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CN-121990933-A - Triarylamine-based compound, preparation method thereof, photo-curing adhesive and application

CN121990933ACN 121990933 ACN121990933 ACN 121990933ACN-121990933-A

Abstract

The application discloses a triarylamine-based compound, a preparation method thereof, a photo-curing adhesive and application thereof. The triarylamine-based compounds include compounds having a core structure of a ditriarylamine structural unit and a side chain structure of an organic group having a carbon-carbon double bond. The triarylamine-based compound not only has the characteristics of wide band gap, high light transmittance, high refractive index and high stability, but also can be cured in a thermal initiation or photoinitiation mode to prepare a coating, and has the advantage of high-efficiency polymerizability.

Inventors

  • ZHAO BAOMIN
  • ZHOU FU

Assignees

  • 宁波天璇新材料科技有限公司

Dates

Publication Date
20260508
Application Date
20241108

Claims (10)

  1. 1. A triarylamine-based compound, characterized in that the triarylamine-based compound comprises a compound having a double triarylamine structural unit as a core structure and an organic group having a carbon-carbon double bond as a side chain structure.
  2. 2. The triarylamine-based compound of claim 1 wherein said core structure comprises a structure represented by formula I, Wherein Ar 10 、Ar 21 、Ar 22 、Ar 23 and Ar 24 each independently comprise at least one of a substituted or unsubstituted C 6～50 arylene group, a substituted or unsubstituted C 2～50 heteroarylene group, Represents a binding site; The side chain structure comprises at least one of a structure shown in a formula II-1, a structure shown in a formula II-2, a structure shown in a formula II-3 and a structure shown in a formula II-4, Wherein R 21 、R 22 、R 23 and R 24 each independently comprise at least one of a substituted or unsubstituted C 1～20 alkoxy, a substituted or unsubstituted C 6～20 heteroarylene; a1, a2, a3 and a4 are each independently 0 or an integer of 1 to 12, and a1, a2, a3 and a4 are not 0 at the same time; X 1 、X 2 、X 3 and X 4 each independently comprise at least one of hydrogen, vinyl, alpha-methyl vinyl, acryl, alpha-methyl acryl, vinyl phenyl, alpha-methyl vinyl phenyl, and X 1 、X 2 、X 3 and X 4 are not simultaneously hydrogen, Representing the binding site.
  3. 3. The triarylamine-based compound of claim 1 wherein the triarylamine-based compound comprises a compound having a structure represented by formula III, Wherein Ar 10 、Ar 21 、Ar 22 、Ar 23 and Ar 24 each independently comprise at least one of a substituted or unsubstituted C 6～50 arylene, a substituted or unsubstituted C 2～50 heteroarylene; R 21 、R 22 、R 23 and R 24 each independently comprise at least one of a substituted or unsubstituted C 1～20 alkoxy, a substituted or unsubstituted C 6～20 heteroarylene; a1, a2, a3 and a4 are each independently 0 or an integer of 1 to 12, and a1, a2, a3 and a4 are not 0 at the same time; X 1 、X 2 、X 3 and X 4 each independently comprise at least one of hydrogen, vinyl, α -methyl vinyl, acryl, α -methyl acryl, vinyl phenyl, α -methyl vinyl phenyl, and X 1 、X 2 、X 3 and X 4 are not both hydrogen.
  4. 4. The triarylamine-based compound of claim 2, wherein Ar 10 、Ar 21 、Ar 22 、Ar 23 and Ar 24 each independently comprises at least one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted oxadiazolyl group, a phthalimidyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted naphtho- (benzofuranyl) group, a substituted or unsubstituted naphthofuranyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, and/or Ar 10 、Ar 21 、Ar 22 、Ar 23 and Ar 24 are each independently represented by the following formulae and derivatives thereof: Wherein Z 1 、Z 2 、Z 3 and Z 4 each independently comprises at least one of hydrogen, deuterium, F, cl, CN, C 1～24 alkyl, C 1～24 alkoxy, phenyl, biphenyl, naphthyl, triphenylene, anthryl, pyrenyl and phenanthryl, d 1 、d 2 each independently is 0 or an integer of 1-3, Representing binding sites, and/or Ar 10 、Ar 21 、Ar 22 、Ar 23 and Ar 24 are each independently represented by the following formulae and derivatives thereof: Wherein, the T 1 and T 2 each independently include at least one of an alkyl group of C 1～24 , a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenoxazine group, and a substituted or unsubstituted phenothiazine group.
  5. 5. The triarylamine-based compound of any one of claims 1-4, wherein the side chain structure comprises At least one of the above-mentioned materials, And each of m and n is independently an integer of 1 to 24.
  6. 6. The triarylamine-based compound of any one of claims 1 to 4, wherein X 1 、X 2 、X 3 and X 4 each independently comprises at least one of hydrogen, vinyl, alpha-methyl vinyl, acryl, alpha-methacryl, vinyl phenyl, alpha-methyl vinyl phenyl, and at least two of X 1 、X 2 、X 3 and X 4 are not both hydrogen, or X 1 、X 2 、X 3 and X 4 each independently comprise at least one of hydrogen, vinyl, alpha-methyl vinyl, acryl, alpha-methyl acryl, vinyl phenyl, alpha-methyl vinyl phenyl, and at least three of X 1 、X 2 、X 3 and X 4 are not hydrogen at the same time, or X 1 、X 2 、X 3 and X 4 each independently comprise at least one of vinyl, alpha-methyl vinyl, acryl, alpha-methyl acryl, vinyl phenyl, alpha-methyl vinyl phenyl.
  7. 7. A process for the preparation of a triarylamine-based compound as set forth in any one of claims 1 to 6, comprising the steps of: Under the condition of being capable of reacting, carrying out a first reaction on a first raw material comprising a first reactant and a second reactant to prepare a first intermediate; Carrying out hydroxylation reaction on the first intermediate under the condition of reactivity to prepare a second intermediate; Under the condition of being capable of reacting, the second intermediate is subjected to chain extension reaction and then alkenyl reaction to prepare the triarylamine-based compound; wherein the first reactant comprises a compound with a structure shown in a formula IV, Ar 22 and Ar 23 each independently comprise at least one of a substituted or unsubstituted C 6～50 arylene, a substituted or unsubstituted C 2～50 heteroarylene, Y 2 and Y 3 each independently comprise at least one of hydrogen, methoxy, and Y 2 and Y 3 are not both hydrogen; the first reactant comprises at least one of a compound with a structure shown in a formula V and a compound with a structure shown in a formula VI, Ar 20 、Ar 30 、Ar 21 and Ar 24 each independently comprise at least one of a substituted or unsubstituted C 6～50 arylene, a substituted or unsubstituted C 2～50 heteroarylene, Y 1 and Y 4 each independently comprise at least one of hydrogen, methoxy, and Y 5 and Y 6 each independently comprise at least one of F, br, cl.
  8. 8. The method of claim 7, wherein said chain extension reaction under reactive conditions comprises: Reacting the second intermediate with a compound of the structure of formula VIII under reactive conditions, Y 10 -R 10 -OH of the formula VII, R 10 comprises at least one of a substituted or unsubstituted C 1-10 alkylene group, Y 10 comprises at least one of bromine, fluorine, chlorine, and/or The alkenylation reaction includes: And carrying out the second reaction on the product obtained after the chain extension reaction and a third reactant containing double bonds under the reactive condition to prepare the triarylamine-based compound, wherein the third reactant containing double bonds comprises a compound with a structure shown in a formula VII, R 41 comprises at least one of a substituted or unsubstituted acyl chloride group, a substituted or unsubstituted benzene acid group, and/or The hydroxylation reagent of the hydroxylation reaction comprises at least one of boron tribromide, boron trichloride, aluminum trichloride or pyridine hydrochloride, and/or The hydroxylation solvent for the hydroxylation reaction comprises at least one of dichloromethane, chloroform, carbon tetrachloride, 1-dichloroethane, 1, 2-dichloroethane, cyclohexane, n-hexane or petroleum ether.
  9. 9. A photocurable adhesive comprising the triarylamine-based compound according to any one of claims 1 to 6 or the triarylamine-based compound prepared by the preparation method of claim 7 or 8.
  10. 10. Use of a photo-curable glue according to claim 9 in photoresists, lens coatings, diffractive optical waveguides or nanopresses.

Description

Triarylamine-based compound, preparation method thereof, photo-curing adhesive and application Technical Field The application belongs to the technical field of optical materials, and particularly relates to a triarylamine-based compound, a preparation method thereof, a photo-curing adhesive and application thereof Background In recent years, resin-type dispersions have been prepared by combining inorganic nanoparticle dispersions with transparent resins or films, and find good application in the optical field, such as zirconia nanoparticles, silica nanoparticles. The use of the dispersion of zirconia resin for preparing optical films such as brightness enhancement films and antireflection films can be used in LCD displays to increase the brightness and definition of the screen or to obtain high refractive index films in other optical devices. In the above applications, not only is such a material required to have a high refractive index and a low viscosity, but also it is required to have good compatibility after being mixed with a resin in downstream applications to make a UV curable adhesive that can be uniformly applied to the surface of an optical film. However, the incompatibility of inorganic nanoparticles such as zirconia or titania with resins can lead to non-uniformity of resin dispersions containing the inorganic nanoparticles, and the condition control during the synthesis of inorganic oxide nanoparticles is difficult, and the problems of poor particle size polydispersity and complex particle crystal phase structure of a large number of nanoparticles often seriously affect the use and long-term stability of optical films or resins, and limit the application potential of corresponding materials. Therefore, to meet the market demand, it is important to prepare a UV curable gel with good compatibility and high light transmittance from a high refractive index polymer unit with an all-organic or very low inorganic nanoparticle content. Although some all-polymer optical glues have been successfully prepared nowadays, most of them have problems of low refractive index, difficulty in UV curing, etc., so that the effect is affected when applied to the downstream display field. For example, the refractive index of the cured polymer is rarely more than 1.7, which is an acrylic monomer, an alkenylcarbazole monomer, or the like. Therefore, the application is particularly provided in view of the fact that the development of the all-organic UV curing adhesive which is simple in process, coordinated in various indexes in a system, good in compatibility, stability and higher in refractive index is required, and the all-organic UV curing adhesive has important significance for later production. Disclosure of Invention Accordingly, the technical problem underlying the present application is to overcome the above drawbacks of the prior art, which aims to provide a triarylamine-based compound having the advantages of wide band gap, high light transmittance, high refractive index and high stability. In a first aspect of the present application, there is provided a triarylamine-based compound comprising a compound having a double triarylamine structural unit as a core structure and an organic group having a carbon-carbon double bond as a side chain structure. The compound provided by the application contains a conjugated system taking a double triarylamine structure as a core structure, takes an electron-rich conjugated group of triarylamine as a donor unit, forms a multi-conjugated structure with strong donor characteristics, and constructs a corresponding curable structural unit containing carbon-carbon double bonds at the same time, so that the triarylamine-based compound has the advantages of wide band gap, high light transmittance in a visible light region, high refractive index, high stability and high efficiency photopolymerization. In any embodiment, the core structure comprises a structure of formula I, Wherein Ar 10、Ar21、Ar22、Ar23 and Ar 24 each independently comprise at least one of a substituted or unsubstituted C 6～50 arylene group, a substituted or unsubstituted C 2～50 heteroarylene group,Represents a binding site; The side chain structure comprises at least one of a structure shown in a formula II-1, a structure shown in a formula II-2, a structure shown in a formula II-3 and a structure shown in a formula II-4, Wherein R 21、R22、R23 and R 24 each independently comprise at least one of a substituted or unsubstituted C 1～20 alkoxy, a substituted or unsubstituted C 6～20 heteroarylene; a1, a2, a3 and a4 are each independently 0 or an integer of 1 to 12, and a1, a2, a3 and a4 are not 0 at the same time; x 1、X2、X3 and X 4 each independently comprise at least one of hydrogen, vinyl, alpha-methyl vinyl, acryl, alpha-methyl acryl, vinyl phenyl, alpha-methyl vinyl phenyl, and X 1、X2、X3 and X 4 are not both hydrogen, and- -represents a binding site. In any embodiment, the triarylamine-based compound comprises a co