A kind of 9-phenylacridine macromolecular photosensitizer and its preparation method and application

A technology of phenylacridine and macromolecules, which is applied to 9-phenylacridine macromolecular photosensitizers and their preparation. The application of the photosensitizers in the field of photocuring can solve the problem of reducing product precision and affecting dryness. Film use, cumbersome process and other problems, to achieve the effect of reducing odor and toxicity, preventing yellowing and aging, and high photoactivity

Active Publication Date: 2020-02-07
CHANGZHOU TRONLY NEW ELECTRONICS MATERIALS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these existing acridine compounds have more or less disadvantages such as unsatisfactory solubility and poor sensitivity enhancement effect when used as photosensitizers.
9-Phenylacridine is one of the most widely used products among the existing acridine photosensitizers. As a small molecule photosensitizer, it is often difficult to separate from the reactant, difficult to recycle or not compatible with the system during use. Good, easy to coagulate and precipitate, etc., resulting in reduced reaction efficiency and affecting material properties
In particular, the extremely low water solubility of 9-phenylacridine has seriously affected its popularization and use as a photosensitizer in the field of photocuring, especially in the field of dry film photoresist.
In the dry film development stage, the unexposed part is usually washed away with alkaline aqueous solution, and 9-phenylacridine will be precipitated and adsorbed on the surface of the circuit board due to its extremely low water solubility, which not only affects the use of the dry film, but also It will also reduce the precision of the product, so it is necessary to increase the surface cleaning process of the circuit board in the follow-up, resulting in cumbersome process and greatly increased cost

Method used

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  • A kind of 9-phenylacridine macromolecular photosensitizer and its preparation method and application
  • A kind of 9-phenylacridine macromolecular photosensitizer and its preparation method and application
  • A kind of 9-phenylacridine macromolecular photosensitizer and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] (1) Preparation of Intermediate 1a

[0047]

[0048] Add p-hydroxybenzoic acid 165.6g (1.2mol), diphenylamine 169.0g (1.0mol), zinc chloride 244.8g (1.8mol) and 85% phosphoric acid 115.3g (1.0mol) in the 1000ml four-necked bottle, stir and heat up to 200-210°C, react for 6h. Then cool down to 130-140°C, add 400g of 30% sulfuric acid dropwise, keep stirring at 80°C for 2h, add 300g of 80°C water and stir for 0.5h, let stand to separate the lower layer of water, then add 300g of water to repeat the above operation, and finally add to the reaction bottle 300g of ammonia water was added to the mixture, a large amount of orange solid was precipitated, suction filtered at room temperature, rinsed with methanol, and dried to obtain 257.4g of solid, namely intermediate 1a, with a purity of 98%;

[0049] The structure of intermediate 1a was confirmed by LCMS.

[0050] Mass spectrometry was used to obtain the 272 and 273 molecular fragment peaks with the help of the software...

Embodiment 2

[0063] (1) Preparation of Intermediate 2a

[0064]

[0065] Add 219.6g (1.2mol) of 4-hydroxyl-3-nitrobenzoic acid benzoic acid, 169.0g (1.0mol) of diphenylamine, 244.8g (1.8mol) of zinc chloride and 115.3g of 85% phosphoric acid in the 1000ml four-necked bottle (1.0mol), stir and heat up to 200-210°C, react for 6h, follow the reaction to the liquid phase. Cool down to 130-140°C, add 400g of 30% sulfuric acid dropwise, keep stirring at 80°C for 2 hours, add 300g of 80°C water and stir for 0.5h, let stand to remove the lower layer of water, then add 300g of water to repeat the above operation, and finally pour into the reaction bottle After adding 300g of ammonia water, a large amount of orange solid was precipitated, suction filtered, rinsed with methanol, and dried to obtain 300.2g of solid, namely intermediate 2a, with a purity of 98% and a yield of 95%;

[0066] The structure of intermediate 2a was confirmed by LCMS.

[0067] Mass spectrometry was used to obtain molecul...

Embodiment 3-9

[0079] Referring to the method of Example 1 or 2, the product 3-9 having the following structure was synthesized.

[0080] Product 3:

[0081]

[0082] Product 4:

[0083]

[0084] Product 5:

[0085]

[0086] Product 6:

[0087]

[0088] Product 7:

[0089]

[0090] Product 8:

[0091]

[0092] Product 9:

[0093]

[0094]

[0095] performance evaluation

[0096] The application performance of the photosensitizer of the present invention was evaluated by preparing an exemplary photocurable composition (ie, a photosensitive resin composition).

[0097] 1. Preparation of performance evaluation objects

[0098]

[0099] The photosensitive resin composition and propylene glycol monoethyl ether acetate having the composition shown in Table 1 were fully stirred and mixed, and coated on the surface of a 19 μm thick polyethylene terephthalate film as a support using a bar , evenly coated, and then dried in a dryer at 95° C. for 4 minutes to form a ph...

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Abstract

Disclosed are a 9-phenylacridine macromolecule photosensitizer, and a preparing method and use thereof. The 9-phenylacridine macromolecule photosensitizer comprises at least one of the compounds having a structure as shown in formula (I), in which R1 is a linear or branched C1-C60 alkyl group with a valency of m + n, wherein a -CH2- thereof may be optionally substituted by oxygen, sulphur or 1,4-phenylene; each A independently represents -[(CHR4)x-O]y-, wherein each R4 independently represents hydrogen, a methyl group, or an ethyl group, x is an integer of 1-10, and y is an integer of 1-20; R2 represents a linear or branched C1-C20 alkylene group, wherein a -CH2- thereof may be optionally substituted by oxygen, sulphur or a phenylene; R3 represents hydrogen or a substituent group; m represents an integer of 0-20, and n represents an integer of 1-20. When used in a photocuring system, the photosensitizer has good compatibility and good photosensitivity improving effect, and a film prepared therefrom has excellent resolution, adhesion, and high solubility in water.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a 9-phenylacridine macromolecular photosensitizer, a preparation method thereof, and an application of the photosensitizer in the field of photocuring. Background technique [0002] Acridine compounds are macrocyclic conjugated systems with a rigid planar structure and strong fluorescence properties. They are good fluorescent reagents and can be used as photoinitiators in photopolymerization systems, and can also be used as sensitizers to initiate photoinitiation. agent for photopolymerization. 9-Phenylacridine is a derivative of acridine, which belongs to the biphenyl structure. Under ultraviolet light, X-rays or light, it can initiate photocurable materials (photocurable coatings, photocurable coatings, Ink and photoresist, etc.) are cross-linked and cured, and are stable in nature, and have good photosensitive properties in photo-curable materials composed of unsa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G03F7/004C08F2/50C08G65/333C07D219/02
CPCC07D219/02C08F2/50C08G65/33317G03F7/0045C07D219/00C08F2/46C08F2/48C08G65/33393G03F7/004
Inventor 钱晓春衡京胡春青翁云峰于培培
Owner CHANGZHOU TRONLY NEW ELECTRONICS MATERIALS
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