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Fluorine-containing adamantane derivative, fluorine-containing adamantane derivative having polymerizable group, resin composition containing the same, and antireflection film

A polymeric group, adamantane technology, applied in the preparation of organic compounds, organic chemistry, chemical instruments and methods, etc., can solve the problem of scratch resistance, heat generation or insufficient heat resistance of reflow soldering, and cannot obtain sufficient surface Hardness and other issues, to achieve the effect of low refractive index and good mechanical properties

Inactive Publication Date: 2009-05-13
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since they are linear, sufficient surface hardness cannot be obtained, and there are problems in scratch resistance, etc.
In addition, in optical fibers and optical waveguides, it is known that C-H bonds in organic compounds are the cause of light loss, and the countermeasures are to use materials that replace C-H bonds with C-F bonds, one of which is to use linear fluorine-containing acrylates Resin (for example, refer to Patent Document 7), but the heat resistance to withstand heat generated during communication or reflow soldering is not enough

Method used

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  • Fluorine-containing adamantane derivative, fluorine-containing adamantane derivative having polymerizable group, resin composition containing the same, and antireflection film
  • Fluorine-containing adamantane derivative, fluorine-containing adamantane derivative having polymerizable group, resin composition containing the same, and antireflection film
  • Fluorine-containing adamantane derivative, fluorine-containing adamantane derivative having polymerizable group, resin composition containing the same, and antireflection film

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Example 1 (synthesis of perfluoro-1,3-adamantanedimethanol)

[0089] 5.0 L of 1,1,2-trichlorotrifluoroethane was measured in a 10 L reaction vessel having a condenser tube, a NaF particle packed bed, and a thermometer, and the inner temperature was kept at 0°C. Next, blow in nitrogen at 2000ml / min, blow in fluorine at 630ml / min, and after 3 minutes, dissolve 100g of diethyl adamantanedicarboxylate in 1.0L of 1,1,2-trichlorotrifluoro solution in ethane.

[0090] Then, the flow rate of nitrogen was changed to 1200 ml / min, the flow rate of fluorine was changed to 300 ml / min, and a solution obtained by dissolving 4 g of benzene in 30 mL of 1,1,2-trichlorotrifluoroethane was added dropwise over 30 minutes. Stirring was continued for another 15 minutes to terminate the reaction. The blowing of fluorine gas was stopped, and the solvent was distilled off to obtain a perfluoro compound of diethyl adamantane dicarboxylate.

[0091] Add 33.7g of sodium borohydride and 500ml of ...

Embodiment 2

[0097] Example 2 (synthesis of perfluoro-1,3-bis(acryloyloxymethyl)adamantane)

[0098] In a four-necked flask with a volume of 1000mL equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, measure 50.0g of the perfluoro-1,3-adamantanedimethanol obtained in Example 1 and dissolve it in 500ml of chloroform middle. 51ml of triethylamine was added thereto, and then 30ml of acryloyl chloride was added dropwise into the flask through the dropping funnel when the temperature in the reaction system did not exceed 25°C. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour. Then, 250 ml of 5% by mass aqueous sodium chloride solution was added, followed by stirring for 10 minutes. The chloroform layer was separated, and then washed twice with 250 ml of a 5% by mass aqueous sodium chloride solution. Next, the chloroform layer was separated, dehydrated with anhydrous magnesium sulfate, and the chloroform was distil...

Embodiment 3

[0105] Example 3 (synthesis of perfluoro-1,3-bis(methacryloyloxymethyl)adamantane)

[0106] In embodiment 2, use 36ml methacryloyl chloride to replace 30ml acryloyl chloride, except that, carry out similarly with embodiment 2, obtain perfluoro-1 shown in the following formula, 3-bis(methacryloyloxymethyl base) adamantane (yield 83%, GC purity 98.7%).

[0107]

[0108] This perfluoro-1,3-bis(methacryloyloxymethyl)adamantane was identified by the same method as in Example 2. Spectral data are shown below.

[0109] 1 H-NMR (500MHz): 1.96(s, 6H), 5.03(s, 4H), 5.69(s, 2H), 6.18(s, 2H)

[0110] 13 C-NMR (125MHz): 18.0, 53.4, 128.0, 134.9, 165.7

[0111] 19 F-NMR (465MHz): -105.1, -113.9, -121.6, -219.4 (α, α, α-trifluorotoluene was used as the reference material, and the value was taken as -64.0)

[0112] GC-MS (EI): 584 (M + , 9.9%), 515 (4.3%), 69 (100%), 41 (42.1%)

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Abstract

To provide a polymerizable group-containing and fluorine-containing adamantane derivative capable of affording a cured product having good heat resistance, good mechanical properties such as mar resistance and a low refractive index, a resin composition containing such a polymerizable group-containing adamantane derivative, and a fluorine-containing adamantane derivative which is useful as a reaction intermediate used for the production of the polymerizable group-containing and fluorine-containing adamantane derivative. Specifically provided are a fluorine-containing adamantane derivative represented by the general formula (I) below, a polymerizable group-containing and fluorine-containing adamantane derivative represented by the general formula (II) below, and a resin composition containing such a polymerizable group-containing and fluorine-containing adamantane derivative. In the formula, R<1> and R<2> are each a hydrogen atom, for example, n is an integer of 0 or more, X<1> is a polymerizable group represented by the formula (III-a), for example, Y is a hydrogen atom, for example, s and t are each an integer of 1 to 15, and u is an integer of 0 to 14, with the proviso that s + t + u = 16.

Description

technical field [0001] The present invention relates to a novel fluorine-containing adamantane derivative, a novel fluorine-containing adamantane derivative containing a polymerizable group, a preparation method thereof, a resin composition containing the above-mentioned fluorine-containing adamantane derivative containing a polymerizable group, and Anti-reflective film. Specifically, it relates to formation of a cured product having good mechanical properties such as heat resistance and scratch resistance and a low refractive index, an antireflection film for a display such as a liquid crystal or an organic EL element, and an antireflection film for a semiconductor resist Fluorine-containing adamantane derivatives containing polymerizable groups and resin compositions thereof, such as film materials, refractive index modulation materials for volume holography, optical fibers, optical waveguides, and various lenses; A fluorine-containing adamantane derivative used as a reacti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/653C07C31/44C07C67/14C07D301/24C07D303/30C08L101/00G02B1/04G02B1/11
CPCC07D301/24C07C31/44C07C2103/74C08F222/1006C08F220/24C07C69/653C07D305/06C07C2603/74C08F222/104C07C33/05
Inventor 冈田保也山根秀树伊藤一松本信昭
Owner IDEMITSU KOSAN CO LTD
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