triazines not containing an ortho-hydroxy group

Abstract

The present application provides a triazine compound without ortho-hydroxyl group or a salt thereof, specifically a compound as shown in formula (I) or a salt thereof.

Description

Technical Field

[0001] This invention relates to a class of triazine compounds without ortho-hydroxyl groups, specifically to the application of compounds of formula (I) or their salts as UVB ultraviolet absorbers with high UVA transmittance in the anti-photoaging of polymer materials. Background Technology

[0002] Medium-wave ultraviolet (UVB) radiation with wavelengths in the range of 280–315 nm can excite chemical bonds such as CH and C-C bonds in polymer molecules, generating unstable free radicals. These free radicals can trigger further chain reactions in the polymer, such as polymer chain breakage and cross-linking, affecting the mechanical properties and physical stability of the polymer material. This can lead to problems such as yellowing, cracking, and decreased mechanical strength. Long-term UVB exposure accelerates material degradation and aging, shortening its lifespan.

[0003] To address this, additives such as UV absorbers, light stabilizers, and antioxidants are often added to polymer materials to improve their weather resistance. Among these, o-hydroxytriphenyltriazine is a common UV absorber. It possesses advantages such as low volatility, good lightfastness, low environmental toxicity, low biotoxicity, and a wide absorption range. It is widely used in various industrial plastics such as polyurethane, polyoxymethylene, polyvinyl butyral, and polyvinyl chloride.

[0004] However, some applications require selective absorption of UVB ultraviolet light while maximizing the transmission of long-wave ultraviolet light (UVA). For example, agricultural films need UVA transmission to promote photosynthesis in plants. Some photovoltaic cell encapsulation films require UVA transmission to improve conversion efficiency. O-hydroxytriphenyltriazine compounds, with maximum absorption wavelengths mostly greater than 320 nm, absorb both UVA and UVB, and most molecules exhibit a certain color (pale yellow or pale green), making them unsuitable for the aforementioned applications requiring high UVA transmission.

[0005] Therefore, if a UVB absorber with good lightfastness, low volatility and low toxicity, similar to o-hydroxytriazine, and high transmittance to long-wave ultraviolet light can be provided, it will be of great significance for improving the photoaging resistance of polymer materials and expanding the application range of triazine UV absorbers. Summary of the Invention

[0006] The purpose of this invention is to address the aforementioned problems by providing a class of triazine compounds or their salts that do not contain ortho-hydroxyl groups, and the application of such compounds or their salts as UVB ultraviolet absorbers with high UVA transmittance in polymer anti-photoaging.

[0007] This invention provides a compound of formula (I) or a salt thereof.

[0008]

[0009] in,

[0010] R1 is independently selected from C 1-8 Alkyl and C 2-6 alkenyl, C 1-8 Alkyl and C 2-6 The alkenyl group can be optionally surrounded by 1, 2, or 3 R groups. a replace;

[0011] R2 and R3 are each independently selected from H, F, Cl, Br, -CN, -NH2, and -SR. b and -S(=O)2R b ;

[0012] R4 and R5 are each independently selected from H, F, Cl, Br and CN;

[0013] Ring A and ring B are each independently selected from C. 6-10 aryl, 5-6 membered heterocyclic alkenyl and 5-10 membered heteroaryl, wherein at least one of ring A or ring B is selected from C. 6-10 Aryl;

[0014] R6 and R7 are each independently selected from H, F, Cl, Br, -CN, NH2, phenyl, and C. 1-5 Alkyl, C 1-5 Alkyl and phenyl groups are each optionally marked with 0, 1, 2 or 3 R groups. c replace;

[0015] m can be 0, 1, 2, or 3;

[0016] n is 0, 1, 2, or 3;

[0017] R a Each is independently selected from H, F, Cl, Br, -CN, -NH2, C 1-3 Alkyl, C 3～5 Cycloalkyl and 3-7 membered heterocycloalkyl, C 1-3 Alkyl, C 3～5 Cycloalkyl and 3-7 membered heterocycloalkyl groups are each optionally surrounded by 1, 2 or 3 R groups. a' replace;

[0018] R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2;

[0019] R b Each is independently selected from -CH3, -CH2CH3, and -CH2CH2CH3;

[0020] R cEach is independently selected from H, F, Cl, Br, -CN, -NH2, and C. 1-4 alkyl;

[0021] 3-7-membered heterocyclic alkyl, 5-6-membered heterocyclic alkenyl and 5-10-membered heteroaryl groups each independently contain 1, 2 or 3 atoms or groups independently selected from N, O, S and NH;

[0022] The condition is that the compound of formula (I) or its salts are not selected from:

[0023]

[0024]

[0025] In some embodiments of the present invention, the above-mentioned compound or a salt thereof, wherein R a Each is independently selected from F, Cl, Br, -CN, -NH2, -CH3, -CH2CH3, -CH2CH2CH3,

[0026] In some embodiments of the present invention, the above-mentioned compound or its salt, wherein R1 is selected from -CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -(CH2)4CH3, -(CH2)5CH3, -(CH2)3CH(CH3)2, -CHCH2, -CH2CHCH2, -(CH2)2CHCH2, wherein -CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -(CH2)4CH3, -(CH2)5CH3, -(CH2)3CH(CH3)2, -CHCH2, -CH2CHCH2 and -(CH2)2CHCH2 are each optionally selected by 1, 2 or 3 R1s. a replace.

[0027] In some embodiments of the present invention, the above-mentioned compound or its salt, wherein R1 is selected from -C(CH3)3, -C(CH2F)(CH3)2, -C(CH2Br)(CH3)2, -(CH2)3CH(CH3)2, -CH2CH(CH2CH3)(CH2)3CH3, ...

[0028] -CH2CH(CBr2CH3)(CH2)3CH3 and -CH2CH(CH2CHBr2)(CH2)3CH3.

[0029] In some embodiments of the invention, the above-mentioned compound or its salt, wherein R6 and R7 are independently selected from H, F, Cl, Br, -CN, NH2, -CH3, -CH2CH3, -CH(CH3)2, -(CH2)2CH3, -(CH2)3CH3, -C(CH3)3 and phenyl, wherein -CH3, -CH2CH3, -CH(CH3)2, -(CH2)2CH3, -(CH2)3CH3, -C(CH3)3 and phenyl are each optionally represented by 1, 2 or 3 R6 groups. c replace.

[0030] In some embodiments of the invention, the above-mentioned compound or its salt, wherein ring A and ring B are each independently selected from... The Each can be replaced by either m R6s or n R7s.

[0031] In some embodiments of the present invention, the above-mentioned compound or its salt, wherein the structure Selected from

[0032] In some embodiments of the present invention, the above-mentioned compound or its salt, wherein the structure Selected from

[0033] In one embodiment of the invention, a compound or a salt thereof of formula (I) shown above is provided, wherein:

[0034] R1 is selected from C 1-8 Alkyl, C 1-8 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a replace;

[0035] R2 and R3 are each independently selected from H, F, Cl, Br, -CN, -NH2, and -SR. b and -S(=O)2R b ;

[0036] R4 and R5 are each independently selected from H, F, Cl, Br and CN;

[0037] Ring A and ring B are each independently selected from C. 6-10 aryl and 5-10 heteroaryl, wherein at least one of ring A or ring B is selected from C. 6-10 Aryl;

[0038] R6 and R7 are each independently selected from H, F, Cl, Br, -CN, NH2, phenyl, and C. 1-5 Alkyl, C 1-5 Alkyl and phenyl groups are each optionally marked with 0, 1, 2 or 3 R groups.c replace;

[0039] m can be 0, 1, 2, or 3;

[0040] n is 0, 1, 2, or 3;

[0041] R a Each is independently selected from H, F, Cl, Br, -CN, -NH2, C 1-3 Alkyl, C 3～5 Cycloalkyl and 3-7 membered heterocycloalkyl, C 1-3 Alkyl, C 3～5 Cycloalkyl and 3-7 membered heterocycloalkyl groups are each optionally surrounded by 1, 2 or 3 R groups. a' replace;

[0042] R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2;

[0043] R b Each is independently selected from -CH3, -CH2CH3, and -CH2CH2CH3;

[0044] R c Each is independently selected from H, F, Cl, Br, -CN, -NH2, and C. 1-4 alkyl;

[0045] In one embodiment of the invention, a compound or a salt thereof of formula (I) shown above is provided, wherein:

[0046] R1 is selected from C1-8 Alkyl, C 1-8 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a replace;

[0047] R2 and R3 are each independently selected from H, F, Cl, Br, -CN and -NH2;

[0048] R4 and R5 are each independently selected from H, F, Cl, Br and CN;

[0049] Ring A and ring B are each independently selected from C. 6-10 aryl and 6-8 membered heteroaryl, wherein at least one of ring A or ring B is selected from C. 6-10 Aryl;

[0050] R6 and R7 are each independently selected from H, F, Cl, Br, -CN, NH2, phenyl, and C. 1-5 Alkyl, phenyl and C 1-5 Each alkyl group is optionally surrounded by 0, 1, 2 or 3 R's. c replace;

[0051] m can be 0, 1, 2, or 3;

[0052] n is 0, 1, 2, or 3;

[0053] R a Each is independently selected from H, F, Cl, Br, -CN, -NH2, and C. 1-3 Alkyl, C 1-3 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a' replace;

[0054] R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2;

[0055] R c Each is independently selected from H, F, Cl, Br, -CN, -NH2, and C. 1-4 alkyl;

[0056] In one embodiment of the invention, a compound or a salt thereof of formula (I) shown above is provided, wherein:

[0057] R1 is selected from C 1-8 Alkyl, C 1-8 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a replace;

[0058] R2 and R3 are each independently selected from H;

[0059] R4 and R5 are each independently selected from H;

[0060] Ring A and ring B are each independently selected from C. 6-10 aryl and 6-8 membered heteroaryl, wherein at least one of ring A or ring B is selected from C. 6-10 Aryl;

[0061] R6 and R7 are each independently selected from H, phenyl, and C. 1-5 Alkyl, C 1-5 Alkyl and phenyl groups are each optionally marked with 0, 1, 2 or 3 R groups. c replace;

[0062] m can be 0, 1, 2, or 3;

[0063] n is 0, 1, 2, or 3;

[0064] R a Each is independently selected from H and C. 1-3 Alkyl, C 1-3 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a' replace;

[0065] R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2;

[0066] R c Each is independently selected from H and C. 1-4 alkyl;

[0067] In one embodiment of the invention, a compound or a salt thereof of formula (I) shown above is provided, wherein:

[0068] R1 is selected from C 1-8 Alkyl, C 1-8 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a replace;

[0069] R2 and R3 are each independently selected from H;

[0070] R4 and R5 are each independently selected from H;

[0071] Ring A and ring B are each independently selected from C. 6-10 Aryl;

[0072] R6 and R7 are each independently selected from H, phenyl, and C. 1-5 Alkyl, C 1-5 Alkyl and phenyl groups are each optionally marked with 0, 1, 2 or 3 R groups. c replace;

[0073] m can be 0, 1, 2, or 3;

[0074] n is 0, 1, 2, or 3;

[0075] R a Each is independently selected from H and C. 1-3 Alkyl, C 1-3 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a' replace;

[0076] R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2;

[0077] R c Each is independently selected from H and C. 1-4 alkyl;

[0078] In one embodiment of the invention, a compound or a salt thereof of formula (I) shown above is provided, wherein:

[0079] R1 is selected from C 1-8 Alkyl, C 1-8 Alkyl groups are optionally enclosed by one or two R groups. a replace;

[0080] R2 and R3 are each independently selected from H;

[0081] R4 and R5 are each independently selected from H;

[0082] Ring A and ring B are each independently selected from phenyl, naphthyl, and pyridyl, wherein at least one of ring A or ring B is selected from phenyl and naphthyl;

[0083] R6 and R7 are each independently selected from H, phenyl, and C. 1-5 Alkyl, C 1-5 Alkyl and phenyl groups are each optionally marked with 0, 1, 2 or 3 R groups. c replace;;

[0084] m can be 0, 1, 2, or 3;

[0085] n is 0, 1, 2, or 3;

[0086] R a Each is independently selected from H and C. 1-3 Alkyl, C 1-3 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a' replace;

[0087] R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2;

[0088] R c Each is independently selected from H and C. 1-4 alkyl;

[0089] In one embodiment of the invention, a compound or a salt thereof of formula (I) shown above is provided, wherein:

[0090] R1 is selected from C 1-8 Alkyl, C 1-8 Alkyl groups are optionally enclosed by one or two R groups. a replace;

[0091] R2 and R3 are each independently selected from H;

[0092] R4 and R5 are each independently selected from H;

[0093] Ring A and ring B are each independently selected from phenyl and naphthyl groups;

[0094] R6 and R7 are each independently selected from H, phenyl, and C. 1-5 Alkyl, C 1-5 Alkyl and phenyl groups are each optionally marked with 0, 1, 2 or 3 R groups. c replace;;

[0095] m can be 0, 1, 2, or 3;

[0096] n is 0, 1, 2, or 3;

[0097] R a Each is independently selected from H and C. 1-3 Alkyl, C1-3 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a' replace;

[0098] R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2;

[0099] R c Each is independently selected from H and C. 1-4 alkyl;

[0100] In one embodiment of the invention, a compound or a salt thereof of formula (I) shown above is provided, wherein:

[0101] R1 is selected from C 1-8 Alkyl, C 1-8 Alkyl groups are optionally enclosed by one or two R groups. a replace;

[0102] R2 and R3 are each independently selected from H;

[0103] R4 and R5 are each independently selected from H;

[0104] Ring A and ring B are each independently selected from phenyl groups;

[0105] R6 and R7 are each independently selected from H, phenyl, and C. 1-5 Alkyl, C 1-5 Alkyl and phenyl groups are each optionally marked with 0, 1, 2 or 3 R groups. c replace;;

[0106] m can be 0, 1, 2, or 3;

[0107] n is 0, 1, 2, or 3;

[0108] R a Each is independently selected from H and C. 1-3 Alkyl, C 1-3 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a' replace;

[0109] R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2;

[0110] R c Each is independently selected from H and C. 1-4 alkyl;

[0111] This invention also provides compounds of the following formula or salts thereof.

[0112]

[0113]

[0114] Some solutions in this invention are derived from arbitrary combinations of the above-mentioned variables.

[0115] In some embodiments of the present invention, the above-mentioned compounds or their salts are used as UVB ultraviolet absorbers in the anti-photoaging of polymeric materials.

[0116] Technical effect

[0117] The triazine compounds proposed in this invention, which do not contain ortho-hydroxyl groups, have an absorption range covering the 250nm–315nm wavelength range sensitive to C,C bonds in polymer materials. They also exhibit high transmittance to long-wave ultraviolet light, low chromaticity, and good stability. These compounds can be used in polymer materials requiring high transparency to improve their weather resistance.

[0118] Definitions and Explanations

[0119] Unless otherwise stated, the following terms and phrases as used herein are intended to have the following meanings. A particular term or phrase should not be considered uncertain or unclear unless specifically defined, but should be understood in its ordinary sense. When a trade name appears herein, it is intended to refer to the corresponding product or its active ingredient.

[0120] The terms “optional” or “optionally” refer to events or conditions that may occur but are not required to occur as described below, and the description includes both cases where said events or conditions occur and cases where said events or conditions do not occur.

[0121] The term "substituted" refers to the substitution of one or more hydrogen atoms on a particular atom by a substituent, which can include deuterium and hydrogen variants, provided that the valence state of the particular atom is normal and the substituted compound is stable.

[0122] The term "optionally substituted" means that it may or may not be substituted, unless otherwise specified, and the type and number of substituents may be arbitrary on the basis of chemical feasibility.

[0123] When any variable (e.g., R) appears more than once in the composition or structure of a compound, its definition is independent in each case. For example, if a group is substituted by 0-2 Rs, the group may optionally be substituted by at most two Rs, and R has independent options in each case. Furthermore, combinations of substituents and / or their variants are only permitted if such combinations produce stable compounds.

[0124] Unless otherwise specified, when a group has one or more connectable sites, any one or more sites of that group can be connected to other groups by chemical bonds. When the chemical bond connection is non-directional and the connectable site contains H atoms, the number of H atoms at that site will decrease accordingly with the number of chemical bonds connected, resulting in a group with the corresponding valence.

[0125] Unless otherwise specified, the term "C1-3 alkyl" is used to denote a straight-chain or branched saturated hydrocarbon group consisting of 1 to 3 carbon atoms. The C1-3 alkyl group includes C1-2 and C2-3 alkyl groups, etc.; it can be monovalent (e.g., methyl), divalent (e.g., methylene), or polyvalent (e.g., methine). Examples of C1-3 alkyl groups include, but are not limited to, methyl (Me), ethyl (Et), propyl (including n-propyl and isopropyl), etc.

[0126] Unless otherwise specified, the term "C1-4 alkyl" is used to denote a straight-chain or branched saturated hydrocarbon group consisting of 1 to 4 carbon atoms. The C1-4 alkyl group includes C1-2, C1-3, and C2-3 alkyl groups, etc.; it can be monovalent (e.g., methyl), divalent (e.g., methylene), or polyvalent (e.g., methine). Examples of C1-4 alkyl groups include, but are not limited to, methyl (Me), ethyl (Et), propyl (including n-propyl and isopropyl), butyl, etc.

[0127] Unless otherwise specified, the term "C1-5 alkyl" is used to denote a straight-chain or branched saturated hydrocarbon group consisting of 1 to 5 carbon atoms. The C1-5 alkyl group includes C1-4, C1-3, C1-2, C2-5, C2-4, and C5 alkyl groups, etc.; it can be monovalent (e.g., methyl), divalent (e.g., methylene), or polyvalent (e.g., methine). Examples of C1-5 alkyl groups include, but are not limited to, methyl (Me), ethyl (Et), propyl (including n-propyl and isopropyl), butyl (including n-butyl, isobutyl, s-butyl, and t-butyl), pentyl (including n-pentyl, isopentyl, and neopentyl), etc.

[0128] Unless otherwise specified, the term "C1-8 alkyl" is used to denote a straight-chain or branched saturated hydrocarbon group consisting of 1 to 8 carbon atoms. The C1-8 alkyl group includes C1-7, C1-6, C1-5, C1-4, C1-3, C1-2, C7, C6, and C5 alkyl groups, etc.; it can be monovalent (e.g., methyl), divalent (e.g., methylene), or polyvalent (e.g., methine). Examples of C1-8 alkyl groups include, but are not limited to, methyl (Me), ethyl (Et), propyl (including n-propyl and isopropyl), butyl (including n-butyl, isobutyl, s-butyl, and t-butyl), pentyl (including n-pentyl, isopentyl, and neopentyl), hexyl, heptyl, octyl, etc.

[0129] Unless otherwise specified, "C2-6 alkenyl" is used to denote a straight-chain or branched hydrocarbon group consisting of 2 to 6 carbon atoms containing at least one carbon-carbon double bond, which can be located at any position on the group. The C2-6 alkenyl group includes C6, C5, C4, C3, and C2 alkenyl groups; the C2-6 alkenyl group can be monovalent, divalent, or polyvalent. Examples of C2-6 alkenyl groups include, but are not limited to, vinyl and propenyl groups.

[0130] Unless otherwise specified, the term "5-6 membered heterocyclic alkenyl" alone, or in combination with other terms, refers to a partially unsaturated cyclic group consisting of 5 to 6 ring atoms comprising at least one carbon-carbon double bond, wherein 1, 2, 3, or 4 of the ring atoms are heteroatoms independently selected from O, S, and N, and the remainder are carbon atoms, wherein the nitrogen atom is optionally quaternized, and the nitrogen and sulfur heteroatoms may optionally be oxidized (i.e., NO and S(O)p, where p is 1 or 2). It includes monocyclic and bicyclic systems, wherein bicyclic systems include spirocyclic, fused, and bridged rings, and any ring in this system is non-aromatic. Furthermore, with respect to the "5-6 membered heterocyclic alkenyl," the heteroatom may occupy the linking position between the heterocyclic alkenyl and the rest of the molecule. The 5-6 membered heterocyclic alkenyl includes 5-membered and 6-membered heterocyclic alkenyl groups, etc.

[0131] Unless otherwise specified, "C3-5 cycloalkyl" refers to a saturated cyclic hydrocarbon group consisting of 3 to 5 carbon atoms, including monocyclic, bicyclic, and tricyclic systems, wherein bicyclic and tricyclic systems include spirocyclic, fused, and bridged rings. The C3-5 cycloalkyl group includes a C3-4 ring; it can be monovalent, divalent, or polyvalent. Examples of C3-5 cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, and cyclopentyl.

[0132] Unless otherwise specified, the term "3-7 membered heterocyclic alkyl" or in combination with other terms refers to a saturated cyclic group consisting of 3 to 7 ring atoms, wherein 1, 2, or 3 of the ring atoms are heteroatoms independently selected from O, S, and N, and the remainder are carbon atoms, wherein the nitrogen atom is optionally quaternized, and the nitrogen and sulfur heteroatoms may optionally be oxidized (i.e., NO and S(O)p, where p is 1 or 2). It includes monocyclic and bicyclic systems, wherein bicyclic systems include spirocyclic, fused, and bridged rings. Furthermore, with respect to the term "3-7 membered heterocyclic alkyl," the heteroatom may occupy the connection position between the heterocyclic alkyl group and the rest of the molecule. The 3-7 membered heterocyclic alkyl group includes 4-6, 5-6, 4, 5, and 6 membered heterocyclic alkyl groups, etc. Examples of 3-7 membered heterocyclic alkyl groups include, but are not limited to, azirrobutyl, oxoheterobutyl, thioheterobutyl, pyrrolidinyl, pyrazolyl, imidazoalkyl, tetrahydrothiopheneyl (including tetrahydrothiophene-2-yl and tetrahydrothiophene-3-yl, etc.), tetrahydrofuranyl (including tetrahydrofuran-2-yl, etc.), tetrahydropyranyl, piperidinyl (including 1-piperidinyl, 2-piperidinyl and 3-piperidinyl, etc.), piperazinyl (including 1-piperazinyl and 2-piperazinyl, etc.), etc.

[0133] Unless otherwise specified, the term "C6-10 aryl" refers to a cyclic hydrocarbon group consisting of 6 to 10 carbon atoms with a conjugated π-electron system. It can be a monocyclic, fused bicyclic, or fused tricyclic system, wherein each ring is aromatic. It can be monovalent, divalent, or polyvalent, and C6-10 aryl includes C6-9, C9, C10, and C6 aryl groups. Examples of C6-10 aryl groups include, but are not limited to, phenyl and naphthyl groups (including 1-naphthyl and 2-naphthyl groups).

[0134] Unless otherwise specified, the term "6-8-membered heteroaryl" in this invention refers to a cyclic group consisting of 6 to 8 ring atoms with a conjugated π-electron system, wherein 1, 2, 3, 4, or 5 of the ring atoms are heteroatoms independently selected from O, S, N, P, or Se, and the remainder are carbon atoms. It can be a monocyclic, fused bicyclic, or fused tricyclic system, wherein each ring is aromatic. The nitrogen atom is optionally quaternized, and the nitrogen and sulfur heteroatoms may optionally be oxidized (i.e., NO, S(O)p, and P(O)p, where p is 1 or 2). The 6-8-membered heteroaryl can be attached to the rest of the molecule via heteroatoms or carbon atoms. The 6-8-membered heteroaryl includes 6-7-membered, 6-membered, and 7-membered heteroaryl groups, etc. Examples of the 6-8-membered heteroaryl include, but are not limited to, pyrroleyl (including N-pyrroleyl, 2-pyrroleyl, and 3-pyrroleyl, etc.) and pyrazolyl (including 2-pyrazolyl and 3-pyrazolyl, etc.).

[0135] Unless otherwise specified, the term "5-10-membered heteroaryl" in this invention refers to a cyclic group consisting of 5 to 10 ring atoms with a conjugated π-electron system, wherein 1, 2, 3, or 4 ring atoms are heteroatoms independently selected from O, S, N, P, or Se, and the remainder are carbon atoms. It can be a monocyclic, fused bicyclic, or fused tricyclic system, wherein each ring is aromatic. The nitrogen atom is optionally quaternized, and the nitrogen and sulfur heteroatoms may optionally be oxidized (i.e., NO, S(O)p, and P(O)p, where p is 1 or 2). The 5-10-membered heteroaryl can be attached to the rest of the molecule via heteroatoms or carbon atoms. The 5-10-membered heteroaryl includes 5-8-membered, 5-7-membered, 5-6-membered, 5-membered, and 6-membered heteroaryls, etc. Examples of the 5-10 membered heteroaryl groups include, but are not limited to, pyrrole (including N-pyrrole, 2-pyrrole, and 3-pyrrole, etc.), pyrazolyl (including 2-pyrazolyl and 3-pyrazolyl, etc.), imidazole (including N-imidazolyl, 2-imidazolyl, 4-imidazolyl, and 5-imidazolyl, etc.), oxazolyl (including 2-oxazolyl, 4-oxazolyl, and 5-oxazolyl, etc.), triazolyl (1H-1,2,3-triazolyl, 2H-1,2,3-triazolyl, 1H-1,2,4-triazolyl and 4H-1,2,4-triazolyl, etc.), tetrazolyl, isoxazolyl (3-isooxazolyl, 4-isooxazolyl, and 5-isooxazolyl, etc.), and thiazolyl (including 2-thiazolyl, 4-... Thiazolyl and 5-thiazolyl, etc.), furanyl (including 2-furanyl and 3-furanyl, etc.), thienyl (including 2-thienyl and 3-thienyl, etc.), pyridyl (including 2-pyridyl, 3-pyridyl and 4-pyridyl, etc.), pyrazinyl, pyrimidinyl (including 2-pyrimidinyl and 4-pyrimidinyl, etc.), benzothiazolyl (including 5-benzothiazolyl, etc.), purinyl, benzimidazolyl (including 2-benzimidazolyl, etc.), benzoxazolyl, indole (including 5-indole, etc.), isoquinolinyl (including 1-isoquinolinyl and 5-isoquinolinyl, etc.), quinoxalinyl (including 2-quinoxalinyl and 5-quinoxalinyl, etc.), or quinolinyl (including 3-quinolinyl and 6-quinolinyl, etc.). The compounds of the present invention can be prepared by a variety of synthetic methods known to those skilled in the art, including the specific embodiments listed below, embodiments formed by combining them with other chemical synthetic methods, and equivalent substitutions known to those skilled in the art. Preferred embodiments include, but are not limited to, the embodiments of the present invention. Attached Figure Description

[0136] Figure 1 The ultraviolet absorption spectrum of compound 1 prepared in Example 1 of the present invention is shown.

[0137] Figure 2 This is the ultraviolet absorption spectrum of compound 5 prepared in the comparative example of the present invention. Detailed Implementation

[0138] The present invention will be described in detail below with reference to embodiments, but this does not imply any adverse limitation on the invention. The present invention has been described in detail, and specific embodiments thereof have been disclosed. It will be apparent to those skilled in the art that various changes and modifications can be made to the specific embodiments of the present invention without departing from the spirit and scope thereof.

[0139] Example 1

[0140]

[0141] Step 1: Synthesis of Compounds 1-2

[0142] Benzamidine hydrochloride (15.6 g, 100 mmol) and p-hydroxybenzaldehyde (6.1 g, 50 mmol) were added to a 250 mL three-necked flask, and then dissolved in toluene (150 mL). Sodium carbonate (10.6 g, 100 mmol) and copper acetate (2 g, 10 mmol) were added as catalysts. The mixture was heated to 100 °C and stirred for 24 h. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the toluene was removed by concentration under reduced pressure to obtain a crude reaction concentrate. The crude reaction concentrate was separated by silica gel column chromatography (n-heptane / ethyl acetate = 20 / 1) to obtain compounds 1-2.

[0143] 1 H NMR (400Hz, CDCl3) δ10.35(1H,s),8.77–8.67(4H,m),8.65–8.58(2H,m),7.75–7.59(6H,m),7.06–6.96(2H,m); ESI-MS C 21 H 15 N3O(m / z): 326.2(M+H) + .

[0144] Step 2: Synthesis of Compound 1

[0145] In a 250 mL three-necked flask, compounds 1-2 (8.1 g, 25 mmol) and potassium carbonate (6.9 g, 50 mmol) were dissolved in 50 mL of N,N-dimethylformamide. The mixture was heated to 80 °C and stirred for 2 h. Then, 10 mL of a solution of bromoisooctane (4.8 g, 25 mmol) in N,N-dimethylformamide was added dropwise, and the mixture was stirred at 80 °C for another 2 h. Another 10 mL of a solution of bromoisooctane (4.8 g, 25 mmol) in N,N-dimethylformamide was added dropwise, and the reaction was continued for 12 h. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature. 200 mL of deionized water was added to the reaction solution, followed by extraction with 300 mL of dichloromethane. The organic phase was washed three times with 200 mL of deionized water. The solvent was removed by concentration under reduced pressure. The mixture was then purified by recrystallization from a dichloromethane / methanol mixture (dichloromethane / methanol volume ratio = 1 / 1) to give compound 1.

[0146] 1 H NMR(400Hz, CDCl3)δ8.76(4H,dd,J=7.8,1.5Hz),8.72(2H,d,J=8.9Hz),7.54–7.58(6H,m),7.05(2H,d,J=8.9 Hz), 3.96 (2H, dd, J = 5.7, 1.0Hz), 1.75–1.80 (1H, m), 1.41–1.57 (4H, m), 1.32–1.39 (4H, m), 0.91–0.98 (6H, m). ESI-MS C 29 H 31 N3O (m / z): 438.6 (M+H) + .

[0147] Example 2

[0148]

[0149] In a 250 mL three-necked flask, compounds 1-2 (8.1 g, 25 mmol) were dissolved in 50 mL of N,N-dimethylformamide solution, followed by the addition of potassium carbonate (6.9 g, 50 mmol). The mixture was heated to 80 °C and stirred for 2 h. Then, 10 mL of tert-butyl bromide (3.9 g, 50 mmol) in N,N-dimethylformamide solution was added dropwise. The mixture was stirred at 80 °C for another 2 h, followed by the addition of 20 mL of tert-butyl bromide (3.9 g, 50 mmol) in N,N-dimethylformamide solution. The mixture was stirred at 80 °C for another 12 h. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature. 200 mL of deionized water was added to the reaction solution, followed by extraction with 300 mL of dichloromethane. The organic phase was washed three times with 200 mL of deionized water. The solvent was removed by concentration under reduced pressure. The mixture was then recrystallized from a dichloromethane / methanol mixture (dichloromethane / methanol volume ratio = 1 / 1) to obtain compound 2.

[0150] 1 H NMR (400Hz, CDCl3) δ8.56 (4H, dd, J = 7.7, 1.5Hz), 7.81 (2H, d, J = 8.7Hz), 7.48 (6H, m), 7.05 (2H, d, J = 8.7Hz), 1.41 (9H, m). ESI-MS C 25 H 23 N3O(m / z): 382.2(M+H) + .

[0151] Example 3

[0152]

[0153] Step 1: Synthesis of compound 3-2

[0154] In a 250 mL three-necked flask, 21.2 g (100 mmol) of 4-tert-butylbenzamide hydrochloride and 6.1 g (50 mmol) of p-hydroxybenzaldehyde were dissolved in 150 mL of toluene. Copper acetate (2 g, 10 mmol) and sodium carbonate (32.5 g, 100 mmol) were then added. The mixture was heated to 100 °C and stirred for 24 h. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the toluene solution was removed by concentration under reduced pressure to obtain a crude reaction product. The crude product was then separated by silica gel column chromatography (n-heptane / ethyl acetate = 25 / 1) to give compound 3-2.

[0155] 1 H NMR (400Hz, CDCl3) δ7.72 (6H, m), 7.48 (4H, d, J = 8.8Hz), 6.77 (2H, d, J = 8.8Hz), 5.37 (1H, q, J = 2.4Hz), 1.36 (18H, s); ESI-MS C29 H 31 N3O(m / z): 438.3(M+H) + .

[0156] Step 2: Synthesis of Compound 3

[0157] In a 250 mL three-necked flask, compound 3-2 (10.9 g, 25 mmol) was dissolved in 50 mL of N,N-dimethylformamide solution, followed by the addition of potassium carbonate (6.9 g, 50 mmol). The mixture was heated to 80 °C and stirred for 2 h. Then, 10 mL of N,N-dimethylformamide solution containing bromoisooctane (4.8 g, 25 mmol) was added dropwise. The mixture was stirred at 80 °C for another 2 h, followed by another 10 mL of N,N-dimethylformamide solution containing bromoisooctane. The mixture was stirred at 80 °C for 12 h. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature. 200 mL of deionized water was added to the reaction mixture, followed by extraction with 300 mL of dichloromethane. The organic phase was washed three times with 200 mL of deionized water. The solvent was removed by concentration under reduced pressure. The crude concentrate was separated by silica gel column chromatography (n-heptane / ethyl acetate = 10 / 1) to obtain compound 3.

[0158] 1 H NMR(400Hz, CDCl3) δ7.58-7.65(6H,m),7.42(4H,dd,J=7.8,1.6Hz),6.91(2H,d,J=8.6Hz),3 .94(2H,dd,J=5.7,1.0Hz),1.61-1.72(1H,m),1.30-1.46(26H,m),0.86-0.93(6H,m).ESI-MS C 37 H 47 N3O(m / z): 550.4(M+H) + .

[0159] Example 4

[0160]

[0161] Step 1: Synthesis of compound 4-2

[0162] In a 250 mL three-necked flask, (1,1'-biphenyl)-4-carbamate (23.2 g, 100 mmol) and p-hydroxybenzaldehyde (6.1 g, 50 mmol) were dissolved in 150 mL of toluene solution. Copper acetate (2 g, 10 mmol) and sodium carbonate (32.5 g, 100 mmol) were then added. The mixture was heated to 105 °C and stirred for 24 h. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the toluene solution was removed by concentration under reduced pressure. The crude product of the concentrated reaction solution was separated by silica gel column chromatography (n-heptane / ethyl acetate = 20 / 1) to give compound 4-2.

[0163] 1 H NMR (400Hz, CDCl3) δ7.65 (4H, d, J = 7.6), 7.51 (6H, d, J = 7.6), 7.49 (4H, d, J = 7.4), 7.35 (6H, m), 6.77 (2H, d, J = 7.5). ESI-MS C 33 H 23 N3O(m / z): 478.2(M+H) + .

[0164] Step 2: Synthesis of Compound 4

[0165] In a 250 mL three-necked flask, compound 4-2 (10.9 g, 25 mmol) was dissolved in 50 mL of N,N-dimethylformamide solution, followed by the addition of potassium carbonate (6.9 g, 50 mmol). The mixture was heated to 80 °C and stirred for 2 h. Then, 10 mL of N,N-dimethylformamide solution containing bromoisooctane (4.8 g, 25 mmol) was added dropwise. The mixture was stirred at 80 °C for another 2 h, followed by the addition of another 10 mL of N,N-dimethylformamide solution containing bromoisooctane. The mixture was stirred at 80 °C for another 12 h. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature. 200 mL of deionized water was added to the reaction solution, followed by extraction with 300 mL of dichloromethane. The organic phase was washed three times with 200 mL of deionized water. The dichloromethane solution was removed by vacuum concentration, and the crude concentrate was separated by silica gel column chromatography (n-heptane / ethyl acetate = 10 / 1) to obtain compound 4.

[0166] 1H NMR(400Hz, CDCl3)δ7.76(4H,dd,J=7.8,1.6Hz),7.62(6H,m),7.54(4H,dJ=7.7),7.48–7.58(6H,m),7.05(2H,d,J =8.7Hz),3.94(2H,dd,J=5.6,1.2Hz),1.73–1.81(1H,m),1.40–1.57(4H,m),1.30–1.39(4H,m),0.91–0.98(6H,m). ESI-MS C 41 H 39 N3O(m / z): 590.3(M+H) + .

[0167] Comparative Example 1

[0168]

[0169] Step 1: Synthesis of Compound 5-2

[0170] Salicylic acid amide (5 g, 36 mmol) and 4-methoxybenzoyl chloride (10 g, 58.8 mmol) were added simultaneously to a three-necked flask, and the mixture was heated to 140 °C and stirred for 3 h. After the reaction was complete, the reaction mixture was cooled to 60 °C, and 120 mL of methanol was added. The mixture was stirred and the temperature was continuously lowered. The temperature was maintained below 30 °C, and the mixture was stirred for 1 h. The product was then filtered to obtain compound 5-2.

[0171] ESI-MS C 15 H 11 NO3 (m / z): 254.2 (M+H) +

[0172] Step 2: Synthesis of Compound 5

[0173] Sodium hydroxide (1.25 g, 31.2 mmol) was weighed into a three-necked flask, and 200 mL of methanol was added. The mixture was stirred until dissolved, then benzoamidine hydrochloride (2.4 g, 15.4 mmol) and compound 5-2 (4 g, 15.8 mmol) were added. The mixture was heated to 60 °C and refluxed with stirring for 3 hours. The mixture was then cooled to room temperature and filtered. The filter cake was washed once with water and once with methanol, and then dried at 60 °C to obtain compound 5.

[0174] 1 H NMR (400Hz, CDCl3) δ 13.42 (1H, s), 8.74 (1H, dd, J = 8.2Hz), 8.64 (4H, dd, J = 7.6Hz), 7.62 (3H, m), 7.50 (1H, m), 7.06 (4H, m), 3.94 (3H, m). ESI-MS C 22 H17 N3O2 (m / z): 356.3 (M+H) + .

[0175] Comparative Example 2

[0176]

[0177] Step 1: Synthesis of Compound 6-2

[0178] 8.3 g (20 mmol) of 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine, 2.4 g (22 mmol) of resorcinol, and 50 mL of chlorobenzene were added in a single batch to a three-necked flask. The mixture was heated to 110 °C and stirred for 3 h. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the reaction mixture was added dropwise to 200 mL of deionized water and filtered to obtain compound 6-2.

[0179] ESI-MS C 33 H 23 N3O2 (m / z): 494.2 (M+H) +

[0180] Step 2: Synthesis of Compound 6

[0181] Compound 6-2 (7.4 g, 15 mmol) and potassium carbonate (4.1 g, 30 mmol) were weighed into a three-necked flask, and 50 mL of N,N-dimethylformamide was added. The mixture was heated to 80 °C and stirred for 2 h. Bromoisooctane (5.8 g, 30 mmol) was added dropwise, and the reaction was monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature. The mixture was extracted with 50 mL of deionized water and 50 mL of dichloromethane. The organic phase was washed three times with 150 mL of deionized water. The solvent was removed by concentration under reduced pressure. Compound 6 was obtained by silica gel column chromatography (petroleum ether / ethyl acetate = 5:1).

[0182] 1 H NMR (400Hz, CDCl3): δ7.65-7.75(4H,m),7.45-7.53(9H,m),7.23-7.38(6H,m),6.91(1H,d,J=7 .2Hz),6.45(1H,s),5.37(1H,s),3.94(2H),1.61-1.73(1H,m),1.29-1.44(8H,m),0.89(6H,s). ESI-MS C 41 H 39 N3O2 (m / z): 606.6 (M+H) + .

[0183] Comparative Example 3

[0184]

[0185] Step 1: Synthesis of Compound 7-2

[0186] 7.58 g (20 mmol) of 2,4-bis(4-(tert-butyl)phenyl)-6-chloro-1,3,5-triazine, 2.4 g (22 mmol) of resorcinol, and 50 mL of chlorobenzene were added in one batch to a three-necked flask. The mixture was heated to 110 °C and stirred for 3 h. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the reaction mixture was added dropwise to 200 mL of deionized water and filtered to obtain compound 7-2.

[0187] ESI-MS C 29 H 31 N3O2 (m / z): 454.6 (M+H) +

[0188] Step 2: Synthesis of Compound 7

[0189] Compound 7-2 (6.8 g, 15 mmol) and potassium carbonate (4.1 g, 30 mmol) were weighed and placed in a three-necked flask. 50 mL of N,N-dimethylformamide was added, and the mixture was heated to 80 °C and stirred for 2 h. Bromoisooctane (4.1 g, 30 mmol) was added dropwise, and the reaction was monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature. The mixture was extracted with 50 mL of deionized water and 50 mL of dichloromethane. The organic phase was washed three times with 150 mL of deionized water. The solvent was removed by concentration under reduced pressure. Compound 7 was obtained by silica gel column chromatography (petroleum ether / ethyl acetate = 4:1).

[0190] 1H NMR (400Hz, CDCl3): δ7.51(5H,m),7.42(4H,m),6.91(1H,d,J=7.2Hz),6.45(1H,s ),5.37(1H,s),3.94(2H,s),1.72(1H,m),1.29-1.44(28H),0.89(6H,m).ESI-MSC 37 H 47 N3O2 (m / z): 566.4 (M+H) + .

[0191] Comparative Example 4

[0192]

[0193] Step 1: Synthesis of Compound 8-2

[0194] 7.25 g (20 mmol) of 2,4-diphenyl-6-chloro-1,3,5-triazine, 2.43 g (22 mmol) of resorcinol, and 100 mL of chlorobenzene were added simultaneously to a three-necked flask. The mixture was heated to 110 °C and stirred for 3 h. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the reaction mixture was added dropwise to 200 mL of deionized water and filtered to obtain compound 8-2.

[0195] ESI-MS C 21 H 15 N3O2 (m / z): 342.37 (M+H) +

[0196] Step 2: Synthesis of Compound 8

[0197] Compound 8-2 (5.5 g, 15 mmol) and potassium carbonate (3.3 g, 30 mmol) were weighed and placed in a three-necked flask. 50 mL of N,N-dimethylformamide was added, and the mixture was heated to 80 °C and stirred for 2 h. Bromoisooctane (3.3 g, 30 mmol) was added dropwise, and the reaction was monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature. The mixture was extracted with 50 mL of deionized water and 50 mL of dichloromethane. The organic phase was washed three times with 150 mL of deionized water. The solvent was removed by concentration under reduced pressure. Compound 8 was obtained by silica gel column chromatography (petroleum ether / ethyl acetate = 3:1).

[0198] 1 H NMR(400Hz, CDCl3) δ8.66(4H,m),7.61(1H,d,J=7.6Hz),7.35–7.48(6H,m),6.91(1H,d,J=7.6Hz),6.48(1H,s),5.3 8(1H,s),3.96(2H,d,J=2.4Hz),1.75–1.80(1H,m),1.41–1.57(4H,m),1.32–1.39(4H,m),0.91–0.98(6H,m).ESI-MS C 29 H 31 N3O2 (m / z): 454.58 (M+H) + .

[0199] Comparative Example 5

[0200]

[0201] Step 1: Synthesis of Compound 9-2

[0202] 2,4-Diphenyl-6-chloro-1,3,5-triazine (6.25 g, 20 mmol), resorcinol (2.20 g, 22 mmol), and chlorobenzene (80 mL) were added in a single batch to a three-necked flask. The mixture was heated to 110 °C and stirred for 3 h. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the reaction mixture was added dropwise to 150 mL of deionized water and filtered to obtain compound 9-2.

[0203] ESI-MS C 21 H 15 N3O2 (m / z): 342.37 (M+H) +

[0204] Step 2: Synthesis of Compound 9

[0205] Compound 9-2 (4.25 g, 15 mmol) and potassium carbonate (2.6 g, 30 mmol) were weighed and placed in a three-necked flask. 50 mL of N,N-dimethylformamide was added, and the mixture was heated to 80 °C and stirred for 2 h. Tert-butyl bromide (2.6 g, 30 mmol) was added dropwise, and the reaction was monitored by thin-layer chromatography. After the reaction was complete, the mixture was cooled to room temperature. The mixture was extracted with 80 mL of deionized water and 80 mL of dichloromethane. The organic phase was washed three times with 150 mL of deionized water. The solvent was removed by concentration under reduced pressure. Compound 9 was obtained by silica gel column chromatography (petroleum ether / ethyl acetate = 2:1).

[0206] 1 H NMR (400Hz, CDCl3) δ8.56(4H,m),7.56(1H,d,J=8.7Hz),7.05-7.35(6H,m),6.95(1H,d,J=8.7Hz)6.54(1H,s),5.37(1H,s),1.41(9H,s). ESI-MS C 25 H 23 N3O(m / z): 398.2(M+H) + .

[0207] Test Example: Ultraviolet Absorption Performance Test

[0208] Test method: Compounds 1, 2, 3, 4 and 5-9 were dissolved in tetrahydrofuran at a concentration of 0.1 mg / mL, and the ultraviolet-visible absorption spectra were measured on an ultraviolet spectrophotometer (Easy UV).

[0209] Test results: Figure 1 This is a UV absorption performance test graph of compound 1 prepared in Example 1 of the present invention. Figure 2 This is a side view showing the UV absorption performance of compound 5 in Comparative Example 1. Compounds 2-4, prepared in other specific embodiments of the present invention, have similar properties to... Figure 1Compounds 6-9, prepared in other comparative examples, exhibit similar absorption properties to those of compounds 6-9. Figure 2 Similar absorption performance; detailed absorption data are shown in Table 1.

[0210] Table 1. UV absorption properties of the compounds in the examples and comparative examples.

[0211] Example / Comparative Example Number Compound numbering Maximum ultraviolet absorption wavelength Example 1 Compound 1 271nm, 306nm Example 2 Compound 2 271nm, 307nm Example 3 Compound 3 272nm, 306nm Example 4 Compound 4 315nm Comparative Example 1 Compound 5 277, 325nm Comparative Example 2 Compound 6 330nm Comparative Example 3 Compound 7 325nm Comparative Example 4 Compound 8 272, 338nm Comparative Example 5 Compound 9 272, 337nm

[0212] Conclusion: The UV absorption performance test data shows that compounds 1-4 can absorb UVB ultraviolet light, with the maximum absorption wavelength located in the range of 250nm to 320nm, and almost no absorption after 330nm, exhibiting high transmittance for long-wave ultraviolet light. Comparative compounds 5-9 have a wide UV absorption range, covering the long-wave ultraviolet wavelength range, resulting in low transmittance for long-wave ultraviolet light.

[0213] Depend on Figure 1 Based on the test data of compounds 1 and 8 in Table 1, it can be seen that the maximum ultraviolet absorption wavelength of compound 1 is located at 271 nm and 306 nm, while the maximum ultraviolet absorption wavelength of compound 8, when an ortho-hydroxyl group is present, is located at 272 nm and 338 nm. Compound 1 shows almost no absorption after 330 nm. Compound 1 can absorb mid-wave ultraviolet light, but has almost no absorption for long-wave ultraviolet light, exhibiting high transmittance for long-wave ultraviolet light.

[0214] Depend on Figure 2 Based on the test data of compounds 2, 5, and 9 in Table 1, it can be seen that the maximum ultraviolet absorption wavelength of compound 2 is located at 271 nm and 306 nm; the maximum ultraviolet absorption wavelength of compound 5 is located at 277 nm and 325 nm; and the maximum ultraviolet absorption wavelength of compound 9 is located at 272 nm and 337 nm. The ultraviolet absorption wavelength range of compound 2 covers the mid-wave band, and it can completely absorb mid-wave ultraviolet light. It has almost no absorption in the long-wave band, and long-wave ultraviolet light can pass through it. When an ortho-hydroxyl group is present, compound 5 has a wider absorption range in the long-wave band, but its long-wave transmittance is not high. The maximum ultraviolet absorption wavelength of compound 9 is located in the long-wave band, and it has strong absorption of long-wave ultraviolet light, but its long-wave ultraviolet transmittance is not high.

[0215] As shown in Table 1, the test data of compounds 3 and 7 indicate that the maximum ultraviolet absorption wavelengths of compound 3 are located at 272 nm and 306 nm, while the maximum ultraviolet absorption wavelength of compound 7 is located at 325 nm. The ultraviolet absorption wavelength range of compound 3 covers the mid-wave ultraviolet band, and it can completely absorb mid-wave ultraviolet light. However, its absorption intensity for long-wave ultraviolet light is weak, and it can transmit almost all long-wave ultraviolet light. In the presence of an ortho-hydroxyl group, the maximum ultraviolet absorption wavelength of compound 7 is located at 325 nm. It has a wider absorption range in the long-wave band and strong absorption for long-wave ultraviolet light, but its long-wave ultraviolet transmittance is not high.

[0216] As shown in Table 1, the maximum ultraviolet absorption wavelength of compound 4 is 315 nm, and that of compound 6 is 330 nm. The ultraviolet absorption wavelength range of compound 4 covers the mid-wave ultraviolet band and can completely absorb mid-wave ultraviolet light. However, it has weak absorption intensity for long-wave ultraviolet light and can transmit almost all long-wave ultraviolet light. In contrast, when an ortho-hydroxyl group is present, compound 6 has strong absorption for long-wave ultraviolet light. Although it can absorb mid-wave ultraviolet light, its long-wave ultraviolet light transmittance is low.

[0217] In summary, compared with the comparative compounds 5-9, the compounds 1-4 of the present invention absorb only in the low and medium wavelength range and have almost no absorption in the long wavelength range, showing excellent long-wave ultraviolet transmittance. In practical applications (such as photovoltaics and agricultural films), the high transmittance of compounds 1-4 in the long-wave ultraviolet range is beneficial to the utilization of long-wave ultraviolet light by the material.

[0218] Although the above embodiments have provided a detailed description of the present invention, they are only some embodiments of the present invention and not all embodiments. People can obtain other embodiments based on these embodiments without creative effort, and these embodiments all fall within the protection scope of the present invention.

Claims

1. A compound of formula (I) or a salt thereof, in, R1 is independently selected from C 1-8 Alkyl and C 2-6 alkenyl, the C 1-8 Alkyl and C 2-6 The alkenyl group can be optionally surrounded by 1, 2, or 3 R groups. a replace; R2 and R3 are each independently selected from H, F, Cl, Br, -CN, -NH2, and -SR. b and -S(=O)2R b ; R4 and R5 are each independently selected from H, F, Cl, Br and CN; Ring A and ring B are each independently selected from C. 6-10 aryl, 5-6 membered heterocyclic alkenyl and 5-10 membered heteroaryl, wherein at least one of ring A or ring B is selected from C. 6-10 Aryl; R6 and R7 are each independently selected from H, F, Cl, Br, -CN, NH2, phenyl, and C. 1-5 Alkyl, the C 1-5 Alkyl and phenyl groups are each optionally marked with 0, 1, 2 or 3 R groups. c replace; m can be 0, 1, 2, or 3; n is 0, 1, 2, or 3; R a Each is independently selected from H, F, Cl, Br, -CN, -NH2, C 1-3 Alkyl, C 3～5 Cycloalkyl and 3-7 membered heterocycloalkyl, wherein C 1-3 Alkyl, C 3～5 Cycloalkyl and 3-7 membered heterocycloalkyl groups are each optionally surrounded by 1, 2 or 3 R groups. a' replace; R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2; R b Each is independently selected from -CH3, -CH2CH3, and -CH2CH2CH3; R c Each is independently selected from H, F, Cl, Br, -CN, -NH2, and C. 1-4 alkyl; The 3-7-membered heterocyclic alkyl, 5-6-membered heterocyclic alkenyl and 5-10-membered heteroaryl groups each independently comprise 1, 2 or 3 atoms or groups independently selected from N, O, S and NH; The condition is that the compound or its salt described in formula (I) is not selected from:

2. The compound or its salt according to claim 1, characterized in that, The R1 is selected from -CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -(CH2)4CH3, -(CH2)5CH3, -(CH2)3CH(CH3)2, -CHCH2, -CH2CHCH2, and -(CH2)2CHCH2, wherein -CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -(CH2)4CH3, -(CH2)5CH3, -(CH2)3CH(CH3)2, -CHCH2, -CH2CHCH2, and -(CH2)2CHCH2 are each selected by 1, 2, or 3 R1s. a replace.

3. The compound or its salt according to claim 1, characterized in that, R6 and R7 are independently selected from H, F, Cl, Br, -CN, NH2, -CH3, -CH2CH3, -CH(CH3)2, -(CH2)2CH3, -(CH2)3CH3, -C(CH3)3, and phenyl, respectively, wherein -CH3, -CH2CH3, -CH(CH3)2, -(CH2)2CH3, -(CH2)3CH3, -C(CH3)3, and phenyl are each optionally selected by 1, 2, or 3 R6 and R7. c replace.

4. The compound or its salt according to claim 1, characterized in that, Ring A and ring B are each independently selected from The Each can be replaced by either m R6s or n R7s.

5. The compound or its salt according to claim 1, characterized in that, structure Selected from 6. The compound or its salt according to claim 1, characterized in that, structure Selected from 7. The compound of formula (I) or a salt thereof according to claim 1, characterized in that: in, R1 is selected from C 1-8 Alkyl, C 1-8 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a replace; R2 and R3 are each independently selected from H, F, Cl, Br, -CN, -NH2, and -SR. b and -S(=O)2R b ; R4 and R5 are each independently selected from H, F, Cl, Br and CN; Ring A and ring B are each independently selected from C. 6-10 aryl and 5-10 heteroaryl, wherein at least one of ring A or ring B is selected from C. 6-10 Aryl; R6 and R7 are each independently selected from H, F, Cl, Br, -CN, NH2, phenyl, and C. 1-5 Alkyl, C 1-5 Alkyl and phenyl groups are each optionally marked with 0, 1, 2 or 3 R groups. c replace; m can be 0, 1, 2, or 3; n is 0, 1, 2, or 3; R a Each is independently selected from H, F, Cl, Br, -CN, -NH2, C 1-3 Alkyl, C 3～5 Cycloalkyl and 3-7 membered heterocycloalkyl, C 1-3 Alkyl, C 3～5 Cycloalkyl and 3-7 membered heterocycloalkyl groups are each optionally surrounded by 1, 2 or 3 R groups. a' replace; R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2; R b Each is independently selected from -CH3, -CH2CH3, and -CH2CH2CH3; R c Each is independently selected from H, F, Cl, Br, -CN, -NH2, and C. 1-4 alkyl.

8. The compound of formula (I) or a salt thereof according to claim 7, characterized in that: in, R1 is selected from C 1-8 Alkyl, C 1-8 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a replace; R2 and R3 are each independently selected from H, F, Cl, Br, -CN and -NH2; R4 and R5 are each independently selected from H, F, Cl, Br and CN; Ring A and ring B are each independently selected from C. 6-10 aryl and 6-8 membered heteroaryl, wherein at least one of ring A or ring B is selected from C. 6-10 Aryl; R6 and R7 are each independently selected from H, F, Cl, Br, -CN, NH2, phenyl, and C. 1-5 Alkyl, phenyl and C 1-5 Each alkyl group is optionally surrounded by 0, 1, 2 or 3 R's. c replace; m can be 0, 1, 2, or 3; n is 0, 1, 2, or 3; R a Each is independently selected from H, F, Cl, Br, -CN, -NH2, and C. 1-3 Alkyl, C 1-3 Alkyl groups may be optionally surrounded by 1, 2, or 3 R's. a' replace; R a' Each is independently selected from H, F, Cl, Br, -CN, and -NH2; R c Each is independently selected from H, F, Cl, Br, -CN, -NH2, and C. 1-4 alkyl.

9. The compound of formula (I) according to claim 1, or a salt thereof, selected from the following compounds or salts thereof, 10. The application of the compound or its salt according to any one of claims 1-9 as a UVB ultraviolet absorber with high UVA transmittance in the anti-photoaging of polymer materials.

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