Sulfonium salt modified metallocene compound monomolecular resin and photoresist thereof

Abstract

The invention provides a series of novel monomolecular resin based on the metallocene compound, the monomolecular resin is used as a single-component non-chemical amplification photoresist, the problems of non-uniform distribution of an acid generator and an anti-acid diffusion agent, non-uniform acid diffusion and the like in a chemical amplification photoresist are avoided, and an obtained pattern has high resolution and low line width roughness. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the technical field of materials, and in particular relates to a type of monomolecular resin based on a sulfonium salt-modified metallocene compound and a photoresist thereof. Background Art

[0002] With the rapid development of the semiconductor industry, the integration of semiconductor devices is getting higher and higher, and the resolution required to be achieved by photolithography technology is also getting higher and higher. The quality of high-resolution photolithography patterns also puts forward higher requirements, especially the line width roughness (LWR) and line edge roughness (LER) of the patterns are becoming more and more stringent. Photoresist is a key material for the transfer of photolithography patterns during the processing of semiconductor devices. The photoresist is coated on different substrates, and after being irradiated with energy such as light beams, electron beams, ion beams or x-rays, the solubility changes, and then the corresponding pattern is transferred to the substrate through development and etching processes. The resolution that can be achieved by the pattern formed by the photoresist has a decisive influence on the integration of the device. The comprehensive performance of the photoresist needs to match the development of current photolithography technology.

[0003] Traditionally used chemically amplified photoresists (CARs) rely on mixed or polymer-bonded photoacid generators (PAGs) to achieve solubility differences. This chemically amplified photoresist system has a series of problems, such as high line edge roughness (LER) and line width roughness (LWR), instability after exposure, etc. In order to solve these problems, the research on new non-chemically amplified photoresists (n-CARs) is receiving increasing attention. n-CARs are materials that are directly sensitive to radiation. They do not require the addition of PAGs in their formulations and only contain one component, the host material. Therefore, they can effectively solve the compatibility problem between the host material and the additive, as well as the problem of uneven acid diffusion after exposure, thereby reducing the LER value. However, compared with the number of CARs reported to date, the number of n-CARs is very limited, especially those based on single-molecule resins. Therefore, it is of great significance to develop single-molecule resin n-CARs with strong lithography potential, especially for sub-20nm patterning applications with low LER / LWR characteristics. Summary of the invention

[0004] In order to improve the above technical problems, the present invention first provides a compound represented by the following formula (I):

[0005]

[0006] Wherein: Ra is the same or different and is independently selected from the following groups which are unsubstituted or optionally substituted by one, two or more Ra1: C 1-12 Alkyl, C 3-20 Cycloalkyl, 3-20 membered heterocyclic group, C 6-20 Aryl, 5-20 membered heteroaryl, -C1-12 Alkyl-C 6-20 Aryl, -C 1-12 Alkyl-5-20 membered heteroaryl, -C 1-12 Alkyl-CO-C 6-20 Aryl, -C 1-12 Alkyl-CO-5-20 membered heteroaryl, -C 1-12 Alkyl-CO-C 1-12 Alkyl, -C 1-12 Alkyl-CO-C 3-20 Cycloalkyl;

[0007] Rb are the same or different and are independently selected from hydrogen, unsubstituted or optionally substituted by one, two or more Rb1: 1-12 Alkyl, C 1-12 Alkoxy, C 3-20 Cycloalkyl, 3-20 membered heterocyclic group;

[0008] Rc are the same or different and are independently selected from a chemical bond or -C 1-12 Alkyl-O-, where -C 1-12 The alkyl end of alkyl-O- is connected to the COO bond;

[0009] Y – is a negative ion, for example, selected from halide ions, C 2-6 Alkyl sulfonate, halogenated alkyl sulfonate (such as trifluoromethanesulfonate, perfluoropropylsulfonate, perfluorobutylsulfonate), p-toluenesulfonate, tetrafluoroborate, hexafluorophosphate, hexafluoroantimonate, bistrifluoromethanesulfonyl imide ion;

[0010] Ra1, Rb1 are the same or different and are independently selected from nitro, cyano, halogen, C 1-12 Alkyl, C 1-12 Alkoxy or halogenated C 1-12 alkyl;

[0011] Z is selected from divalent metals such as Fe, Zn, Ru, Os, Cd, Hg, Ni, Co, Rh, Pd, Pt, Sn, and Pb.

[0012] In some embodiments of the present invention, Ra are the same or different and are independently selected from C 1-6 Alkyl or C 6-14 an aryl group, such as methyl or phenyl;

[0013] In some embodiments of the present invention, Rb are the same or different and are independently selected from hydrogen or C 1-6 Alkyl, such as H or methyl;

[0014] In some embodiments of the present invention, Rc is selected from a chemical bond or -C 1-6Alkyl-O-, for example -methyl-O-, -ethyl-O-, -propyl-O-;

[0015] In some embodiments of the present invention, Y is selected from the group consisting of halide, triflate, perfluorobutanesulfonate, p-toluenesulfonate.

[0016] As an example, the compound of formula (I) is selected from the following compounds:

[0017]

[0018] The present invention also provides a method for preparing the compound represented by formula (I), comprising the following steps:

[0019]

[0020] Compound (Ia) reacts with compound (Ib) to obtain a compound represented by formula (I);

[0021] or,

[0022]

[0023] Compound (Ia) reacts with compound (Ic) to obtain compound (Id), and compound (Id) reacts with compound (Ie) to obtain the compound represented by formula (I);

[0024] wherein Ra, Rb, Rc, and Y have the same meanings as described above.

[0025] The present invention also provides the use of the compound represented by the above formula (I), which is used as a photoresist, especially as a single-component photoresist.

[0026] The present invention also provides a photoresist composition, which comprises the compound represented by formula (I) as described above.

[0027] According to an embodiment of the present invention, the photoresist composition also includes a solvent, which is selected from one, two or more of the following substances: propylene glycol methyl ether acetate (PGMEA), dimethylformamide (DMF), cyclohexanone, ethyl n-amyl ketone, ethyl isoamyl ketone, ethanol, acetonitrile, isopropanol, acetone, methyl n-amyl ketone, and methyl isoamyl ketone.

[0028] According to an embodiment of the present invention, the photoresist composition is a positive or negative photoresist composition.

[0029] In one embodiment, the photoresist composition is a single-component photoresist, which is composed of the compound represented by formula (I) and a solvent, that is, the photoresist composition includes only one photoresist component except the solvent, that is, it does not contain an acid generator except the compound represented by formula (I).

[0030] The present invention also provides a photoresist coating, which comprises the compound represented by formula (I) as described above.

[0031] The present invention also provides a method for preparing the above-mentioned photoresist coating, comprising: applying the above-mentioned photoresist composition on a substrate to prepare the coating.

[0032] In one embodiment, the applying method is spin coating.

[0033] In one embodiment, the substrate is a silicon wafer substrate.

[0034] Preferably, the photoresist coating is a thin film.

[0035] The present invention also provides the use of the compound represented by formula (I) as described above, the photoresist composition or the photoresist coating in photolithography.

[0036] According to an embodiment of the present invention, the photoresist coating is used in modern lithography technologies such as 248nm lithography, 254nm lithography, 193nm lithography, extreme ultraviolet (EUV) lithography, nanoimprint lithography or electron beam lithography, preferably in ultraviolet, extreme ultraviolet and electron beam lithography.

[0037] Beneficial Effects

[0038] (1) The present invention provides a series of novel single-molecule resins based on metallocene compounds, namely, compounds represented by formula (I), the raw materials of which are cheap and readily available, and the synthesis process is simple;

[0039] (2) The compound represented by formula (I) of the present invention can be used as a single-component non-chemically amplified photoresist, thereby avoiding the problems of uneven distribution of acid generators and acid diffusion inhibitors and uneven acid diffusion in chemically amplified photoresists, and the resulting pattern has high resolution and low line width roughness.

[0040] (3) The metallocene compound-based single-molecule resin of the present invention has a definite molecular structure and a single molecular size, which can well meet the requirements of high-resolution lithography.

[0041] (4) The metallocene compound-based single-molecule resin of the present invention introduces a metallocene structure into the photoresist. The addition of metal elements can improve the etching resistance of the photoresist and improve the sensitivity of the photoresist in electron beam lithography and EUV lithography. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] Figure 1 This is an AFM image of the thin film of compound I-1 in Example 1 of the present invention.

[0043] Figure 2 This is a thermogravimetric curve of compound I-1 in Example 1 of the present invention.

[0044] Figure 3 This is the deep ultraviolet exposure pattern (negative resist) of the photoresist containing compound I-1 in Example 1 of the present invention.

[0045] Definition and explanation of terms

[0046] Unless otherwise defined, all technical and scientific terms herein have the same meaning as commonly understood by one of ordinary skill in the art to which the claimed subject matter belongs.

[0047] "More" means three or more.

[0048] The term "halogen" includes F, Cl, Br or I.

[0049] The term "C 1-12 "Alkyl" is understood to mean a straight-chain or branched saturated monovalent hydrocarbon group having 1 to 12 carbon atoms, preferably C 1-6 Alkyl. "C 1-6 The term “alkyl” is understood as meaning preferably a linear or branched, saturated, monovalent hydrocarbon radical having 1, 2, 3, 4, 5 or 6 carbon atoms. The alkyl radical 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, etc. or their isomers. In particular, the radical has 1, 2 or 3 carbon atoms (“C 1-3 alkyl"), for example methyl, ethyl, n-propyl or isopropyl.

[0050] The term "C 3-20 "Cycloalkyl" is understood to mean a saturated monovalent monocyclic or bicyclic hydrocarbon ring having 3 to 20 carbon atoms, preferably "C 3-12 The term "Cycloalkyl" 3-12 "Cycloalkyl" is understood to mean a saturated, monovalent, monocyclic or bicyclic hydrocarbon ring having 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms. 3-12 The cycloalkyl group may be a monocyclic hydrocarbon group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl, or a bicyclic hydrocarbon group such as a decalin ring.

[0051] The term "3-20 membered heterocyclyl" means a saturated monovalent monocyclic or bicyclic hydrocarbon ring containing 1-5 heteroatoms independently selected from N, O and S, preferably a "3-12 membered heterocyclyl". The term "3-12 membered heterocyclyl" means a saturated monovalent monocyclic or bicyclic hydrocarbon ring containing 1-5, preferably 1-3 heteroatoms selected from N, O and S. The heterocyclyl may be connected to the rest of the molecule through any one of the carbon atoms or the nitrogen atom (if present). In particular, the heterocyclyl may include, but is not limited to, a 4-membered ring 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 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]pyrazine-2(1H)-yl ring. The ring containing nitrogen atoms may be partially unsaturated, i.e., it may contain one or more double bonds, for example, but not limited to, 2,5-dihydro-1H-pyrrolyl, 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. According to the present invention, the heterocyclic group is non-aromatic.

[0052] The term "C 6-20 "Aryl" is understood to mean a monovalent aromatic or partially aromatic monocyclic, bicyclic or tricyclic hydrocarbon ring having 6 to 20 carbon atoms, preferably "C 6-14 The term "C 6-14 "Aryl" is understood to mean preferably a monovalent aromatic or partially aromatic monocyclic, bicyclic or tricyclic hydrocarbon ring ("C 6-14 Aryl), especially a ring having 6 carbon atoms ("C 6 aryl), such as phenyl; or biphenyl, or a ring having 9 carbon atoms ("C 9 aryl), such as indanyl or indenyl, or a ring having 10 carbon atoms ("C 10 aryl), such as tetrahydronaphthyl, dihydronaphthyl or naphthyl, or a ring having 13 carbon atoms ("C 13 aryl), such as fluorenyl, or a ring having 14 carbon atoms ("C 14 "aryl"), for example anthracenyl.

[0053] The term "5-20 membered heteroaryl" is 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, for example "5-14 membered heteroaryl". The term "5-14 membered heteroaryl" is 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, in particular 5 or 6 or 9 or 10 carbon atoms, and containing 1 to 5, preferably 1 to 3 heteroatoms independently selected from N, O and S and, in addition, in each case may be benzo-fused. In particular, the heteroaryl group is selected from thienyl, furanyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, thia-4H-pyrazolyl and the like and benzo derivatives thereof, such as benzofuranyl, benzothienyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, benzotriazolyl, indazolyl, indolyl, isoindolyl and the like; or pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl and the like and benzo derivatives thereof, such as quinolyl, quinazolinyl, isoquinolyl and the like; or azinyl, indolizinyl, purinyl and the like and benzo derivatives thereof; or cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl and the like.

[0054] The above term “C 1-12 The definition of "alkyl" also applies to other C-containing 1-12 Alkyl groups, such as C 1-12 Alkoxy, halogenated C 1-12 Alkyl, -C 1-12 Alkyl-C 6-20 Aryl, -C 1-12 Alkyl-5-20 membered heteroaryl, -C 1-12 Alkyl-CO-C 6-20 Aryl, -C 1-12 Alkyl-CO-5-20 membered heteroaryl, -C 1-12 Alkyl-CO-C 1-12 Alkyl, -C 1-12 Alkyl-CO-C 3-20 Cycloalkyl, etc.

[0055] Similarly, C 6-20 Aryl, 5-20 membered heteroaryl, C 3-20 Cycloalkyl has the same definition throughout. DETAILED DESCRIPTION

[0056] The technical scheme of the present invention will be further described in detail below in conjunction with specific embodiments. It should be understood that the following embodiments are only exemplary descriptions and explanations 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 included in the scope that the present invention is intended to protect.

[0057] Unless otherwise specified, the raw materials and reagents used in the following examples are commercially available or can be prepared by known methods.

[0058] Example 1

[0059] The synthetic route of compound I-1 with ferrous ion as the core is as follows:

[0060]

[0061] Synthesis of compound A:

[0062] Specific steps: 6 g of 1,1-ferrocenedicarboxylic acid is added to 100 ml of ultra-dry dichloromethane in an ice bath, and after stirring evenly, 13.5 ml of oxalyl chloride and 6 ml of pyridine are added thereto, and the mixture is reacted under reflux for 2 hours. After the reaction, the solid is spin-dried to obtain the product, and the product is hot-extracted with petroleum ether, and the solid is spin-dried to obtain the product. After drying, 3.9 g of the product compound A is obtained, and the yield is 57%. 1 HNMR (400MHz, CDCl 3 )δ5.05(s,4H),4.64(s,4H).

[0063] Synthesis of compound B:

[0064] Specific steps: 880 mg of compound A was dissolved in ultra-dry dichloromethane, p-methylthio-m-cresol and triethylamine were added thereto under ice bath conditions, and then reacted at room temperature for 24 hours, and then dried by spin drying, and passed through a column (V 乙酸乙酯：石油醚 =1:3), and 200 mg of product was obtained.

[0065] Synthesis of compound I-1:

[0066] Specific steps: Compound B was dissolved in ultra-dry acetonitrile, methyl trifluoromethanesulfonate was added thereto under light-shielding conditions, and then reacted at room temperature for 2 hours. After the reaction, it was precipitated in ether, and then dissolved again in acetonitrile and precipitated in ether to obtain 230 mg of the product. 1 H NMR (400 MHz, DMSO-d 6)δ8.23(s,1H),δ8.21(s,1H),δ7.54(d,1H),δ7.52(d,1H),δ7.46(d,2H),δ5.09(s,4H),4.85(s,4H),3.26(s,12H),2.6(s,6H); MS(ESI):m / z=287.77,calculated value C 30 H 32 FeO 4 S 2 2+ m / z=287.77([M] 2+ ); m / z = 287.77, calculated value CF 3 SO 3 - m / z=148.95([M] - ).

[0067] Example 2

[0068] The synthetic route of compound I-2 with ferrous ion as the core is as follows:

[0069]

[0070] Synthesis of compound C:

[0071] Specific steps: 9g of p-bromophenyl sulfide is added to 50ml of ethylene glycol, and then 20g of potassium carbonate and 0.4g of copper chloride catalyst are added. After reflux at 140°C for 24h, a small amount of HCl aqueous solution is added, and then precipitated in a large amount of water. After filtering out the solid, it is repeatedly extracted with dichloromethane and water, and the organic phase is collected, spin-dried and passed through a column (V 乙酸乙酯：石油醚 =1:5). The white solid was obtained by spin drying, which was the product compound C.

[0072] Synthesis of compound D:

[0073] Specific steps: Compound C was dissolved in ultra-dry dichloromethane, compound A and triethylamine were added thereto under ice bath conditions, and then reacted under reflux conditions for 2 hours, dried by spin drying, and passed through a column (V 乙酸乙酯：石油醚 =1:3), to obtain 200 mg of product compound D.

[0074] Synthesis of compound I-2:

[0075] Specific steps: Compound D is dissolved in acetonitrile, methyl trifluoromethanesulfonate is added thereto under light-shielding conditions, followed by reaction at room temperature for 2 hours, precipitation in ether after the reaction, and then redissolved in acetonitrile and precipitated in ether to obtain the product. 1 H NMR (400 MHz, DMSO-d 6)δ8.01(d,4H),δ7.34(d,4H),δ4.76(s,4H),δ4.53(t,4H)δ4.50(s,4H),δ4.44(t,4H)δ3.21(s,12H); MS(ESI): m / z=636.60, calculated value C 32 H 36 FeO 6 S 2 2+ m / z=318.30([M] 2+ ); m / z = 318.30, calculated value CF 3 SO 3 - m / z=148.95([M] - ).

[0076] Example 3

[0077] The synthetic route of compound I-3 with ferrous ion as the core is as follows:

[0078]

[0079] Synthesis of compound E:

[0080] Specific steps: 1 eq. of o-dimethylphenol and 1.2 eq. of diphenyl sulfoxide were added to a single-mouth bottle, and the solid was observed to melt. Then, the freshly prepared P 2 O 5 / MeSO 3 The solution of H (7 ml, mass ratio 1:10) was slowly added thereto and stirred in an oil bath at 40°C for 3 h. The solution after the reaction was poured into an aqueous solution of sodium p-toluenesulfonate and stirred, extracted with DCM, and the organic phase was collected and spin-dried. The spin-dried product was dissolved in a small amount of DCM and then washed with ether for precipitation. The solid was centrifuged and dried in an oven at 60°C to obtain compound E.

[0081] Synthesis of compound I-3:

[0082] Specific steps: Compound A and Compound E were dissolved in 25 ml of DCM, 2 eq. of triethylamine and 0.1 eq. of DMAP were added, and the mixture was reacted at room temperature in the dark for 1 h. The developing agent (V DCM:甲醇 =5:1) midpoint plate, it was observed that there was almost no residue of raw material, and the reaction was closed after reacting for another 2h. The solution after the reaction was rotary evaporated until a small amount of liquid remained, and precipitated in a large amount of ether. The precipitated solid was centrifuged and dried in an oven at 60°C. 1 H NMR (400 MHz, CDCl 3)δ7.73(s,20H),7.48(s,12H),5.05(s,4H),4.72(s,4H),2.31(s,18H);MS(ESI):m / z=426.10,calculated value C 52 H 44 FeO 4 S 2 2+ m / z=426.44([M] 2+ ); m / z = 426.44, calculated value C 7 H 7 O 3 S - m / z=171.19([M] - ).

[0083] Example 4

[0084] The synthetic route of compound I-4 with ferrous ion as the core is as follows:

[0085]

[0086] Synthesis of compound F:

[0087] Specific steps: 1 eq. of o-dimethylphenol and 1.2 eq. of diphenyl sulfoxide were added to a single-mouth bottle, and the solid was observed to melt. Then, the freshly prepared P 2 O 5 / MeSO 3 H (7 ml mass ratio 1:10) solution was slowly added thereto and reacted in a 40°C oil bath for 3 hours. The reaction solution was poured into an aqueous solution of potassium perfluorobutylsulfonate (12.5 g / 600 ml water) and stirred, extracted with DCM, and the organic phase was collected and spin-dried. The spin-dried product was dissolved in a small amount of DCM to obtain a brown-yellow oily liquid. The product was purified by column chromatography (eluent V DCM:CH3OH =20:1), to obtain brown-yellow solid compound F.

[0088] Synthesis of compound I-4:

[0089] Specific steps: 1 eq. (7.6 g) of the product compound F in the previous step and 2.3 g of compound A were added to a single-mouth bottle, and then 3.6 ml of triethylamine and 0.16 g of DMAP were added, and the mixture was reacted in an oil bath at 40°C, and then dried by spin drying and passed through a column (V DCM:CH3OH =50:1 gradient wash V DCM:CH3OH =20:1) After passing through the column, 4 g of product was obtained. 1 H NMR (400 MHz, CDCl 3)δ7.73(s,20H),7.48(s,4H),5.05(s,4H),4.72(s,4H),2.31(s,12H);MS(ESI):m / z=426.10,calculated value C 52 H 44 FeO 4 S 2 2+ m / z=426.44([M] 2+ ); m / z = 426.44, calculated value C 4 F 9 O 3 S - m / z=299.09([M] - ).

[0090] Example 5

[0091] Compound I-1 in Example 1 was dissolved in acetonitrile to obtain a solution with a concentration of 20 mg / ml. The solution was then filtered through a microporous filter with a pore size of 0.22 μm to obtain a spin coating solution. The spin coating solution was spin coated on a silicon substrate to form a film, and the uniformity and flatness of the film were analyzed using a scanning electron microscope (AFM). The results are shown in the attached Figure 1 It can be seen from the figure that the obtained film is very uniform and has no crystallization phenomenon, which is conducive to obtaining a smooth surface lithography pattern.

[0092] Example 6

[0093] The thermal stability of the compound I-1 prepared in Example 1 was measured. The results showed that its decomposition temperature reached above 200°C, and it had good thermal stability. Figure 2 Therefore, the use of compound I-1 can maintain stability during the pre-bake and post-bake processes of photolithography, meeting the requirements of photolithography.

[0094] Example 7

[0095] A negative photoresist formulation and its use in UV lithography: Compound I-1 of Example 1 was dissolved in acetonitrile to obtain a solution with a 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. The spin coating solution was spin-coated on a silicon substrate to form a film, and baked at 80°C for 3 minutes. The prepared film was subjected to an exposure experiment (254 nm UV lamp) for 40 seconds, and then developed with deionized water to obtain very clear stripes, as shown in FIG. Figure 3 .Depend on Figure 3 It can be seen that the width of the photolithography stripe is 2.78 microns.

[0096] The above is an explanation of the embodiments of the present invention. However, the present invention is not limited to the above embodiments. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. Compound represented by formula (I): in: Ra are the same or different and are independently selected from the following groups which are unsubstituted or optionally substituted by one, two or more Ra1: C 1-12 Alkyl, C 3-20 Cycloalkyl, 3-20 membered heterocyclic group, C 6-20 Aryl, 5-20 membered heteroaryl, -C 1-12 Alkyl-C 6-20 Aryl, -C 1-12 Alkyl-5-20 membered heteroaryl, -C 1-12 Alkyl-CO-C 6-20 Aryl, -C 1-12 Alkyl-CO-5-20 membered heteroaryl, -C 1-12 Alkyl-CO-C 1-12 Alkyl, -C 1-12 Alkyl-CO-C 3-20 Cycloalkyl; Rb are the same or different and are independently selected from hydrogen, unsubstituted or optionally substituted by one, two or more Rb1: 1-12 Alkyl, C 1-12 Alkoxy, C 3-20 Cycloalkyl, 3-20 membered heterocyclic group; Rc are the same or different and are independently selected from a chemical bond or -C 1-12 Alkyl-O-, where -C 1-12 The alkyl end of alkyl-O- is connected to the COO bond; Y – is a negative ion, for example, selected from halide ions, C 2-6 Alkyl sulfonate, haloalkyl sulfonate, p-toluene sulfonate, tetrafluoroborate, hexafluorophosphate, hexafluoroantimonate, bis(trifluoromethanesulfonyl)imide ion; Ra1, Rb1 are the same or different and are independently selected from nitro, cyano, halogen, C 1-12 Alkyl, C 1-12 Alkoxy or halogenated C 1-12 alkyl; Z is selected from divalent metals such as Fe, Zn, Ru, Os, Cd, Hg, Ni, Co, Rh, Pd, Pt, Sn, and Pb.

2. The compound according to claim 1, characterized in that Ra are the same or different and are independently selected from C 1-6 Alkyl or C 6-14 an aryl group, such as methyl or phenyl; Preferably, Rb are the same or different and are independently selected from hydrogen or C 1-6 Alkyl, such as H or methyl; Preferably, Rc is selected from a chemical bond or -C 1-6 Alkyl-O-, for example -ethyl-O-; Preferably, Y is selected from halide, trifluoromethanesulfonate, perfluorobutanesulfonate, p-toluenesulfonate.

3. The compound according to claim 1 or 2, characterized in that The compound of formula (I) is selected from the following compounds:

4. A method for preparing the compound according to any one of claims 1 to 3, characterized in that: The steps include: Compound (Ia) reacts with compound (Ib) to obtain a compound represented by formula (I); or, Compound (Ia) reacts with compound (Ic) to obtain compound (Id), and compound (Id) reacts with compound (Ie) to obtain the compound represented by formula (I); Wherein, Ra, Rb, Rc, and Y have the definitions as described in any one of claims 1-3.

5. Use of the compound according to any one of claims 1 to 4 as a photoresist.

6. A photoresist composition, characterized in that: The invention comprises the compound according to any one of claims 1 to 3.

7. The photoresist composition according to claim 6, characterized in that The photoresist composition also includes a solvent, which is selected from one, two or more of the following substances: propylene glycol methyl ether acetate, dimethylformamide, cyclohexanone, ethyl n-amyl ketone, ethyl isoamyl ketone, ethanol, acetonitrile, isopropanol, acetone, methyl n-amyl ketone, and methyl isoamyl ketone.

8. The photoresist composition according to claim 6 or 7, characterized in that: The photoresist composition is a positive or negative photoresist composition.

9. Use of the compound represented by formula (I) according to any one of claims 1 to 3 or the photoresist composition according to any one of claims 6 to 8 in photolithography.

10. The use according to claim 9, characterized in that: The photolithography is 248nm photolithography, 254nm photolithography, 193nm photolithography, extreme ultraviolet photolithography, nanoimprint photolithography or electron beam photolithography.

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