New polycyclic compounds

Abstract

To provide a novel polycyclic compound which can be used as a light conversion agent, a dye, a pigment, a fluorescent agent or an ultraviolet or blue light absorber and to provide a method for synthesizing the same and use of the same.SOLUTION: There is provided a compound represented, for example, by the following compound (7), which contains a plurality of carbon rings and / or a heterocyclic ring structure and has a visible light or fluorescent emitting group in which at least one UV light and / or blue light absorbing group are covalently bonded to provide stability. The compound can be used for a product such as an optical film, an agricultural film, an optical disc (compact disc), an optical lense, a goggle, a skin care product, a color cosmetic, an illumination tool, a coating material, an adhesive, a light stabilizer or a panel as a light conversion agent, a dye, a pigment, a fluorescent agent or an ultraviolet or blue light absorber.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates to novel polycyclic compounds, their synthesis and their use. The compounds of the present invention contain multiple carbon rings and / or heterocyclic ring structures, have groups that emit visible light or fluorescence, and are covalently bound to at least one ultraviolet light and / or blue light absorbing group for stability. The compounds of the present invention can be used as light conversion agents, dyes, pigments, fluorescent agents, ultraviolet light or blue light absorbing agents in products such as optical films, agricultural films, optical discs (compact discs), optical lenses, goggles, skin care products, color cosmetics, lighting tools, paints, adhesives, light stabilizers, or panels. [Background technology]

[0002] Currently, organic compounds having luminescent properties, such as dyes, pigments or fluorescent substances, are widely used in the fields of agriculture, electronics and medicine, for example as light conversion agents or optical recording media for optical discs.

[0003] In agriculture, adding a light conversion agent to an agricultural film can convert ultraviolet light or short-wavelength blue light in sunlight into light useful to plants. Of these, red light is the most important light for the growth of agricultural crops, and contributes to increased production of agricultural crops. For example, in the early heading of Chinese cabbage, red light promotes the heading of the leaves, but excessive blue light inhibits heading (Non-Patent Document 1). In addition, prior literature discloses that the commercial organic light conversion agent RL1000 (Compound A, BASF) used in agricultural films can absorb ultraviolet light to reduce pests such as aphids and emit visible light (about 635 nm) that is advantageous to plants, but is insufficiently stable (Patent Document 1). [ka]

[0004] In general, organic compounds such as the organic light conversion agent RL1000 are prone to decomposition when used outdoors, so improving stability is an important indicator for improving light conversion agents.

[0005] On the other hand, in existing optical recording media such as optical disks, a laser beam is irradiated onto an organic dye in a recording layer, and the laser light is converted into thermal energy in a short time, causing thermal deformation of the recording layer, for example, to a molten state, and information is recorded by the difference in reflectance to light between the deformed and undeformed parts. Since high local temperatures of 250°C or more occur due to the conversion of the laser light into thermal energy, the melting point and thermal stability of the dye are considered to be important requirements. Although a prior document discloses an organic compound (B) for use in optical recording media (Patent Document 2), it has a low melting point and lacks stability. [ka]

[0006] It is also known that irradiation with ultraviolet light and / or blue light is an important cause of decomposition of organic materials, such as agricultural films or optical recording media. Although the shelf life of agricultural films or optical discs can be extended by blocking ultraviolet light or blue light or adding a blue light blocking agent and / or an ultraviolet light blocking agent, conventional blue light blocking agents only have the function of blocking both blue light and long-wavelength ultraviolet light (UVA). If it is necessary to block both blue light and long-wavelength and short-wavelength ultraviolet light (UVA+UVB), an additional ultraviolet light absorber (UVB) must be added, which is not suitable for industrial application. Therefore, the development of a compound whose absorption wavelength band covers ultraviolet light (UVA+UVB) and blue light is a goal being pursued in this industry.

[0007] In view of the above, improving the stability of dyes and photoconversion agents for luminescent recording media, and developing compounds whose absorption wavelength range covers ultraviolet light (UVA+UVB) and blue light, are both goals being pursued in the industry. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Chinese Patent No. 100500754 [Patent Document 2] Patent No. 3876970 [Non-patent literature]

[0009] [Non-Patent Document 1] Journal of Agricultural Machinery, ISSN: 1019-0430, Vol 8 (2), 1999 Jun, p.63-74 Summary of the Invention [Problem to be solved by the invention]

[0010] The development of highly stable organic dyes, photoconversion agents, or compounds whose absorption wavelength bands cover ultraviolet light (UVA+UVB) and blue light has been a goal that has been pursued in the industry for some time. In order to achieve this goal, the present inventors have specifically designed novel polycyclic compounds represented by formula (1) and formula (2). [Means for solving the problem]

[0011] The compounds of the present invention represented by formula (1) and formula (2) are based on the design concept of covalently bonding a dye or a photoconverting material with an ultraviolet light and / or blue light absorbing material. The compounds of formula (1) or formula (2) designed based on this new concept not only significantly improve the stability of conventional organic dyes or photoconverting agents, but also improve the stability of the organic materials to be protected due to their broad-spectrum blocking effect against blue light and ultraviolet light (UVA+UVB).

[0012] This may be because the covalently bonded UV light absorbing group provides stability to the photoconverter itself from a short distance within the molecule. In addition, the UV light absorbing group also provides stability to the organic material surrounding the molecule that is to be protected, such as agricultural films. As a result of this dual action, the service life and stability of the agricultural film are significantly increased.

[0013] Currently, the organic light conversion agent A (RL1000, BASF) used in agricultural films can emit orange-red light under sunlight, but its photostability is insufficient. When used in outdoor PE agricultural films, RL1000 can only remain stable for two seasons. [ka]

[0014] The inventors have covalently bonded it with benzotriazole to obtain MP259 (Compound 7), which can provide outdoor stability for PE agricultural films for more than three seasons (Example 43).

[0015] The melting point of the organic dye compound (B) used in the optical recording medium was 175° C., but by covalently bonding with benzotriazole, the melting point was increased to 224° C. (Example 41), which is an important, unexpected, and surprising improvement. [ka]

[0016] The organic dye in the optical disc absorbs the laser light and converts it into thermal energy, resulting in high local temperatures of over 250°C. By covalently bonding compound (B) with benzotriazole, not only is the melting point and thermal stability improved, but the shelf life of the optical disc is also extended due to the ultraviolet light (UVA+UVB) absorption ability provided by benzotriazole.

[0017] Preferably, the compounds of the present invention improve the stability without impairing the inherent luminescent properties of the organic dye or photoconverter.

[0018] More preferably, the structure of R1 to R3 in the compound of formula (1) or formula (2) is designed to increase or decrease the conjugation, thereby increasing or decreasing the inherent luminescence characteristics of the organic dye or light conversion agent. For example, the compound (19) in Example 11 has increased conjugation compared to the compound (18), while the wavelength of visible light absorbed or emitted is also increased. The application field can be expanded from dyes to other fields, such as agricultural films. In addition, the highly stable compound (7) can be applied to agricultural films as well as red laser light (640 nm) commonly used in DVD-R optical discs.

[0019] In addition, the compound of the present invention can also be used as an ultraviolet light and / or blue light absorber. Since the compound of the present invention has luminescent properties, it can be used as an ultraviolet light absorber and / or blue light absorber with a special color. Conventional blue light blocking / absorbing agents can only absorb ultraviolet light (UVA) and blue light. On the other hand, since the compound of the present invention has a wide range of ultraviolet light (UVA+UVB) absorbing properties, it can simultaneously absorb ultraviolet light (UVA+UVB) and blue light without adding an additional ultraviolet light (UVB) absorber, and can fully protect the human body, polymers, or other organic materials.

[0020] The compounds provided by the present invention are polycyclic compounds and have a structure represented by formula (1) or formula (2). [ka] [ka]

[0021] The constituent fragments A, B, C, and D of the compound represented by formula (1) or formula (2) of the present invention are all the same, but differ only in the order of rings C and D. The compounds of formula (1) and formula (2) of the present invention have a single property.

[0022] The compound of the present invention represented by formula (1) or (2) is at least one visible or fluorescent light emitting group and at least one other ultraviolet light absorbing group; During the ceremony, [ka] or [ka] is a visible light emitting group or a fluorescent light emitting group, [ka] is an ultraviolet light absorbing group, R1 to R3 are a single bond or / and any divalent linking group. Preferably, R1 is a single bond or any divalent linking group. More preferably, R1 is a single bond and a divalent linking group. For example, [ka] is 9-hydrocarbazole or dibenzothiophene, A, B, and C are 5-7 membered rings unsubstituted or substituted by R4, preferably benzene ring, benzocarbocycle, 5-7 membered nitrogen-containing heterocycle, or 5-7 membered nitrogen-containing benzoheterocycle, where the nitrogen-containing heterocycle does not exclude other heteroatoms, and the 5-7 membered nitrogen-containing benzoheterocycle means a condensation of a benzene ring and a 5-7 membered nitrogen-containing heterocycle; D is an unsubstituted or substituted 5-7 membered heterocycle or 5-7 membered benzoheterocycle consisting of carbon, nitrogen, oxygen and sulfur atoms, where the substituents of the carbon atoms of the ring are selected from one or more of H, hydroxyl, oxo, thiol, amino, imino, linear or branched C1-C8 alkyl groups, and R4, and the substituents of the nitrogen atoms of the ring are selected from one or more of H, hydroxyl, oxo and linear or branched C1-C8 alkyl groups; R4 is one or more substituents (in the structural formula of the present invention, the substitution position of R4 or other substituents is not fixed, which means that it can be substituted at any position of the ring. For example, in the structural formula, when the bonding position of R4 in the ring is between two atoms, it means that R4 can be bonded at any position of the ring), and each independently is hydrogen, halogen, hydroxyl group, amino group, nitro group, cyano group, linear or branched C1-C 18 Alkyl, alkenyl or alkoxy groups, substituted or unsubstituted phenyl groups, SR5, SO2R5, SO3R 5、 selected from COOR5, COR5, OCOR5, C(O)NR6R7, SO2NR6R7, and NR6R7, where R5, R6, and R7 are each independently selected from hydrogen, a straight-chain or branched C1-C8 alkyl group, and R4 and its adjacent R4, or R4 and its adjacent ring, can both represent a fused carbocyclic or fused heterocyclic ring of 3-6 atoms, preferably a fused heterocyclic ring of 3-6 atoms containing one or more of C, N, O, and S, and preferably the halogen is chlorine.

[0023] Preferably, R1 to R3 are a single bond, or -O-, -S-, -C(=O)-, -COO-, -C(=S)-, -C(=NR 13 )-, -N(R 13 )-, -C(R 14 )(R 15 )-, -C(R 16 )=, -C≡, -C(R 17 )=C(R 18 R is a chain consisting of 1-10 groups selected from -Ph-, ... 13 ~R 18is one or more and each is independently selected from hydrogen, halogen, a hydroxyl group, a linear or branched C1-C6 alkyl group (preferably a C1-C4 alkyl group) which is unsubstituted or substituted with a halogen, and a phenyl group which is unsubstituted or substituted with a halogen or a C1-C6 alkyl group (preferably a C1-C4 alkyl group). Ph is a phenyl group which is unsubstituted or substituted with a halogen, an OH group, or a linear or branched C1-C6 alkyl group (preferably a C1-C4 alkyl group), and preferably the halogen is chlorine.

[0024] A is, [ka] Selected from A is substituted with one or more R4 or Ph, where p=0-3, preferably p=0-2, and the substituent R4 is one or more and each is independently selected from hydrogen, halogen, nitro group, cyano group, linear or branched C1-C8 alkyl group, alkenyl group or alkoxy group, SR5, SO2R5, COOR5, COR5, C(O)NR6R7, and NR6R7, where R5, R6, and R7 are each independently selected from hydrogen, linear or branched C1-C8 alkyl group, preferably R5, R6, and R7 are hydrogen or linear or branched C1-C4 alkyl group, and preferably halogen is chlorine. Ph is an unsubstituted or substituted phenyl group, preferably a phenyl group substituted with a halogen, a hydroxy group, a C1-C6 alkoxy group (preferably a C1-C4 alkoxy group) or a C1-C6 alkyl group (preferably a C1-C4 alkyl group), and preferably the halogen is chlorine. 19 ~R 20 is one or more and each is independently selected from hydrogen, a linear or branched C1-C6 alkyl group (preferably a C1-C4 alkyl group), and an unsubstituted or substituted phenyl group, and preferably the substituent is a halogen or a linear or branched C1-C6 alkyl group (preferably a C1-C4 alkyl group).

[0025] B is, [ka] Selected from C is [ka] Selected from.

[0026] D is [ka] Selected from In the formula, p=0 to 3, preferably p=0 to 2, n=0 to 1, and X1 to X6 each independently represent C=O, C=S, C=N-R8, N, NR9, C, O, S, CR 10 , C.R. 11 R 12 , CNR 11 R 12 , and C.R. 10 NR 11 R 12 where R8 to R 12 is one or more and each independently selected from hydrogen, linear or branched C1-C8 alkyl or alkenyl groups, and unsubstituted or linear or branched C1-C6 alkyl groups (preferably C1-C4 alkyl groups) or phenyl groups substituted with halogen, and ring D is unsubstituted or substituted with R4 and is linked to the exocyclic ring via one or two double or single bonds. Preferably, ring D is linked to the exocyclic ring via a double bond. Preferably, the halogen is chlorine.

[0027] More preferably, R1 to R3 are a single bond, or / and -O-, -C(=O)-, -COO-, -N(R 13 )-, -C(R 14 )(R 15 )-, -C(R 16 )=, -C(R 17 )=C(R 18 )-, -Ph-, and -Ph-. Where R 13 ~R 18is one or more and each is independently selected from H, a straight or branched chain C1-C6 alkyl group (preferably a C1-C4 alkyl group) which is unsubstituted or substituted with a halogen, and a phenyl group which is unsubstituted or substituted with a halogen or a C1-C6 alkyl group (preferably a C1-C4 alkyl group). Ph is a phenyl group which is unsubstituted or substituted with a halogen, an OH group or a C1-C6 alkyl group (preferably a C1-C4 alkyl group), and preferably the halogen is chlorine.

[0028] A is, [ka] Selected from p=0 to 2; R4 is one or more substituents, each independently selected from hydrogen, halogen, nitro group, cyano group, linear or branched C1-C8 alkyl group, alkenyl group or alkoxy group, SR5, SO2R5, COOR5, COR5, C(O)NR6R7, and NR6R7, where R5, R6, and R7 are each independently selected from hydrogen, linear or branched C1-C8 alkyl group. Preferably, R5, R6, and R7 are hydrogen or linear or branched C1-C4 alkyl group, and preferably, the halogen is chlorine. Ph is an unsubstituted or R4-substituted phenyl group, and preferably, the substituent is hydrogen, halogen, OH group, C1-C6 alkoxy group (preferably, C1-C4 alkoxy group) or phenyl group substituted with C1-C6 alkyl group (preferably, C1-C4 alkyl group), and preferably, the halogen is chlorine; B is, [ka] Selected from C is [ka] Selected from D is [ka] Selected from In the formula, when n=0, X1 is selected from C=O and C=S, and X2, X3, and X4 are each independently C=O, C=S, C=N-R8, or C-NR 11 R 12 , N, NR9, C, O, S, CR 10 , and C.R. 11 R 12 Selected from When n=1, X4 and X6 are each independently selected from C=O and C=S, and X1, X2, and X3 are each independently selected from C=O, C=S, C=N-R8, N, NR9, C, O, S, CR 10 , C.R. 11 R 12 , and C-NR 11 R 12 Selected from R8 to R 12 is one or more and each independently selected from H, a linear or branched C1-C6 alkyl group (preferably a C1-C4 alkyl group), and a phenyl group unsubstituted or substituted with a halogen or a C1-C6 alkyl group (preferably a C1-C4 alkyl group). Ring D is unsubstituted or substituted with R4 and is linked to the exocyclic ring via 1 to 2 double bonds or single bonds. Preferably, ring D is linked to the exocyclic ring via a double bond.

[0029] More preferably, R2 is a single bond or -(CHR 21 ) q N(R 22 )-, where R 21 , R 22 are each independently selected from hydrogen, a linear or branched C1-C8 alkyl group (preferably a C1-C4 alkyl group), and an unsubstituted phenyl group or a phenyl group substituted with a C1-C6 alkyl group (preferably a C1-C4 alkyl group), where q=0-18, preferably q=0-8, more preferably q=0-4, particularly preferably q=0-2, and most preferably q=1; D is the following ring: [ka] [ka] Selected from In the formula, the substituent R4 is one or more, and each independently selected from hydrogen, halogen, linear or branched C1-C8 alkyl group, alkenyl group, or alkoxy group (preferably, C1-C6 or C1-C4 alkyl group, alkenyl group, or alkoxy group), SR5, SO2R5, COOR5, COR5, C(O)NR6R7, and NR6R7, where R5, R6, and R7 are each independently selected from hydrogen, linear or branched C1-C6 alkyl group (preferably, C1-C4 alkyl group), preferably, halogen is chlorine, p=0-2, preferably, p=0-1, and particularly preferably, p=0, R9, R 23 ~R 34 is selected from hydrogen, a straight or branched chain C1 to C6 alkyl group (preferably a C1 to C4 alkyl group), and an unsubstituted phenyl group or a phenyl group substituted with a C1 to C6 alkyl group (preferably a C1 to C4 alkyl group).

[0030] Particularly preferably, [ka] is the following group: [ka] Selected from R4 is one or more substituents, each of which is independently hydrogen, halogen, a hydroxyl group, an amino group, a nitro group, a cyano group, a linear or branched C1-C 18 Alkyl, alkenyl or alkoxy groups, substituted or unsubstituted phenyl groups, SR5, SO2R5, SO3R 5、selected from COOR5, COR5, OCOR5, C(O)NR6R7, SO2NR6R7, and NR6R7, where R5, R6, and R7 are each independently selected from hydrogen, a straight or branched C1-C8 alkyl group (preferably a C1-C4 alkyl group), and R4 and its adjacent R4, or R4 and its adjacent ring, can both represent a fused carbocyclic or fused heterocyclic ring of 3-6 atoms, preferably a fused heterocyclic ring of 3-6 atoms containing C, N, O, and S, and preferably, the halogen is chlorine, and p=0-2, preferably p=0-1, and more preferably p=0.

[0031] R 19 , R 35 ~R 39 is one or more and each independently selected from H, a linear or branched C1-C6 alkyl group (preferably a C1-C4 alkyl group), and a phenyl group unsubstituted or substituted with a halogen or a C1-C6 alkyl group (preferably a C1-C4 alkyl group), and Ph is a phenyl group unsubstituted or substituted with a halogen, an OH group, or a C1-C6 alkyl group (preferably a C1-C4 alkyl group), and preferably the halogen is chlorine.

[0032] Very particularly preferably, the compound of formula (1) or formula (2) comprises at least one visible light or fluorescent light emitting group and at least one covalently bound ultraviolet light absorbing group, wherein the visible light or fluorescent light emitting group is [ka] or [ka] and [ka] Selected from D is [ka] [ka] Selected from During the ceremony, [ka] is an ultraviolet light absorbing group, and [ka] [ka] [ka] Selected from The visible light (fluorescence) emitting group or ultraviolet light absorbing group is (R4). p In the formula, p is 0 to 3, preferably p is 0 to 1, and particularly preferably p is 0. R4 is one or more substituents, each of which is independently hydrogen, halogen, a hydroxyl group, an amino group, a nitro group, a cyano group, a linear or branched C1 to C 18 selected from an alkyl group, an alkenyl group or an alkoxy group, a substituted or unsubstituted phenyl group, SR5, SO2R5, SO3R5, COOR5, COR5, OCOR5, C(O)NR6R7, SO2NR6R7, and NR6R7, where R5, R6, and R7 are each independently selected from hydrogen, a linear or branched C1-C8 alkyl group (preferably a C1-C4 alkyl group), and R4 and its adjacent R4, or R4 and its adjacent ring, can both represent a fused carbocyclic or fused heterocyclic ring of 3-6 atoms, preferably a fused heterocyclic ring of 3-6 atoms containing one or more of C, N, O, and S; 40 ~R 49 are the same or different and are each independently selected from hydrogen, a linear or branched C1-C8 alkyl or alkenyl group (preferably a C1-C4 alkyl or alkenyl group), and an unsubstituted or linear or branched C1-C6 alkyl group (preferably a C1-C4 alkyl group), or a phenyl group substituted with halogen; R 50is selected from hydrogen, a monovalent metal, a linear or branched C1-C8 alkyl or alkenyl group (preferably a C1-C4 alkyl group), and an unsubstituted or linear or branched C1-C6 alkyl group (preferably a C1-C4 alkyl group) or a phenyl group substituted with a halogen. Preferably, the halogen is chlorine. Preferably, the monovalent metal is lithium or sodium.

[0033] Most preferably, the compound of formula (1) or formula (2) is: [ka] [ka] [ka]

[0034] The method for producing the compound of formula (1) or formula (2) is a method characterized by comprising any one of the following reaction steps:

[0035] The preparation of the compounds of formula (1) comprises any of the following reaction steps: [ka] The preparation of the compound of formula (2) comprises any of the following reaction steps: [ka] In the formula, rings A to D and R1 to R3 are as defined above. D' is a precursor of the D ring, [ka] Selected from D" is a precursor of the D ring and has the formula [ka] and Z is a leaving group, halogen, C1-C10 Sulfonate ester group, C1-C 10 Preferably, Z is selected from halogen, p-toluenesulfonate esters (OTs), mesylates (OMs), and C1-C4 alkoxy groups, including but not limited to alkoxy groups. Preferably, the halogen is chlorine.

[0036] U and V are C=O, C=S, and C=NR 51 , and C(R 52 )(R 53 ) and R 50 ~R 53 are the same or different and each independently selected from a single bond, hydrogen, and a linear or branched C1 to C8 alkyl group, preferably the alkyl group is a linear or branched C1 to C4 alkyl group.

[0037] T may be the same or different and each T is independently selected from NH, NH2, OH, and SH.

[0038] Specific production method 1 of compound (1) of the present invention includes the production methods of Examples 1-11, 15-22, and 33. Among them, the production method of the compound of Example 1-4 is as follows. [ka]

[0039] Specific examples of the production method 2 of the compound (1) of the present invention include the production methods of Examples 12-14 and 23-32. Among them, the production method of Example 13 is as follows. [ka]

[0040] A specific example of the production method 1 of the compound (2) of the present invention includes the production method of Example 34, and the production method is as follows. [ka]

[0041] A specific example of the production method 2 of the compound (2) of the present invention includes the production method of Example 35, and the production method is as follows. [ka]

[0042] A specific example of the production method 3 of the compound (2) of the present invention includes the production method of Example 36, and the production method is as follows. [ka]

[0043] A specific example of the production method 4 of the compound (2) of the present invention includes the production method of Example 37, and the production method is as follows. [ka]

[0044] A specific example of the production method 5 of the compound (2) of the present invention includes the production method of Example 38, and the production method is as follows. [ka]

[0045] A specific example of the production method 6 of the compound (2) of the present invention includes the production method of Example 39, and the production method is as follows. [ka]

[0046] The specific method for preparing conventional benzotriazole compounds generally uses 2-nitroaniline and various substituted phenols as starting materials for synthesis. For example, as shown in Example 6, an azo compound is formed in the first step, and a reduction reaction is carried out in the second step to form a benzotriazole compound (US3773751). The preparation method is as follows: [ka]

[0047] The compounds of the present invention can be used in films, for example, as light conversion agents in agricultural films. They can also be used in ultraviolet light blocking films or blue light blocking films for the purpose of protecting the eyes and other tissues. The compounds of the present invention can also be used in general films or organic materials for the purpose of protecting the film or organic material itself. As another example, the compounds of the present invention can be used in the recording layer of optical recording media. The compounds of the present invention can be used in combination with other compounds according to different requirements. Industrially common methods can be used to implement these applications.

[0048] Agricultural films are generally manufactured by adding auxiliary agents to resin raw materials such as polyvinyl chloride, ethylene or low-density polyethylene (LDPE), ethylene-vinyl acetate copolymer (EVA), and metallocene linear polyethylene (MLLDPE), followed by blow molding and rolling processes. A specific manufacturing method is, for example, to uniformly mix 1 kg of low-density polyethylene as a base material, 200 g of metallocene linear polyethylene, 5 g of light conversion agent, 8 g of antioxidant, 5 g of ultraviolet light absorber, and 9 g of glycerin, and then blow molding is performed as usual using an inflation molding device to obtain a transparent film with a thickness of 0.03 to 2.0 mm. The amount of light conversion agent added depends on the type of agricultural crop and the thickness of the agricultural film, and a typical range includes, but is not limited to, 0.001% to 20%, and is preferably 0.2% to 5%.

[0049] In the manufacture of ultraviolet light blocking films, blue light blocking films, or agricultural films, the light conversion composition or blue light blocking composition may be applied to a base layer or a release layer for use after curing. Alternatively, the composition may be applied to a release film first and then transferred to the base layer using a transfer coating process. A release film is attached to each of the upper and lower layers of the film, and is an OCA Optically Clear Adhesive. The coating method may be a conventionally known coating method such as brush coating, spray coating, curtain coating, roll coating, slit coating, air knife coating, blade coating, and metaling bar coating. The drying method may include natural drying, microwave drying, ultraviolet drying, infrared drying, and hot air drying. The base layer may include one or more mixtures of polyester, glass, polyethylene, polypropylene, polycarbonate, polyamide, polyacrylate, polymethacrylate, polyvinyl acetate, and polyvinyl chloride. The release film may include a silicone compound and a non-silicone compound material. The composition of the light conversion composition or the blue light blocking composition includes the light conversion agent of the present invention, the ultraviolet light blocking agent or the blue light blocking agent, a polymer, a solvent, and / or an auxiliary agent, and / or an initiator, and / or a monomer.

[0050] When the compound of the present invention is used in the recording layer of an optical recording medium, the organic dye recording layer may be coated on a substrate by spin coating. The substrate may be made of polycarbonate (PC) or polyacrylamine material. The thickness of the recording layer is generally several nanometers to several tens of nanometers. After coating, a reflective layer is formed on the recording layer by sputtering, and then an adhesive layer is spin coated, and a cover plate is attached to the reflective layer by the adhesive layer to form an optical disk. [Brief description of the drawings]

[0051] [Figure 1] 1 is a UV-VIS absorption pattern (10 mg / tetrahydrofuran) of compound (7) of the present invention. [Diagram 2] 1 is a TGA (thermal analyzer) pattern of compound (7) of the present invention. [Diagram 3]1 is a UV-VIS absorption pattern (10 mg / tetrahydrofuran) of compound (18) of the present invention. [Figure 4] 1 shows the appearance of an agricultural film produced using the light conversion agent of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0052] Specific embodiments of the present invention will be described below, but the present invention is not limited to these embodiments.

[0053] [ka]

[0054] Table 1 shows compounds of formula (1). [Table 1(1)] [Table 1(2)] [Table 1(3)] [Table 1(4)]

[0055] [ka]

[0056] Table 2 shows compounds of formula (2). [Table 2]

[0057] Example 1 Preparation of 2-(2-hydroxy-3-(chloromethyl)-5-methyl)benzotriazole (compound 4) [ka]

[0058] 350g of 2-(2-hydroxy-5-methyl)benzotriazole (UV-P, compound 3), 55g of paraformaldehyde, 2000g of acetic acid, and 300g of 35% hydrochloric acid are added to a 5000ml reaction flask, heated to 60°C, and reacted for 10 hours while maintaining the temperature. Samples are taken to monitor the reaction. After cooling, washing with water, and drying, a white powder (chloromethyl UV-P, compound 4) is obtained in a 96% yield. Its chemical formula is C 14 H 12 ClN3O, melting point is 163-164°C.

[0059] Example 2 Preparation of 2-(2-hydroxy-3-(N,N-dimethylaniline)-5-methyl)benzotriazole (compound 5) [ka]

[0060] Add 180 ml of toluene, 17 g of potassium carbonate, 13.9 g of N-methylaniline, 0.2 g of phase catalyst, and 33.3 g of compound (4), heat to 90-100°C, react for 5 hours, and sample to monitor the reaction. Cool to 30°C, wash with water to recover toluene, add 180 g of methanol, stir, filter, and dry to obtain a solid (compound 5) with a purity of 98.3% and a yield of 84%. Its chemical formula is C 21 H 20 N4O, melting point is 98-100℃.

[0061] Example 3 Preparation of 2-(2-hydroxy-3-(4-formyl-N,N-dimethylaminophenyl)-5-methyl)benzotriazole (Compound 6) [ka]

[0062] Add 35 g of compound (5) and 8.7 g of DMF, and while maintaining the temperature at 20-25°C, dropwise add 18.4 g of phosphorus oxychloride over a period of about 2 hours. Heat to 90°C and react for 2 hours, sampling to monitor the reaction (Vilsmeier-Haack formulation). The reactants are slowly added to 300 g of water at 30°C or lower to hydrolyze, and after the addition is complete, neutralize with 30% liquid alkali, adjust the pH to 8, and filter and separate the solid. Dissolve in toluene, wash with water, cool to 15°C, precipitate the solid, and dry to obtain 31.8 g of a yellow solid (compound 6). Its chemical formula is C 21 H 19 N4O2, melting point is 111-113℃.

[0063] Example 4 Preparation of 5-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(methyl)amino)benzylidene)pyrimidine-2,4-,6(1H,3H,5H)trione (Compound 7) [ka]

[0064] Dissolve 50g of compound (6) and 17.1g of barbituric acid in toluene, add 5g of ammonium acetate and 10g of acetic acid, and react for 1 hour while maintaining the temperature at 80-90℃. Then, raise the temperature to reflux and react for 8 hours, sample to monitor the reaction, and after the reaction is completed, cool, filter and separate the solid, wash with toluene, then wash with dichloroethane, filter, wash with water, and dry to obtain solid compound (7). The yield is about 80%, and the chemical formula is C 26 H 22 N6O4, melting point is 262-270℃.

[0065] Example 5 Preparation of 5-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(ethyl)amino)benzylidene)pyrimidine-2,4-,6(1H,3H,5H)trione (Compound 8) [ka]

[0066] Compound 8 is obtained by following the procedure of Example 1-4, except that N-ethylaniline is used instead of N-methylaniline. Its chemical formula is C 27 H 24 N6O4, melting point is 263-267℃.

[0067] Example 6 Preparation of 5-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-(2-methylheptan-2-yl)benzyl)(ethyl)amino)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (Compound 9) [ka]

[0068] The raw material 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole (compound 10) is obtained from Eutec co. (Eusorb 329, melting point 102-106°C) or prepared by the following method. 13.8g of o-nitroaniline is added to 25ml of 37% hydrochloric acid, stirred, diluted with 40ml of water and cooled to -15°C. 7.5g of sodium nitrite (aqueous solution) is added and the temperature is maintained at 0-5°C to obtain the diazonium salt. 5.2g of 4-tert-octylphenol, 20ml of petroleum ether, 5ml of water and 2.5g of calcium hydroxide are mixed, and the reaction is monitored by sampling. After the reaction is complete, 20g of ice is added and the temperature is raised to 0°C. The diazonium salt is added and stirred for 2 hours. After neutralization with concentrated hydrochloric acid and drying, 2-((2-nitrophenyl)diazenyl)-4-(2,4,4-trimethylpentan-2-yl)phenol (compound 11) is obtained. Its chemical formula is C 20 H 25 N3O3, melting point is 114-115℃.

[0069] Dissolve 35.7 g of compound (11) in 100 ml of petroleum ether, add 17.2 g of zinc and 100 ml of water. Add 41.6 g of NaOH solution (25%) at 50°C within 4 hours and leave for 1 hour. Add 100 ml of concentrated hydrochloric acid and leave for 2 hours, sample to monitor the reaction, wash the organic layer with water, remove the solvent to obtain compound 10, whose chemical formula is C 20 H 25 N3O, melting point 102-106℃. [ka]

[0070] Compound (9) was obtained in the same manner as in Example 1-5, except that 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole (Eusorb 329, compound 10) was used instead of UV-P (compound 3) as the starting material. The chemical formula of the compound (9) is C 34 H 38 N6O4, m / z is 594.3[M] + It is.

[0071] Example 7 Preparation of 5-(4-((3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxybenzyl)(ethyl)amino)benzylidene)pyrimidine-2,4-,6(1H,3H,5H)trione (Compound 12) [ka]

[0072] The procedure of Example 6 is repeated except that 4-chloro-2-nitroaniline is used instead of o-nitroaniline as the starting material to obtain 2-(2'-hydroxy-phenyl)-5-chloro-benzotriazole (compound 13), whose chemical formula is C. 12 H8ClN3O, melting point 139-140°C. Compound 12 is obtained in the same manner as in Example 1-5, except that 2-(2'-hydroxy-phenyl)-5-chloro-benzotriazole (compound 13) is used instead of UV-P (compound 3) as the starting material. Its chemical formula is C26 H 21 ClN6O4, m / z is 516.1[M] + It is.

[0073] Example 8 Preparation of 5-(4-((3-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxybenzyl)(ethyl)amino)benzylidene)pyrimidine-2,4-,6(1H,3H,5H)trione (Compound 14) [ka]

[0074] The procedure of Example 6 is repeated except that 4-methoxy-2-nitroaniline is used instead of o-nitroaniline as the starting material to obtain 2-(2'-hydroxy-phenyl)-5-chloro-benzotriazole (compound 15), whose chemical formula is C. 14 H 13 N3O2, melting point 126-127°C. Compound 14 is obtained in the same manner as in Example 1-5, except that 2-(2'-hydroxy-phenyl)-5-methoxy-benzotriazole (compound 15) is used instead of UV-P (compound 3) as the starting material. Its chemical formula is C 28 H 26 N6O5, m / z is 526.2[M] + It is.

[0075] Example 9 Preparation of 3-(2H-benzo[d][1,2,3]triazol-2-yl)-5-((ethyl(4-((2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl)phenyl)amino)methyl)-4-hydroxybenzoate (Compound 16) [ka]

[0076] The procedure of Example 6 was repeated except that 4-hydroxybenzoic acid was used instead of 4-tert-octylphenol to obtain 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxybenzoic acid. Thionyl chloride was added and the mixture was refluxed for 2 hours, after which the thionyl chloride was evaporated to dryness, and n-hexanol was added and refluxed. The reaction was monitored by sampling to obtain hexyl 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxybenzoate (compound 17). Its chemical formula is C 19 H 21 N3O3, melting point is 83-84℃. [ka]

[0077] Compound (16) is obtained in the same manner as in Example 1-5, except that hexyl 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxybenzoate (compound 17) is used instead of UV-P (compound 3) as the starting material. The chemical formula of the compound (16) is C 33 H 34 N6O6, m / z is 610.3 [M] + It is.

[0078] Example 10 Preparation of 5-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(ethyl)amino)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (Compound 18) [ka]

[0079] In toluene, 20 g of compound (6) and 8.2 g of Meldrum's acid are added to 4.1 g of ammonium acetate and 10 g of acetic acid. The reaction is refluxed for 4 hours, and the reaction is monitored by sampling. After the reaction is complete, the solid is separated by filtration, dissolved in dichloroethane by heating, washed with water, distilled off the dichloroethane, and recrystallized by adding toluene to obtain compound (18). Its chemical formula is C 29 H 28 N4O5, melting point is 220-224℃.

[0080] Example 11 Preparation of 5-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(ethyl)amino)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (Compound 19) [ka]

[0081] Add 12 g of compound (6) to 200 ml of a solution consisting of 1% sodium hydroxide and 15% ethanol. Add 5 g of 30% acetaldehyde aqueous solution dropwise. Allow to react overnight, add 15 g of NaCl, stir, and adjust the pH to neutral with dilute hydrochloric acid. Then, extract with ethyl acetate and dry to obtain 3-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(ethyl)amino)phenyl)acrylaldehyde (20). [ka]

[0082] Then, in the same manner as in Example 10, compound (20) is added to Meldrum's acid, ammonium acetate and acetic acid, and reacted to obtain compound (19), whose chemical formula is C 31 H 30 N4O5, m / z is 538.2 [M] + It is.

[0083] Example 12 Preparation of 5-(4-(methylamino)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (compound 21) [ka]

[0084] Dissolve 20g of barbituric acid and 13.6g of 4-methylaminobenzaldehyde in dichloromethane. Add molecular sieves to remove water, and attach a calcium chloride tube to make it waterproof. Add 1ml of piperidine and 0.6ml of acetic acid, heat to reflux and react for 2 hours. Add new molecular sieves during the reaction, and sample to monitor the reaction. After the reaction is completed, remove the solvent, wash with acid, and dry to obtain compound (21). Its chemical formula is C 12 H 11 N3O3, m / z is 245.1 [M] + It is.

[0085] Example 13 Preparation of 5-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(methyl)amino)benzylidene)pyrimidine-2,4-,6(1H,3H,5H)trione (Compound 7) [ka]

[0086] Compound (7) is obtained in the same manner as in Example 2, except that compound (21) is used instead of N-methylaniline. The reaction is complete when (-CH2Cl) disappears at chemical shift 4.6 in H1-NMR of raw material compound (4) and (compound 7, -CH2N) is newly generated at chemical shift 5.0. The melting point range is the same as that of compound (7) produced by the method of Example 4.

[0087] Example 14 Preparation of ethyl 3-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(methyl)amino)phenyl)-2-cyano-3-phenylacrylate (compound 22) [ka]

[0088] Compound (24) is obtained in the same manner as in Example 2, except that 4-methylaminobenzophenone (compound 23) is used instead of N-methylaniline. [ka]

[0089] Then, in the same manner as in Example 4, compound (24) is used instead of compound (6), and separated by column chromatography to obtain compound (22), whose chemical formula is C 32 H 26 N6O4, m / z is 558.2[M] + It is.

[0090] Example 15 Preparation of 5-((1-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)-1H-indol-3-yl)methylene)pyrimidine-2,4,6-(1H,3H,5H)-trione (compound 25) [ka]

[0091] The same procedure as in Example 3 is repeated except that 3-indolecarbaldehyde is used instead of N-methylaniline, and the resulting mixture is separated by column chromatography to obtain compound (26). Then, the same procedure as in Example 4 is repeated except that compound (26) is used instead of compound (6), and the resulting mixture is separated by column chromatography to obtain compound (25), whose chemical formula is C 27 H 20 N6O4, m / z is 492.2[M]+ It is.

[0092] Here, 3-indolecarbaldehyde is an industrial raw material and can be produced as follows (Vilsmeier reaction). In an ice bath, 16g of POCl3 is dropped into 30g of DMF within 30 minutes. A DMF solution of 11g of an indole compound is gradually added, and the temperature is raised to 35°C and the reaction is stirred for 1 hour. 50g of crushed ice is added to the resulting paste and stirred, and 0.1M NaOH is gradually added while stirring. After washing with water, the mixture is recrystallized with ethanol to obtain 3-indolecarbaldehyde (C9H7NO, melting point 196-197°C).

[0093] Example 16 Preparation of 5-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(methyl)amino)benzylidene)-4-thioxothiazol-2-one (compound 27) [ka]

[0094] The compound (27) is obtained by following the procedure of Example 4, except that the compound 4-thioxothiazol-2-one (CAS RN. 4303-29-1) is used instead of the barbituric acid compound. Its chemical formula is C 25 H 21 N5O4, m / z is 455.2[M] + It is.

[0095] Example 17 Preparation of 5-((6-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(methyl)amino)naphthalen-2-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione (compound 28) [ka]

[0096] The compound (28) is obtained by following the procedure of Example 15, except that 6-(methylamino)-2-naphthaldehyde is used instead of 3-indolecarbaldehyde. The chemical formula of the compound is C 30 H 24 N6O4, m / z is 532.2[M] + It is.

[0097] Example 18 Preparation of 5-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(methyl)amino)benzylidene)oxazolidine-2,4-dione (compound 29) [ka]

[0098] The compound (29) is obtained by following the procedure of Example 4, except that the compound oxazolidine-2,4-dione (CAS RN. 2346-26-1) is used instead of the barbituric acid compound. Its chemical formula is C 25 H 21 N5O4, m / z is 455.2[M] + It is.

[0099] Example 19 Preparation of 2-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(methyl)amino)benzylidene)cyclopent-4-ene-1,3-dione (compound 30) [ka]

[0100] The compound (30) is obtained by the same method as in Example 4, except that 4-cyclopentene-1,3-dione is used instead of barbituric acid. The chemical formula of the compound is C 26 H 19 N4O3, m / z is 435.2[M] + It is.

[0101] Example 20 Preparation of 2-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(methyl)amino)benzylidene)-1H-indene-1,3(2H)-dione (Compound 31) [ka]

[0102] The compound (31) is obtained by following the procedure of Example 4, except that the compound 1H-indene-1,3(2H)-dione is used instead of the barbituric acid compound. The chemical formula of the compound is C 31 H 24 N4O3, m / z is 500.2 [M] + It is.

[0103] Example 21 Preparation of 5-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(methyl)amino)benzylidene)-3,5-dihydro-4H-imidazol-4-one (compound 32) [ka]

[0104] The compound (32) is obtained in the same manner as in Example 4, except that the compound 1,4-dihydroimidazol-5-one (CAS RN.1968-28-1) is used instead of the barbituric acid compound. Its chemical formula is C 25 H 22 N6O2, m / z is 438.2[M] + It is.

[0105] Example 22 Preparation of 4-(4-((3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)(methyl)amino)benzylidene)oxazol-5-(4H)-one (compound 33) [ka]

[0106] The compound (33) is obtained in the same manner as in Example 4, except that the compound 4H-5-oxo-oxazole (CAS RN.497-24-5) is used instead of the barbituric acid compound. Its chemical formula is C 25 H 21 N5O3, m / z is 439.2[M] + It is.

[0107] Example 23 Preparation of 3-(3-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)-5-(tert-butyl)-4-hydroxyphenyl)-N-(4-((2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl)phenyl)propanamide (Compound 34) [ka]

[0108] 5.2 g of 3-(3-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)-5-(tert-butyl)-4-hydroxyphenyl)propionate (compound 35) is dissolved in toluene and heated to reflux in a flask equipped with a condensate removal device. Compound (21) is added to the toluene solution and the reaction is monitored by sampling. After completion of the reaction, the mixture is distilled under vacuum. Compound (34) is obtained by chromatographic separation. Its chemical formula is C 44 H 44 N6O5, m / z is 736.3[M] + It is. [ka]

[0109] The preparation method of compound (35) is as follows (based on CN201710949552.0). Briefly, 16g of 2-chloro-4,6-bis(2',4'dimethyl-phenyl)-1,3,5-triazine (compound 36) and 15g of (3-tert-butyl-4-hydroxyphenyl)propionate (compound 37) are dissolved in 150ml of chlorobenzene, 10g of anhydrous aluminum trichloride is added, and the mixture is stirred under heating to dissolve. The mixture is heated to 90°C and the reaction is monitored by sampling. After the reaction is completed, the mixture is distilled under reduced pressure and separated by chromatography to obtain compound (35). [ka]

[0110] Example 24 Preparation of 5-(4-((3-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)-5-(tert-butyl)-4-hydroxybenzyl)amino)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (compound 38) [ka]

[0111] The product is separated by chromatography in a manner similar to that of Example 13, except that 2-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)-6-(tert-butyl)-4-(chloromethyl)phenol (compound 39) is used instead of compound (4), to give compound (38), whose chemical formula is C 39 H 36 N6O4, m / z is 652.3 [M] + It is. [ka]

[0112] The method for producing compound (39) is the same as the method for producing compound (35) in Example 23, except that 4-(chloromethyl)-2-methylphenol is used instead of (3-(tert-butyl)-4-hydroxyphenyl)propionate (37).

[0113] Example 25 Preparation of 5-(4-((5-benzoyl-4-hydroxy-2-(octyloxy)benzyl)(methyl)amino)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (compound 40) [ka]

[0114] Compound (40) is obtained by chromatographic separation in the same manner as in Example 13, except that (5-(chloromethyl)-2-hydroxy-4-(octyloxy)phenyl)(phenyl)methanone (compound 41) is used instead of compound (4). The chemical formula is C 34 H 37 N3O6, m / z is 583.3 [M] + It is. [ka]

[0115] Compound (41) is produced in the same manner as in Example 1, except that (2-hydroxy-4-(octyloxy)phenyl)(phenyl)methanone (Eutec Co., Eusorb UV-531) is used instead of UV-P (Compound 3).

[0116] Example 26 Preparation of 5-(4-(methyl(4-(4-oxo-4H-benzo[d][1,3]azin-2-yl)benzyl)amino)benzylidene)pyrimidine-2,4,6(1H,3H,5H)trione (compound 42) [ka]

[0117] Compound (42) is obtained by chromatographic separation in the same manner as in Example 13, except that 2-(chloromethyl)-4H-benzo[d][1,3]oxazin-4-one (compound 43) is used instead of compound (4). The chemical formula is C 27 H 20 N4O5, m / z is 480.1 [M] + It is. [ka]

[0118] The method for producing compound (43) is as follows. 14 g of 2-aminobenzoic acid (compound 44) ​​and 11 g of triethylamine are added to 100 ml of dichloroethane, and 19 g of 4-chloromethylbenzoyl chloride (compound 45) is added dropwise and stirred to obtain (compound 43). The method for producing compound (45) is as follows. 4-(hydroxymethyl)benzoic acid (46) is refluxed with thionyl chloride in dichloromethane to obtain compound (45). Its melting point is 28°C. [ka]

[0119] Example 27 Preparation of 5-(4-((4-(((2,4-dihydroxy-quinolin-3-yl)methylene)amino)benzyl)(methyl)amino)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (compound 47) [ka]

[0120] Compound (47) is obtained by following the procedure of Example 13, except that compound (4) is replaced by 3-(((4-(chloromethyl)phenyl)imino)methyl)quinoline-2,4-diol (compound 48). The chemical formula of compound (47) is C. 29 H 23 N5O5, m / z is 521.2 [M] +It is. [ka]

[0121] The method for preparing 3-(((4-(chloromethyl)phenyl)imino)methyl)quinoline-2,4-diol (48) is similar to that of Example 1, except that 3-((phenylimino)methyl)quinoline-2,4-diol (UA-3701, melting point 194° C.) is used instead of UV-P (compound 3).

[0122] Example 28 Preparation of ethyl 4-(((methyl(4-((methyl(4-((2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl)phenyl)amino)methyl)phenyl)amino)methylene)amino)benzoate (Compound 49) [ka]

[0123] Compound (49) is obtained by purification in the same manner as in Example 13, except that ethyl 4-((((4-(chloromethyl)phenyl)(methyl)amino)methylene)amino)benzoate (compound 50) is used instead of compound (4). The chemical formula is C 30 H 29 N5O5, m / z is 539.2 [M] + It is. [ka]

[0124] The method for producing compound (50) is the same as that of Example 1, except that ethyl 4-(((methyl(phenyl)amino)methylene)amino)benzoate (UV-1, melting point 137° C.) is used instead of UV-P (compound 3).

[0125] Example 29 Preparation of N1-(2-ethoxy-4-((methyl(4-((2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl)phenyl)amino)methyl)phenyl)-N2-(2-ethylphenyl)oxamide (compound 51) [ka]

[0126] Compound (51) is obtained by following the procedure of Example 13, except that compound (4) is replaced by N1-(4-(chloromethyl)-2-ethoxyphenyl)-N2-(2-ethylphenyl)oxamide (compound 52). The chemical formula of compound (51) is C 31 H 31 N5O6, m / z is 569.2[M] + It is. [ka]

[0127] The method for preparing N1-(4-(chloromethyl)-2-ethoxyphenyl)-N2-(2-ethylphenyl)oxamide (compound 52) is the same as that of Example 1, except that N-(2-ethoxyphenyl)-N'-(4-ethylphenyl)-ethanediamide (Eutec co., UV-312, melting point 120°C) is used instead of UV-P (compound 3).

[0128] Example 30 Preparation of 5-(4-(((9H-carbazol-3-yl)methyl)(methyl)amino)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (compound 53) [ka]

[0129] Compound (53) is obtained by following the procedure of Example 13, except that 3-(chloromethyl)-9H-carbazole (compound 54) is used instead of compound (4). The chemical formula of compound (53) is C 25 H 20N4O3, m / z is 424.2[M] + It is. [ka]

[0130] The method for producing 3-(chloromethyl)-9H-carbazole (compound 44) ​​is the same as that in Example 1, except that 9H-carbazole is used instead of UV-P (compound 3).

[0131] Example 31 Preparation of 5-(4-(((9H-carbazol-1-yl)methyl)(methyl)amino)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (compound 55) [ka]

[0132] Compound (55) is obtained by the same procedure as in Example 13, except that methyl 9H-carbazole-3-carboxylate (compound 56) is used instead of compound (4). The chemical formula of compound (55) is C 25 H 18 N4O4, m / z is 438.1 [M] + It is. [ka]

[0133] The preparation method of methyl 9H-carbazole-1-carboxylate is as follows: 9H-carbazole-1-carboxylic acid (AKOS BC-1282) is refluxed in excess methanol using concentrated sulfuric acid as a catalyst to obtain compound (56).

[0134] Example 32 Preparation of 5-(4-((dibenzo[b,d]thiophen-2-ylmethyl)(methyl)amino)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (compound 57) [ka]

[0135] Compound (57) is obtained by following the procedure of Example 13, except that 2-(chloromethyl)dibenzo[b,d]thiophene (compound 58) is used instead of compound (4). The chemical formula of compound (57) is C 25 H 19 N3O3S, m / z is 441.1[M] + It is. [ka]

[0136] The method for producing 2-(chloromethyl)dibenzo[b,d]thiophene (Compound 58) was the same as that in Example 1, except that dibenzo[b,d]thiophene was used instead of UV-P (Compound 3).

[0137] Example 33 Preparation of the reaction mixture (59) of 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate (Eutec Co., Eusorb UV-120) and 5-(4-(methylamino)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (compound 21)

[0138] The procedure was repeated in the same manner as in Example 2, except that 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate (Eutec Co., Eusorb UV-120, melting point 149°C) was used instead of UV-P (compound 3). After washing with water and drying, the product was directly reacted and refluxed with (compound 21) in dichloromethane to obtain a mixture product (59).

[0139] Example 34 Preparation of 1-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)-5-(4-(dimethylamino)benzylidene)pyrimidine-2,4-,6(1H,3H,5H)trione (Compound 60) [ka]

[0140] Dissolve 15 g of 4-(dimethylamino)benzaldehyde, 13.2 g of dimethylmalonate, and 15 ml of pyridine in toluene and heat to reflux. Monitor the reaction by sampling, remove the solvent, and obtain dimethyl 2-(4-(dimethylamino)benzylidene)dimethylmalonate compound (compound 61) by chromatography. Its chemical formula is C 14 H 17 NO4, melting point is 86-88℃. [ka]

[0141] 26.3 g of dimethyl 2-(4-(dimethylamino)benzylidene)dimethylmalonate compound (compound 61) and 4.6 g of diaminomethane are refluxed in ethanol for 3 hours. The solvent is evaporated to dryness to obtain the ring-closed compound. 14.6 g of the ring-closed compound, 21 g of chromium trioxide, and 100 ml of water are mixed, and 45 ml of concentrated sulfuric acid is added dropwise. After the addition of concentrated sulfuric acid is completed, chromium trioxide (21 g / 50 ml water) is added dropwise, heated to reflux, and sampled to monitor the reaction. After cooling to room temperature, the reaction mixture is poured into an equal volume of water and cooled to 10°C in an ice bath. The precipitate is separated and washed with water. The precipitate is dispersed in 30 ml of water, and 50 ml of saturated sodium carbonate solution is added and stirred. Filter to obtain compound (60), whose chemical formula is C 27 H 24 N6O4, MS m / z = 496.2 [M] + It is.

[0142] Example 35 Preparation of 1-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)-5-(4-(dimethylamino)benzylidene)-3-methylimidazolidine-2,4-dione (Compound 62) [ka]

[0143] In the same manner as in Example 2, 27.5 g of compound (4) was reacted with 10 g of glycine methyl ester to obtain (3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)glycine methyl ester (compound 63). [ka]

[0144] 16.3 g of compound (63) and 5.1 g of 2-isocyanato-2-methylpropane are heated to reflux in dichloroethane overnight, distilled under reduced pressure to remove unreacted 2-isocyanato-2-methylpropane and dichloroethane, and then separated by chromatography to obtain 1-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)-3-(tert-butyl)imidazolidine-2,4-dione (compound 64). [ka]

[0145] In a manner similar to that of Example 4, 4 g of compound (65) was reacted with 1.5 g of 4-(dimethylamino)benzaldehyde to obtain 1-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)-3-(tert-butyl)imidazolidine-2,4-dione (compound 62), whose chemical formula is C 30 H 32 N6O3, m / z is 524.3[M] + It is. [ka]

[0146] Example 36 Preparation of 5-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzyl)-2-(4-(diethylamino)phenyl)-2-methyl-1,3-dioxane-4,6-dione (Compound 67) and 5-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzylidene)-2-(4-(diethylamino)phenyl)-2-methyl-1,3-dioxane-4,6-dione (Compound 90) [ka] [ka]

[0147] Dissolve 5.2 g of malonic acid (68) in 6 ml of acetic anhydride, add 0.15 ml of concentrated sulfuric acid while cooling with ice water and stirring, heat in a water bath to dissolve, add 4-(diethylamino)acetophenone (69) and stir at room temperature overnight. After washing with water, extract with ethyl acetate to obtain 2-(4-(diethylamino)phenyl)-2-methyl-1,3-dioxane-4,6-dione (compound 70). [ka]

[0148] 2.75 g of compound (4) was added to 2.34 g of compound (70), and the mixture was refluxed overnight in an ethanolic solution of sodium chloride. The solvent was removed, and the mixture was neutralized with HCl. The product was then separated by chromatography to give compound (67), whose chemical formula is C 29 H 30 N4O5, m / z is 514.2 [M] + It is. [ka]

[0149] The procedure is the same as in Example 3, except that compound (3) is used instead of compound (5), to obtain 3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzaldehyde (compound 89). The procedure is the same as in Example 4, except that compound (70) is used instead of barbituric acid and compound (89) is used instead of compound (6), to obtain 5-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methylbenzylidene)-2-(4-(diethylamino)phenyl)-2-methyl-1,3-dioxane-4,6-dione (compound 90), whose chemical formula is C 29 H 28 N4O5, m / z is 512.2[M] + It is. [ka]

[0150] Example 37 Preparation of 5-(9H-carbazol-3-yl)-3-(4-(dimethylamino)phenyl)oxazolidine-2,4-dione (Compound 71) [ka]

[0151] In an ice-water bath, 34g of 9H-carbazole is dissolved in 400ml of dry dichloromethane, and 30g of anhydrous AlCl3 is gradually added to the solution, which is stirred for 10 minutes. Then, 31g of 2-chloro-2-oxoacetate methyl (compound 72) is gradually added dropwise. After the addition is complete, the mixture is stirred at room temperature. After the reaction is complete, the reaction mixture is sampled and monitored, and the reaction mixture is poured into a hydrochloric acid-ice-water bath, extracted with dichloromethane, and dried to obtain 2-(9H-carbazol-3-yl)-2-oxoacetate methyl (compound 73). [ka]

[0152] Add 18 g of compound (73) to 150 mL of absolute ethanol and stir at room temperature. Add 2.6 g of sodium borohydride and stir the reaction mixture at room temperature for 50 minutes. After completion of the reaction, monitor by sampling and pour the reaction mixture into a hydrochloric acid-ice water bath. Extract with ethyl acetate and dry to obtain 2-(9H-carbazol-3-yl)-2-oxoacetate methyl ester (compound 74). [ka]

[0153] Dissolve 2.5 g of compound (74) in 20 ml of dichloromethane, add 1.5 ml of triethylamine and stir. Add 1.6 g of 4-isocyanato-N,N-dimethylaniline (75) in dichloromethane (10%) dropwise. After the addition is complete, reflux in dichloromethane and monitor the reaction. After the reaction is complete, neutralize with HCl. After washing with water and removing the solvent, separate by chromatography to obtain compound (71). Its chemical formula is C 23 H 19 N3O3, m / z is 385.1 [M] + ). [ka]

[0154] Example 38 Preparation of 5-((9H-carbazol-3-yl)chloromethyl)-3-(4-(dimethylamino)phenyl)oxazolidine-2,4-dione (Compound 76) and 5-((9H-carbazol-3-yl)methylene)-3-(4-(dimethylamino)phenyl)oxazolidine-2,4-dione (Compound 88) [ka] [ka]

[0155] The procedure of Example 3 was repeated except that 9H-carbazole was used instead of compound (5), to obtain 9H-carbazole-3-carbaldehyde (compound 77), which has a melting point of 158°C. [ka]

[0156] At 4°C, 5g of 9H-carbazole-3-carbaldehyde (compound 77) and 2.5ml of methyl 2,2-dichloroacetate in anhydrous ethyl ether (30ml) are added in portions under argon, stirred for 1 hour while maintaining the temperature low, and then heated to reflux. After sampling and monitoring, when the reaction is complete, water is added and the organic layer is separated. After drying, concentration, and separation by chromatography, 3-(9H-carbazol-3-yl)-3-chloro-2-oxopropionate (79) is obtained.

[0157] The procedure of Example 37 was repeated except that compound (79) was used instead of compound (73), to give 3-(9H-carbazol-3-yl)-3-chloro-2-hydroxypropionate (80). [ka]

[0158] The procedure of Example 37 was repeated, except that compound (80) was used instead of compound (74), to give 3-(9H-carbazol-3-yl)-3-chloro-2-hydroxypropionate (76), whose chemical formula is C 24 H 20 ClN3O3, m / z is 433.1 [M] + ). [ka]

[0159] 4.3 g of compound (76) is dissolved in pyridine and heated to 80°C. 1.5 ml of DBU (1,8-diazabicycloundec-7-ene) is added and reacted. After the reaction is complete (monitored by sampling), it is distilled under reduced pressure. Compound (88) is obtained by chromatographic separation. Its chemical formula is C 24 H 19 N3O3, m / z is 397.1[M] + ). [ka]

[0160] Example 39 Preparation of 2-(1-(9H-carbazol-3-yl)ethyl)-5-(4-(dimethylamino)benzylidene)-1,3-dioxane-4,6-dione (Compound 81) [ka]

[0161] In an ice-water bath, dissolve 34g of 9H-carbazole in dichloromethane, then slowly add 30g of anhydrous AlCl3 and continue stirring for 10 minutes, then slowly add 20ml of acetyl chloride. After the addition is complete, continue stirring at room temperature. After the reaction is complete, the reaction solution is gradually poured into a hydrochloric acid-ice-water bath, extracted with dichloromethane, concentrated, and separated by chromatography to obtain the main product 3-acetylcarbazole (82). Its melting point is 167°C. [ka]

[0162] 5.2 g of malonic acid, 15.3 g of acetic anhydride, and 0.2 ml of concentrated sulfuric acid are heated in a water bath. The mixture is cooled to room temperature, and 8.4 g of 3-acetylcarbazole (82) is added dropwise. The mixture is reacted for 1 hour, and then left in a refrigerator overnight. After washing with water, the mixture is extracted with ethyl acetate and separated by chromatography to obtain 2-(1-(9H-carbazol-3-yl)ethyl)-1,3-dioxane-4,6-dione (83). [ka]

[0163] Compound (81) is obtained by the same procedure as in Example 35, except that compound (83) is used instead of compound (65). The chemical formula of compound (81) is C 27 H 24 N2O4, m / z is 440.2 [M] + It is. [ka]

[0164] Example 40 Preparation of 5-(((4-(dimethylamino)phenyl)imino)methyl)quinolin-7-yl-3-(3-(2H-benzo[d][1,2,3]triazol-2-yl)tert-butyl)-4-hydroxyphenyl)propionate (Compound 84) [ka]

[0165] 3-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-5-(tert-butyl)-4-hydroxyphenyl)propionate (Eutec co., BZTME, compound 85) is hydrolyzed with KOH / MeOH, then acid is added to neutralize. Extraction with dichloromethane gives 3-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-5-(tert-butyl)-4-hydroxyphenyl)malonic acid (86). After thorough drying, excess thionyl chloride is added and reacted by heating under reflux. After the reaction is completed (check by sampling), the unreacted thionyl chloride is removed to give the compound 3-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-5-(tert-butyl)-4-hydroxyphenyl)propionyl chloride, which is ready for use.

[0166] [ka] Weigh out 1.75g ​​of 8-hydroxyquinoline-5-carbaldehyde (NSC 122131, compound 87), dissolve it in 20ml of dichloromethane, add 2g of triethylamine and stir. Drop in 3.6g of the 3-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-5-(tert-butyl)-4-hydroxyphenyl)propionyl chloride compound (86) in dichloromethane solution (20ml). Stir overnight at room temperature. Pour the product into ice water, extract with dichloromethane, then wash with 1% dilute hydrochloric acid and brine. After drying, obtain compound 5-formylquinolin-8-yl-3-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-5-(tert-butyl)-4-hydroxyphenyl)propionate (91).

[0167] Weigh out 5 g of compound (91) and 1.4 g of p-(dimethylamino)aniline, dissolve them in 40 ml of absolute ethanol, remove water, and heat under reflux for 4 hours. Sampling is performed to monitor the reaction, and after completion of the reaction, the solvent is removed to obtain compound (84). Its chemical formula is C 37 H 36 N6O3, m / z is 612.3[M] + It is. [ka]

[0168] Example 41 Use in improving the performance of optical recording media As shown in the diagram below, compound (18) can be obtained by covalently bonding compound (B). [ka]

[0169] The melting point of compound (B) was 175°C, but by covalently bonding with a benzotriazole-based compound, the melting point increased to 224°C (compound 18). As a result, compound (18) is less likely to decompose even when an optical disk is irradiated with laser light, generating high local temperatures of 250°C or more, and this represents an important improvement for organic dyes (B) used in optical recording media.

[0170] Figure 3 shows the ultraviolet light absorption range of compound (18), covering UVA, UVB and blue light. It has been shown that the dye of compound (18) can protect optical disks from a wide range of ultraviolet light (UVA+UVB). Therefore, in terms of optical disk storage, compound (18) is more advantageous than compound (B).

[0171] [Table 3]

[0172] Example 42 Advantages when used as UV or blue light absorbers When the compound of the present invention is used as an ultraviolet light and / or blue light absorber, it has the function of absorbing ultraviolet light (UVA+UVB) and blue light. In comparison with the commercially available blue light blocker Eusorb UV-1990 (Eutec Co.) (Table 4), the commercially available Eusorb UV-1990 has very weak absorption of UVB (wavelength 280 nm). The compound of the embodiment of the present invention is superior to the currently available blue light blocker Eusorb UV-1990 in both coverage and absorbance to ultraviolet light.

[0173] [Table 4]

[0174] Example 43 Stability and weather resistance when used as a light conversion agent The thermal stability of the compounds of the examples is measured by a thermal analyzer (TGA). The greater the weight loss, the lower the stability. Figure 2 shows the results of the TGA, which shows that when heated to 220°C, compound (7) of Example 4 loses less than 1% weight, and when heated to a high temperature of 312°C, the weight loss is only about 5%. In other words, compound (7) has very high thermal stability.

[0175] Figure 4 is a photograph of the PE agricultural film made from compound (7) of Example 4 of the present invention under fluorescent light (the agricultural film is placed on a gray opaque background to show the color). The agricultural film is transparent and has an orange-red color.

[0176] Table 5 shows a comparison of the weather resistance of agricultural films before and after the compound improvement. When used in outdoor agricultural films, the RL1000 product (BASF) was stable for only two seasons, whereas the compound (7) of the present invention was stable for more than three seasons. [ka]

[0177] [Table 5]

[0178] The present invention has been disclosed above through preferred embodiments, but they do not limit the present invention, and any technical solutions obtained by using equivalent substitution or equivalent transformation are included in the protection scope of the present invention.

[0179] (Additional Note) (Appendix 1) Formula (1) or formula (2), [ka] [ka] It has a structural formula represented by at least one visible or fluorescent light emitting group and at least one other ultraviolet light absorbing group, wherein [ka] or [ka] is a group that emits visible light or fluorescence, [ka] is an ultraviolet light absorbing group, R1 to R3 are single bonds or / and any divalent linking group, A, B, and C are an unsubstituted or R4-substituted benzene ring, benzocarbocycle, 5- to 7-membered nitrogen-containing heterocycle, or 5- to 7-membered nitrogen-containing benzoheterocycle, D is an unsubstituted or substituted 5- to 7-membered heterocycle or 5- to 7-membered benzoheterocycle consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms, and the substituents of the carbon atoms of the ring are one or more hydrogen atoms, hydrogen atoms, a hydroxy group, an oxygen group, a thio group, a thiol group, an amine group, an imine group, a linear or branched C1-C8 alkyl or alkenyl group, and R4; the substituents of the nitrogen atoms of the ring are selected from one or more hydrogen atoms, a hydroxy group, an oxygen group, a linear or branched C1-C8 alkyl group, and R4 is one or more substituents, and when there are more than one, R4 is each independently hydrogen, halogen, a hydroxy group, an amino group, a nitro group, a cyano group, a linear or branched C1-C 18 Alkyl, alkenyl or alkoxy groups, unsubstituted or substituted phenyl groups, SR5, SO2R5, SO3R 5、 A novel polycyclic compound characterized in that R5, R6, and R7 are each independently selected from hydrogen, a straight-chain or branched C1-C8 alkyl group, and R4 and its adjacent R4, or R4 and its adjacent ring are both represented as a fused carbocycle or fused heterocycle of 3-6 atoms.

[0180] (Appendix 2) D is [ka] Selected from In the formula, n=0 to 1, and X1 to X6 each independently represent C=O, C=S, C=N-R8, N, NR9, C, O, S, or CR 10 , C.R. 11 R 12 , CNR 11 R 12 , and C.R. 10 NR 11 R 12 Selected from R8 to R 12 are each independently selected from hydrogen, a linear or branched C1-C8 alkyl group or alkenyl group, and a phenyl group that is unsubstituted or substituted with one or more linear or branched C1-C6 alkyl groups or halogens; R4 is a substituent and each independently selected from hydrogen, halogen, a nitro group, a cyano group, a linear or branched C1-C8 alkyl group, an alkenyl group, or an alkoxy group, SR5, SO2R5, COOR5, COR5, C(O)NR6R7, and NR6R7; R5, R6, and R7 are each independently hydrogen, a linear or branched C1-C8 alkyl group, and p=0 to 3.

[0181] (Appendix 3) D is [ka] Selected from In the formula, n=0 to 1, and X1 to X6 each independently represent C=O, C=S, C=N-R8, N, NR9, C, O, S, or CR 10 , and C.R. 11 R 12 Selected from R9 to R 12are each independently selected from hydrogen, a linear or branched C1-C6 alkyl group, or an alkenyl group; R4 is a substituent, each independently selected from hydrogen, a halogen, a nitro group, a cyano group, a linear or branched C1-C8 alkyl group, an alkenyl group, or an alkoxy group, SR5, SO2R5, COOR5, COR5, C(O)NR6R7, and NR6R7; and R5, R6, and R7 are each independently selected from hydrogen, a linear or branched C1-C6 alkyl group, and p=0 to 2.

[0182] (Appendix 4) R1 to R3 are a single bond or -O-, -S-, -C(=O)-, -COO-, -C(=S)-, -C(=NR 13 )-, -N(R 13 )-, -C(R 14 )(R 15 )-, -C(R 16 )=, -C≡, -C(R 17 )=C(R 18 )-, -Ph-, and -Ph-, where R 13 ~R 18 are each independently selected from hydrogen, halogen, a hydroxyl group, a linear or branched C1-C6 alkyl or alkenyl group which is unsubstituted or substituted with a halogen, and a phenyl group which is unsubstituted or substituted with one or two halogens or a linear or branched C1-C6 alkyl group, and Ph is a phenyl group which is unsubstituted or substituted with one or more halogens, hydroxyl groups, C1-C6 alkoxy groups, or linear or branched C1-C6 alkyl groups.

[0183] (Appendix 5) A is, [ka] Selected from B is, [ka] Selected from C is [ka] Selected from In the formula, R 19 ~R 20 are each independently selected from hydrogen, a linear or branched C1-C6 alkyl group, or a phenyl group that is unsubstituted or substituted with one or more halogens or a linear or branched C1-C6 alkyl group, and Ph is a phenyl group that is unsubstituted or substituted with one or more halogens, a hydroxy group, a C1-C6 alkoxy group, or a linear or branched C1-C6 alkyl group.

[0184] (Appendix 6) A is, [ka] Selected from B is, [ka] Selected from C is [ka] Selected from D is [ka] Selected from In the formula, when n=0, X1 is selected from C=O and C=S, and X2 and X 3、 X4 is independently C=O, C=S, C=N-R8, N, NR9, C, O, S, or CR 10 , C.R. 11 R 12 , and CNR 11 R 12 Selected from When n=1, X4 and X6 are each independently selected from C=O and C=S, and X1, X2, and X3 are each independently selected from C=O, C=S, C=N-R8, N, NR9, C, O, S, CR 10 , and C.R.11 R 12 R1 to R3 are single bonds, or / and -O-, -C(=O)-, -COO-, -N(R 13 )-, -C(R 14 )(R 15 )-, -C(R 16 )=, and -C(R 17 )=C(R 18 )-, R4 is a substituent, and each R4 is independently selected from hydrogen, halogen, a nitro group, a cyano group, a linear or branched C1 to C8 alkyl group, an alkenyl group, or an alkoxy group, COOR5, COR5, and NR6R7; p=0 to 2; R5 to R7 are each independently selected from hydrogen and linear or branched C1 to C6 alkyl groups; R8~R 12 are each independently selected from hydrogen, a linear or branched C1-C6 alkyl group, and a phenyl group that is unsubstituted or substituted with one or two halogens or C1-C6 alkyl groups; R 13 ~R 18 are each independently selected from hydrogen, halogen, a linear or branched C1-C6 alkyl group, and a phenyl group that is unsubstituted or substituted with one or two halogens or C1-C6 alkyl groups; R 19 is selected from hydrogen, a linear or branched C1-C6 alkyl group, and a phenyl group that is unsubstituted or substituted with one or two halogens or C1-C6 alkyl groups; The compound according to appendix 5, wherein Ph is a phenyl group that is unsubstituted or substituted with one or two halogens, a hydroxyl group, a C1-C6 alkoxy group, or a linear or branched C1-C6 alkyl group.

[0185] (Appendix 7) R2 is a single bond or -(CHR 21 ) q N(R 22 )- and R 21 , R 22are each independently selected from hydrogen and a linear or branched C1-C6 alkyl group, and q=0 to 6; D is the following ring: [ka] [ka] Selected from R4 is a substituent, and each independently is selected from hydrogen, halogen, a linear or branched C1-C8 alkyl group or alkoxy group, COOR5, COR5, and NR6R7, where R5, R6, and R7 are each independently selected from hydrogen, a linear or branched C1-C6 alkyl group, p=0-2, R9, R 23 ~R 34 is selected from hydrogen, a linear or branched C1-C6 alkyl group, and a phenyl group that is unsubstituted or substituted with one or two linear or branched C1-C6 alkyl groups.

[0186] (Appendix 8) [ka] is the following group: [ka] Selected from R4 is independently selected from hydrogen, halogen, a linear or branched C1-C8 alkyl group, an alkenyl group or an alkoxy group, SR5, SO2R5, COOR5, COR5, C(O)NR6R7, and NR6R7, where R5, R6, and R7 are independently selected from hydrogen, a linear or branched C1-C6 alkyl group, p=0-2, and R 19 , R 35 ~R 39are each independently selected from hydrogen, a linear or branched C1-C6 alkyl group, and a phenyl group which is unsubstituted or substituted with one or two halogens or a C1-C6 alkyl group, and Ph is a phenyl group which is unsubstituted or substituted with one or two halogens, an OH group, a C1-C6 alkoxy group, or a linear or branched C1-C6 alkyl group.

[0187] (Appendix 9) [ka] teeth, [ka] Selected from [ka] teeth, [ka] Selected from D is [ka] [ka] Selected from [ka] teeth, [ka] [ka] Selected from The visible light emitting group or ultraviolet light absorbing group is substituted with an (R4)p substituent, where p=0 to 3, and R4 is a substituent and each independently represents hydrogen, halogen, a hydroxyl group, an amino group, a nitro group, a cyano group, a linear or branched C1 to C 18selected from an alkyl group, an alkenyl group, or an alkoxy group, an unsubstituted or one or more linear or branched C1-C6 alkyl group, or a phenyl group substituted with halogen, SR5, SO2R5, SO3R5, COOR5, COR5, OCOR5, C(O)NR6R7, SO2NR6R7, and NR6R7, and R5, R6, and R7 are each independently selected from hydrogen, a linear or branched C1-C8 alkyl group, R4 and its adjacent R4, or R4 and its adjacent ring can both represent a fused carbocyclic or fused heterocyclic ring of 3-6 atoms, R 40 ~R 49 are the same or different and are each independently selected from hydrogen, a linear or branched C1-C8 alkyl or alkenyl group, and an unsubstituted or linear or branched C1-C6 alkyl group or a phenyl group substituted with halogen; R 50 is selected from hydrogen, a monovalent metal, a linear or branched C1-C8 alkyl or alkenyl group, and a phenyl group that is unsubstituted or substituted with one or more linear or branched C1-C6 alkyl groups or halogens.

[0188] (Appendix 10) The following structural formula: [ka] [ka] [ka] The compound according to any one of claims 1 to 9, characterized in that it is represented by the following formula:

[0189] (Appendix 11) The following reaction steps: [ka] [ka] [ka] [ka] [ka] Including any of the following: In the formula, rings A to D and R1 to R3 are as defined in Appendix 1. D' is a precursor of the D ring, [ka] Selected from D" is a precursor of the D ring and has the formula [ka] and Z is a leaving group, which includes a halogen or a C1-C6 alkoxy group; T are the same or different and are each independently selected from NH, NH2, OH, and SH; U and V are C=O, C=S, and C=NR 51 , C(R 52 )(R 53 ) are selected, R 50 ~R 53 and are the same or different and each independently selected from a single bond, hydrogen, and a linear or branched C1-C6 alkyl group.

[0190] (Appendix 12) A film for use as a light conversion agent, dye, pigment, fluorescent agent, ultraviolet light and / or blue light absorbent, characterized by containing a compound of formula (1) or formula (2) described in any one of appendixes 1 to 10.

Claims

1. Formula (1), 【Chemistry 1】 It has a structural formula represented by 【Chemistry 2】 is the following group: 【Chemistry 3】 and R 2 is —(CHR 21 ) q N(R 22 )—; R 21 and R 22 are each independently selected from hydrogen and a linear C 1 -C 8 alkyl group; q is 0 to 2; R 4 is selected from hydrogen, halogen, a hydroxyl group, a linear or branched C 1 -C 8 alkyl group, a C 1 -C 4 alkoxy group, and COOR 5 , where p=0-2; C is selected from a benzene ring, a 5-7 membered nitrogen-containing benzoheterocycle, R 3 is —C(R 16 )═; R 16 is selected from hydrogen, linear or branched C 1 -C 6 alkyl groups, and phenyl groups unsubstituted or substituted with C 1 -C 4 alkyl groups; D is the following ring: 【Chemistry 4】 Selected from A novel polycyclic compound, characterized in that R 9 , R 25 and R 26 are selected from hydrogen and linear or branched C 1 -C 6 alkyl groups.

2. The compound of formula (1) is 【Chemistry 5】 The compound according to claim 1, characterized in that it is represented by:

3. 3. An agricultural film comprising the compound according to claim 1 or 2 as a light conversion agent, dye, pigment, fluorescent agent, ultraviolet light or / and blue light absorbent.

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