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Pyrazoline sensitizer as well as preparation method and application thereof

A technology of pyrazoline and sensitizer, which is applied in the field of pyrazoline sensitizer and its preparation, and can solve the problems of poor sensitivity enhancement effect and unsatisfactory solubility, etc.

Active Publication Date: 2015-09-09
CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when these existing pyrazoline compounds are used as sensitizers, there are more or less disadvantages such as unsatisfactory solubility and poor sensitivity enhancement effect.

Method used

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  • Pyrazoline sensitizer as well as preparation method and application thereof
  • Pyrazoline sensitizer as well as preparation method and application thereof
  • Pyrazoline sensitizer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Preparation of intermediate a:

[0042]

[0043] Add 183g of p-hydroxybenzaldehyde, 5g of catalyst pyridinium p-toluenesulfonate, and 300mL of dichloromethane into a 1000mL four-necked flask, and add 126g of dihydropyran dropwise at a temperature of 50°C for about 1 hour. Stir for 10 h, follow the reaction until the liquid phase does not change and close the reaction, and then remove the dichloromethane by rotary evaporation to obtain 275 g of intermediate a with a purity of 98%, which is directly used in the next reaction;

[0044] (2) Preparation of intermediate 1b:

[0045]

[0046] Add 247g of intermediate a, 235g of benzophenone as raw material c, and 300mL of methanol into a 1000mL four-neck flask, stir in a water bath at room temperature, add 80g of 40% sodium hydroxide solution dropwise within 2h, continue stirring for 6h, and follow the reaction in the liquid phase until no Change again, filter, methanol recrystallization, dry to obtain solid 415g, nam...

Embodiment 2

[0061] The synthesis of intermediate 2e was carried out with reference to Example 1.

[0062] Preparation of product 2:

[0063]

[0064] Add 7.36g of compound 2e, 27.2g of raw material 2f(9-EO), 0.1g of tetraisopropyl titanate, 0.1g of p-hydroxyanisole, and 100mL of xylene into a 500mL four-neck flask, and control the temperature at 90-100°C Heat and stir, distill out the methanol produced by the reaction while heating, and add xylene in time until no methanol is distilled out, filter while it is hot, carry out vacuum distillation on the obtained filtrate, distill out toluene until completely, and obtain a light yellow viscous The thick product is the product 2.

Embodiment 3-12

[0066] Referring to the method of Example 1, the product 3-13 with the following structure is synthesized:

[0067]

[0068]

[0069]

[0070] performance evaluation

[0071] By preparing an exemplary photocurable composition (ie, a photosensitive resin composition), the application performance of the sensitizer represented by formula (I) of the present invention is evaluated.

[0072] 1. Preparation of performance evaluation objects

[0073]

[0074] Fully stir and mix the photosensitive resin composition and PGMEA (propylene glycol methyl ether acetate) with the composition shown in Table 1, and use a bar to coat the surface of a 19 μm thick polyethylene terephthalate film as a support Evenly coated on the surface, and then dried in a dryer at 95° C. for 4 minutes to form a photosensitive resin layer with a thickness of 40 μm.

[0075] Next, a polyethylene film having a thickness of 23 μm was bonded as a protective layer on the surface of the photosensitive re...

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Abstract

The invention provides pyrazoline sensitizer having a structure shown in the formula (I) as shown in the specification. The pyrazoline sensitizer has absorption waveband which is between 350nm and 440nm, is suitable for a light-curing system and particularly suitable for a system containing biimidazole photoinitiator. The pyrazoline sensitizer has ideal solubility and good light sensitivity improving effect. and a prepared film is good in resolution and adhesive force.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a pyrazoline sensitizer, a preparation method thereof, and an application of the sensitizer in the field of photocuring. Background technique [0002] UV curing technology has been widely used due to its fast curing speed and low environmental pollution. The photoinitiator plays a decisive role in the curing efficiency of the entire curing system. In actual use, some photoinitiators cannot initiate polymerization well due to the limitation of the absorption wavelength, and often need to be used in conjunction with a sensitizer to improve the initiation efficiency. The sensitizer can continuously transfer the absorbed energy to the photoinitiator, which is equivalent to the catalyst of the photochemical reaction. However, the application of sensitizers is restricted by many factors, such as solubility, matching of absorption wavelength and so on. At this stage, findi...

Claims

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Application Information

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IPC IPC(8): C07D231/06C08F265/04C08F226/02C08F220/20C08F4/00
CPCC07D231/06C08F4/00C08F220/20C08F226/02C08F265/04
Inventor 钱晓春胡春青衡京王兵于培培
Owner CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD
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