ketone;

[0186] (c) Propan-2-ylbismuthiophene;

[0187] (d) tert-butylbismuth thione;

[0188] (e)Bi-propane-2-ylbismuthaneimine; and

[0189] (f)Bi-tert-butylbismuth alkylimine.

[0190] exist Figure 4D middle:

[0191] (a) Tris(propan-2-yl)-λ 5 - Bismuth ketone;

[0192] (b) Tri(tert-butyl)-λ 5 - Bismuth ketone;

[0193] (c) Tris(propan-2-yl)-λ 5 - Bismuthylthione;

[0194] (d) Tri(tert-butyl)-λ 5 - Bismuthylthione;

[0195] (e)Bi,Bi,Bi-tris(propan-2-yl)-λ 5 -bismuthaneimine; and

[0196] (f)Bi,Bi,Bi-tris(tert-butyl)-λ 5 -Bismuthaneimine.

[0197] Figure 5A and 5B The preferred single organometallic compound is represented by general formula (I) or (IV), wherein 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).

[0198] exist Figure 5A middle:

[0199] (a) Cyclopropylbismuth ketone;

[0200] (b) Cyclobutylbismuth ketone;

[0201] (c) Cyclopropylbismuthylthione;

[0202] (d) Cyclobutylbismuthylthione;

[0203] (e)Bi-cyclopropylbismuthaneimine; and

[0204] (f)Bi-cyclobutylbismuth alkylimine.

[0205] exist Figure 5B middle:

[0206] (a) Tricyclopropyl-λ 5 - Bismuth ketone;

[0207] (b) Tricyclobutyl-λ 5 - Bismuth ketone;

[0208] (c) Tricyclopropyl-λ 5 - Bismuthylthione;

[0209] (d) Tricyclobutyl-λ 5 - Bismuthylthione;

[0210] (e)Bi,Bi,Bi-tricyclopropyl-λ 5 -bismuthaneimine; and

[0211] (f)Bi,Bi,Bi-tricyclobutyl-λ 5 -Bismuthaneimine.

[0212] Figures 6A-7B Based on some implementation schemes, this describes a set of chemical structure diagrams of linear organometallic compounds, represented by general formulas (II), (V), and (VI), for use in dry photoresists or hard masks for EUV lithography.

[0213] Figure 6A and 6B The particularly preferred linear organometallic compounds are represented by general formulas (II), (V), or (VI), wherein 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.

[0214] exist Figure 6A middle:

[0215] (a) Dimethylbismuthoxy(dimethyl)bismuthane;

[0216] (b) bis(dimethylbismuthoxy)(methyl)bismuthane;

[0217] (c) Dimethylbismuthylthioalkyl(dimethyl)bismuthane;

[0218] (d) Bis(dimethylbismuthylthio)(methyl)bismuthane;

[0219] (e) bis(dimethylbismuthyl)amine; and

[0220] (f) Dimethylbismuthylamino(methyl)bismuthyl(dimethylbismuthyl)amine.

[0221] exist Figure 6B middle:

[0222] (a) Tetramethyl-λ 5 -bismuthalkoxy(tetramethyl)-λ 5 - Bismuthane;

[0223] (b) Bis(tetramethyl-λ) 5 -bismuthoxy)(trimethyl)-λ 5 - Bismuthane;

[0224] (c) Tetramethyl-λ 5 -bismuthylthioalkyl(tetramethyl)-λ 5 - Bismuthane;

[0225] (d) Bis(tetramethyl-λ) 5 -bismuthylthio(trimethyl)-λ 5 - Bismuthane;

[0226] (e) bis(tetramethyl-λ)5 -bismuthyl)amine; and

[0227] (f) Tetramethyl-λ 5 -bismuthylamino(trimethyl)-λ 5 -bismuthyl) (tetramethyl-λ 5 Bismuth alkylamines.

[0228] Figure 7A and 7B The preferred linear organometallic compounds are represented by general formulas (II), (V), or (VI), wherein 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 a further embodiment, the alkyl ligand may be cyclobutyl.

[0229] exist Figure 7A middle:

[0230] (a) Dicyclopropylbismuthalkoxy(dicyclopropyl)bismuthane;

[0231] (b) Bis(dicyclopropylbismuthalkoxy)(cyclopropyl)bismuthane;

[0232] (c) Dicyclopropylbismuthylthioalkyl(dicyclopropyl)bismuthane;

[0233] (d) Bis(dicyclopropylbismuthylthioalkyl)(cyclopropyl)bismuthane;

[0234] (e) bis(dicyclopropylbismuthyl)amine; and

[0235] (f) Dicyclopropylbismuthylamino(cyclopropyl)bismuthyl(di-cyclopropylbismuthyl)amine.

[0236] exist Figure 7B middle:

[0237] (a) Tetracyclopropyl-λ 5 -bismuthalkoxy(tetracyclopropyl)-λ 5 - Bismuthane;

[0238] (b) Bis(tetracyclopropyl-λ) 5 -bismuthoxy)(tricyclopropyl)-λ 5 - Bismuthane;

[0239] (c) Tetracyclopropyl-λ 5 -bismuthylthioalkyl(tetracyclopropyl)-λ 5 - Bismuthane;

[0240] (d) Bis(tetracyclopropyl-λ) 5 -bismuthylthioalkyl)(tricyclopropyl)-λ 5 - Bismuthane;

[0241] (e) Bis(tetracyclopropyl-λ) 5 -bismuthyl)amine; and

[0242] (f) Tetracyclopropyl-λ 5 -bismuth alkylamino(tricyclopropyl-λ) 5 -bismuthyl) (tetracyclopropyl-λ 5 -bismuthyl)amine.

[0243] Figures 8A-9B Based on some implementation schemes, this describes a set of chemical structure diagrams of cyclic organometallic compounds represented by general formulas (III) and (VII) for use in dry photoresists or hard masks for EUV lithography.

[0244] Figure 8A and 8B The particularly preferred cyclic organometallic compounds are represented by general formula (III) or (VII), wherein Bi is in oxidation state (III) or (V); A is O, S or NR; m is 2; and alkyl ligands R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, and R3 / 2 are methyl, ethyl, propyl or butyl.

[0245] exist Figure 8A middle:

[0246] (a) 2,4-Dimethyl-1,3,2,4-dioxabismuth tetracyclic ring;

[0247] (b) 2,4-Diethyl-1,3,2,4-dioxabismuth tetracyclo;

[0248] (c)2,4-Dipropyl-1,3,2,4-Dioxabismutha tetracyclo;

[0249] (d)2,4-Dibutyl-1,3,2,4-Dioxabismutha tetracyclic;

[0250] (e)2,4-Dimethyl-1,3,2,4-dithiabismutha tetracyclic;

[0251] (f)2,4-Diethyl-1,3,2,4-dithiabismutha tetracyclo;

[0252] (g)2,4-Dipropyl-1,3,2,4-Dithiabismutha tetracyclic;

[0253] (h)2,4-Dibutyl-1,3,2,4-Dithiabismutha tetracyclic;

[0254] (i) 2,4-Dimethyl-1,3,2,4-diazabismuth tetracyclic;

[0255] (j)2,4-Diethyl-1,3,2,4-diazabismuth tetracyclo;

[0256] (k)2,4-dipropyl-1,3,2,4-diazabismuth tetracyclic; and

[0257] (l)2,4-Dibutyl-1,3,2,4-diazabismuth tetracyclic.

[0258] exist Figure 8B middle:

[0259] (a)2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxa-λ 5 - Bismetane;

[0260] (b)2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadi-λ 5 -Bismuth tetracyclic rings;

[0261] (c)2,2,2,4,4,4-hexapropyl-1,3,2,4-dioxadi-λ 5 -Bismuth tetracyclic rings;

[0262] (d)2,2,2,4,4,4-hexabutyl-1,3,2,4-dioxadi-λ 5 -Bismuth tetracyclic rings;

[0263] (e)2,2,2,4,4,4-hexamethyl-1,3,2,4-dithia-λ 5 -Bismuth tetracyclic rings;

[0264] (f)2,2,2,4,4,4-hexaethyl-1,3,2,4-dithiadi-λ 5 -Bismuth tetracyclic rings;

[0265] (g)2,2,2,4,4,4-hexapropyl-1,3,2,4-dithiadi-λ 5 -Bismuth tetracyclic rings;

[0266] (h)2,2,2,4,4,4-hexabutyl-1,3,2,4-dithiadi-λ 5 -Bismuth tetracyclic rings;

[0267] (i)2,2,2,4,4,4-hexamethyl-1,3,2,4-diazabi-λ 5 -Bismuth tetracyclic rings;

[0268] (j)2,2,2,4,4,4-hexaethyl-1,3,2,4-diazabi-λ 5 -Bismuth tetracyclic rings;

[0269] (k)2,2,2,4,4,4-hexapropyl-1,3,2,4-diazabi-λ 5 -Bismuth tetracyclic rings; and

[0270] (l)2,2,2,4,4,4-hexabutyl-1,3,2,4-diazabi-λ 5 -Bismuth tetracyclic rings.

[0271] Figure 9A and 9B The preferred cyclic organometallic compound is represented by general formula (III) or (VII), wherein Bi is in oxidation state (III) or (V); A is O, S or NR, m is 2; and alkyl ligands R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, and R3 / 2 are cyclopropyl or cyclobutyl.

[0272] exist Figure 9A middle:

[0273] (a) 2,4-Bicyclopropyl-1,3,2,4-Dioxabismutha tetracyclo;

[0274] (b) 2,4-Bicyclobutyl-1,3,2,4-Dioxadibismuth tetracyclo;

[0275] (c)2,4-Bicyclopropyl-1,3,2,4-Dithiabismutha tetracyclo;

[0276] (d)2,4-Bicyclobutyl-1,3,2,4-Dithiobismuth tetracyclo;

[0277] (e)2,4-Bicyclopropyl-1,3,2,4-diazabismuth heterotetracyclo; and

[0278] (f)2,4-Bicyclobutyl-1,3,2,4-diazabismuth tetracyclo

[0279] exist Figure 9B middle:

[0280] (a)2,2,2,4,4,4-hexanepropyl-1,3,2,4-dioxadi-λ 5 -Bismuth tetracyclic rings;

[0281] (b)2,2,2,4,4,4-hexanebutyl-1,3,2,4-dioxadi-λ 5 -Bismuth tetracyclic rings;

[0282] (c)2,2,2,4,4,4-hexanepropyl-1,3,2,4-dithiadi-λ 5 -Bismuth tetracyclic rings;

[0283] (d)2,2,2,4,4,4-hexanebutyl-1,3,2,4-dithiadi-λ 5 -Bismuth tetracyclic rings;

[0284] (e)2,2,2,4,4,4-hexanepropyl-1,3,2,4-diazabi-λ 5 -Bismuth tetracyclic rings; and

[0285] (f)2,2,2,4,4,4-hexanebutyl-1,3,2,4-diazabi-λ 5 -Bismuth tetracyclic rings.

[0286] Figure 10A-11B Based on some implementation schemes, this describes a set of chemical structure diagrams of cyclic organometallic compounds represented by general formulas (III) and (VII) for use in dry photoresists or hard masks for EUV lithography.

[0287] Figure 10A and 10B The particularly preferred cyclic organometallic compounds are represented by general formula (III) or (VII), wherein Bi is in oxidation state (III) or (V); A is O, S, NR, m is 3; and alkyl ligands R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, and R3 / 2 are methyl, ethyl, propyl, or butyl.

[0288] exist Figure 10A middle:

[0289] (a) 2,4,6-trimethyl-1,3,5,2,4,6-trioxabismuth-hexacyclic (tribismuth-hexacyclic);

[0290] (b) 2,4,6-triethyl-1,3,5,2,4,6-trioxabismuth-hexacyclo ...

[0291] (c)2,4,6-tripropyl-1,3,5,2,4,6-trioxabismuth-hexacyclo ...

[0292] (d)2,4,6-Tributyl-1,3,5,2,4,6-Trioxanetribismuth-hexacyclo ...

[0293] (e)2,4,6-Trimethyl-1,3,5,2,4,6-trithiabismuthacyclohexa ...

[0294] (f)2,4,6-Triethyl-1,3,5,2,4,6-Trithiabismuth-hexacyclo ...

[0295] (g)2,4,6-tripropyl-1,3,5,2,4,6-trithiabismuthacyclohexa ...

[0296] (h)2,4,6-Tributyl-1,3,5,2,4,6-Trithiabismuth-hexacyclo ...

[0297] (i)2,4,6-trimethyl-1,3,5,2,4,6-triazabismuth-hexacyclo ...

[0298] (j)2,4,6-triethyl-1,3,5,2,4,6-triazabismuth-hexacyclo ...

[0299] (k)2,4,6-tripropyl-1,3,5,2,4,6-triazabismuth-hexacyclic; and

[0300] (l)2,4,6-Tributyl-1,3,5,2,4,6-Triazabismuth-hexacyclo ...

[0301] exist Figure 10B middle:

[0302] (a)2,2,2,4,4,4,6,6,6-Nonmethyl-1,3,5,2,4,6-trioxatri-λ 5 - Bismuth heterocyclic ring (bismane);

[0303] (b)2,2,2,4,4,4,6,6,6-Nonethyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismuth heterocyclic rings;

[0304] (c)2,2,2,4,4,4,6,6,6-Nine-propyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismuth heterocyclic rings;

[0305] (d)2,2,2,4,4,4,6,6,6-nonbutyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismuth heterocyclic rings;

[0306] (e)2,2,2,4,4,4,6,6,6-Nonmethyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismuth heterocyclic rings;

[0307] (f)2,2,2,4,4,4,6,6,6-Nonethyl-1,3,5,2,4,6-trithione-λ 5 -Bismuth heterocyclic rings;

[0308] (g)2,2,2,4,4,4,6,6,6-Nine-propyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismuth heterocyclic rings;

[0309] (h)2,2,2,4,4,4,6,6,6-nonbutyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismuth heterocyclic rings;

[0310] (i)2,2,2,4,4,4,6,6,6-Nonmethyl-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic rings;

[0311] (j)2,2,2,4,4,4,6,6,6-Nonethyl-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic rings;

[0312] (k)2,2,2,4,4,4,6,6,6-Ninepropyl-1,3,5,2,4,6-Triazatri-λ 5 -Bismuth heterocyclic rings; and

[0313] (l)2,2,2,4,4,4,6,6,6-nonadenylated-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic rings.

[0314] Figure 11A and 11B The preferred cyclic organometallic compound is represented by general formula (III) or (VII), wherein Bi is in oxidation state (III) or (V); A is O, S, NR, m is 3; and alkyl ligands R1 / 1, R2 / 1, R3 / 1, R1 / 2, R2 / 2, and R3 / 2 are cyclopropyl or cyclobutyl.

[0315] exist Figure 11A middle:

[0316] (a) 2,4,6-Tricyclopropyl-1,3,5,2,4,6-trioxabismuth-hexacyclo ...

[0317] (b) 2,4,6-Tricyclobutyl-1,3,5,2,4,6-Trioxanetribismuth-hexacyclo ...

[0318] (c)2,4,6-Tricyclopropyl-1,3,5,2,4,6-Trithiabismuth-hexacyclo ...

[0319] (d)2,4,6-Tricyclobutyl-1,3,5,2,4,6-Trithiabismuth-hexacyclo ...

[0320] (e)2,4,6-Tricyclopropyl-1,3,5,2,4,6-triazabismuth-hexacyclo ...

[0321] (f)2,4,6-Tricyclobutyl-1,3,5,2,4,6-Triazabismuth-hexacyclo ...

[0322] exist Figure 11B middle:

[0323] (a)2,2,2,4,4,4,6,6,6-Ninecyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismuth heterocyclic rings;

[0324] (b)2,2,2,4,4,4,6,6,6-Ninecyclobutyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismuth heterocyclic rings;

[0325] (c)2,2,2,4,4,4,6,6,6-Ninecyclopropyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismuth heterocyclic rings;

[0326] (d)2,2,2,4,4,4,6,6,6-Nine-cyclobutyl-1,3,5,2,4,6-trithiatri-λ 5 -Bismuth heterocyclic rings;

[0327] (e)2,2,2,4,4,4,6,6,6-Ninecyclopropyl-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic rings; and

[0328] (f)2,2,2,4,4,4,6,6,6-Ninecyclobutyl-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic rings.

[0329] When A is NR, in the above-mentioned preferred organometallic compounds of general formulas (I) to (VII), R or the R-group (RN / 1, RN / 2, or RN / 3) is H; linear C1 to C4 alkyl, such as methyl, ethyl, propyl, or butyl; or branched C3 or C4 alkyl, such as isopropyl or tert-butyl; or cyclic C3 or C4 alkyl, such as cyclopropyl or cyclobutyl. Preferably, R is the same as the alkyl ligand of the organometallic compound.

[0330] In the disclosed organometallic compounds containing Bi for use as dry photoresists or hard masks for EUV lithography, Bi; a terminal oxoligand, a terminal thionyl ligand, a terminal imino ligand, an oxygen-bridged ligand, a sulfur-bridged ligand, or an aminoalkyl-bridged ligand; and one of a C1 to C4 alkyl ligand, the molecular composition and structure can be advantageously selected such that:

[0331] (i) At room temperature, the diffusion coefficient of the molecule should be low. For this purpose, the composition and structure of the molecule can be chosen to result in a high melting point temperature. Terminal oxoligands, terminal thionyl ligands, terminal imino ligands, oxygen-bridged ligands, sulfur-bridged ligands, or amino-bridged ligands cause the melting point temperature of the molecule to be substantially above room temperature, even when the alkyl ligand is methyl (C1). The melting point temperature can be further adjusted (e.g., to about 180 K) by increasing the length of the alkyl ligand from C1 to C4.

[0332] (ii) During EUV exposure, the Bi-C and NC bonds dissociate and crosslink with inorganic Bi=O, Bi-O, Bi=S, Bi-S, Bi=N, or Bi-N clusters. These clusters are non-volatile.

[0333] (iii) Alkyl ligands may be selected such that the reaction product is volatile under EUV scanner processing conditions, except for Bi=O, Bi-O, Bi=S, Bi-S, Bi=N, or Bi-N clusters, upon EUV exposure. Therefore, C1 to C4 alkyl ligands are preferred.

[0334] (iv) Since the shrinkage due to material volatilization during EUV exposure should be appropriate, C1 to C3 alkyl ligands are still more preferred as alkyl ligands.

[0335] Regarding the diffusion coefficient (i), it is generally found that the diffusion coefficient in solids is well represented by an Arrhenius-type relationship curve exp(E). A / kT) prediction, where diffusion uses activation energy E A It is a first-order approximation—proportional to the melting point temperature of the solid. It was found that the melting point temperature of organometallic molecules is crucial for selecting preferred organometallic molecules due to the exponential correlation between the diffusion coefficient and melting point temperature.

[0336] Therefore, it is preferable to have organometallic molecules that have a high melting point temperature and are therefore solids with very low vapor pressure under vacuum conditions as observed in EUV scanners.

[0337] The melting point temperature T of bismuth ketone organometallic molecules used in dry photoresists or hard masks for EUV lithography M Reasonable predictions can be made by considering the boiling point temperatures T of the organometallic molecular series tetraalkyltinane, trialkylantimonane, and trialkylbismuthane. B And by achieving, for example, the melting temperature T of dimethyltin oxide. M It was obtained at approximately 380℃.

[0338] For tetramethylstanane and tetrapropylstanane, their respective boiling point temperatures T BThe boiling points T for trimethylantimonane and tripropylantimonane are approximately 80°C and 220°C, respectively. B The temperatures are approximately 80°C and 210°C, and the respective boiling points T for trimethylbismuthane and tripropylbismuthane are... B The values ​​are approximately 100℃ and 220℃. Experiments have confirmed that tetraalkyltinane, trialkylantimonane, and trialkylbismuthane organometallic molecules exhibit similar behavior. Experiments have also determined that the boiling point temperature T of organometallic molecules with propyl ligands is higher than that of organometallic molecules with methyl ligands. B An increase of at least approximately 120K.

[0339] Based on these observations, the melting point temperature T M When R is a C1 alkyl group, the predicted temperature is approximately 380 °C (e.g., trimethyl-λ). 5 - Bismuth ketone; 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxabi-λ 5 -bismuth tetracyclo; and 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth heterocyclic), when R is a C2 alkyl group, the predicted temperature is about 440 °C (e.g., triethyl-λ). 5 - Bismuth ketone; 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxabi-λ 5 -bismuth tetracyclo; and 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth heterocyclic), when R is a C3 alkyl group, the predicted temperature is about 500 °C (e.g., tripropyl-λ). 5 -bismuth ketone; tris(propan-2-yl)-λ 5 -Bismuth ketone; Tricyclopropyl-λ 5 - Bismuth ketone; 2,2,2,4,4,4-hexapropyl-1,3,2,4-dioxabi-λ 5 -Bis(2,2,2,4,4,4-hexanepropyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo; 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth heterocyclic; and 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth heterocyclic), and when R is a C4 alkyl group, the predicted temperature is about 560 °C (e.g., tributyl-λ). 5 -bismuth ketone; tris(tert-butyl)-λ 5 -Bismuth ketone; Tricyclobutyl-λ 5 - Bismuth ketone; 2,2,2,4,4,4-hexabutyl-1,3,2,4-dioxabi-λ5 -Bismuth tetracyclo; 2,2,2,4,4,4-hexanebutyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo; 2,2,2,4,4,4,6,6,6-nonadenylated-1,3,5,2,4,6-trioxatri-λ 5 -bismuth heterocyclic; and 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trioxatri-λ 5 -Bismuth heterocyclic rings).

[0340] Sulfide compounds typically have a similar (but slightly lower) melting point temperature T compared to their corresponding oxides. M For example, the melting point temperature T of Bi₂S₃ and Bi₂O₃ M These are approximately 775°C and 817°C, respectively. Therefore, it is reasonable to assume that the corresponding bismuth ketone used for dry photoresist or hard masks in EUV lithography, and λ... 5 - Bismuthyl ketone, bismuthylthione, λ 5 - Bismuthylthione, bismuthylimine, λ 5 -bismuthaneimine, 1,3,2,4-dioxabismutha tetracyclo, 1,3,2,4-dioxabismutha tetracyclo 5 -bismuth tetracyclic, 1,3,5,2,4,6-trioxatribismuth hexacyclic, 1,3,5,2,4,6-trioxatri-λ 5 -bismuth heterocyclic, 1,3,2,4-dithiabismuth heterocyclic, 1,3,2,4-dithiabis-λ 5 -bismuth tetracyclic, 1,3,5,2,4,6-trithiabismuth hexacyclic, 1,3,5,2,4,6-trithiatri-λ 5 -bismuth hexacyclic, 1,3,2,4-diazabismuth tetracyclic, 1,3,2,4-diazabis-λ 5 -bismuth tetracyclic, 1,3,5,2,4,6-triazatribismuth hexacyclic, and 1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic organometallic molecules have similar melting point temperatures T M .

[0341] In a preferred embodiment, the organometallic compound used for dry photoresist or hard masks in EUV lithography has a melting point of at least 100°C. In a more preferred embodiment, the organometallic compound has a melting point range of 300°C to 600°C. Such organometallic compounds are solids with very low vapor pressures under the vacuum conditions observed in EUV scanners. Therefore, from the perspective of diffusion coefficient, the alkyl ligands or R-groups in the organometallic compounds detailed above are preferably linear or branched C1 to C4 alkyl or cyclic C1 to C4 alkyl, more preferably linear or branched C2 to C4 alkyl or cyclic C3 or C4 alkyl.

[0342] Regarding bond dissociation (ii), (Bi-C), gas-phase simulations of the bond energies (uniform dissociation energies) of organobismuth (V) molecules from the beginning were performed at the Perdew-Burke-Esnzerof and double-valence polarization (PBE / DZVP) theoretical levels. These simulations provide a detailed understanding of the relative sensitivity expected for organometallic molecules used in dry photoresists or hard masks for EUV lithography. In the following general chemical formulas, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, cPr represents a cyclopropyl group, and cBu represents a cyclobutyl group.

[0343] Trimethyl-λ 5 - Bismuth ketone, triethyl-λ 5 -bismuth ketone, tripropyl-λ 5 -bismuth ketone, and tributyl-λ 5 -bismuth ketone ( Figure 4B Simulations of the bond energy of ) yielded:

[0344] Tris(propan-2-yl)-λ 5 -bismuth ketones and tris(tert-butyl)-λ 5 -bismuth ketone ( Figure 4D Simulations of the bond energy of ) yielded:

[0345] Because of their higher bond energy Figure 4B The compound shown may be superior to Figure 4D Those shown.

[0346] Cyclopropyl dimethyl-λ 5 -bismuth ketone, tricyclopropyl-λ 5 - Bismuth ketone, cyclobutyldimethyl-λ 5 -bismuth ketone, and tricyclobutyl-λ 5 -bismuth ketone ( Figure 5B Simulations of the bond energy of ) yielded:

[0347] Based on for Figure 4B The series λ shown in 4D and 5B 5 The immediately determined bond energy of the bismuthanethion molecule was found to be the same as that of the corresponding bismuthanethion molecule within the experimental uncertainty.

[0348] Having 4-membered rings ( Figure 8B and 9B ) or 6-membered ring ( Figure 10B and 11B Organometallic compounds used in dry photoresists or hard masks for EUV lithography, respectively possessing properties similar to... Figure 4B and 5B The corresponding "bismuth ketone" type molecules shown have similar Bi-alkyl bond energies.

[0349] Organometallic compounds with bond energies below 30 kcal / mol (e.g., Figure 4D The compounds shown may be relatively unstable. Therefore, organometallic compounds with bond energies greater than about 30 kcal / mol may be preferred in some embodiments.

[0350] In some embodiments, from a bond-dissociation perspective, the alkyl ligand or R group in the organometallic compounds detailed above is preferably 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) are less preferred.

[0351] Regarding reaction product (iii), during EUV exposure, the Bi-C and NC bonds in the organometallic molecule dissociate, and the inorganic Bi=O, Bi=S, Bi-O, Bi-S, Bi=N, and Bi-N clusters undergo cross-linking (these clusters are non-volatile) and pair with organic free radicals. For example, in the case of trimethyloxobismuthane, the decomposition chemical process can proceed as follows: n C3H9OBi (BiO) n + 3n / 2 C2H6. In the case of trimethyloxobismuthane, the methyl radical pairs to form ethane. In another example, in the case of tricyclobutyloxobismuthane, the decomposition chemical process can proceed as follows: n C 12 H 21 OBi (BiO) n + 3n / 2 C8H 14In the case of tricyclobutylbismuthoxane, cyclobutyl radicals pair up and react to form cyclobutylcyclobutane. Examples of organic products formed by pairing radical reactions are shown in some embodiments below:

[0352] When R is methyl (C1 alkyl), the product of the paired radical reaction is ethane (C2), and its ambient pressure, boiling point, and temperature T are... B The vapor pressure is approximately 4200 kPa at -89°C and room temperature. When R is ethyl (C2 alkyl), the product of the paired radical reaction is butane (C4), with an ambient pressure, boiling point, and temperature T. B The vapor pressure is approximately 220 kPa at -1°C and room temperature.

[0353] When R is propyl (C3 alkyl), the product of the paired radical reaction is hexane (C6), and its ambient pressure boiling point temperature T B The vapor pressure is approximately 20 kPa at 69 °C and room temperature. When R is isopropyl (C3 alkyl), the product of the paired radical reaction is 2,4-dimethylpentane (C6), and its ambient pressure, boiling point, and temperature T are... B The vapor pressure at 80°C and room temperature is approximately 10 kPa. When R is cyclopropyl (C3 alkyl), the product of the paired radical reaction is cyclopropylcyclopropane (C6), and its ambient pressure, boiling point, and temperature T are... B The vapor pressure is approximately 20 kPa at approximately 70°C and room temperature.

[0354] When R is butyl (C4 alkyl), the product of the paired radical reaction is octane (C8), and its ambient pressure, boiling point, and temperature T are... B The vapor pressure is approximately 2 kPa at 126 °C and room temperature. When R is isobutyl (C4 alkyl), the product of the paired radical reaction is 2,2,4,4-tetramethylpentane (C8), and its ambient pressure, boiling point, and temperature T are... B The vapor pressure is approximately 2 kPa at 122 °C and room temperature. When R is cyclobutyl (C4 alkyl), the product of the paired radical reaction is cyclobutylcyclobutane (C8), with an ambient pressure, boiling point, and temperature T. B The vapor pressure is approximately 2 kPa at approximately 130°C and room temperature.

[0355] EUV production 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 to C8 alkyl molecules and cyclic C6 to C8 alkyl molecules are volatile under the processing conditions in an EUV scanner. Thus, from the perspective of reaction products, the alkyl ligands or R groups in the organometallic compounds detailed above are preferably linear or branched C1 to C4 alkyl or cyclic C3 or C4 alkyl. More preferably, at least one alkyl ligand or R group is linear or branched C1 to C3 alkyl or cyclic C3 alkyl.

[0356] Regarding shrinkage (iv) during EUV exposure, numerical simulations of the molecular volume of organobismuth (V) molecules were performed to gain an understanding of the shrinkage of organometallic molecules used in EUV lithography dry photoresist or hard masks due to material volatilization during EUV exposure.

[0357] Trimethyl-λ 5 - Bismuth ketone, triethyl-λ 5 -bismuth ketone, tripropyl-λ 5 -bismuth ketone, and tributyl-λ 5 -bismuth ketone ( Figure 4B ), and tricyclopropyl-λ 5 - Bismuth ketone and tricyclobutyl-λ 5 -bismuth ketone ( Figure 5B The ratio of the Bi=O cluster volume to the organobismuth (V) molecule volume in the sample is shown below:

[0358] Trimethyl-λ 5 - Bismuthylthione, Triethyl-λ 5 -bismuthylthione, tripropyl-λ 5 -bismuthylthione, and tributyl-λ 5 -bismuthylthione ( Figure 4B ), and tricyclopropyl-λ 5 -bismuthylthione and tricyclobutyl-λ 5 -bismuthylthione ( Figure 5B The ratio of the Bi=S cluster volume to the organobismuth (V) molecule volume in the sample is shown below:

[0359] Hexaalkyl-1,3,2,4-dioxa-2-λ 5 -bismuth tetracyclo(m=2) and nonaalkyl-1,3,5,2,4,6-trioxatri-λ 5 The ratio of the volume of the Bi=O cluster to the volume of the organobismuth (V) molecule in a bismuth heterocyclic ring (m=3), within the experimental uncertainty, is compared with the corresponding trialkyl-λ5 -The bismuth ketone molecule is identical. Hexaalkyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclic (m=2) and nonaalkyl-1,3,5,2,4,6-trithiatri-λ 5 The ratio of the volume of the Bi=S cluster to the volume of the organobismuth (V) molecule in a bismuth heterocyclic ring (m=3), within the experimental uncertainty, is compared with the corresponding trialkyl-λ 5 -The bismuthylthion molecule is identical. Based on these ratios, from a contraction perspective, at least one alkyl ligand or R group in the organometallic compounds detailed above is preferably linear or branched C1 to C3 alkyl or cyclic C3 alkyl. More preferably, in some embodiments, the R group is C1 or C2 alkyl.

[0360] Due to the aforementioned properties / effects, organometallic compounds used for dry photoresists or hard masks in EUV lithography are preferably selected from methylbismuth ketone, ethylbismuth ketone, propylbismuth ketone, butylbismuth ketone, methylbismuthylthione, ethylbismuthylthione, propylbismuthylthione, butylbismuthylthione, Bi-methylbismuthylimine, Bi-ethylbismuthylimine, Bi-propylbismuthylimine, Bi-butylbismuthylimine, and trimethyl-λ. 5 - Bismuth ketone, triethyl-λ 5 -bismuth ketone, tripropyl-λ 5 -bismuth ketone, tributyl-λ 5 - Bismuth ketone, trimethyl-λ 5 - Bismuthylthione, Triethyl-λ 5 -bismuthylthione, tripropyl-λ 5 -bismuthylthione, tributyl-λ 5 -bismuthylthione, Bi,Bi,Bi-trimethyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-triethyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-tripropyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-tributyl-λ 5 -bismuthaneimine, propane-2-ylbismuthane ketone, tert-butylbismuthane ketone, propane-2-ylbismuthanethone, tert-butylbismuthanethone, Bi-propane-2-ylbismuthaneimine, Bi-tert-butylbismuthaneimine, tris(propane-2-yl)-λ 5 -bismuth ketone, tris(tert-butyl)-λ 5 -bismuth ketone, tris(propan-2-yl)-λ 5 -bismuthylthione, tris(tert-butyl)-λ 5 -bismuthylthione, Bi,Bi,Bi-tris(propane-2-yl)-λ 5 -bismuthaneimine, Bi,Bi,Bi-tris(tert-butyl)-λ 5-Bismuthaneimine, cyclopropylbismuthane, cyclobutylbismuthane, cyclopropylbismuthylthione, cyclobutylbismuthylthione, Bi-cyclopropylbismuthaneimine, Bi-cyclobutylbismuthaneimine, tricyclopropyl-λ 5 - Bismuth ketone, tricyclobutyl-λ 5 -bismuth ketone, tricyclopropyl-λ 5 -bismuthylthione, tricyclobutyl-λ 5 -bismuthylthione, Bi,Bi,Bi-tricyclopropyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-tricyclobutyl-λ 5 - Bismuthylimine, dimethylbismuthyloxy(dimethyl)bismuthane, bis(dimethylbismuthyloxy)(methyl)bismuthane, dimethylbismuthylthio(dimethyl)bismuthane, bis(dimethylbismuthylthio)(methyl)bismuthane, bis(dimethylbismuthyl)amine, dimethylbismuthylamino(methyl)bismuthyl(dimethylbismuthyl)amine, diethylbismuthyloxy(diethyl)bismuthane, bis(diethylbismuthyloxy)(ethyl)bismuthane, diethylbismuthylthio(diethyl)bismuthane, bis(diethylbismuthylthio)(ethyl)bismuthane, bis(diethylbismuthyl)amine, diethylbismuthylamino(ethyl)bismuthyl(diethylbismuthyl) Amine, dipropylbismuthalkoxy(dipropyl)bismuthane, bis(dipropylbismuthalkoxy)(propyl)bismuthane, dipropylbismuthylthioalkyl(dipropyl)bismuthane, bis(dipropylbismuthylthioalkyl)(propyl)bismuthane, bis(dipropylbismuthyl)amine, dipropylbismuthylamino(propyl)bismuthyl(dipropylbismuthyl)amine, dibutylbismuthalkoxy(dibutyl)bismuthane, bis(dibutylbismuthalkoxy)(butyl)bismuthane, dibutylbismuthylthioalkyl(dibutyl)bismuthane, bis(dibutylbismuthylthioalkyl)(butyl)bismuthane, bis(dibutylbismuthyl)amine, dibutylbismuthylamino(butyl)bismuthyl(dibutylbismuthyl, tetramethyl-λ) 5 -bismuthalkoxy(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthoxy)(trimethyl)-λ 5 -bismuthane, tetramethyl-λ 5 -bismuthylthioalkyl(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthylthio(trimethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthyl)amine, tetramethyl-λ 5 -bismuthylamino(trimethyl)-λ 5 -bismuthyl) (tetramethyl-λ 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthalkoxy(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ)5 -bismuthoxy)(triethyl)-λ 5 -bismuthane, tetraethyl-λ 5 -bismuthylthioalkyl(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthylthio(triethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthylamino(triethyl)-λ 5 -bismuthyl) (tetraethyl-λ) 5 -bismuthyl)amine, tetrapropyl-λ 5 -bismuthalkoxy(tetrapropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthoxy)(tripropyl)-λ 5 -bismuthane, tetrapropyl-λ 5 -bismuthylthioalkyl(tetrapropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthylthio(tripropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthyl)amine, tetrapropyl-λ 5 -bismuthalkylamino(tripropyl)-λ 5 -bismuthyl) (tetrapropyl-λ 5 -bismuthyl)amine, tetrabutyl-λ 5 -bismuthalkoxy(tetrabutyl)-λ 5 - Bismuthane, bis(tetrabutyl-λ) 5 -bismuthoxy)(tributyl)-λ 5 -bismuthane, tetrabutyl-λ 5 -bismuthylthioalkyl(tetrabutyl)-λ 5 - Bismuthane, bis(tetrabutyl-λ) 5 -bismuthylthioalkyl)(tributyl)-λ 5 - Bismuthane, bis(tetrabutyl-λ) 5 -bismuthyl)amine, tetrabutyl-λ 5 -bismuth alkylamino (tributyl)-λ 5 -bismuthyl) (tetrabutyl-λ) 5-bismuthyl)amine, dicyclopropylbismuthoxy(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthoxy)(cyclopropyl)bismuthane, dicyclopropylbismuthylthio(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthylthio)(cyclopropyl)bismuthane, bis(dicyclopropylbismuthyl)amine, dicyclopropylbismuthylamino(cyclopropyl)bismuthyl(dicyclopropylbismuthyl)amine, dicyclobutylbismuthoxy(dicyclobutyl)bismuthane, bis(dicyclobutylbismuthoxy)(cyclobutyl)bismuthane, dicyclobutylbismuthylthio(dicyclobutyl)bismuthane, bis(dicyclobutylbismuthylthio)(cyclobutyl)bismuthane, bis(dicyclobutylbismuthyl)amine, dicyclobutylbismuthylamino(cyclobutyl)bismuthyl(dicyclobutylbismuthyl)amine, tetracyclopropyl-λ 5 -bismuthalkoxy(tetracyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthoxy)(tricyclopropyl)-λ 5 -bismuthane, tetracyclopropyl-λ 5 -bismuthylthioalkyl(tetracyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthylthioalkyl)(tricyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthyl)amine, tetracyclopropyl-λ 5 -bismuthylamino(tricyclopropyl)-λ 5 -bismuthyl) (tetracyclopropyl-λ 5 -bismuthyl)amine, tetracyclobutyl-λ 5 -bismuthalkoxy(tetracyclobutyl)-λ 5 - Bismuthane, bis(tetracyclobutyl-λ) 5 -bismuthalkoxy)(tricyclobutyl)-λ 5 -bismuthane, tetracyclobutyl-λ 5 -bismuthylthioalkyl(tetracyclobutyl)-λ 5 - Bismuthane, bis(tetracyclobutyl-λ) 5 -bismuthylthioalkyl)(tricyclobutyl)-λ 5 - Bismuthane, bis(tetracyclobutyl-λ) 5 -bismuthyl)amine, tetracyclobutyl-λ 5 -bismuth alkylamino (tricyclobutyl)-λ 5 -bismuthyl) (tetracyclobutyl-λ) 5(-bismuthyl)amine, 2,4-dimethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-diethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dipropyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dibutyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dimethyl-1,3,2,4-dithiobismuth tetracyclic, 2,4-diethyl-1,3,2,4-dithiobismuth tetracyclic, 2,4-dipropyl-1,3 2,4-Dithiabismuth tetracyclic, 2,4-Dibutyl-1,3,2,4-Dithiabismuth tetracyclic, 2,4-Dimethyl-1,3,2,4-diazabismuth tetracyclic, 2,4-Diethyl-1,3,2,4-diazabismuth tetracyclic, 2,4-Dipropyl-1,3,2,4-diazabismuth tetracyclic, 2,4-Dibutyl-1,3,2,4-diazabismuth tetracyclic, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-dioxabis-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexabutyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexadecyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazabi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-diazabi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-diazabi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexadecyl-1,3,2,4-diazabi-λ 5-Bismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dicyclobutyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-dicyclobutyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-diazabismuth tetracyclic, 2,4-dicyclobutyl-1,3,2,4-diazabismuth tetracyclic, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dicyclobutyl-1,3,2,4-dioxabismuth tetracyclic, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-dioxabismuth tetracyclic 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexanebutyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexanebutyl-1,3,2,4-dithiadi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-diazabi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexanebutyl-1,3,2,4-diazabi-λ 5 -Bismuth tetracyclo, 2,4,6-trimethyl-1,3,5,2,4,6-trioxabismuth hexacyclo, 2,4,6-triethyl-1,3,5,2,4,6-trioxabismuth hexacyclo, 2,4,6-tripropyl-1,3,5,2,4,6-trioxabismuth hexacyclo, 2,4,6-tributyl-1,3,5,2,4,6-trioxabismuth hexacyclo, 2,4,6-trimethyl-1,3,5,2,4,6-trithiobismuth hexacyclo, 2,4,6-triethyl-1,3,5,2,4,6-trithiobismuth hexacyclo, 2,4,6-tripropyl-1,3,5,2,4,6-trithiobismuth hexacyclo, 2,4,6-tripropyl-1,3,5,2,4,6-trithiobismuth hexacyclo, 2,4,6-tripropyl-1,3,5,2,4,6-trithiobismuth hexacyclo 4,6-Trithiabismuth hexacyclic ring, 2,4,6-tributyl-1,3,5,2,4,6-trithiabismuth hexacyclic ring, 2,4,6-trimethyl-1,3,5,2,4,6-triazabismuth hexacyclic ring, 2,4,6-triethyl-1,3,5,2,4,6-triazabismuth hexacyclic ring, 2,4,6-tripropyl-1,3,5,2,4,6-triazabismuth hexacyclic ring, 2,4,6-tributyl-1,3,5,2,4,6-triazabismuth hexacyclic ring, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonadenylated-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonadenylated-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonadenylated-1,3,5,2,4,6-triazatri-λ 5 -Bismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trioxabismuth hexacyclic, 2,4,6-tricyclobutyl-1,3,5,2,4,6-trioxabismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trithiabismuth hexacyclic, 2,4,6-tricyclobutyl-1,3,5,2,4,6-trithiabismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-triazabismuth hexacyclic, 2,4,6-tricyclobutyl-1,3,5,2,4,6-triazabismuth hexacyclic, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trithiatri-λ 5-bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclohexane, and 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic rings.

[0361] In a still more preferred variation, the organometallic compound used for the dry photoresist or hard mask for EUV lithography can be selected from the following: methyl bismuthinone, ethyl bismuthinone, propyl bismuthinone, methyl bismuthylthionone, ethyl bismuthylthionone, propyl bismuthylthionone, Bi-methylbismuthylimine, Bi-ethyl bismuthylimine, Bi-propyl bismuthylimine, trimethyl-λ 5 - Bismuth ketone, triethyl-λ 5 -bismuth ketone, tripropyl-λ 5 - Bismuth ketone, trimethyl-λ 5 - Bismuthylthione, Triethyl-λ 5 -bismuthylthione, tripropyl-λ 5 -bismuthylthione, Bi,Bi,Bi-trimethyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-triethyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-tripropyl-λ 5 -Bismuthaneimine, cyclopropylbismuthane ketone, cyclopropylbismuthanethionone, Bi-cyclopropylbismuthaneimine, tricyclopropyl-λ 5 -bismuth ketone, tricyclopropyl-λ 5 -bismuthylthione, Bi,Bi,Bi-tricyclopropyl-λ 5 - Bismuthylimine, dimethylbismuthoxy(dimethyl)bismuthane, bis(dimethylbismuthoxy)(methyl)bismuthane, dimethylbismuthylthio(dimethyl)bismuthane, bis(dimethylbismuthylthio)(methyl)bismuthane, bis(dimethylbismuthyl)amine, dimethylbismuthylamino(methyl)bismuthyl(dimethylbismuthyl)amine, diethylbismuthoxy(diethyl)bismuthane, bis(diethylbismuthoxy)(ethyl)bismuthane, diethylbismuthylthio(diethyl)bismuthane, bis( Diethylbismuthylthioalkyl(ethyl)bismuthane, bis(diethylbismuthyl)amine, diethylbismuthylamino(ethyl)bismuthyl(diethylbismuthyl)amine, dipropylbismuthoxy(dipropyl)bismuthane, bis(dipropylbismuthoxy)(propyl)bismuthane, dipropylbismuthylthioalkyl(dipropyl)bismuthane, bis(dipropylbismuthylthioalkyl)(propyl)bismuthane, bis(dipropylbismuthyl)amine, dipropylbismuthylamino(propyl)bismuthyl(dipropylbismuthyl)amine, tetramethyl-λ 5 -bismuthalkoxy(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5-bismuthoxy)(trimethyl)-λ 5 -bismuthane, tetramethyl-λ 5 -bismuthylthioalkyl(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthylthio(trimethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthyl)amine, tetramethyl-λ 5 -bismuthylamino(trimethyl)-λ 5 -bismuthyl) (tetramethyl-λ 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthalkoxy(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthoxy)(triethyl)-λ 5 -bismuthane, tetraethyl-λ 5 -bismuthylthioalkyl(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthylthio(triethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthylamino(triethyl)-λ 5 -bismuthyl) (tetraethyl-λ) 5 -bismuthyl)amine, tetrapropyl-λ 5 -bismuthalkoxy(tetrapropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthoxy)(tripropyl)-λ 5 -bismuthane, tetrapropyl-λ 5 -bismuthylthioalkyl(tetrapropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthylthio(tripropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthyl)amine, tetrapropyl-λ 5 -bismuthalkylamino(tripropyl)-λ 5 -bismuthyl) (tetrapropyl-λ 5 -bismuthyl)amine, dicyclopropylbismuthoxy(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthoxy)(cyclopropyl)bismuthane, dicyclopropylbismuthylthio(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthylthio)(cyclopropyl)bismuthane, bis(dicyclopropylbismuthyl)amine, dicyclopropylbismuthylamino(cyclopropyl)bismuthyl(dicyclopropylbismuthyl)amine, tetracyclopropyl-λ 5 -bismuthalkoxy(tetracyclopropyl)-λ 5- Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthoxy)(tricyclopropyl)-λ 5 -bismuthane, tetracyclopropyl-λ 5 -bismuthylthioalkyl(tetracyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthylthioalkyl)(tricyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthyl)amine, tetracyclopropyl-λ 5 -bismuthylamino(tricyclopropyl)-λ 5 -bismuthyl) (tetracyclopropyl-λ 5 (bismuthyl)amine, 2,4-dimethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-diethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dipropyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dimethyl-1,3,2,4-dithiobismuth tetracyclic, 2,4-diethyl-1,3,2,4-dithiobismuth tetracyclic 2,4-Dipropyl-1,3,2,4-Dithiabismuth tetracyclo, 2,4-Dimethyl-1,3,2,4-diazabismuth tetracyclo, 2,4-Diethyl-1,3,2,4-diazabismuth tetracyclo, 2,4-Dipropyl-1,3,2,4-diazabismuth tetracyclo, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-dioxabis-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazabi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-diazabi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-diazabi-λ 5-bismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-dioxadibismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-diazabismuth tetracyclic, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-dithiadi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-diazabi-λ 5 -Bis(tetrazolium)cyclohexane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxabis(tetrazolium)cyclohexane, 2,4,6-triethyl-1,3,5,2,4,6-trioxabis(tetrazolium)cyclohexane, 2,4,6-tripropyl-1,3,5,2,4,6-trioxabis(tetrazolium)cyclohexane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiobis(tetrazolium)cyclohexane, 2,4,6-triethyl-1,3,5,2,4,6-trithiobis(tetrazolium)cyclohexane, 2 4,6-Tripropyl-1,3,5,2,4,6-Trithiabismuth-hexacyclohexane, 2,4,6-Trimethyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane, 2,4,6-Triethyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane, 2,4,6-Tripropyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-Nonmethyl-1,3,5,2,4,6-Trioxatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatri-λ 5-bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trioxabismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trithiabismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-triazabismuth hexacyclic, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclohexane, and 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic rings.

[0362] In the most preferred variation, the organometallic compound used for the dry photoresist or hard mask for EUV lithography can be selected from the following: methylbismuthinone, ethylbismuthinone, methylbismuthylthionone, ethylbismuthylthionone, Bi-methylbismuthylimine, Bi-ethylbismuthylimine, trimethyl-λ 5 - Bismuth ketone, triethyl-λ 5 - Bismuth ketone, trimethyl-λ 5 - Bismuthylthione, Triethyl-λ 5 -bismuthylthione, Bi,Bi,Bi-trimethyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-triethyl-λ 5 -Bismuthylimine, dimethylbismuthoxy(dimethyl)bismuthane, bis(dimethylbismuthoxy)(methyl)bismuthane, dimethylbismuthylthio(dimethyl)bismuthane, bis(dimethylbismuthylthio)(methyl)bismuthane, bis(dimethylbismuthyl)amine, dimethylbismuthylamino(methyl)bismuthyl(dimethylbismuthyl)amine, diethylbismuthoxy(diethyl)bismuthane, bis(diethylbismuthoxy)(ethyl)bismuthane, diethylbismuthylthio(diethyl)bismuthane, bis(diethylbismuthylthio)(ethyl)bismuthane, bis(diethylbismuthyl)amine, diethylbismuthylamino(ethyl)bismuthyl(diethylbismuthyl)amine, tetramethyl-λ 5 -bismuthalkoxy(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthoxy)(trimethyl)-λ 5 -bismuthane, tetramethyl-λ 5 -bismuthylthioalkyl(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5-bismuthylthio(trimethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthyl)amine, tetramethyl-λ 5 -bismuthylamino(trimethyl)-λ 5 -bismuthyl) (tetramethyl-λ 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthalkoxy(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthoxy)(triethyl)-λ 5 -bismuthane, tetraethyl-λ 5 -bismuthylthioalkyl(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthylthio(triethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthylamino(triethyl)-λ 5 -bismuthyl) (tetraethyl-λ) 5 (-bismuthyl)amine, 2,4-dimethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-diethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dimethyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-diethyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-dimethyl-1,3,2,4-diazabismuth tetracyclic, 2,4-diethyl-1,3,2,4-diazabismuth tetracyclic, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxabismuth tetracyclic 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazabi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-diazabi-λ 5-Bis(tetrazolium) ring, 2,4,6-trimethyl-1,3,5,2,4,6-trioxabis(tetrazolium) ring, 2,4,6-triethyl-1,3,5,2,4,6-trioxabis(tetrazolium) ring, 2,4,6-trimethyl-1,3,5,2,4,6-trithiabis(tetrazolium) ring, 2,4,6-triethyl-1,3,5,2,4,6-trithiabis(tetrazolium) ring, 2,4,6-trimethyl-1,3,5,2,4,6-triazabis(tetrazolium) ring, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxabis(tetrazolium) ring, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxabis(tetrazolium) ring 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclohexane, and 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic rings.

[0363] The synthesis of organometallic compounds for use in dry photoresists or hard masks for EUV lithography is described by way of example for trimethylbismuth trihydrogen oxide compounds. A benzene solution of trimethylbismuth 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 h. The benzene layer was separated by decantation, rotating on a molecular sieve for 12 h, and then filtered and concentrated by evaporation. Trimethylbismuth trihydrogen oxide (40%) was precipitated from the concentrated benzene solution by slow addition of petroleum ether.

[0364] Organometallic compounds used in 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 (diethylene glycol dimethyl ether), 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, ethoxyethyl propionate, etc.), and the like. Solvent systems comprising mixtures of two or more of the above solvents are also described in this application.

[0365] Embodiments of the present invention may include a dry photoresist or hard mask composition for EUV lithography, the composition comprising at least one organometallic compound described herein, and a dry photoresist or hard mask comprising the composition. In some embodiments, the disclosed organometallic compound is capable of undergoing a chemical transformation upon exposure of the dry photoresist or hard mask composition, particularly upon EUV irradiation, thereby creating a difference in the solubility of the dry photoresist or hard mask in exposed and unexposed areas.

[0366] In some embodiments, the content of the organometallic compound 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 solvents or solvent mixtures capable of dissolving the organometallic compound. Examples of such solvents include, but are not limited to, ethers, glycol ethers, aromatic hydrocarbons, ketones, esters, and the like (see above). Furthermore, the photoresist or hard mask composition for EUV lithography may also include 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 also be used if desired.

[0367] Figure 12 This is a flowchart illustrating a method 100 for forming patterned material features on a substrate using a dry photoresist or hard mask composition, according to some embodiments. Method 100 may include a photolithography process to produce patterned material layer structures such as metal wiring, holes or vias for contacts, insulating sections (e.g., grooved trenches or shallow trench isolators), trenches for capacitor structures, ion-implanted semiconductor structures for transistors, etc., as can be used in integrated circuit devices.

[0368] The material surface can be provided on the substrate. This is illustrated in Operation 110. The substrate can be any suitable substrate conventionally used in processes involving photoresist. For example, the substrate can be silicon, silicon oxide, aluminum, alumina, gallium arsenide, ceramic, quartz, copper, or any combination thereof, which may comprise multiple layers. Depending on the stage of the manufacturing process and the set of materials required for the final product, the material surface may include a metal conductor layer, a ceramic insulator layer, a semiconductor layer, or other materials.

[0369] A layer of the disclosed dry photoresist or hard mask composition can be formed on a material surface. This is illustrated in operation 120. The layer can be patterned by energy rays, thereby creating a layer of radiation-exposed regions in the dry photoresist or hard mask layer. This is illustrated in operation 130. In some embodiments, the energy rays used for patterning the photoresist composition are EUV rays. When exposed to EUV radiation, the organometallic compound can crosslink, thereby creating an insoluble network that remains on the substrate as a patterned material layer structure. A portion of the layer can then be selectively removed to form the exposed portion of the material surface. This is illustrated 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 include thermal processing steps, plasma ashing, plasma etching, etc.

[0370] In other embodiments, after exposure, the photoresist structure with the desired pattern can be obtained or developed by contacting the photoresist layer with an alkaline aqueous solution that selectively dissolves the exposed photoresist areas in the case of positive photoresist (or the unexposed areas in the case of negative photoresist). Some alkaline aqueous solutions or developers include aqueous solutions of tetramethylammonium hydroxide. The resulting photolithographic structure on the substrate is then dried to remove any remaining developer. If a topcoat is used, it can be dissolved by the developer in this step.

[0371] Method 100 may also include etching or ion-implanting exposed portions of the material, thereby forming patterned material features. This is illustrated in operation 150. The pattern from the photoresist structure is transferred to the exposed portions of the substrate's base material by etching with a suitable etchant using techniques known in the art. In some embodiments, the transfer is performed by reactive ion etching or by wet etching. Once the desired pattern transfer has occurred, any 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.

[0372] Although the invention has been described with reference to specific embodiments, it should be understood that the invention is not limited to these embodiments, and many variations of these embodiments can be readily conceived by those skilled in the art upon reading the disclosure of this invention. The invention can therefore be further described non-limitingly and by way of example only, with reference to the following embodiments. The following embodiments may include preferred embodiments. Therefore, the term "entry" as used in this invention may denote such a "preferred embodiment".

[0373] Item 1: An organometallic compound for use in dry photoresists or hard masks for EUV lithography, comprising: at least one Bi(III) or Bi(V) element; at least one terminal or bridging ligand A bonded to the Bi(III) or Bi(V) element, wherein ligand A is O, S or NR, and wherein the R group in NR is selected from H and C1 to C6 alkyl groups; and at least one C1 to C6 alkyl ligand bonded to the Bi(III) or Bi(V) element.

[0374] Item 2: The organometallic compound according to Item 1 has the general formula (I), (II), (III), (IV), (V), (VI), or (VII) as shown above, wherein A represents an element selected from O, S, and NR; R1, R2, R3, R4, R5, R6, R7, or R8 independently represent 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 heterocyclic alkyl; n is an integer from 1 to 4; m is an integer from 2 to 5; and R in NR represents H or 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 heterocyclic alkyl.

[0375] Item 3: Organometallic compounds according to Item 2, wherein n is an integer from 1 to 3 and m is an integer from 2 to 4.

[0376] Item 4: An organometallic compound according to any one of items 1 to 3, wherein the organometallic compound is composed of... Figure 3A Any one of the general formulas (a) to (o) shown represents, wherein R1, R2, R3, R4, R1 / 1, R1 / 2, R1 / 3, RN / 1, RN / 2, and RN / 3 independently represent, respectively, an unsubstituted or substituted linear or branched C1 to C6 alkyl group, an unsubstituted or substituted C3 to C6 cycloalkyl group, or an unsubstituted or substituted C3 to C6 heterocycloalkyl group; or wherein the organometallic compound is composed of Figure 3BAny one of the general formulas (p) to (ad) shown represents, wherein 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 represent, respectively, unsubstituted or substituted linear or branched C1 to C6 alkyl, unsubstituted or substituted C3 to C6 cycloalkyl, or unsubstituted or substituted C3 to C6 heterocycloalkyl.

[0377] Item 5: An organometallic compound according to any one of Items 2 to 4, wherein R1, R2, R3, R4, R5, R6, R7, and R8 of 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 of general formulas (a) to (ad) are unsubstituted or substituted linear or branched C1 to C5 alkyl groups, unsubstituted or substituted C3 to C5 cycloalkyl groups, or unsubstituted or substituted C3 to C5 heterocycloalkyl groups, particularly unsubstituted or substituted linear C1 to C5 alkyl groups.

[0378] Item 6: An organometallic compound according to any one of Items 2 to 5, wherein R1, R2, R3, R4, R5, R6, R7, and R8 of 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 of general formulas (a) to (ad) are unsubstituted or substituted linear or branched C1 to C4 alkyl, unsubstituted or substituted C3 or C4 cycloalkyl, or unsubstituted or substituted C3 or C4 heterocycloalkyl, particularly unsubstituted or substituted linear C1 to C4 alkyl.

[0379] Item 7: An organometallic compound according to any one of Items 2 to 6, wherein R1, R2, R3, R4, R5, R6, R7, and R8 of 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 of general formulas (a) to (ad) are unsubstituted or substituted linear or branched C1 to C3 alkyl groups, unsubstituted or substituted C3 cycloalkyl groups, or unsubstituted or substituted C3 heterocycloalkyl groups, particularly unsubstituted or substituted linear C1 to C3 alkyl groups.

[0380] Item 8: An organometallic compound according to any one of Items 2 to 7, wherein R1, R2, R3, R4, R5, R6, R7, and R8 of 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 of general formulas (a) to (ad) are unsubstituted or substituted C1 or C2 alkyl groups.

[0381] Item 9: An organometallic compound according to any one of Items 2 to 8, wherein R1, R2, R3, R4, R5, R6, R7, and R8 of 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 of general formulas (a) to (ad) are the same as or different from each other.

[0382] Item 10: An organometallic compound according to any one of items 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.

[0383] Item 11: An organometallic compound according to any one of items 1 to 10, wherein the dissociation energy of the organometallic compound is 30 kcal / mol.

[0384] Item 12: An organometallic compound according to any one of items 1 to 11, wherein the organometallic compound is selected from methylbismuth ketone, ethylbismuth ketone, propylbismuth ketone, butylbismuth ketone, methylbismuth thionone, ethylbismuth thionone, propylbismuth thionone, butylbismuth thionone, Bi-methylbismuth alkylimine, Bi-ethylbismuth alkylimine, Bi-propylbismuth alkylimine, Bi-butylbismuth alkylimine, trimethyl-λ 5 - Bismuth ketone, triethyl-λ 5 -bismuth ketone, tripropyl-λ 5 -bismuth ketone, tributyl-λ 5 - Bismuth ketone, trimethyl-λ 5 - Bismuthylthione, Triethyl-λ 5 -bismuthylthione, tripropyl-λ 5 -bismuthylthione, tributyl-λ 5 -bismuthylthione, Bi,Bi,Bi-trimethyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-triethyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-tripropyl-λ 5-bismuthaneimine, Bi,Bi,Bi-tributyl-λ 5 -bismuthaneimine, propane-2-ylbismuthane ketone, tert-butylbismuthane ketone, propane-2-ylbismuthanethone, tert-butylbismuthanethone, Bi-propane-2-ylbismuthaneimine, Bi-tert-butylbismuthaneimine, tris(propane-2-yl)-λ 5 -bismuth ketone, tris(tert-butyl)-λ 5 -bismuth ketone, tris(propan-2-yl)-λ 5 -bismuthylthione, tris(tert-butyl)-λ 5 -bismuthylthione, Bi,Bi,Bi-tris(propane-2-yl)-λ 5 -bismuthaneimine, Bi,Bi,Bi-tris(tert-butyl)-λ 5 -Bismuthaneimine, cyclopropylbismuthane, cyclobutylbismuthane, cyclopropylbismuthylthione, cyclobutylbismuthylthione, Bi-cyclopropylbismuthaneimine, Bi-cyclobutylbismuthaneimine, tricyclopropyl-λ 5 - Bismuth ketone, tricyclobutyl-λ 5 -bismuth ketone, tricyclopropyl-λ 5 -bismuthylthione, tricyclobutyl-λ 5 -bismuthylthione, Bi,Bi,Bi-tricyclopropyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-tricyclobutyl-λ 5 - Bismuthylimine, dimethylbismuthyloxy(dimethyl)bismuthane, bis(dimethylbismuthyloxy)(methyl)bismuthane, dimethylbismuthylthio(dimethyl)bismuthane, bis(dimethylbismuthylthio)(methyl)bismuthane, bis(dimethylbismuthyl)amine, dimethylbismuthylamino(methyl)bismuthyl(dimethylbismuthyl)amine, diethylbismuthyloxy(diethyl)bismuthane, bis(diethylbismuthyloxy)(ethyl)bismuthane, diethylbismuthylthio(diethyl)bismuthane, bis(diethylbismuthylthio)(ethyl)bismuthane, bis(diethylbismuthyl)amine, diethylbismuthylamino(ethyl)bismuthyl(diethylbismuthyl) Amine, dipropylbismuthalkoxy(dipropyl)bismuthane, bis(dipropylbismuthalkoxy)(propyl)bismuthane, dipropylbismuthylthioalkyl(dipropyl)bismuthane, bis(dipropylbismuthylthioalkyl)(propyl)bismuthane, bis(dipropylbismuthyl)amine, dipropylbismuthylamino(propyl)bismuthyl(dipropylbismuthyl)amine, dibutylbismuthalkoxy(dibutyl)bismuthane, bis(dibutylbismuthalkoxy)(butyl)bismuthane, dibutylbismuthylthioalkyl(dibutyl)bismuthane, bis(dibutylbismuthylthioalkyl)(butyl)bismuthane, bis(dibutylbismuthyl)amine, dibutylbismuthylamino(butyl)bismuthyl(dibutylbismuthyl, tetramethyl-λ) 5 -bismuthalkoxy(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthoxy)(trimethyl)-λ5 -bismuthane, tetramethyl-λ 5 -bismuthylthioalkyl(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthylthio(trimethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthyl)amine, tetramethyl-λ 5 -bismuthylamino(trimethyl)-λ 5 -bismuthyl) (tetramethyl-λ 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthalkoxy(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthoxy)(triethyl)-λ 5 -bismuthane, tetraethyl-λ 5 -bismuthylthioalkyl(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthylthio(triethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthylamino(triethyl)-λ 5 -bismuthyl) (tetraethyl-λ) 5 -bismuthyl)amine, tetrapropyl-λ 5 -bismuthalkoxy(tetrapropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthoxy)(tripropyl)-λ 5 -bismuthane, tetrapropyl-λ 5 -bismuthylthioalkyl(tetrapropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthylthio(tripropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthyl)amine, tetrapropyl-λ 5 -bismuthalkylamino(tripropyl)-λ 5 -bismuthyl) (tetrapropyl-λ 5 -bismuthyl)amine, tetrabutyl-λ 5 -bismuthalkoxy(tetrabutyl)-λ 5 - Bismuthane, bis(tetrabutyl-λ) 5 -bismuthoxy)(tributyl)-λ 5 -bismuthane, tetrabutyl-λ 5 -bismuthylthioalkyl(tetrabutyl)-λ 5 - Bismuthane, bis(tetrabutyl-λ) 5 -bismuthylthioalkyl)(tributyl)-λ5 - Bismuthane, bis(tetrabutyl-λ) 5 -bismuthyl)amine, tetrabutyl-λ 5 -bismuth alkylamino (tributyl)-λ 5 -bismuthyl) (tetrabutyl-λ) 5 -bismuthyl)amine, dicyclopropylbismuthoxy(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthoxy)(cyclopropyl)bismuthane, dicyclopropylbismuthylthio(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthylthio)(cyclopropyl)bismuthane, bis(dicyclopropylbismuthyl)amine, dicyclopropylbismuthylamino(cyclopropyl)bismuthyl(dicyclopropylbismuthyl)amine, dicyclobutylbismuthoxy(dicyclobutyl)bismuthane, bis(dicyclobutylbismuthoxy)(cyclobutyl)bismuthane, dicyclobutylbismuthylthio(dicyclobutyl)bismuthane, bis(dicyclobutylbismuthylthio)(cyclobutyl)bismuthane, bis(dicyclobutylbismuthyl)amine, dicyclobutylbismuthylamino(cyclobutyl)bismuthyl(dicyclobutylbismuthyl)amine, tetracyclopropyl-λ 5 -bismuthalkoxy(tetracyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthoxy)(tricyclopropyl)-λ 5 -bismuthane, tetracyclopropyl-λ 5 -bismuthylthioalkyl(tetracyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthylthioalkyl)(tricyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthyl)amine, tetracyclopropyl-λ 5 -bismuthylamino(tricyclopropyl)-λ 5 -bismuthyl) (tetracyclopropyl-λ 5 -bismuthyl)amine, tetracyclobutyl-λ 5 -bismuthalkoxy(tetracyclobutyl)-λ 5 - Bismuthane, bis(tetracyclobutyl-λ) 5 -bismuthalkoxy)(tricyclobutyl)-λ 5 -bismuthane, tetracyclobutyl-λ 5 -bismuthylthioalkyl(tetracyclobutyl)-λ 5 - Bismuthane, bis(tetracyclobutyl-λ) 5 -bismuthylthioalkyl)(tricyclobutyl)-λ 5 - Bismuthane, bis(tetracyclobutyl-λ) 5 -bismuthyl)amine, tetracyclobutyl-λ 5 -bismuth alkylamino (tricyclobutyl)-λ 5 -bismuthyl) (tetracyclobutyl-λ) 5(-bismuthyl)amine, 2,4-dimethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-diethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dipropyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dibutyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dimethyl-1,3,2,4-dithiobismuth tetracyclic, 2,4-diethyl-1,3,2,4-dithiobismuth tetracyclic, 2,4-dipropyl-1,3 2,4-Dithiabismuth tetracyclic, 2,4-Dibutyl-1,3,2,4-Dithiabismuth tetracyclic, 2,4-Dimethyl-1,3,2,4-diazabismuth tetracyclic, 2,4-Diethyl-1,3,2,4-diazabismuth tetracyclic, 2,4-Dipropyl-1,3,2,4-diazabismuth tetracyclic, 2,4-Dibutyl-1,3,2,4-diazabismuth tetracyclic, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-dioxabis-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexabutyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexadecyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazabi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-diazabi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-diazabi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexadecyl-1,3,2,4-diazabi-λ 5-Bismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dicyclobutyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-dicyclobutyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-diazabismuth tetracyclic, 2,4-dicyclobutyl-1,3,2,4-diazabismuth tetracyclic, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dicyclobutyl-1,3,2,4-dioxabismuth tetracyclic, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-dioxabismuth tetracyclic 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexanebutyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexanebutyl-1,3,2,4-dithiadi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-diazabi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexanebutyl-1,3,2,4-diazabi-λ 5 -Bismuth tetracyclo, 2,4,6-trimethyl-1,3,5,2,4,6-trioxabismuth hexacyclo, 2,4,6-triethyl-1,3,5,2,4,6-trioxabismuth hexacyclo, 2,4,6-tripropyl-1,3,5,2,4,6-trioxabismuth hexacyclo, 2,4,6-tributyl-1,3,5,2,4,6-trioxabismuth hexacyclo, 2,4,6-trimethyl-1,3,5,2,4,6-trithiobismuth hexacyclo, 2,4,6-triethyl-1,3,5,2,4,6-trithiobismuth hexacyclo, 2,4,6-tripropyl-1,3,5,2,4,6-trithiobismuth hexacyclo, 2,4,6-tripropyl-1,3,5,2,4,6-trithiobismuth hexacyclo, 2,4,6-tripropyl-1,3,5,2,4,6-trithiobismuth hexacyclo 4,6-Trithiabismuth hexacyclic ring, 2,4,6-tributyl-1,3,5,2,4,6-trithiabismuth hexacyclic ring, 2,4,6-trimethyl-1,3,5,2,4,6-triazabismuth hexacyclic ring, 2,4,6-triethyl-1,3,5,2,4,6-triazabismuth hexacyclic ring, 2,4,6-tripropyl-1,3,5,2,4,6-triazabismuth hexacyclic ring, 2,4,6-tributyl-1,3,5,2,4,6-triazabismuth hexacyclic ring, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonadenylated-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonadenylated-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonadenylated-1,3,5,2,4,6-triazatri-λ 5 -Bismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trioxabismuth hexacyclic, 2,4,6-tricyclobutyl-1,3,5,2,4,6-trioxabismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trithiabismuth hexacyclic, 2,4,6-tricyclobutyl-1,3,5,2,4,6-trithiabismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-triazabismuth hexacyclic, 2,4,6-tricyclobutyl-1,3,5,2,4,6-triazabismuth hexacyclic, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trithiatri-λ 5-bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclohexane, and 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic rings.

[0385] Item 13: The organometallic compound according to Item 12, wherein the organometallic compound is selected from methylbismuth ketone, ethylbismuth ketone, propylbismuth ketone, methylbismuthylthionone, ethylbismuthylthionone, propylbismuthylthionone, Bi-methylbismuthylimine, Bi-ethylbismuthylimine, Bi-propylbismuthylimine, trimethyl-λ 5 - Bismuth ketone, triethyl-λ 5 -bismuth ketone, tripropyl-λ 5 - Bismuth ketone, trimethyl-λ 5 - Bismuthylthione, Triethyl-λ 5 -bismuthylthione, tripropyl-λ 5 -bismuthylthione, Bi,Bi,Bi-trimethyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-triethyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-tripropyl-λ 5 -Bismuthaneimine, cyclopropylbismuthane ketone, cyclopropylbismuthanethionone, Bi-cyclopropylbismuthaneimine, tricyclopropyl-λ 5 -bismuth ketone, tricyclopropyl-λ 5 -bismuthylthione, Bi,Bi,Bi-tricyclopropyl-λ 5 - Bismuthylimine, dimethylbismuthoxy(dimethyl)bismuthane, bis(dimethylbismuthoxy)(methyl)bismuthane, dimethylbismuthylthio(dimethyl)bismuthane, bis(dimethylbismuthylthio)(methyl)bismuthane, bis(dimethylbismuthyl)amine, dimethylbismuthylamino(methyl)bismuthyl(dimethylbismuthyl)amine, diethylbismuthoxy(diethyl)bismuthane, bis(diethylbismuthoxy)(ethyl)bismuthane, diethylbismuthylthio(diethyl)bismuthane, bis( Diethylbismuthylthioalkyl(ethyl)bismuthane, bis(diethylbismuthyl)amine, diethylbismuthylamino(ethyl)bismuthyl(diethylbismuthyl)amine, dipropylbismuthoxy(dipropyl)bismuthane, bis(dipropylbismuthoxy)(propyl)bismuthane, dipropylbismuthylthioalkyl(dipropyl)bismuthane, bis(dipropylbismuthylthioalkyl)(propyl)bismuthane, bis(dipropylbismuthyl)amine, dipropylbismuthylamino(propyl)bismuthyl(dipropylbismuthyl)amine, tetramethyl-λ 5 -bismuthalkoxy(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthoxy)(trimethyl)-λ5 -bismuthane, tetramethyl-λ 5 -bismuthylthioalkyl(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthylthio(trimethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthyl)amine, tetramethyl-λ 5 -bismuthylamino(trimethyl)-λ 5 -bismuthyl) (tetramethyl-λ 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthalkoxy(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthoxy)(triethyl)-λ 5 -bismuthane, tetraethyl-λ 5 -bismuthylthioalkyl(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthylthio(triethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthylamino(triethyl)-λ 5 -bismuthyl) (tetraethyl-λ) 5 -bismuthyl)amine, tetrapropyl-λ 5 -bismuthalkoxy(tetrapropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthoxy)(tripropyl)-λ 5 -bismuthane, tetrapropyl-λ 5 -bismuthylthioalkyl(tetrapropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthylthio(tripropyl)-λ 5 - Bismuthane, bis(tetrapropyl-λ) 5 -bismuthyl)amine, tetrapropyl-λ 5 -bismuthalkylamino(tripropyl)-λ 5 -bismuthyl) (tetrapropyl-λ 5 -bismuthyl)amine, dicyclopropylbismuthoxy(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthoxy)(cyclopropyl)bismuthane, dicyclopropylbismuthylthio(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthylthio)(cyclopropyl)bismuthane, bis(dicyclopropylbismuthyl)amine, dicyclopropylbismuthylamino(cyclopropyl)bismuthyl(dicyclopropylbismuthyl)amine, tetracyclopropyl-λ 5 -bismuthalkoxy(tetracyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ)5 -bismuthoxy)(tricyclopropyl)-λ 5 -bismuthane, tetracyclopropyl-λ 5 -bismuthylthioalkyl(tetracyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthylthioalkyl)(tricyclopropyl)-λ 5 - Bismuthane, bis(tetracyclopropyl-λ) 5 -bismuthyl)amine, tetracyclopropyl-λ 5 -bismuthylamino(tricyclopropyl)-λ 5 -bismuthyl) (tetracyclopropyl-λ 5 (bismuthyl)amine, 2,4-dimethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-diethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dipropyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dimethyl-1,3,2,4-dithiobismuth tetracyclic, 2,4-diethyl-1,3,2,4-dithiobismuth tetracyclic 2,4-Dipropyl-1,3,2,4-Dithiabismuth tetracyclo, 2,4-Dimethyl-1,3,2,4-diazabismuth tetracyclo, 2,4-Diethyl-1,3,2,4-diazabismuth tetracyclo, 2,4-Dipropyl-1,3,2,4-diazabismuth tetracyclo, 2,2,2,4,4,4-Hexamethyl-1,3,2,4-dioxabis-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazabi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-diazabi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexapropyl-1,3,2,4-diazabi-λ 5-bismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-dioxadibismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-dicyclopropyl-1,3,2,4-diazabismuth tetracyclic, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-dithiadi-λ 5 -bismuthatetracyclo, 2,2,2,4,4,4-hexanepropyl-1,3,2,4-diazabi-λ 5 -Bis(tetrazolium)cyclohexane, 2,4,6-trimethyl-1,3,5,2,4,6-trioxabis(tetrazolium)cyclohexane, 2,4,6-triethyl-1,3,5,2,4,6-trioxabis(tetrazolium)cyclohexane, 2,4,6-tripropyl-1,3,5,2,4,6-trioxabis(tetrazolium)cyclohexane, 2,4,6-trimethyl-1,3,5,2,4,6-trithiobis(tetrazolium)cyclohexane, 2,4,6-triethyl-1,3,5,2,4,6-trithiobis(tetrazolium)cyclohexane, 2 4,6-Tripropyl-1,3,5,2,4,6-Trithiabismuth-hexacyclohexane, 2,4,6-Trimethyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane, 2,4,6-Triethyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane, 2,4,6-Tripropyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-Nonmethyl-1,3,5,2,4,6-Trioxatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatri-λ 5-bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonapropyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trioxabismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-trithiabismuth hexacyclic, 2,4,6-tricyclopropyl-1,3,5,2,4,6-triazabismuth hexacyclic, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth heterocyclic, 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclohexane, and 2,2,2,4,4,4,6,6,6-nonacyclopropyl-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic; and preferably selected from methylbismuthone, ethylbismuthone, methylbismuthylthionone, ethylbismuthylthionone, Bi-methylbismuthylimine, Bi-ethylbismuthylimine, trimethyl-λ 5 - Bismuth ketone, triethyl-λ 5 - Bismuth ketone, trimethyl-λ 5 - Bismuthylthione, Triethyl-λ 5 -bismuthylthione, Bi,Bi,Bi-trimethyl-λ 5 -bismuthaneimine, Bi,Bi,Bi-triethyl-λ 5 -Bismuthylimine, dimethylbismuthoxy(dimethyl)bismuthane, bis(dimethylbismuthoxy)(methyl)bismuthane, dimethylbismuthylthio(dimethyl)bismuthane, bis(dimethylbismuthylthio)(methyl)bismuthane, bis(dimethylbismuthyl)amine, dimethylbismuthylamino(methyl)bismuthyl(dimethylbismuthyl)amine, diethylbismuthoxy(diethyl)bismuthane, bis(diethylbismuthoxy)(ethyl)bismuthane, diethylbismuthylthio(diethyl)bismuthane, bis(diethylbismuthylthio)(ethyl)bismuthane, bis(diethylbismuthyl)amine, diethylbismuthylamino(ethyl)bismuthyl(diethylbismuthyl)amine, tetramethyl-λ 5 -bismuthalkoxy(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthoxy)(trimethyl)-λ 5 -bismuthane, tetramethyl-λ 5 -bismuthylthioalkyl(tetramethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthylthio(trimethyl)-λ 5 - Bismuthane, bis(tetramethyl-λ) 5 -bismuthyl)amine, tetramethyl-λ5 -bismuthylamino(trimethyl)-λ 5 -bismuthyl) (tetramethyl-λ 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthalkoxy(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthoxy)(triethyl)-λ 5 -bismuthane, tetraethyl-λ 5 -bismuthylthioalkyl(tetraethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthylthio(triethyl)-λ 5 - Bismuthane, bis(tetraethyl-λ) 5 -bismuthyl)amine, tetraethyl-λ 5 -bismuthylamino(triethyl)-λ 5 -bismuthyl) (tetraethyl-λ) 5 (-bismuthyl)amine, 2,4-dimethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-diethyl-1,3,2,4-dioxabismuth tetracyclic, 2,4-dimethyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-diethyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-dimethyl-1,3,2,4-diazabismuth tetracyclic, 2,4-diethyl-1,3,2,4-diazabismuth tetracyclic, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxabismuth tetracyclic 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dithiadi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazabi-λ 5 -bismuth tetracyclo, 2,2,2,4,4,4-hexaethyl-1,3,2,4-diazabi-λ 5-Bis(tetrazolium) ring, 2,4,6-trimethyl-1,3,5,2,4,6-trioxabis(tetrazolium) ring, 2,4,6-triethyl-1,3,5,2,4,6-trioxabis(tetrazolium) ring, 2,4,6-trimethyl-1,3,5,2,4,6-trithiabis(tetrazolium) ring, 2,4,6-triethyl-1,3,5,2,4,6-trithiabis(tetrazolium) ring, 2,4,6-trimethyl-1,3,5,2,4,6-triazabis(tetrazolium) ring, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxabis(tetrazolium) ring, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trioxabis(tetrazolium) ring 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclohexane, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatri-λ 5 -bismuth-hexacyclo, 2,2,2,4,4,4,6,6,6-nonamethyl-1,3,5,2,4,6-triazatri-λ 5 -bismuth-hexacyclohexane, and 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatri-λ 5 -Bismuth heterocyclic rings.

[0386] Item 14: Use of any organometallic compound according to any one of items 1 to 13 for the preparation of dry photoresist or hard mask compositions for EUV lithography.

[0387] Item 16: The dry photoresist or hard mask composition according to Item 15 contains 5 to 95% by weight of an organometallic compound, particularly 10 to 90% by weight, and more particularly 20 to 80% by weight, based on the total weight of the photoresist composition.

[0388] Item 17: The dry photoresist or hard mask composition according to Item 15 or 16 further comprises a solvent.

[0389] Item 18: A dry photoresist or hard mask composition according to any one of items 15 to 17.

[0390] Item 19: A method for forming patterned material features 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 Items 15 to 17 on the material surface; irradiating the dry photoresist or hard mask composition layer in a patterned manner with energy rays, thereby forming a pattern of radiation exposure regions 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 surface, thereby forming patterned material features.

[0391] Item 20: The method according to Item 19, wherein selective removal of a portion of the dry photoresist or hard mask layer is performed by a thermal process step, plasma ashing, or plasma etching process step.

Claims

1. Organic metal compound for dry photoresist or hard mask in EUV lithography, comprising: at least one bismuth element selected from Bi(III) and Bi(V); at least one terminal or bridging ligand A bonded to the bismuth element, wherein the A ligand is selected from O, S and N-R, and wherein the R group in N-R is selected from H and Ci to C6 alkyl; and at least one Ci to C6 alkyl ligand bonded to the bismuth element.

2. The organometallic compound according to claim 1, having a general formula selected from the group consisting of: General Formula (I), General Formula (II), General Formula (III), General Formula (IV), General Formula (V), General Formula (VI), and general formula (VII), wherein in general formula (I), (II), (III), (IV), (V), (VI), and (VII): A represents a substance selected from O, S and N-R; R1, R2, R3, R4, R5, R6, R7, and R8 represent an alkyl ligand selected from the group consisting of optionally substituted linear or branched Ci to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, and optionally substituted C3 to C6 heterocycloalkyl; n is an integer from 1 to 4; m is an integer from 2 to 5; and R in N-R represents a substance selected from the group consisting of H, optionally substituted linear Ci to C6 alkyl, optionally substituted branched Ci to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, and optionally substituted C3 to C6 heterocycloalkyl.

3. The organic metal 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 of claim 2, wherein the organometallic compound has a general formula selected from the group consisting of general formulas (a) to (ad): wherein: in general formula (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 Ci to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, and optionally substituted C3 to C6 heterocycloalkyl; and in general formula (p) 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 independently selected from the group consisting of optionally substituted linear or branched Ci to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, and optionally substituted C3 to C6 heterocycloalkyl.

5. The organic metal compound according to claim 4, wherein 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 formula (a) to (ad) are selected from the group consisting of optionally substituted linear Ci to C5 alkyl, optionally substituted branched Ci to C5 alkyl, optionally substituted C3 to C5 cycloalkyl, and optionally substituted C3 to C5 heterocycloalkyl.

6. The organometallic compound of claim 4, wherein 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 general formulae (a) to (ad) are selected from the group consisting of optionally substituted linear C1 to C4 alkyl, optionally substituted branched C1 to C4 alkyl, optionally substituted C3 or C4 cycloalkyl, and optionally substituted C3 or C4 heterocycloalkyl.

7. The organometallic compound of claim 4, wherein 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 general formulae (a) to (ad) are selected from the group consisting of optionally substituted linear C1 to C3 alkyl, optionally substituted branched C1 to C3 alkyl, optionally substituted C3 cycloalkyl, and optionally substituted C3 heterocycloalkyl.

8. The organometallic compound of claim 4, wherein 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 general formulae (a) to (ad) are selected from the group consisting of optionally substituted C1 alkyl and optionally substituted C2 alkyl.

9. The organometallic compound of claim 4, wherein 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 general formulae (a) to (ad) are identical to each other.

10. The organometallic compound of claim 1, wherein the organometallic compound has a melting point of 100 °C.

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

12. The organometallic compound of claim 1, wherein the organometallic compound has a dissociation energy of at least 30 kcal / mol.

13. The organometallic compound of claim 1, wherein the organometallic compound is selected from the group consisting of methylbismuthane ketone, ethylbismuthane ketone, propylbismuthane ketone, butylbismuthane ketone, methylbismuthane thione, ethylbismuthane thione, propylbismuthane thione, butylbismuthane thione, Bi-methylbismuthane imine, Bi-ethylbismuthane imine, Bi-propylbismuthane imine, Bi-butylbismuthane imine, propyl-2-bismuthane ketone, tert-butylbismuthane ketone, propyl-2-bismuthane thione, tert-butylbismuthane thione, Bi-propyl-2-bismuthane imine, Bi-tert-butylbismuthane imine, cyclopropylbismuthane ketone, cyclobutylbismuthane ketone, cyclopropylbismuthane thione, cyclobutylbismuthane thione, Bi-cyclopropylbismuthane imine, Bi-cyclobutylbismuthane imine, ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ trimethyl-λ 5 - bithionol, triethyl-λ 5 - bithionol, tripropyl-λ 5 - bithionol, tributyl-λ 5 - bismuthyl ketone, trimethyl-λ 5 - bismuthyl thione, triethyl-λ 5 - bismuthyl thione, tripropyl-λ 5 - bismuthyl thione, tributyl-λ 5 - bismuthyl thione, Bi, Bi, Bi -trimethyl-λ 5 - bismuth alkyl imines, Bi, Bi, Bi -triethyl- lambda 5 - bismuth alkyl imines, Bi, Bi, Bi - tripropyl- lambda 5 - bismuth alkyl imines, Bi, Bi, Bi - tributyl- lambda 5 - bismuth alkyl imines, ​ ​ ​ ​ ​ ​ Tris(propane-2-yl)-lambda 5 - bithianol, Tris(tert-butyl)-lambda 5 - bithionol, Tris(propane-2-yl)-lambda 5 - bismuthane thione, Tris(tert-butyl)-lambda 5 - bismuthylthioketone, Bi, Bi, Bi - Tris(propane-2-yl)-lambda 5 - bismuth alkyl imines, Bi, Bi, Bi - tri-tert-butyl- lambda 5 - bismuth alkyl imines, ​ ​ ​ ​ ​ ​ tricyclopropyl-λ 5 - bithionol, tricyclo[5.2.1.02'6]decyl-λ 5 - bismuthyl ketone, tricyclopropyl-λ 5 - bismuthyl thione, tricyclo[5.2.1.02'6]decyl-λ 5 - bismuthylthione, Bi, Bi, Bi - Tricyclopropyl- lambda 5 - bismuth alkyl imines, Bi, Bi, Bi - Tricyclohexyl- lambda 5 - bismuth alkyl imines, Dimethylbismuthoxy(dimethyl)bismuthane, bis(dimethylbismuthoxy)(methyl)bismuthane, Dimethylbismuthylthio(dimethyl)bismuthane, bis(dimethylbismuthylthio)(methyl)bismuthane, bis(dimethylbismuthyl)amine, Dimethylbismuthylamino(methyl)bismuthyl(dimethylbismuthyl)amine, Diethylbismuthoxy(diethyl)bismuthane, bis(diethylbismuthoxy)(ethyl)bismuthane, Diethylbismuthylthioalkyl(diethyl)bismuthane, bis(diethylbismuthylthio)(ethyl)bismuthane, bis(diethylbismuthyl)amine, Diethylbismuthylamino(ethyl)bismuthyl(diethylbismuthyl)amine, Dipropylbismuthoxy(dipropyl)bismuthane, bis(dipropylbismuthoxy)(propyl)bismuthane, Dipropylbismuthylthioalkyl(dipropyl)bismuthane, bis(dipropylbismuthylthio)(propyl)bismuthane, bis(dipropylbismuthyl)amine, Dipropylbismuthylamino(propyl)bismuthyl(dipropylbismuthyl)amine, Dibutylbismuthoxy(dibutyl)bismuthane, bis(dibutylbismuthoxy)(butyl)bismuthane, Dibutylbismuthylthioalkyl(dibutyl)bismuthane, bis(dibutylbismuthylthio)(butyl)bismuthane, bis(dibutylbismuthyl)amine, Dibutylbismuthylamino(butyl)bismuthyl (dibutylbismuthyl) tetramethyl-λ 5 - bismuth alkoxyl (tetramethyl)-λ 5 - bismuth alkyl, bis(tetramethyl-λ 5 - bismuth alkoxyl) (trimethyl)-λ 5 - bismuth alkyl, tetramethyl-λ 5 - bismuth alkylsulfanyl group (tetramethyl)-λ 5 - bismuth alkyl, bis(tetramethyl-λ 5 - bismuth alkylsulfanyl groups) (trimethyl)-λ 5 - bismuth alkyls, bis(tetramethyl-λ 5 - bismuth alkyl) amines, tetramethyl-λ 5 - bismuth alkylamino (trimethyl)-λ 5 - bismuth alkyl) (tetramethyl-λ 5 - bismuth alkyl) amine, tetraethyl-λ 5 - bismuth alkoxide (tetraethyl)-λ 5 - bismuth alkyl, bis(tetraethyl-λ 5 - bismuth alkoxyl) (triethyl)-λ 5 - bismuth alkyl, tetraethyl-λ 5 - bismuth alkylsulfanylalkyl (tetraethyl)-λ 5 - bismuth alkyls bis(tetraethyl-λ 5 - bismuth alkylsulfanyl group) (triethyl)-λ 5 - bismuth alkyl, bis(tetraethyl-λ 5 - bismuth alkyl) amines, tetraethyl-λ 5 - bismuth alkylamino(triethyl)-λ 5 - bismuth alkyl)(tetraethyl-λ 5 - bismuth alkyl)amine, tetrapropyl-λ 5 - bismuth alkoxyl (tetrapropyl)-λ 5 - bismuth alkyl, bis(tetrapropyl-λ 5 - bismuth alkoxyl (tripropyl)-λ 5 - bismuth alkyl, tetrapropyl-λ 5 - bismuth alkylsulfanyl group (tetrapropyl)-λ 5 - bismuth alkyl, bis(tetrapropyl-λ 5 - bismuth alkylsulfanyl group) (tripropyl)-λ 5 - bismuth alkyl, bis(tetrapropyl-λ 5 - bismuth alkyl) amines, tetraalkyl-λ 5 - bismuth alkylamino (tripropyl-λ 5 - bismuth alkyl) (tetrapropyl-λ 5 - bismuth alkyl) amine, tetrabutyl-λ 5 - bismuth alkoxide (tetrabutyl)-λ 5 - bismuth alkyl, bis(tetrabutyl- lambda 5 - bismuth alkoxyl) (tributyl) - lambda 5 - bismuth alkyl, tetrabutyl-λ 5 - bismuth alkylsulfanyl group (tetrabutyl)-λ 5 - bismuth alkyl, bis(tetrabutyl- lambda 5 - bismuth alkylsulfanyl group) (tributyl) - lambda 5 - bismuth alkyl, bis(tetrabutyl-λ 5 - bismuth alkyl) amines, tetrabutyl-λ 5 - bismuth alkylamino (tributyl)-λ 5 - bismuth alkyl) (tetrabutyl-λ 5 - bismuth alkyl) amine, Dicyclopropylbismuthalkoxy(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthalkoxy)(cyclopropyl)bismuthane, Dicyclopropylbismuthylthioalkyl(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthylthioalkyl)(cyclopropyl)bismuthane, bis(dicyclopropylbismuthyl)amine, Dicyclopropylbismuthylamino(cyclopropyl)bismuthyl(dicyclopropylbismuthyl)amine, Dicyclobutylbismuthoxy(dicyclobutyl)bismuthane, bis(dicyclobutylbismuthoxy)(cyclobutyl)bismuthane, Dicyclobutylbismuthylthioalkyl(dicyclobutyl)bismuthane, bis(dicyclobutylbismuthylthioalkyl)(cyclobutyl)bismuthane, bis(dicyclobutylbismuthyl)amine, Dicyclobutylbismuthylamino(cyclobutyl)bismuthyl(dicyclobutylbismuthyl)amine, tetrahydropyran-3-yl 5 - bismethoxy (tetrahydropyran-3-yl)- 5 - bismethoxy, bis(tetrahydropyranyl-λ 5 - bismuth alkoxyl (tricyclopropyl)-λ 5 - bismuth alkyl, tetra- cyclopropyl-λ 5 - bismuth alkylsulfanylalkyl (tetra- cyclopropyl-λ 5 - bismuth alkylsulfanylalkyl (tetra- cyclopropyl-λ bis(tetrahydropyran-2-yl-λ 5 - bismuth alkylsulfanylalkyl) (tricyclopropyl-λ 5 - bismuth alkylsulfanylalkyl, bis(tetrahydropyranyl-λ 5 - bismuth alkyl) amines, tetra- cyclopropyl-λ 5 - bismuth alkylamino (tricyclopropyl-λ 5 - bismuth alkyl) (tetra- cyclopropyl-λ 5 - bismuth alkyl) amine, Tetracyclobutyl-λ 5 -bismuthalkoxy(tetracyclobutyl)-λ 5 - Bismuthane, bis(tetracyclo-λ 5 - bismuth alkoxyl) (tricyclo-λ 5 - bismuth alkyl, Tetracyclobutyl-λ 5 -bismuthylthioalkyl(tetracyclobutyl)-λ 5 - Bismuthane, bis(tetracyclo-λ 5 - bismuth alkylsulfanyl(tricyclo-λ 5 - bismuth alkylsulfanyl, bis(tetracycloalkyl-λ 5 - bismuth alkyl) amines, Tetracyclo[6.2.1.13,6.16]undec-4-yl-λ 5 Bismuth alkylamino(tetracyclo[6.2.1.13,6.16]undec-4-yl-λ 5 Bismuth alkyl)(tetracyclo[6.2.1.13,6.16]undec-4-yl-λ 5 Bismuth alkyl)amine, 2,4-Dimethyl-1,3,2,4-dioxabismuth tetracyclo 2,4-Diethyl-1,3,2,4-dioxabismuth tetracyclo 2,4-Dipropyl-1,3,2,4-Dioxabismutha tetracyclo, 2,4-Dibutyl-1,3,2,4-dioxabismuth tetracyclo 2,4-Dimethyl-1,3,2,4-dithiabismuth tetracyclohexane 2,4-Diethyl-1,3,2,4-dithiabismuth tetracyclohexane 2,4-Dipropyl-1,3,2,4-Dithiabismutha tetracyclohexane, 2,4-Dibutyl-1,3,2,4-dithiabismuth tetracyclic, 2,4-Dimethyl-1,3,2,4-diazabismuth tetracyclo 2,4-Diethyl-1,3,2,4-diazabismuth tetracyclo 2,4-Dipropyl-1,3,2,4-diazabismuth heterocyclic, 2,4-Dibutyl-1,3,2,4-diazabismuth heterocyclic, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxadino-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadisilolane 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dioxadino-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexabutyl-1,3,2,4-dioxadino-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithia-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dithia-λ 5 - bismuth heterotetracyclic, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dithia-λ 5 - bismuth heterotetracyclic, 2,2,2,4,4,4-hexabutyldisilazane 5 - bismuth heterotetracyclic, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexaethyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexapropyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexabutyld-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,4-Dicyclopropyl-1,3,2,4-dioxabismuth tetracyclo, 2,4-Dicyclobutyl-1,3,2,4-dioxabismuth tetracyclo 2,4-Dicyclopropyl-1,3,2,4-Dithiabismutha tetracyclo, 2,4-Dicyclobutyl-1,3,2,4-dithiabismuth tetracyclo 2,4-Dicyclopropyl-1,3,2,4-diazabismuth heterotetracyclo 2,4-Dicyclobutyl-1,3,2,4-diazabismuth heterotetracyclo 2,2,2,4,4,4-hexacyclopropyl-1,3,2,4-dioxadis-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexacyclobutyl-1,3,2,4-dioxadino-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexacyclopropyl-1,3,2,4-dithiadia-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexacyclobutyl-1,3,2,4-dithia-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexacyclopropyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexacyclobutyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,4,6-Trimethyl-1,3,5,2,4,6-trioxabismuth-hexacyclohexane, 2,4,6-Triethyl-1,3,5,2,4,6-Trioxane-bismuth-hexacyclohexane, 2,4,6-Tripropyl-1,3,5,2,4,6-Trioxane-bismuth-hexacyclohexane 2,4,6-Tributyl-1,3,5,2,4,6-Trioxanebismuth-hexacyclo ... 2,4,6-Trimethyl-1,3,5,2,4,6-trithiabismuth-hexacyclo ... 2,4,6-Triethyl-1,3,5,2,4,6-Trithiabismuth-hexacyclohexane, 2,4,6-Tripropyl-1,3,5,2,4,6-Trithiabismuth-hexacyclo ... 2,4,6-Tributyl-1,3,5,2,4,6-Trithiabismuth-hexacyclo ... 2,4,6-Trimethyl-1,3,5,2,4,6-triazabismuth-hexacyclohexane 2,4,6-Triethyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane 2,4,6-Tripropyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane 2,4,6-Tributyl-1,3,5,2,4,6-Triazabismuth-hexacyclo ... 2,2,2,4,4,4,6,6,6-nona-methyl-1,3,5,2,4,6-trioxatris-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatris-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona-propyl-1,3,5,2,4,6-trioxa-tri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona- butyl-1,3,5,2,4,6-trioxatris-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona-methyl-1,3,5,2,4,6-trithia-tri-silolane 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatricyclo-λ 5 - bismuth heterohexacyclic, 2,2,2,4,4,4,6,6,6-nona-propyl-1,3,5,2,4,6-trithia-tri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona- butyl-1,3,5,2,4,6-trithiatri- lambda 5 - bismuth heterohexacyclic, 2,2,2,4,4,4,6,6,6-nona-methyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona-propyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona- butyl-1,3,5,2,4,6-triazatri- lambda 5 - bismuth hetero hexacyclic, 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Trioxanetribismuthhexacyclohexacyclo, 2,4,6-Tricyclobutyl-1,3,5,2,4,6-trioxabismuth-hexacyclohexacyclo 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Trithiabismuth-hexacyclo ... 2,4,6-Tricyclobutyl-1,3,5,2,4,6-Trithiabismuth-hexacyclo ... 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexacyclo 2,4,6-Tricyclobutyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexacyclo 2,2,2,4,4,4,6,6,6-nona-cyclopropyl-1,3,5,2,4,6-trioxa-tri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trioxatris-λ 5 - bismuth heterohexacyclic, 2,2,2,4,4,4,6,6,6-nona-cyclopropyl-1,3,5,2,4,6-trithia- tri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-trithia-λ 5 - bismuth heterohexacyclic, 2,2,2,4,4,4,6,6,6-nona-cyclopropyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacyclic, and 2,2,2,4,4,4,6,6,6-nonacyclobutyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacyclic.

14. The organometallic compound according to claim 13, wherein the organometallic compound is selected from... Methylbismuth ketone, Ethylbismuth ketone, Propylbismuth ketone, Methylbismuthylthione, Ethylbismuthylthione, Propylbismuthylthione, Bi-methylbismuth alkylimine, Bi-ethylbismuth alkylimine, Bi-propylbismuth alkylimine, trimethyl-λ 5 - bithionol, triethyl-λ 5 - bithionol, tripropyl-λ 5 - bithionol, trimethyl-λ 5 - bismuthyl thione, triethyl-λ 5 - bismuthyl thione, tripropyl-λ 5 - bismuthyl thione, Bi, Bi, Bi -trimethyl-λ 5 - bismuth alkyl imines, Bi, Bi, Bi -triethyl- lambda 5 - bismuth alkyl imines, Bi, Bi, Bi - tripropyl- lambda 5 - bismuth alkylamines, Cyclopropyl bismuth ketone, Cyclopropyl bismuthylthione, Bi-cyclopropylbismuthylimine, tricyclopropyl-λ 5 - bithionol, tricyclopropyl-λ 5 - bismuthylthione, Bi, Bi, Bi - Tricyclopropyl- lambda 5 - bismuth alkyl imines, Dimethylbismuthoxy(dimethyl)bismuthane, bis(dimethylbismuthoxy)(methyl)bismuthane, Dimethylbismuthylthio(dimethyl)bismuthane, bis(dimethylbismuthylthio)(methyl)bismuthane, bis(dimethylbismuthyl)amine, Dimethylbismuthylamino(methyl)bismuthyl(dimethylbismuthyl)amine, Diethylbismuthoxy(diethyl)bismuthane, bis(diethylbismuthoxy)(ethyl)bismuthane, Diethylbismuthylthioalkyl(diethyl)bismuthane, bis(diethylbismuthylthio)(ethyl)bismuthane, bis(diethylbismuthyl)amine, Diethylbismuthylamino(ethyl)bismuthyl(diethylbismuthyl)amine, Dipropylbismuthoxy(dipropyl)bismuthane, bis(dipropylbismuthoxy)(propyl)bismuthane, Dipropylbismuthylthioalkyl(dipropyl)bismuthane, bis(dipropylbismuthylthio)(propyl)bismuthane, bis(dipropylbismuthyl)amine, Dipropylbismuthylamino(propyl)bismuthyl(dipropylbismuthyl)amine, tetramethyl-λ 5 - bismuth alkoxyl (tetramethyl)-λ 5 - bismuth alkyl, bis(tetramethyl-λ 5 - bismuth alkoxyl) (trimethyl)-λ 5 - bismuth alkyl, tetramethyl-λ 5 - bismuth alkylsulfanyl group (tetramethyl)-λ 5 - bismuth alkyl, bis(tetramethyl-λ 5 - bismuth alkylsulfanyl groups) (trimethyl)-λ 5 - bismuth alkyls, bis(tetramethyl-λ 5 - bismuth alkyl) amines, tetramethyl-λ 5 - bismuth alkylamino (trimethyl)-λ 5 - bismuth alkyl) (tetramethyl-λ 5 - bismuth alkyl) amine, tetraethyl-λ 5 - bismuth alkoxyl (tetraethyl)-λ 5 - bismuth alkyl, bis(tetraethyl-λ 5 - bismuth alkoxyl) (triethyl)-λ 5 - bismuth alkyl, tetraethyl-λ 5 - bismuth alkylsulfanylalkyl (tetraethyl)-λ 5 - bismuth alkyls bis(tetraethyl-λ 5 - bismuth alkylsulfanyl group) (triethyl)-λ 5 - bismuth alkyl, bis(tetraethyl-λ 5 - bismuth alkyl) amines, tetraethyl-λ 5 - bismuth alkylamino(triethyl)-λ 5 - bismuth alkyl)(tetraethyl-λ 5 - bismuth alkyl)amine, tetrapropyl-λ 5 - bismuth alkoxyl (tetrapropyl)-λ 5 - bismuth alkyl, bis(tetrapropyl-λ 5 - bismuth alkoxyl (tripropyl)-λ 5 - bismuth alkyl, tetrapropyl-λ 5 - bismuth alkylsulfanyl group (tetrapropyl)-λ 5 - bismuth alkyl, bis(tetrapropyl-λ 5 - bismuth alkylsulfanyl group) (tripropyl)-λ 5 - bismuth alkyl, bis(tetrapropyl-λ 5 - bismuth alkyl) amines, tetraalkyl-λ 5 - bismuth alkylamino (tripropyl-λ 5 - bismuth alkyl) (tetrapropyl-λ 5 - bismuth alkyl) amine, Dicyclopropylbismuthalkoxy(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthalkoxy)(cyclopropyl)bismuthane, Dicyclopropylbismuthylthioalkyl(dicyclopropyl)bismuthane, bis(dicyclopropylbismuthylthioalkyl)(cyclopropyl)bismuthane, bis(dicyclopropylbismuthyl)amine, Dicyclopropylbismuthylamino(cyclopropyl)bismuthyl(dicyclopropylbismuthyl)amine, tetrahydropyran-3-yl 5 - bismethoxy (tetrahydropyran-3-yl)- 5 - bismethoxy, bis(tetrahydropyran-3-yl-λ 5 - bismuth alkoxyl) (tricyclopropyl)-λ 5 - bismuth alkane, tetrahydropyran-2-yl 5 - bismuth alkylsulfanylalkyl (tetrahydropyran-2-yl)-λ 5 - bismuth alkylsulfanylalkyl (tetrahydropyran-2-yl)-λ bis(tetrahydropyran-2-yl-λ 5 - bismuth alkylsulfanylalkyl) (tricyclopropyl-λ 5 - bismuth alkylsulfanylalkyl, bis(tetrahydropyranyl-λ 5 - bismuth alkyl) amines, tetra- isopropyl-λ 5 - bismuth alkylamino (tetra- isopropyl-λ 5 - bismuth alkyl) (tetra- isopropyl-λ 5 - bismuth alkyl) amine, 2,4-Dimethyl-1,3,2,4-dioxabismuth tetracyclo 2,4-Diethyl-1,3,2,4-dioxabismuth tetracyclo 2,4-Dipropyl-1,3,2,4-Dioxabismutha tetracyclo, 2,4-Dimethyl-1,3,2,4-dithiabismuth tetracyclohexane 2,4-Diethyl-1,3,2,4-dithiabismuth tetracyclohexane 2,4-Dipropyl-1,3,2,4-Dithiabismutha tetracyclohexane, 2,4-Dimethyl-1,3,2,4-diazabismuth tetracyclo 2,4-Diethyl-1,3,2,4-diazabismuth tetracyclo 2,4-Dipropyl-1,3,2,4-diazabismuth heterocyclic, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxadino-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadisilolane 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dioxadino-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithia-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dithia-λ 5 - bismuth heterotetracyclic, 2,2,2,4,4,4-hexapropyl-1,3,2,4-dithia-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexaethyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexapropyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,4-Dicyclopropyl-1,3,2,4-dioxabismuth tetracyclo, 2,4-Dicyclopropyl-1,3,2,4-Dithiabismutha tetracyclo, 2,4-Dicyclopropyl-1,3,2,4-diazabismuth heterotetracyclo 2,2,2,4,4,4-hexacyclopropyl-1,3,2,4-dioxadis-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexacyclopropyl-1,3,2,4-dithiadia-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexacyclopropyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,4,6-Trimethyl-1,3,5,2,4,6-trioxabismuth-hexacyclohexane, 2,4,6-Triethyl-1,3,5,2,4,6-Trioxane-bismuth-hexacyclohexane, 2,4,6-Tripropyl-1,3,5,2,4,6-Trioxane-bismuth-hexacyclohexane 2,4,6-Trimethyl-1,3,5,2,4,6-trithiabismuth-hexacyclo ... 2,4,6-Triethyl-1,3,5,2,4,6-Trithiabismuth-hexacyclohexane, 2,4,6-Tripropyl-1,3,5,2,4,6-Trithiabismuth-hexacyclo ... 2,4,6-Trimethyl-1,3,5,2,4,6-triazabismuth-hexacyclohexane 2,4,6-Triethyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane 2,4,6-Tripropyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane 2,2,2,4,4,4,6,6,6-nona-methyl-1,3,5,2,4,6-trioxatris-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatris-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona-propyl-1,3,5,2,4,6-trioxa-tri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona-methyl-1,3,5,2,4,6-trithia-tri-silolane 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatricyclo-λ 5 - bismuth heterohexacyclic, 2,2,2,4,4,4,6,6,6-nona-propyl-1,3,5,2,4,6-trithia-tri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona-methyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona-propyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacyclic, 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Trioxanetribismuthhexacyclohexacyclo, 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Trithiabismuth-hexacyclo ... 2,4,6-Tricyclopropyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexacyclo 2,2,2,4,4,4,6,6,6-nona-cyclopropyl-1,3,5,2,4,6-trioxa-tri-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona-cyclopropyl-1,3,5,2,4,6-trithia- tri-λ 5 - bismuth hetero hexacyclic, and 2,2,2,4,4,4,6,6,6-nona-cyclopropyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacyclic.

15. The organometallic compound according to claim 14, wherein the organometallic compound is selected from... Methylbismuth ketone, Ethylbismuth ketone, Methylbismuthylthione, Ethylbismuthylthione, Bi-methylbismuth alkylimine, Bi-ethylbismuth alkylimine, trimethyl-λ 5 - bithionol, triethyl-λ 5 - bithionol, trimethyl-λ 5 - bismuthyl thione, triethyl-λ 5 - bismuthyl thione, Bi, Bi, Bi -trimethyl-λ 5 - bismuth alkyl imines, Bi, Bi, Bi -triethyl- lambda 5 - bismuth alkyl imines, Dimethylbismuthoxy(dimethyl)bismuthane, bis(dimethylbismuthoxy)(methyl)bismuthane, Dimethylbismuthylthio(dimethyl)bismuthane, bis(dimethylbismuthylthio)(methyl)bismuthane, bis(dimethylbismuthyl)amine, Dimethylbismuthylamino(methyl)bismuthyl(dimethylbismuthyl)amine, Diethylbismuthoxy(diethyl)bismuthane, bis(diethylbismuthoxy)(ethyl)bismuthane, Diethylbismuthylthioalkyl(diethyl)bismuthane, bis(diethylbismuthylthio)(ethyl)bismuthane, bis(diethylbismuthyl)amine, Diethylbismuthylamino(ethyl)bismuthyl(diethylbismuthyl)amine, tetramethyl-λ 5 - bismuth alkoxyl (tetramethyl)-λ 5 - bismuth alkyl, bis(tetramethyl-λ 5 - bismuth alkoxyl) (trimethyl)-λ 5 - bismuth alkyl, tetramethyl-λ 5 - bismuth alkylsulfanyl group (tetramethyl)-λ 5 - bismuth alkyl, bis(tetramethyl-λ 5 - bismuth alkylsulfanyl group) (trimethyl)-λ 5 - bismuth alkyl, bis(tetramethyl-λ 5 - bismuth alkyl) amines, tetramethyl-λ 5 - bismuth alkylamino (trimethyl)-λ 5 - bismuth alkyl) (tetramethyl-λ 5 - bismuth alkyl) amine, tetraethyl-λ 5 - bismuth alkoxyl (tetraethyl)-λ 5 - bismuth alkyl, bis(tetraethyl-λ 5 - bismuth alkoxyl) (triethyl)-λ 5 - bismuth alkyl, tetraethyl-λ 5 - bismuth alkylsulfanyl group (tetraethyl)-λ 5 - bismuth alkyl, bis(tetraethyl-λ 5 - bismuth alkylsulfanyl group) (triethyl)-λ 5 - bismuth alkyl, bis(tetraethyl-λ 5 - bismuth alkyl) amines, tetraethyl-λ 5 - bismuth alkylamino(triethyl)-λ 5 - bismuth alkyl)(tetraethyl-λ 5 - bismuth alkyl)amine, 2,4-Dimethyl-1,3,2,4-dioxabismuth tetracyclo 2,4-Diethyl-1,3,2,4-dioxabismuth tetracyclo 2,4-Dimethyl-1,3,2,4-dithiabismuth tetracyclohexane 2,4-Diethyl-1,3,2,4-dithiabismuth tetracyclohexane 2,4-Dimethyl-1,3,2,4-diazabismuth tetracyclo 2,4-Diethyl-1,3,2,4-diazabismuth tetracyclo 2,2,2,4,4,4-hexamethyl-1,3,2,4-dioxadino-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dioxadisilolane 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexamethyl-1,3,2,4-dithia-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexaethyl-1,3,2,4-dithia-λ 5 - bismuth heterotetracyclic, 2,2,2,4,4,4-hexamethyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,2,2,4,4,4-hexaethyl-1,3,2,4-diazadi-λ 5 - bismuth heterotetraloop, 2,4,6-Trimethyl-1,3,5,2,4,6-trioxabismuth-hexacyclohexane, 2,4,6-Triethyl-1,3,5,2,4,6-Trioxane-bismuth-hexacyclohexane, 2,4,6-Trimethyl-1,3,5,2,4,6-trithiabismuth-hexacyclo ... 2,4,6-Triethyl-1,3,5,2,4,6-Trithiabismuth-hexacyclohexane, 2,4,6-Trimethyl-1,3,5,2,4,6-triazabismuth-hexacyclohexane 2,4,6-Triethyl-1,3,5,2,4,6-Triazabismuth-hexacyclohexane 2,2,2,4,4,4,6,6,6-nona-methyl-1,3,5,2,4,6-trioxatris-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trioxatris-λ 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nona-methyl-1,3,5,2,4,6-trithia-tri-silolane 5 - bismuth hetero hexacyclic, 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-trithiatricyclo-λ 5 - bismuth heterohexacyclic, 2,2,2,4,4,4,6,6,6-nona-methyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacyclic, and 2,2,2,4,4,4,6,6,6-nonaethyl-1,3,5,2,4,6-triazatri-λ 5 - bismuth hetero hexacycles.

16. A method for preparing a dry photoresist or hard mask composition for EUV lithography, comprising: Provides an organometallic compound comprising: At least one bismuth element selected from Bi(III) and Bi(V); At least one terminal or bridging ligand A bonded to a bismuth element, wherein ligand A is selected from O, S, and NR, and wherein the R group in NR is selected from H and C1 to C6 alkyl groups; and At least one C1 to C6 alkyl ligand bonded to bismuth.

17. A dry photoresist or hard mask composition for EUV lithography, comprising: Organometallic compounds, the organometallic compounds comprising: At least one bismuth element selected from Bi(III) and Bi(V); At least one terminal or bridging ligand A bonded to a bismuth element, wherein ligand A is selected from O, S, and NR, and wherein the R group in NR is selected from H and C1 to C6 alkyl groups; and At least one C1 to C6 alkyl ligand bonded to bismuth.

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

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

20. The dry photoresist or hardmask composition of claim 17, wherein the organometallic compound has a general formula selected from the group consisting of: General Formula (I), General Formula (II), General Formula (III), General Formula (IV), General Formula (V), General Formula (VI), and General formula (VII), wherein In general formulas (I), (II), (III), (IV), (V), (VI), and (VII): A represents a substance selected from O, S, and NR; R1, R2, R3, R4, R5, R6, R7, and R8 represent alkyl ligands selected from the following: optionally substituted linear C1 to C6 alkyl, optionally substituted branched C1 to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, and optionally substituted C3 to C6 heterocyclic alkyl. n is an integer from 1 to 4; m is an integer from 2 to 5; and In NR, R represents a substance selected from the following: H, optionally substituted linear C1 to C6 alkyl, optionally substituted branched C1 to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, and optionally substituted C3 to C6 heterocyclic alkyl.

21. Dry photoresist or hard mask for EUV lithography, including: Dry photoresist or hard mask compositions comprising organometallic compounds, wherein the organometallic compounds comprise: At least one bismuth element selected from Bi(III) and Bi(V); At least one terminal or bridging ligand A bonded to a bismuth element, wherein ligand A is selected from O, S, and NR, and wherein the R group in NR is selected from H and C1 to C6 alkyl groups; and At least one C1 to C6 alkyl ligand bonded to bismuth.

22. The dry photoresist or hardmask of claim 21, wherein the organometallic compound has a general formula selected from the group consisting of: General Formula (I), General Formula (II), General Formula (III), General Formula (IV), General Formula (V), General Formula (VI), and General formula (VII), wherein, In general formulas (I), (II), (III), (IV), (V), (VI), and (VII): A represents a substance selected from O, S, and NR; R1, R2, R3, R4, R5, R6, R7, and R8 represent alkyl ligands selected from the following: optionally substituted linear or branched C1 to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, and optionally substituted C3 to C6 heterocyclic alkyl. n is an integer from 1 to 4; m is an integer from 2 to 5; and In NR, R represents a substance selected from the following: H, optionally substituted linear C1 to C6 alkyl, optionally substituted branched C1 to C6 alkyl, optionally substituted C3 to C6 cycloalkyl, and optionally substituted C3 to C6 heterocyclic alkyl.

23. A method for forming patterned material features on a substrate, comprising: Provide a material surface on the substrate; A layer of dry photoresist or hard mask composition is formed on the surface of a material, the dry photoresist or hard mask composition comprising an organometallic compound, the organometallic compound comprising: At least one bismuth element selected from Bi(III) and Bi(V); At least one terminal or bridging ligand A bonded to a bismuth element, wherein ligand A is selected from O, S, and NR, and wherein the R group in NR is selected from H and C1 to C6 alkyl groups; and At least one C1 to C6 alkyl ligand bonded to bismuth; The layer is irradiated with energy rays in a patterned manner to form a pattern of radiation exposure areas in the layer; Selectively remove a portion of the layer to form the exposed portion of the material surface; and Etching or ion implantation is used to expose the material surface to form patterned material features.

24. The method of claim 23, wherein the selective removal of a portion of the layer is performed using a technique selected from thermal process steps, plasma ashing, and plasma etching process steps.

25. The method of claim 23, wherein the energy rays include extreme ultraviolet (EUV) radiation.

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