Organometallic photoresists for duv or euv lithography

Patent metadata

Field	Value
Publication number	US-2022317572-A1
Application number	US-202117220412-A
Country	US
Kind code	A1
Filing date	Apr 1, 2021
Priority date	Apr 1, 2021
Publication date	Oct 6, 2022
Grant date	—

Abstract

Organometallic photoresists suitable for use in deep ultraviolet (DUV) or extreme ultraviolet (EUV) lithography are provided. The organometallic photoresists contain an organometallic molecule having least a metal element M selected from the group consisting of Bi, Sb, and mixtures thereof, and having an oxidation state of 3+, and at least one polymerizable group R. A method of forming a patterned materials feature on a substrate utilizing the organometallic photoresist compositions is also provided.

First claim

1 . An organometallic molecule for an organometallic photoresist for deep ultraviolet (DUV) or extreme ultraviolet (EUV) lithography, the organometallic molecule comprising:
at least a metal element M selected from the group consisting of Bi, Sb, and mixtures thereof, and having an oxidation state of 3+; and at least one polymerizable group R.

2 . The organometallic molecule according to claim 1 , having the general formula (I):

wherein
M represents the metal element;
at least one R group of R 1 , R 2 and R 3 represents the polymerizable group;
the remaining R group(s) of R 1 , R 2 and R 3 represent a non-polymerizable group; and
n is an integer in a range from 1 to the maximum number of hydrogen atoms of the R 3 group.

3 . The organometallic molecule according to claim 2 , wherein n is an integer in a range from 1 to 12.

4 . The organometallic molecule according to claim 1 , having one of the general formulae (a), (b), (c), (d), (e), or (f):

wherein
at least one R group of R 1 , R 2 and R 3 represents the polymerizable group; and
the remaining R group(s) of R 1 , R 2 and R 3 represent a non-polymerizable group.

5 . The organometallic molecule according to claim 1 , wherein the polymerizable group is selected from the group consisting of a linear, a branched, a cyclic, or a heterocyclic unsaturated monomer having an alkenyl group or an alkynyl group.

6 . The organometallic molecule according to claim 1 , wherein the polymerizable group is selected from the group consisting of vinyl, isopropenyl, 1,3-butadienyl, styrene, alpha-methylstyrene, vinylstyrene, cyclopentenyl, cyclohexenyl, cycloheptenyl, acrylate, methacrylate, 2,4-pentadienoate, acrylamide, methacrylamide, 2,4-pentadienamide, phenylacrylate, phenylmethacrylate, phenyl-2,4-pentadienoate, phenylacrylamide, phenylmethacrylamide, phenyl-2,4-pentadienamide, vinylbenzoate, isopropenylbenzoate, butadienylbenzoate, N-vinylbenzamide, N-isopropenylbenzamide, N-butadienylbenzamide, and derivatives thereof; and/or the non-polymerizable group is selected from the group consisting of linear or branched or a cyclic unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; an unsubstituted or substituted aryl group having 3 to 30 carbon atoms; an unsubstituted or an substituted unsaturated or a saturated heterocyclic group having a 3 to 30 membered ring; and derivatives thereof.

7 . The organometallic molecule according to claim 6 , wherein the linear or the branched alkyl group is selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosayl, and derivatives thereof; and/or the cyclic alkyl group is selected from the group consisting of cyclopentane, cyclohexane, cycloheptane, cyclooctane, and derivatives thereof; and/or the aryl group is selected from the group consisting of phenyl, naphthyl, anthracenyl, phenanthrenyl, and derivatives thereof; and/or the saturated or unsaturated heterocyclic group having one or two heteroatoms is selected from the group consisting of pyrrolidine, pyrrole, tetrahydrofuran, furan, tetrahydrothiophene, thiophene, imidazolidine, imidazole, oxazolidine, oxyzole, thiazolidine, thiazole, dioxolane, dithiolane, piperidine, pyridine, tetrahydropyran, pyran, thiane, thiopyran, diazinane, diazine, in particular pyridazin (1,2-diazin), pyrimidine (1,3-diazin) and pyrazin (1,4-diazin), morpholine, oxazine, thiomorpholine, thiazine, dioxane, dioxine, dithiane, dithiin, quinolone, isoquinoline, and derivatives thereof.

8 . The organometallic molecule according to claim 2 , wherein the R groups are either separated from each other or at least two R groups are connected via a covalent bond, or a connecting atom, selected from the group consisting of —C—, —O—, —S—, or a connecting group, selected from the group consisting of —C(O)—, —S(O)—, and —S(O) 2 —, between any of two C atoms of the two R groups.

9 . The organometallic molecule according to 2 , wherein all R groups are polymerizable groups.

10 . The organometallic molecule according to claim 2 , further comprising a linking atom or linking group between at least one R group and the metal element M.

11 . The organometallic molecule according to claim 10 , wherein the linking atom is selected from the group consisting of —O—, —S—, —Se—, —Te—, and/or the linking group is selected from the group consisting of —C(H) 2 —, —N(X)—, and —P(X)—, wherein X is selected from the group consisting linear or branched or a cyclic unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; an unsubstituted or substituted aryl group having 3 to 30 carbon atoms; an unsubstituted or a substituted unsaturated or a saturated heterocyclic group having a 3 to 30 membered ring; and derivatives thereof.

12 . The organometallic molecule according claim 1 , wherein the organic molecule is an organobismuth(III) molecule or an organoantimony(III) molecule, wherein the organobismuth(III) or organoantimony(III) molecules are selected from the group consisting of:
tris(4-ethenyl)bismuthane, 1,4-bis(di(4-ethenyl)bismuthanyl)benzene, 1,3,5-tris(di(4-ethenyl)bismuthanyl)benzene, tris(4-ethenyl)stibane, 1,4-bis(di(4-ethenyl)stibanyl)benzene, 1,3,5-tris(di(4-ethenyl)stibanyl)benzene, tris(4-propen-2-yl)bismuthane, 1,4-bis(di(4-propen-2-yl)bismuthanyl)benzene, 1,3,5-tris(di(4-propen-2-yl)bismuthanyl)benzene, tris(4-propen-2-yl)stibane, 1,4-bis(di(4-propen-2-yl)stibanyl)benzene, 1,3,5-tris(di(4-propen-2-yl)stibanyl)benzene, tris(4-buta-1,3-dien-1-yl)bismuthane, 1,4-bis(di(4-buta-1,3-dien-1-yl)bismuthanyl)benzene, 1,3,5-tris(di(4-buta-1,3-dien-1-yl)bismuthanyl)benzene, tris(4-buta-1,3-dien-1-yl)stibane, 1,4-bis(di(4-buta-1,3-dien-1-yl)stibanyl)benzene, 1,3,5-tris(di(4-buta-1,3-dien-1-yl)stibanyl)benzene, 5-(4-ethenylphenyl)-2,8-diethenyl-dibenzobismole, 1,4-bis(2,8-diethenyl-dibenzobismol-5-yl)benzene, 1,3,5-tris(2,8-diethenyl-dibenzobismol-5-yl)benzene, 5-(4-ethenylphenyl)-2,8-diethenyl-dibenzostibole, 1,4-bis(2,8-diethenyl-dibenzostibol-5-yl)benzene, 1,3,5-tris(2,8-diethenyl-dibenzostibol-5-yl)benzene, tris(4-propen-2-ylphenyl)bismuthane, 1,4-bis(di(4-propen-2-ylphenyl)bismuthanyl)benzene, 1,3,5-tris(di(4-propen-2-ylphenyl)bismuthanyl)benzene, tris(4-propen-2-ylphenyl)stibane, 1,4-bis(di(4-propen-2-ylphenyl)stibanyl)benzene, 1,3,5-tris(di(4-propen-2-ylphenyl)stibanyl)benzene, tris(4-buta-1,3-dien-1-ylphenyl)bismuthane, 1,4-bis(di(4-buta-1,3-dien-1-ylphenyl)bismuthanyl)benzene, 1,3,5-tris(di(4-buta-1,3-dien-1-ylphenyl)bismuthanyl)benzene, tris(4-buta-1,3-dien-1-ylphenyl)stibane, 1,4-bis(di(4-buta-1,3-dien-1-ylphenyl)stibanyl)benzene, 1,3,5-tris(di(4-buta-1,3-dien-1-ylphenyl)stibanyl)benzene, tris(cyclopent-2-enyl)bismuthane, 1,4-bis(cyclopent-2-enyl)-bismuthanyl)benzene, 1,3,5-tris(di(cyclopent-2-enyl)bismuthanyl)benzene, tris(cyclopent-2-enyl)stibane, 1,4-bis(di(cyclopent-2-enyl)stibanyl)benzene, 1,3,5-tris(di(cyclopent-2-enyl)stibanyl)benzene, tris(cyclohex-2-enyl)bismuthane, 1,4-bis(cyclohex-2-enyl)-bismuthanyl)benzene, 1,3,5-tris(di(cyclohex-2-enyl)bismuthanyl)benzene, tris(cyclohex-2-enyl)stibane, 1,4-bis(di(cyclohex-2-enyl)stibanyl)benzene, 1,3,5-tris(di(cyclohex-2-enyl)stibanyl)benzene, tris(cyclohept-2-enyl)bismuthane, 1,4-bis(cyclohept-2-enyl)-b

Assignees

• IBM

Inventors

• Meijer Gerhard Ingmar
• Weber Valery
• Staar Peter Willem Jan

Classifications

• G03F7/0042 Primary

  with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists (G03F7/075 takes precedence) · CPC title

• G03F7/2004 Primary

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title

• C07F9/94

  Bismuth compounds · CPC title

• C07F9/92

  Aromatic compounds · CPC title

• C07F9/902

  Compounds without antimony-carbon linkages · CPC title