TW201546034A - Asymmetric dioxime ester and corresponding intermediate, manufacturing method and applications - Google Patents

Abstract

The invention relates to asymmetric dioxime ester, its corresponding intermediate and manufacturing method. The asymmetric dioxime ester includes structural formula (I). The structural formula (I) has molecular groups Ar1, X1, Ar2, Y1, R1, R2, R3, R11-R16 and R20. Wherein, Ar1 is di-o-arylene being substituted by X1 or di-o-hetero arylene being substituted by X1. Ar2 is arylene or hetero arylene. n is either 0 or 1. X1 is selected from the group consisting of NR18, O, S, C-O, and S-O. Y1 is selected from the group consisting of (CH2)mCR15R16, NR19, O(CR15R16)m, S(CR15R16)m, (CR15R16)m, C=O, and S=O. m is either 0 or 1. Each of R1, R2, R3, R11-R16 and R20 is respectively selected from the group consisting of hydrogen, alkyl, alkoxy, acyl, alkyl substituted by any groups, alkoxy substituted by any groups, cycloalkyl, and aryl substituted by any groups. The invention also relates to photocurable compositions which using the asymmetric dioxime ester as photoinitiators and the photocurable compositions manufacturing method, color filter and the color filter manufacturing method.

Description

Asymmetric diterpene ester compound and intermediate thereof and manufacturing method and application thereof

The present invention relates to an asymmetric diterpene ester compound characterized by an esterified derivative of an arylene group and a cyclic ketoxime in a molecule, and an esterified fluorenyl group at the α-position of the carbonyl group, which has Use as a photoinitiator in photocurable compositions.

The oxime ester compound has been discovered as a photoinitiator. The oxime ester compound is disclosed as a photoinitiator in both of the patents of US Pat. No. 3,558,309 and US Pat. No. 4,255,513. However, some structures of oxime esters have poor thermal stability or low brightness. It is difficult to meet the requirements of the modern electronic industry in terms of thermal stability, brightness, and the like. Chinese patent CN1514845A discloses a series of oxime ester compounds, and two varieties of OXE01 and OXE02 are marketed, and similar products include oxime esters 305 and 304 disclosed in Chinese patents CN101565472B and CN101508744B.

The substituted oxazolooxacyclohexanone ester described in Chinese patent CN102046667B has an absorption wavelength of up to 405 nm, which is advantageous for curing with LED lamps and visible light curing, but reduces the activity per unit weight due to the increase of molecular weight; The various diterpene ester derivatives of phenyl carbazole as disclosed in WO2008138732 have two oxime ester groups in one molecule, wherein one oxime ester is in the phenyl position of the N-substituted position, and experiments have proved that The oxime ester activity is very low, and it cannot give an additional contribution to the photoinitiating activity of the molecule, and is not practical.

In addition, there are many other patents for oxime ester photoinitiators, such as: WO2006018973, WO2007071497, CN1805955B, CN1922142B, CN1928715A, CN101508744B, CN102020727, but they are all side chains at the 3, 6, and 9 positions of carbazole. Various modifications were made, and some molecular weights increased without any improvement in photosensitivity.

The present invention provides an asymmetric diterpene ester compound having very excellent photoinitiating activity, comprising the following compound of the formula I:

Wherein Ar _{1 is} selected from a C ₆ -C ₂₀ o-arylene or C ₃ -C ₂₀ o-heteroaryl group substituted by X ₁ , a C ₆ -C ₂₀ o-arylene group or a C ₃ -C ₂₀ sub- The heteroaryl group is bonded to Y ₁ and a carbonyl group by two adjacent atoms to form a ring structure, and the substituents on the remaining atoms are each selected from the group consisting of a hydrogen atom, a halogen atom, and a C ₁ -C ₁₂ alkyl group. , C ₅ -C ₇ cycloalkyl, C ₅ -C ₇ cycloalkyl substituted C ₁ -C ₄ alkyl, C _1- C ₁₂ alkoxy, C ₁ -C ₄ alkylbenzyl group, C _1- C ₃ alkylenedioxy, R ₂ C(O)O, C ₁ -C ₁₂ alkylthio, C ₁ -C ₄ alkylphenylthio, CN, carboxyl, C ₁ -C ₁₂ alkane Oxycarbonyl, arylcarbonyl, heteroarylcarbonyl, X ₃ R ₁₈ , C ₁ -C ₄ alkylphenoxy, C1-C8 alkyl acyl phenoxy, C ₅ -C ₆ cycloalkyl acyl oxy a C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy group, an aryl acyl phenoxy group, a heteroaryl acyl phenoxy group, a R ₂ C(O)O substituted C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylphenylthio, C ₁ -C ₈ alkyl phenyl phenylthio, C ₅ -C ₆ cycloalkyl acyl phenylthio, C ₅ -C ₆ ring Alkyl-substituted C ₁ -C ₄ alkyl acyl phenylthio, aryl Acyl phenylthio, phenylthio heteroaryl group; substituted with one or more C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ alkylbenzyl group, R ₂ C (O) O a C ₁ -C ₄ alkoxy; phenyl and optionally by one or more C ₁ -C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl acyl, aryl acyl, heteroaryl acyl, X ₃ R ₁₇ , benzene a halogen atom, a CN-substituted phenyl group; and a glycidyl group, wherein the epoxy group is arbitrarily condensed with a C ₁ -C ₄ alkyl aldehyde or a ketone; X _{3 is} selected from O, S or NR ₂₂ ; Ar _{2 is} selected from: the X ₁ and Ar ₁ C ₆ -C ₂₀ connected arylene group, or by X ₁ and Ar C ₁ is connected to ₃ -C ₂₀ heteroarylene group; or X ₁ and Ar ₁ are connected through the The Ar ₂ carbon atom ortho to X _{1 is} bonded to a straight bond, a carbon atom, a carbonyl group, O, S, NR ₁₈ and Ar ₁ to form a cyclic structure; n is 0 or 1; X _{1 is} selected from the group consisting of: O, S , NR ₁₈ or Y ₂ -Z ₁ -Y ₂ ; Y _{1 is} selected from: (CH ₂ ) _m CR ₁₅ R ₁₆ , NR ₁₉ , O(CR ₁₅ R ₁₆ ) _m , S(CR ₁₅ R ₁₆ ) _m , ( CR ₁₅ R ₁₆ ) _m C=O or S=O, m is 0 or 1; Z _{1 is} selected from: C ₁ -C ₁₀ linear alkylene group, C ₁ -C ₁₀ branched alkylene group, by one or a C ₁ -C ₁₀ with multiple oxygen or sulfur atoms attached to the terminal group a linear alkylene group, a C ₁ -C ₁₀ branched alkylene group bonded to a terminal group by one or more oxygen atoms or a sulfur atom, and a C ₂ -C ₁₀ inserted by one or more oxygen atoms or sulfur atoms a linear alkylene group, a C ₂ -C ₁₀ branched alkylene group inserted by one or more oxygen atoms or sulfur atoms, an unsubstituted C ₆ -C ₂₀ arylene group, or a substituted C ₆ -C ₂₀ arylene; Y _{2 is} selected from: O, S, NR ₁₈ or OC(O); R _{1 is} selected from the group consisting of: a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a diphenylphosphonyl group, and a di(C ₁ -C ₄ alkoxy)phosphono group; or any C ₂ -C ₁₈ alkyl group substituted by one or more C ₃ -C ₇ cycloalkyl groups, phenyl group, OR ₂₀ , SR ₂₁ , NR ₂₂ R ₂₃ , Wherein the phenyl group of the C ₂ -C ₁₈ alkyl group is any one or more of a halogen atom, a C ₁ -C ₄ alkyl group, a C ₅ -C ₇ cycloalkyl group, a heterocycloalkyl group, a phenyl group, a heteroaryl group, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted; or C ₂ -C ₁₈ alkyl inserted by C ₃ -C ₇ cycloalkylene, phenylene, O, S, NR ₂₂ C ₃ -C ₈ cycloalkyl, CN, NO ₂ , phenyl; or by any one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, Phenyl, a heteroaryl group, a CN, a C ₁ -C ₄ alkanoyloxy group, an aroyloxy group-substituted phenyl group; or a C ₁ -C ₁₂ alkyl acyl group, a C ₁ -C ₁₂ alkoxycarbonyl group, wherein the alkyl group is optionally One or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₃ R ₂₀ substituted; or C ₁ -C ₁₂ alkyl acyl a C ₁ -C ₁₂ alkoxycarbonyl group, wherein the alkyl group is optionally interrupted by one or more phenylene groups, X ₃ ; or a phenyl group unsubstituted benzoyl group, phenoxycarbonyl group; or a phenyl group is optionally a benzoyl group or a phenoxycarbonyl group substituted with one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₂ R ₂₀ ; R ₂ and R ₃ are each independently selected from the group consisting of: a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₁ -C ₁₈ alkoxy group, a C ₂ -C ₁₈ alkenyl group, a phenyl group, a naphthyl group, a C ₅ -C ₇ group. One of cycloalkyl groups; or optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy, substituted C ₂ -C ₁₈ alkenyl; or C ₅ -C ₇ cycloalkylene, phenylene, O, S, NR ₁₇ the inserted C ₂ -C ₁₈ alkenyl; or optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN a C ₂ -C ₁₈ alkenyl group substituted by a C ₁ -C ₄ alkanoyloxy group or an aroyloxy group and inserted by a C ₅ -C ₇ cycloalkylene group, a phenylene group, O, S, NR ₁₇ ; Or a C ₅ -C ₇ cycloalkyl group optionally substituted by one or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom or a CN; or a benzoyl group or a phenoxycarbonyl group which is not substituted with a phenyl group; Or a benzoyl group, a phenoxycarbonyl group in which a phenyl group is substituted by any one or more halogen atoms R ₁₇ , C ₅ cycloalkyl, C ₆ cycloalkyl, CN, OH, XR ₁₇ ; phenyl or naphthyl; Any phenyl group substituted by one or more C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy groups, phenyl groups, halogen atoms, CN; or optionally by one or more C ₁ -C ₄ alkyl groups a C ₁ -C ₄ alkoxy group, a phenyl group, a halogen atom, a CN-substituted naphthyl group; and R ₁₅ and R ₁₆ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group; , carboxy-substituted C ₁ -C ₅ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) One of C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl substituted by O; or optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ a cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, a C ₂ -C ₁₈ alkyl group substituted with an aroyloxy group; or C ₅ -C ₇ a C ₂ -C ₁₈ alkyl group in which a cycloalkylene group, a phenylene group, an O, S, or NR ₁₇ is inserted; or optionally substituted by one or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, or a CN C ₅ -C ₇ cycloalkyl; or optionally by one or more C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxy, C ₁ -C ₁₂ alkyl acyl, C ₅ -C ₆ Cycloalkyl formyl, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl acyl group, benzoyl group, XR ₁₇ , phenyl group, halogen atom, phenyl substituted by CN; or R ₁₅ , R ₁₆ together with the carbon atom to which it is attached, constitutes a ring and the number of atoms in the ring is 4-7; or R ₁₅ and R ₁₆ together with adjacent substituents form a ring and the number of atoms in the ring is 4-7 ; R ₁₇ is C ₁ -C ₄ alkyl; R ₁₈ and R ₁₉ are each independently selected from the group consisting of hydrogen atom, C ₁ -C ₁₈ alkyl group, C ₁ -C ₄ alkane; a C ₁ -C ₅ alkyl group substituted with an oxyacyl group, a C ₁ -C ₄ alkyl group substituted by R ₂ C(O)O, one of C ₅ -C ₇ cycloalkyl groups, or a phenyl group; or any One or more halogen atoms, C ₁ -C ₄ alkyl, C ₃ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyl a C ₁ -C ₁₈ alkyl group substituted by an oxy group; or any C ₂ -C ₁₈ alkyl group inserted by one or more C ₃ -C ₇ cycloalkylene groups, phenylene groups, O, S, NR ₁₇ Or any C ₅ -C ₇ cycloalkyl group substituted by one or more C ₁ -C ₄ alkyl, phenyl, halogen atom, CN; or optionally by one or more C ₁ -C ₄ alkyl groups, Carboxyl group, C ₁ -C ₁₂ alkyl acyl group, C ₅ -C ₆ cycloalkyl formyl group, C ₂ -C ₄ alkyl acyl group substituted by C ₅ -C ₆ cycloalkyl group, aryl acyl group, XR ₁₇ , benzene a phenyl group substituted with a halogen atom or a CN; or R ₁₈ is bonded to an aromatic ring in one of Ar ₁ or Ar ₂ by a straight bond, a carbon atom, a carbonyl group, or a new ring; or R ₁₉ is bonded through a bond, carbon atom, _a carbonyl group attached to the aromatic ring constituting Ar new _{ring; R 20, R 21, R} 22, R 23 are each independently represented by a group selected from the group consisting of the following : One of a hydrogen atom, C ₁ -C ₁₈ alkyl, C ₃ -C ₇ cycloalkyl, wherein; or by halogen, CN, C ₁ -C ₄ alkoxy substituted C ₁ -C ₁₈ alkyl; or a C ₂ -C ₁₈ alkyl group inserted by one or more oxygen atoms, a C ₅ -C ₇ cycloalkylene group, a phenylene group; or a C ₁ substituted by a phenyl group, a C ₃ -C ₇ cycloalkyl group -C ₃ alkyl; or phenyl, naphthyl unsubstituted phenyl, naphthyl, benzoyl; or optionally halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio, NR ₂₄ R ₂₅ , C ₁ -C ₁₂ alkyl acyl, phenyl substituted by benzoyl, naphthyl, benzoyl; R ₂₄ , R _{25 is} each C ₁ -C ₄ alkyl, or NR ₂₄ R ₂₅ together is morpholine, acridine, pyridazine, N-methylpyridazine, pyrrole.

Furthermore, the present invention further provides a process for producing an asymmetric dioxime ester compound of the formula I, which comprises the following steps: (1) Step 1: The ortho-methylene group of the cyclopentanone carbonyl group in the following compound of the formula IV is The selective deuteration is carried out by deuteration of a compound of the formula IV and an alkyl nitrite in an acidic solution to obtain a corresponding intermediate as a ketoxime compound, such as the following compound of the formula V. ; (2) Step 2: The second structural deuteration is continued with the compound of the formula V, and the second deuteration method is one of the following two methods: Method A: the compound of the formula V and the alkyl nitrite in an acidic solution The deuteration reaction occurs to obtain the corresponding second deuterated intermediate structure of the compound of formula VI; Method B: the deuteration reaction of the carbonyl group in the side chain R ₁ CH ₂ CO occurs in the hydroxylamine solution of the compound of formula V. Corresponding second deuterated intermediate structure of the compound of formula VII; (3) Step 3: One of the above second deuterated intermediates VI or VII compounds and the following acylating reagents: Or an esterification reaction of its equivalent acylating reagent to give a corresponding structural formula I compound.

The invention further proposes an asymmetric diketone compound, as shown in the structural formula IV:

Wherein Ar _{1 is} selected from a C ₆ -C ₂₀ o-arylene or C ₃ -C ₂₀ o-heteroaryl group substituted by X ₁ , a C ₆ -C ₂₀ o-arylene group or a C ₃ -C ₂₀ sub- The heteroaryl group is bonded to Y ₁ and a carbonyl group by two adjacent atoms to form a ring structure, and the substituents on the remaining atoms are each selected from the group consisting of a hydrogen atom, a halogen atom, and a C ₁ -C ₁₂ alkyl group. , C ₅ -C ₇ cycloalkyl, C ₅ -C ₇ cycloalkyl substituted C ₁ -C ₄ alkyl, C _1- C ₁₂ alkoxy, C ₁ -C ₄ alkylbenzyl group, C ₁ -C ₃ alkylenedioxy, R ₂ C(O)O, C ₁ -C ₁₂ alkylthio, C ₁ -C ₄ alkylphenylthio, CN, carboxyl, C ₁ -C ₁₂ alkane Oxycarbonyl, arylcarbonyl, heteroarylcarbonyl, X ₃ R ₁₈ , C ₁ -C ₄ alkylphenoxy, C1-C8 alkyl acyl phenoxy, C ₅ -C ₆ cycloalkyl acyl oxy a C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy group, an aryl acyl phenoxy group, a heteroaryl acyl phenoxy group, a R ₂ C(O)O substituted C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylphenylthio, C ₁ -C ₈ alkyl phenyl phenylthio, C ₅ -C ₆ cycloalkyl acyl phenylthio, C ₅ -C ₆ ring alkyl substituted C ₁ -C ₄ alkyl phenylthio group, Acyl phenylthio, phenylthio heteroaryl group; or one or more C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ alkylbenzyl group, R ₂ C (O) O-substituted C ₁ -C ₄ alkoxy; or phenyl, or optionally substituted by one or more C ₁ -C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl acyl, aryl acyl, heteroaryl acyl, X ₃ R ₁₇ , phenyl, halogen atom, CN substituted phenyl; or epoxypropyl group, wherein the epoxy group is arbitrarily condensed with a C ₁ -C ₄ alkyl aldehyde, a ketone; X _{3 is} selected from O, S or NR _22; Ar ₂ is selected from: X ₁ through C Ar ₁ and connected ₆ -C ₂₀ arylene group, and X ₁ through Ar ₁ C ₃ -C ₂₀ connected heteroarylene group; or X ₁ and Ar by _{When the 1} phase is bonded, the Ar ₂ carbon atom ortho to X _{1 is} bonded to a straight bond, a carbon atom, a carbonyl group, O, S, NR ₁₈ and Ar ₁ to form a cyclic structure; X ₁ is selected from the group consisting of the following: :O, S, NR ₁₈ or Y ₂ -Z ₁ -Y ₂ ; Y1 is selected from the group consisting of: (CH ₂ ) _m CR ₁₅ R ₁₆ , NR ₁₉ , O(CR ₁₅ R ₁₆ ) _m , S _{(CR 15 R 16) m,} (CR 15 R 16) m C = O and S = O, m is 0 or _1; Z 1 is selected from the group consisting of the following: C ₁ -C ₁₀ linear alkylene , C ₁ -C ₁₀ a branched alkylene group, a C ₁ -C ₁₀ linear alkylene group bonded to a terminal group by one or more oxygen atoms or sulfur atoms, and C ₁ - bonded to the terminal group by one or more oxygen atoms or sulfur atoms _; C ₁₀ branched alkylene group, C ₂ -C ₁₀ linear alkylene group inserted by one or more oxygen atoms or sulfur atoms, C ₂ -C ₁₀ inserted by one or more oxygen atoms or sulfur atoms a branched alkylene group, an unsubstituted C ₆ -C ₂₀ arylene group, and a substituted C ₆ -C ₂₀ arylene group; Y ₂ is selected from the group consisting of O, S, NR ₁₈ And OC(O); R ₁ is selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a diphenylphosphonyl group, a di(C ₁ -C ₄ alkoxy)phosphonyl group; or any a C ₂ -C ₁₈ alkyl group substituted by one or more C ₃ -C ₇ cycloalkyl, phenyl, OR ₂₀ , SR ₂₁ , NR ₂₂ R ₂₃ wherein the C ₂ -C ₁₈ alkyl phenyl group Any one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, substituted aroyloxy; or C ₃ -C ₇ inserted cycloalkylene, _{phenylene, O, S, NR 22 C} 2 -C 18 alkyl; C ₃ -C ₈ Alkyl, CN, NO _2, phenyl; or any one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN a C ₁ -C ₄ alkanoyloxy group, an aroyloxy substituted phenyl group; or a C ₁ -C ₁₂ alkyl acyl group, a C ₁ -C ₁₂ alkoxycarbonyl group, wherein the alkyl group is optionally substituted by one or more halogens Atom, C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₃ R ₂₀ substituted; or C ₁ -C ₁₂ alkyl acyl, C ₁ -C _{a 12} alkoxycarbonyl group, wherein the alkyl group is optionally interrupted by one or more phenylene groups, X ₃ ; or a phenyl group unsubstituted benzoyl group, phenoxycarbonyl group; or a phenyl group by any one or more halogens Atom, C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₂ R ₂₀ substituted benzoyl, phenoxycarbonyl; R ₁₅ , R ₁₆ are each independently selected from the group consisting of the following: a hydrogen atom, C ₁ -C ₁₈ alkyl, carboxy substituted C ₁ -C ₅ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ - One of C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, or phenyl substituted by C ₅ alkyl, R ₂ C(O)O; It is intended to be one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, a C ₂ -C ₁₈ alkyl group substituted with an aroyloxy group; or a C ₂ -C ₁₈ alkyl group inserted by a C ₅ -C ₇ cycloalkylene group, a phenylene group, O, S, NR ₁₇ ; One or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, a C ₅ -C ₇ cycloalkyl group substituted by CN; or optionally one or more C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy, carboxy, C ₁ -C ₁₂ alkyl group, C ₅ -C ₆ cycloalkyl, formyl, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl group, a benzoyl group, XR ₁₇ , a halogen atom, a phenyl group substituted by CN; R ₁₇ is a C ₁ -C ₄ alkyl group; and R ₁₈ and R ₁₉ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkane. group, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl One of: one or more halogen atoms, C ₁ -C ₄ alkyl, C ₃ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy a C ₁ -C ₁₈ alkyl group substituted with a group; or any C ₂ -C ₁₈ alkyl group inserted by one or more C ₃ -C ₇ cycloalkylene groups, phenylene groups, O, S, NR ₁₇ ; Or any C ₅ -C ₇ cycloalkyl group substituted by one or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, CN; or optionally one or more C ₁ -C ₄ alkyl groups, a carboxyl group , C ₁ -C ₁₂ alkyl acyl group, C ₅ -C ₆ cycloalkyl formyl group, C ₂ -C ₄ alkyl acyl group substituted by C ₅ -C ₆ cycloalkyl group, aryl acyl group, XR ₁₇ , phenyl group , a halogen atom, CN substituted phenyl _{group; R 20, R 21, R} 22, R 23 are each independently selected from the group consisting of the following: a hydrogen atom, C ₁ -C ₁₈ alkyl, C ₃ -C ₇ One of cycloalkyl groups; or a C ₁ -C ₁₈ alkyl group substituted by halogen, CN, C ₁ -C ₄ alkoxy; or one or more oxygen atoms, C ₅ -C ₇ cycloalkylene a C ₂ -C ₁₈ alkyl group in which a phenylene group is inserted; or a C ₁ -C ₃ alkyl group substituted by a phenyl group or a C ₃ -C ₇ cycloalkyl group; or a phenyl group, a naphthyl group or a benzoyl group; Or optionally halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio, NR ₂₄ R ₂₅ , C ₁ -C ₁₂ alkyl a phenyl group substituted with a benzoyl group, a naphthyl group, a benzoyl group; each of R ₂₄ and R ₂₅ is a C ₁ -C ₄ alkyl group; or NR ₂₄ R ₂₅ together is a morpholine, a piperidine, a piperazine, N-methylpiperazine or pyrrole.

A ketoxime compound, such as a compound of formula V: Wherein Ar _{1 is} selected from a C ₆ -C ₂₀ o-arylene or C ₃ -C ₂₀ o-heteroaryl group substituted by X ₁ , a C ₆ -C ₂₀ o-arylene group or a C ₃ -C ₂₀ sub- The heteroaryl group is bonded to Y ₁ and a carbonyl group by two adjacent atoms to form a ring structure, and the substituents on the remaining atoms are each selected from the group consisting of a hydrogen atom, a halogen atom, and a C ₁ -C ₁₂ alkyl group. , C ₅ -C ₇ cycloalkyl, C ₅ -C ₇ cycloalkyl substituted C ₁ -C ₄ alkyl, C _1- C ₁₂ alkoxy, C ₁ -C ₄ alkylbenzyl group, C _1- C ₃ alkylenedioxy, R ₂ C(O)O, C ₁ -C ₁₂ alkylthio, C ₁ -C ₄ alkylphenylthio, CN, carboxyl, C ₁ -C ₁₂ alkane Oxycarbonyl, arylcarbonyl, heteroarylcarbonyl, X ₃ R ₁₈ , C ₁ -C ₄ alkylphenoxy, C1-C8 alkyl acyl phenoxy, C ₅ -C ₆ cycloalkyl acyl oxy a C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy group, an aryl acyl phenoxy group, a heteroaryl acyl phenoxy group, a R ₂ C(O)O substituted C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylphenylthio, C ₁ -C ₈ alkyl phenyl phenylthio, C ₅ -C ₆ cycloalkyl acyl phenylthio, C ₅ -C ₆ ring Alkyl-substituted C ₁ -C ₄ alkyl acyl phenylthio, aryl Alkyl phenylthio, heteroaryl acyl phenylthio; or C substituted by one or more C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ alkylbenzyloxy, R ₂ C(O)O ₁ -C ₄ alkoxy; or phenyl, or optionally substituted by one or more C ₁ -C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl acyl, aryl acyl, heteroaryl acyl, X ₃ R ₁₇ , phenyl, halogen atom, CN substituted phenyl; epoxypropyl group, wherein the epoxy group is arbitrarily condensed with a C ₁ -C ₄ alkyl aldehyde, a ketone; X _{3 is} selected from the group consisting of the following O , S or NR _22; Ar ₂ is selected from: Ar ₁ and X ₁ through C ₆ -C ₂₀ connected arylene group, by X ₁ C ₃ -C ₂₀ heteroarylene group and Ar ₁ is connected; or by When X ₁ is bonded to Ar ₁ , the Ar ₂ carbon atom ortho to X _{1 is} bonded to a straight bond, a carbon atom, a carbonyl group, O, S, NR ₁₈ and Ar ₁ to form a cyclic structure; X _{1 is} composed of the following: The group is selected: O, S, NR ₁₈ or Y ₂ -Z ₁ -Y ₂ ; Y1 is selected from the group consisting of: (CH ₂ ) _m CR ₁₅ R ₁₆ , NR ₁₉ , O (CR ₁₅ R _{16 m} , S(CR ₁₅ R ₁₆ ) _m , (CR ₁₅ R ₁₆ ) _m C=O and S=O, m is 0 or 1; Z ₁ is selected from the group consisting of C ₁ - C ₁₀ straight Chain Group, C ₁ -C ₁₀ branched alkylene, substituted by one or more oxygen atom or sulfur atom attached to the end groups C ₁ -C ₁₀ straight chain alkylene group, are connected one or more oxygen atom or sulfur atom, the end groups C ₁ -C ₁₀ branched alkylene, substituted by one or more oxygen atoms or sulfur atom inserted straight chain C ₂ -C ₁₀ alkylene group, substituted with one or more oxygen atom or a sulfur atom An inserted C ₂ -C ₁₀ branched alkylene group, an unsubstituted C ₆ -C ₂₀ arylene group, or a substituted C ₆ -C ₂₀ arylene group; Y ₂ is selected from the group consisting of :O, S, NR ₁₈ or OC(O); R ₁ is selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a diphenylphosphonyl group, and a di(C ₁ -C ₄ alkoxy group). a C ₂ -C ₁₈ alkyl group optionally substituted by one or more C ₃ -C ₇ cycloalkyl groups, phenyl, OR ₂₀ , SR ₂₁ , NR ₂₂ R ₂₃ wherein C ₂ - The phenyl group of the C ₁₈ alkyl group is any one or more of halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ - C ₄ alkanoyloxy, aroyloxy substituted; or C ₃ -C ₇ inserted cycloalkylene, _{phenylene, O, S, NR 22 C} 2 -C 18 Group; C ₃ -C ₈ cycloalkyl, CN, NO _2, phenyl; or any one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, Phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted phenyl; or C ₁ -C ₁₂ alkyl acyl, C ₁ -C ₁₂ alkoxycarbonyl, wherein alkane Any group substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₃ R ₂₀ ; or C ₁ -C ₁₂ An alkyl acyl group, a C ₁ -C ₁₂ alkoxycarbonyl group, wherein the alkyl group is optionally interrupted by one or more phenylene groups, X ₃ ; or a phenyl group unsubstituted benzoyl group, phenoxycarbonyl group; or benzene A benzoyl group or a phenoxy group substituted by any one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₂ R ₂₀ Alkylcarbonyl; R ₁₅ and R ₁₆ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₁ -C ₅ alkyl group substituted by a carboxyl group, and a C ₁ -C ₄ alkoxy group. substituted acyl C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl which One; or optionally substituted with one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkoxy a C ₂ -C ₁₈ alkyl group substituted with an acyloxy group or an aroyloxy group; or a C ₂ -C ₁₈ alkane inserted by a C ₅ -C ₇ cycloalkylene group, a phenylene group, O, S, NR ₁₇ Or any C ₅ -C ₇ cycloalkyl substituted by one or more C ₁ -C ₄ alkyl, phenyl, halogen atom, CN; or optionally C ₁ -C ₄ alkyl , C ₁ -C ₄ alkoxy, carboxy, C ₁ -C ₁₂ alkyl acyl, C ₅ -C ₆ cycloalkyl formyl, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl acyl , benzoyl, XR ₁₇ , a halogen atom, a phenyl group substituted by CN; R ₁₇ is a C ₁ -C ₄ alkyl group; and R ₁₈ and R ₁₉ are each independently selected from the group consisting of: a hydrogen atom, C ₁ -C ₁₈ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ One of a cycloalkyl group, a phenyl group; or any one or more halogen atoms, C ₁ -C ₄ alkyl group, C ₃ -C ₇ cycloalkyl group, heterocycloalkyl group, phenyl group, heteroaryl group, CN , C ₁ -C ₄ alkanoyl a C ₁ -C ₁₈ alkyl group substituted with an oxy group or an aroyloxy group; or any C ₂ inserted by one or more C ₃ -C ₇ cycloalkylene groups, phenylene groups, O, S, NR ₁₇ -C ₁₈ alkyl; or any C ₅ -C ₇ cycloalkyl substituted by one or more C ₁ -C ₄ alkyl, phenyl, halogen atom, CN; or optionally by one or more C ₁ - C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl group, C ₅ -C ₆ cycloalkyl, formyl, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl group, aryl group , XR ₁₇ , phenyl, halogen atom, phenyl substituted by CN; R ₂₀ , R ₂₁ , R ₂₂ , R ₂₃ are each independently selected from the group consisting of: hydrogen atom, C ₁ -C ₁₈ alkyl group One of C ₃ -C ₇ cycloalkyl groups; or a C ₁ -C ₁₈ alkyl group substituted by halogen, CN, C ₁ -C ₄ alkoxy group; or by one or more oxygen atoms, C ₅ - a C ₇ cycloalkylene group, a C ₂ -C ₁₈ alkyl group in which a phenylene group is inserted; or a C ₁ -C ₃ alkyl group substituted by a phenyl group or a C ₃ -C ₇ cycloalkyl group; or a phenyl group or a naphthalene group Or benzoyl; or optionally halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio, NR ₂₄ R ₂₅ , a C ₁ -C ₁₂ alkyl acyl group, a phenyl group substituted with a benzoyl group, a naphthyl group, a benzoyl group; each of R ₂₄ and R ₂₅ is a C ₁ -C ₄ alkyl group; or is NR ₂₄ R ₂₅ together? Porphyrin, piperidine, piperazine, N-methylpiperazine, pyrrole.

The invention further provides an intermediate of an asymmetric diterpene ester compound, which is a diketone oxime compound, comprising one of the group consisting of the following compounds of the formula VI and VII:

Wherein Ar _{1 is} selected from a C ₆ -C ₂₀ o-arylene or C ₃ -C ₂₀ o-heteroaryl group substituted by X ₁ , a C ₆ -C ₂₀ o-arylene group or a C ₃ -C ₂₀ sub- The heteroaryl group is bonded to Y ₁ and a carbonyl group by two adjacent atoms to form a ring structure, and the substituents on the remaining atoms are each selected from the group consisting of a hydrogen atom, a halogen atom, and a C ₁ -C ₁₂ alkyl group. , C ₅ -C ₇ cycloalkyl, C ₅ -C ₇ cycloalkyl substituted C ₁ -C ₄ alkyl, C _1- C ₁₂ alkoxy, C ₁ -C ₄ alkylbenzyl group, C _1- C ₃ alkylenedioxy, R ₂ C(O)O, C ₁ -C ₁₂ alkylthio, C ₁ -C ₄ alkylphenylthio, CN, carboxyl, C ₁ -C ₁₂ alkane Oxycarbonyl, arylcarbonyl, heteroarylcarbonyl, X ₃ R ₁₈ , C ₁ -C ₄ alkylphenoxy, C1-C8 alkyl acyl phenoxy, C ₅ -C ₆ cycloalkyl acyl oxy a C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy group, an aryl acyl phenoxy group, a heteroaryl acyl phenoxy group, a R ₂ C(O)O substituted C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylphenylthio, C ₁ -C ₈ alkyl phenyl phenylthio, C ₅ -C ₆ cycloalkyl acyl phenylthio, C ₅ -C ₆ ring Alkyl-substituted C ₁ -C ₄ alkyl acyl phenylthio, aryl Alkyl phenylthio, heteroaryl acyl phenylthio; or C substituted by one or more C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ alkylbenzyloxy, R ₂ C(O)O ₁ -C ₄ alkoxy; or phenyl and optionally by one or more C ₁ -C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl acyl, aryl acyl, heteroaryl acyl, X ₃ R ₁₇ a phenyl group, a halogen atom, a CN-substituted phenyl group; or a glycidyl group, wherein the epoxy group is arbitrarily condensed with a C ₁ -C ₄ alkyl aldehyde, a ketone; X _{3 is} selected from O, S or NR ₂₂ ; Ar _is selected from: Ar ₁ and X ₁ through C ₆ -C ₂₀ connected arylene group, and X ₁ through Ar C ₃ -C ₂₀ heteroarylene group ₁ is connected; or X ₁ and connected by Ar ₁ When the Ar ₂ carbon atom ortho to X _{1 is} bonded to a straight bond, a carbon atom, a carbonyl group, O, S, NR ₁₈ and Ar ₁ to form a cyclic structure; X ₁ is selected from the group consisting of: O, S, NR ₁₈ or Y ₂ -Z ₁ -Y ₂ ; Y1 is selected from the group consisting of: (CH ₂ ) _m CR ₁₅ R ₁₆ , NR ₁₉ , O(CR ₁₅ R ₁₆ ) _m , S (CR ₁₅ R ₁₆ ) _m , (CR ₁₅ R ₁₆ ) _m C=O and S=O, m is 0 or 1; Z ₁ is selected from the group consisting of C ₁ -C ₁₀ linear alkylene, C ₁ -C ₁₀ branched alkylene Group, with one or more oxygen atom or sulfur atom attached to the end groups C ₁ -C ₁₀ straight chain alkylene group, are connected in end groups one or more oxygen atom or a sulfur atom, C ₁ -C ₁₀ branched alkylene group, substituted with one or more oxygen atoms or sulfur atom inserted C ₂ -C ₁₀ linear alkylene, the alkylene is one or more oxygen atom or sulfur atom inserted branched C ₂ -C ₁₀ group, a group of unsubstituted C ₆ -C ₂₀ arylene group, or an optionally substituted C ₆ -C ₂₀ arylene group; Y ₂ by the group selected consisting of the following: O, S, NR _18, or OC (O R ₁ is selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a diphenylphosphonyl group, a di(C ₁ -C ₄ alkoxy)phosphonyl group; or any one or more a C ₂ -C ₁₈ alkyl group substituted by C ₃ -C ₇ cycloalkyl, phenyl, OR ₂₀ , SR ₂₁ , NR ₂₂ R ₂₃ wherein the phenyl group of the C ₂ -C ₁₈ alkyl group is either a plurality of halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy Substituted; or C ₂ -C ₁₈ alkyl group inserted by C ₃ -C ₇ cycloalkylene, phenylene, O, S, NR ₂₂ ; C ₃ -C ₈ cycloalkyl, CN, NO ₂ , phenyl; or any one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted phenyl; or C ₁ -C ₁₂ alkyl acyl, C ₁ -C ₁₂ alkoxycarbonyl, wherein the alkyl group is optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₃ R ₂₀ substituted; or C ₁ -C ₁₂ alkyl acyl, C ₁ -C ₁₂ alkoxy a carbonyl group in which an alkyl group is optionally interrupted by one or more phenylene groups, X ₃ ; or a phenyl group unsubstituted benzoyl group, phenoxycarbonyl group; or a phenyl group by any one or more halogen atoms, C _1- C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₂ R ₂₀ substituted benzoyl, phenoxycarbonyl; R ₁₅ , R ₁₆ are each independently is selected from the group consisting of the following: a hydrogen atom, C ₁ -C ₁₈ alkyl, carboxy substituted C ₁ -C ₅ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, wherein one phenyl group; or optionally a Or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aryloxy acyloxy a C ₂ -C ₁₈ alkyl group substituted by a group; or a C ₂ -C ₁₈ alkyl group inserted by a C ₅ -C ₇ cycloalkylene group, a phenylene group, O, S, NR ₁₇ ; optionally one or more a C ₁ -C ₄ alkyl group, a phenyl group, a halogen atom, a C ₅ -C ₇ cycloalkyl group substituted by CN; or optionally one or more C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy a group, a carboxyl group, a C ₁ -C ₁₂ alkyl acyl group, a C ₅ -C ₆ cycloalkyl formyl group, a C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl acyl group, a benzoyl group, XR ₁₇ , a halogen atom, a phenyl group substituted by CN; R ₁₇ is a C ₁ -C ₄ alkyl group; and R ₁₈ and R ₁₉ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, C group ₁ -C ₄ alkoxy substituted C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl wherein the Or any one or more halogen atoms, C ₁ -C ₄ alkyl, C ₃ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyl Oxyl and aroyloxy The C ₁ -C ₁₈ alkyl; or optionally substituted with one or more C ₃ -C ₇ cycloalkylene, phenylene, O, S, NR ₁₇ inserted C ₂ -C ₁₈ alkyl; or optionally One or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, a C ₅ -C ₇ cycloalkyl group substituted by CN; or optionally one or more C ₁ -C ₄ alkyl groups, a carboxyl group, C ₁ -C ₁₂ alkyl acyl group, C ₅ -C ₆ cycloalkyl formyl group, C ₂ -C ₄ alkyl acyl group substituted by C ₅ -C ₆ cycloalkyl group, aryl acyl group, XR ₁₇ , phenyl group, halogen atom a phenyl group substituted by CN; R ₂₀ , R ₂₁ , R ₂₂ and R ₂₃ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₃ -C ₇ cycloalkyl group; One of them; or a C ₁ -C ₁₈ alkyl group substituted by halogen, CN, C ₁ -C ₄ alkoxy; or by one or more oxygen atoms, C ₅ -C ₇ cycloalkylene, phenylene a C ₂ -C ₁₈ alkyl group inserted; or a C ₁ -C ₃ alkyl group substituted by a phenyl group, a C ₃ -C ₇ cycloalkyl group; or a phenyl group, a naphthyl group, a benzoyl group; halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy, _{phenylthio, NR 24 R 25, C 1} -C 12 alkyl group Benzoyl substituted phenyl group, a naphthyl group, a benzoyl group; R _24, R ₂₅ are each C ₁ -C ₄ alkyl; or NR ₂₄ R ₂₅ together are morpholine, piperidine, piperazine, N- methyl Piperazine, pyrrole.

The invention further provides a photocurable composition comprising a photoinitiator and at least one carbon-carbon double bond compound which is capable of undergoing free radical polymerization, the photoinitiator comprising at least one of the foregoing asymmetric diterpene ester compounds.

The invention further proposes the use of a photocurable composition for first producing one of the following colored or transparent articles: a coating, an ink, a binder, a photoresist or light. The resist is used for printing, 3D printing, color filter production in display devices, electronic device packaging, and printed circuit board dielectric layers.

The present invention further provides a method for curing a photocurable composition, which comprises applying the photocurable composition described above to a substrate, and curing the coating layer by irradiation with light having a wavelength of from 190 to 600 nm.

The invention further provides a method for preparing a convex pattern by using a photocurable composition, which first dilutes the photocurable composition with a solvent; then applies the diluted photocurable composition to a substrate, and is dried, exposed, The developing method removes the unexposed portion to obtain a raised pattern.

The invention further provides a color filter comprising black, red, green and blue primitives, comprising a composition comprising the asymmetric diterpene ester compound, a photocurable monomer, an alkali soluble resin, a pigment and an additive, The order is obtained by coating, exposure, development, and heat treatment.

The invention further provides a method for manufacturing a color filter, comprising black, red, green and blue primitives, which will contain at least one of the aforementioned asymmetric diterpene ester compounds, photocurable monomers, alkali soluble resins, pigments and additives. The composition is sequentially coated, exposed, developed, and heat-treated, and finally the color filter is obtained.

Therefore, the main object of the present invention is to propose an asymmetry comprising structural formula I. The diterpene ester compound has very excellent photoinitiating activity.

A further object of the present invention is to provide a photocurable composition comprising the asymmetric diterpene ester compound of the formula I, a method for its production and related applications, which have good photoinitiating activity and therefore have good Photographic performance.

A further object of the present invention is to provide a color filter and a method for producing the asymmetric diterpene ester compound of the formula I having a color filter having a very good optical structure. characteristic.

Series 1: Structure of a compound of formula I, expressed as follows: Wherein, Ar ₁ is substituted with X ₁ being C ₆ -C ₂₀ arylene group or o-C ₃ -C ₂₀ heteroarylene group ortho, ortho-C ₆ -C ₂₀ arylene or C ₃ -C ₂₀ heteroarylene o The two adjacent atoms are bonded to Y ₁ and a carbonyl group to form a ring structure, and the substituents on the remaining atoms are each: a hydrogen atom, a halogen atom, a C ₁ -C ₁₂ alkyl group, a C ₅ -C ₇ cycloalkyl group. One of a C ₅ -C ₇ cycloalkyl substituted C ₁ -C ₄ alkyl group, a C ₁ -C ₁₂ alkoxy group; or one or more C ₁ -C ₁₂ alkoxy groups, C ₁ -C _{a 4} -alkylbenzyloxy group, a R ₂ C(O)O substituted C ₁ -C ₄ alkoxy group; or a phenyl group; or optionally exemplified by one or more C ₁ -C ₄ alkyl groups, a carboxyl group, C ₁ - C ₁₂ alkyl acyl, aryl acyl, heteroaryl acyl, X ₃ R ₁₇ , phenyl, halogen atom, CN substituted phenyl; C ₁ -C ₄ alkylbenzyloxy, R ₂ C(O)O Substituted C ₁ -C ₄ alkoxy, C ₁ -C ₃ alkylenedioxy, R ₂ C(O)O, C ₁ -C ₁₂ alkylthio, C ₁ -C ₄ alkylbenzene sulfur Base, CN, carboxyl group, C ₁ -C ₁₂ alkoxycarbonyl group, arylcarbonyl group, heteroarylcarbonyl group, X ₃ R ₁₈ , C ₁ -C ₄ alkylphenoxy group, C ₁ -C ₈ alkyl acylbenzene Oxy, C ₅ -C ₆ cycloalkyl acyl phenoxy, C _5- C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy, C ₁ -C ₃ alkylenedioxy, aryl acyl phenoxy, heteroaryl acyl phenoxy, R ₂ C(O)O substituted C ₁ -C ₄ alkylthio group, R ₂ C(O)O substituted C ₁ -C ₄ alkylphenylthio group, C ₁ -C ₈ alkyl acyl phenylthio group, C _5- C ₆ cycloalkyl phenyl phenylthio, C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl phenyl phenylthio, aryl acyl phenylthio, heteroaryl acyl phenylthio; Is a glycidyl group in which an epoxy group is arbitrarily condensed with a C ₁ -C ₄ alkyl aldehyde or a ketone; X ₃ is O, S or NR ₂₂ ; Ar ₂ is a C ₆ -C ₂₀ arylene group, C ₃ - C ₂₀ heteroarylene group, ₁ is connected via X ₁ and Ar; or _a connected simultaneously, the substituent X ₁ ortho to the Ar ₂ carbon atoms by a direct bond, a carbon atom, a carbonyl residue, O by X ₁ and Ar, S, NR _{18 is} further connected to Ar ₁ to form a cyclic structure; n is 0 or 1; X ₁ is O, S, NR ₁₈ or Y ₂ -Z ₁ -Y ₂ ; Y ₁ is (CH ₂ ) _m CR ₁₅ R ₁₆ , NR ₁₉ , O(CR ₁₅ R ₁₆ ) _m , S(CR ₁₅ R ₁₆ ) _m , (CR ₁₅ R ₁₆ ) _m C=O, S=O; m is 0 or 1; Z ₁ is C ₁ -C ₁₀ straight chain alkylene or C ₁ -C ₁₀ branched alkylene; or by one or more oxygen A sulfur atom attached ₁ -C ₁₀ linear alkylene groups at the end C; by one or more oxygen, sulfur atom attached to the end groups C ₁ -C ₁₀ branched alkylene; or by one or more a C ₁ -C ₁₀ linear alkylene group in which oxygen or a sulfur atom is inserted; or a C ₁ -C ₁₀ branched alkylene group inserted by one or more oxygen or sulfur atoms; an unsubstituted or substituted C ₆ -C ₂₀ arylene; Y ₂ is O, S, NR ₁₈ or OC(O); R ₁ is selected from the group consisting of: a hydrogen atom, a C ₂ -C ₁₈ alkyl group; or any one or more C ₃ -C ₇ cycloalkyl, phenyl, OR ₂₀ , SR ₂₁ , NR ₂₂ R ₂₃ substituted C ₂ -C ₁₈ alkyl, wherein the C ₂ -C ₁₈ alkyl phenyl group is any one or more Halogen atom, C ₁ -C ₄ alkyl group, C ₅ -C ₇ cycloalkyl group, heterocycloalkyl group, phenyl group, heteroaryl group, CN, C ₁ -C ₄ alkanoyloxy group, aroyloxy group Or a C ₂ -C ₁₈ alkyl group inserted by a C ₃ -C ₇ cycloalkylene group, a phenylene group, an O, S, NR ₂₂ ; or a C ₃ -C ₈ cycloalkyl group, CN, NO ₂ , a phenyl group; Or optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy base, Acyloxy-substituted phenyl; or R ₁ is C ₁ -C ₁₂ alkyl group, C ₁ -C ₁₂ alkoxycarbonyl, wherein the alkyl group optionally substituted with one or more halogen atoms, C ₁ -C ₄ alkoxy Substituted, C ₅ or C ₆ cycloalkyl, phenyl, CN, OH, X ₃ R ₂₀ substituted; or R ₁ is C ₁ -C ₁₂ alkyl acyl, C ₁ -C ₁₂ alkoxycarbonyl, wherein alkyl Any one or two or more phenylene groups, X ₃ inserted; or R ₁ is a benzoyl group or a phenoxycarbonyl group which is unsubstituted by a phenyl group; or R ₁ is optionally one or two or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ cycloalkyl or C ₆ cycloalkyl, phenyl, CN, OH, X ₂ R ₂₀ substituted benzoyl, phenoxycarbonyl; or R ₁ is diphenylphosphino , a di(C ₁ -C ₄ alkoxy)phosphono group; R ₂ and R ₃ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₁ -C ₁₈ alkoxy group. Any one of a C ₅ -C ₇ cycloalkyl group or a phenyl group; or R ₂ and R ₃ are each independently optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ naphthenic , heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted and/or C _5- C ₇ cycloalkylene, phenylene, O, S, NR _{17 are} inserted into C ₂ -C ₁₈ alkenyl; or R ₂ , R ₃ are each independently optionally substituted by one or more halogen atoms, C ₁ - C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted C ₂ -C ₁₈ alkane Or a C ₂ -C ₁₈ alkyl group in which R ₂ and R ₃ are each independently inserted by a C ₅ -C ₇ cycloalkylene group, a phenylene group, an O, S, or NR ₁₇ ; or optionally a halogen or one or more halogens Atom, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted a C ₂ -C ₁₈ alkenyl group inserted by a C ₅ -C ₇ cycloalkylene group, a phenylene group, an O, S, or NR ₁₇ ; or a condition in which the aforementioned C ₂ -C ₁₈ alkyl group is substituted or inserted Or R ₂ and R ₃ are each independently independently substituted by one or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, or a C ₅ -C ₇ cycloalkyl group; or R ₂ and R ₃ are each independently Is a phenyl group or any phenyl group substituted by one or more C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy groups, phenyl groups, halogen atoms, CN; or R ₂ , R ₃ are each independently Is a naphthyl group or a naphthyl group optionally substituted by one or more C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy groups, phenyl groups, halogen atoms, CN; or R ₂ , R ₃ are each independently benzene An unsubstituted benzoyl group or a phenoxycarbonyl group; or R ₂ and R ₃ are each independently one or two or more halogen atoms, R ₁₇ , C ₅ cycloalkyl, C ₆ cycloalkyl, CN , OH, XR ₁₇ substituted benzoyl or phenoxycarbonyl; R ₁₅ and R ₁₆ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a carboxyl group substituted C ₁ - One of C ₅ alkyl, C ₁ -C ₄ alkoxyacyl substituted C ₁ -C ₅ alkyl, R ₂ C(O)O substituted C ₁ -C ₄ alkyl; or optionally one or more Halogen atom, C ₁ -C ₄ alkyl group, C ₅ -C ₇ cycloalkyl group, heterocycloalkyl group, phenyl group, heteroaryl group, CN, C ₁ -C ₄ alkanoyloxy group, aroyloxy group the C ₂ -C ₁₈ alkyl; or C ₅ -C ₇ cycloalkylene, phenylene, O, S, NR ₁₇ inserted into the C ₂ -C ₁₈ alkyl; or C ₂ -C ₁₈ alkyl the The conditions substituted or inserted are simultaneously present; or R ₁₅ and R ₁₆ are each independently C ₅ -C ₇ cycloalkyl; or optionally by one or a plurality of C ₁ -C ₄ alkyl, phenyl, halogen atom, CN substituted C ₅ -C ₇ cycloalkyl; or R ₁₅ , R ₁₆ are each independently phenyl; or optionally by one or more C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxy, C ₁ -C ₁₂ alkyl acyl, C ₅ -C ₆ cycloalkyl formyl, C ₅ -C ₆ cycloalkyl substituted C ₂ - a C ₄ alkyl acyl group, a benzoyl group, an XR ₁₇ group, a phenyl group, a halogen atom, a CN-substituted phenyl group; or R ₁₅ and R ₁₆ together with a carbon atom or a ruthenium atom to which they are attached constitute a cyclic and ring-shaped atom The number is 4-7; or R ₁₅ and R ₁₆ together with adjacent substituents form a cyclic ring and the number of atoms in the ring is 4-7; R ₁₇ is a C ₁ -C ₄ alkyl group; R ₁₈ , R ₁₉ Each is independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₁ -C ₄ alkoxyacyl substituted C ₁ -C ₅ alkyl group, and a R ₂ C(O)O substitution. One of C ₁ -C ₄ alkyl groups; or optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₃ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl , CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted C ₁ -C ₁₈ alkyl; or optionally substituted by one or more C ₃ -C ₇ hypocycloalkanes a C ₂ -C ₁₈ alkyl group in which the phenylene group, the phenylene group, the O, S, and NR _{17 are} inserted; or each of R ₁₈ and R _{19 is} independently a C ₅ -C ₇ cycloalkyl group; or optionally one or more C ₁ -C ₄ alkyl, phenyl, halogen atom, CN substituted C ₅ -C ₇ cycloalkyl; or R ₁₈ , R ₁₉ are each independently phenyl; or optionally by one or more C ₁ -C ₄ alkane a group, a carboxyl group, a C ₁ -C ₁₂ alkyl acyl group, a C ₅ -C ₆ cycloalkyl formyl group, a C ₅ -C ₆ cycloalkyl group substituted C ₂ -C ₄ alkyl acyl group, an aryl acyl group, XR ₁₇ , a phenyl group, a halogen atom, a CN-substituted phenyl group; or the above R ₁₈ is bonded to an aromatic ring in Ar ₁ or Ar ₂ through a straight bond, a carbon atom or a carbonyl group to form a new ring; or the above R ₁₉ is bonded through a straight bond or a carbon atom. The carbonyl group is bonded to the aromatic ring in Ar ₁ to form a new ring; R _20, R ₂₁ , R ₂₂ and R ₂₃ are each independently selected from the group consisting of hydrogen atom, C ₁ -C ₁₈ alkyl group, One of a halogen, CN, C ₁ -C ₄ alkoxy-substituted C ₁ -C ₁₈ alkyl group, a C ₃ -C ₇ cycloalkyl group; or one or more oxygen atoms, a C ₅ -C ₇ subring a C ₂ -C ₁₈ alkyl group in which an alkyl group or a phenylene group is inserted; or a C ₁ substituted by a phenyl group or a C ₃ -C ₇ cycloalkyl group -C ₃ alkyl; or R ₂₀ , R ₂₁ , R ₂₂ , R ₂₃ are each independently phenyl, naphthyl unsubstituted phenyl, naphthyl, benzoyl; or R ₂₀ , R ₂₁ , R ₂₂ And R ₂₃ are each independently halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio, NR ₂₄ R ₂₅ , C ₁ -C ₁₂ alkyl acyl, benzoyl substituted phenyl, naphthyl, benzoyl; R ₂₄ , R ₂₅ are each C ₁ -C ₄ alkyl; or NR ₂₄ R ₂₅ is morpholine, Acridine, pyridazine, N-methylpyridazine, pyrrole.

Series 2: Compounds of the general formula II, IIIA and IIIB, as shown below:

Wherein R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ and R ₁₄ are each independently: hydrogen atom, halogen atom, C ₁ -C ₁₂ Alkyl, C ₅ -C ₇ cycloalkyl, C ₅ -C ₇ cycloalkyl substituted C ₁ -C ₄ alkyl, C ₁ -C ₁₂ alkoxy, phenyl, C ₁ -C ₄ alkylbenzyl One of the oxy groups; or any one or more of C ₁ -C ₄ alkyl groups, carboxyl groups, C ₁ -C ₁₂ alkyl acyl groups, aryl acyl groups, heteroaryl acyl groups, X ₃ R ₁₇ , phenyl groups, halogens atoms, CN substituted phenyl; or with one or more C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ alkylbenzyl group, R ₂ C (O) O-substituted C ₁ -C ₄ alkoxy Or R ₂ C(O)O, CN, carboxyl, C ₁ -C ₁₂ alkoxycarbonyl, arylcarbonyl, heteroarylcarbonyl, X ₃ R ₁₈ ; or C ₁ -C ₄ alkylphenoxy , C ₁ -C ₄ alkylphenylthio, C ₁ -C ₈ alkyl acyl phenoxy, aryl acyl phenoxy, heteroaryl acyl phenoxy, C ₅ -C ₆ cycloalkyl acyl Alkyl, C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy, C ₁ -C ₃ alkylenedioxy, C ₁ -C ₁₂ alkylthio, R ₂ C (O)O substituted C ₁ -C ₄ alkylthio, R ₂ C(O)O substitution C ₁ -C ₄ alkylphenylthio, C ₁ -C ₈ alkyl phenyl phenylthio, aryl acyl phenylthio, heteroaryl acyl phenylthio, C ₅ -C ₆ cycloalkyl phenyl thio a C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenylthio group; or R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ and R ₁₄ are each independently a propylene group, wherein the epoxy group is arbitrarily condensed with a C ₁ -C ₄ alkyl aldehyde or a ketone; X ₁ is O, S or NR ₁₈ ; X ₂ is O, S or NR ₁₉ , Y ₁ is O, S or CR ₁₅ R ₁₆ ; other substituents are defined in the same series 1.

Series 3: In the compound of the formula II: R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ are all hydrogen atoms; X ₁ is O or S; Y ₁ is CH ₂ , CHCH ₃ or C(CH ₃ ) ₂ ; n=1; R ₁ is C ₁ -C ₁₂ alkyl or optionally substituted by one or more C ₃ -C ₇ cycloalkyl, phenyl, OR ₂₀ , SR ₂₁ , NR ₂₂ R ₂₃ -substituted C ₁ -C ₁₂ alkyl; R ₂ and R ₃ are each independently methyl, ethyl, phenyl, 2-methylphenyl, 3-methylphenyl, 2,4,6- One of trimethylphenyl or 2,6-dimethoxyphenyl; the other groups are defined as the corresponding groups of formula II in series 2.

Series 4: In the compounds of the formulae IIIA and IIIB: X ₂ is NR ₁₉ ; Y ₁ is O, S or CR ₁₅ R ₁₆ ; R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ are each independently a hydrogen atom, a halogen Atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylbenzyloxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylphenoxy One of the C ₁ -C ₄ alkylphenylthio groups; the other substituents are as defined for the corresponding groups of the formulae IIIA and IIIB of the above series 2.

Series 5: In the structural formula IIIA and IIIB compounds: Y ₁ is CH ₂ or CHCH ₃ ; n=0; R ₁ is C ₁ -C ₁₂ alkyl or optionally C ₃ -C ₇ cycloalkyl, Phenyl, OR ₂₀ , SR ₂₁ , NR ₂₂ R ₂₃ substituted C ₁ -C ₁₂ alkyl; R ₂ and R ₃ are each independently methyl, ethyl, phenyl, 2-methylphenyl, 3- Methylphenyl, 2,4,6-trimethylphenyl or 2,6-dimethoxyphenyl; R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ are each independently a hydrogen atom or C ₁ -C ₄ alkoxy; R ₁₉ is C ₁ -C ₁₂ alkyl or C ₃ -C ₇ cycloalkyl, phenyl-substituted C ₁ -C ₃ alkyl; other groups are as defined in formula 4 series and ⅲA The corresponding group definition in IIIB.

In the above compounds of the formulae i, IIIA and IIIB, R ₂ C(O) or R ₃ C(O) may also be replaced by (R ₂ ) ₂ P or R ₂ S(O ₂ ) to form the corresponding phosphorous (phosphine). Acid esters or sulfonates also have photoinduced free radical or photocationic cations.

Series 6: The respective structural formula I, II, IIIA and IIIB compounds of the above series 1-5, the specific structures of which are:

The present invention also provides a process for the preparation of the compound of the formula I in the series 1, comprising the steps of: (1) Step 1: Selecting on the ortho-methylene group of the cyclopentanone carbonyl group in the following compound of the formula IV; The method of deuteration and deuteration is to carry out a oximation reaction of a compound of the formula IV with an alkyl nitrite in an acidic solution to obtain a corresponding intermediate, which is a ketone oxime compound, such as the following compound of the formula V;

(2) The second step: the intermediate structure V compound is further subjected to the second deuteration, and the following two methods are available: Method A: the compound of the formula V and the alkyl nitrite are deuterated in an acidic solution. Obtaining a compound corresponding to the second intermediate structure of the formula VI; Method B: the compound of the formula V is subjected to a oximation reaction of a carbonyl group in a side chain R ₁ CH ₂ CO in a hydroxylamine solution to obtain a corresponding second intermediate structure formula a compound of formula VII; when a cis-trans isomer is present in the thiol group, the resulting compound of formula VI, VII is a mixture of its respective isomers;

(3) The third step: the above second deuterated intermediate structure of the compound of the formula VI or VII with the following acylating reagent: Or an equivalent acylating reagent is esterified to obtain a compound of the above formula I; when the thiol group of the compound of formula VI or VII is present in the cis-trans isomer, the obtained compound of formula I is Mixtures of isomers, or after purification to obtain individual isomers, all groups of the structures involved in the above reaction are defined in the same way as the corresponding structural groups in series 1.

The invention also provides an asymmetric diketone compound comprising a compound of the formula IV, as shown below:

Wherein the radicals _{Ar 1, Ar 2, X 1} , defined Y _1, R ₁ of the same series in a compound of Formula I structure corresponding groups defined above; further, X ₃ is O, S or NR _22; Z ₁ is the following One of the group: C ₁ -C ₁₀ linear alkylene, C ₁ -C ₁₀ branched alkylene, C ₁ -C ₁₀ straight bonded to the end group by one or more oxygen or sulfur atoms a chain alkylene group, a C ₁ -C ₁₀ branched alkylene group bonded to a terminal group by one or more oxygen atoms or a sulfur atom, and a C ₂ -C ₁₀ straight inserted by one or more oxygen atoms or sulfur atoms a chain alkylene group, a C ₂ -C ₁₀ branched alkylene group inserted by one or more oxygen atoms or sulfur atoms, an unsubstituted C ₆ -C ₂₀ arylene group, or a substituted C ₆ - C ₂₀ arylene; Y ₂ is O, S, NR ₁₈ or OC(O); R ₁₅ and R ₁₆ are each independently one of the following groups: a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a carboxyl group substituted C ₁ -C ₅ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; or any one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl , Heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy, substituted C ₂ -C ₁₈ alkyl; or C ₅ -C ₇ cycloalkylene, phenylene, O, a C ₂ -C ₁₈ alkyl group to which S, NR ₁₇ is inserted; or a C ₅ -C ₇ cycloalkyl group optionally substituted by one or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, or CN; Any one or more of C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxy, C ₁ -C ₁₂ alkyl acyl, C ₅ -C ₆ cycloalkyl formyl, C ₅ -C ₆ a cycloalkyl-substituted C ₂ -C ₄ alkyl acyl group, a benzoyl group, an XR ₁₇ group, a halogen atom, a phenyl group substituted by CN; R ₁₇ is a C ₁ -C ₄ alkyl group; and R ₁₈ and R ₁₉ are each independently wherein one of the following groups: a hydrogen atom, C ₁ -C ₁₈ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl, substituted with R ₂ C (O) O is C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; or optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₃ -C ₇ cycloalkyl, heterocycloalkane a C ₁ -C ₁₈ alkyl group substituted with a phenyl group, a heteroaryl group, a CN, a C ₁ -C ₄ alkanoyloxy group, an aroyloxy group; or optionally a one or more C ₃ -C ₇ subrings Alkyl, phenylene, O, S, N a C ₂ -C ₁₈ alkyl group in which R ₁₇ is inserted; or a C ₅ -C ₇ cycloalkyl group optionally substituted by one or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, or CN; One or more C ₁ -C ₄ alkyl, carboxyl, C ₁ -C ₁₂ alkyl acyl, C ₅ -C ₆ cycloalkyl formyl, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ An alkyl group, an aryl acyl group, an XR ₁₇ group, a phenyl group, a halogen atom, a phenyl group substituted by CN; R ₂₀ , R ₂₁ , R ₂₂ , and R ₂₃ are each independently one of the following groups: a hydrogen atom. , C ₁ -C ₁₈ alkyl, C ₃ -C ₇ cycloalkyl; or C ₁ -C ₁₈ alkyl substituted by halogen, CN, C ₁ -C ₄ alkoxy; or by one or more oxygen An atom, a C ₅ -C ₇ cycloalkylene group, a C ₂ -C ₁₈ alkyl group in which a phenylene group is inserted; or a C ₁ -C ₃ alkyl group substituted by a phenyl group, a C ₃ -C ₇ cycloalkyl group; Or phenyl, naphthyl, benzoyl; or optionally halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio , NR ₂₄ R ₂₅ , C ₁ -C ₁₂ alkyl acyl group, phenyl group substituted with benzoyl group, naphthyl group, benzoyl group; R ₂₄ and R ₂₅ are each a C ₁ -C ₄ alkyl group; or NR ₂₄ R ₂₅ together is morpholine, piperidine, piperazine, N-methylpiperazine, pyrrole.

The present invention also provides an intermediate of an asymmetric diketone compound, which is a ketone oxime compound, as shown by the following compound of the formula V:

Wherein the definition of the groups Ar ₁ , Ar ₂ , X ₁ , Y ₁ , R _{1 is} the same as the corresponding group of the compound of the formula I in the series 1; in addition, X ₃ is O, S or NR ₂₂ ; Z ₁ is the following group One of the group: a C ₁ -C ₁₀ linear alkylene group, a C ₁ -C ₁₀ branched alkylene group, a C ₁ -C ₁₀ linear chain attached to the terminal group by one or more oxygen or sulfur atoms An alkylene group, a C ₁ -C ₁₀ branched alkylene group bonded to a terminal group by one or more oxygen atoms or sulfur atoms, and a C ₂ -C ₁₀ linear chain inserted by one or more oxygen atoms or sulfur atoms. An alkylene group, a C ₂ -C ₁₀ branched alkylene group inserted by one or more oxygen atoms or sulfur atoms, an unsubstituted C ₆ -C ₂₀ arylene group, or a substituted C ₆ -C ₂₀ arylene; Y ₂ is O, S, NR ₁₈ or OC(O); R ₁₅ and R ₁₆ are each independently one of the following groups: a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a carboxyl group substituted C ₁ -C ₅ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ -cycloalkyl, phenyl; or any one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, An aryl group, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy, substituted C ₂ -C ₁₈ alkyl; or C ₅ -C ₇ cycloalkylene, phenylene, O, S, a C ₂ -C ₁₈ alkyl group to which NR ₁₇ is inserted; or any C ₅ -C ₇ cycloalkyl group substituted by one or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, CN; or any One or more C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy groups, carboxyl groups, C ₁ -C ₁₂ alkyl acyl groups, C ₅ -C ₆ cycloalkyl formyl groups, C ₅ -C ₆ naphthenes a substituted C ₂ -C ₄ alkyl acyl group, a benzoyl group, XR ₁₇ , a halogen atom, a phenyl group substituted by CN; R ₁₇ is a C ₁ -C ₄ alkyl group; and R ₁₈ and R ₁₉ are each independently the following One of the groups: a C ₁ -C ₅ alkyl group substituted by a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₁ -C ₄ alkoxy group, or a C substituted by R ₂ C(O)O ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; or optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₃ -C ₇ cycloalkyl, heterocycloalkyl , phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, a C ₁ -C ₁₈ alkyl group substituted with an aroyloxy group; or optionally substituted by one or more C ₃ -C ₇ hypocyclohexanes Base, phenylene, O, S, NR ₁₇ Inserted C ₂ -C ₁₈ alkyl; or any C ₅ -C ₇ cycloalkyl substituted by one or more C ₁ -C ₄ alkyl, phenyl, halogen atom, CN; or optionally by one or a plurality of C ₁ -C ₄ alkyl, carboxyl, C ₁ -C ₁₂ alkyl acyl, C ₅ -C ₆ cycloalkyl formyl, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl An acyl group, an aryl acyl group, an XR ₁₇ group, a phenyl group, a halogen atom, a phenyl group substituted by CN; R ₂₀ , R ₂₁ , R ₂₂ , and R ₂₃ are each independently one of the following groups: a hydrogen atom, C ₁ -C ₁₈ alkyl, C ₃ -C ₇ cycloalkyl; or C ₁ -C ₁₈ alkyl substituted by halogen, CN, C ₁ -C ₄ alkoxy; or by one or more oxygen atoms, a C ₅ -C ₇ cycloalkylene group, a C ₂ -C ₁₈ alkyl group in which a phenylene group is inserted; or a C ₁ -C ₃ alkyl group substituted by a phenyl group, a C ₃ -C ₇ cycloalkyl group; or a benzene group Or naphthyl, benzoyl; or optionally halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio, NR ₂₄ R ₂₅ , C ₁ -C ₁₂ alkyl acyl, phenyl substituted by benzoyl, naphthyl, benzoyl; each of R ₂₄ and R ₂₅ is C ₁ -C ₄ alkyl; or NR ₂₄ R _{2 5} together is morpholine, piperidine, piperazine, N-methylpiperazine or pyrrole.

The present invention also provides an intermediate of an asymmetric diketone compound, which is a diketone oxime compound, as shown by the following compounds of the formula VI, VII:

Wherein the definition of the groups Ar ₁ , Ar ₂ , X ₁ , Y ₁ , R _{1 is} the same as the corresponding group of the compound of the formula I in the series 1; in addition, X ₃ is O, S or NR ₂₂ ; Z ₁ is the following group One of the group: a C ₁ -C ₁₀ linear alkylene group, a C ₁ -C ₁₀ branched alkylene group, a C ₁ -C ₁₀ linear chain attached to the terminal group by one or more oxygen or sulfur atoms An alkylene group, a C ₁ -C ₁₀ branched alkylene group bonded to a terminal group by one or more oxygen atoms or sulfur atoms, and a C ₂ -C ₁₀ linear chain inserted by one or more oxygen atoms or sulfur atoms. An alkylene group, a C ₂ -C ₁₀ branched alkylene group inserted by one or more oxygen atoms or sulfur atoms, an unsubstituted C ₆ -C ₂₀ arylene group, or a substituted C ₆ -C ₂₀ arylene; Y ₂ is O, S, NR ₁₈ or OC(O); R ₁₅ and R ₁₆ are each independently one of the following groups: a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a carboxyl group substituted C ₁ -C ₅ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; or optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, Heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, C ₂ -C ₁₈ alkyl substituted by aroyloxy; or C ₅ -C ₇ cycloalkylene, phenylene, O, S , C ₂ -C ₁₈ alkyl group inserted in NR ₁₇ ; or any C ₅ -C ₇ cycloalkyl group substituted by one or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, CN; or any By one or more C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxy, C ₁ -C ₁₂ alkyl acyl, C ₅ -C ₆ cycloalkyl formyl, C ₅ -C ₆ ring An alkyl-substituted C ₂ -C ₄ alkyl acyl group, a benzoyl group, an XR ₁₇ group, a halogen atom, a phenyl group substituted by CN; R ₁₇ is a C ₁ -C ₄ alkyl group; and R ₁₈ and R ₁₉ are each independently one of the following groups: a hydrogen atom, C ₁ -C ₁₈ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; or optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₃ -C ₇ cycloalkyl, heterocycloalkyl , phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, a C ₁ -C ₁₈ alkyl group substituted with an aroyloxy group; or optionally substituted by one or more C ₃ -C ₇ hypocyclohexanes , phenylene, O, S, NR ₁₇ Insertion of C ₂ -C ₁₈ alkyl; or optionally substituted with one or more C ₁ -C ₄ alkyl group, a phenyl group, a halogen atom, CN substituted C ₅ -C ₇ cycloalkyl; or an optionally substituted with one or more a C ₁ -C ₄ alkyl, substituted by carboxy, C ₁ -C ₁₂ alkyl group, C ₅ -C ₆ cycloalkyl, formyl, C ₅ -C ₆ cycloalkyl C ₂ -C ₄ alkyl group , an aryl acyl group, an XR ₁₇ group, a phenyl group, a halogen atom, a phenyl group substituted by CN; R ₂₀ , R ₂₁ , R ₂₂ , and R ₂₃ are each independently one of the following groups: a hydrogen atom, C ₁ - C ₁₈ alkyl, C ₃ -C ₇ cycloalkyl; or C ₁ -C ₁₈ alkyl substituted by halogen, CN, C ₁ -C ₄ alkoxy; or by one or more oxygen atoms, C ₅ a C ₇ -cycloalkylene group, a C ₂ -C ₁₈ alkyl group in which a phenylene group is inserted; or a C ₁ -C ₃ alkyl group substituted by a phenyl group or a C ₃ -C ₇ cycloalkyl group; or a phenyl group; Naphthyl, benzoyl; or optionally halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio, NR ₂₄ R _25, C ₁ -C ₁₂ alkyl group, a benzoyl group substituted with phenyl group, a naphthyl group, a benzoyl group; R _24, R ₂₅ are each C ₁ -C ₄ alkyl; or a NR ₂₄ R ₂₅ Morpholine, piperidine, piperazine, N- methylpiperazine or pyrrole.

When the thiol group in the compound of the general formula V, VI, VII has a cis-trans isomer, the obtained intermediate and the final product of the compound of the formula I are a mixture of isomers thereof, and the purified individual can be obtained by separation. Structure.

The present invention also relates to a photocurable composition comprising a photoinitiator (a) and at least one carbon-carbon double bond compound (b) which is capable of undergoing radical polymerization, and the photoinitiator (a) comprises at least one asymmetric diterpene ester compound Containing the aforementioned compound of formula I.

The photoinitiator (a) further comprises, as a co-initiator component (c), in addition to the at least one of the aforementioned asymmetric diterpene ester compound structures of the formula I.

The photocurable composition further contains other additives (d) such as a developable resin, a pigment, an antifoaming agent and the like.

The photoinitiator (a) comprises from 0.05 to 25%, preferably from 2 to 15% by weight of the total of the cured composition; the balance of the remaining components in addition to the above components.

The carbon-carbon double bond compound (b) which can be subjected to radical polymerization is a photocurable monomer which includes a carbon-carbon double bond or two or more carbon-carbon double bonds in the molecule, and a compound containing one carbon-carbon double bond. (b) Preferred are acrylate compounds, methacrylate compounds, such as acrylates or methacrylates of monohydric alcohols: methyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, acrylic acid Isobornyl ester, hydroxyethyl acrylate, methyl methacrylate and acrylonitrile, N-dialkyl acrylamide, N-vinyl pyrrolidone, vinyl benzene, vinyl Acetate, vinyl ether.

a compound (b) comprising two or more carbon-carbon double bonds, such as an alkyl binary Acrylates or methacrylates of alcohols, polyols or polyester polyols, polyether polyols, epoxy resin polyols, acrylates of polyurethane polyols, vinyl ethers and unsaturated dicarboxylic acid polyols Saturated polyesters such as polyethylene glycol diacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate, polyethoxylated trimethylolpropane triacrylate, pentaerythritol tetraacrylate, two Pentaerythritol hexaacrylate, polyester oligomer acrylate, urethane oligomer acrylate, aromatic epoxy acrylate, maleic acid ethylene glycol polyester.

These carbon-carbon double bond compounds (b) can be used not only alone but also in two types. The above mixed use or mixture may be pre-copolymerized to form an oligomer for use in formulating the composition; when the polymerizable monomer contains an alkali-soluble group such as a carboxylic acid group, an alkali-soluble polymer resin is obtained, which can be used for preparing light. Resist or used to formulate a water-dispersible emulsion.

An asymmetric diterpene ester compound of the above formula I is used as a light guide In addition to the hair coloring agent, other types of commercially available photoinitiators or co-initiators may be compounded as co-initiator component (c), usually alpha-hydroxyketones such as 2-hydroxy-, depending on the needs of the photocurable composition. 2-methyl-1-propiophenone, 1-hydroxycyclohexyl benzophenone; α-amino ketones such as 2-methyl-2-morpholinyl-(4-methylthiobenzene)-1-propanone, 2 -dimethylamino-2-benzyl-(4-morpholinophenyl)-1-butanone; 2,2-diethoxy-1,2-diacetophenone; benzoylformate Ester, diethylene glycol dibenzoylformic acid, ester polybutanediol dibenzoylformate; (2,4,6-trimethylbenzoyl)diphenylphosphine oxide, di(2,4 ,6-trimethylbenzoyl)phenylphosphine oxide; benzophenone and its substituted derivatives such as benzophenone, 4-methylbenzophenone, 4-chlorobenzophenone, 4-benzene Benzophenone, 2'-chloro-4-phenylbenzophenone, 4-methylthiobenzophenone, 4-(2-hydroxyethylthio)benzophenone, 4-hydroxydi Benzophenone laurate Dibenzophenone-4-oxoacetate polyethylene glycol ester; thioxanthone and its substituted derivatives such as 2-isopropylthioxanthone, 2,4-diethylthiaxanone, 1-chloro -4-propoxy thioxanthone, thioxanthone-2-carboxylic acid polyethylene glycol ester, thioxanthone-2-oxyacetic acid polyethylene glycol ester; halogenated methyl triazine such as 2-( 4-methoxyphenyl)-4,6-bis(trichloromethyl)-[1,3,5]-triazine; hexaaryldiimidazoles such as hexa-chlorophenyldiimidazole; ferrocene a compound; a ferrocene compound; a coumarin; camphor; an acridine such as 9-phenyl acridine; an amine such as 4,4'-di(diethylamino)benzophenone, 4-di Ethyl methylaminobenzoate, triethanolamine, methyldiethanolamine or a reactive amine compound such as diethylamine and ethoxylated trimethylolpropane triacrylate adduct; phosphites such as triphenyl phosphite Ester, trilauryl phosphite; chain transfer agents such as hexanedithiol, octyl mercaptan.

Additive (d) contains pigments and dyes, pigments are printing inks and filter preparation The necessary components of the device can be red, green, blue, black, white, yellow, magenta, cyan and other specific special colors according to the needs of use, and the corresponding pigments such as carbon black, indigo blue, titanium dioxide and the like are commercially available varieties. The pigment concentration generally accounts for 10-30% by weight of all solid components of the aforementioned photocurable composition.

The additive (d) may also be a phenolic and hindered amine polymerization inhibitor, such as methoxy a phenol, a nitrosophthalide aluminum complex polymerization inhibitor; a light absorber such as a 2-(2'-hydroxyphenyl)-benzotriazole salicylate, a triazine; a leveling agent For example, vinyl triethoxy decane; wetting agents, dispersing agents, the amount of which is limited to the properties of the photocurable composition, there is no special requirement.

The additive (d) further includes a developable resin in which an alkali-soluble developable resin, For example, a polyacrylate copolymer containing a carboxylic acid side chain, the comonomer may be selected from the group consisting of acrylic acid or methacrylic acid, alkyl acrylate, alkyl methacrylate, styrene, low polystyrene; examples of solvent developable resins There are cellulose esters and cellulose ethers, polyvinyl acetate, polyvinyl butyral, a conventional resin of polystyrene, polycarbonate, polyvinyl chloride, polyester, polyimide; when the developable resin is an alkali-soluble resin, the photocurable composition can be used for photoresist and for display Production of color filters in devices.

The aforementioned photocurable composition composition further contains a thermally dried resin and thermosetting Resin component (e), such as cellulose solution, polyisocyanate, polyimide, they are suitable for the process requirements of photocuring, heat curing segmentation processing.

It is also allowed to add at least one epoxy group in the aforementioned photocurable composition. a compound as a thermosetting component (f) and an epoxy curing accelerator (g); a compound having an epoxy group as the thermosetting component (f) may be a known thermosetting epoxy compound such as an aliphatic epoxy resin or An aromatic epoxy resin, preferably a bisphenol S type epoxy resin such as BPS-200, a bisphenol A type epoxy resin, a novolac epoxy resin, etc., and a partial esterified product thereof, which are relatively in the composition. The component (f) is used in an amount of 30 to 70 parts by weight based on 100 parts by weight of the component (b).

When a thermosetting component (f) is used, an epoxy curing accelerator is optionally used. (g) As a synergistic component, it can play a good curing promotion. Examples are amine accelerators and imidazoles. The accelerators and other commonly used epoxy resin hardeners do not exceed 5% by weight of the thermosetting component (f).

Except for the above components (a), (b), (c), (d), (e), (f), (g), Other additives (h) commonly used in the art may also be used in the photocurable composition, and include one of additives for improving the adhesion and film forming hardness of the photocurable composition, etc., such as sulfuric acid.钡, powdered cerium oxide, talc, calcium carbonate, mica powder, etc., the amount of which is less than 30% of the total weight of the composition;

The aforementioned photocurable composition can also be diluted by a solvent according to the needs of the application field. For later use, suitable solvents are: ketones such as methyl ethyl ketone, cyclohexanone; hydrocarbons such as toluene, xylene, octane, petroleum ether, naphtha; alcohols such as n-butanol, propylene glycol Et al; alcohol ethers and esters thereof, such as propylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, methyl 3-methoxypropionate, etc.; amides such as N, N-two Methylformamide.

The aforementioned photocurable composition or a mixture diluted by the solvent is produced by ink After the method is prepared, it is stored in the dark.

The use of the aforementioned photocurable composition is for the manufacture of colored or transparent One of the following products: coatings, adhesives or inks, photoresists and photoresists, which are used in printing, 3D printing, color filter production in display devices, image reproduction technology, Printed circuit board dielectric layer, electronic device package, optical switch, three-dimensional mold, quartz fiber protective layer, medical products.

The present invention provides a carbon-carbon double bond compound in the aforementioned photocurable composition. The curing method, that is, the photocurable composition is applied onto a substrate to form a coating layer, and the coating layer is cured by irradiation with light of 190 nm to 600 nm. The light comes from the sun, mercury lamp, high-pressure mercury lamp or LED lamp, including the light wave in the range of 190-600nm or the light wave which is controlled by the grating to control the wavelength of the output light. It can also be used between 360nm-410nm. A light source of a predetermined wavelength range, such as a 365 nm LED light source, illuminates the coating layer of the photocurable composition; the LED is defined as a light emitting semiconductor diode.

The photocurable composition has a method of forming a raised pattern by first combining a photocuring composition The material is diluted with a solvent; the diluted photocurable composition is then applied to a substrate, and the unexposed portion is removed by drying, exposure, and development to obtain a raised pattern.

The invention contains at least one asymmetric two having a compound of the formula I A photocurable composition of an oxime ester compound, a photocurable monomer, an alkali-soluble resin, a pigment, and an additive, which can be used as a photoresist, has high light sensitivity, is easily developed by an alkaline aqueous solution, does not swell and deform, and has an excellent imaging effect. Suitable for etching photoresist, solder resist photoresist; for image display and recording materials; inkjet ink cured with LED lamps; also used in the production process of LCD, OLED, PDP It can also be used to form barrier coatings for various electronic components in the manufacture of various printing plates and in the production of electronic circuit boards or integrated circuits.

The aforementioned photocurable composition has excellent resistance to oxygen inhibition and heat treatment Performance, meeting the requirements of color filter production process, especially suitable for the production of liquid crystal displays and organic semiconductor electroluminescent displays.

Using the photocurable composition of the present invention as a photoresist, sequentially coated and exposed The light, development, and heat treatment processes form a black, red, green, and blue three-color pattern to obtain a complete color filter. The substrate of these color filters may be a glass or organic polymer film and a ceramic sheet.

The present invention also includes color filters made using the aforementioned photocurable composition. sheet.

Applying the aforementioned photocurable composition to a flat or curved substrate and drying it a film layer; a non-exposed portion is removed by a mask exposure and development method to obtain a convex image, and a color filter containing black, red, green, and blue color elements is passed through the compound containing the structural formula I of the present invention. A coating, exposure, development, and heat treatment process of a photocurable composition composed of a symmetric diterpene ester compound, a photocurable monomer, an alkali-soluble resin, and a corresponding pigment or auxiliary agent, which also includes a necessary treatment such as cleaning.

Use coating techniques commonly used in the art such as spin coating, roll coating, spray coating, transfer The method further uniformly applies the photocurable composition of the present invention to the substrate to be coated, the coating amount is determined as required, and the usual thickness is 0.1 μm to 1 mm; when the photocurable composition contains the solvent component, the heating method is used. For example, the drying method at 80 ° C causes the solvent to volatilize, and the non-volatile component forms a layer of glue remaining on the substrate.

The next step is exposure. If it is not directly exposed to UV laser, it will have The mask of the image is placed on the glue layer, and the ultraviolet or visible light source emits light of a certain range of wavelengths to set the energy to pass through the transparent portion of the mask for exposure, so that the light receiving portion of the adhesive layer is cured, and the shielded portion does not solidify.

Next is development, removing the unexposed portion to obtain a raised pattern; development process Operating with parameters well known to those skilled in the art, such as spraying at 30 ° C, rinsing; usually using alkaline aqueous development, such as alkali metal hydroxide, aqueous carbonate solution, aqueous ammonia, may also be added to the aqueous solution if necessary a quantitative wetting agent such as a surfactant, an organic solvent such as cyclohexanone, acetone, ethylene glycol ether, etc.; a developing method of immersing the exposure film in a developing bath or spraying the developing solution onto the exposed film is possible, specific The development temperature and time depend on the development effect; the alkali solution used for development is to dissolve the alkaline substance in water or an aqueous solution containing a water-soluble organic solvent, and examples of the alkaline substance are sodium hydroxide, potassium hydroxide, and carbonic acid. Sodium, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, triethanolamine, morpholine, trisodium phosphate, the weight concentration range is 0.1-10%; the above aqueous solution may also be added with a surfactant concentration of 0.05-5% by weight.

The final heat treatment process optimizes image fastness, typically at 200-260 Bake in a °C hot oven for 15-45 minutes.

Based on this, according to the production process of a known color filter, the combination of the present invention is used. The color filter device can be manufactured and exhibits excellent processability, clear array, high light transmittance, and is used for producing high quality displays.

The following examples are illustrative of the invention in more detail, in terms of weight Unless otherwise specified.

Example 1 Synthesis of 5-phenylthioindan-1-one

Weigh 33.3g (0.2mol) of 5-chloro-1-indanone in a 50ml three-necked bottle and add 30 ml of N,N-dimethylformamide (DMF), 30.0 g (0.27 mol) of thiophenol, 36 g of anhydrous potassium carbonate, nitrogen protection, stirring at 40-45 ° C for 6 h; DMF was recovered under reduced pressure, and the residue was added to 100 ml of water Extract twice with 25 ml of 1,2-dichloroethane, combine the 1,2-dichloroethane solution, wash twice with 10 ml of water, filter the paper in a Buchner funnel, filter the organic phase with it, concentrate the filtrate. To the residue, the residue was recrystallized from methanol and dried to yield 43.4 g of pale yellow crystals, yield: 90.3%, HPLC, purity 98.2%, melting range 46.0-48.0 °C.

Example 2 Synthesis of 5-(4-octanoylphenylthio)indan-1-one

The product of Example 1 was weighed to give 5-phenylthioindan-1-one 24.04 g (0.1 mol) dissolved in 120 ml of 1,2-dichloroethane, cooled to 5-10 ° C, and added 28 g (0.21 mol) of anhydrous three. Aluminum chloride, 17.9g (0.11mol) of octanoyl chloride was added dropwise with stirring. After the addition, the mixture was stirred for 4 hours. The reaction solution was treated with dilute hydrochloric acid. The organic solution was separated, washed once, and concentrated to recover 1,2-dichloroethane. The product was recrystallized from 100 ml of ethanol to give white crystals (33.1 g), yield 90.1%, melting range 74.3-75.2 ° C, ¹ H-NMR data indicated that the product was 5-(4-octanoylphenylthio)indan-1 - ketone; ¹ H-NMR (CDCl ₃ ), δ (ppm) value data: 0.8848 (t, 3H, CH ₃ ), 1.2892-1.3412 (m, 8H, 4CH ₂ ), 1.7359 (m, 2H, CH ₂ ) , 2.7066(t,2H,c-CH ₂ ), 2.9526(t,2H,CH ₂ ), 3.0961(t,2H,c-CH ₂ ),7.2740/7.3008(d,1H,ArH), 7.3734(s, 1H, ArH), 7.4525/7.4797 (d, 2H, 2ArH), 7.6677/7.6945 (d, 1H, ArH), 7.9221/7.9493 (d, 2H, 2ArH).

Example 3 Synthesis of 5-(4-octanoylphenylthio)indan-1,2-dione-2-indole

The product obtained in Example 2, 5-(4-octanoylphenylthio)indan-1-one, 18.4 g (0.05 mol) was dissolved in a 250 ml three-necked flask with 150 ml of ethanol, and then added with 36% concentrated hydrochloric acid 2 g, water bath 15 The mixture was stirred at -20 ° C, and 6.2 g (0.06 mol) of n-butyl nitrite was added dropwise in 15 min. After stirring at 25 ° C for 5 h, the reaction solution was cooled to 5-10 ° C, and the precipitated yellow solid was filtered, and 18.7 g after drying, the purity was analyzed. 98.90%, melting range 162.7-164.0 ℃, ¹ H-NMR data show that the product obtained is 5- (4-octanoyl-phenylthio) -1,2-indan-2-oxime, 94.2% yield; ¹ H-NMR (CDCl ₃ ), δ (ppm) value data: 0.8866 (t, 3H, CH ₃ ), 1.2965-1.3512 (m, 8H, 4CH ₂ ), 1.7493 (m, 2H, CH ₂ ), 2.9737 (t , 2H, CH ₂ ), 3.7977 (s, 2H, c-CH ₂ ), 7.2674/7.2943 (d, 1H, ArH), 7.3320 (s, 1H, ArH), 7.5281/7.5558 (d, 2H, 2ArH), 7.7707/7.7977 (d, 1H, 2ArH), 7.9648/7.9925 (d, 2H, 2ArH), 12.4460 (s, 1H, NOH).

Example 4 Synthesis of Ditelluride

The product obtained in Example 2 was obtained as 5-(4-octanoylphenylthio)indan-1,2-dione-2-indole 7.95 g (0.02 mol), dissolved in 40 ml of dimethylhydrazine, and added 36% thick. 0.5g hydrochloric acid, water bath 20-25 ° C heat stirring, adding 3.1g (0.03mol) n-butyl nitrite in 15min, stirring for 10h, the reaction liquid is cooled to 5-10 ° C, the precipitated yellow solid is filtered, after drying 7.72 g, analytical purity 96.80%, yield 90.5%; melting range 171.0-173.0 ° C, ¹ H-NMR data showed that the product obtained is a double telluride, ¹ H-NMR (DMSO-d ₆ ), δ (ppm) value data: 0.850 (t, 3H, CH ₃ ), 1.272-1.492 (m, 8H, 4CH ₂ ), 2.616 (t, 2H, CH ₂ ), 3.738 (s, 2H, c-CH ₂ ), 7.299/7.319 (d, 1H, ArH), 7.435 (s, 1H, ArH), 7.557/7.578 (d, 2H, 2ArH), 7.719/7.739 (d, 1H, 2ArH), 7.847/7.867 (d, 2H, 2ArH), 12.446(s , 1H, NOH), 12.651 (s, 1H, NOH).

Example 5 Synthesis of Diterpene Ester IIA1

4.27 g (0.01 mol) of the product of Example 4 was dissolved in 25 ml of 1,2-dichloroethane, 3.1 g (0.03 mol) of acetic anhydride was added dropwise, and the reaction was carried out for 6 h in a water bath at 20-25 ° C; the reaction solution was washed twice with 25 ml of water. The aqueous phase was separated, and the organic phase was dried over 1.5 g of anhydrous sodium sulfate for 2 h. The desiccant was removed by filtration, and the filtrate was evaporated to dryness under reduced pressure. 15 ml of ethyl acetate was added to the residue, heated to dissolve in total, and 0.05 g of activated carbon was added for reflux for 0.5 h. The activated carbon was separated by filtration, 15 ml of n-hexane was added to the filtrate, cooled and cooled, crystals were precipitated, suction filtered, and the filter cake was vacuum dried to obtain 4.47 g of a yellow crystalline product, content: 98.0%, yield 87.8%; melting range and ¹ H-NMR (CDCl) ₃ ), δ (ppm) value data are shown in Table 1.

Example 6 Synthesis of 5-(4-pentanoylphenylthio)indan-1-one

In the same manner as in Example 2, pentanoyl chloride was used instead of octanoyl chloride to obtain 5-(4-pentanoylphenylthio)indan-1-one, yield 93.0%, melting range 74.1-75.8 ° C, ¹ H-NMR data The product was found to be 5-[4-(3-cyclopentylpropanoyl)phenylthio]indan-1-one; ¹ H-NMR (CDCl ₃ ), δ (ppm) value data: 0.9590 (t, 3H) , CH ₃ ), 1.3533-1.4768 (sextet, 2H, CH ₂ ), 1.7274 (quintet, 2H, CH ₂ ), 2.7047 (t, 2H, c-CH ₂ Ar), 2.9585 (t, 2H, CH ₂ ), 3.0961(t, 2H, c-CH ₂ CO), 7.2745/7.3030 (d, 1H, ArH), 7.3760 (s, 1H, ArH), 7.4513/7.4791 (d, 2H, 2ArH), 7.6683/7.6952 (d, 1H, ArH), 7.9213/7.9490 (d, 2H, 2ArH).

Example 7 Synthesis of 5-(4-pentanoylphenylthio)indan-1,2-dione-2-indole

According to the deuteration reaction method of Example 3, the product of Example 6 was used as a raw material. Dimethyl hydrazine was used as a solvent for the oximation reaction, and HPLC analysis gave a mono-deuterated product without separating the mono-deuterated product.

Example 8 Synthesis of Ditelluride

In the reaction liquid of Example 7, the same weight of n-butyl nitrite was continuously added dropwise to carry out the second deuteration reaction, and after 10 h, the yellow solid was obtained by the method of Example 4, and the purity was 96.50%, wherein the cis isomer content. 3.30%, the content of trans isomer is 93.20%, the yield is 85.0%; ¹ H-NMR data shows that the obtained product is a double telluride, ¹ H-NMR (DMSO-d ₆ ), δ (ppm) value data: 0.9073 ( t, 3H, CH ₃ ), 1.4514-1.5741 (sextet, 2H, CH ₂ ), 2.5879 (t, 2H, CH ₂ ), 3.7380 (s, 2H, c-CH ₂ ), 7.2916/7.3192 (d, 1H, ArH), 7.5172 (s, 1H, ArH), 7.5562/7.5836 (d, 2H, 2ArH), 7.7166/7.7437 (d, 1H, ArH), 7.8505/7.8779 (d, 2H, 2ArH), 12.7769 (s, 1H) , NOH), 12.6661 (s, 1H, NOH).

Example 9 Synthesis of Diterpene Ester IIA6

According to the reaction method of Example 5, the product of Example 8 was used as a raw material, and the esterification reaction was carried out to obtain a yellow solid with a purity of 98.65%, wherein the cis isomer content was 1.25%, and the trans isomer content was 97.40. %, yield 60.3%; ¹ H-NMR data showed that the product obtained was IIA6; ¹ H-NMR (CDCl ₃ ), δ (ppm) value data are shown in Table 1.

Example 10 Synthesis of 5-[4-(3-cyclopentanoyl)phenylthio]indan-1-one

In the same manner as in Example 2, 3-cyclopentylpropionyl chloride was used instead of octanoyl chloride to obtain 5-[4-(3-cyclopentanoyl)phenylthio]indan-1-one in a yield of 92.0%. The procedure of 88.5-90.0 ° C, ¹ H-NMR data indicated that the product was 5-[4-(3-cyclopentylpropionyl)phenylthio]indan-1-one; ¹ H-NMR (CDCl ₃ ), δ (ppm) value data: 1.1072 (m, 2H, CH ₂ ), 1.5328-1.8691 (m, 9H, 4CH ₂ +1CH), 2.7067 (t, 2H, c-CH ₂ ), 2.9689 (t, 2H, CH ₂ ), 3.0974 (t, 2H, c-CH ₂ ), 7.278 / 7.3048 (d, 1H, ArH), 7.3766 (s, 1H, ArH), 7.4531 / 7.4803 (d, 2H, 2ArH), 7.6695/7.7963 (d , 1H, 2ArH), 7.9245/7.9517 (d, 2H, 2ArH).

Example 11 Synthesis of 5-[4-(3-cyclopentylpropionyl)phenylthio]indan-1,2-dione-2-indole

Oximation according to the method of Example 3, to the product of Example 10 as starting material in place of isoamyl nitrite with n-butyl nitrite oximation reaction, the precipitated yellow solid, drying the solvent, a purity of 96%, ¹ H-NMR data indicated that the obtained product was 5-[4-(3-cyclopentylpropanoyl)phenylthio]indan-1,2-dione-2-indole, yield 95.5%; ¹ H-NMR ( DMSO-d ₆ ), δ (ppm) value data: 1.1081 (m, 2H, CH ₂ ), 1.4795-1.7602 (m, 9H, 4CH ₂ ), 3.0258 (t, 2H, CH ₂ ), 3.7342 (s, 2H , c-CH ₂ ), 7.3186/7.3451 (d, 1H, ArH), 7.5243 (s, 1H, ArH), 7.5667/7.5923 (d, 2H, 2ArH), 7.7103/7.7370 (d, 1H, 2ArH), 7.9987 /8.0238 (d, 2H, 2ArH), 12.6665 (s, 1H, NOH).

Example 12 Synthesis of Ditelluride

According to the reaction method of Example 4, the product of Example 11 was used as a raw material, and the second deuteration reaction was carried out by using isoamyl nitrite instead of n-butyl nitrite to obtain a yellow solid with a purity of 95.50%, wherein cis is The isomer content was 5.10%, the trans isomer content was 90.40%, and the yield was 88.3%. The ¹ H-NMR data indicated that the obtained product was a double telluride, ¹ H-NMR (DMSO-d ₆ ), δ (ppm) value. Data: 1.1766-1.6286 (m, 8H, 4CH ₂ ), 2.1325 (heptet, 1H, CH), 2.6489/2.6739 (d, 2H, CH ₂ ), 3.7410 (s, 2H, c-CH ₂ ), 7.2981/7.3249 (d, 1H, ArH), 7.5258/7.5529 (d, 2H, 2ArH), 7.5879 (s, 1H, ArH), 7.7188/7.7459 (d, 1H, 2ArH), 7.8404/7.8680 (d, 2H, 2ArH), 12.4514 (s, 1H, NOH), 12.6649 (s, 1H, NOH).

Example 13 Synthesis of Diterpene Ester IIA3

According to the reaction method of Example 5, the product of Example 12 was used as a raw material, and the esterification reaction was carried out to obtain a yellow solid with a purity of 98.65%, wherein the cis isomer content was 1.50%, and the trans isomer content was 97.15. %, yield 60.3%; ¹ H-NMR data showed that the obtained product was IA3; ¹ H-NMR (CDCl ₃ ), δ (ppm) value data is shown in Table 1.

Example 14 Preparation of alkali soluble resin

180 g of benzyl methacrylate, 60 g of methacrylic acid, and hydroxyethyl methacrylate 60 g of ester, 15 g of azobisisobutyronitrile, 6 g of dodecyl mercaptan and 1000 ml of toluene were mixed and placed in a constant pressure dropping funnel; 1000 ml of toluene was placed in a three-necked flask, and a stirring, constant pressure dropping funnel and thermometer were installed. Turn on the stirring, replace the gas in the flask with nitrogen; heat the flask to bring the solvent temperature to 80-85 ° C, keep warm, start to add the monomer mixed solution, drop about 1 h; continue the reaction for 6 h; cool down naturally, stop stirring, wait for resin to settle. After that, the upper clear solution was taken up, the lower solvent-containing resin was filtered, and the resin cake was rinsed with 500 ml of toluene; the filter cake was dried under reduced pressure to obtain 250 g of a white powdery solid resin; PMA (propylene glycol methyl ether acetate) 1000 g was used. Dissolve in 20% solution for use.

Example 15 Preparation and Development of Photoresist

According to the formula 15A, 15B, 15C (photoinitiator is OXE01), 15D (light) The weight ratio of the initiator is OXE02). All the components are prepared into a photocurable composition according to the preparation method of the ink, and are in a fluid liquid state.

Applying the above liquid composition to the surface of the glass by wire bar method and baking at 80 ° C The solvent PMA was volatilized for 3 minutes, and the residual film thickness was measured to be 2 μm.

A 21-step gray gradient ruler was placed on the film, and a 2000 W high-pressure mercury light line was filtered by a 365 nm grating screening procedure, and the distance between the film and the grating was 10 cm, so that the exposure amount reached 800 mJ/cm ² .

Soak in a 1% sodium carbonate solution bath at 30 ° C for 1 min, record the most visible The larger the film retention order, the larger the number, the stronger the light sensitivity of the measured composition, and the higher the photocuring rate and film forming performance of the photoresist. The results are shown in Table 3.

The development results in Table 3 show that the photoinitiators of Examples 9 and 13 were used. The formulated photocurable composition has a light sensitivity significantly superior to that of the photocurable composition formulated using OXE01 and OXE02, improving the photocuring rate and film forming performance of the photoresist.

Example 16 Photocuring composition gel conversion rate test experiment

Formulations 15A, 15B, 15C, 15D in Table 2 of Example 15 above were applied by wire bar method. The composition was applied to the surface of the glass, baked at 80 ° C for 3 min, and the solvent PMA was volatilized, and the thickness of the remaining film was measured to be 2 μm.

The 2000W high-pressure mercury light line was filtered by a 365 nm grating screening program, and the distance between the film and the grating was 10 cm, so that the exposure amount reached 200,400,600 mJ/cm ² , respectively. After curing, the sample was wrapped with a stainless steel mesh, and the weight W _{1 was} weighed and soaked in acetone for 72 hours. The residual film weight W _{2 was} measured by drying, and W ₁ /W ₂ was gel conversion rate gel%. The results are shown in Table 4.

From Table 4 it can be concluded that in the photoresist formulation, Example 9 and Example 13 The photoinitiator gives a higher degree of double bond polymerization and a significantly higher activity.

Example 17 LED light source curing photosensitive composition and curing efficiency test experiment

The photocurable compositions 15A, 15B, 15C, and 15D in Example 15 were applied to the surface of the glass by a wire bar method, baked at 80 ° C for 3 minutes, and the solvent PMA was volatilized, and the thickness of the remaining film was measured to be 2 μm. Curing was carried out as follows.

Curing device: LEDUV curing device, model: UV-101D (Beijing Iwata Boyuan Technology Co., Ltd.).

Light source: UV-LED point source, diameter: 10 mm; wavelength: 365 nm, maximum illumination: 40 mw/cm ² .

Curing conditions: working distance: 21 mm; irradiation time: 1 s.

The curing efficiency is characterized by: after irradiating with a point light source for 1 s, the whole glass piece is immersed in an acetone solution for 5 s, and after taking out, the cured film pattern diameter is measured. The larger the value, the higher the brightness and the higher the curing efficiency, Table 5 For the measurement results, it can be seen from the measurement results in Table 5 that when the photosensitive composition for curing the solder resist ink or the photoresist is cured by the LED light source, the photosensitive composition provided by the present invention is compared with the existing ones using OXE01 and OXE02. The composition of the photoinitiator has a higher Light sensitivity.

Example 18 Printing Ink Formulation and High Pressure Mercury Lamp Curing

Formula composition ratio: epoxy resin acrylate prepolymer (Changxing Chemical 621-100) 50 parts, polyester acrylate prepolymer (Changxing Chemical 6311-10) 10 parts, TPGDA (Changxing Chemical EM223) 30 parts, carbon black (Degussa P25) 4 parts, photoinitiator 6 parts; mixing Grinding to a fineness of 2 um or less, ink samples 18A-18D were obtained; screen printing onto a aluminum plate with a 420 mesh, curing under a high pressure mercury lamp, and gel conversion rate gel% was measured according to the method of Example 16, and Table 6 is a measurement result. It can be seen from the measurement results in Table 6 that the gel conversion rate of the compound of the present invention was significantly higher than that of the control compound by irradiation with a high pressure mercury lamp.

Example 19 Printing Ink Formulation and LED Surface Light Curing

Formulation ratio: 50 parts of epoxy acrylate prepolymer, 10 parts of polyester acrylate prepolymer, 30 parts of TPGDA, 4 parts of yellow 3G (BASF), 6 parts of photoinitiator; mixed grinding to fineness 2um The ink samples 19A-19D were obtained and applied to a glass plate; cured with a 365 nm LED surface light source, and the exposure amount was 86 mJ/cm ² ; the gel conversion rate gel% was measured according to the method of Example 16, and the measurement results are shown in Table 7, from Table 7 It can be seen from the measurement results that the gel conversion rate of the compound of the present invention is significantly higher than that of the control compound by irradiation with a 365 nm LED light source.

Example 20 Filter Film Prepared with Photoresist Ink and Exposure Developed

Formulation composition: 500 parts of alkali-soluble resin solution (Example 14), dipentaerythritol 100 parts of hexaacrylate (Cytec DPHA), 100 parts of photoinitiator, co-initiator BCIM (2,2'-di-o-chlorophenyl-4,4',5,5'-tetraphenylbiimidazole) 20 parts, 500 parts of carbon black (Degussa P25) dispersion (containing 20% carbon black), uniformly polished according to the ink preparation method, according to the different photoinitiators used, there are five kinds of inks of 20A-20E.

They were coated separately, dried under reduced pressure, 1 μm thick, covered with a pattern mask, exposed with a 365 nm LED surface light source, exposed at 100 mJ/cm ² , developed with an aqueous solution containing 1% NaOH and 2% acetone for 30 seconds, and examined by stereoscopic electron microscopy. Pattern morphology and fastness, morphology and fastness observation and evaluation: 1. The exposed part is intact without falling off; 2. The exposed part has no peeling and curling; 3. The exposed part is not edged; 4. The exposed part is incomplete; 5. The exposed part Has fallen off.

The evaluation of the experimental results is shown in Table 8. From the results of Table 8, it can be seen that the present invention is included. After the ink of the composite was exposed and developed, the edges of the pattern were clear and tidy, and the film was not peeled off, and the performance of the compound of the present invention was significantly better than that of the control compound.

Table 8 Black photoresist ink exposure evaluation

Example 21 Filter Film Prepared with Photoresist Ink and Exposure Developed

Formulation composition: 500 parts of alkali-soluble resin solution (Example 14), dipentaerythritol 100 parts of hexaacrylate (Cytec), 100 parts of photoinitiator, and 100 parts of red pigment L3920 (BASF) were uniformly ground by the ink preparation method to obtain five inks of 21A-21E.

Coating, drying under reduced pressure, thickness 2 μm, covered with a pattern mask, exposed with a 365 nm LED surface light source, exposure amount 86 mJ/cm ² , developed with an aqueous solution containing 1% NaOH and 2% acetone for 30S, and detected by a stereoscopic microscope The fastness and morphology were evaluated in the same manner as in Example 20; the evaluation of the experimental results is shown in Table 9. From the results of Table 9, it can be seen that the ink containing the compound of the present invention has a clear and tidy edge after exposure and development, and is firm and non-shedding, and the properties of the compound of the present invention. The performance was significantly better than the control compound.

Example 22 Filter Film Prepared with Photoresist Ink and Exposure Developed

Formulation composition: 500 parts of alkali-soluble resin solution (Example 14), 100 parts of dipentaerythritol hexaacrylate (Cytec), 10 parts of photoinitiator, 100 parts of red pigment L3920 (BASF company); Five inks of 22A-22E were obtained.

Coating, drying under reduced pressure, 2 μm thick, covered with a pattern mask, exposed with a 365 nm LED surface light source, exposure amount 86 mJ/cm ² , developed with an aqueous solution containing 1% NaOH and 2% acetone for 30S, and detected by stereoscopic microscope The fastness and morphology were evaluated in the same manner as in Example 20. The evaluation of the experimental results is shown in Table 10. From the results of Table 10, it can be seen that the ink containing the compound of the present invention has a clear and tidy edge after exposure and development, and is firm and non-shedding, and the properties of the compound of the present invention. The performance was significantly better than the control compound.

Claims (28)

An asymmetric diterpene ester compound comprising the following structural formula I: Wherein the Ar _{1 is} selected from a C ₆ -C ₂₀ o-arylene or a C ₃ -C ₂₀ o-heteroaryl group substituted by the X ₁ , the C ₆ -C ₂₀ o-arylene group or the C ₃ - The C ₂₀ ortho-heteroaryl group is bonded to the Y ₁ and a carbonyl group by two adjacent atoms to form a ring structure, and the substituents on the remaining atoms are each selected from the group consisting of a hydrogen atom, a halogen atom, and C _{1 .} -C ₁₂ alkyl, C ₅ -C ₇ cycloalkyl, C ₁ -C ₄ alkyl substituted by C ₅ -C ₇ cycloalkyl, C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ alkyl Benzyloxy, C ₁ -C ₃ alkylenedioxy, R ₂ C(O)O, C ₁ -C ₁₂ alkylthio, C ₁ -C ₄ alkylphenylthio, CN, carboxyl, C ₁ -C ₁₂ alkoxycarbonyl group, an arylcarbonyl group, heteroarylcarbonyl _{group, X 3 R 18, C 1} -C 4 alkyl group, C1-C8 alkyl group a phenoxy group, C ₅ -C ₆ cycloalkyl Alkyl acyl phenoxy, C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy, aryl acyl phenoxy, heteroaryl acyl phenoxy, R ₂ C(O) O-substituted C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylphenylthio group, C ₁ -C ₈ alkyl acyl phenylthio group, C ₅ -C ₆ cycloalkyl phenyl phenylthio group, C _5- C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl a phenylthio group, an aryl acyl phenylthio group, a heteroaryl acyl phenylthio group; one or more C ₁ -C ₁₂ alkoxy groups, a C ₁ -C ₄ alkylbenzyloxy group, a R ₂ C(O) group O-substituted C ₁ -C ₄ alkoxy; phenyl and optionally by one or more C ₁ -C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl acyl, aryl acyl, heteroaryl acyl, X ₃ R ₁₇ , phenyl, a halogen atom, a CN-substituted phenyl group; and a glycidyl group, wherein the epoxy group is optionally condensed with a C ₁ -C ₄ alkyl aldehyde, a ketone; the X _{3 is} selected from the group consisting of O, S and NR _22; the Ar ₂ is selected from: X ₁ C through which the connecting Ar _{1 6} -C ₂₀ arylene group, X ₁ and through which the C ₃ -C ₂₀ heteroarylene group that is connected to Ar _1; The n is 0 or 1; the X ₁ is selected from the group consisting of O, S, NR ₁₈ and Y ₂ -Z ₁ -Y ₂ ; the Y ₁ is selected from the group consisting of: (CH _{2 m} CR ₁₅ R ₁₆ , NR ₁₉ , O(CR ₁₅ R ₁₆ ) _m , S(CR ₁₅ R ₁₆ ) _m , (CR ₁₅ R ₁₆ ) _m C=O and S=O, the m is 0 or 1; The Z ₁ is selected from the group consisting of C ₁ -C ₁₀ linear alkylene, C ₁ -C ₁₀ branched alkylene, C attached to the terminal group by one or more oxygen or sulfur atoms. ₁ -C ₁₀ linear alkylene, One or more oxygen atom or sulfur atom attached to the end groups C ₁ -C ₁₀ branched alkylene, substituted by one or more oxygen atoms or sulfur atom inserted straight chain C ₂ -C ₁₀ alkylene group, is one or more oxygen atom or sulfur atom inserted branched C ₂ -C ₁₀ alkylene group unsubstituted C ₆ -C ₂₀ arylene group, and an optionally substituted C ₆ -C ₂₀ arylene; The Y ₂ is selected from the group consisting of O, S, NR ₁₈ and OC(O); the R ₁ is selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a diphenyl group. phosphono, di (C ₁ -C ₄ alkoxy) phosphono group; optionally substituted with one or more C ₃ -C ₇ cycloalkyl, phenyl, oR _20, SR _21, NR ₂₂ R ₂₃ is substituted C ₂ -C ₁₈ alkyl, wherein the phenyl group is substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C _1- C ₄ alkanoyloxy, aroyloxy substituted; C ₂ -C ₁₈ alkyl group inserted by C ₃ -C ₇ cycloalkylene, phenylene, O, S, NR ₂₂ ; C ₃ - C ₈ cycloalkyl, CN, NO _2, phenyl; optionally one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl Phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted phenyl; C ₁ -C ₁₂ alkyl group, C ₁ -C ₁₂ alkoxycarbonyl, wherein alkyl Anyly substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₃ R ₂₀ ; C ₁ -C ₁₂ alkyl An acyl group, a C ₁ -C ₁₂ alkoxycarbonyl group, wherein the alkyl group is optionally interrupted by one or more phenylene groups, X ₃ ; the phenyl group unsubstituted benzoyl group, phenoxycarbonyl group; a benzoyl group or a phenoxycarbonyl group substituted with one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₂ R ₂₀ ; The R ₂ and the R ₃ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₁ -C ₁₈ alkoxy group, a C ₂ -C ₁₈ alkenyl group, a phenyl group, Naphthyl, C ₅ -C ₇ cycloalkyl; optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy, substituted C ₂ -C ₁₈ alkenyl group; a C ₅ -C ₇ cycloalkylene, phenylene O, S, NR ₁₇ inserted C ₂ -C ₁₈ alkenyl; optionally substituted with one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl , heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy, and is substituted with C ₅ -C ₇ cycloalkylene, phenylene, O, S, NR ₁₇ C ₂ inserted -C ₁₈ alkenyl; optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C a C ₂ -C ₁₈ alkyl group substituted with a ₄ alkanoyloxy group or an aroyloxy group; C ₅ -C ₇ optionally substituted by one or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, and CN Cycloalkyl; phenyl unsubstituted benzoyl, phenoxycarbonyl; phenyl substituted by one or more halogen atoms R ₁₇ , C ₅ cycloalkyl, C ₆ cycloalkyl, CN, OH, XR ₁₇ Substituted benzoyl, phenoxycarbonyl; phenyl or naphthyl; optionally substituted by one or more C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, phenyl, halogen atom, CN a phenyl group; a naphthyl group optionally substituted by one or more C ₁ -C ₄ alkyl groups, a C ₁ -C ₄ alkoxy group, a phenyl group, a halogen atom, or a CN; ₁₅ and R ₁₆ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₁ -C ₅ alkyl group substituted by a carboxyl group, and a C ₁ -C ₄ alkoxy group. C ₁ -C ₅ alkyl, C ₂ -C ₄ alkyl substituted by R ₂ C(O)O, C ₅ -C ₇ cycloalkyl, phenyl; optionally substituted by one or more halogen atoms, C ₁ -C ₄ -alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted C ₂ -C ₁₈ alkyl; C ₂ -C ₁₈ alkyl group inserted by C ₅ -C ₇ cycloalkylene, phenylene, O, S, NR ₁₇ ; optionally by one or more C ₁ -C ₄ alkyl groups, Phenyl group, halogen atom, C ₅ -C ₇ cycloalkyl group substituted by CN; optionally substituted by one or more C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy group, carboxyl group, C ₁ -C ₁₂ alkane a acyl group, a C ₅ -C ₆ cycloalkyl formyl group, a C ₅ -C ₆ cycloalkyl group substituted C ₂ -C ₄ alkyl acyl group, a benzoyl group, an XR ₁₇ group, a halogen atom, a phenyl group substituted by CN; The R ₁₇ is a C ₁ -C ₄ alkyl group; the R ₁₈ and the R ₁₉ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₁ -C ₄ alkoxy group. Acyl substitution C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; optionally substituted with one or more halogen atoms, C ₁ - C ₁ -C ₁₈ substituted by C ₄ alkyl, C ₃ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy An alkyl group; optionally a C ₂ -C ₁₈ alkyl group inserted by one or more C ₃ -C ₇ cycloalkylene groups, phenylene groups, O, S, NR ₁₇ ; optionally by one or more C ₁ -C _{a 4-} alkyl group, a phenyl group, a halogen atom, a C ₅ -C ₇ cycloalkyl group substituted by CN; and optionally one or more C ₁ -C ₄ alkyl groups, a carboxyl group, a C ₁ -C ₁₂ alkyl group, C a ₅ -C ₆ cycloalkyl group, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl group, aryl group, XR _17, a phenyl group, a halogen atom, CN substituted phenyl; The R ₂₀ , the R ₂₁ , the R ₂₂ and the R ₂₃ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₃ -C ₇ cycloalkyl group; a C ₁ -C ₁₈ alkyl group substituted by a C ₁ -C ₄ alkoxy group; a C ₂ -C ₁₈ inserted by one or more oxygen atoms, a C ₅ -C ₇ cycloalkylene group, or a phenylene group; alkyl; Phenyl, C ₃ -C ₇ cycloalkyl substituted C ₁ -C ₃ alkyl group; a phenyl group, a naphthyl group, a benzoyl group; and optionally substituted by halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ Alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio, NR ₂₄ R ₂₅ , C ₁ -C ₁₂ alkyl acyl, phenyl substituted by benzoyl, naphthyl, benzoyl An acyl group; the R ₂₄ and the R ₂₅ are each a C ₁ -C ₄ alkyl group; or the NR ₂₄ R ₂₅ is a morpholine, piperidine, piperazine, N-methylpiperazine, pyrrole. The asymmetric diterpene ester compound according to claim 1, wherein the compound of the formula I is further a compound of the following formula II, IIIA or IIIB: Wherein R ₄ , the R ₅ , the R ₆ , the R ₇ , the R ₈ , the R ₉ , the R ₁₀ , the R ₁₁ , the R ₁₂ , the R ₁₃ , and the R ₁₄ are each independently from the following The group formed is selected as: a hydrogen atom, a halogen atom, a C ₁ -C ₁₂ alkyl group, a C ₅ -C ₇ cycloalkyl group, a C ₅ -C ₇ cycloalkyl group substituted C ₁ -C ₄ alkyl group, C ₁ -C ₁₂ alkoxy, phenyl, C ₁ -C ₄ alkylbenzyloxy; optionally substituted by one or more C ₁ -C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl acyl, aryl acyl , heteroaryl acyl, X ₃ R ₁₇ , phenyl, halogen atom, CN substituted phenyl; one or more C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ alkylbenzyloxy, R ₂ C(O)O substituted C ₁ -C ₄ alkoxy, R ₂ C(O)O, CN, carboxyl, C ₁ -C ₁₂ alkoxycarbonyl, arylcarbonyl, heteroarylcarbonyl, X ₃ R ₁₈ ; C ₁ -C ₄ alkylphenoxy, C ₁ -C ₄ alkylphenylthio, C ₁ -C ₈ alkyl acyl phenoxy, aryl acyl phenoxy, heteroaryl acyl phenoxy , C ₅ -C ₆ cycloalkyl acyl phenoxy, C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy, C ₁ -C ₃ alkylenedioxy, C ₁ -C ₁₂ alkyl group, R ₂ C (O) O-substituted C ₁ -C ₄ alkylthio, R ₂ C (O) O-substituted C ₁ -C ₄ alkyl thio, C ₁ -C ₈ alkyl phenylthio group, phenylthio group aryl, heteroaryl, Aryl acyl phenylthio, C ₅ -C ₆ cycloalkyl phenyl phenylthio substituted C ₁ -C ₄ alkyl phenyl thio, C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl An acyl phenylthio group; and a glycidyl group, wherein the epoxy group is arbitrarily condensed with a C ₁ -C ₄ alkyl aldehyde, a ketone; X ₁ is selected from the group consisting of O, S and NR ₁₈ ; X ₂ Selected from the following group: O, S, and NR ₁₉ ; Y ₁ is selected from the group consisting of O, S, and CR ₁₅ R ₁₆ . The asymmetric diterpene ester compound according to claim 2, wherein in the compound of the formula II, the R ₄ , the R ₅ , the R ₆ , the R ₇ , the R ₈ , the R ₉ , the R ₁₀ Is a hydrogen atom; the X _{1 is} selected from O and S; the Y _{1 is} selected from the group consisting of CH ₂ , CHCH ₃ and C(CH ₃ ) ₂ ; n=1; the R _{1 is} selected from the following a group consisting of: C ₁ -C ₁₂ alkyl; and any C ₁ -C ₁₂ alkane substituted by one or more C ₃ -C ₇ cycloalkyl, phenyl, OR ₂₀ , SR ₂₁ , NR ₂₂ R ₂₃ The R ₂ and the R ₃ are each independently methyl, ethyl, phenyl, 2-methylphenyl, 3-methylphenyl, 2,4,6-trimethylphenyl and 2, 6-Dimethoxyphenyl. The asymmetric diterpene ester compound according to claim 2, wherein in the compound of the formula IIIA and IIIB, the X ₂ is NR _{19; and} the Y _{1 is} selected from the group consisting of O, S and CR ₁₅ R _16; the R _11, the R _12, the R _13, the R ₁₄ are each independently selected for the group consisting of the following: a halogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylbenzyloxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylphenoxy and C ₁ -C ₄ alkylphenylthio. The requested item asymmetric two oxime ester compound of claim 4, wherein the compound of structural formula ⅢB ⅢA and in which: Y ₁ is selected from the group consisting of: CH ₂ and CHCH _3; n = 0; R ₁ ' selected from the group consisting of: C ₁ -C ₁₂ alkyl; and optionally substituted with one C ₃ -C ₇ cycloalkyl, _{phenyl, OR 20, SR 21, NR} 22 R 23 substituted C ₁ -C ₁₂ An alkyl group; the R ₂ and the R ₃ are each independently selected from the group consisting of methyl, ethyl, phenyl, 2-methylphenyl, 3-methylphenyl, 2, 4, 6 a trimethylphenyl group and a 2,6-dimethoxyphenyl group; the R ₁₁ , the R ₁₂ , the R ₁₃ and the R ₁₄ are each independently selected from the group consisting of hydrogen atoms and C ₁ -C ₄ alkoxy; the R _{19 is} selected from the group consisting of C ₁ -C ₁₂ alkyl; and C ₁ -C ₃ alkyl substituted by C ₃ -C ₇ cycloalkyl, phenyl. According to the asymmetric diterpene ester compound described in claim 1, the structure is further one of the following: The asymmetric diterpene ester compound according to claim 1, wherein when the Ar ₂ is bonded to the Ar ₁ through the X ₁ , the Ar ₂ carbon atom ortho to the X ₁ is a direct bond or a carbon One of the atoms, a carbonyl group, O, S, and NR ₁₈ is bonded to the Ar ₁ to form a cyclic structure. The asymmetric diterpene ester compound according to claim 1 or 7, wherein the R ₁₅ and the R ₁₆ together with the carbon atom to which they are attached constitute a cyclic group and the number of atoms to be ring-formed is 4-7. The asymmetric diterpene ester compound according to claim 1 or 7, wherein the R ₁₅ and the R ₁₆ each form a cyclic ring together with an adjacent substituent and the number of atoms in the ring is 4-7. The asymmetric diterpene ester compound according to claim 1 or 7, wherein the R ₁₈ is bonded to an aromatic ring in one of the Ar ₁ or the Ar ₂ through a straight bond, a carbon atom or a carbonyl group to form a new ring. The asymmetric diterpene ester compound according to claim 7, wherein the R ₁₈ is bonded to an aromatic ring in one of the Ar ₁ or the Ar ₂ through a straight bond, a carbon atom or a carbonyl group to form a new ring. The asymmetric diterpene ester compound according to claim 8, wherein the R ₁₈ is bonded to an aromatic ring in one of the Ar ₁ or the Ar ₂ through a straight bond, a carbon atom or a carbonyl group to form a new ring. The asymmetric diterpene ester compound according to claim 9, wherein the R ₁₈ is bonded to an aromatic ring in one of the Ar ₁ or the Ar ₂ through a straight bond, a carbon atom or a carbonyl group to form a new ring. A process for producing the asymmetric diterpene ester compound of claim 1 or 6, comprising the steps of: (1) Step 1: Selectively fluorene the ortho-methylene group of the cyclopentanone carbonyl group in the following compound of the formula IV; The method of deuteration is to carry out the oximation reaction of the compound of the formula IV and the alkyl nitrite in an acidic solution to obtain a ketone oxime compound as a compound of the formula V; (IV) (V) (2) Step 2: The compound of the formula V is further subjected to a second deuteration, and the second deuteration method is one of the following: Method A: the structural formula V The compound and the alkyl nitrite are deuterated in an acidic solution to obtain a corresponding second deuterated intermediate structure of the compound of the formula VI; Method B: the compound of the formula V is subjected to a side chain R in the hydroxylamine solution. ₁ oximation of the carbonyl group in CH ₂ CO to obtain the corresponding second deuterated intermediate structure of the compound of formula VII; (3) Step 3: The second deuterated intermediate VI or VII compound is one of the following acylating reagents: Or an esterification reaction of its equivalent acylating reagent gives a compound of the formula I. An asymmetric diketone compound, as shown in Structural Formula IV: Wherein the Ar _{1 is} selected from a C ₆ -C ₂₀ o-arylene or a C ₃ -C ₂₀ o-heteroaryl group substituted by the X ₁ , the C ₆ -C ₂₀ o-arylene group or the C ₃ - The C ₂₀ ortho-heteroaryl group is bonded to the Y ₁ and a carbonyl group by two adjacent atoms to form a ring structure, and the substituents on the remaining atoms are each selected from the group consisting of a hydrogen atom, a halogen atom, and C _{1 .} -C ₁₂ alkyl, C ₅ -C ₇ cycloalkyl, C ₁ -C ₄ alkyl substituted by C ₅ -C ₇ cycloalkyl, C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ alkyl Benzyloxy, C ₁ -C ₃ alkylenedioxy, R ₂ C(O)O, C ₁ -C ₁₂ alkylthio, C ₁ -C ₄ alkylphenylthio, CN, carboxyl, C ₁ -C ₁₂ alkoxycarbonyl group, an arylcarbonyl group, heteroarylcarbonyl _{group, X 3 R 18, C 1} -C 4 alkyl group, C1-C8 alkyl group a phenoxy group, C ₅ -C ₆ cycloalkyl Alkyl acyl phenoxy, C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy, aryl acyl phenoxy, heteroaryl acyl phenoxy, R ₂ C(O) O-substituted C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylphenylthio group, C ₁ -C ₈ alkyl acyl phenylthio group, C ₅ -C ₆ cycloalkyl phenyl phenylthio group, C _5- C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl a phenylthio group, an aryl acyl phenylthio group, a heteroaryl acyl phenylthio group; one or more C ₁ -C ₁₂ alkoxy groups, a C ₁ -C ₄ alkylbenzyloxy group, a R ₂ C(O) group O-substituted C ₁ -C ₄ alkoxy; phenyl and optionally by one or more C ₁ -C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl acyl, aryl acyl, heteroaryl acyl, X ₃ R ₁₇ , phenyl, halogen atom, CN substituted phenyl; epoxy propyl group, wherein the epoxy group arbitrarily homogenizes a C ₁ -C ₄ alkyl aldehyde, a ketone condensation; the X _{3 is} selected from O, S and NR _22; the Ar ₂ is selected from: by the X ₁ C ₁ is connected to the Ar ₆ -C ₂₀ arylene group, through which X ₁ C ₃ -C ₂₀ heteroarylene group is connected to the Ar _1; and the X ₁ is selected from the group consisting of O, S, NR ₁₈ and Y ₂ -Z ₁ -Y ₂ ; the Y1 is selected from the group consisting of: (CH ₂ ) _m CR ₁₅ R ₁₆ , NR ₁₉ , O(CR ₁₅ R ₁₆ ) _m , S(CR ₁₅ R ₁₆ ) _m , (CR ₁₅ R ₁₆ ) _m C=O and S=O, the m is 0 or 1; the Z _{1 is} composed of the following group group elected: C ₁ -C ₁₀ linear alkylene, C ₁ -C ₁₀ branched alkylene, substituted by one or more oxygen atom or sulfur atom attached to the end groups C ₁ -C ₁₀ linear alkylene One or more C atom or sulfur atom attached to a terminal end ₁ -C ₁₀ branched alkylene, substituted by one or more oxygen atoms or sulfur atom inserted straight chain C ₂ -C ₁₀ alkylene group, substituted with one or more oxygen or sulfur atom inserted branched C ₂ -C ₁₀ alkylene group unsubstituted C ₆ -C ₂₀ arylene group, and an optionally substituted C ₆ -C ₂₀ arylene; Y ₂ of the following The group formed is selected from: O, S, NR ₁₈ and OC(O); the R ₁ is selected from the group consisting of hydrogen atom, C ₁ -C ₁₈ alkyl group, diphenylphosphonyl group, C ₁ -C ₄ alkoxy)phosphono; C ₂ -C ₁₈ alkyl optionally substituted by one or more C ₃ -C ₇ cycloalkyl, phenyl, OR ₂₀ , SR ₂₁ , NR ₂₂ R ₂₃ Wherein the phenyl group is any one or more of halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkane Acyloxy, aroyloxy substituted; C ₂ -C ₁₈ alkyl group inserted by C ₃ -C ₇ cycloalkylene, phenylene, O, S, NR ₂₂ ; C ₃ -C ₈ cycloalkyl , CN, NO _2, phenyl; optionally one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl , CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted phenyl; C ₁ -C ₁₂ alkyl group, C ₁ -C ₁₂ alkoxycarbonyl, wherein the alkyl group optionally substituted with one or more Halogen atom, C ₁ -C ₄ alkyl group, C ₅ cycloalkyl group, C ₆ cycloalkyl group, phenyl group, CN, OH, X ₃ R ₂₀ substituted; C ₁ -C ₁₂ alkyl acyl group, C ₁ -C _{a 12} alkoxycarbonyl group, wherein the alkyl group is optionally interrupted by one or more phenylene groups, X ₃ ; the phenyl group unsubstituted benzoyl group, phenoxycarbonyl group; the phenyl group is optionally one or more halogen atoms, a benzoyl group or a phenoxycarbonyl group substituted with C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₂ R ₂₀ ; the R ₁₅ , the R ₁₆ are each independently selected from the group consisting of the following: a hydrogen atom, C ₁ -C ₁₈ alkyl, carboxy substituted C ₁ -C ₅ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ - C ₅ -alkyl, R ₂ C(O)O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkane C, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted C ₂ -C ₁₈ alkyl; C ₂ -C ₁₈ alkyl group inserted by C ₅ -C ₇ cycloalkylene, phenylene, O, S, NR ₁₇ ; optionally by one or more C ₁ -C ₄ An alkyl group, a phenyl group, a halogen atom, a C ₅ -C ₇ cycloalkyl group substituted by CN; optionally substituted by one or more C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy group, carboxyl group, C ₁ - C ₁₂ alkyl acyl, C ₅ -C ₆ cycloalkyl formyl, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl acyl, benzoyl, XR ₁₇ , halogen atom, CN substituted a phenyl group; the R ₁₇ is a C ₁ -C ₄ alkyl group; the R ₁₈ and the R ₁₀ are each independently selected from the group consisting of: a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₁ -C ₄ group; alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; optionally substituted with one or more Halogen atom, C ₁ -C ₄ alkyl group, C ₃ -C ₇ cycloalkyl group, heterocycloalkyl group, phenyl group, heteroaryl group, CN, C ₁ -C ₄ alkanoyloxy group, aroyloxy group substituted C ₁ -C ₁₈ alkyl; optionally substituted with one or more C ₃ -C ₇ cycloalkylene, phenylene, O, S, NR ₁₇ inserted C ₂ -C ₁₈ alkyl; optionally substituted with one or more C ₁ -C ₄ alkyl A phenyl group, a halogen atom, CN substituted C ₅ -C ₇ cycloalkyl; and optionally substituted with one or more C ₁ -C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl group, C ₅ -C ₆ cycloalkyl, formyl, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl group, aryl group, XR _17, a phenyl group, a halogen atom, CN substituted phenyl; the R _20, The R ₂₁ , the R ₂₂ and the R ₂₃ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, a C ₃ -C ₇ cycloalkyl group; a halogen, CN, C ₁ a C ₁ -C ₁₈ alkyl group substituted with a C ₄ alkoxy group; a C ₂ -C ₁₈ alkyl group inserted by one or more oxygen atoms, a C ₅ -C ₇ cycloalkylene group, a phenylene group; C ₁ -C ₃ alkyl substituted by phenyl, C ₃ -C ₇ cycloalkyl; phenyl, naphthyl, benzoyl; and optionally halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ Alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio, NR ₂₄ R ₂₅ , C ₁ -C ₁₂ alkyl acyl, phenyl substituted by benzoyl, naphthyl, benzoyl An acyl group; the R ₂₄ and the R ₂₅ are each a C ₁ -C ₄ alkyl group; or the NR ₂₄ R ₂₅ is a morpholine, piperidine, piperazine, N-methylpiperazine, pyrrole . A ketoxime compound, such as a compound of formula V: Wherein the Ar _{1 is} selected from a C ₆ -C ₂₀ o-arylene or a C ₃ -C ₂₀ o-heteroaryl group substituted by the X ₁ , the C ₆ -C ₂₀ o-arylene group or the C ₃ - The C ₂₀ ortho-heteroaryl group is bonded to the Y ₁ and a carbonyl group by two adjacent atoms to form a ring structure, and the substituents on the remaining atoms are each selected from the group consisting of a hydrogen atom, a halogen atom, and C _{1 .} -C ₁₂ alkyl, C ₅ -C ₇ cycloalkyl, C ₁ -C ₄ alkyl substituted by C ₅ -C ₇ cycloalkyl, C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ alkyl Benzyloxy, C ₁ -C ₃ alkylenedioxy, R ₂ C(O)O, C ₁ -C ₁₂ alkylthio, C ₁ -C ₄ alkylphenylthio, CN, carboxyl, C ₁ -C ₁₂ alkoxycarbonyl group, an arylcarbonyl group, heteroarylcarbonyl _{group, X 3 R 18, C 1} -C 4 alkyl group, C1-C8 alkyl group a phenoxy group, C ₅ -C ₆ cycloalkyl Alkyl acyl phenoxy, C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy, aryl acyl phenoxy, heteroaryl acyl phenoxy, R ₂ C(O) O-substituted C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylphenylthio group, C ₁ -C ₈ alkyl acyl phenylthio group, C ₅ -C ₆ cycloalkyl phenyl phenylthio group, C _5- C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl a phenylthio group, an aryl acyl phenylthio group, a heteroaryl acyl phenylthio group; one or more C ₁ -C ₁₂ alkoxy groups, a C ₁ -C ₄ alkylbenzyloxy group, a R ₂ C(O) group O-substituted C ₁ -C ₄ alkoxy; phenyl and optionally by one or more C ₁ -C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl acyl, aryl acyl, heteroaryl acyl, X ₃ R ₁₇ , a phenyl group, a halogen atom, a CN-substituted phenyl group; a glycidyl group in which an epoxy group is optionally condensed with a C ₁ -C ₄ alkyl aldehyde, a ketone; the X _{3 is} selected from the group consisting of the following group O, S and NR _22; Ar ₂ is selected from the group consisting of: X ₁ C ₁ through which is connected to the Ar is ₆ -C ₂₀ arylene group, ₁₁ connected to the Ar through the X C ₃ -C ₂₀ heteroarylene; the X ₁ is selected from the group consisting of O, S, NR ₁₈ and Y ₂ -Z ₁ -Y ₂ ; the Y1 is selected from the group consisting of: (CH ₂ ) _m CR ₁₅ R ₁₆ , NR ₁₉ , O(CR ₁₅ R ₁₆ ) _m , S(CR ₁₅ R ₁₆ ) _m , (CR ₁₅ R ₁₆ ) _m C=O and S=O, the m is 0 Or 1; the Z ₁ is selected from the group consisting of C ₁ -C ₁₀ linear alkylene, C ₁ -C ₁₀ branched alkylene, attached to one or more oxygen or sulfur atoms base C ₁ -C ₁₀ straight chain alkylene substituted by one or more oxygen atom or sulfur atom attached to the end groups C ₁ -C ₁₀ branched alkylene, substituted by one or more oxygen atoms or sulfur atom inserted a C ₂ -C ₁₀ linear alkylene group, a C ₂ -C ₁₀ branched alkylene group inserted by one or more oxygen atoms or sulfur atoms, an unsubstituted C ₆ -C ₂₀ arylene group, and a C ₆ -C ₂₀ arylene group of a substituent; the Y ₂ is selected from the group consisting of O, S, NR ₁₈ and OC(O); the R ₁ is selected from the group consisting of: a hydrogen atom , C ₁ -C ₁₈ alkyl, diphenylphosphonyl, bis(C ₁ -C ₄ alkoxy)phosphonyl; optionally substituted by one or more C ₃ -C ₇ cycloalkyl, phenyl, OR ₂₀ , a C ₂ -C ₁₈ alkyl group substituted by SR ₂₁ , NR ₂₂ R ₂₃ wherein the phenyl group is any one or more of a halogen atom, a C ₁ -C ₄ alkyl group, a C ₅ -C ₇ cycloalkyl group, a heterocycloalkane Substituent, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted; inserted by C ₃ -C ₇ cycloalkylene, phenylene, O, S, NR ₂₂ C ₂ -C ₁₈ alkyl; C ₃ -C ₈ cycloalkyl, CN, NO ₂ , phenyl; by any one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted phenyl; C ₁ -C ₁₂ alkyl acyl, C ₁ -C ₁₂ alkoxycarbonyl, wherein the alkyl group is optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₃ Substituted by R ₂₀ ; C ₁ -C ₁₂ alkyl acyl, C ₁ -C ₁₂ alkoxycarbonyl, wherein alkyl is optionally substituted with one or more phenylene groups, X ₃ ; phenyl unsubstituted benzoyl An acyl group, a phenoxycarbonyl group; a phenyl group by any one or more of a halogen atom, a C ₁ -C ₄ alkyl group, a C ₅ cycloalkyl group, a C ₆ cycloalkyl group, a phenyl group, a CN, an OH group, an X ₂ R _{20 group} a substituted benzoyl group or a phenoxycarbonyl group; the R ₁₅ and the R ₁₆ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, and a C ₁ -C ₅ substituted by a carboxyl group; alkyl group, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; optionally substituted with one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN C ₁ -C ₄ alkanoyloxy, substituted aroyloxy, C ₂ -C ₁₈ alkyl radical; a C ₅ -C ₇ cycloalkylene, phenylene, O, S, NR ₁₇ C inserted ₂ -C ₁₈ alkyl; C ₅ -C ₇ cycloalkyl optionally substituted by one or more C ₁ -C ₄ alkyl, phenyl, halogen atom, CN; optionally by one or more C ₁ -C _4- alkyl, C ₁ -C ₄ alkoxy, carboxy, C ₁ -C ₁₂ alkyl acyl, C ₅ -C ₆ cycloalkyl formyl, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ An alkyl group, a benzoyl group, an XR ₁₇ group, a halogen atom, a phenyl group substituted by CN; the R ₁₇ is a C ₁ -C ₄ alkyl group; and the R ₁₈ and the R ₁₉ are each independently a group consisting of the following: is selected from: hydrogen atom, C ₁ -C ₁₈ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl , C ₅ -C ₇ cycloalkyl, phenyl; optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkyl, C ₃ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl , C ₁ -C ₄ alkanoyloxy, a C ₁ -C ₁₈ alkyl group substituted with an aroyloxy group; optionally substituted by one or more C ₃ -C ₇ cycloalkylene groups, phenylene groups, O, C ₂ -C ₁₈ inserted by S and NR ₁₇ An alkyl group; a C ₅ -C ₇ cycloalkyl group optionally substituted by one or more C ₁ -C ₄ alkyl groups, a phenyl group, a halogen atom, CN; and optionally any one or more C ₁ -C ₄ alkyl groups a carboxyl group, a C ₁ -C ₁₂ alkyl acyl group, a C ₅ -C ₆ cycloalkyl formyl group, a C ₂ -C ₄ alkyl acyl group substituted by a C ₅ -C ₆ cycloalkyl group, an aryl acyl group, XR ₁₇ , a phenyl group, a halogen atom, a phenyl group substituted by CN; the R ₂₀ , the R ₂₁ , the R ₂₂ , and the R ₂₃ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group; , C ₃ -C ₇ cycloalkyl; C ₁ -C ₁₈ alkyl substituted by halogen, CN, C ₁ -C ₄ alkoxy; by one or more oxygen atoms, C ₅ -C ₇ hypocycloalkane a C ₂ -C ₁₈ alkyl group in which a phenylene group is inserted; a C ₁ -C ₃ alkyl group substituted by a phenyl group, a C ₃ -C ₇ cycloalkyl group; a phenyl group, a naphthyl group, a benzoyl group; Any halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio, NR ₂₄ R ₂₅ , C ₁ -C ₁₂ alkane yl group, a benzoyl group substituted with phenyl group, a naphthyl group, a benzoyl group; the R _24, the R ₂₅ are each C ₁ -C ₄ alkyl; or NR ₂₄ R ₂₅ together is Morpholine, piperidine, piperazine, N- methylpiperazine, pyrrole. An asymmetric diketone oxime compound comprising one of the group consisting of the following compounds of the formulae VI and VII: Wherein the Ar _{1 is} selected from a C ₆ -C ₂₀ o-arylene or a C ₃ -C ₂₀ o-heteroaryl group substituted by the X ₁ , the C ₆ -C ₂₀ o-arylene group or the C ₃ - The C ₂₀ ortho-heteroaryl group is bonded to the Y ₁ and a carbonyl group by two adjacent atoms to form a ring structure, and the substituents on the remaining atoms are each selected from the group consisting of a hydrogen atom, a halogen atom, and C _{1 .} -C ₁₂ alkyl, C ₅ -C ₇ cycloalkyl, C ₁ -C ₄ alkyl substituted by C ₅ -C ₇ cycloalkyl, C ₁ -C ₁₂ alkoxy, C ₁ -C ₄ alkyl Benzyloxy, C ₁ -C ₃ alkylenedioxy, R ₂ C(O)O, C ₁ -C ₁₂ alkylthio, C ₁ -C ₄ alkylphenylthio, CN, carboxyl, C ₁ -C ₁₂ alkoxycarbonyl group, an arylcarbonyl group, heteroarylcarbonyl _{group, X 3 R 18, C 1} -C 4 alkyl group, C1-C8 alkyl group a phenoxy group, C ₅ -C ₆ cycloalkyl Alkyl acyl phenoxy, C ₅ -C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl phenoxy, aryl acyl phenoxy, heteroaryl acyl phenoxy, R ₂ C(O) O-substituted C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylphenylthio group, C ₁ -C ₈ alkyl acyl phenylthio group, C ₅ -C ₆ cycloalkyl phenyl phenylthio group, C _5- C ₆ cycloalkyl substituted C ₁ -C ₄ alkyl acyl a phenylthio group, an aryl acyl phenylthio group, a heteroaryl acyl phenylthio group; one or more C ₁ -C ₁₂ alkoxy groups, a C ₁ -C ₄ alkylbenzyloxy group, a R ₂ C(O) group O-substituted C ₁ -C ₄ alkoxy; phenyl and optionally by one or more C ₁ -C ₄ alkyl, carboxy, C ₁ -C ₁₂ alkyl acyl, aryl acyl, heteroaryl acyl, X ₃ R ₁₇ , phenyl, halogen atom, CN substituted phenyl; epoxy propyl group, wherein the epoxy group arbitrarily homogenizes a C ₁ -C ₄ alkyl aldehyde, a ketone condensation; the X _{3 is} selected from O, S and NR _22; the Ar ₂ is selected from: by the X ₁ C ₁ is connected to the Ar ₆ -C ₂₀ arylene group, through which X ₁ C ₃ -C ₂₀ heteroarylene group is connected to the Ar _1; and the X ₁ is selected from the group consisting of O, S, NR ₁₈ and Y ₂ -Z ₁ -Y ₂ ; the Y1 is selected from the group consisting of: (CH ₂ ) _m CR ₁₅ R ₁₆ , NR ₁₉ , O(CR ₁₅ R ₁₆ ) _m , S(CR ₁₅ R ₁₆ ) _m , (CR ₁₅ R ₁₆ ) _m C=O and S=O, the m is 0 or 1; the Z _{1 is} composed of the following group group elected: C ₁ -C ₁₀ linear alkylene, C ₁ -C ₁₀ branched alkylene, substituted by one or more oxygen atom or sulfur atom attached to the end groups C ₁ -C ₁₀ linear alkylene One or more C atom or sulfur atom attached to a terminal end ₁ -C ₁₀ branched alkylene, substituted by one or more oxygen atoms or sulfur atom inserted straight chain C ₂ -C ₁₀ alkylene group, substituted with one or more oxygen or sulfur atom inserted branched C ₂ -C ₁₀ alkylene group unsubstituted C ₆ -C ₂₀ arylene group, and an optionally substituted C ₆ -C ₂₀ arylene; Y ₂ of the following The group formed is selected from: O, S, NR ₁₈ and OC(O); the R ₁ is selected from the group consisting of hydrogen atom, C ₁ -C ₁₈ alkyl group, diphenylphosphonyl group, C ₁ -C ₄ alkoxy)phosphono; C ₂ -C ₁₈ alkyl optionally substituted by one or more C ₃ -C ₇ cycloalkyl, phenyl, OR ₂₀ , SR ₂₁ , NR ₂₂ R ₂₃ Wherein the phenyl group is any one or more of halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkane Acyloxy, aroyloxy substituted; C ₂ -C ₁₈ alkyl group inserted by C ₃ -C ₇ cycloalkylene, phenylene, O, S, NR ₂₂ ; C ₃ -C ₈ cycloalkyl , CN, NO _2, phenyl; optionally one or more halogen atoms, C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl , CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted phenyl; C ₁ -C ₁₂ alkyl group, C ₁ -C ₁₂ alkoxycarbonyl, wherein the alkyl group optionally substituted with one or more Halogen atom, C ₁ -C ₄ alkyl group, C ₅ cycloalkyl group, C ₆ cycloalkyl group, phenyl group, CN, OH, X ₃ R ₂₀ substituted; C ₁ -C ₁₂ alkyl acyl group, C ₁ -C _{a 12} alkoxycarbonyl group, wherein the alkyl group is optionally interrupted by one or more phenylene groups, X ₃ ; the phenyl group unsubstituted benzoyl group, phenoxycarbonyl group; the phenyl group is optionally one or more halogen atoms, a benzoyl group or a phenoxycarbonyl group substituted with C ₁ -C ₄ alkyl, C ₅ cycloalkyl, C ₆ cycloalkyl, phenyl, CN, OH, X ₂ R ₂₀ ; the R ₁₅ , the R ₁₆ are each independently selected from the group consisting of the following: a hydrogen atom, C ₁ -C ₁₈ alkyl, carboxy substituted C ₁ -C ₅ alkyl, C ₁ -C ₄ alkoxy group substituted with C ₁ - C ₅ -alkyl, R ₂ C(O)O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; optionally substituted by one or more halogen atoms, C ₁ -C ₄ alkane Substituted by C ₅ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy C ₂ -C ₁₈ alkyl radical; a C ₅ -C ₇ cycloalkylene, phenylene, O, S, NR ₁₇ inserted C ₂ -C ₁₈ alkyl; optionally substituted with one or more C ₁ -C a C ₅ -C ₇ cycloalkyl group substituted with ₄ alkyl, phenyl, halogen atom, CN; optionally substituted by one or more C ₁ -C ₄ alkyl groups, C ₁ -C ₄ alkoxy group, carboxyl group, C ₁ -C ₁₂ alkyl acyl group, C ₅ -C ₆ cycloalkyl formyl group, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl acyl group, benzoyl group, XR ₁₇ , halogen atom, CN substitution a phenyl group; the R ₁₇ is a C ₁ -C ₄ alkyl group; the R ₁₈ and the R ₁₉ are each independently selected from the group consisting of a hydrogen atom, a C ₁ -C ₁₈ alkyl group, and a C ₁ -C group; ₄ alkoxy group substituted with C ₁ -C ₅ alkyl group, R ₂ C (O) O substituted C ₁ -C ₄ alkyl, C ₅ -C ₇ cycloalkyl, phenyl; optionally substituted with one or a plurality of halogen atoms, C ₁ -C ₄ alkyl, C ₃ -C ₇ cycloalkyl, heterocycloalkyl, phenyl, heteroaryl, CN, C ₁ -C ₄ alkanoyloxy, aroyloxy substituted C ₁ -C ₁₈ alkyl; optionally substituted with one or more C ₃ -C ₇ cycloalkylene, phenylene, O, S, NR ₁₇ inserted C ₂ -C ₁₈ alkyl; optionally One or more C ₁ -C ₄ alkyl groups a phenyl group, a halogen atom, a C ₅ -C ₇ cycloalkyl group substituted by CN; and optionally one or more C ₁ -C ₄ alkyl groups, a carboxyl group, a C ₁ -C ₁₂ alkyl acyl group, a C ₅ -C formyl ₆ cycloalkyl, C ₅ -C ₆ cycloalkyl substituted C ₂ -C ₄ alkyl group, aryl group, XR _17, a phenyl group, a halogen atom, CN substituted phenyl; the R ₂₀ , R ₂₁ , R ₂₂ , and R ₂₃ are each independently selected from the group consisting of hydrogen atom, C ₁ -C ₁₈ alkyl group, C ₃ -C ₇ cycloalkyl group; halogen, CN, C a C ₁ -C ₁₈ alkyl group substituted with a ₁ -C ₄ alkoxy group; a C ₂ -C ₁₈ alkyl group inserted by one or more oxygen atoms, a C ₅ -C ₇ cycloalkylene group, a phenylene group; C ₁ -C ₃ alkyl substituted by phenyl, C ₃ -C ₇ cycloalkyl; phenyl, naphthyl, benzoyl; and optionally halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy, phenylthio, NR ₂₄ R ₂₅ , C ₁ -C ₁₂ alkyl acyl, phenyl substituted by benzoyl, naphthyl, benzene Formyl; the R ₂₄ , the R ₂₅ are each a C ₁ -C ₄ alkyl group; or the NR ₂₄ R ₂₅ together are morpholine, piperidine, piperazine, N-methylpiperazine, pyrrole . A photocurable composition comprising a photoinitiator and at least one carbon-carbon double bond compound which is capable of undergoing radical polymerization, the photoinitiator comprising at least one asymmetric diterpene ester compound described in claim 1. The photocurable composition according to claim 18, further comprising an additive. The photocurable composition according to claim 19, wherein the photoinitiator accounts for 0.05 to 25% by weight of the total composition, and the carbon-carbon double bond compound and the additive account for the remaining percentage other than the above components. The photocurable composition according to claim 18 or 19, wherein the carbon-carbon double bond compound is an acrylate compound or a methacrylate compound. The photocurable composition according to claim 19, wherein the additive is selected from the group consisting of a developing resin, a pigment, and a dye. A method of applying a photocurable composition, comprising: (1) first using the photocurable composition of claim 18 or 19 for producing one of the following colored or transparent articles: paint, ink, adhesive, Photoresist and photoresist; and (2) the article is used in printing, 3D printing, color filter production in display devices, electronic device packaging, printed circuit board dielectric layers. A method of curing a photocurable composition, which comprises forming a coating layer on a substrate on a substrate according to any one of claims 18 or 19, and curing the coating layer by irradiation with light having a wavelength of from 190 to 600 nm. The method of curing a photocurable composition according to claim 24, wherein the light is from a sun, a mercury lamp, a high pressure mercury lamp or an LED lamp. A method for producing a convex pattern by using a photocurable composition, which first dilutes the photocurable composition according to any one of claims 18 or 19 with a solvent; and then applies the diluted photocurable composition to a substrate. The unexposed portion is removed by drying, exposure, and development to obtain a raised pattern. A color filter comprising black, red, green, and blue primitives, comprising an asymmetric diterpene ester compound, photocurable monomer, alkali soluble resin, pigment, and additive comprising at least one of claims 1 or 6. The composition is obtained by sequential coating, exposure, development, and heat treatment. A method of manufacturing a color filter comprising black, red, green, and blue primitives, the method of manufacturing comprising at least one asymmetric diterpene ester compound according to claim 1 or 6, light The composition comprising a curing monomer, an alkali-soluble resin, a pigment, and an additive is sequentially coated, exposed, developed, and heat-treated, and finally the color filter is obtained.