Adamantane-based polysulfonium salt monomolecular resin photoresist, and preparation method and application thereof
Patent Information
- Application Number
- CN202211034313.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2022-08-26
- Publication Date
- 2026-09-18
- Estimated Expiration
- 2042-08-26
AI Technical Summary
然而,与迄今报道的CAR数量相比,n-CARs的数量非常有限,尤其是基于单分子树脂的n-CARs
[0059] (1) This invention provides a series of novel polythionium salt-type monomolecular resins based on adamantane, namely the compounds shown in formula (I), which can be used as the host material for photoresists. Their raw materials are inexpensive and readily available, and most of their synthesis processes are simple;
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Figure CN117658880B_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the field of photolithography materials technology, specifically relating to a class of adamantane-based polythionium salt monomolecular resin photoresists, their preparation methods, and applications. Background Technology
[0002] Photoresist, also known as photoresist, is a type of etch-resistant thin film material whose solubility changes after being irradiated by energy sources such as light beams, electron beams, ion beams, or X-rays. It is an indispensable core material in the microelectronics industry for manufacturing large-scale and very large-scale integrated circuits. By coating photoresist onto the surface of semiconductors, conductors, or insulators, the remaining portion after exposure and development protects the underlying substrate. Then, etching with an etchant transfers the desired micro-pattern from the photomask to the substrate. Therefore, photoresist is a key material in device microfabrication technology. The rapid development of the semiconductor industry has placed increasingly higher demands on photolithography technology. From early near-ultraviolet G-line 436nm and I-line 365nm phenolic resin-diazonaphthoquinone photoresists, to deep ultraviolet 248nm and 193nm photoresists, and then to extreme ultraviolet 13.5nm and electron beam photoresists, nanoscale photolithography requires increasingly higher resolution and smaller edge roughness, placing higher demands on the overall performance of photoresist materials. Developing novel photoresists with high resolution, high sensitivity, and low edge roughness to meet the overall performance requirements of photolithography processes, especially the requirements of next-generation photolithography technologies, has become an important aspect of the current development of photolithography technology.
[0003] Photoresist is typically a mixture of a resin substrate, photoacid generators (PAGs), and various trace additives. Currently, conventional high-resolution photoresists employ chemical amplification. "Chemical amplification" refers to the process where photoacid generators (PAGs) decompose upon exposure to light, producing acid. This acid triggers a series of chemical reactions, significantly altering the solubility of the photoresist material in both illuminated and unilluminated areas. Pattern transfer is then achieved through development. However, PAGs and the substrate are often simply physically mixed, resulting in uneven dispersion of PAGs within the substrate. The diffusion rate of the acid generated after light exposure is difficult to control, negatively impacting the edge roughness of the lithographic pattern. Traditional photoresist substrates use polymer resins with molecular weights ranging from 5000 to 15000 Daltons. These polymer resins, due to their large molecular size, molecular weight dispersion, and entangled molecular chains, typically affect the resolution and edge roughness of the lithographic pattern, failing to meet the requirements for finer resolution.
[0004] To address these issues, chemical synthesis is used to control the reduction of the molecular weight of the photoresist substrate resin to a certain size, achieving a single-molecule state and forming monomolecular resins (also known as molecular glasses). This is an important method for achieving high-resolution photolithography. Monomolecular resins retain the film-forming properties and ease of processing inherent in resins, while also possessing a defined molecular structure, making them easy to synthesize and modify. Photoresist materials based on monomolecular resins hold promise for meeting the requirements of high-resolution photolithography. Research on novel non-chemically amplified photoresists (n-CARs) is receiving increasing attention. n-CARs are materials directly sensitive to radiation. Their formulations do not require the addition of PAGs, containing only the substrate material as a component. Therefore, they can effectively solve the compatibility issues between the substrate material and additives, as well as the problem of uneven acid diffusion after exposure, thereby reducing the LER value. However, compared to the number of CARs reported to date, the number of n-CARs is very limited, especially n-CARs based on monomolecular resins. Summary of the Invention
[0005] To address the aforementioned problems, this invention provides a polythionium salt monomolecular resin based on adamantane, which can be used as a host material for non-chemically amplified photoresists.
[0006] The technical solution of the present invention is as follows:
[0007] A compound represented by formula (I):
[0008]
[0009] in,
[0010] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 Whether the same or different, each is independently selected from -S + R S1 R S2 -OC 1-15 Alkyl-C 6-20 Aryl-S + R S1 R S2 or group Z, wherein group Z is H, unsubstituted, or optionally substituted with one, two, or more R groups. A The following groups are substituted: C 1-15Alkyl, C 1-15 Alkoxy, C 3-20 cycloalkyl, C 6-20 Aryl, 5-20 membered heteroaryl, 3-20 membered heterocyclic, -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;
[0011] R is selected from -OC 1-15 Alkyl-C 6-20 Aryl-S + R S1 R S2 Or, as described above, group Z;
[0012] R A Selected from =O, NO2, C 1-15 Alkyl, C 1-15 Alkoxy, C 3-20 cycloalkyl, C 6-20 Aryl, 5-20 heteroaryl;
[0013] R S1 R S2 Whether identical or different, each is independently selected from unsubstituted or arbitrarily selected by one, two or more R B The following groups are substituted: C 1-15 Alkyl, C 3-20 cycloalkyl, C 6-20 Aryl, -C 1-15 Alkyl-C 6-20 Aryl, 5-20 heteroaryl, deuterated C 1-15 Alkyl groups (such as deuterated methyl groups), or R S1 R S2 Together with the S connected thereto, they form an unsubstituted or optionally substituted group of one, two or more R groups. B The substituted 5-8 member sulfur-containing heterocyclic group; the 5-8 member sulfur-containing heterocyclic group optionally further contains 1-2 oxygen or sulfur atoms; the 5-8 member sulfur-containing heterocyclic group is also optionally fused with one or two benzene rings;
[0014] R B They may be the same or different, and are independently selected from H, oxo (=O), nitro, CN, and C. 1-15 Alkyl, C 1-15 Alkoxy;
[0015] X – It is an anion, such as halide ions, carboxylate ions, sulfate ions, alkyl sulfonates, haloalkyl sulfonates (such as trifluoromethanesulfonate, perfluoropropyl sulfonate, perfluorobutyl sulfonate), p-toluenesulfonate, anions of sulfonamides, tetrafluoroborate, hexafluoroantimonate, hexafluorophosphate, or bis(trifluoromethanesulfonyl)imide ions.
[0016] n equals the thionium salt group -S in the molecule. + R S1 R S2 S + The number of S + and X – To make the compound as a whole electrically neutral, n has an integer value of 2-6; that is, the compound of formula (I) has 2-6 -S groups. + R S1 R S2 .
[0017] In some embodiments of the present invention, the compound of formula (I) has 2-6 -S groups. + R S1 R S2 For example, having 2, 3, 4, 5, or 6 thioonium salt groups -S + R S1 R S2 .
[0018] In some embodiments of the present invention, R1-R 20 It contains 4 thioonium salt groups -S + R S1 R S2 And each phenyl group has one thionium salt group -S + R S1 R S2 .
[0019] In some embodiments of the present invention, both R are thionium salt groups -S. + R S1 R S2 And R1-R 20 It contains 4 thioonium salt groups -S + R S1 R S2 .
[0020] In some embodiments of the present invention, the thionium salt group -S + R S1 R S2 It is located adjacent, intermediate, or opposite.
[0021] According to an embodiment of the present invention, the thionium salt group -S+ R S1 R S2 Selected from the following groups that are unsubstituted or optionally substituted by one, two or more R1':
[0022]
[0023] in, Indicates a connection key; R 1a and R 1b They can be the same or different, each independently selected from no substitution, or by one, two or more R... C The following groups are substituted: 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 Alkyl; R C R1' may be the same or different, and are independently selected from =O, nitro, C 1-15 Alkyl, C 1-15 Alkyl group; m is selected from integers from 0 to 5; Y is selected from CH2, O, S, C(O);
[0024] Preferably, the group R 1a and R 1b Choose one of the following structures:
[0025]
[0026] in, Indicates a connection key.
[0027] In some embodiments of the present invention, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 Whether the two are the same or different, they are each independently selected from H or -S. + R S1 R S2 ;R S1 R S2 Whether the two are the same or different, each is independently selected from C. 1-6 Alkyl, -C6-12 Aryl, -C 1-6 Alkyl-C 6-12 Aryl;
[0028] R is C 1-6 Alkyl group.
[0029] In some preferred embodiments of the present invention, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 Whether they are the same or different, they are each independently selected from H and -S. + (C 1-6 Alkyl)2, -S + (C 6-12 Aryl)2, -S + (-C 1-6 Alkyl-C 6-12 Aryl)(C 1-6 alkyl);
[0030] R can be methoxy, ethoxy, propoxy, or butoxy.
[0031] In some embodiments of the present invention, the compound shown in formula (I) has a symmetrical structure, that is, the structures on the four benzene rings on the top, bottom, left, and right are completely identical.
[0032] As an example, the compound of formula (I) has the following structure:
[0033]
[0034]
[0035] Optionally, the compound shown in formula (I) can also undergo ion exchange with the corresponding anion solution to obtain compounds of formula (I) with different anions.
[0036] The present invention also provides a method for preparing the compound shown in formula (I), comprising the following method:
[0037] a. Mixing compound II with R S1 -L and MX are mixed and reacted to give compound (I);
[0038]
[0039] Among them, R0', R1', R2', R3', R4', R5', R6', R7', R8', R9', R 10 '、R 11 '、R 12 '、R 13 '、R 14 '、R 15 '、R 16 '、R 17 '、R 18 '、R 19 '、R 20 'is the group Z or -SR as described above. S2 ;
[0040] L is a leaving group, such as halogen; R and X have the above definitions, while MX is the metal salt of X, and M is selected from silver;
[0041] Alternatively, b. Compound II' is mixed with diphenyl sulfoxide and trifluoromethanesulfonic anhydride to react and obtain compound (I);
[0042]
[0043] R has the above definition.
[0044] The present invention also provides the use of the compound represented by formula (I) above for the preparation of photoresists.
[0045] According to an embodiment of the present invention, the photoresist is a single-component photoresist, containing only the compound shown in formula (I) in addition to the solvent.
[0046] The present invention also provides a photoresist composition comprising the compound shown in formula (I).
[0047] According to an embodiment of the present invention, the photoresist solvent is selected from one, two or more of the following substances: propylene glycol methyl ether acetate (PGMEA), N,N-dimethylformamide, dimethylformamide (DMF), cyclohexanone, ethyl n-pentanone, ethyl isopentanone, ethanol, acetonitrile, isopropanol, acetone, methyl n-pentanone, and methyl isopentanone.
[0048] According to an embodiment of the present invention, the photoresist composition is a positive or negative photoresist composition, comprising the compound shown in formula (I) and a photoresist solvent.
[0049] In one embodiment, the photoresist composition is a single-component photoresist, which consists of a compound of formula (I) and a photoresist solvent. That is, the photoresist composition contains only one component, namely the compound of formula (I), in addition to the photoresist solvent.
[0050] The present invention also provides a photoresist coating comprising the compound shown in formula (I).
[0051] The present invention also provides a method for preparing the above-mentioned photoresist coating, comprising: applying the above-mentioned photoresist composition onto a substrate to obtain the coating.
[0052] Preferably, the application method is spin coating.
[0053] Preferably, the substrate is, for example, a silicon wafer substrate.
[0054] Preferably, the photoresist coating is a thin film.
[0055] The present invention also provides the application of the photoresist coating in photolithography.
[0056] The compound described in this invention has a high glass transition temperature (greater than 150°C) due to its unique polythionium salt structure, and can be used for photolithography.
[0057] According to the present invention, the photoresist coating can be used in modern photolithography technologies such as 248nm photolithography, 193nm photolithography, extreme ultraviolet (EUV) photolithography, nanoimprint lithography or electron beam lithography, and is preferably used in extreme ultraviolet and electron beam lithography technologies.
[0058] The beneficial effects of this invention are as follows:
[0059] (1) This invention provides a series of novel polythionium salt-type monomolecular resins based on adamantane, namely the compounds shown in formula (I), which can be used as the host material for photoresists. Their raw materials are inexpensive and readily available, and most of their synthesis processes are simple;
[0060] (2) This type of monomolecular resin has good solubility in various polar solvents and can be used to prepare good thin films by spin coating, which is suitable for the requirements of photolithography. The compound shown in formula (I) can be used as a single-component non-chemical amplification photoresist, avoiding the problems of uneven distribution of acid-generating agents and anti-acid diffusion agents and uneven acid diffusion in chemical amplification photoresists. The resulting pattern has high resolution and low line edge roughness.
[0061] (3) The compound of the present invention uses adamantane and benzene ring as basic units, which maximizes the etching resistance of the main material, while improving its thermal stability, solubility and film-forming properties, and greatly improves its overall performance. The thermal decomposition temperature of the main material is greater than 170°C, which expands the application range of the material and is suitable for the requirements of photolithography process.
[0062] (4) The adamantane-based polythionium salt monomolecular resin of the present invention has a definite molecular structure and a single molecular size, which can well meet the requirements of high-resolution photolithography.
[0063] Terms and Definitions
[0064] Unless otherwise defined, all technical terms herein have the same meaning as commonly understood by one of ordinary skill in the art to which the subject matter of the claims pertains.
[0065] "More than three" means three or more.
[0066] Term "C" 1-15 "Alkyl" should be understood as referring to a straight-chain or branched saturated monovalent hydrocarbon group having 1 to 15 carbon atoms. For example, "C 1-6 "Alkyl" means a straight-chain or branched alkyl group 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-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, neopentyl, 1,1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl, or 1,2-dimethylbutyl, or their isomers.
[0067] Term "C" 1-15 "Alkoxy" should be understood as -OC 1-15 Alkyl, wherein C 1-15 Alkyl groups have the above definition.
[0068] Term "C" 3-20 "Cycloalkyl" should be understood as representing a saturated monovalent monocyclic, bicyclic, or polycyclic hydrocarbon ring (also called a fused ring hydrocarbon ring) with 3-20 carbon atoms. Bicyclic or polycyclic cycloalkyl includes fused cycloalkyl, bridged cycloalkyl, and spirocyclic cycloalkyl; fused ring refers to a fused ring structure formed by two or more cyclic structures sharing two adjacent ring atoms (i.e., sharing a bond). Bridged ring refers to a fused ring structure formed by two or more cyclic structures sharing two non-adjacent ring atoms. Spirocyclic refers to a fused ring structure formed by two or more cyclic structures sharing a single ring atom. For example, the C 3-20 Cycloalkyl groups can be C 3-8 Monocyclic cycloalkyl groups, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, or C 7-12 Circoalkyl groups, such as decahydronaphthalene rings; or C... 7-12 Bridged cycloalkyl groups, such as norbornene, adamantane, and bicyclo[2,2,2]octane.
[0069] The term "3-20 membered heterocyclic group" refers to a saturated or unsaturated monovalent monocyclic or bicyclic hydrocarbon ring containing 1-5 heteroatoms independently selected from N, O, and S, preferably a "3-10 membered heterocyclic group". The term "3-10 membered heterocyclic group" also refers to a saturated monovalent monocyclic or bicyclic hydrocarbon ring containing 1-5, preferably 1-3, heteroatoms selected from N, O, and S. The heterocyclic group can be connected to the rest of the molecule via any one of the carbon atoms or a nitrogen atom (if present). Specifically, the heterocyclic group can include, but is not limited to: 4-membered rings, such as azirmonobutyl or oxobutyl; 5-membered rings, such as tetrahydrofuranyl, dioxacyclopentenyl, pyrrolyl, imidazoyl, pyrazolyl, or pyrrololinyl; or 6-membered rings, such as tetrahydropyranyl, piperidinyl, morpholinyl, dithiaalkyl, thiomorpholinyl, piperazinyl, or trithiaalkyl; or 7-membered rings, such as diazacycloheptyl. Optionally, the heterocyclic group may be benzo-fused. The heterocyclic group may be bicyclic, for example, but not limited to, a 5,5-membered ring, such as a hexahydrocyclopenta[c]pyrrole-2(1H)-yl ring, or a 5,6-membered bicyclic ring, such as a hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl ring. The nitrogen-containing ring may be partially unsaturated, i.e., it may contain one, two, or more double bonds, for example, but not limited to, 2,5-dihydro-1H-pyrrole, 4H-[1,3,4]thiadiazinyl, 4,5-dihydrooxazolyl, or 4H-[1,4]thiazinyl, or it may be benzo-fused, for example, but not limited to, dihydroisoquinolinyl, 1,3-benzooxazolyl, or 1,3-benzodioxacyclopentenyl. According to the invention, the heterocyclic group is non-aromatic.
[0070] Term "C" 6-20 "Aryl" should be understood as representing a monocyclic, bicyclic, or tricyclic hydrocarbon ring with 6 to 20 carbon atoms, exhibiting monovalent aromaticity or partial aromaticity, preferably "C". 6-14 Aryl. The term "C" 6-14 "Aryl" should be understood to preferably represent a monovalent aromatic or partially aromatic monocyclic, bicyclic, or tricyclic hydrocarbon ring ("C") having 6, 7, 8, 9, 10, 11, 12, 13, or 14 carbon atoms. 6-14 Aryl), particularly a ring with 6 carbon atoms (“C6 aryl”), such as phenyl; or biphenyl, or a ring with 9 carbon atoms (“C9 aryl”), such as indenyl or indenyl, or a ring with 10 carbon atoms (“C9 aryl”). 10 Aryl groups, such as tetrahydronaphthyl, dihydronaphthyl, or naphthyl, or rings with 13 carbon atoms (“C”). 13 Aryl groups, such as fluorene groups, or rings with 14 carbon atoms (“C”). 14 Aryl), for example, anthracene. When the C 6-20When the aryl group is substituted, it can be monosubstituted or polysubstituted. Furthermore, there are no restrictions on the substitution site; for example, it can be ortho, para, or meta substituted.
[0071] The term "5-20-membered heteroaryl" should be understood to include 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" should also be understood to include monovalent monocyclic, bicyclic, or tricyclic aromatic ring systems having 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14 ring atoms, particularly 5, 6, 9, or 10 carbon atoms, and containing 1 to 5, preferably 1 to 3, heteroatoms independently selected from N, O, and S, and in each case, may be benzofused. Specifically, the heteroaryl group is selected from thienyl, furanyl, pyrroleyl, oxazolyl, thiazolyl, imidazoleyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, thia-4H-pyrazolyl, and their benzo[derivatives], such as benzofuranyl, benzothienyl, benzooxazolyl, benzoisooxazolyl, benzoimidazolyl, benzotriazolyl, indazole, indolyl, isindolyl, etc.; or pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and their benzo[derivatives], such as quinolinyl, quinazolinyl, isoquinolinyl, etc.; or acrylinyl, inazinyl, purinyl, and their benzo[derivatives]; or terpenolyl, phthalazinyl, quinazolinyl, quinoxolinyl, naphridinyl, pteridinyl, carbazolyl, acridineyl, phenazinyl, phenothiazinyl, phenothiazinyl, etc.
[0072] The term "C" above 1-15 The definition of "alkyl" also applies to other C-containing compounds. 1-15 Alkyl groups, such as -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, etc.
[0073] Similarly, C 6-20 Aryl, 5-20 heteroaryl, C 3-20 The cycloalkyl group has the same definition throughout the text. Attached Figure Description
[0074] Figure 1The differential scanning calorimetry (DSC) curve and thermogravimetric curve are shown for compound I-1 in Example 1 of this invention.
[0075] Figure 2 The differential scanning calorimetry (DSC) curve and thermogravimetric curve are shown for compound I-3 in Example 3 of this invention.
[0076] Figure 3 This is an atomic force microscope (AFM) image of compound I-1 in Example 1 of the present invention.
[0077] Figure 4 This is a scanning electron microscope (SEM) image of the photolithographic stripes (exposure period of 100 nm) of the negative resist film of compound I-1 as the host material in Example 1 of the present invention.
[0078] Figure 5 This is a scanning electron microscope (SEM) image of the photolithographic stripes (exposure period of 80 nm) of the negative resist film of compound I-1 as the host material in Example 1 of the present invention.
[0079] Figure 6 This is a scanning electron microscope (SEM) image of the photolithographic stripes (exposure period of 60 nm) of the negative resist film of compound I-1 as the host material in Example 1 of the present invention.
[0080] Figure 7 This is a scanning electron microscope (SEM) image of the photolithographic stripes (exposure period of 80 nm) of the negative resist film of compound I-2 as the host material in Example 2 of the present invention.
[0081] Figure 8 This is a scanning electron microscope (SEM) image of the photolithographic stripes (exposure period of 60 nm) of the negative resist film of compound I-5 as the host material in Example 5 of the present invention.
[0082] Figure 9 This is a scanning electron microscope (SEM) image of the photolithographic stripes (exposure period of 50 nm) of the negative resist film of compound I-7 as the host material in Example 7 of the present invention. Detailed Implementation
[0083] The technical solution of the present invention will be further described in detail below with reference to specific embodiments. It should be understood that the following embodiments are merely illustrative and explanatory of the present invention, and should not be construed as limiting the scope of protection of the present invention. All technologies implemented based on the above content of the present invention are covered within the scope of protection intended by the present invention.
[0084] Unless otherwise stated, the raw materials and reagents used in the following examples are commercially available products or can be prepared by known methods.
[0085] Example 1
[0086] The synthetic route for preparing compound V-1 is as follows:
[0087]
[0088] Experimental Procedure: A 250 mL three-necked reaction flask was purged with nitrogen at one end and connected to a tail gas absorption device at the other. 1,3-Dibromoadamantane (8.89 g, 30 mmol, 1 eq), 2,6-dibromophenol (19 g, 75 mmol, 2.5 eq), and 30 mL of dry 1,2-dichloroethane were added. The reaction was placed in an ice bath under nitrogen purging. Under nitrogen atmosphere, aluminum trichloride catalyst (1.32 g, 9.9 mmol, 0.33 eq) was added, and the reaction mixture was kept in an ice bath for 5 h. After the reaction was complete, the system was a brick-red turbid liquid. The reaction was quenched with 2 M hydrochloric acid solution, and the crude product was obtained by filtration. The crude product was extracted with dichloromethane / water, the organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was removed by vacuum distillation. Petroleum ether was added, and the mixture was sonicated to dissolve excess phenol. The dissolved solid was dried to obtain a white solid with a yield of 80%. 1 ¹H NMR (400 MHz, deuterated chloroform) δ 7.42 (s, 4H), 5.75 (s, 2H), 2.32 (2H, s), 2.17 (2H, s), 2.04 (8H, q, J 11.6, 10.9), 1.83 (2H, s); MS (ESI): m / z = 636.02, calculated C 22 H 20 Br4O2 + m / z = 636.02 ([M]) + ).
[0089] The synthetic route for preparing compound IV-1 is as follows:
[0090]
[0091] Experimental Procedure: Compound V-1 (8 g, 12.6 mmol, 1.0 eq) and 80 ml of acetone were added to a 250 ml Schlenk flask. After stirring and heating to 60 °C until completely dissolved, potassium carbonate (6.95 g, 50.3 mmol, 4.0 eq) was added. Iodobutane (9.26 g, 50.3 mmol, 4.0 eq) was added dropwise to the reaction flask using a syringe. After the addition was complete, the reaction was carried out at 60 °C for 22 hours. Heating was stopped, the solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane / water. The organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was removed by vacuum distillation. The product remained oily after evaporation. Approximately 20 ml of methanol was added to the crude product, and after sonication, a white precipitate formed. Vacuum distillation yielded a white solid with a yield of 93%. 1¹H NMR (400MHz, deuterated chloroform) δ 7.41 (4H, s), 3.14 (4H, t, J 6.1), 2.33 (2H, s), 2.17 (2H, s), 2.04 (8H, q, J 11.6, 10.9), 1.83 (2H, s), 1.14 (4H, m), 0.95 (4H, h, J 7.4), 0.54 (6H, t, J 7.4). MS (ESI): m / z = 747.94, calculated C 30 H 36 Br4O2 + m / z = 747.94 ([M]) + ).
[0092] The synthetic route for preparing compound II-1 is as follows:
[0093]
[0094] Experimental Procedure: Compound IV-1 (5 g, 6.82 mmol, 1.0 eq), 4-methylthiophenylboronic acid (5.73 g, 34.1 mmol, 5.0 eq), and 20 ml of dioxane were added to a 250 ml Schlenk reaction flask. The mixture was heated and stirred until completely dissolved at 50 °C. Anhydrous potassium carbonate (4.71 g, 40.9 mmol, 6.0 eq) was dissolved in 6 ml of deionized water and added to the reaction flask, and stirred until homogeneous. The mixture was evacuated and purged with nitrogen three times. Tetra(triphenylphosphine)palladium catalyst (197 mg, 0.17 mmol, 0.025 eq) was added under a nitrogen atmosphere, and the mixture was heated under reflux for 10 h. After cooling to room temperature, the solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane / water. The organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was removed by vacuum distillation to obtain a yellowish-brown oil. The product was dissolved in a small amount of dichloromethane. Separation was performed by column chromatography to obtain a white solid in 69% yield. 1 ¹H NMR (600MHz, dichloromethane-d²): δ 7.54 (8H, d, J 8.4), 7.30 (¹²H, m), 3.19 (4H, t, J 6.3), 2.51 (¹²H, s), 2.33 (2H, s), 2.09 (2H, s), 2.01 (8H, q, J 11.7, 10.7), 1.80 (2H, s), 1.16 (4H, m), 1.01 (4H, h, J 7.5), 0.59 (6H, t, J 7.4); MS (MALDI): m / z = 920.38, calculated C 58 H 63 O2S4 + m / z = 920.38 ([M]) + ).
[0095] The synthetic route for preparing compound I-1 is as follows:
[0096]
[0097] Experimental Procedure: Compound II-1 (2.9 g, 3.15 mmol, 1.0 eq), silver trifluoromethanesulfonate (4.85 g, 18.9 mmol, 6.0 eq), and 45 mL of dry dichloromethane were added to a 50 mL single-necked reaction flask. Iodomethane (2.68 g, 18.9 mmol, 6.0 eq) was dissolved in 5 mL of dichloromethane and added slowly dropwise. After the addition was complete, the reaction mixture was allowed to stand at room temperature for 3 h in the dark. The reaction mixture was allowed to stand, and the supernatant was discarded. The solid was dissolved in acetonitrile. The AgI precipitate in the reaction mixture was removed by filtration, yielding a colorless solution. The solvent was removed by vacuum distillation to obtain a white, foamy solid. Recrystallization was performed using methanol as the recrystallization solvent to obtain a white powdery solid in 66% yield. 1 ¹H NMR (600MHz, acetonitrile-d³) δ 7.97 (¹⁶H, m), 7.51 (⁴H, s), 3.18 (⁴⁴H, s), 3.14 (⁴H, t, J 6.1), 2.33 (⁴H, s), 2.17 (⁴H, s), 2.04 (⁸H, q, J 11.6, 10.9), 1.83 (⁴H, s), 1.14 (⁴H, m), 0.95 (⁴H, h, J 7.4), 0.54 (⁶H, t, J 7.4); MS (ESI): m / z = 639.18, calculated C 64 H 76 O8S6 F6 2+ m / z = 639.18 ([M]) 2+ m / z = 148.95, calculated value CF3SO3 - m / z = 148.95 ([M]) - ).
[0098] Example 2
[0099] The synthetic route for preparing compound IV-2 is as follows:
[0100]
[0101] The specific steps are the same as the preparation process of IV-1 in Example 1, except that iodobutane is replaced with iodomethane, and the reaction yield is 98%. 1 ¹H NMR (400MHz, deuterated chloroform) δ 7.41 (4H, s), 3.87 (6H, s), 2.34 (2H, s), 2.17 (2H, s), 2.04 (8H, q, J 11.6, 10.9), 1.83 (2H, s). MS (ESI): m / z = 663.85, calculated C 24 H 24 Br4O2+ m / z = 663.85 ([M]) + ).
[0102] The synthetic route for preparing compound II-2 is as follows:
[0103]
[0104] The specific steps are the same as the preparation process of II-1 in Example 1, except that IV-1 is replaced with IV-2, and the reaction yield is 75%. 1 ¹H NMR (400MHz, deuterated chloroform) δ 7.51 (8H, d, J 7.3), 7.41 (4H, s), 4.16 (6H, s), 2.50 (12H, s), 2.30 (2H, s), 2.00 (10H, m), 1.75 (2H, s). MS (MALDI): m / z = 836.29, calculated C 52 H 52 O2S4 + m / z = 836.29 ([M]) + ).
[0105] The synthetic route for preparing compound I-2 is as follows:
[0106]
[0107] The specific steps are the same as the preparation process of I-1 in Example 1, except that II-1 is replaced with II-2, and the reaction yield is 75%. 1 ¹H NMR (600MHz, acetonitrile-d³) δ 7.97 (¹⁶H, m), 7.51 (⁴H, s), 3.88 (⁶H, s), 3.18 (⁂⁴H, s), 2.33 (⁂H, s), 2.17 (⁂H, s), 2.04 (⁸H, q, J 11.6, 10.9), 1.83 (⁂H, s); MS (ESI): m / z = 597.74, calculated C 58 H 64 O8S6F6 2+ m / z = 597.74 ([M]) 2+ m / z = 148.95, calculated value CF3SO3 - m / z = 148.95 ([M]) - ).
[0108] Example 3
[0109] The synthetic route for preparing compound II-3 is as follows:
[0110]
[0111] The specific steps are the same as the preparation process of II-1 in Example 1, except that 4-methylthiophenylboronic acid is replaced with 3-methylthiophenylboronic acid, and the reaction yield is 63%. 1 ¹H NMR (600MHz, dichloromethane-d²) δ 7.50 (4H, s), 7.34 (¹²H, m), 7.23 (4H, d, J 7.4), 3.21 (4H, t, J 6.2), 2.51 (¹²H, s), 2.34 (2H, s), 2.10 (2H, s), 2.02 (8H, q, J 11.4), 1.81 (2H, s), 1.16 (4H, m), 1.01 (4H, dt, J 14.5, 7.4), 0.59 (6H, t, J 7.4); MS (MALDI): m / z = 920.38, calculated C 58 H 63 O2S4 + m / z = 920.38 ([M]) + ).
[0112] The synthetic route for preparing compound I-3 is as follows:
[0113]
[0114] The specific steps are the same as in Example 1, except that II-1 is replaced with II-3, and the reaction yield is 88%. 1 ¹H NMR (600MHz, acetonitrile-d³) δ 8.18 (4H, s), 8.04 (4H, d, J 7.8), 7.90 (4H, s), 7.78 (4H, s), 7.55 (4H, s), 3.19 (24H, s), 3.13 (4H, t, J 6.3), 2.35 (2H, s), 2.19 (2H, s), 2.08 (8H, q, J 12.3), 1.85 (2H, s), 1.08 (4H, m), 0.92 (4H, m), 0.53 (6H, t, J 7.4); MS (ESI): m / z = 639.18, calculated C 64 H 76 O8S6 F6 2+ m / z = 639.18 ([M]) 2+ m / z = 148.95, calculated value CF3SO3 - m / z = 148.95 ([M]) - ).
[0115] Example 4
[0116] The synthetic route for preparing compound II-4 is as follows:
[0117]
[0118] The specific steps are the same as the preparation process in step II-1 of Example 1, except that 4-methylthiophenylboronic acid is replaced with 3-methylthiophenylboronic acid, and IV-1 is replaced with IV-2, with a reaction yield of 72%. 1 ¹H NMR (400MHz, deuterated chloroform) δ 8.18 (4H, s), 8.04 (4H, d, J 7.8), 7.90 (4H, s), 7.78 (4H, s), 7.55 (4H, s), 3.90 (6H, s), 2.45 (¹²H, s), 2.33 (²H, s), 2.17 (²H, s), 2.04 (8H, q, J 11.6, 10.9), 1.83 (²H, s); MS (MALDI): m / z = 836.29, calculated C 52 H 52 O2S4 + m / z = 836.29 ([M]) + ).
[0119] The synthetic route for preparing compound I-4 is as follows:
[0120]
[0121] The specific steps are the same as the preparation process of I-1 in Example 1, except that II-1 is replaced with II-4, and the reaction yield is 85%. 1 ¹H NMR (600MHz, acetonitrile-d³) δ 8.18 (4H, s), 8.04 (4H, d, J 7.8), 7.90 (4H, s), 7.78 (4H, s), 7.55 (4H, s), 3.90 (6H, s), 3.19 (24H, s), 2.35 (2H, s), 2.19 (2H, s), 2.08 (8H, q, J 12.3), 1.85 (2H, s); MS (ESI): m / z = 597.74, calculated C 58 H 64 O8S6F6 2+ m / z = 597.74 ([M]) 2+ m / z = 148.95, calculated value CF3SO3 - m / z = 148.95 ([M]) - ).
[0122] Example 5
[0123] The synthetic route for preparing compound III-1 is as follows:
[0124]
[0125] The specific steps are the same as the preparation process of II-1 in Example 1, except that 4-methylthiophenylboronic acid is replaced with phenylboronic acid, and the reaction yield is 90%. 1 ¹H NMR (400MHz, deuterated DMSO) δ 8.0 (s, 4H), 7.57 (d, J 7.3, 8H), 7.48–7.39 (m, 12H), 3.18 (t, J 6.0, 4H), 1.04 (tt, J 6.5, 6.4, 4H), 0.86 (qt, J 7.2, 7.2, 4H), 0.45 (t, J 7.3, 6H); MS (MALDI): m / z = 736.43, calculated C 54 H 56 O2 + m / z = 736.43([M + ]).
[0126] The synthetic route for preparing compound I-5 is as follows:
[0127]
[0128] Experimental Procedure: Compound III-1 (5.1 g, 6.93 mmol, 1 eq) and diphenyl sulfoxide (7.58 g, 41.6 mmol, 6 eq) were added to a 250 mL round-bottom flask and dissolved in 20 mL of dry dichloromethane. The reaction mixture was placed in an acetonitrile bath, and 20 mL of a dichloromethane solution of trifluoromethanesulfonic anhydride (19.7 g, 70 mmol, 10 eq) was added dropwise. After the addition was complete, the reaction was carried out in the dark for 5 h (reaction temperature: -42 °C). Most of the reaction mixture was removed by rotary evaporation. A white precipitate was obtained by adding the precipitate dropwise to diethyl ether, with a yield of 72%. 1 ¹H NMR (400MHz, deuterated DMSO) δ=8.25(s, 4H), 7.97-7.77(m, 56H), 3.18(t, J=5.9, 4H), 2.33(2H, s), 2.15(2H, s), 2.04(8H, q, J 11.6, 10.9), 1.83(2H, s), 1.14(4H, m), 0.90(4H, h, J 7.4), 0.44(6H, t, J 7.4). MS (ESI): m / z=513.47, calculated C 104 H 92 F6O8S6 2+ m / z = 888.11 ([M]) 2+ m / z = 148.95, calculated value CF3SO3 - m / z = 148.95 ([M]) - ).
[0129] Example 6
[0130] The synthetic route for preparing compound III-2 is as follows:
[0131]
[0132] The specific steps are the same as the preparation process of II-1 in Example 1, except that 4-methylthiophenylboronic acid is replaced with phenylboronic acid and IV-1 is replaced with IV-2, with a reaction yield of 83%. 1 H NMR (400MHz, deuterated DMSO) δ 8.03 (s, 4H), 7.51 (d, J = 7.1, 8H), 7.39 (m, 8H), 7.41 (d, J = 5.1, 4H), 3.87 (s, 6H), 2.33 (2H, s), 2.17 (2H, s), 2.04 (8H, q, J 11.6, 10.9), 1.83 (2H, s); MS (MALDI): m / z = 652.88, calculated C 48 H 44 O2 + m / z = 652.88 ([M]) + ).
[0133] The synthetic route for preparing compound I-6 is as follows:
[0134]
[0135] The specific steps are the same as the preparation process of I-5 in Example 5, except that III-1 is replaced with III-2, and the reaction yield is 75%. 1 H NMR (400MHz, deuterated DMSO) δ=8.25(s,4H),7.97-7.75(m,56H),3.90(6H,s),2.33(2H,s),2.17(2H,s),2.04(8H,q,J 11.7,10.6),1.82(2H,s); MS (ESI):m / z=846.03, calculated C 98 H 80 F6O8S6 2+ m / z = 846.03 ([M]) 2+ m / z = 148.95, calculated value CF3SO3 - m / z = 148.95 ([M]) - ).
[0136] Example 7
[0137] The synthetic route for preparing compound I-7 is as follows:
[0138]
[0139] The specific steps are the same as the preparation process of I-1 in Example 1, except that iodomethane is replaced with benzyl bromide, and the reaction yield is 90%. 1 ¹H NMR (600MHz, acetonitrile-d³) δ 7.97 (¹⁶H, m), 7.51 (⁴H, s), 7.25 (⁸H, m), 7.22 (⁴H, t), 7.18 (⁸H, d), 3.88 (⁶H, s), 3.18 (⁻¹⁴H, s), 2.33 (⁻¹⁷H, s), 2.17 (⁻¹⁷H, s), 2.04 (⁸H, q, J 11.6, 10.9), 1.83 (⁻¹⁸H, s); MS (ESI): m / z = 792.02, calculated C 88 H 92 O8S6F6 2+ m / z = 792.02 ([M]) 2+ m / z = 148.95, calculated value CF3SO3 - m / z = 148.95 ([M]) - ).
[0140] Example 8
[0141] The thermal stability and glass transition temperature of compounds I-1 and I-3 prepared in Examples 1 and 3 were determined. The differential scanning calorimetry and thermogravimetric analysis of the compound in Example 1 are shown in [reference needed]. Figure 1 Differential scanning calorimetry (DSC) and thermogravimetric analysis of the compound in Example 3 are shown in [reference needed]. Figure 2 The results showed that the thermal decomposition temperatures of both compounds were above 170℃, indicating good thermal stability.
[0142] Example 9
[0143] Compound I-1 from Example 1 was dissolved in acetonitrile to prepare a 30 mg / ml solution. This solution was filtered through a 0.22 μm microporous filter to obtain a spin-coating solution. This solution was then spin-coated onto an untreated silicon substrate. The uniformity of the film was analyzed using atomic force microscopy (AFM). (See attached figure.) Figure 3 As can be seen from the figure, the obtained film is very uniform.
[0144] Example 10
[0145] A negative photoresist formulation and photolithography: Compound I-1 from Example 1 was dissolved in acetonitrile to prepare a solution with a mass concentration of 20 mg / ml. The solution was filtered through a microporous filter with a pore size of 0.22 μm to obtain a spin-coating solution. This solution was then spin-coated onto an untreated silicon substrate. The substrate was pre-baked at 100°C for 2 minutes, and the film thickness was measured using an ellipsometer. The prepared film was then exposed using an electron beam light source at the National Center for Nanoscience and Technology with exposure periods of 100 nm, 80 nm, and 60 nm. Very uniform lithographic stripes were obtained. The test results are shown in [Figure number missing]. Figure 4 , Figure 5 and Figure 6 .in Figure 4 This is a photolithographic pattern with a photoresist exposure cycle of P100. Figure 5 This is a photolithographic pattern with a photoresist exposure cycle of P80. Figure 6 The resulting lithographic pattern has a photoresist exposure cycle of P60 and a stripe width of approximately 30 nm. The results show that the obtained pattern simultaneously exhibits excellent resolution, contrast, and very low line edge roughness.
[0146] Example 11
[0147] A negative photoresist formulation and photolithography: Compound I-2 from Example 2 was dissolved in acetonitrile to prepare a solution with a mass concentration of 20 mg / ml. This solution was filtered through a microporous filter with a pore size of 0.22 μm to obtain a spin-coating solution. This solution was then spin-coated onto an untreated silicon substrate. The substrate was pre-baked at 100°C for 2 minutes, and the film thickness was measured using an ellipsometry. The prepared film was then exposed using an electron beam light source at the National Center for Nanoscience and Technology with an exposure period of 80 nm. This resulted in very uniform lithographic stripes. The test results are shown in [Figure number missing]. Figure 7 .in Figure 7 The resulting lithographic pattern has a photoresist exposure cycle of P80 and a stripe width of approximately 40 nm. The results demonstrate that the obtained pattern exhibits excellent resolution, contrast, and very low line edge roughness.
[0148] Example 12
[0149] A negative photoresist formulation and photolithography: Compound I-5 from Example 5 was dissolved in acetonitrile to prepare a solution with a mass concentration of 20 mg / ml. This solution was filtered through a microporous filter with a pore size of 0.22 μm to obtain a spin-coating solution. This solution was then spin-coated onto an untreated silicon substrate. The substrate was pre-baked at 100°C for 2 minutes, and the film thickness was measured using an ellipsometry. The prepared film was then exposed using an electron beam light source at the National Center for Nanoscience and Technology with an exposure period of 60 nm. This resulted in very uniform lithographic stripes. The test results are shown in [Figure number missing]. Figure 8 .in Figure 8 The resulting lithographic pattern has a photoresist exposure cycle of P60 and a stripe width of approximately 30 nm. The results show that the obtained pattern simultaneously exhibits excellent resolution, contrast, and very low line edge roughness.
[0150] Example 13
[0151] A negative photoresist formulation and photolithography: Compound I-7 from Example 7 was dissolved in acetonitrile to prepare a solution with a mass concentration of 20 mg / ml. This solution was filtered through a microporous filter with a pore size of 0.22 μm to obtain a spin-coating solution. This solution was then spin-coated onto an untreated silicon substrate. The substrate was pre-baked at 100°C for 2 minutes, and the film thickness was measured using an ellipsometer. The prepared film was then exposed using an electron beam light source at the National Center for Nanoscience and Technology with an exposure period of 50 nm. This resulted in very uniform lithographic stripes. The test results are shown in [Figure number missing]. Figure 9 .in Figure 9 The resulting lithographic pattern has a photoresist exposure cycle of P50 and a stripe width of approximately 25 nm. The results show that the obtained pattern simultaneously exhibits excellent resolution, contrast, and very low line edge roughness.
[0152] The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiments. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.
Claims
1. The compound represented by formula (I): (I) in, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 Whether the same or different, each is independently selected from -S + R S1 R S2 -OC 1-15 Alkyl-C 6-20 Aryl-S + R S1 R S2 or group Z, wherein group Z is H, unsubstituted, or optionally substituted with one, two, or more R groups. A The following groups are substituted: C 1-15 Alkyl, C 1-15 Alkoxy, C 3-20 cycloalkyl, C 6-20 Aryl, 5-20 membered heteroaryl, 3-20 membered heterocyclic, -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 selected from -OC 1-15 Alkyl-C 6-20 Aryl-S + R S1 R S2 Or, as described above, group Z; R A Selected from O, NO2, C 1-15 Alkyl, C 1-15 Alkoxy, C 3-20 cycloalkyl, C 6-20 Aryl, 5-20 heteroaryl; R S1 R S2 Whether identical or different, each is independently selected from unsubstituted or arbitrarily selected by one, two or more R B The following groups are substituted: C 1-15 Alkyl, C 3-20 cycloalkyl, C 6-20 Aryl, -C 1-15 Alkyl-C 6-20 Aryl, 5-20 heteroaryl, deuterated C 1-15 Alkyl, or R S1 R S2 Together with the S connected thereto, they form an unsubstituted or optionally substituted group of one, two or more R groups. B The substituted 5-8 member sulfur-containing heterocyclic group; the 5-8 member sulfur-containing heterocyclic group optionally further contains 1-2 oxygen or sulfur atoms; the 5-8 member sulfur-containing heterocyclic group is also optionally fused with one or two benzene rings; R B They may be the same or different, and are independently selected from H, oxo (=O), nitro, CN, and C. 1-15 Alkyl, C 1-15 Alkoxy; X – It is an anion; n equals the thionium salt group -S in the molecule. + R S1 R S2 S + The number of S + and X – To make the compound as a whole electrically neutral, n is an integer from 2 to 6; that is, the compound shown in formula (I) has 2 to 6 -S groups. + R S1 R S2 .
2. The compound according to claim 1, characterized in that, X – It can be a halide ion, carboxylate ion, alkyl sulfonate ion, haloalkyl sulfonate ion, p-toluenesulfonate ion, sulfonamide anion, tetrafluoroborate ion, hexafluoroantimonate ion, hexafluorophosphate ion, or bis(trifluoromethanesulfonyl)imide ion.
3. The compound according to claim 1, characterized in that, X – It consists of trifluoromethanesulfonate, perfluoropropylsulfonate, and perfluorobutylsulfonate.
4. The compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 Whether the two are the same or different, they are each independently selected from H or -S. + R S1 R S2 ;R S1 R S2 Whether the two are the same or different, each is independently selected from C. 1-6 Alkyl, -C 6-12 Aryl, -C 1-6 Alkyl-C 6-12 Aryl; R is C 1-6 Alkyl group.
5. The compound according to any one of claims 1-4, characterized in that, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 Whether the two are the same or different, they are each independently selected from H and -S. + (C) 1-6 Alkyl) 2, -S + (C) 6-12 Aryl) 2, -S + (-C) 1-6 Alkyl-C 6-12 Aryl (C) 1-6 alkyl); R can be methoxy, ethoxy, propoxy, or butoxy.
6. The following compounds: 。 7. Use of the compound according to any one of claims 1-6 in the preparation of photoresist.
8. A photoresist composition comprising the compound according to any one of claims 1-6.
9. The photoresist composition according to claim 8, wherein, The photoresist composition further includes a solvent selected from one, two or more of the following substances: propylene glycol methyl ether acetate, dimethylformamide, cyclohexanone, ethyl n-pentanone, ethyl isopentanone, ethanol, acetonitrile, isopropanol, acetone, methyl n-pentanone, and methyl isopentanone.
10. The photoresist composition according to claim 8, wherein, The photoresist composition is a positive or negative photoresist composition.
11. The photoresist composition according to any one of claims 8-10, wherein, The photoresist composition is a single-component photoresist composition, containing only the compound described in any one of claims 1-6, except for the solvent.
12. A photoresist coating comprising the compound according to any one of claims 1-6.
13. The method for preparing the photoresist coating according to claim 12, characterized in that, This includes preparation by applying the photoresist composition according to any one of claims 8-11 onto a substrate.
14. The application of the compound according to any one of claims 1-6, the photoresist composition according to any one of claims 8-11, or the photoresist coating according to claim 12 in photolithography.
15. The application according to claim 14, wherein, The photolithography is 248nm photolithography, 193nm photolithography, extreme ultraviolet photolithography, nanoimprint lithography, or electron beam lithography.
Citation Information
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