KR101288499B1 - CYCLIC OLEFFIN-BASED RESIN FILM INCLUDING Si-FILLER AND ELECTRONIC DEVICE USING THE SAME - Google Patents

Abstract

The present invention relates to a cyclic olefin resin film including a cyclic olefin addition polymer and a silicone filler comprising a cyclic olefin monomer and an electronic device using the same, and excellent in mechanical properties and thermal stability.

Silicone filler, cyclic olefin addition polymer, cyclic olefin resin film

Description

Cyclic olefin resin film containing silicon filler and electronic device using the same {CYCLIC OLEFFIN-BASED RESIN FILM INCLUDING Si-FILLER AND ELECTRONIC DEVICE USING THE SAME}

The present invention relates to a cyclic olefin resin film comprising a cyclic olefin addition polymer comprising a cyclic olefin monomer and a silicone filler and an electronic device using the same.

The cyclic olefin resin film formed of the conventional cyclic olefin resin is basically less flexible and easily broken or broken. In addition, it is also thermally unstable, and there are many problems in using it as an electronic device such as a plastic substrate, a matrix, and an optically anisotropic film even in a coefficient of thermal expansion (CTE).

Accordingly, the present invention is a cyclic olefin containing a cyclic olefin monomer in order to solve the problem of the conventional cyclic olefin resin film having low flexibility, hard rigidity easily broken or broken, and thermally unstable to have a high coefficient of thermal expansion. An object of the present invention is to provide a cyclic olefin resin film obtained by mixing an additive polymer and a silicone filler and an electronic device using the same.

The present invention provides a cyclic olefin resin film comprising a cyclic olefin addition polymer comprising a cyclic olefin monomer and a silicone filler represented by the following general formula (1):

[Formula 1]

^{_{(R 30 SiO 1 .5) x}} (R 31 SiO 1 .5) y

In Formula 1,

x and y are integers from 4 to 10,

R ³⁰ and R ³¹ are each independently a C ₁ -C ₁₈ linear or branched alkyl group; C ₂ -C ₁₈ linear or branched alkenyl group; C ₂ -C ₁₈ linear or branched alkynyl group; A cycloalkyl group of C ₄ -C ₈ ; C ₆ -C ₄₀ aryl group or heteroaryl group; An alkoxy group of C ₁ -C ₁₈ ; Alkenyloxy groups of C ₂ -C ₁₈ ; Alkynyl oxy groups of C ₂ -C ₁₈ ; And C ₁ -C ₈ alkyl amine groups.

In addition, the present invention comprises the steps of: a) preparing a composition by adding a silicone-based filler represented by the formula (1) to a cyclic olefin-based addition polymer comprising a cyclic olefin-based monomer; And b) provides a method for producing a cyclic olefin resin film comprising the step of preparing a film using the composition obtained in step a).

In addition, the present invention provides an electronic device comprising the cyclic olefin resin film.

The cyclic olefin resin film according to the present invention includes a silicone filler in the cyclic olefin addition polymer, and has excellent physical properties, and may be manufactured as an electronic device.

Hereinafter, the present invention will be described in detail.

The cyclic olefin resin film according to the present invention is characterized by including a silicone filler with a cyclic olefin addition polymer containing a cyclic olefin monomer.

In this case, the cyclic olefin resin film preferably contains 50 to 99% by weight of the cyclic olefin additive polymer and 1 to 50% by weight of the silicone filler. When the content of the silicone filler exceeds 50% by weight, the toughness of the film is reduced and the film is broken. When the content is less than 1% by weight, the filler does not exhibit the physical properties.

The cyclic olefin resin film according to the present invention fills the empty space of several nanometers to several tens of nanometers in the film due to the structural characteristics of the cyclic olefin-based addition polymer with the silicone-based filler represented by Formula 1 above. In addition to the elimination of fundamentally broken phenomena, it can improve flexibility and thermal stability. Therefore, the cyclic olefin resin film according to the present invention is cheaper and has excellent physical properties, which can be used as a flexible plastic substrate, a compensation film, a protective film, and an optical (anisotropic) film, and can be applied to electronic devices of displays such as LCDs and PDPs. .

It is preferable that the cyclic olefin polymer used in the present invention includes a monomer represented by the following Chemical Formula 2 in order to easily mix with a silicone filler and to obtain a transparent film:

In Formula 2,

p is an integer of 0 to 4,

R1, R2, R3 and R4 are hydrogen; halogen; Linear or branched alkyl of 1 to 20 carbon atoms; Linear or branched alkenyl having 2 to 20 carbon atoms; Linear or branched alkynyl having 2 to 20 carbon atoms; Cycloalkyl having 3 to 12 carbon atoms; Aryl having 6 to 40 carbon atoms; And non-alkyl groups selected from the group consisting of aralkyl having 7 to 15 carbon atoms, or

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로 이루어진 군에서 선택되는 극성 작용기이며; -R ⁸ OR ⁹ , -OR ⁹ , -OC (O) OR ⁹ , -R ⁸ OC (O) OR ⁹ , -C (O) R ⁹ , -R ⁸ C (O) OR ⁹ _, -C (O ) OR ⁹ , -R ⁸ C (O) R ⁹ , -OC (O) R ⁹ , -R ⁸ OC (O) R ⁹ ,-(R ⁸ O) _k -OR ⁹ (k is an integer from 1 to 10) ),-(OR ⁸ ) _k -OR ⁹ (k is an integer from 1 to 10), -C (O) -OC (O) R ⁹ , -R ⁸ C (O) -OC (O) R ⁹ ,- SR ⁹ , -R ⁸ SR ⁹ , -SSR ⁹ , -R ⁸ SSR ⁹ , -S (= O) R ⁹ , -R ⁸ S (= O) R ⁹ , -R ⁸ C (= S) R ⁹ , -R ⁸ C (= S) SR ⁹ , -R ⁸ SO ₂ R ⁹ , -SO ₂ R ⁹ , -R ⁸ OSO ₂ R ⁹ , -R ⁸ SO ₃ R ⁹ , -SO ₃ R ⁹ , -R ⁸ OSO ₃ R ⁹ , -R ⁸ N = C = S, -N = C = S, -NCO, -R ⁸ -NCO, -CN, -R ⁸ CN, -NNC (= S) R ⁹ , -R ⁸ NNC (= S) R ⁹ , -NO ₂ , -R ⁸ NO ₂ ,

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And

A polar functional group selected from the group consisting of;

In the polar functional groups, R ⁸ and R ¹¹ are the same as or different from each other, and each of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaral Linear or branched alkylene having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from K, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkenylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkynylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Cycloalkylene having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Arylene having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aralkylene having 7 to 15 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Alkoxylene unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Or halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy Carbonyloxyylene unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy;

Each of R ⁹ , R ¹² , R ¹³ and R ¹⁴ Are the same as or different from each other, and each hydrogen; halogen; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkyl having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkenyl of 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkynyl having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Cycloalkyl having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aryl having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aralkyl having 7 to 15 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Alkoxy unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Carbonyloxy unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; It is one selected from the group consisting of compounds represented by the following formula (2a), (2b), (2c) and (2d),

(2a)

(2b)

[Chemical Formula 2c]

(2d)

In Chemical Formulas 2a, 2b, 2c, and 2d,

A is a direct bond; Or linear or branched alkylene having 1 to 20 carbon atoms; Carbonyl; Carboxyl; And substituted or unsubstituted arylene or haloarylene having 6 to 40 carbon atoms;

B is oxygen or nitrogen;

X is oxygen or sulfur;

R ¹⁵ is a direct bond; Linear or branched alkylene or halo alkylene having 1 to 20 carbon atoms; Linear or branched alkenylene or haloalkenylene having 2 to 20 carbon atoms; Cycloalkylene or halocycloalkylene having 5 to 12 carbon atoms unsubstituted or substituted with a hydrocarbon; Arylene or haloarylene having 6 to 40 carbon atoms unsubstituted or substituted with hydrocarbon; Aralkylene or haloaralkylene having 7 to 15 carbon atoms unsubstituted or substituted with hydrocarbon; And it is one selected from the group consisting of alkynylene or haloalkynylene having 2 to 20 carbon atoms;

R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , and R ²⁰ Are each independently alkyl or haloalkyl having 1 to 20 carbon atoms; Alkoxy or haloalkoxy having 1 to 20 carbon atoms; Aryloxy or haloaryloxy having 6 to 30 carbon atoms; And aryl or haloaryl having 6 to 40 carbon atoms unsubstituted or substituted with cyano or nitro.

In addition, the cyclic olefin-based addition polymer may further include a cyclic olefin monomer represented by the following formula (3) in addition to the cyclic olefin monomer represented by the formula (2).

In Formula 3,

m and n are each independently an integer of 0 to 2,

R1 "and R2" are each independently halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy Linear or branched alkylene having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkenylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkynylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Cycloalkylene having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Arylene having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aralkylene having 7 to 15 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched haloalkylene having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched haloalkenylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched haloalkynylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Halocycloalkylene having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Haloarylene having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Haloaralkylene having 7 to 15 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; And a non-hydrocarbon polar group including at least one oxygen, nitrogen, phosphorus, sulfur, silicon, or boron, or

R1 "and R2" may be formed of an alkylidene group having 1 to 10 carbon atoms, a saturated or unsaturated ring having 4 to 12 carbon atoms, or an aromatic ring compound having 6 to 24 carbon atoms,

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포함하며; The non-hydrocarbon polar functional group is -R ⁸ OR ⁹ , -OR ⁹ , -OC (O) OR ⁹ , -R ⁸ OC (O) OR ⁹ , -C (O) R ⁹ , -R ⁸ C (O) OR ⁹ _, -C (O) OR ⁹ , -R ⁸ C (O) R ⁹ , -OC (O) R ⁹ , -R ⁸ OC (O) R ⁹ ,-(R ⁸ O) _k -OR ⁹ (k Is an integer from 1 to 10),-(OR ⁸ ) _k -OR ⁹ (k is an integer from 1 to 10), -C (O) -OC (O) R ⁹ , -R ⁸ C (O) -OC ( O) R ⁹ , -SR ⁹ , -R ⁸ SR ⁹ , -SSR ⁹ , -R ⁸ SSR ⁹ , -S (= O) R ⁹ , -R ⁸ S (= O) R ⁹ , -R ⁸ C ( = S) R ⁹ , -R ⁸ C (= S) SR ⁹ , -R ⁸ SO ₃ R ⁹ , -SO ₃ R ⁹ , -R ⁸ N = C = S, -N = C = S, -NCO, -R ⁸ -NCO, -CN, -R ⁸ CN, -NNC (= S) R ⁹ , -R ⁸ NNC (= S) R ⁹ , -NO ₂ , -R ⁸ NO ₂ ,

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And

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In the non-hydrocarbon polar functional group, R ⁸ and R ¹¹ are the same as or different from each other, and each of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy Linear or branched alkylene having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Linear or branched alkenylene having 2 to 20 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Linear or branched alkynylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Cycloalkylene having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Arylene having 6 to 40 carbon atoms, which is unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Aralkylene having 7 to 15 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Alkoxylene unsubstituted or substituted with one or more substituents selected from the group; Or halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and Carbonyloxyylene unsubstituted or substituted with one or more substituents selected from siloxy; When two or more R ⁸ or R ¹¹ are present, they are the same as or different from each other;

R ⁹ , R ¹² , R ¹³ and R ¹⁴ are the same as or different from each other, and are each hydrogen; halogen; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Linear or branched alkyl having 1 to 20 carbon atoms, unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Linear or branched alkenyl having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Linear or branched alkynyl having 2 to 20 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and Cycloalkyl having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Aryl having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Aralkyl having 7 to 15 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Alkoxy unsubstituted or substituted with one or more substituents selected from the group; Or halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and Carbonyloxy unsubstituted or substituted with one or more substituents selected from siloxy; When two or more R ^{12 's} are present, they are the same or different from each other.

Looking at the definition of the above-described substituents in detail as follows.

"Alkyl" means a straight or branched chain saturated monovalent hydrocarbon moiety of 1 to 20, preferably 1 to 10, more preferably 1 to 6 carbon atoms. Alkyl groups may be optionally substituted by one or more halogen substituents. Examples of alkyl groups are methyl, ethyl, propyl, 2-propyl, n-butyl, iso-butyl, tert-butyl, pentyl, hexyl, dodecyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl , Dichloromethyl, trichloromethyl, iodomethyl, bromomethyl and the like.

"Alkenyl" means a straight or branched chain monovalent hydrocarbon moiety of 2 to 20, preferably 2 to 10, more preferably 2 to 6 carbon atoms comprising at least one carbon-carbon double bond. . Alkenyl groups may be bonded through a carbon atom comprising a carbon-carbon double bond and / or through a saturated carbon atom. Alkenyl groups may be optionally substituted by one or more halogen substituents. Examples of the alkenyl group include ethenyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, pentenyl, 5-hexenyl and dodecenyl.

"Cycloalkyl" means a saturated or unsaturated non-aromatic monovalent monocyclic, bicyclic or tricyclic hydrocarbon moiety of 3 to 12 ring carbons and may be optionally substituted by one or more halogen substituents. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cyclooctyl, decahydronaphthalenyl, adamantyl, norbornyl (ie bicyclo [2. 2.1] Hept-5-enyl), and the like.

"Aryl" means a monovalent monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety having 6 to 40, preferably 6 to 12 ring atoms, which may be optionally substituted by one or more halogen substituents. . The aromatic portion of the aryl group contains only carbon atoms. Examples of aryl groups include phenyl, naphthalenyl and fluorenyl.

"Alkynyl" means a monovalent hydrocarbon moiety of 2 to 20 carbon atoms, preferably 2 to 10, more preferably 2 to 6, straight or branched chains containing at least one carbon-carbon triple bond. do. Alkynyl groups may be bonded through a carbon atom comprising a carbon-carbon triple bond or through a saturated carbon atom. Alkynyl groups may be optionally substituted by one or more halogen substituents. For example, ethynyl, propynyl and the like.

"Alkylene" means a straight or branched chain saturated divalent hydrocarbon moiety of 1 to 20, preferably 1 to 10, more preferably 1 to 6 carbon atoms. Alkylene groups may be optionally substituted by one or more halogen substituents. Examples of the alkyl group include methylene, ethylene, propylene, butylene, hexylene and the like.

"Alkenylene" means a straight or branched chain divalent hydrocarbon moiety of 2 to 20, preferably 2 to 10, more preferably 2 to 6 carbon atoms containing at least one carbon-carbon double bond. do. The alkenylene group may be bonded through a carbon atom containing a carbon-carbon double bond and / or through a saturated carbon atom. Alkenylene groups may be optionally substituted by one or more halogen substituents.

"Cycloalkylene" means a saturated or unsaturated non-aromatic divalent monocyclic, bicyclic or tricyclic hydrocarbon moiety of 3 to 12 ring carbons and may be optionally substituted by one or more halogen substituents. Examples thereof include cyclopropylene and cyclobutylene.

"Arylene" means a divalent monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety having 6 to 40, preferably 6 to 12 ring atoms, which may be optionally substituted by one or more halogen substituents. have. The aromatic portion of the aryl group contains only carbon atoms. Examples of the arylene group include phenylene and the like.

"Aralkylene" means a divalent moiety wherein at least one hydrogen atom of the alkyl group as defined above is substituted with an aryl group, and may be optionally substituted by one or more halogen substituents. For example, benzylene and the like.

"Alkynylene" refers to a straight or branched divalent hydrocarbon moiety of 2 to 20 carbon atoms, preferably 2 to 10, more preferably 2 to 6 carbon atoms, including one or more carbon-carbon triple bonds do. The alkynylene group may be bonded through a carbon atom containing a carbon-carbon triple bond or through a saturated carbon atom. Alkynylene groups may be optionally substituted by one or more halogen substituents. For example, ethynylene or propynylene.

"Binding" refers to a site joined by a simple bond without any substituents inserted.

In the present invention, the cyclic olefin based addition polymer may be prepared by a method known in the art.

The cyclic olefin-based addition polymer is preferably polymerized by containing 1 to 99.9 mol% of the monomer represented by Formula 2 and 0.1 to 99 mol% of the monomer represented by Formula 3.

As described above, the cyclic olefin addition polymer polymerized by mixing the monomer represented by the formula (2) and the monomer represented by the formula (3) includes the following formula (4).

In Chemical Formula 4,

s and t are integers from 50 to 5,000,

n, m, p, R1, R2, R3, R4, R1 "and R2" are the same as defined in Chemical Formulas 2 and 3.

The cyclic olefin resin film according to the present invention is formed by adding a silicone filler to a cyclic olefin addition polymer containing a cyclic olefin monomer. Specifically, after the silicone filler is added to the cyclic olefin additive polymer, it is dissolved in a solvent and molded into a film. The method for molding into the film may use a technique known in the art, for example, by coating and drying a mixed solution of the cyclic olefin-based addition polymer and the silicone filler on a substrate, it can be prepared as a cyclic olefin resin film. .

The cyclic olefin resin film may be made by a solution casting method, and the solvent used may include toluene, chloroform, dichloromethane, xylene, ethyl acetate, and the like. The concentration of the polymer and the filler is adjusted to 10 to 20 wt% of the total solution, and then coated on a glass plate and dried at room temperature for 1 to 3 hours. During this process, the environment is controlled to maintain 50 ± 5% humidity and 20 ~ 23 ℃. And it is further dried at 100-150 degreeC for 1-3 hours.

The cyclic olefin resin film according to the present invention is applied to an electronic device such as a plastic substrate including an LCD substrate, a flexible substrate, or a display device such as an LCD or a PDP including a compensation film, a protective film, an electromagnetic shielding filter, an optical film, or the like. Can be used.

Hereinafter, the present invention will be described in detail through embodiments of the present invention. However, embodiments of the present invention may be modified in various forms, the scope of the present invention should not be construed in a way that is limited by the embodiments described below. Embodiments of the present invention are provided to more fully explain the present invention to those skilled in the art.

 Preparation Examples 1 to 3: Homopolymer Synthesis

≪ Preparation Example 1 &

5-norbornene-2-methyl acetate (30 g, 0.18 mol) was mixed with toluene (100 mL) and stirred for 30 minutes under nitrogen atmosphere. After stirring, the temperature was raised to 90 ° C., Pd (acetate) ₂ (2.7 mg, 12 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (24.2 mg, 25.2 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, precipitated in ethanol to obtain a white powder. (Yield 93%, Molecular Weight (Mw): 340k (PDI = 1.83)).

≪ Preparation Example 2 &

5-norbornene-2-carboxylic acid methyl ester (30 g, 0.197 mol) was mixed with toluene (100 mL) and stirred for 30 minutes under nitrogen atmosphere. After stirring, the temperature was raised to 90 ° C. and Pd (acetate) ₂ (4.4 mg, 19.7 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (39.7 mg, 41.4 µmol) A mixed solution was added to the above reaction solution. After stirring at 90 ° C. for about 5 hours, precipitated in ethanol to obtain a white powder. (Yield 65%, Molecular Weight (Mw): 170k (PDI = 2.35)).

≪ Preparation Example 3 &

5-norbornene-2-triethethoxysilane (30 g, 0.117 mol) was mixed with toluene (100 mL) and stirred for 30 minutes under nitrogen atmosphere. After stirring, the temperature was raised to 90 ° C. and Pd (acetate) ₂ (1.75 mg, 7.8 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (15.7 mg, 16.4 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, precipitated in ethanol to obtain a white powder. (Yield 63%, Molecular Weight (Mw): 640k (PDI = 2.22)).

Preparation Examples 4 to 14 Copolymer Synthesis

≪ Preparation Example 4 &

5-norbornene-2-triethethoxysilane (1 g, 3.9 mmol) and 5-norbornene-2-carboxylic acid methyl ester (5.34 g, 35.1 mmol) were mixed with toluene (63 mL) under nitrogen atmosphere. Stirred for 30 minutes. After stirring, the temperature was raised to 90 ° C., Pd (acetate) ₂ (0.87 mg, 3.9 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (7.9 mg, 81.9 μmol) was added to the reaction solution. After stirring for about 5 hours at 90 ℃ precipitated in ethanol to give a white powder. (Yield 27%, Molecular Weight (Mw): 93k (PDI = 1.81)).

≪ Production Example 5 &

5-norbornene-2-triethethoxysilane (3 g, 11.7 mmol) and 5-norbornene-2-carboxylic acid methyl ester (4.15 g, 27.3 mmol) were mixed with toluene (72 mL) under nitrogen atmosphere. Stirred for 30 minutes. After stirring, the temperature was raised to 90 ° C., Pd (acetate) ₂ (0.87 mg, 3.9 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (7.9 mg, 81.9 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, it was precipitated in ethanol to obtain a white powder. (Yield 44%, Molecular Weight (Mw): 176 k (PDI = 2.01)).

≪ Production Example 6 &

5-norbornene-2-triethoxysilane (5 g, 19.5 mmol) and 5-norbornene-2-carboxylic acid methyl ester (2.97 g, 19.5 mmol) were mixed with toluene (80 mL) to obtain nitrogen. Stir under air for 30 minutes. After stirring, the temperature was raised to 90 ° C., Pd (acetate) ₂ (0.87 mg, 3.9 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (7.9 mg, 81.9 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, it was precipitated in ethanol to obtain a white powder. (Yield 54%, Molecular Weight (Mw): 283 k (PDI = 2.79)).

≪ Production Example 7 >

5-norbornene-2-triethethoxysilane (7 g, 27.3 mmol) and 5-norbornene-2-carboxylic acid methyl ester (1.78 g, 11.7 mmol) were mixed with toluene (88 mL) under nitrogen atmosphere. Stirred for 30 minutes. After stirring, the temperature was raised to 90 ° C., Pd (acetate) ₂ (0.87 mg, 3.9 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (7.9 mg, 81.9 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, it was precipitated in ethanol to obtain a white powder. (Yield 86%, molecular weight (Mw): 502 k (PDI = 3.18)).

≪ Production Example 8 &

5-norbornene-2-triethethoxysilane (8 g, 31.2 mmol) and 5-norbornene-2-carboxylic acid methyl ester (1.19 g, 7.8 mmol) were mixed with toluene (92 mL) under nitrogen atmosphere. Stirred for 30 minutes. After stirring, the temperature was raised to 90 ° C., and Pd (acetate) ₂ (0.87 mg, 3.9 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (7.9 mg, 81.9 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, precipitated in ethanol to obtain a white powder. (Yield 60%, Molecular Weight (Mw): 863 k (PDI = 2.31)).

≪ Production Example 9 &

Toluene (63 ml) with 5-norbornene-2-triethethoxysilane (7 g, 27.3 mmol) and 5-norbornene-2-methyl acetate (1.95 g, 11.7 mmol, endo / exo = 55/45) The mixture was stirred for 30 minutes under nitrogen atmosphere. After stirring, the temperature was raised to 90 ° C., Pd (acetate) ₂ (0.87 mg, 3.9 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (7.9 mg, 81.9 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, precipitated in ethanol to obtain a white powder. (Yield 51%, Molecular Weight (Mw): 637 k (PDI = 2.09)).

≪ Production Example 10 &

Toluene (65 mL) with 5-norbornene-2-triethethoxysilane (8 g, 31.2 mmol) and 5-norbornene-2-methyl acetate (1.25 g, 7.5 mmol, endo / exo = 55/45) The mixture was stirred for 30 minutes under nitrogen atmosphere. After stirring, the temperature was raised to 90 ° C., Pd (acetate) ₂ (0.87 mg, 3.9 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (7.9 mg, 81.9 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, precipitated in ethanol to obtain a white powder. (Yield 52%, Molecular Weight (Mw): 549 k (PDI = 2.14)).

Production Example 11

Toluene (48 mL) with 5-norbornene-2-triethethoxysilane (1 g, 3.9 mmol) and 5-norbornene-2-methyl acetate (5.83 g, 35.1 mmol, endo / exo = 55/45) The mixture was stirred for 30 minutes under nitrogen atmosphere. After stirring, the temperature was raised to 90 ° C., Pd (acetate) ₂ (0.87 mg, 3.9 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (7.9 mg, 81.9 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, precipitated in ethanol to obtain a white powder. (Yield 56%, Molecular Weight (Mw): 623 k (PDI = 2.2)).

≪ Production Example 12 &

5-norbornene-2-triethethoxysilane (2 g, 7.8 mmol) and 5-norbornene-2-methyl acetate (5.2 g, 31.2 mmol, endo / exo = 55/45) toluene (50 mL) The mixture was stirred for 30 minutes under nitrogen atmosphere. After stirring, the temperature was raised to 90 ° C., Pd (acetate) ₂ (0.87 mg, 3.9 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (7.9 mg, 81.9 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, precipitated in ethanol to obtain a white powder. (Yield 58%, Molecular Weight (Mw): 523 k (PDI = 2.57)).

Production Example 13

Toluene (53 mL) with 5-norbornene-2-triethethoxysilane (3 g, 11.7 mmol) and 5-norbornene-2-methyl acetate (4.53 g, 27.3 mmol, endo / exo = 55/45) The mixture was stirred for 30 minutes under nitrogen atmosphere. After stirring, the temperature was raised to 90 ° C., and Pd (acetate) ₂ (1.74 mg, 7.8 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (15.8 mg, 163.8 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, precipitated in ethanol to obtain a white powder. (Yield 81%, Molecular Weight (Mw): 401 k (PDI = 4.15)).

Production Example 14

Toluene (58 ml) with 5-norbornene-2-triethoxysilane (5 g, 19.5 mmol) and 5-norbornene-2-methyl acetate (3.24 g, 19.5 mmol, endo / exo = 55/45) The mixture was stirred for 30 minutes under nitrogen atmosphere. After stirring, the temperature was raised to 90 ° C. and Pd (acetate) ₂ (1.74 mg, 7.8 μmol) and tris (cyclohexane) phosphonium-tetrakis (pentafluorophenyl) borate salt dissolved in MC (1 mL) (15.8 mg, 163.8 μmol) was added to the reaction solution. After stirring at 90 ° C. for about 5 hours, precipitated in ethanol to obtain a white powder. (Yield 73%, Molecular Weight (Mw): 408 k (PDI = 2.39)).

Preparation Examples 15 to 20 Synthesis of Silicone Filler

Production Example 15

Phenyltrimethoxysilane (20 g, 0.1 mol) was mixed with formic acid (13.8 g, 0.3 mol) and stirred at 50 ° C. for 24 hours. After the reaction, the temperature was lowered to room temperature, and the remaining formic acid was removed under reduced pressure.

Production Example 16

Phenyltrimethoxysilane (20 g, 0.1 mol) was mixed with formic acid (13.8 g, 0.3 mol) and H ₂ O (0.95 g, 0.0525 mol), followed by stirring at 50 ° C. for 24 hours. After the reaction, the temperature was lowered to room temperature, and the remaining water and formic acid were removed under reduced pressure.

Production Example 17

Methyltrimethoxysilane (10 g, 0.07 mol) was mixed with formic acid (9.66 g, 0.21 mol) and stirred at 50 ° C. for 24 hours. After the reaction, the temperature was lowered to room temperature, and the remaining formic acid was removed under reduced pressure.

Production Example 18

Methyltrimethoxysilane (10 g, 0.07 mol) was mixed with formic acid (9.66 g, 0.21 mol) and H ₂ O (1.32 g, 0.074 mol), followed by stirring at 50 ° C. for 24 hours. After the reaction, the temperature was lowered to room temperature, and the remaining water and formic acid were removed under reduced pressure.

Production Example 19

Cyclohexyltrimethoxysilane (10 g, 0.0492 mol) was mixed with formic acid (6.79 g, 0.15 mol) and stirred at 50 ° C. for 24 hours. After the reaction, the temperature was lowered to room temperature, and the remaining formic acid was removed under reduced pressure.

Production Example 20

Cyclohexyltrimethoxysilane (10 g, 0.0492 mol) was mixed with formic acid (6.79 g, 0.15 mol) and H ₂ O (0.93 g, 0.0517 mol), followed by stirring at 50 ° C. for 24 hours. After the reaction, the temperature was lowered to room temperature, and the remaining water and formic acid were removed under reduced pressure.

<Examples 1-15> cyclic olefin resin film manufacture

5 g of the mixed amount of each of the additive polymer and the silicone filler obtained in the above preparation in the content ratio as shown in Table 1 was dissolved in toluene at 13% by weight, followed by shaking with a shaker for 10 hours. The mixed solution was sprinkled with about 5 ml well on a glass plate having a clean surface, and then pushed out with a blade placed 100 μm above the glass plate. The film was aging on the surface at room temperature for about 1 hour and then dried in an oven at 100 ° C. for 1 hour. After drying, the film was removed from the glass plate to obtain a transparent cyclic olefin resin film.

&Lt; Comparative Examples 1 to 4 >

A cyclic olefin resin film was prepared in the same manner as in Examples 1 to 15, except that a silicone filler was added.

In order to measure the coefficient of thermal expansion (CTE) of the cyclic olefin resin films obtained in the above Examples and Comparative Examples, the film was cut into 2 cm × 5 cm size, and the CTE was confirmed through TMA.

Entry Polymer (wt%) Filler (wt%) CTE (PPM) Example 1 Preparation Example 1 (90) Preparation Example 15 (10) 108 Example 2 Preparation Example 1 (70) Preparation Example 15 (30) 85 Example 3 Preparation Example 1 (50) Preparation Example 15 (50) 42 Example 4 Preparation Example 1 (90) Preparation Example 17 (10) 99 Example 5 Preparation Example 1 (70) Preparation Example 17 (30) 73 Example 6 Preparation Example 1 (50) Preparation Example 17 (50) 35 Example 7 Preparation Example 3 (90) Preparation Example 15 (10) 123 Example 8 Preparation Example 3 (70) Preparation Example 15 (30) 77 Example 9 Preparation Example 3 (50) Preparation Example 15 (50) 53 Example 10 Preparation Example 6 (90) Preparation Example 15 (10) 127 Example 11 Preparation Example 6 (70) Preparation Example 15 (30) 100 Example 12 Preparation Example 6 (50) Preparation Example 15 (50) 65 Example 13 Preparation 14 (70) Preparation Example 15 (30) 113 Example 14 Preparation 14 (70) Preparation Example 19 (30) 95 Example 15 Preparation Example 14 (50) Preparation Example 19 (50) 58 Comparative Example 1 Preparation Example 1 (100) Preparation Example 15 (0) 110 Comparative Example 2 Preparation Example 3 (100) Preparation Example 15 (0) 143 Comparative Example 3 Preparation Example 6 (100) Preparation Example 15 (0) 135 Comparative Example 4 Preparation 14 (100) Preparation Example 15 (0) 167

Looking at the thermal expansion coefficient measurement results of Examples and Comparative Examples of Table 1, it can be seen that the film according to the embodiment containing the silicon-based filler of the present invention is low thermal expansion coefficient is stable thermally. However, it can be seen that the film according to the comparative example, which does not contain the silicone filler of the present invention, has a high thermal expansion coefficient and is thermally unstable.

Claims (9)

It includes a repeating unit derived from the monomer represented by the formula (2) A cyclic olefin resin film containing a cyclic olefin addition polymer and a silicone filler represented by the following formula (1): [Formula 1] (R ³⁰ SiO _1.5 ) x (R ³¹ SiO _1.5 ) y In Formula 1, x and y are integers from 4 to 10, R ³⁰ and R ³¹ are each independently a C ₁ -C ₁₈ linear or branched alkyl group, C ₂ -C ₁₈ linear or branched alkenyl group, C ₂ -C ₁₈ linear or branched alkynyl group, C ₄ -C ₈ cycloalkyl group, C ₁ -C ₄₀ aryl group or heteroaryl group, C ₁ -C ₁₈ alkoxy group, C ₂ -C ₁₈ alkenyl oxy group, C ₂ -C ₁₈ alkynyl oxy group And it is one selected from the group consisting of C ₁ -C ₈ alkyl amine group,  [Formula 2]

In Formula 2, p is an integer of 0 to 4, R1, R2, R3 and R4 are hydrogen; halogen; Linear or branched alkyl of 1 to 20 carbon atoms; Linear or branched alkenyl having 2 to 20 carbon atoms; Linear or branched alkynyl having 2 to 20 carbon atoms; Cycloalkyl having 3 to 12 carbon atoms; Aryl having 6 to 40 carbon atoms; And non-alkyl groups selected from the group consisting of aralkyl having 7 to 15 carbon atoms, or -R ⁸ OR ⁹ , -OR ⁹ , -OC (O) OR ⁹ , -R ⁸ OC (O) OR ⁹ , -C (O) R ⁹ , -R ⁸ C (O) OR ⁹ _, -C (O ) OR ⁹ , -R ⁸ C (O) R ⁹ , -OC (O) R ⁹ , -R ⁸ OC (O) R ⁹ ,-(R ⁸ O) _k -OR ⁹ (k is an integer from 1 to 10) ),-(OR ⁸ ) _k -OR ⁹ (k is an integer from 1 to 10), -C (O) -OC (O) R ⁹ , -R ⁸ C (O) -OC (O) R ⁹ ,- SR ⁹ , -R ⁸ SR ⁹ , -SSR ⁹ , -R ⁸ SSR ⁹ , -S (= O) R ⁹ , -R ⁸ S (= O) R ⁹ , -R ⁸ C (= S) R ⁹ , -R ⁸ C (= S) SR ⁹ , -R ⁸ SO ₂ R ⁹ , -SO ₂ R ⁹ , -R ⁸ OSO ₂ R ⁹ , -R ⁸ SO ₃ R ⁹ , -SO ₃ R ⁹ , -R ⁸ OSO ₃ R ⁹ , -R ⁸ N = C = S, -N = C = S, -NCO, -R ⁸ -NCO, -CN, -R ⁸ CN, -NNC (= S) R ⁹ , -R ⁸ NNC (= S) R ⁹ , -NO ₂ , -R ⁸ NO ₂ ,

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A polar functional group selected from the group consisting of; In the polar functional groups, R ⁸ and R ¹¹ are the same as or different from each other, and each of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl Linear or branched alkylene having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkenylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkynylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Cycloalkylene having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Arylene having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aralkylene having 7 to 15 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Alkoxylene unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Or halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy Carbonyloxyylene unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Each of R ⁹ , R ¹² , R ¹³ and R ¹⁴ is the same or different from each other, and each hydrogen; halogen; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkyl having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkenyl of 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkynyl having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Cycloalkyl having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aryl having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aralkyl having 7 to 15 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Alkoxy unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Carbonyloxy unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; It is one selected from the group consisting of compounds represented by the following formula (2a), (2b), (2c) and (2d), (2a)

[Formula 2b]

[Formula 2c]

(2d)

In Chemical Formulas 2a, 2b, 2c, and 2d, A is a direct bond; Or linear or branched alkylene having 1 to 20 carbon atoms; Carbonyl; Carboxyl; And substituted or unsubstituted arylene or haloarylene having 6 to 40 carbon atoms; B is oxygen or nitrogen; X is oxygen or sulfur; R ¹⁵ is a direct bond; Linear or branched alkylene or halo alkylene having 1 to 20 carbon atoms; Linear or branched alkenylene or haloalkenylene having 2 to 20 carbon atoms; Cycloalkylene or halocycloalkylene having 5 to 12 carbon atoms unsubstituted or substituted with a hydrocarbon; Arylene or haloarylene having 6 to 40 carbon atoms unsubstituted or substituted with hydrocarbon; Aralkylene or haloaralkylene having 7 to 15 carbon atoms unsubstituted or substituted with hydrocarbon; Alkynylene or haloalkynylene having 2 to 20 carbon atoms; R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , and R ²⁰ Are each independently alkyl or haloalkyl having 1 to 20 carbon atoms; Alkoxy or haloalkoxy having 1 to 20 carbon atoms; Aryloxy or haloaryloxy having 6 to 30 carbon atoms; And aryl or haloaryl having 6 to 40 carbon atoms unsubstituted or substituted with cyano or nitro. The cyclic olefin resin film of claim 1, wherein the cyclic olefin resin film comprises 50 to 99 wt% of the cyclic olefin addition polymer and 1 to 50 wt% of the silicone filler represented by Chemical Formula 1. delete The cyclic olefin resin film of claim 1, wherein the cyclic olefin addition polymer further comprises a monomer represented by Formula 3 below: (3)

In Formula 3, m and n are each independently an integer of 0 to 2, R 1 ″ and R 2 ″ each independently halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, Linear or branched alkylene having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkenylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkynylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Cycloalkylene having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Arylene having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aralkylene having 7 to 15 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched haloalkylene having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched haloalkenylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched haloalkynylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Halocycloalkylene having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Haloarylene having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Haloaralkylene having 7 to 15 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Or -R ⁸ OR ⁹ , -OR ⁹ , -OC (O) OR ⁹ , -R ⁸ OC (O) OR ⁹ , -C (O) comprising at least one oxygen, nitrogen, phosphorus, sulfur, silicon or boron ) R ⁹ , -R ⁸ C (O) OR ⁹ _, -C (O) OR ⁹ , -R ⁸ C (O) R ⁹ , -OC (O) R ⁹ , -R ⁸ OC (O) R ⁹ , -(R ⁸ O) _k -OR ⁹ (k is an integer from 1 to 10),-(OR ⁸ ) _k -OR ⁹ (k is an integer from 1 to 10), -C (O) -OC (O) R ⁹ , -R ⁸ C (O) -OC (O) R ⁹ , -SR ⁹ , -R ⁸ SR ⁹ , -SSR ⁹ , -R ⁸ SSR ⁹ , -S (= O) R ⁹ , -R ⁸ S (= O) R ⁹ , -R ⁸ C (= S) R ⁹ , -R ⁸ C (= S) SR ⁹ , -R ⁸ SO ₃ R ⁹ , -SO ₃ R ⁹ , -R ⁸ N = C = S, -N = C = S, -NCO, -R ⁸ -NCO, -CN, -R ⁸ CN, -NNC (= S) R ⁹ , -R ⁸ NNC (= S) R ⁹ , -NO ₂ , -R ⁸ NO ₂ ,

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And

Non-hydrocarbon polar group selected from the group consisting of; or, Or R1 "and R2" are connected to each other to form a compound selected from the group consisting of an alkylidene group having 1 to 10 carbon atoms, a saturated or unsaturated ring having 4 to 12 carbon atoms, and an aromatic cyclic compound having 6 to 24 carbon atoms, In the non-hydrocarbon polar functional group, R ⁸ and R ¹¹ are the same as or different from each other, and each of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy Linear or branched alkylene having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Linear or branched alkenylene having 2 to 20 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Linear or branched alkynylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Cycloalkylene having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Arylene having 6 to 40 carbon atoms, which is unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Aralkylene having 7 to 15 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Alkoxylene unsubstituted or substituted with one or more substituents selected from the group; Or halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and Carbonyloxyylene unsubstituted or substituted with one or more substituents selected from siloxy; When two or more R ⁸ or R ¹¹ are present, they are the same as or different from each other; R ⁹ , R ¹² , R ¹³ and R ¹⁴ are the same as or different from each other, and are each hydrogen; halogen; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Linear or branched alkyl having 1 to 20 carbon atoms, unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Linear or branched alkenyl having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Linear or branched alkynyl having 3 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Cycloalkyl having 3 to 12 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Aryl having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Aralkyl having 7 to 15 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxane Alkoxy unsubstituted or substituted with one or more substituents selected from the group; Or halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, aralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and Carbonyloxy unsubstituted or substituted with one or more substituents selected from siloxy; When two or more R ^{12 's} are present, they are the same or different from each other. The cyclic olefin resin film according to claim 4, wherein the cyclic olefin addition polymer is an addition polymer synthesized from 1 to 99.9 mol% of the monomer represented by Formula 2 and 0.1 to 99 mol% of the monomer represented by Formula 3. . The cyclic olefin resin film of claim 4, wherein the cyclic olefin addition polymer is a polymer comprising the following general formula (4): [Formula 4]

In Chemical Formula 4, s and t are integers from 50 to 5,000, n, m, p, R1, R2, R3, R4 _, R1 "and R2" are the same as defined in Chemical Formulas 2 and 3. a) preparing a composition by adding a silicone-based filler represented by Formula 1 to a cyclic olefin-based addition polymer comprising a repeating unit derived from a monomer represented by Formula 2; And b) a method of producing a cyclic olefin resin film comprising the step of preparing a film using the composition obtained in step a): [Formula 1] (R ³⁰ SiO _1.5 ) x (R ³¹ SiO _1.5 ) y In Formula 1, x and y are integers from 4 to 10, R ³⁰ and R ³¹ are each independently a C ₁ -C ₁₈ linear or branched alkyl group, C ₂ -C ₁₈ linear or branched alkenyl group, C ₂ -C ₁₈ linear or branched alkynyl group, C ₄ -C ₈ cycloalkyl group, C ₁ -C ₄₀ aryl group or heteroaryl group, C ₁ -C ₁₈ alkoxy group, C ₂ -C ₁₈ alkenyl oxy group, C ₂ -C ₁₈ alkynyl oxy group And it is one selected from the group consisting of C ₁ -C ₈ alkyl amine group,  [Formula 2]

In Formula 2, p is an integer of 0 to 4, R1, R2, R3 and R4 are hydrogen; halogen; Linear or branched alkyl of 1 to 20 carbon atoms; Linear or branched alkenyl having 2 to 20 carbon atoms; Linear or branched alkynyl having 2 to 20 carbon atoms; Cycloalkyl having 3 to 12 carbon atoms; Aryl having 6 to 40 carbon atoms; And non-alkyl groups selected from the group consisting of aralkyl having 7 to 15 carbon atoms, or -R ⁸ OR ⁹ , -OR ⁹ , -OC (O) OR ⁹ , -R ⁸ OC (O) OR ⁹ , -C (O) R ⁹ , -R ⁸ C (O) OR ⁹ _, -C (O ) OR ⁹ , -R ⁸ C (O) R ⁹ , -OC (O) R ⁹ , -R ⁸ OC (O) R ⁹ ,-(R ⁸ O) _k -OR ⁹ (k is an integer from 1 to 10) ),-(OR ⁸ ) _k -OR ⁹ (k is an integer from 1 to 10), -C (O) -OC (O) R ⁹ , -R ⁸ C (O) -OC (O) R ⁹ ,- SR ⁹ , -R ⁸ SR ⁹ , -SSR ⁹ , -R ⁸ SSR ⁹ , -S (= O) R ⁹ , -R ⁸ S (= O) R ⁹ , -R ⁸ C (= S) R ⁹ , -R ⁸ C (= S) SR ⁹ , -R ⁸ SO ₂ R ⁹ , -SO ₂ R ⁹ , -R ⁸ OSO ₂ R ⁹ , -R ⁸ SO ₃ R ⁹ , -SO ₃ R ⁹ , -R ⁸ OSO ₃ R ⁹ , -R ⁸ N = C = S, -N = C = S, -NCO, -R ⁸ -NCO, -CN, -R ⁸ CN, -NNC (= S) R ⁹ , -R ⁸ NNC (= S) R ⁹ , -NO ₂ , -R ⁸ NO ₂ ,

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A polar functional group selected from the group consisting of; In the polar functional groups, R ⁸ and R ¹¹ are the same as or different from each other, and each of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl Linear or branched alkylene having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkenylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkynylene having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Cycloalkylene having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Arylene having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aralkylene having 7 to 15 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Alkoxylene unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Or halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy Carbonyloxyylene unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Each of R ⁹ , R ¹² , R ¹³ and R ¹⁴ is the same or different from each other, and each hydrogen; halogen; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkyl having 1 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkenyl of 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Linear or branched alkynyl having 2 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Cycloalkyl having 3 to 12 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aryl having 6 to 40 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Aralkyl having 7 to 15 carbon atoms unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Alkoxy unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; Halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, Carbonyloxy unsubstituted or substituted with one or more substituents selected from haloaryloxy, silyl, and siloxy; It is one selected from the group consisting of compounds represented by the following formula (2a), (2b), (2c) and (2d), (2a)

[Formula 2b]

[Formula 2c]

(2d)

In Chemical Formulas 2a, 2b, 2c, and 2d, A is a direct bond; Or linear or branched alkylene having 1 to 20 carbon atoms; Carbonyl; Carboxyl; And substituted or unsubstituted arylene or haloarylene having 6 to 40 carbon atoms; B is oxygen or nitrogen; X is oxygen or sulfur; R ¹⁵ is a direct bond; Linear or branched alkylene or halo alkylene having 1 to 20 carbon atoms; Linear or branched alkenylene or haloalkenylene having 2 to 20 carbon atoms; Cycloalkylene or halocycloalkylene having 5 to 12 carbon atoms unsubstituted or substituted with a hydrocarbon; Arylene or haloarylene having 6 to 40 carbon atoms unsubstituted or substituted with hydrocarbon; Aralkylene or haloaralkylene having 7 to 15 carbon atoms unsubstituted or substituted with hydrocarbon; Alkynylene or haloalkynylene having 2 to 20 carbon atoms; R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , and R ²⁰ Are each independently alkyl or haloalkyl having 1 to 20 carbon atoms; Alkoxy or haloalkoxy having 1 to 20 carbon atoms; Aryloxy or haloaryloxy having 6 to 30 carbon atoms; And aryl or haloaryl having 6 to 40 carbon atoms unsubstituted or substituted with cyano or nitro. An electronic device comprising the cyclic olefin resin film of any one of claims 1 to 2 and 4 to 6. The electronic device of claim 8, wherein the cyclic olefin resin film serves as a plastic substrate, a compensation film, a protective film, an electromagnetic shielding filter, or an optical (anisotropic) film.