JP2017132785A - Novel compound, and polymer, curing agent and crosslinking agent prepared therewith - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel compound designed to effectively utilize the structure of a dibenzo [g, p] chrysene skeleton.SOLUTION: The present invention provides a compound of formula (C1). At least one group of R-Ris represented by -OR, and Rof at least one group thereof is a C2-C12 group having a polymerizable unsaturated bond at a terminal. R-Rother than the at least one group independently represent H (a hydrogen atom), X (a halogen atom) or a monovalent group.SELECTED DRAWING: None

Description

  The present invention relates to a novel compound and a polymer using the same, and more particularly to a novel compound having a dibenzo [g, p] chrysene skeleton and a polymer using the same.

  Conventionally, a compound group having a dibenzo [g, p] chrysene skeleton has attracted attention as a material exhibiting organic electroluminescence characteristics. And the various dibenzo [g, p] chrysene compound groups substituted by the bulky functional group which has an aromatic ring structure are indicated by the following patent documents 1-4.

JP 2002-237384 A JP 2009-292807 A JP 2004-182737 A WO09 / 107549 pamphlet

However, the synthesis of compounds utilizing the structure of the dibenzo [g, p] chrysene skeleton has not progressed. Accordingly, the present inventors have attempted to synthesize novel compounds that take advantage of the characteristics of the dibenzo [g, p] chrysene skeleton.
The present invention has been made in view of the above situation, and provides a novel compound and a polymer using the same designed to make more effective use of the structure of a dibenzo [g, p] chrysene skeleton. With the goal.

前記式（Ｃ１）中、Ｒ^１〜Ｒ^４のうちの少なくとも１つの基が−ＯＲ^５で表され、
前記少なくとも１つの基のＲ^５は、末端に重合性不飽和結合を有する炭素数２〜１２の基であり、
前記少なくとも１つの基以外のＲ^１〜Ｒ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。 In order to solve the above problems, the compound according to claim 1 is represented by the following formula (C1).

In the formula (C1), at least one group of R ^{1 to} R ⁴ is represented by —OR ⁵ ,
R ⁵ of the at least one group is a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at a terminal;
R ^{1 to} R ⁴ other than the at least one group are each independently H (hydrogen atom), X (halogen atom) or a monovalent group.

The compound according to claim 2 is characterized in that, in the compound according to claim 1, R ⁵ contains -CO-.

The compound according to claim 3 is the compound according to claim 2, wherein the R ⁵ is represented by the following formula (C2).
^{_{-CO- (CH 2) n -C (}} R 6) = CH 2 ··· (C2)
R ⁶ represents H (hydrogen atom) or a methyl group.

The gist of the compound according to claim 4 is the compound according to claim 1, wherein R ⁵ includes —CO— and —OH.

The compound according to claim 5 is the compound according to claim 4, wherein the R ⁵ is represented by the following formula (C3).
_{-CH 2 -CH (OH) -CH 2} -OCO- (CH 2) n -C (R 7) = CH 2
... (C3)
R ⁷ is H (hydrogen atom) or a methyl group.

The compound according to claim 6 is summarized in that in the compound according to claim 1, R ⁵ is represented by the following formula (C4).
^{_{- (CH 2) n -C (}} R 8) = CH 2 ··· (C4)
R ⁸ is H (hydrogen atom) or a methyl group.

  The gist of the polymer according to claim 7 is obtained by using the compound according to any one of claims 1 to 6.

  According to the present invention, the structure of the dibenzo [g, p] chrysene skeleton can be used effectively.

式（Ｃ１）中、Ｒ^１〜Ｒ^４のうちの少なくとも１つの基が−ＯＲ^５で表され、
少なくとも１つの基のＲ^５は、末端に重合性不飽和結合を有する炭素数２〜１２の基であり、
少なくとも１つの基以外のＲ^１〜Ｒ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
即ち、本発明の化合物として後述する式（Ｃ１−１）〜式（Ｃ１−６）で表される化合物が含まれる。 [1] Compound of the present invention The compound of the present invention is a compound represented by the following formula (C1).

In formula (C1), at least one group of R ^{1 to} R ⁴ is represented by —OR ⁵ ,
At least one group R ⁵ is a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at a terminal;
R ^{1 to} R ⁴ other than at least one group are each independently H (hydrogen atom), X (halogen atom) or a monovalent group.
That is, compounds represented by formula (C1-1) to formula (C1-6) described later are included as the compounds of the present invention.

式（Ｃ１−１）中、Ｒ^５は、末端に重合性不飽和結合を有する炭素数２〜１２の基である。−ＯＲ^５で表される基は、１位、２位、３位及び４位のうちのいずれに置換されていてもよい。
また、式（Ｃ１−１）中、Ｒ^２〜Ｒ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。 In the above formula (C1), a compound in which one of R ^{1 to} R ⁴ is —OR ⁵ is represented by the following formula (C1-1).

In formula (C1-1), R ⁵ is a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at the terminal. The group represented by —OR ⁵ may be substituted at any of the 1-position, 2-position, 3-position and 4-position.
In formula (C1-1), R ^{2 to} R ⁴ each independently represent H (hydrogen atom), X (halogen atom), or a monovalent group.

式（Ｃ１−２）中、Ｒ^５１及びＲ^５２は、各々独立に、末端に重合性不飽和結合を有する炭素数２〜１２の基である。また、式（Ｃ１−２）中、Ｒ^２及びＲ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
式（Ｃ１−２）において、−ＯＲ^５１と−ＯＲ^５２との置換位置の組合せとしては、［１，９］、［１，１０］、［１，１１］、［１，１２］、［２，９］、［２，１０］、［２，１１］、［２，１２］、［３，９］、［３，１０］、［３，１１］、［３，１２］、［４，９］、［４，１０］、［４，１１］、［４，１２］が挙げられる。 A compound in which two of R ^{1 to} R ⁴ in the above formula (C1) are the above —OR ⁵ is represented by the following formula (C1-2) to formula (C1-4).

In formula (C1-2), R ⁵¹ and R ⁵² are each independently a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at the terminal. In Formula (C1-2), R ² and R ⁴ are each independently H (hydrogen atom), X (halogen atom), or a monovalent group.
In the formula (C1-2), combinations of substitution positions of -OR ⁵¹ and -OR ⁵² are [1,9], [1,10], [1,11], [1,12], [2 , 9], [2, 10], [2, 11], [2, 12], [3, 9], [3, 10], [3, 11], [3, 12], [4, 9 ], [4,10], [4,11], [4,12].

式（Ｃ１−３）中、Ｒ^５１及びＲ^５２は、各々独立に、末端に重合性不飽和結合を有する炭素数２〜１２の基である。また、式（Ｃ１−３）中、Ｒ^３及びＲ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
式（Ｃ１−３）において、−ＯＲ^５１と−ＯＲ^５２との置換位置の組合せとしては、［１，５］、［１，６］、［１，７］、［１，８］、［２，５］、［２，６］、［２，７］、［２，８］、［３，５］、［３，６］、［３，７］、［３，８］、［４，５］、［４，６］、［４，７］、［４，８］が挙げられる。

In formula (C1-3), R ⁵¹ and R ⁵² each independently represent a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at the terminal. In formula (C1-3), R ³ and R ⁴ are each independently H (hydrogen atom), X (halogen atom) or a monovalent group.
In the formula (C1-3), combinations of substitution positions of -OR ⁵¹ and -OR ⁵² are [1,5], [1,6], [1,7], [1,8], [2 , 5], [2, 6], [2, 7], [2, 8], [3, 5], [3, 6], [3, 7], [3, 8], [4, 5 ], [4,6], [4,7], [4,8].

式（Ｃ１−４）中、Ｒ^５１及びＲ^５２は、各々独立に、末端に重合性不飽和結合を有する炭素数２〜１２の基である。また、式（Ｃ１−４）中、Ｒ^２及びＲ^３は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
式（Ｃ１−４）において、−ＯＲ^５１と−ＯＲ^５２との置換位置の組合せとしては、［１，１３］、［１，１４］、［１，１５］、［１，１６］、［２，１３］、［２，１４］、［２，１５］、［２，１６］、［３，１３］、［３，１４］、［３，１５］、［３，１６］、［４，１３］、［４，１４］、［４，１５］、［４，１６］が挙げられる。

In formula (C1-4), R ⁵¹ and R ⁵² are each independently a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at the terminal. In formula (C1-4), R ² and R ³ are each independently H (hydrogen atom), X (halogen atom) or a monovalent group.
In the formula (C1-4), combinations of substitution positions of —OR ⁵¹ and —OR ⁵² are [1,13], [1,14], [1,15], [1,16], [2 , 13], [2, 14], [2, 15], [2, 16], [3, 13], [3, 14], [3, 15], [3, 16], [4, 13 ], [4,14], [4,15], [4,16].

式（Ｃ１−５）中、Ｒ^５１、Ｒ^５２及びＲ^５３は、各々独立に、末端に重合性不飽和結合を有する炭素数２〜１２の基である。また、式（Ｃ１−５）中、Ｒ^４は、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
式（Ｃ１−５）において、−ＯＲ^５１、−ＯＲ^５２及び−ＯＲ^５３の置換位置の組合せとしては、［１，５，９］、［１，５，１０］、［１，５，１１］、［１，５，１２］、［１，６，９］、［１，６，１０］、［１，６，１１］、［１，６，１２］、［１，７，９］、［１，７，１０］、［１，７，１１］、［１，７，１２］、［１，８，９］、［１，８，１０］、［１，８，１１］、［１，８，１２］、［２，５，９］、［２，５，１０］、［２，５，１１］、［２，５，１２］、［２，６，９］、［２，６，１０］、［２，６，１１］、［２，６，１２］、［２，７，９］、［２，７，１０］、［２，７，１１］、［２，７，１２］、［２，８，９］、［２，８，１０］、［２，８，１１］、［２，８，１２］、［３，５，９］、［３，５，１０］、［３，５，１１］、［３，５，１２］、［３，６，９］、［３，６，１０］、［３，６，１１］、［３，６，１２］、［３，７，９］、［３，７，１０］、［３，７，１１］、［３，７，１２］、［３，８，９］、［３，８，１０］、［３，８，１１］、［３，８，１２］、［４，５，９］、［４，５，１０］、［４，５，１１］、［４，５，１２］、［４，６，９］、［４，６，１０］、［４，６，１１］、［４，６，１２］、［４，７，９］、［４，７，１０］、［４，７，１１］、［４，７，１２］、［４，８，９］、［４，８，１０］、［４，８，１１］、［４，８，１２］が挙げられる。 In the above formula (C1), a compound in which three of R ^{1 to} R ⁴ are —OR ⁵ is represented by the following formula (C1-5).

In formula (C1-5), R ⁵¹ , R ⁵² and R ⁵³ each independently represent a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at the terminal. In Formula (C1-5), R ⁴ represents H (hydrogen atom), X (halogen atom), or a monovalent group.
In the formula (C1-5), combinations of substitution positions of —OR ⁵¹ , —OR ⁵² and —OR ⁵³ are [1, 5, 9], [1, 5, 10], [1, 5, 11]. , [1, 5, 12], [1, 6, 9], [1, 6, 10], [1, 6, 11], [1, 6, 12], [1, 7, 9], [ 1, 7, 10], [1, 7, 11], [1, 7, 12], [1, 8, 9], [1, 8, 10], [1, 8, 11], [1, 8, 12], [2, 5, 9], [2, 5, 10], [2, 5, 11], [2, 5, 12], [2, 6, 9], [2, 6, 10], [2, 6, 11], [2, 6, 12], [2, 7, 9], [2, 7, 10], [2, 7, 11], [2, 7, 12] , [2, 8, 9], [2, 8, 10], [2, 8, 11], [2, 8, 12], [3, 5, 9], [3, 5, 10], [3, 5, 11], [3, 5, 12], [3, 6, 9], [3, 6, 10], [3, 6, 11], [3 , 6, 12], [3, 7, 9], [3, 7, 10], [3, 7, 11], [3, 7, 12], [3, 8, 9], [3, 8 , 10], [3, 8, 11], [3, 8, 12], [4, 5, 9], [4, 5, 10], [4, 5, 11], [4, 5, 12 ], [4, 6, 9], [4, 6, 10], [4, 6, 11], [4, 6, 12], [4, 7, 9], [4, 7, 10], [4, 7, 11], [4, 7, 12], [4, 8, 9], [4, 8, 10], [4, 8, 11], [4, 8, 12]. .

式（Ｃ１−６）中、Ｒ^５１、Ｒ^５２、Ｒ^５３及びＲ^５４は、各々独立に、末端に重合性不飽和結合を有する炭素数２〜１２の基である。
式（Ｃ１−６）において、−ＯＲ^５１、−ＯＲ^５２、−ＯＲ^５３及び−ＯＲ^５４の置換位置の組合せとしては、［３，６，１１，１４］、［３，６，１１，１５］、［３，６，１０，１５］、［２，７，１０，１４］、［２，７，１０，１５］、［３，７，１０，１４］、［３，７，１１，１５］、［３，６，１０，１４］、［３，７，１０，１５］、［３，７，１１，１４］、［２，７，１１，１４］、［２，７，１１，１５］、［２，６，１０，１４］、［２，６，１０，１５］、［２，６，１１，１４］、［２，６，１１，１５］、等が挙げられる。 The compound in which all ^four of R ^{1 to} R ⁴ in the formula (C1) are —OR ⁵ is represented by the following formula (C1-6).

In formula (C1-6), R ⁵¹ , R ⁵² , R ⁵³ and R ⁵⁴ each independently represent a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at the terminal.
In the formula (C1-6), combinations of substitution positions of —OR ⁵¹ , —OR ⁵² , —OR ⁵³ and —OR ⁵⁴ are [3, 6, 11, 14], [3, 6, 11, 15]. [3, 6, 10, 15], [2, 7, 10, 14], [2, 7, 10, 15], [3, 7, 10, 14], [3, 7, 11, 15] [3, 6, 10, 14], [3, 7, 10, 15], [3, 7, 11, 14], [2, 7, 11, 14], [2, 7, 11, 15] , [2, 6, 10, 14], [2, 6, 10, 15], [2, 6, 11, 14], [2, 6, 11, 15], and the like.

The compounds represented by these formulas (C1-1) to (C1-6) may be synthesized in any way. Usually, a dibenzochrysene derivative having a group containing —O— directly bonded to a dibenzochrysene skeleton is used, and an atomic group having a polymerizable unsaturated bond terminal is bonded to this group. Such dibenzochrysene skeleton group comprising -O- is bonded directly to a hydroxyl (-OH), an glycidyl ether group _{(-O-CH 2 -C 2 H} 3 O), - O-C n H groups represented by _2n -OH (where n = 2 to 12, _{specifically, -O-C 2 H 4 -OH} , -O-C 3 H 6 -OH, -O-C 4 H 8 -OH Etc.}, a group represented by —O— (C _n H _2n —O) _m —H (where n = 2 to 12, m = 2 to 6, specifically —O— (C ₂ H ₄ — _{O-) m -H, -O- (C} 3 H 6 -O-) m -H, -O- (C 4 H 8 -O-) m -H , etc.} and the like. these groups, Only 1 type may be contained in the dibenzochrysene derivative and 2 or more types may be contained.

Examples of the dibenzochrysene derivative having such a group include, for example, hydroxydibenzochrysene {see the following formula (A1)}, dibenzochrysene glycidyl ether {see the following formula (A2)}, polyglycol comprising an ethylene oxide adduct of hydroxydibenzochrysene Examples include ethers {refer to the following formula (A3), usually n = 1 to 4}, polyglycol ethers composed of propylene oxide adducts of hydroxydibenzochrysene {refer to the following formula (A3), usually n = 1 to 3}, and the like. The following formulas (A1) to (A4) exemplify monofunctional derivatives of dibenzochrysene, but naturally, bifunctional, trifunctional, and tetrafunctional derivatives are also included.

Among the above-mentioned various dibenzochrysene derivatives, when using a hydroxydibenzochrysene derivative having a hydroxyl group at the end of the group as in formula (A1), formula (A3), and formula (A4), the terminal hydroxyl group (- OH) can be obtained by adding a polymerizable unsaturated bond terminal.
When dibenzochrysene glycidyl ether {the above formula (A2) and similar polyfunctional derivatives} is used, an epoxy ring (—C ₂ ) of the glycidyl ether group (—O—CH ₂ —C ₂ H ₃ O) is used. It can be obtained by opening a ring of H ₃ O) and then adding a polymerizable unsaturated bond end.

[2] Group represented by —OR ⁵ R ⁵ in Formula (C1) is a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at the terminal. That is, in formulas (C1-2) to (C1-6), R ⁵¹ , R ⁵² , R ⁵³ and R ⁵⁴ are each independently a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at the terminal. is there. R ⁵ in the following description is common to the aforementioned R ⁵¹ , R ⁵² , R ⁵³ and R ⁵⁴ .

R ⁵ can be a group having 2 to 12 carbon atoms and having a polymerizable unsaturated bond at the terminal and including —CO—. Specifically, R ⁵ can be a group represented by the following formula (C2).
^{_{-CO- (CH 2) n -C (}} R 6) = CH 2 ··· (C2)
R ^{6 in the} formula (C2) is H (hydrogen atom) or a methyl group. When R ⁶ is H (hydrogen atom), n is n = 0-9. When R ⁶ is a methyl group, n is n = 0-8.

In the above formula (2), when n = 0 and R ⁶ is H (hydrogen atom), R ⁵ is represented by the following formula (C21).
_{-CO-CH = CH 2 ··· (} C21)
In the above formula (2), when n = 0 and R ⁶ is a methyl group, R ⁵ is represented by the following formula (C22).
_{-CO-C (CH 3) =} CH 2 ··· (C22)

式（Ｃ１−７）〜式（Ｃ１−１２）中のＲ^２〜Ｒ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
尚、式（Ｃ１−７）〜式（Ｃ１−１２）における下記式（Ｃ２１−１）で表される基の置換位置の組合せは、各々前述の式（Ｃ１−１）〜式（Ｃ１−６）における−ＯＲ^５と同様である。
−Ｏ−ＣＯ−ＣＨ＝ＣＨ_２ ・・・（Ｃ２１−１） Examples of the case where R ⁵ is a group represented by the above formula (C21) include the following formulas (C1-7) to (C1-12).

R ^{2 to} R ^{4 in} Formula (C1-7) to Formula (C1-12) are each independently H (hydrogen atom), X (halogen atom), or a monovalent group.
The combinations of the substitution positions of the groups represented by the following formula (C21-1) in the formulas (C1-7) to (C1-12) are the same as those in the above formulas (C1-1) to (C1-6), respectively. The same as -OR ^{5 in} ).
—O—CO—CH═CH ₂ (C21-1)

上記アクリロイルハライドとしては、アクリロイルクロライド及びアクリロイルブロマイドが挙げられる。これらは１種のみを用いてもよく２種以上を併用してもよい。 The compound {formula (C1-7) to formula (C1-12)} in which R ⁵ is a group represented by formula (C21) is obtained, for example, by reacting acryloyl halide with hydroxydibenzochrysene. An acryloyl halide is a compound represented by X—CO—CH═CH ₂ (where X is a halogen atom) and can react with a hydroxyl group of hydroxydibenzochrysene to give an acryloyl group (the following scheme). S1).

Examples of the acryloyl halide include acryloyl chloride and acryloyl bromide. These may use only 1 type and may use 2 or more types together.

式（Ｃ１−１３）〜式（Ｃ１−１８）中のＲ^２〜Ｒ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
尚、式（Ｃ１−１３）〜式（Ｃ１−１８）における下記式（Ｃ２２−１）で表される基の置換位置の組合せは、各々前述の式（Ｃ１−１）〜式（Ｃ１−６）における−ＯＲ^５と同様である。
−Ｏ−ＣＯ−Ｃ（ＣＨ_３）＝ＣＨ_２ ・・・（Ｃ２２−１） Examples of the case where R ⁵ is a group represented by the above formula (C22) include the following formulas (C1-13) to (C1-18).

R ^{2 to} R ^{4 in} formula (C1-13) to formula (C1-18) each independently represent H (hydrogen atom), X (halogen atom) or a monovalent group.
The combinations of the substitution positions of the groups represented by the following formula (C22-1) in the formulas (C1-13) to (C1-18) are the same as those in the above formulas (C1-1) to (C1-6), respectively. The same as -OR ^{5 in} ).
_{-O-CO-C (CH 3} ) = CH 2 ··· (C22-1)

The compound {formula (C1-13) to formula (C1-18)} in which R ⁵ is a group represented by formula (C22) can be obtained, for example, by reacting hydroxydibenzochrysene with methacryloyl halide. A methacryloyl halide is a compound represented by X—CO—C (CH ₃ ) ═CH ₂ (where X is a halogen atom) and can react with a hydroxyl group of hydroxydibenzochrysene to give a methacryloyl group. Yes (see Scheme S2 below).

On the other hand, when n ≧ 1 in formula (C2) and R ⁶ is H (hydrogen atom), R ⁵ is represented by formula (C23). However, n = 1-9.
_{-CO- (CH 2) n -CH =} CH 2 ··· (C23)
In the formula (C2), when n ≧ 1, and R ⁶ is a methyl group, the above R ⁵ is represented by the formula (C24). However, n = 1-8.
_{-CO- (CH 2) n -C (} CH 3) = CH 2 ··· (C24)

In addition to the formula (C21), the formula (C22), the formula (C23) and the formula (C24), the R ⁵ has a polymerizable unsaturated bond at the terminal, contains —CO—, and has 2 carbon atoms. Examples of the group of ˜12 include groups represented by the following formula (C5).
^{_{- (CH 2) n -OCO-}} C (R 9) = CH 2 ··· (C5)
R ^{9 in} formula (C5) is H (hydrogen atom) or a methyl group, n = 1 to 9 when R ⁹ is H (hydrogen atom), and n = when R ⁹ is a methyl group. 1-8.

In addition, examples of the case where R ⁵ has a polymerizable unsaturated bond at the terminal and includes —CO— and is a group having 2 to 12 carbon atoms include a group represented by the following formula (C6). .
—R ¹⁰ —CH ₂ —OCO—C (R ¹¹ ) ═CH ₂ ... (C6)
However, R ¹⁰ in the formula (C6) is represented by the following formula (C61) or the following formula (C62).
_{- (C 2 H 4 -O-)} n - ··· (C61)
_{- (C 3 H 6 -O-)} l - ··· (C62)
R ^{11 in the} formula (C6) is H (hydrogen atom) or a methyl group. When R ¹¹ is H (hydrogen atom), n = 1 to 4, and l = 1 to 2. When R ¹¹ is a methyl group, n = 1 to 3, and l = 1 to 2.

That is, when R ¹⁰ in Formula (C6) is represented by Formula (C61) and R ¹¹ in Formula (C6) is H (hydrogen atom), R ⁵ is represented by Formula (C61-1). The However, n = 1 to 4.
_{- (C 2 H 4 -O-)} n -CH 2 -OCO-CH = CH 2 ··· (C61-1)
When R ¹⁰ in the formula (C6) is represented by the formula (C61) and R ¹¹ in the formula (C6) is a methyl group, the R ⁵ is represented by the formula (C61-2). However, n = 1 to 3.
_{- (C 2 H 4 -O-)} n -CH 2 -OCO-C (CH 3) = CH 2
... (C61-2)

In addition, when R ¹⁰ in the formula (C6) is represented by the formula (C62) and R ¹¹ in the formula (C6) is H (hydrogen atom), the R ⁵ is represented by the formula (C62-1). The However, l = 1-2.
_{- (C 3 H 6 -O-)} l -CH 2 -OCO-CH = CH 2 ··· (C62-1)
When R ¹⁰ in the formula (C6) is represented by the formula (C62) and R ¹¹ in the formula (C6) is a methyl group, the R ⁵ is represented by the formula (C62-2). However, l = 1-2.
_{- (C 3 H 6 -O-)} l -CH 2 -OCO-C (CH 3) = CH 2
... (C62-2)

R ⁵ may have a polymerizable unsaturated bond at the terminal and may be a group having 2 to 12 carbon atoms including —CO— and —OH. Specifically, R ⁵ can be a group represented by the following formula (C3).
_{-CH 2 -CH (OH) -CH 2} -OCO- (CH 2) n -C (R 7) = CH 2
... (C3)
R ^{7 in} formula (C3) is H (hydrogen atom) or a methyl group. When R ⁷ is H (hydrogen atom), n is n = 0-6. Further, n in the case ^{R 7} is a methyl group is n = 0 to 5.

In the above formula (C3), when n = 0 and R ⁷ is H (hydrogen atom), R ⁵ is represented by the following formula (C31).
_{-CH 2 -CH (OH) -CH 2} -OCO-CH = CH 2 ··· (C31)
Further, when n = 0 in the above formula (C3) and R ⁷ is a methyl group, R ⁵ is represented by the following formula (C32).
—CH ₂ —CH (OH) —CH ₂ —OCO—C (CH ₃ ) ═CH ₂ ... (C32)

式（Ｃ１−１９）〜式（Ｃ１−２４）中のＲ^２〜Ｒ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
尚、式（Ｃ１−１９）〜式（Ｃ１−２４）における−ＯＲ^５、即ち、下記式（Ｃ３１−１）で表される基の置換位置の組合せは、各々前述の式（Ｃ１−１）〜式（Ｃ１−６）における場合と同様である。
−Ｏ−ＣＨ_２−ＣＨ（ＯＨ）−ＣＨ_２−ＯＣＯ−ＣＨ＝ＣＨ_２ ・・（Ｃ３１−１） Examples of the case where R ⁵ is a group represented by the above formula (C31) include the following formulas (C1-19) to (C1-24).

R ^{2 to} R ^{4 in} Formula (C1-19) to Formula (C1-24) are each independently H (hydrogen atom), X (halogen atom), or a monovalent group.
In addition, in the formula (C1-19) to the formula (C1-24), —OR ⁵ , that is, the combination of the substitution positions of the groups represented by the following formula (C31-1), is the formula (C1-1) described above. ~ Same as in formula (C1-6).
—O—CH ₂ —CH (OH) —CH ₂ —OCO—CH═CH ₂ ... (C31-1)

The compound {formula (C1-19) to formula (C1-24)} in which R ⁵ is a group represented by the formula (C31) is, for example, dibenzochrysene glycidyl ether and acrylic acid (CH ₂ ═CH—COOH). ) Is reacted. Acrylic acid can give an acryloyloxy group (—OCO—CH═CH ₂ ) after opening the epoxy ring of the glycidyl ether group (see Scheme S3 below).

In addition, the compound {formula (C1-19) to formula (C1-24)} in which R ⁵ is a group represented by formula (C31) includes, for example, hydroxydibenzochrysene and glycidyl acrylate (CH ₂ ═CH— _{CO-O-CH 2} and -C _{2 H} 3 O) is obtained by reacting. Glycidyl acrylate can react with the hydroxyl group of hydroxydibenzochrysene to give an acryloyl group (see Scheme S3 ′ below).

式（Ｃ１−２５）〜式（Ｃ１−３０）中のＲ^２〜Ｒ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
尚、式（Ｃ１−２５）〜式（Ｃ１−３０）における下記式（Ｃ３２−１）で表される基の置換位置の組合せは、各々前述の式（Ｃ１−１）〜式（Ｃ１−６）における−ＯＲ^５と同様である。
−Ｏ−ＣＨ_２−ＣＨ（ＯＨ）−ＣＨ_２−ＯＣＯ−Ｃ（ＣＨ_３）＝ＣＨ_２
・・・（Ｃ３２−１） Examples of the case where R ⁵ is a group represented by the above formula (C32) include the following formulas (C1-25) to (C1-30).

R ^{2 to} R ^{4 in} Formula (C1-25) to Formula (C1-30) are each independently H (hydrogen atom), X (halogen atom), or a monovalent group.
In addition, the combination of the substitution position of the group represented by the following formula (C32-1) in the formula (C1-25) to the formula (C1-30) is respectively the above formula (C1-1) to the formula (C1-6). The same as -OR ^{5 in} ).
_{-O-CH 2 -CH (OH)} -CH 2 -OCO-C (CH 3) = CH 2
... (C32-1)

The compound {formula (C1-25) to formula (C1-30)} in which R ⁵ is a group represented by the formula (C32) is obtained by, for example, dibenzochrysene glycidyl ether with methacrylic acid {CH ₂ ═C (CH ₃ ) obtained by reacting —COOH}. Methacrylic acid can give a methacryloyloxy group {—OCO—C (CH ₃ ) ═CH ₂ } after opening the epoxy ring of the glycidyl ether group (see Scheme S4 below).

In addition, the compound {formula (C1-25) to formula (C1-30)} in which R ⁵ is a group represented by formula (C32) is prepared by, for example, adding glycidyl methacrylate {CH ₂ = C ( obtained by reacting _{CH 3) -CO-O-CH} 2 -C 2 H 3 O}. Glycidyl methacrylate can react with the hydroxyl group of hydroxydibenzochrysene to give a methacryloyl group (see Scheme S4 ′ below).

On the other hand, when n ≧ 1 in formula (C3) and R ⁷ is H (hydrogen atom), R ⁵ is represented by formula (C33). However, n = 1-6.
_{-CH 2 -CH (OH) -CH 2} -OCO- (CH 2) n -CH = CH 2
... (C33)
In the formula (C3), when n ≧ 1, and R ⁷ is a methyl group, R ⁵ is represented by the formula (C34). However, n = 1-5.
_{-CH 2 -CH (OH) -CH 2} -OCO- (CH 2) n -C (CH 3) = CH 2
... (C34)

In addition to the formula (C31), the formula (C32), the formula (C33) and the formula (C34), the R ⁵ has a polymerizable unsaturated bond at the terminal, contains -CO- and -OH, and contains carbon atoms. Examples of the group having 2 to 12 include groups represented by the following formula (C7).
_{- (CH 2) n -CH (} OH) -CH 2 -OCO-C (R 12) = CH 2 ·· (C7)
R ^{12 in} formula (C7) is H (hydrogen atom) or a methyl group. When R ¹² is H (hydrogen atom), n = 1 to 7, and when R ¹² is a methyl group, n = 1 to 6.

In addition, when R ⁵ has a polymerizable unsaturated bond at the terminal, includes —CO— and —OH, and is a group having 2 to 12 carbon atoms, the group represented by the following formula (C8) Is mentioned.
—R ¹³ —CH ₂ —CH (OH) —CH ₂ —OCO—C (R ¹⁴ ) ═CH ₂ ... (C8)
However, R ¹³ in the formula (C8) is represented by the following formula (C81) or the following formula (C82).
_{- (C 2 H 4 -O-)} n - ··· (C81)
_{- (C 3 H 6 -O-)} l - ··· (C82)
R ^{14 in} formula (C8) is H (hydrogen atom) or a methyl group. When R ¹⁴ is H (hydrogen atom), n = 1 to 3, and l = 1 to 2. In addition, when R ¹⁴ is a methyl group, n = 1 to 2 and 1 = 1.

That is, when R ¹³ in the formula (C8) is represented by the formula (C81) and R ¹⁴ in the formula (C8) is H (hydrogen atom), the R ⁵ is represented by the formula (C81-1). The However, n = 1 to 3.
_{- (C 2 H 4 -O-)} n -CH 2 -CH (OH) -CH 2 -OCO-CH = CH 2
... (C81-1)
When R ¹³ in formula (C8) is represented by formula (C81) and R ¹⁴ in formula (C8) is a methyl group, R ⁵ is represented by formula (C81-2). However, n = 1-2.
_{- (C 2 H 4 -O-)} n -CH 2 -CH (OH) -CH 2 -OCO-C (CH 3) = CH 2
... (C81-2)

When R ¹³ in formula (C8) is represented by formula (C82) and R ¹⁴ in formula (C8) is H (hydrogen atom), R ⁵ is represented by formula (C82-1). The However, l = 1-2.
_{- (C 3 H 6 -O-)} l -CH 2 -CH (OH) -CH 2 -OCO-CH = CH 2
... (C82-1)

When R ¹³ in Formula (C8) is represented by Formula (C82) and R ¹⁴ in Formula (C8) is a methyl group, R ⁵ is represented by Formula (C82-2).
_{-C 3 H 6 -O - CH 2} -CH (OH) -CH 2 -OCO-C (CH 3) = CH 2
... (C82-2)

In addition, as illustrated as the above-mentioned scheme S3 ′ and the above-mentioned scheme S4 ′, by using a glycidyl (meth) acrylate compound (a compound having a glycidyl ether group and an acryloyl group), various kinds of compounds according to these compounds are used. A dibenzochrysene derivative is obtained. For example, if a glycidyl (meth) acrylate compound in which an alkylene chain is interposed between a glycidyl ether group and an acryloyl group is used, a desired alkylene chain can be introduced into R ⁵ . If a glycidyl (meth) acrylate compound in which a polyoxyalkylene chain is interposed between a glycidyl ether group and an acryloyl group is used, a desired polyoxyalkylene chain can be introduced into R ⁵ .

In addition, examples of R ⁵ include a group represented by the following formula (C4).
^{_{- (CH 2) n -C (}} R 8) = CH 2 ··· (C4)
R ^{8 in} formula (C4) is H (hydrogen atom) or a methyl group. When this R ⁸ is H (hydrogen atom), n is n = 0 to 10. When R ⁸ is a methyl group, n is n = 0-9.

In the above formula (C4), when n = 0 and R ⁸ is H (hydrogen atom), R ⁵ is represented by the following formula (C41).
_{-CH 2 -CH = CH 2 ··· (} C41)
Further, when n = 0 in the above formula (C4) and R ⁸ is a methyl group, R ⁵ is represented by the following formula (C42).
_{-CH 2 -C (CH 3) =} CH 2 ··· (C42)

式（Ｃ１−３１）〜式（Ｃ１−３６）中のＲ^２〜Ｒ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
尚、式（Ｃ１−３１）〜式（Ｃ１−３６）における下記式（Ｃ４１−１）で表される基の置換位置の組合せは、各々前述の式（Ｃ１−１）〜式（Ｃ１−６）における−ＯＲ^５と同様である。
−Ｏ−ＣＨ_２−ＣＨ＝ＣＨ_２ ・・・（Ｃ４１−１） Examples of the case where R ⁵ is a group represented by the above formula (C41) include the following formulas (C1-31) to (C1-36).

R ^{2 to} R ^{4 in} Formula (C1-31) to Formula (C1-36) each independently represent H (hydrogen atom), X (halogen atom), or a monovalent group.
The combinations of the substitution positions of the groups represented by the following formula (C41-1) in the formulas (C1-31) to (C1-36) are the same as those in the above formulas (C1-1) to (C1-6), respectively. The same as -OR ^{5 in} ).
_{-O-CH 2 -CH = CH 2} ··· (C41-1)

The compound {Formula (C1-31) to Formula (C1-36)} in which R ⁵ is a group represented by the formula (C41) is, for example, hydroxydibenzochrysene and halogenated propene (3-chloro-1- And propene, 3-bromo-1-propene, etc.). The halogenated propene is a compound represented by X—CH ₂ —CH═CH ₂ (where X is a halogen atom), and is a 2-propenyl group (—CH ₂ —CH with respect to the hydroxyl group of hydroxydibenzochrysene. ═CH ₂ ) (see Scheme S5 below).

In addition, the compound in which R ⁵ is a group represented by the formula (C42) includes, for example, hydroxydibenzochrysene and halogenated methylpropene (3-chloro-2-methyl-1-propene, 3-bromo-2- Methyl-1-propene and the like). The halogenated methylpropene is a compound represented by X—CH ₂ —C (CH ₃ ) ═CH ₂ (where X is a halogen atom), and is 2-methyl-2 with respect to the hydroxyl group of hydroxydibenzochrysene. - it is possible to impart propenyl group _{{-CH 2 -C (CH 3)} = CH 2} ( see below scheme S6).

On the other hand, when n ≧ 1 in formula (C4) and R ⁸ is H (hydrogen atom), R ⁵ is represented by formula (C43). However, n = 1-10.
_{- (CH 2) n -CH =} CH 2 ··· (C43)
In the formula (C4), when n ≧ 1, and R ⁸ is a methyl group, R ⁵ is represented by the formula (C44). However, n = 1-9.
_{- (CH 2) n -C (} CH 3) = CH 2 ··· (C44)

In addition to the above formula (C41), formula (C42), formula (C43) and formula (C44), examples of R ⁵ include a group represented by the following formula (C9).
_{^{-R 15 -CH 2 -C (R 16}} ) = CH 2 ··· (C9)
However, ^{R 15} in the formula (C9) is represented by the following formula (C91) or the following formula (C92).
_{- (C 2 H 4 -O-)} n - ··· (C91)
_{- (C 3 H 6 -O-)} l - ··· (C92)
R ^{16 in the} formula (C9) is H (hydrogen atom) or a methyl group. When R ¹⁶ is H (hydrogen atom), n = 1 to 4 and l = 1 to 3. When R ¹⁶ is a methyl group, n = 1 to 4, and l = 1 to 2.

That is, when R ¹⁵ in the formula (C9) is represented by the formula (C91) and R ¹⁶ in the formula (C9) is H (hydrogen atom), the R ⁵ is represented by the formula (C91-1). The However, n = 1 to 4.
_{- (C 2 H 4 -O-)} n -CH 2 -CH = CH 2 ··· (C91-1)
When R ¹⁵ in Formula (C9) is represented by Formula (C91) and R ¹⁶ in Formula (C9) is a methyl group, R ⁵ is represented by Formula (C91-2). However, n = 1 to 4.
_{- (C 2 H 4 -O-)} n -CH 2 -C (CH 3) = CH 2 ·· (C91-2)

When R ¹⁵ in the formula (C9) is represented by the formula (C92) and R ¹⁶ in the formula (C9) is H (hydrogen atom), the R ⁵ is represented by the formula (C92-1). The However, l = 1 to 3.
_{- (C 3 H 6 -O-)} l -CH 2 -CH = CH 2 ··· (C92-1)
When R ¹⁵ in Formula (C9) is represented by Formula (C92) and R ¹⁶ in Formula (C9) is a methyl group, R ⁵ is represented by Formula (C92-2). However, l = 1-2.
_{- (C 3 H 6 -O-)} l -CH 2 -C (CH 3) = CH 2 ·· (C92-2)

[3] Groups Other than —OR ^{5 In} the compound of the present invention, in the formula (C1), groups other than —OR ⁵ among R ^{1 to} R ⁴ are each independently H (hydrogen atom), X (halogen atom). ) Or a monovalent group.
Examples of the monovalent group include monovalent groups containing O (oxygen atom) directly bonded to the dibenzochrysene skeleton. Specifically, a group represented by a hydroxyl group (—OH), a glycidyl ether group (—O—CH ₂ —C ₂ H ₃ O), —O—C _n H _2n —OH (where n = 2 to 12). , Specifically, —O—C ₂ H ₄ —OH, —O—C ₃ H ₆ —OH, —O—C ₄ H ₈ —OH, etc.}, —O— (C _n H _2n —O) _m Groups represented by —H (where n = 2 to 12, m = 2 to 6, specifically —O— (C ₂ H ₄ —O—) _m —H, —O— (C ₃ H _{6 -O-) m -H, -O- (C} 4 H 8 -O-) m -H , etc.} and the like.

Furthermore, examples of the monovalent group include a monovalent group containing C (carbon atom) directly bonded to the dibenzochrysene skeleton, that is, a monovalent organic group. Specific examples include an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkenyl group, and halogen substituents thereof. Usually, these monovalent organic groups have 1 to 12 carbon atoms.
Examples of the monovalent group include monovalent groups containing N (nitrogen atom) directly bonded to the dibenzochrysene skeleton. Specific examples include a nitro group (—NO ₂ ) and an amino group (—NH ₂ ).

The size of the monovalent group is not particularly limited, but usually has a molecular weight smaller than —OR ⁵ . Such monovalent groups include, for example, dibenzochrysene derivatives, which are starting materials when introducing —OR ⁵ , and groups originally possessed by dibenzochrysene derivatives, which are intermediate compounds, and other than —OR ^5. Is a group subsequently introduced into the dibenzochrysene derivative as

[4] Use of Compound Each compound having a dibenzo [g, p] chrysene skeleton of the present invention represented by the above formula (C1) is useful as a monomer, a curing agent, a crosslinking agent, and the like.
In particular, the monomer can be used as a monomer for supplying a polymerizable terminal, an oligomer for supplying a polymerizable terminal, or the like for obtaining a polymer. Each compound of the present invention may be used alone as a monomer or oligomer, or may be used in combination with another monomer or oligomer having a polymerizable unsaturated bond.

  When the compound of the present invention is used as a monomer, a conjugated condensed polycyclic structure (dibenzo [g, p] chrysene skeleton) can be introduced into the main chain of the polymer. For this reason, compared with the case where the conventional general purpose monomer is utilized, a glass transition point is high and high heat resistance can be obtained. Further, the thermal conductivity can be improved by stacking the dibenzo [g, p] chrysene skeletons. Furthermore, the dibenzo [g, p] chrysene skeleton having a large conjugated structure is a rigid molecule and has high heat resistance. Nevertheless, it exhibits a twisted structure and has a relatively high solubility in solvents and the like. For this reason, blending with other monomers is easy, and it is easy to control the properties of the resulting polymer. The dibenzo [g, p] chrysene skeleton has a twisted structure in which the carbon atoms at the 3-position, 6-position, 11-position and 14-position constituting this skeleton are not arranged in the same plane, and various optical isomers can be obtained. Have. For this reason, the toughness of the polymer obtained can be improved by using together the compound which has different optical activity from the said dibenzo [g, p] chrysene compound.

  Moreover, the compound of this invention can be made into the compound which coexisted in the molecule | numerator the group which exhibits a hydroxyl terminal, a glycidyl terminal, a vinyl ether terminal, a (meth) acryloyl terminal, and these different polymerization characteristics. For this reason, when such a dibenzochrysene derivative is used, it can superpose | polymerize combining different polymerization forms, such as photopolymerization, thermal polymerization, cationic polymerization, and radical polymerization. That is, it can be used as a different polymerizable monomer. For example, among the compounds included in formula (C1-19) to formula (C1-23) and formula (C1-25) to formula (C1-29), a compound having both a glycidyl terminal and a (meth) acryloyl terminal Specifically, the following formula (C1-19a), formula (C1-21a), formula (C1-23a), formula (C1-25a), formula (C1-27a), formula (C1-29a), and the like This compound can be cured using a (meth) acryloyl end and further cured using a glycidyl end. Thereby, it is possible to obtain a very dense cured body (polymer). In such a polymer, the significance of having the above-described dibenzochrysene skeleton can be more effectively exhibited.

[5] Polymer of the present invention The polymer of the present invention is obtained by using the compound of the present invention. That is, the compound of the present invention may be used in any manner during the polymerization, but for example, as described above, it can be used as a monomer, a curing agent, a crosslinking agent, and the like.

When the compound having a dibenzo [g, p] chrysene skeleton of the present invention is used as a monomer, a conjugated condensed polycyclic structure (dibenzo [g, p] chrysene skeleton) is introduced into the main chain of the resulting polymer. it can. A polymer in which a dibenzo [g, p] chrysene skeleton is introduced can obtain a higher glass transition temperature than a polymer obtained using only conventional general-purpose monomers. That is, a polymer having high heat resistance can be obtained.
Moreover, since the polymer obtained has a stacking structure of dibenzo [g, p] chrysene skeletons, a polymer having excellent thermal conductivity can be obtained.
Furthermore, the polymer having a dibenzo [g, p] chrysene skeleton exhibits a twisted structure in which the carbon atoms at the 3-position, 6-position, 11-position and 14-position constituting the skeleton are not arranged in the same plane. Has optical isomers. For this reason, a polymer having high toughness can be obtained by using a compound having different optical activity from the compounds of the present invention having a dibenzo [g, p] chrysene skeleton.

Examples of the polymer of the present invention include copolymers of the above-described various compounds (1) of the present invention and other compounds (2) copolymerizable with the compounds of the present invention.
Examples of the compound other than that (the compound of the present invention) copolymerizable with the compound of the present invention include, for example, an aliphatic vinyl compound, an aromatic vinyl compound, an unsaturated nitrile compound, an unsaturated organic acid, and an unsaturated organic acid ester. Compounds, halogenated vinyl compounds and the like.

  That is, examples of the aliphatic vinyl compound include linear α-olefins such as ethylene, 1-butene, 1-pentene, 1-hexene, 1-heptene and 1-octene, 2-methyl-1-propene, and 3-methyl. Branched α-olefins such as -1-pentene, 4-methyl-1-pentene, 5-methyl-1-hexene, 4-methyl-1-hexene, 4,4-dimethyl-1-pentene, butadiene, isoprene, etc. Conjugated dienes and the like.

  Examples of aromatic vinyl compounds include styrene, methylstyrene, dimethylstyrene, diisopropylstyrene, butylstyrene, divinylbenzene, N, N-dimethyl-p-aminoethylstyrene, 2,4-dimethylstyrene, N, N-diethyl-p. -Aminoethylstyrene, 2,4-dimethylstyrene, vinylbenzyldimethylamine, vinylbenzyldimethylaminoethanolamine, 4-tert-butoxystyrene, vinylpyridine, vinylnaphthalene, vinylanthracene and the like.

Examples of the unsaturated nitrile compound include acrylonitrile and methacrylonitrile.
Examples of the unsaturated organic acid include acrylic acid, methacrylic acid, crotonic acid, maleic acid, fumaric acid and itaconic acid.
Examples of the unsaturated organic acid ester compound include alkyl esters, alkoxy esters, hydroxyl group-containing esters, amino group-containing esters, and amide group-containing esters of the above unsaturated organic acids.

  Hereinafter, the embodiment of the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples. In the following, dibenzo [g. p] Chrysene is simply referred to as “dibenzochrysene” or “DBC”.

  In the following LC / MS analysis, a liquid chromatograph mass spectrometer (manufactured by Agilent Technologies, model “6220 Accurate-Mass TOF LC / MS”) was used. As LC conditions, Agilent Extended C-18 (50 mm × 4.6 mm, 1.8 μm) was used for the column. Mobile phase (A) methanol and (B) 5 mM ammonium formate were used. Gradient up to 5 minutes A: B = 6: 4, 5 to 10 minutes A: B = 10: 0, further 10 to 15 minutes A: B = 10: 0, then A: B = 6: 4 Retained. As MS conditions, positive APPI was used for the ionization mode, Vcap = 3500V, and fragmentor 150V.

<Synthesis Example 1> Production of hydroxydibenzochrysene Using dibenzochrysene, dibenzochrysenesulfonic acid calcium salt was obtained by synthesis shown in the following scheme (S11). Furthermore, hydroxy dibenzochrysene was obtained using the obtained calcium dibenzochrysene sulfonate (details are described in Japanese Patent Application No. 2012-77951).

  (1-1): Purity 99.8% dibenzochrysene (manufactured by Tokyo Chemical Industry Co., Ltd .; molecular weight 328.41) 20 g (0.06 mol) and 95% sulfuric acid 200 g (1.94 mol) were reacted at 80 ° C. I let you. 400 g of distilled water was added to the contents obtained while maintaining the temperature at 40 ° C. or lower, and then 154.4 g (2.08 mol) of calcium hydroxide was added while maintaining the temperature at 45 ° C. or lower to obtain a slurry. From the resulting slurry, the filtrate (light yellow liquid) was collected and concentrated under reduced pressure to obtain 36.5 g of dibenzochrysene sulfonic acid calcium salt as a light yellow powdery solid (yield 82.7%).

  (1-2); 14.0 g (0.212 mol) of 85% potassium hydroxide particles were melted by heat. Subsequently, 4.0 g (0.0055 mol) of the dibenzochrysene sulfonic acid calcium salt obtained in (1-1) above was added to obtain a reddish brown viscous liquid. After cooling and solidifying the obtained liquid, 35% hydrochloric acid was added to the water-soluble liquid until the pH value became 3 (pH = 3) to obtain a content containing a brown solid.

  (1-3): The contents obtained up to (1-2) above were dissolved in 30 g of ethyl acetate, allowed to stand to separate into an organic phase and an aqueous phase, and then the organic phase was separated. did. Insoluble matter was removed from the collected organic phase, and the filtrate was concentrated under reduced pressure to obtain 1.6 g of hydroxydibenzochrysene as a brown powdery solid (yield 73.9%). As a result of subjecting the obtained hydroxydibenzochrysene to LC / MS analysis, it was confirmed that 98% of 4-substituted hydroxydibenzochrysene and the remaining 3-substituted hydroxydibenzochrysene were contained.

(1-4): Using a Fourier transform nuclear magnetic resonance apparatus (FT-NMR apparatus: manufactured by Bruker Biospin, model “AVANCE III-600 with Cryo Probe”), ¹ H-NMR and ¹³ C-NMR are measured. In addition, structural analysis was performed. As a result, in the 4-substituted hydroxydibenzochrysene obtained up to (1-3) above, the position of the hydroxyl group is [3, 6, 11, 14], [3, 6, 11, 15], [3, 6, 10, 15], [2, 7, 10, 14], [2, 7, 10, 15], [3, 7, 10, 14], [3, 7, 11, 15] Was found.
In addition, the measurement conditions in FT-NMR measurement are as follows.
Observation frequency: ¹ H-NMR is 600 MHz, ¹³ C-NMR is 150 MHz
Measurement solvent: DMSO-d ₆
Measurement temperature: 300K
Chemical shift criteria: ¹ H; 2.50 ppm, ¹³ C; 39.50 ppm

<Synthesis Example 2> Production of dibenzochrysene glycidyl ether Dibenzochrysene glycidyl ether was obtained by the synthesis shown in the following scheme (S12) using hydroxydibenzochrysene obtained in Synthesis Example 1 (for details, see Japanese Patent Application No. 2012-77951). Description).

  (2-1); 1.0 g (approximately 0.0255 mol) of hydroxydibenzochrysene, 10 g of ethanol, and 30 g (0.324 mol) of epichlorohydrin (manufactured by Kanto Chemical Co., Inc.) were stirred at 40 ° C.・ Mixed. While maintaining the internal temperature of 40 ° C., 0.43 g (containing 0.011 mol) of sodium hydroxide powder was added to the previous contents to obtain a solution. Thereafter, the solvent (ethanol and epichlorohydrin) was removed under reduced pressure. Next, 10 g of methyl isobutyl ketone (MIBK) was added to the contents from which the solvent had been removed and stirred, and then insoluble matters were removed.

  (2-2); The solvent was removed from the liquid obtained in (2-1) under reduced pressure to obtain 1.4 g (yield: 82.8%) of dibenzochrysene glycidyl ether as a yellow oil. As a result of subjecting the obtained dibenzochrysene glycidyl ether to LC / MS analysis, it was confirmed that 98% of 4-substituted dibenzochrysene glycidyl ether and the remaining trisubstituted dibenzochrysene glycidyl ether were contained.

Example 1 Production of dibenzochrysene derivative (1)
A dibenzochrysene derivative in which R ⁵ in the formula (C1) is represented by the formula (C21) was produced by the synthesis shown in the following scheme (S13) using the hydroxydibenzochrysene obtained in the above Synthesis Example 1.

  (1-1): 10 g (0.026 mol) of hydroxydibenzochrysene obtained in Synthesis Example 1 and 50 mg of phenothiazine (Kanto Chemical Co., Ltd.) were dissolved in 200 g of acetonitrile (manufactured by Wako Pure Chemical Industries, Ltd.). 18.5 g (0.2 mol) of acryloyl chloride (manufactured by Wako Pure Chemical Industries) and 26 g (0.26 mol) of triethylamine (manufactured by Kanto Chemical Co., Ltd.) were added dropwise and stirred for 6 hours at 25 ° C. Thereafter, 10 g of methanol was added dropwise. The reaction solution was washed with 800 g of ethyl acetate and 150 g of distilled water, washed twice with distilled water, and then the solvent was distilled off with an evaporator under reduced pressure. = Purified by silica gel column chromatography using a mixed solvent of 10/1 and dried under reduced pressure. To yield a brown powdery solid 9.8 g (62% yield).

  As a result of subjecting the obtained brown powdery solid to LC / MS analysis, a peak having an m / z of 626.1740 was recognized on the chart. As a result, the molecular weight of the product was identified as 608.1471 (Exact Mass) (a value obtained by subtracting the equivalent of one molecule of ammonium ion added according to the measurement conditions from the peak value). Therefore, a tetrasubstituted compound represented by the formula (C1-12) shown in the scheme (S13) was confirmed.

<Example 2> Production of dibenzochrysene derivative (2)
A dibenzochrysene derivative in which R ⁵ in formula (C1) is represented by formula (C22) was produced by the synthesis shown in the following scheme (S14) using hydroxydibenzochrysene obtained in Synthesis Example 1 described later.

  (1-1): 10 g (0.026 mol) of hydroxydibenzochrysene obtained in Synthesis Example 1 and 50 mg of phenothiazine (Kanto Chemical Co., Ltd.) were dissolved in 200 g of acetonitrile (manufactured by Wako Pure Chemical Industries, Ltd.). 20.9 g (0.2 mol) of methacryloyl chloride (manufactured by Wako Pure Chemical Industries) and 26 g (0.26 mol) of triethylamine (manufactured by Kanto Chemical Co., Ltd.) were added dropwise and stirred for 6 hours at 25 ° C. Thereafter, 10 g of methanol was added dropwise. The resulting reaction solution was washed with 800 g of ethyl acetate and 150 g of distilled water, washed twice with distilled water, and then the solvent was distilled off under reduced pressure using an evaporator. Purified by silica gel column chromatography using a mixed solvent of / ethyl acetate = 10/1 and dried under reduced pressure The go to give a brown powdery solid 12.1 g (70% yield).

  As a result of subjecting the obtained brown powdery solid to LC / MS analysis, a peak having an m / z of 682.2433 was observed on the chart. As a result, the molecular weight of the product was identified as 664.2097 (Exact Mass) (a value obtained by subtracting the equivalent of one molecule of ammonium ion added depending on the measurement conditions from the peak value). Therefore, the tetrasubstituted compound represented by the formula (C1-18) shown in the scheme (S14) was confirmed.

Example 3 Production of dibenzochrysene derivative (3)
Using the dibenzochrysene glycidyl ether obtained in Synthesis Example 2 to be described later, a dibenzochrysene derivative in which R ⁵ in formula (C1) is represented by formula (C31) was produced by the synthesis shown in the following scheme (S15). .

  (1-1): 5.0 g (0.0081 mol) of dibenzochrysene glycidyl ether obtained in Synthesis Example 2, 30 mg of phenothiazine (Kanto Chemical Co., Ltd.), and 60 mg of triphenylphosphine (Wako Pure Chemical Industries, Ltd.), Was dissolved in 50.0 g (0.7 mol) of acrylic acid (manufactured by Kanto Chemical Co., Inc.). Thereafter, 100 g of toluene (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the mixture was reacted on an oil bath at 90 ° C. for 10 hours. After adding 400 g of ethyl acetate and saturated sodium hydrogencarbonate aqueous solution to the obtained reaction liquid, the ethyl acetate phase was fractionated. Subsequently, the insoluble material was filtered off, and the ethyl acetate phase was washed with 100 g of distilled water, further concentrated under reduced pressure, and dried to obtain 3.5 g of a brown solid {approximate yield 48% (4 substitution product) Conversion)}.

As a result of subjecting the obtained brown powdery solid to LC / MS analysis, a peak having an m / z of 689.2324 was recognized on the chart. As a result, the molecular weight of the product was identified as 688.2309 (Exact Mass) (a value obtained by subtracting the proton equivalent added according to the measurement conditions from the peak value). Thus, a monosubstituted compound represented by the following formula (C1-19a) was confirmed.
Moreover, the peak whose m / z is 761.2550 was recognized. As a result, the molecular weight of the product was identified as 760.2520 (Exact Mass) (a value obtained by subtracting the proton equivalent added according to the measurement conditions from the peak value). Therefore, a disubstituted compound represented by the following formula (C1-21a) or the like was confirmed. The disubstituted compound is considered to include isomers represented by the above-described formulas (C1-20), (C1-21) and (C1-22).

Furthermore, a peak having an m / z of 833.2771 was observed. As a result, the molecular weight of the product was identified as 832.27 (Exact Mass) (a value obtained by subtracting the proton equivalent added depending on the measurement conditions from the peak value). Therefore, a trisubstituted compound represented by the following formula (C1-23a) was confirmed.
Moreover, the peak whose m / z is 905.22982 was recognized. As a result, the molecular weight of the product was identified as 904.22942 (Exact Mass) (a value obtained by subtracting the proton equivalent added according to the measurement conditions from the peak value). Therefore, a 4-substituted compound represented by the following formula (C1-24) was confirmed.

Example 4 Production of dibenzochrysene derivative (4)
Using the dibenzochrysene glycidyl ether obtained in Synthesis Example 2 described later, a dibenzochrysene derivative in which R ⁵ in formula (C1) is represented by formula (C32) was produced by the synthesis shown in the following scheme (S16). .

  (1-1): 5.0 g (0.0081 mol) of dibenzochrysene glycidyl ether obtained in Synthesis Example 2, 30 mg of phenothiazine (Kanto Chemical Co., Ltd.) and 60 mg of triphenylphosphine (Wako Pure Chemical Industries, Ltd.) After dissolving in 60.3 g (0.7 mol) of acid (manufactured by Wako Pure Chemical Industries, Ltd.), 100 g of toluene (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The reaction was carried out at 90 ° C. for 10 hours on an oil bath. After adding 400 g of ethyl acetate and saturated sodium hydrogencarbonate aqueous solution to the obtained reaction liquid, the ethyl acetate phase was fractionated. Subsequently, the insoluble material was filtered off, and the ethyl acetate phase was washed with 100 g of distilled water, further concentrated under reduced pressure, and dried to obtain 4.1 g of a brown solid {estimated yield 53% (4 substitution product) Conversion)}.

As a result of subjecting the obtained brown powdery solid to LC / MS analysis, a peak having an m / z of 703.2516 was observed on the chart. As a result, the molecular weight of the product was identified as 702.2465 (Exact Mass) (a value obtained by subtracting the proton equivalent added according to the measurement conditions from the peak value). Therefore, the monosubstituted compound represented by the following formula (C1-25a) was confirmed.
Moreover, the peak whose m / z is 7899.288 was recognized. As a result, the molecular weight of the product was identified as 788.2833 (Exact Mass) (a value obtained by subtracting the proton equivalent added according to the measurement conditions from the peak value). Therefore, a disubstituted compound represented by the following formula (C1-27a) or the like was confirmed. The disubstituted compound is considered to include isomers represented by the above-described formulas (C1-26), (C1-27) and (C1-28).

Furthermore, a peak having an m / z of 875.3271 was observed. As a result, the molecular weight of the product was specified as 874.3201 (Exact Mass) (a value obtained by subtracting the proton equivalent added according to the measurement conditions from the peak value). Therefore, a trisubstituted compound represented by the following formula (C1-29a) was confirmed.
Moreover, the peak whose m / z is 961.3716 was recognized. As a result, the molecular weight of the product was identified as 960.3568 (Exact Mass) (a value obtained by subtracting the proton equivalent added according to the measurement conditions from the peak value). Therefore, a 4-substituted compound represented by the following formula (C1-30) was confirmed.

Example 5 Production of dibenzochrysene derivative (5)
A dibenzochrysene derivative in which R ⁵ in formula (C1) is represented by formula (C4) was produced by the synthesis shown in the following scheme (S17) using hydroxydibenzochrysene obtained in Synthesis Example 1 described later.

  (1-1): 5 g (0.013 mol) of hydroxydibenzochrysene obtained in Synthesis Example 1, 12.3 g (0.10 mol) of allyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) and dimethyl sulfoxide (stock of Wako Pure Chemical Industries, Ltd.) Dissolved in 50 g). Then, 2.54 g (0.064 mol) of sodium hydroxide (Tosoh Corporation product name: Tosoh Pearl) was stirred at 80 ° C. for 18 hours in a nitrogen stream. After completion of the reaction, 300 g of ethyl acetate and 80 g of distilled water were added for washing. After washing with distilled water twice, the solvent was distilled off with an evaporator under reduced pressure. Purification by silica gel column chromatography using toluene and drying under reduced pressure gave 4.8 g of a brown powdery solid (yield 67%).

  As a result of subjecting the obtained brown powdery solid to LC / MS analysis, a peak having an m / z of 553.2471 was observed on the chart. As a result, the molecular weight of the product was identified as 552.2301 (Exact Mass) (a value obtained by subtracting the proton equivalent added according to the measurement conditions from the peak value). Therefore, a tetrasubstituted compound represented by the formula (C1-36) shown in the scheme (S17) was confirmed.

In addition, in this invention, it can restrict to what is shown to said specific Example, It can be set as the Example variously changed within the range of this invention according to the objective and the use.
That is, for example, hydrazine is allowed to act on a nitrodibenzochrysene obtained by nitration of dibenzochrysene under a catalyst to obtain aminodibenzochrysene. Further, sodium nitrite is allowed to act on aminodibenzochrysene in the presence of an acid to obtain a diazonium salt of dibenzochrysene. Furthermore, hydroxydibenzochrysene can be obtained by decomposing the obtained diazonium salt (described in Japanese Patent Application No. 2012-77951). Thus, the obtained hydroxy dibenzochrysene is mainly composed of hydroxy dibenzochrysene monosubstituted by a hydroxyl group and disubstituted hydroxydibenzochrysene (hydroxy dibenzochrynes obtained by Synthesis Example 1 described above). Chrysene is mainly a 4-substituted compound. For this reason, when aiming at a mono- and / or di-substituted dibenzochrysene derivative, hydroxydibenzochrysene obtained by the above-mentioned process can be used.

前記式（Ｃ１）中、Ｒ^１〜Ｒ^４のうちの１〜３つの基が−ＯＲ^５で表され、
前記Ｒ^５は、−ＣＯ−を含み、−ＯＨを含まず、且つ、末端に重合性不飽和結合を有する炭素数２〜１２の基であり、
前記−ＯＲ ^５ で表される基以外の基がヒドロキシル基である。
［２］請求項２に記載の化合物は、下記式（Ｃ１）で表されることを要旨とする。

前記式（Ｃ１）中、Ｒ ^１ 〜Ｒ ^４ のうちの１〜３つの基が−ＯＲ ^５ で表され、
前記Ｒ ^５ は、−ＣＯ−を含み、−ＯＨを含まず、且つ、末端に重合性不飽和結合を有する炭素数２〜１２の基であり、
前記−ＯＲ ^５ で表される基以外の基がグリシジルエーテル基である。
［３］請求項３に記載の化合物は、下記式（Ｃ１）で表されることを要旨とする。

前記式（Ｃ１）中、Ｒ ^１ 〜Ｒ ^４ のうちの少なくとも１つの基が−ＯＲ ^５ で表され、
前記Ｒ ^５ は、−ＣＯ−を含み、−ＯＨを含まず、且つ、末端に重合性不飽和結合を有する炭素数２〜１２の基であり、
前記少なくとも１つの基以外のＲ ^１ 〜Ｒ ^４ は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基であり、
前記１価の基は、ヒドロキシル基、グリシジルエーテル基、−Ｏ−Ｃ _ｎ Ｈ _２ｎ −ＯＨで表される基（但しｎ＝２〜１２）、−Ｏ−（Ｃ _ｎ Ｈ _２ｎ −Ｏ） _ｍ −Ｈで表される基（但しｎ＝２〜１２、ｍ＝２〜６）、炭素数１〜１２のアルキル基、炭素数３〜１２のシクロアルキル基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、炭素数２〜１２のアルケニル基、ハロゲン置換された炭素数１〜１２のアルキル基、ハロゲン置換された炭素数３〜１２のシクロアルキル基、ハロゲン置換された炭素数６〜１２のアリール基、ハロゲン置換された炭素数７〜１２のアラルキル基、ハロゲン置換された炭素数２〜１２のアルケニル基、ニトロ基、及び、アミノ基からなる群から選ばれる。 In order to solve the above problems,
[1] The gist of the compound of claim 1 is represented by the following formula (C1).

In the formula (C1), ^{1 to} 3 groups out of R ^{1 to} R ⁴ are represented by —OR ⁵ ,
R ⁵ is a group having 2 to 12 carbon atoms that includes —CO—, does not include —OH, and has a polymerizable unsaturated bond at a terminal;
A group other than the group represented by -OR ⁵ is a hydroxyl group .
[2] The gist of the compound of claim 2 is represented by the following formula (C1).

In the formula (C1), ^{1 to} 3 groups out of R ^{1 to} R ⁴ are represented by —OR ⁵ ,
R ⁵ is a group having 2 to 12 carbon atoms that contains —CO—, does not contain —OH, and has a polymerizable unsaturated bond at the terminal;
A group other than the group represented by -OR ⁵ is a glycidyl ether group.
[3] The gist of the compound of claim 3 is represented by the following formula (C1).

In the formula (C1), at least one group of R ^{1 to} R ⁴ is represented by —OR ⁵ ,
R ⁵ is a group having 2 to 12 carbon atoms that contains —CO—, does not contain —OH, and has a polymerizable unsaturated bond at the terminal;
R ^{1 to} R ⁴ other than the at least one group are each independently H (hydrogen atom), X (halogen atom) or a monovalent group,
The monovalent group is a hydroxyl group, a glycidyl ether group, a group represented by —O—C _n H _2n —OH (where n = 2 to 12), —O— (C _n H _2n —O) _m —. A group represented by H (where n = 2 to 12, m = 2 to 6), an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, carbon Aralkyl group having 7 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, alkyl group having 1 to 12 carbon atoms substituted with halogen, cycloalkyl group having 3 to 12 carbon atoms substituted with halogen, carbon number substituted with halogen It is selected from the group consisting of 6 to 12 aryl groups, halogen-substituted aralkyl groups having 7 to 12 carbon atoms, halogen-substituted alkenyl groups having 2 to 12 carbon atoms, nitro groups, and amino groups.

[4] The compound according to claim 4 is the compound according to claim 3 , wherein in the formula (C1), 2 to 4 groups of R ^{1 to} R ⁴ are represented by —OR ^5. Is the gist.
[5] The compound according to claim 5 is the compound according to any one of claims 1 to 4, wherein R ⁵ is represented by the following formula (C2), the following formula (C5), or the following formula (C6). The gist of this is
_{^{-CO- (CH 2) n -C (}} R 6) = CH 2 ··· (C2)
The R ⁶ is H (hydrogen atom) or a methyl group, n in the formula (C2) is n = 0 to 9 when the R ⁶ is H, and the R ⁶ is a methyl group n = 0~8 der Ru to.
_{^{- (CH 2) n -OCO-}} C (R 9) = CH 2 ··· (C5)
The R ⁹ is H (hydrogen atom) or a methyl group, n in the formula (C5) is n = 1 to 9 when the R ⁹ is H, and the R ⁹ is a methyl group N = 1-8.
—R ¹⁰ —CH ₂ —OCO—C (R ¹¹ ) ═CH ₂ ... (C6)
R ¹⁰ is represented by the following formula (C61) or the following formula (C62),
_{- (C 2 H 4 -O-)} n - ··· (C61)
_{- (C 3 H 6 -O-)} l - ··· (C62)
R ¹¹ is H (hydrogen atom) or a methyl group, and when R ¹¹ is H, n in the formula (C61) is n = 1 to 4, and l in the formula (C62) is 1 = 1 to 2, and when R ¹¹ is a methyl group, n in the formula (C61) is n = 1 to 3, and l in the formula (C62) is l = 1 to 2.

前記式（Ｃ１）中、Ｒ ^１ 〜Ｒ ^４ のうちの１〜３つの基が−ＯＲ ^５ で表され、
前記Ｒ ^５ は、下記式（Ｃ４）又は（Ｃ９）で表されるとともに、末端に重合性不飽和結合を有する炭素数２〜１２の基であり、
前記−ＯＲ ^５ で表される基以外の基がヒドロキシル基である。
−（ＣＨ _２ ） _ｎ −Ｃ（Ｒ ^８ ）＝ＣＨ _２ ・・・（Ｃ４）
前記Ｒ ^８ はＨ（水素原子）又はメチル基であり、前記（Ｃ４）におけるｎは、前記Ｒ ^８ がＨである場合にｎ＝０〜１０であり、前記Ｒ ^８ がメチル基である場合にｎ＝０〜９である。
−Ｒ ^１５ −ＣＨ _２ −Ｃ（Ｒ ^１６ ）＝ＣＨ _２ ・・・（Ｃ９）
前記Ｒ ^１５ は、下記式（Ｃ９１）又は下記式（Ｃ９２）で表され、
−（Ｃ _２ Ｈ _４ −Ｏ−） _ｎ − ・・・（Ｃ９１）
−（Ｃ _３ Ｈ _６ −Ｏ−） _ｌ − ・・・（Ｃ９２）
前記Ｒ ^１６ はＨ（水素原子）又はメチル基であり、前記Ｒ ^１６ がＨである場合に、前記式（Ｃ９１）のｎはｎ＝１〜４であり、前記式（Ｃ９２）のｌはｌ＝１〜３であり、前記Ｒ ^１６ がメチル基である場合に、前記式（Ｃ９１）のｎはｎ＝１〜４であり、前記式（Ｃ９２）のｌはｌ＝１〜２である。
［７］請求項７に記載の化合物は、下記式（Ｃ１）で表されることを要旨とする。

前記式（Ｃ１）中、Ｒ ^１ 〜Ｒ ^４ のうちの１〜３つの基が−ＯＲ ^５ で表され、
前記Ｒ ^５ は、下記式（Ｃ４）又は（Ｃ９）で表されるとともに、末端に重合性不飽和結合を有する炭素数２〜１２の基であり、
前記−ＯＲ ^５ で表される基以外の基がグリシジルエーテル基である。
−（ＣＨ _２ ） _ｎ −Ｃ（Ｒ ^８ ）＝ＣＨ _２ ・・・（Ｃ４）
前記Ｒ ^８ はＨ（水素原子）又はメチル基であり、前記（Ｃ４）におけるｎは、前記Ｒ ^８ がＨである場合にｎ＝０〜１０であり、前記Ｒ ^８ がメチル基である場合にｎ＝０〜９である。
−Ｒ ^１５ −ＣＨ _２ −Ｃ（Ｒ ^１６ ）＝ＣＨ _２ ・・・（Ｃ９）
前記Ｒ ^１５ は、下記式（Ｃ９１）又は下記式（Ｃ９２）で表され、
−（Ｃ _２ Ｈ _４ −Ｏ−） _ｎ − ・・・（Ｃ９１）
−（Ｃ _３ Ｈ _６ −Ｏ−） _ｌ − ・・・（Ｃ９２）
前記Ｒ ^１６ はＨ（水素原子）又はメチル基であり、前記Ｒ ^１６ がＨである場合に、前記式（Ｃ９１）のｎはｎ＝１〜４であり、前記式（Ｃ９２）のｌはｌ＝１〜３であり、前記Ｒ ^１６ がメチル基である場合に、前記式（Ｃ９１）のｎはｎ＝１〜４であり、前記式（Ｃ９２）のｌはｌ＝１〜２である。 [6] The gist of the compound of claim 6 is represented by the following formula (C1).

In the formula (C1), ^{1 to} 3 groups out of R ^{1 to} R ⁴ are represented by —OR ⁵ ,
R ⁵ is a group having 2 to 12 carbon atoms represented by the following formula (C4) or (C9) and having a polymerizable unsaturated bond at the end;
A group other than the group represented by -OR ⁵ is a hydroxyl group.
_{^{- (CH 2) n -C (}} R 8) = CH 2 ··· (C4)
The R ⁸ is H (hydrogen atom) or a methyl group, n in the (C4) is n = 0 to 10 when the R ⁸ is H, and the R ⁸ is a methyl group. n = 0-9.
_{^{-R 15 -CH 2 -C (R 16}} ) = CH 2 ··· (C9)
R ¹⁵ is represented by the following formula (C91) or the following formula (C92),
_{- (C 2 H 4 -O-)} n - ··· (C91)
_{- (C 3 H 6 -O-)} l - ··· (C92)
R ¹⁶ is H (hydrogen atom) or a methyl group, and when R ¹⁶ is H, n in the formula (C91) is n = 1 to 4, and l in the formula (C92) is 1 = 1-3, and when R ¹⁶ is a methyl group, n in the formula (C91) is n = 1-4, and l in the formula (C92) is l = 1-2.
[7] The gist of the compound of claim 7 is represented by the following formula (C1).

In the formula (C1), ^{1 to} 3 groups out of R ^{1 to} R ⁴ are represented by —OR ⁵ ,
R ⁵ is a group having 2 to 12 carbon atoms represented by the following formula (C4) or (C9) and having a polymerizable unsaturated bond at the end;
A group other than the group represented by -OR ⁵ is a glycidyl ether group.
_{^{- (CH 2) n -C (}} R 8) = CH 2 ··· (C4)
The R ⁸ is H (hydrogen atom) or a methyl group, n in the (C4) is n = 0 to 10 when the R ⁸ is H, and the R ⁸ is a methyl group. n = 0-9.
_{^{-R 15 -CH 2 -C (R 16}} ) = CH 2 ··· (C9)
R ¹⁵ is represented by the following formula (C91) or the following formula (C92),
_{- (C 2 H 4 -O-)} n - ··· (C91)
_{- (C 3 H 6 -O-)} l - ··· (C92)
R ¹⁶ is H (hydrogen atom) or a methyl group, and when R ¹⁶ is H, n in the formula (C91) is n = 1 to 4, and l in the formula (C92) is 1 = 1-3, and when R ¹⁶ is a methyl group, n in the formula (C91) is n = 1-4, and l in the formula (C92) is l = 1-2.

前記式（Ｃ１）中、Ｒ ^１ 〜Ｒ ^４ のうちの少なくとも１つの基が−ＯＲ ^５ で表され、
前記Ｒ ^５ は、下記式（Ｃ４）又は（Ｃ９）で表されるとともに、末端に重合性不飽和結合を有する炭素数２〜１２の基であり、
前記少なくとも１つの基以外のＲ ^１ 〜Ｒ ^４ は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基であり、
前記１価の基は、ヒドロキシル基、グリシジルエーテル基、−Ｏ−Ｃ _ｎ Ｈ _２ｎ −ＯＨで表される基（但しｎ＝２〜１２）、−Ｏ−（Ｃ _ｎ Ｈ _２ｎ −Ｏ） _ｍ −Ｈで表される基（但しｎ＝２〜１２、ｍ＝２〜６）、炭素数１〜１２のアルキル基、炭素数３〜１２のシクロアルキル基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、炭素数２〜１２のアルケニル基、ハロゲン置換された炭素数１〜１２のアルキル基、ハロゲン置換された炭素数３〜１２のシクロアルキル基、ハロゲン置換された炭素数６〜１２のアリール基、ハロゲン置換された炭素数７〜１２のアラルキル基、ハロゲン置換された炭素数２〜１２のアルケニル基、ニトロ基、及び、アミノ基からなる群から選ばれる。
−（ＣＨ _２ ） _ｎ −Ｃ（Ｒ ^８ ）＝ＣＨ _２ ・・・（Ｃ４）
前記Ｒ ^８ はＨ（水素原子）又はメチル基であり、前記（Ｃ４）におけるｎは、前記Ｒ ^８ がＨである場合にｎ＝０〜１０であり、前記Ｒ ^８ がメチル基である場合にｎ＝０〜９である。
−Ｒ ^１５ −ＣＨ _２ −Ｃ（Ｒ ^１６ ）＝ＣＨ _２ ・・・（Ｃ９）
前記Ｒ ^１５ は、下記式（Ｃ９１）又は下記式（Ｃ９２）で表され、
−（Ｃ _２ Ｈ _４ −Ｏ−） _ｎ − ・・・（Ｃ９１）
−（Ｃ _３ Ｈ _６ −Ｏ−） _ｌ − ・・・（Ｃ９２）
前記Ｒ ^１６ はＨ（水素原子）又はメチル基であり、前記Ｒ ^１６ がＨである場合に、前記式（Ｃ９１）のｎはｎ＝１〜４であり、前記式（Ｃ９２）のｌはｌ＝１〜３であり、前記Ｒ ^１６ がメチル基である場合に、前記式（Ｃ９１）のｎはｎ＝１〜４であり、前記式（Ｃ９２）のｌはｌ＝１〜２である。
［９］請求項９に記載の化合物は、請求項８に記載の化合物において、前記式（Ｃ１）中、Ｒ ^１ 〜Ｒ ^４ のうちの２〜４つの基が−ＯＲ ^５ で表されることを要旨とする。 [8] The gist of the compound of claim 8 is represented by the following formula (C1).

In the formula (C1), at least one group of R ^{1 to} R ⁴ is represented by —OR ⁵ ,
R ⁵ is a group having 2 to 12 carbon atoms represented by the following formula (C4) or (C9) and having a polymerizable unsaturated bond at the end;
R ^{1 to} R ⁴ other than the at least one group are each independently H (hydrogen atom), X (halogen atom) or a monovalent group,
The monovalent group is a hydroxyl group, a glycidyl ether group, a group represented by —O—C _n H _2n —OH (where n = 2 to 12), —O— (C _n H _2n —O) _m —. A group represented by H (where n = 2 to 12, m = 2 to 6), an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, carbon Aralkyl group having 7 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, alkyl group having 1 to 12 carbon atoms substituted with halogen, cycloalkyl group having 3 to 12 carbon atoms substituted with halogen, carbon number substituted with halogen It is selected from the group consisting of 6 to 12 aryl groups, halogen-substituted aralkyl groups having 7 to 12 carbon atoms, halogen-substituted alkenyl groups having 2 to 12 carbon atoms, nitro groups, and amino groups.
_{^{- (CH 2) n -C (}} R 8) = CH 2 ··· (C4)
The R ⁸ is H (hydrogen atom) or a methyl group, n in the (C4) is n = 0 to 10 when the R ⁸ is H, and the R ⁸ is a methyl group. n = 0-9.
_{^{-R 15 -CH 2 -C (R 16}} ) = CH 2 ··· (C9)
R ¹⁵ is represented by the following formula (C91) or the following formula (C92),
_{- (C 2 H 4 -O-)} n - ··· (C91)
_{- (C 3 H 6 -O-)} l - ··· (C92)
R ¹⁶ is H (hydrogen atom) or a methyl group, and when R ¹⁶ is H, n in the formula (C91) is n = 1 to 4, and l in the formula (C92) is 1 = 1-3, and when R ¹⁶ is a methyl group, n in the formula (C91) is n = 1-4, and l in the formula (C92) is l = 1-2.
[9] The compound according to claim 9 is the compound according to claim 8, wherein in the formula (C1), 2 to 4 groups of R ^{1 to} R ⁴ are represented by —OR ^5. Is the gist.

前記式（Ｃ１）中、Ｒ ^１ 〜Ｒ ^４ のうちの１〜３つの基が−ＯＲ ^５ で表され、
前記Ｒ ^５ は、−ＯＨを含まず、且つ、末端に重合性不飽和結合を有する炭素数２又は３の基であり、
前記−ＯＲ ^５ で表される基以外の基がヒドロキシル基である。
［１１］請求項１１に記載の化合物は、下記式（Ｃ１）で表されることを要旨とする。

前記式（Ｃ１）中、Ｒ ^１ 〜Ｒ ^４ のうちの１〜３つの基が−ＯＲ ^５ で表され、
前記Ｒ ^５ は、−ＯＨを含まず、且つ、末端に重合性不飽和結合を有する炭素数２又は３の基であり、
前記−ＯＲ ^５ で表される基以外の基がグリシジルエーテル基である。 [10] The gist of the compound of claim 10 is represented by the following formula (C1).

In the formula (C1), ^{1 to} 3 groups out of R ^{1 to} R ⁴ are represented by —OR ⁵ ,
R ⁵ is a group having 2 or 3 carbon atoms which does not contain —OH and has a polymerizable unsaturated bond at the terminal;
A group other than the group represented by -OR ⁵ is a hydroxyl group.
[11] The gist of the compound of claim 11 is represented by the following formula (C1).

In the formula (C1), ^{1 to} 3 groups out of R ^{1 to} R ⁴ are represented by —OR ⁵ ,
R ⁵ is a group having 2 or 3 carbon atoms which does not contain —OH and has a polymerizable unsaturated bond at the terminal;
A group other than the group represented by -OR ⁵ is a glycidyl ether group.

前記式（Ｃ１）中、Ｒ ^１ 〜Ｒ ^４ のうちの少なくとも１つの基が−ＯＲ ^５ で表され、
前記Ｒ ^５ は、−ＯＨを含まず、且つ、末端に重合性不飽和結合を有する炭素数２又は３の基であり、
前記少なくとも１つの基以外のＲ ^１ 〜Ｒ ^４ は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基であり、
前記１価の基は、ヒドロキシル基、グリシジルエーテル基、−Ｏ−Ｃ _ｎ Ｈ _２ｎ −ＯＨで表される基（但しｎ＝２〜１２）、−Ｏ−（Ｃ _ｎ Ｈ _２ｎ −Ｏ） _ｍ −Ｈで表される基（但しｎ＝２〜１２、ｍ＝２〜６）、炭素数１〜１２のアルキル基、炭素数３〜１２のシクロアルキル基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、炭素数２〜１２のアルケニル基、ハロゲン置換された炭素数１〜１２のアルキル基、ハロゲン置換された炭素数３〜１２のシクロアルキル基、ハロゲン置換された炭素数６〜１２のアリール基、ハロゲン置換された炭素数７〜１２のアラルキル基、ハロゲン置換された炭素数２〜１２のアルケニル基、ニトロ基、及び、アミノ基からなる群から選ばれる。
［１３］請求項１３に記載の化合物は、請求項１２に記載の化合物において、前記式（Ｃ１）中、Ｒ ^１ 〜Ｒ ^４ のうちの２〜４つの基が−ＯＲ ^５ で表されることを要旨とする。 [12] The gist of the compound of claim 12 is represented by the following formula (C1).

In the formula (C1), at least one group of R ^{1 to} R ⁴ is represented by —OR ⁵ ,
R ⁵ is a group having 2 or 3 carbon atoms which does not contain —OH and has a polymerizable unsaturated bond at the terminal;
R ^{1 to} R ⁴ other than the at least one group are each independently H (hydrogen atom), X (halogen atom) or a monovalent group,
The monovalent group is a hydroxyl group, a glycidyl ether group, a group represented by —O—C _n H _2n —OH (where n = 2 to 12), —O— (C _n H _2n —O) _m —. A group represented by H (where n = 2 to 12, m = 2 to 6), an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, carbon Aralkyl group having 7 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, alkyl group having 1 to 12 carbon atoms substituted with halogen, cycloalkyl group having 3 to 12 carbon atoms substituted with halogen, carbon number substituted with halogen It is selected from the group consisting of 6 to 12 aryl groups, halogen-substituted aralkyl groups having 7 to 12 carbon atoms, halogen-substituted alkenyl groups having 2 to 12 carbon atoms, nitro groups, and amino groups.
[13] The compound according to claim 13 is the compound according to claim 12, wherein in the formula (C1), 2 to 4 groups of R ^{1 to} R ⁴ are represented by —OR ^5. Is the gist.

[14] The compound according to claim 14 is a monomer for improving thermal conductivity in the compound according to any one of claims 1 to 13, for improving the thermal conductivity of the resulting polymer. It is a summary.
[15] The gist of the polymer according to claim 15 is obtained by using the compound according to any one of claims 1 to 14 .
[16] The curing agent according to claim 16 includes the compound according to any one of claims 1 to 14.
[17] The gist of the crosslinking agent according to claim 17 includes the compound according to any one of claims 1 to 14.

式（Ｃ１）中、Ｒ^１〜Ｒ^４のうちの少なくとも１つの基が−ＯＲ^５で表され、
少なくとも１つの基のＲ^５は、末端に重合性不飽和結合を有する炭素数２〜１２の基であり、
少なくとも１つの基以外のＲ^１〜Ｒ^４は、各々独立に、Ｈ（水素原子）、Ｘ（ハロゲン原子）又は１価の基である。
即ち、本発明の化合物として後述する式（Ｃ１−１）〜式（Ｃ１−６）で表される化合物が含まれる。 [1] Compound The compound is represented by the following formula (C1).

In formula (C1), at least one group of R ^{1 to} R ⁴ is represented by —OR ⁵ ,
At least one group R ⁵ is a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at a terminal;
R ^{1 to} R ⁴ other than at least one group are each independently H (hydrogen atom), X (halogen atom) or a monovalent group.
That is, compounds represented by formula (C1-1) to formula (C1-6) described later are included as the compounds of the present invention.

Although not included in the present invention, R ⁵ may be a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at the terminal and including —CO— and —OH. Specifically, R ⁵ can be a group represented by the following formula (C3).
_{-CH 2 -CH (OH) -CH 2} -OCO- (CH 2) n -C (R 7) = CH 2
... (C3)
R ^{7 in} formula (C3) is H (hydrogen atom) or a methyl group. When R ⁷ is H (hydrogen atom), n is n = 0-6. Further, n in the case ^{R 7} is a methyl group is n = 0 to 5.

Reference Example 1 Production of dibenzochrysene derivative (3)
Using the dibenzochrysene glycidyl ether obtained in Synthesis Example 2 to be described later, a dibenzochrysene derivative in which R ⁵ in formula (C1) is represented by formula (C31) was produced by the synthesis shown in the following scheme (S15). .

Reference Example 2 Production of dibenzochrysene derivative (4)
Using the dibenzochrysene glycidyl ether obtained in Synthesis Example 2 described later, a dibenzochrysene derivative in which R ⁵ in formula (C1) is represented by formula (C32) was produced by the synthesis shown in the following scheme (S16). .

<Example 3 > Production of dibenzochrysene derivative (5)
A dibenzochrysene derivative in which R ⁵ in formula (C1) is represented by formula (C4) was produced by the synthesis shown in the following scheme (S17) using hydroxydibenzochrysene obtained in Synthesis Example 1 described later.

Claims (7)

A compound represented by the following formula (C1).

In the formula (C1), at least one group of R ^{1 to} R ⁴ is represented by —OR ⁵ ,
R ⁵ of the at least one group is a group having 2 to 12 carbon atoms having a polymerizable unsaturated bond at a terminal;
R ^{1 to} R ⁴ other than the at least one group are each independently H (hydrogen atom), X (halogen atom) or a monovalent group. The compound according to claim 1, wherein R ⁵ includes —CO—. The compound according to claim 2, wherein R ⁵ is represented by the following formula (C2).
^{_{-CO- (CH 2) n -C (}} R 6) = CH 2 ··· (C2)
R ⁶ represents H (hydrogen atom) or a methyl group. The compound according to claim 1, wherein R ⁵ includes —CO— and —OH. The compound according to claim 4, wherein R ⁵ is represented by the following formula (C3).
_{-CH 2 -CH (OH) -CH 2} -OCO- (CH 2) n -C (R 7) = CH 2
... (C3)
R ⁷ is H (hydrogen atom) or a methyl group. The compound according to claim 1, wherein R ⁵ is represented by the following formula (C4).
^{_{- (CH 2) n -C (}} R 8) = CH 2 ··· (C4)
R ⁸ is H (hydrogen atom) or a methyl group.   A polymer obtained by using the compound according to any one of claims 1 to 6.