CN117659073A - Single molecule resin based on polysulfide onium salt and photoresist composition thereof - Google Patents

Single molecule resin based on polysulfide onium salt and photoresist composition thereof Download PDF

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CN117659073A
CN117659073A CN202211035743.3A CN202211035743A CN117659073A CN 117659073 A CN117659073 A CN 117659073A CN 202211035743 A CN202211035743 A CN 202211035743A CN 117659073 A CN117659073 A CN 117659073A
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alkyl
aryl
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陈金平
王亚珂
李嫕
曾毅
于天君
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Technical Institute of Physics and Chemistry of CAS
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Technical Institute of Physics and Chemistry of CAS
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Abstract

The invention provides a series of novel single-molecule resins based on polysulfide, namely compounds shown in a formula (I), which have cheap and easily available raw materials and simple synthesis process; the compound shown in the formula (I) is used as a single-component non-chemically amplified photoresist, so that the problems of uneven distribution of an acid generator and an acid diffusion inhibitor in the chemically amplified photoresist, uneven acid diffusion and the like are avoided, and the obtained pattern has high resolution and low line edge roughness.

Description

Single molecule resin based on polysulfide onium salt and photoresist composition thereof
Technical Field
The invention belongs to the technical field of photoetching materials, and particularly relates to a single-molecule resin based on a polysulfide salt, a photoresist composition, a photoresist coating and application thereof.
Background
Molecular glass is a functional material composed of small monodisperse organic molecules, and can form stable amorphous glass at room temperature. Compared with the traditional polymer photoresist, the molecular glass has a monodisperse structure block with smaller size, a reproducible structure with definite molecular weight and stereochemistry, can realize accurate synthesis, and is beneficial to obtaining high-resolution and low LWR/LER patterns. Traditionally used Chemically Amplified Resists (CARs) rely on hybrid or polymer-bonded photoacid generators (PAGs) to achieve solubility differences. This chemical amplification system has a series of problems such as having high Line Edge Roughness (LER), and post-exposure instability, etc. To solve these problems, research into novel non-chemically amplified resists (n-CARs) is receiving increasing attention. n-CARs is a radiation-sensitive material that does not require the addition of PAGs in its formulation and contains only one component of the host material, thus effectively solving the problem of compatibility of the host material with additives and the problem of uneven acid diffusion after exposure, thereby reducing LER values. However, the number of n-CARs is very limited compared to the number of CARs reported so far, especially molecular glass based n-CARs. Therefore, the development of molecular glass n-CARs with strong lithographic potential is of great interest, especially for sub-20 nm patterning applications with low LER/LWR characteristics.
Disclosure of Invention
In order to solve the technical problems, the invention provides a single-molecule resin based on a polysulfide salt and a photoresist composition containing the single-molecule resin.
The technical scheme of the invention is as follows:
a compound of formula (I):
wherein,
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 identical or different, each independently selected from-S + R S1 R S2 、-O-C 1-15 alkyl-C 6-20 aryl-S + R S1 R S2 Or a group Z which is H, unsubstituted or optionally substituted by one, two or more R A Substituted as follows: c (C) 1-15 Alkyl, C 1-15 Alkoxy, C 3-20 Cycloalkyl, C 6-20 Aryl, 5-20 membered heteroaryl, 3-20 membered heterocyclyl, -C 1-15 alkyl-C 6-20 Aryl, -C 1-15 Alkyl-5-20 membered heteroaryl, -C 1-15 alkyl-CO-C 6-20 Aryl, -C 1-15 alkyl-CO-5-20 membered heteroaryl, -C 1-15 alkyl-CO-C 1-15 Alkyl, -C 1-15 alkyl-CO-C 3-20 Cycloalkyl;
R 0 selected from the group consisting of-O-C 1-15 alkyl-C 6-20 aryl-S + R S1 R S2 Or a group Z as described above;
R A selected from = O, NO 2 、C 1-15 Alkyl, C 1-15 Alkoxy, C 3-20 Cycloalkyl, C 6-20 Aryl, 5-20 membered heteroaryl;
R S1 、R S2 identical or different, each independently selected from unsubstituted, or optionally substituted with one, two or more R B Substituted as follows: c (C) 1-15 Alkyl, C 3-20 Cycloalkyl, C 6-20 Aryl, 5-20 membered heteroaryl, deuterated C 1-15 Alkyl (e.g. deuteromethyl), or R S1 、R S2 And S attached thereto form together an unsubstituted or optionally substituted one, two or more R B Substituted 5-8 membered sulfur-containing heterocyclyl; the 5-8 membered sulfur-containing heterocycle optionally further contains 1-2 oxygen or sulfur; the 5-8 membered sulfur-containing heterocycle is optionally further substituted with one or two benzene ringsCondensing;
R B identical or different, independently of one another, from H, oxo (=O), nitro, CN, C 1-15 Alkyl, C 1-15 An alkoxy group;
E 1 、E 2 identical or different, each independently selected from C 1-15 Alkyl, C 3-20 Cycloalkyl, unsubstituted, or optionally substituted with one, two or more sulfonium salt groups-S + R S1 R S2 Substituted as follows: c (C) 6-20 Aryl, 5-20 membered heteroaryl;
X – anions such as halide, carboxylate, sulfate, alkylsulfonate, haloalkylsulfonate (e.g., trifluoromethylsulfonate, perfluoropropylsulfonate, perfluorobutylsulfonate), p-toluenesulfonate, anions of sulfonamides, tetrafluoroborate, hexafluoroantimonate, hexafluorophosphate or bistrifluoromethane sulfonylimide;
n is equal to the sulfonium salt group-S in the molecule + R S1 R S2 S in (2) + Number S of (S) + And X – Making the compound be electrically neutral, wherein n is an integer of 2-8; i.e. compounds of formula (I) having 2 to 8 groups-S + R S1 R S2 。
In some embodiments of the invention, compounds of formula (I) have 2 to 6 groups-S + R S1 R S2 For example having 2,3, 4,5, 6 radicals-S + R S1 R S2 。
In some embodiments of the invention, R 1 -R 20 Having 4 radicals-S + R S1 R S2 And each phenyl group has 1 group-S + R S1 R S2 。
In some embodiments of the invention, compounds of formula (I) have 2 to 6 groups-S + R S1 R S2 And E is 1 、E 2 Each having a group-S + R S1 R S2 。
In some embodiments of the invention, the sulfonium salt group is located in the ortho, meta or para position.
According to an embodiment of the invention, the sulfonium salt group-S + R S1 R S2 Selected from unsubstituted or optionally substituted by one, two or more R 1 ' substituted following groups:
wherein,representing a connection bond; r is R 1a And R is 1b May be the same or different and are each independently selected from unsubstituted or substituted with one, two or more R C Substituted as follows: c (C) 1-15 Alkyl, C 3-20 Cycloalkyl, -C 1-15 alkyl-C 6-20 Aryl, -C 1-15 Alkyl-5-20 membered heteroaryl, -C 6-20 aryl-C 1-15 Alkyl, deuterated C 1-15 An alkyl group; r is R C 、R 1 'same or different', independently of each other, selected from =o, nitro, C 1-15 Alkyl, C 1-15 An alkoxy group; m is selected from integers from 0 to 5; y is selected from CH 2 、O、S、C(O)；
Preferably, the radical R 1a And R is 1b One selected from the following structures:
wherein,representing a connection key.
In some embodiments of the invention, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 Identical or different, each independently selected from H, -S + R S1 R S2 、C 1-6 Alkyl, C 1-6 An alkoxy group; r is R S1 、R S2 Selected from C 1-6 Alkyl, C 6-12 An aryl group;
in some embodiments of the invention, R 0 Is H, -O-C 1-6 alkyl-C 6-12 aryl-S + R S1 R S2 、C 1-6 Alkyl, C 1-6 Alkoxy, R S1 、R S2 Selected from C 1-6 Alkyl, C 6-12 An aryl group;
in some embodiments of the invention, E 1 、E 2 Is C 1-8 Alkyl, C 6-12 Aryl or quilt-S + R S1 R S2 Substituted C 6-12 Aryl, wherein R is S1 、R S2 Selected from C 1-6 Alkyl, C 6-12 An aryl group;
in some preferred embodiments of the invention, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 Identical or different, each independently selected from H, -S + (C 1-6 Alkyl group 2 、C 1-6 Alkoxy, -S + (C 6-12 Aryl group 2 、C 1-6 An alkyl group;
R 0 is H;
E 1 、E 2 is-C 6-12 aryl-S + (C 1-6 Alkyl group 2 、C 6-12 Aryl, C 1-8 Alkyl, -C 6-12 aryl-S + (C 6-12 Aryl group 2 。
In some embodiments of the present invention, the compounds of formula (I) are symmetrical structures, i.e., the structures on the 4 benzene rings are identical.
As an example, the compound of formula (I) is selected from the following compounds:
the invention also provides a preparation method of the compound shown in the formula (I), which comprises the following steps: combining compound (IV) with R S2 Mixing L and MX, and reacting to obtain a compound shown as a formula (I); l is a leaving group, such as halogen, etc.; r is R S2 MX is a metal salt as defined above;
wherein R is 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 R is as defined above 0 ' is-O-C 1-15 alkyl-C 6-20 aryl-SR S1 Or a group Z, R 1 ’、R 2 ’、R 3 ’、R 4 ’、R 5 ’、R 6 ’、R 7 ’、R 8 ’、R 9 ’、R 10 ’、R 11 ’、R 12 ’、R 13 ’、R 14 ’、R 15 ’、R 16 ’、R 17 ’、R 18 ’、R 19 ’、R 20 ' is-S-R S1 、-O-C 1-15 alkyl-C 6-20 aryl-SR S1 Or groups Z, E 1 ’、E 2 ' independently selected from C 1-15 Alkyl, C 3-20 Cycloalkyl, not takenSubstituted, or optionally substituted, with one, two or more thioether groups-S-R S1 Substituted as follows: c (C) 6-20 Aryl, 5-20 membered heteroaryl.
According to the present invention, the compound of formula (IV) may be prepared by a process comprising:
wherein R is 0 ’、R 1 ’、R 2 ’、R 3 ’、R 4 ’、R 5 ’、R 6 ’、R 7 ’、R 8 ’、R 9 ’、R 10 ’、R 11 ’、R 12 ’、R 13 ’、R 14 ’、R 15 ’、R 16 ’、R 17 ’、R 18 ’、R 19 ’、R 20 ’、E 1 ’、E 2 ' as defined above.
The invention also provides another preparation method of the compound shown in the formula (I), which comprises the following steps: reacting a compound shown in a formula (V) with a sulfoxide compound to obtain a compound shown in a formula (I);
wherein R is 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 R is as defined above 0 "is-O-C 1-15 alkyl-C 6-20 Aryl or radicals Z, R 1 ”、R 2 ”、R 3 ”、R 4 ”、R 5 ”、R 6 ”、R 7 ”、R 8 ”、R 9 ”、R 10 ”、R 11 ”、R 12 ”、R 13 ”、R 14 ”、R 15 ”、R 16 ”、R 17 ”、R 18 ”、R 19 ”、R 20 "H, -O-C 1-15 alkyl-C 6-20 Aryl, or radicals Z, E 1 ”、E 2 "independently selected from: c (C) 1-15 Alkyl, C 3-20 Cycloalkyl, C 6-20 Aryl, 5-20 membered heteroaryl.
Optionally, the compound of formula (I) may be ion exchanged with a corresponding anion solution to provide a compound of formula (I) having a different anion.
The sulfoxide compound is R S1 -SO-R S2 。
According to an embodiment of the present invention, the reaction may be carried out under the action of a catalyst, which may be trifluoromethanesulfonic anhydride or trifluoromethanesulfonic acid;
the invention also provides application of the compound shown in the formula (I) in preparing photoresist.
According to an embodiment of the present invention, the photoresist is a one-component photoresist containing only the compound represented by formula (I) except a solvent.
The invention also provides a photoresist composition, which comprises a compound shown as a formula (I).
According to an embodiment of the present invention, the photoresist composition further comprises a solvent selected from one, two or more of the following: propylene Glycol Methyl Ether Acetate (PGMEA), dimethylformamide (DMF), cyclohexanone, ethyl n-pentanone, ethyl iso-pentanone, ethanol, acetonitrile, isopropanol, acetone, methyl n-pentanone, methyl iso-pentanone.
According to an embodiment of the present invention, the photoresist composition is a positive or negative photoresist composition comprising the compound represented by the formula (I) and a photoresist solvent.
In one embodiment, the photoresist composition is a one-component photoresist, which is composed of the compound of formula (I) and a photoresist solvent, i.e., the photoresist composition includes only one component, i.e., the compound of formula (I), except the photoresist solvent.
The invention also provides a photoresist coating, which comprises a compound shown in a formula (I).
The invention also provides a preparation method of the photoresist coating, and the photoresist composition is applied to a substrate to prepare the photoresist coating.
Preferably, the application mode is spin coating.
Preferably, the substrate is a silicon wafer substrate.
Preferably, the photoresist coating is a thin film.
The invention also provides application of the photoresist coating in photoetching.
The compound shown in the formula (I) has higher glass transition temperature (about 200 ℃) because of the unique polysulfide salt structure, and can be used for photoetching processing.
According to embodiments of the invention, the photoresist coating may be used in 248nm lithography, 193nm lithography, extreme Ultraviolet (EUV) lithography, nanoimprint lithography or electron beam lithography, preferably for EUV as well as electron beam lithography techniques.
The beneficial effects of the invention are as follows:
(1) The invention provides a series of novel single-molecule resins based on polysulfide, namely compounds shown in a formula (I), which have cheap and easily available raw materials and simple synthesis process;
(2) The compound shown in the formula (I) can be used as a single-component non-chemical amplification photoresist, so that the problems of uneven distribution of acid generating agents and acid diffusion preventing agents, uneven acid diffusion and the like in the chemical amplification photoresist are avoided, and the obtained pattern has high resolution and low line edge roughness.
(3) The silicon-containing polysulfide salt single-molecule resin contains silicon atoms, has higher etching resistance and can increase the interaction between the resin and a substrate. Meanwhile, as silicon has a tetrahedral bonding mode, the silicon-containing polyphenyl single-molecule resin has good film forming property;
(4) The silicon-containing polyphenyl sulfonium salt single-molecule resin has a definite molecular structure and a single molecular size, and can well meet the requirement of high-resolution photoetching.
Terminology and definition
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the claimed subject matter belongs.
"more" means three or more.
The term "C 1-15 Alkyl "is understood to mean a straight-chain or branched saturated monovalent hydrocarbon radical having from 1 to 15 carbon atoms. For example, "C 1-6 Alkyl "means straight and branched alkyl groups having 1,2, 3,4, 5, or 6 carbon atoms. The alkyl group is, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-ethylpropyl, 1, 2-dimethylpropyl, neopentyl, 1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3-dimethylbutyl, 2-dimethylbutyl, 1-dimethylbutyl, 2, 3-dimethylbutyl, 1, 3-dimethylbutyl, or 1, 2-dimethylbutyl, or the like, or an isomer thereof.
The term "C 1-15 Alkoxy "is understood to mean-O-C 1-15 Alkyl, wherein C 1-15 Alkyl has the above definition.
The term "C 3-20 Cycloalkyl "is understood to mean a saturated monovalent monocyclic, bicyclic or polycyclic hydrocarbon ring (also known as a thick cyclic hydrocarbon ring) having from 3 to 20 carbon atoms. Bicyclic or polycyclic cycloalkyl includes fused-ring cycloalkyl, bridged-ring cycloalkyl, spirocycloalkyl; by fused ring is meant a fused ring structure formed by two or more cyclic structures sharing two adjacent ring atoms with each other (i.e., sharing a bond). The bridged ring refers to a condensed ring structure formed by two or more ring-mounted structures sharing two non-adjacent ring atoms with each other. The spiro ring refers to a condensed ring structure formed by two or more cyclic structures sharing one ring atom with each other. For example, said C 3-20 Cycloalkyl can be C 3-8 Monocyclic cycloalkyl radicals, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloHeptyl, cyclooctyl, or C 7-12 And cycloalkyl rings such as decalin rings; may also be C 7-12 Bridged cycloalkyl radicals, e.g. norbornane, adamantane, bicyclo [2,2]Octane.
The term "3-20 membered heterocyclyl" means a saturated or unsaturated monovalent monocyclic or bicyclic hydrocarbon ring containing 1 to 5 heteroatoms independently selected from N, O and S, preferably a "3-10 membered heterocyclyl". The term "3-10 membered heterocyclyl" means a saturated monovalent monocyclic or bicyclic hydrocarbon ring containing 1 to 5, preferably 1 to 3 heteroatoms selected from N, O and S. The heterocyclic group may be attached to the remainder of the molecule through any of the carbon atoms or a nitrogen atom, if present. In particular, the heterocyclic groups may include, but are not limited to: 4-membered rings such as azetidinyl, oxetanyl; a 5-membered ring such as tetrahydrofuranyl, dioxolyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, pyrrolinyl; or a 6 membered ring such as tetrahydropyranyl, piperidinyl, morpholinyl, dithianyl, thiomorpholinyl, piperazinyl or trithianyl; or a 7-membered ring such as diazepanyl. Optionally, the heterocyclyl may be benzo-fused. The heterocyclyl may be bicyclic, such as, but not limited to, a 5,5 membered ring, such as hexahydrocyclopenta [ c ] pyrrol-2 (1H) -yl ring, or a 5,6 membered bicyclic ring, such as hexahydropyrrolo [1,2-a ] pyrazin-2 (1H) -yl ring. The nitrogen atom-containing ring may be partially unsaturated, i.e., it may contain one, two or more double bonds, such as, but not limited to, 2, 5-dihydro-1H-pyrrolyl, 4H- [1,3,4] thiadiazinyl, 4, 5-dihydro-oxazolyl, or 4H- [1,4] thiazinyl, or it may be benzo-fused, such as, but not limited to, dihydroisoquinolyl, 1, 3-benzoxazolyl, 1, 3-benzodioxolyl. According to the invention, the heterocyclic group is non-aromatic.
The term "C 6-20 Aryl "is understood to mean a mono-, bi-or tricyclic hydrocarbon ring, preferably" C ", of monovalent aromatic or partly aromatic nature having 6 to 20 carbon atoms 6-14 Aryl group). The term "C 6-14 Aryl "is understood to mean preferably mono-, bi-or tri-cyclic having monovalent aromaticity or partial aromaticity of 6, 7,8, 9, 10, 11, 12, 13 or 14 carbon atomsCyclic hydrocarbon rings ("C) 6-14 Aryl), in particular a ring having 6 carbon atoms ("C) 6 Aryl "), such as phenyl; or biphenyl, or a ring having 9 carbon atoms ("C 9 Aryl "), e.g. indanyl or indenyl, or a ring having 10 carbon atoms (" C 10 Aryl "), such as tetralin, dihydronaphthyl or naphthyl, or a ring having 13 carbon atoms (" C " 13 Aryl "), e.g. fluorenyl, or a ring having 14 carbon atoms (" C) 14 Aryl "), such as anthracenyl. When said C 6-20 When aryl is substituted, it may be mono-substituted or poly-substituted. The substitution site is not limited, and may be, for example, ortho, para or meta substitution.
The term "5-20 membered heteroaryl" is understood to include such monovalent monocyclic, bicyclic or tricyclic aromatic ring systems: having 5 to 20 ring atoms and containing 1 to 5 heteroatoms independently selected from N, O and S, such as "5-14 membered heteroaryl". The term "5-14 membered heteroaryl" is understood to include such monovalent monocyclic, bicyclic or tricyclic aromatic ring systems: it has 5,6, 7,8, 9, 10, 11, 12, 13 or 14 ring atoms, in particular 5 or 6 or 9 or 10 carbon atoms, and it contains 1 to 5, preferably 1 to 3 heteroatoms each independently selected from N, O and S and, in addition, can be benzo-fused in each case. In particular, the heteroaryl group is selected from thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, thia-4H-pyrazolyl and the like and their benzo derivatives, such as benzofuryl, benzothienyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, benzotriazole, indazolyl, indolyl, isoindolyl and the like; or pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and the like, and their benzo derivatives, such as quinolinyl, quinazolinyl, isoquinolinyl, and the like; or an axcinyl group, an indolizinyl group, a purinyl group, etc., and their benzo derivatives; or cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and the like.
The term "C" above 1-15 The definition of alkyl "applies to other C-containing groups as well 1-15 Radicals of alkyl radicals, e.g. -C 1-15 alkyl-C 6-20 Aryl, -C 1-15 Alkyl-5-20 membered heteroaryl, -C 1-15 alkyl-CO-C 6-20 Aryl, -C 1-15 alkyl-CO-5-20 membered heteroaryl, -C 1-15 alkyl-CO-C 1-15 Alkyl, -C 1-15 alkyl-CO-C 3-20 Cycloalkyl groups, and the like.
Similarly, C 6-20 Aryl, 5-20 membered heteroaryl, C 3-20 Cycloalkyl has the same definition throughout.
Drawings
FIG. 1 is a differential scanning calorimetry and thermal weight loss plot of compound I-1 of example 2 of the present invention.
FIG. 2 is a differential scanning calorimetry and thermal weight loss plot of compound I-2 of example 4 of the present invention.
FIG. 3 is a Scanning Electron Microscope (SEM) image of compound I-1 of example 2 of the present invention.
FIG. 4 is an Atomic Force Microscope (AFM) image of compound I-1 in example 2 of the present invention.
FIG. 5 is a Scanning Electron Microscope (SEM) image of negative photoresist film forming lithography stripes (exposure periods of 60nm,50nm,44 nm) of the host material of the compound I-1 in example 2 of the present invention.
Detailed Description
The technical scheme of the invention will be further described in detail below with reference to specific embodiments. It is to be understood that the following examples are illustrative only and are not to be construed as limiting the scope of the invention. All techniques implemented based on the above description of the invention are intended to be included within the scope of the invention.
Unless otherwise indicated, the starting materials and reagents used in the following examples were either commercially available or may be prepared by known methods.
Example 1
The compound IV-1 is prepared by the following synthetic route:
into a 200mL Schleck flask was charged bis (3, 5-dibromophenyl) -diphenylsilane (6 g,9mmol,1.0 eq), 3-methylthiophenylboronic acid (7.5 g,45mmol,5.0 eq) and 80mL tetrahydrofuran. Anhydrous potassium carbonate solid (6.2 g,45mmol,5 eq) was weighed into 30mL of water and added to the reaction flask. The system was deoxygenated three times under nitrogen atmosphere. Then tetrakis (triphenylphosphine) palladium catalyst (208 mg,0.18mmol,0.02 eq) was added under nitrogen, heated to reflux for 10h, cooled to room temperature, and extracted with dichloromethane/water, the organic layers combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. And (3) dropwise adding a large amount of dichloromethane solution of the product into a large amount of ethanol for sedimentation, stirring for 2 hours at room temperature, and carrying out suction filtration and drying to obtain white solid 7.4, wherein the yield is 95%. 1 H NMR(400MHz,CDCl 3 ) δ=7.82 (s, 6H), 7.69 (d, j= 7.8,4H), 7.49-7.42 (m, 6H), 7.41 (s, 4H), 7.34 (d, j= 6.0,4H), 7.32 (d, j= 6.0,4H), 7.22-7.24 (m, 4H), 2.45 (s, 12H); MS (ESI) m/z= 847.20, calculated C 52 H 44 S 4 SiNa + m/z＝847.20([M+Na] + )。
Example 2
The compound I-1 was prepared as follows:
into a 250mL round bottom flask was charged compound IV-1 (5 g,6mmol,1 eq), silver triflate (9.2 g,36mmol,6 eq), 40mL dry dichloromethane was weighed, dissolved and stirred. 30mL (5.1 g,36mmol,6 eq) of methyl iodide in methylene chloride was slowly added dropwise, and the mixture was reacted under dark conditions for 3 hours after the completion of the dropwise addition. The reaction mixture was allowed to stand and the supernatant was removed, and the solid was dissolved with acetonitrile, and the AgI precipitate in the reaction mixture was removed by filtration to obtain a colorless solution. After a large amount of solvent is removed by rotary evaporation, white precipitate can be obtained by dripping the solution into diethyl ether, and the yield is 90%. 1 H NMR(400MHz,CD 3 CN)δ8.19(s,6H),8.02(d,J＝7.7Hz,4H),7.98(s,4H),7.9(d,J＝7.6Hz,4H),7.76(dd,J＝7.7,4H),7.75(d,J＝7.2,4H),7.60-747 (m, 6H), 3.17 (s, 24H); MS (ESI) m/z= 344.42, calculated C 57 H 56 F 3 O 3 S 5 Si 3+ m/z＝344.42([M] 3+ ) The method comprises the steps of carrying out a first treatment on the surface of the m/z= 148.95, calculated CF 3 SO 3 - m/z＝148.95([M] - )。
Example 3
The compound IV-2 was prepared as follows:
the specific procedure was as in example 1, except that 3-methylthiophenylboronic acid was replaced with 4-methylthiophenylboronic acid, and the reaction yield was 85%. 1 H NMR(400MHz,CDCl 3 ) δ=7.82 (s, 6H), 7.69 (d, j= 7.8,4H), 7.57 (d, j= 6.6,8H), 7.49-7.42 (m, 6H), 7.40 (d, j= 6.6,8H), 2.45 (s, 12H); MS (ESI) m/z= 847.20, calculated C 52 H 44 S 4 SiNa + m/z＝847.20([M+Na] + )。
Example 4
The compound I-2 was prepared as follows:
the specific procedure was as in example 2, except that IV-1 was replaced with IV-2, with a reaction yield of 85%. 1 H NMR (400 mhz, cdcn) δ=8.14 (s, 2H), 7.97 (s, 20H), 7.72 (d, j= 6.6,8H), 7.6-7.47 (m, 6H), 3.16 (s, 24H); MS (ESI) m/z= 344.42, calculated C 57 H 56 F 3 O 3 S 5 Si 3+ m/z＝344.42([M] 3+ ) The method comprises the steps of carrying out a first treatment on the surface of the m/z= 148.95, calculated CF 3 SO 3 - m/z＝148.95([M] - )。
Example 5
The compound IV-3 was prepared as follows:
in a 200mL Schleck flask was charged bis (3, 5-dibromophenyl) -bis (4-methylthiophenyl) silane (6 g,8mmol,1.0 eq), 3, 4-dimethoxyphenylboronic acid (7.3 g,40mmol,5.0 eq), dioxane 90mL. Anhydrous potassium carbonate solid (5.5 g,40mmol,5 eq) was weighed into 30mL of water and added to the reaction flask. The system was deoxygenated three times under nitrogen atmosphere. Then tetrakis (triphenylphosphine) palladium catalyst (185 mg,0.16mmol,0.02 eq) was added under nitrogen, heated to reflux for 10h, cooled to room temperature, and extracted with dichloromethane/water, the organic layers combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. And (3) dropwise adding a large amount of ethanol into a dichloromethane solution of the product, settling, stirring at room temperature for 2 hours, and carrying out suction filtration and drying to obtain white solid 7.4, wherein the yield is 95%. 1 H NMR(400MHz,CDCl 3 ) δ=7.78 (s, 2H), 7.76 (s, 4H), 7.60 (d, j= 7.6,4H), 7.27 (d, j= 7.6,4H), 7.13 (d, j= 8.0,4H), 7.04 (s, 4H), 6.92 (d, j= 8.2,4H), 3.90 (s, 12H), 3.83 (s, 12H), 2.48 (s, 6H); MS (ESI) m/z= 995.3, calculated C 58 H 56 O 8 S 2 SiNa + m/z＝995.3([M+Na] + )。
Example 6
The compound I-3 was prepared as follows:
the specific procedure was as in example 2, except that IV-1 was replaced with IV-3, with a reaction yield of 90%. 1 H NMR (400 mhz, cdcn) δ=8.04 (s, 2H), 7.98 (s, 4H), 7.46 (d, j= 7.6,4H), 7.43 (d, j= 7.6,4H), 7.39 (d, j= 8.0,4H), 7.00 (d, j= 8.2,4H), 6.94 (s, 4H), 3.92 (s, 12H), 3.83 (s, 12H), 3.15 (s, 12H); MS (ESI) m/z= 1151.32, calculated C 61 H 62 F 3 O 11 S 3 Si + m/z＝1151.32([M] + ) The method comprises the steps of carrying out a first treatment on the surface of the m/z= 148.95, calculated CF 3 SO 3 - m/z＝148.95([M] - )。
Example 7
The compound V-4 was prepared as follows:
the specific procedure was as in example 5, except that compound III-3 was replaced with III-4, 3, 4-dimethoxyphenylboronic acid was replaced with phenylboronic acid, and the reaction yield was 90%. 1 H NMR(400MHz,CDCl 3 ) δ=8.0 (s, 6H), 7.57 (d, j= 7.3,8H), 7.50-7.37 (m, 12H), 0.66 (s, 6H); MS (ESI) m/z= 539.22, calculated C 38 H 32 SiNa + m/z＝539.22([M+Na] + )。
Example 8
The compound I-4 was prepared as follows:
into a 250mL round bottom flask was charged compound V-4 (5 g,9.7mmol,1 eq), diphenyl sulfoxide (9.8 g,48.5mmol,5 eq), and 20mL of dry dichloromethane was measured for dissolution. The reaction solution was placed in an acetonitrile bath, 20mL of a methylene chloride solution (27 g,97mmol,10 eq) of trifluoromethanesulfonic anhydride was added dropwise, and after the completion of the addition, the reaction was carried out under dark conditions for 5 hours. Most of the reaction solution was removed by rotary evaporator, and white precipitate was obtained by dropwise addition to diethyl ether in 80% yield. 1 H NMR(400MHz,DMSO-d 6 ) δ=8.2 (s, 6H), 7.95 (d, j= 7.2,8H), 7.94 (d, j= 7.2,8H), 7.89-7.79 (m, 40H), 0.66 (s, 6H); MS (ESI) m/z= 468.45, calculated C 87 H 68 F 3 O 3 S 5 Si 3+ m/z＝468.45([M] 3+ ) The method comprises the steps of carrying out a first treatment on the surface of the m/z= 148.95, calculated CF 3 SO 3 - m/z＝148.95([M] - )。
Example 9
The compound IV-5 was prepared as follows:
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into a 200mL Schleck flask was charged bis (3, 5-dibromophenyl) -diphenylsilane (6 g,9mmol,1.0 eq), 3-methylthiophenylboronic acid (4.5 g,27mmol,3 eq) and 80mL tetrahydrofuran. Anhydrous potassium carbonate solid (6.2 g,45mmol,5 eq) was weighed, dissolved in 30mL of water and added to the reaction flask. The system was deoxygenated three times under nitrogen atmosphere. Then tetrakis (triphenylphosphine) palladium catalyst (208 mg,0.18mmol,0.02 eq) was added under nitrogen and heated to reflux for 5h. 3-Methylphenylboronic acid (1.2 g,9mmol,1 eq) was added under nitrogen and the reaction continued under reflux for 5h. The reaction solution was cooled to room temperature, extracted with dichloromethane/water, and the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography (developing solvent V Dichloro/petroleum ether =1/1), a white solid 6.4 was finally obtained in 90% yield. 1 H NMR(400MHz,CDCl 3 ) δ=7.82 (s, 6H), 7.69 (d, j= 7.8,4H), 7.50-7.41 (m, 8H), 7.41 (s, 3H), 7.33 (d, j= 5.0,6H), 7.22-7.24 (m, 3H), 7.18 (s, 1H), 2.46 (s, 3H), 2.45 (s, 9H); MS (ESI) m/z= 815.2267, calculated C 52 H 44 S 3 SiNa + m/z＝815.2267([M+Na] + )。
Example 10
The compound I-5 was prepared as follows:
the specific procedure was as in example 2, except that IV-1 was replaced with IV-5, with a reaction yield of 85%. 1 H NMR(400MHz,CD 3 CN) δ8.19 (s, 6H), 8.02 (d, j=7.7hz, 3H), 7.98 (s, 3H), 7.9 (d, j=7.6hz, 3H), 7.76 (dd, j= 7.7,3H), 7.75 (d, j= 7.2,4H), 7.60-7.47 (m, 7H), 7.41 (s, 1H), 7.18 (s, 1H), 3.17 (s, 18H), 2.46 (s, 3H); MS (ESI) m/z= 279.1021, calculated C 55 H 53 S 3 Si 3+ m/z＝279.1020([M] 3+ ) The method comprises the steps of carrying out a first treatment on the surface of the m/z= 148.95, calculated CF 3 SO 3 - m/z＝148.95([M] - )。
Example 11
The compound IV-6 was prepared as follows:
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the specific procedure was as in example 5, except that 3, 4-dimethoxyphenylboronic acid was replaced with 4-methylphenylboronic acid and the reaction yield was 85%. 1 H NMR(400MHz,CDCl 3 ) δ=7.78 (s, 2H), 7.76 (s, 4H), 7.60 (d, j= 7.6,4H), 7.43 (d, j= 6.7,8H), 7.27 (d, j= 7.6,4H), 7.24 (d, j= 6.7,8H), 2.48 (s, 6H); MS (ESI) m/z= 811.29, calculated C 54 H 48 S 2 SiNa + m/z＝811.29([M+Na] + )。
Example 12
The compound I-6 was prepared as follows:
the specific procedure was as in example 2, except that IV-1 was replaced with IV-6, with a reaction yield of 85%. 1 H NMR (400 mhz, cdcn) δ=8.04 (s, 2H), 7.98 (s, 4H), 7.49 (d, j= 8.2,8H), 7.46 (d, j= 7.6,4H), 7.43 (d, j= 7.6,4H), 7.30 (d, j= 8.0,8H), 3.15 (s, 12H), 2.34 (s, 12H); MS (ESI) m/z= 967.29, calculated C 57 H 54 F 3 O 3 S 3 Si + m/z＝967.29([M] + ) The method comprises the steps of carrying out a first treatment on the surface of the m/z= 148.95, calculated CF 3 SO 3 - m/z＝148.95([M] - )。
Example 13
The compound IV-7 was prepared as follows:
the specific procedure was as in example 1, except that III-1 was replaced with III-7 in 85% yield. 1 H NMR(400MHz,CDCl 3 )δ＝7.82(s,6H),7.71(d,J＝6.8Hz,2H),7.61(d,J＝6.7Hz,2H),7.48–7.37(m,15H),7.27(d,J＝8.7Hz,2H) 7.22-7.24 (m, 4H), 2.45 (s, 15H); MS (ESI) m/z= 893.19, calculated C 53 H 46 S 5 SiNa + m/z＝893.19([M+Na] + )。
Example 14
The compound I-7 was prepared as follows:
the specific procedure was as in example 2, except that IV-1 was replaced with IV-7 in 85% yield. 1 H NMR(400MHz,CD 3 CN) δ8.19 (s, 6H), 8.02 (d, j=7.7 hz, 4H), 7.98 (s, 4H), 7.93 (d, j=7.6 hz, 2H), 7.9 (d, j=7.6 hz, 4H), 7.88 (d, j=7.6 hz, 2H), 7.76 (dd, j= 7.7,4H), 7.61 (d, j=6.1 hz, 2H), 7.55-7.45 (m, 3H), 3.17 (s, 30H); MS (ESI) m/z= 414.41, calculated C 60 H 61 F 6 O 6 S 7 Si 3+ m/z＝414.41([M] 3+ ) The method comprises the steps of carrying out a first treatment on the surface of the m/z= 148.95, calculated CF 3 SO 3 - m/z＝148.95([M] - )。
Example 15
The thermal stability and the glass transition temperature of the compounds prepared in example 2 and example 4 were measured, the differential scanning calorimetry curve and the thermogravimetric analysis of the compound of example 2 are shown in fig. 1, the differential scanning calorimetry curve and the thermogravimetric analysis of the compound of example 4 are shown in fig. 2, and the results show that the glass transition temperature of both compounds reaches more than 230 ℃, and the compounds have good thermal stability.
Example 16
The compound I-1 of example 2 was dissolved in acetonitrile to prepare a 20mg/mL solution, which was filtered through a microporous filter having a pore size of 0.2. Mu.m, to obtain a spin-coating solution, which was spin-coated on an untreated silicon substrate to prepare a film, and the uniformity of the film was analyzed by scanning electron microscope SEM and atomic force microscope AFM, respectively, and the results are shown in FIGS. 3 and 4. In fig. 3, there is no color and shade gap, indicating that the films are in the same horizontal plane and there is no height difference. Fig. 4 shows that the film has no significant height difference, and the film surface Roughness (RMS) is only 0.5nm, indicating that the film surface is very flat. It can be seen that the films produced are very uniform.
Example 17
Negative photoresist formulation and photolithography using the same: the compound I-1 of example 2 was dissolved in acetonitrile to prepare a solution having a mass concentration of 20mg/mL, and the solution was filtered through a microporous filter having a pore diameter of 0.2. Mu.m, to obtain a spin-coating solution, spin-coating a film on an untreated silicon substrate, and pre-baking at 80℃for 3 minutes, and the film thickness was measured using an ellipsometer. The prepared film is subjected to exposure experiments by using an electron beam light source of a national nano center, the exposure period is 60nm,50nm and 44nm, and very uniform photoetching stripes can be obtained, and the test result is shown in figure 5. The results show that the lithographic fringes were 35, 25 and 22nm wide, with high resolution and low line edge roughness (LER < 2), respectively.
The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. A compound of formula (I):
wherein,
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 identical or different, each independently selected from-S + R S1 R S2 、-O-C 1-15 alkyl-C 6-20 aryl-S + R S1 R S2 Or a group Z which is H, unsubstituted or optionally substituted by one, twoOr more R A Substituted as follows: c (C) 1-15 Alkyl, C 1-15 Alkoxy, C 3-20 Cycloalkyl, C 6-20 Aryl, 5-20 membered heteroaryl, 3-20 membered heterocyclyl, -C 1-15 alkyl-C 6-20 Aryl, -C 1-15 Alkyl-5-20 membered heteroaryl, -C 1-15 alkyl-CO-C 6-20 Aryl, -C 1-15 alkyl-CO-5-20 membered heteroaryl, -C 1-15 alkyl-CO-C 1-15 Alkyl, -C 1-15 alkyl-CO-C 3-20 Cycloalkyl; r is R 0 Selected from the group consisting of-O-C 1-15 alkyl-C 6-20 aryl-S + R S1 R S2 Or a group Z as described above;
R A selected from = O, NO 2 、C 1-15 Alkyl, C 1-15 Alkoxy, C 3-20 Cycloalkyl, C 6-20 Aryl, 5-20 membered heteroaryl;
R S1 、R S2 identical or different, each independently selected from unsubstituted, or optionally substituted with one, two or more R B Substituted as follows: c (C) 1-15 Alkyl, C 3-20 Cycloalkyl, C 6-20 Aryl, 5-20 membered heteroaryl, deuterated C 1-15 Alkyl, or R S1 、R S2 And S attached thereto form together an unsubstituted or optionally substituted one, two or more R B Substituted 5-8 membered sulfur-containing heterocyclyl; the 5-8 membered sulfur-containing heterocycle optionally further contains 1-2 oxygen or sulfur; the 5-8 membered sulfur-containing heterocycle is optionally further fused with one or two benzene rings;
R B identical or different, independently of one another, from H, oxo (=O), nitro, CN, C 1-15 Alkyl, C 1-15 An alkoxy group;
E 1 、E 2 identical or different, each independently selected from C 1-15 Alkyl, C 3-20 Cycloalkyl, unsubstituted, or optionally substituted with one, two or more sulfonium salt groups-S + R S1 R S2 Substituted as follows: c (C) 6-20 Aryl, 5-20 membered heteroaryl;
X – is an anion, e.g. halide, carboxylate, sulfate,Alkyl sulfonate, haloalkyl sulfonate (such as trifluoromethane sulfonate, perfluoropropyl sulfonate, perfluorobutyl sulfonate), p-toluene sulfonate, anions of sulfonamide, tetrafluoroborate, hexafluoroantimonate, hexafluorophosphate or bis-trifluoromethane sulfonyl imide ions;
n is equal to the sulfonium salt group-S in the molecule + R S1 R S2 S in (2) + Number S of (S) + And X – The compound is made to be electrically neutral as a whole, and n is an integer of 2-6.
2. The compound of claim 1, wherein the compound of formula (I) has 2 to 6 groups-S + R S1 R S2 。
Preferably, the said-S + R S1 R S2 Selected from unsubstituted or optionally substituted by one, two or more R 1 ' substituted following groups:
wherein,representing a connection bond; r is R 1a And R is 1b Identical or different, each independently selected from unsubstituted or substituted by one, two or more R C Substituted as follows: c (C) 1-15 Alkyl, C 3-20 Cycloalkyl, -C 1-15 alkyl-C 6-20 Aryl, -C 1-15 Alkyl-5-20 membered heteroaryl, -C 6-20 aryl-C 1-15 Alkyl, deuterated C 1-15 An alkyl group; r is R C 、R 1 'same or different', independently of each other, selected from =o, nitro, C 1-15 Alkyl, C 1-15 An alkoxy group; m is selected from integers from 0 to 5; y is selected from CH 2 、O、S、C(O)；
Preferably, the radical R 1a And R is 1b One selected from the following structures:
wherein,representing a connection key.
3. A compound according to claim 1 or 2, wherein R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 Identical or different, each independently selected from H, -S + R S1 R S2 、C 1-6 Alkyl, C 1-6 An alkoxy group; r is R S1 、R S2 Selected from C 1-6 Alkyl, C 6-12 An aryl group;
preferably, R 0 Is H, -O-C 1-6 alkyl-C 6-12 aryl-S + R S1 R S2 、C 1-6 Alkyl, C 1-6 Alkoxy, R S1 、R S2 Selected from C 1-6 Alkyl, C 6-12 Aryl groups.
Preferably E 1 、E 2 Is C 1-8 Alkyl, C 6-12 Aryl or quilt-S + R S1 R S2 Substituted C 6-12 Aryl, wherein R is S1 、R S2 Selected from C 1-6 Alkyl, C 6-12 Aryl groups.
4. A compound according to any one of claims 1 to 3, wherein the compound of formula (I) is selected from the group consisting of:
5. a photoresist composition comprising a compound of formula (I) as defined in any one of claims 1 to 4.
6. The photoresist composition of claim 5, wherein the photoresist composition further comprises a solvent, for example, selected from one, two or more of the following: propylene Glycol Methyl Ether Acetate (PGMEA), dimethylformamide (DMF), cyclohexanone, ethyl n-pentanone, ethyl iso-pentanone, ethanol, acetonitrile, isopropanol, acetone, methyl n-pentanone, methyl iso-pentanone.
Preferably, the photoresist composition is a positive or negative photoresist composition.
7. The photoresist composition of claim 5 or 6, wherein the photoresist is a one-component photoresist comprising only the compound of formula (I) except a solvent.
8. A photoresist coating comprising a compound of formula (I) as defined in any one of claims 1 to 4.
9. A method of producing a photoresist coating according to claim 8, wherein the photoresist composition of any one of claims 5 to 7 is applied to a substrate.
10. Use of a compound of formula (I) according to any one of claims 1 to 4, a photoresist composition according to any one of claims 5 to 7, a photoresist coating according to claim 8 in photolithography.
Preferably, the lithography is 248nm lithography, 193nm lithography, extreme Ultraviolet (EUV) lithography, nanoimprint lithography or electron beam lithography.
CN202211035743.3A 2022-08-26 2022-08-26 Single molecule resin based on polysulfide onium salt and photoresist composition thereof Pending CN117659073A (en)

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