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Compound and polymer compound containing the compound

外国特許コード F210010538
整理番号 K11205WO
掲載日 2021年8月2日
出願国 アメリカ合衆国
出願番号 201916977128
公報番号 20210002284
出願日 平成31年3月4日(2019.3.4)
公報発行日 令和3年1月7日(2021.1.7)
国際出願番号 JP2019008463
国際公開番号 WO2019172200
国際出願日 平成31年3月4日(2019.3.4)
国際公開日 令和元年9月12日(2019.9.12)
優先権データ
  • 特願2018-039162 (2018.3.5) JP
  • 2019JP08463 (2019.3.4) WO
発明の名称 (英語) Compound and polymer compound containing the compound
発明の概要(英語) Provided is a compound having higher fluorescence quantum yield and higher optical stability than a conventional FLAP and a polymer compound containing the compound.
-
- A: seven or eight-membered ring structure,
- Y1,Y2,Y3: halogen atom or the like,
- a1: number of Y1, a2: number of Y2,
- B: number of Y3,
- 0≤m and n≤3: when 1≤m≤3, Y1 may be substituted with a structure portion defined by m, when 1≤n≤3, Y2 may be substituted with a structure portion defined by n, and
- B1, B2: Formulas (2-1) to (2-3).
-
- C1, C2, C3: structure containing a cyclic hydrocarbon compound,
- D1, D2, D3: substructure that inhibits aggregation,
- E1, E2, E3: polymerizable substructure,
- Z1: hydrogen atom or the like,
- c: number of substituent groups Z1,
- Z2, Z3: hydrogen atom or the like, and may form a ring with C2.
従来技術、競合技術の概要(英語) BACKGROUND ART
Functional materials have been developed for various uses in accordance with the characteristics of the functional material, and as an example thereof, attempts to visualize mechanical stress such as compression, expansion, bending, or the like applied on a material have been made.
As a method for visualizing mechanical stress, visualization using dispersion of excimers (see Non-Patent Literature 1), visualization using binding cleavage of chromatic molecules (see Non-Patent Literature 2), visualization using energy transform of chemical light emission (see Non-Patent Literature 3), visualization using emission of small molecules (see Non-Patent Literature 4), and the like are known.
Further, a mechanochromic material made of a polymer having a repetition unit of a urethane structure or an ester structure in which diarylbibenzofuranone structure is urethane-bound or ester-bound is known (see Patent Literature 1).
Synthetic π-conjugated molecules have been used as a composition of dyes or pigments, aromatic polymers, or optical storage material for a long time and, in recent years, have been widely and practically used as a form of organic EL photodynamic therapy agents, fluorescent probes, or the like. In general, since synthetic π-conjugated molecules are made of rigid aromatic rings and multiple bonds (mainly, sp2 carbon), a significant majority of them necessarily have rigid structure.
Such rigid structure has many advantages also in the physical property, for example, an intended shape of a molecular framework can be synthesized, and because of small structure deformation, the structure exhibits a slow non-radiometric deactivation process and high light emission efficiency. On the other hand, it can also be considered that a rigid fundamental molecular framework makes it difficult to transform the physical property caused by flexibility of the structure in a similar manner to an inorganic material, and only the expression of a static physical property is reached. Thus, the present inventors create a compound having condensed-ring luminescent anthraceneimide as two rigid “wings” at opposed positions of flexible conjugated eight-membered ring (cyclooctatetraene) as illustrated in FIG. 1A. This compound exhibits inversion behavior between a V-form and a Λ-form in response to the motion of the eight-membered ring and emits blue light in a V-form state and green light in a planar state due to a change of electronic structure involved by the motion of the steric structure, as illustrated in FIG. 1B (see Non-Patent Literatures 5 and 6).
By using the compound described above, it is possible to visually indicate the degree of a mechanical stimulation (mechanical stress) applied on a material by means of a change of the light emission color. As a visualization technology using the compound described above, for example, the present inventors have found that, by dispersing the compound described above in an adhesive agent, it is possible to visualize curing process of the adhesive agent and, in addition, determine a portion of insufficient curing in a contactless manner (see Patent Literature 2).
Further, the present inventors have found (i) that, since a mechanochromic resin in which a mechanochromic light-emitting material represented by the following Formula (P1) or (P2) is cross-linked to a polymer chain changes the light emission color thereof quickly and reversibly due to expansion and compression, stress applied to a material can be visualized in real time and (ii) that, although synthesis of a mechanochromic resin is difficult with mere introduction of a polymerizable group to anthraceneimide dimers or naphthaleneimide dimers disclosed in Non-Patent Literatures 5 to 7, a mechanochromic resin in which a mechanochromic light-emitting material is cross-linked can be synthesized by introducing substituent group that inhibits aggregation between anthraceneimide dimers or naphthaleneimide dimers and the polymerizable group (see Patent Literature 3).
(In the formula, Y1 and Y2 denote substituent groups that inhibit aggregation of a mechanochromic light-emitting material expressed by Formula (1) and may be the same or may be different. Z1 and Z2 denote polymerizable groups and may be the same or may be different. Note that elements Y1 and Y2 and elements Z1 and Z2 in Formulas (P1) and (P2) are different from elements Y1 and Y2 and an element Z of the present invention described later.)
特許請求の範囲(英語) [claim1]
1. A compound represented by a following general Formula (1):
wherein in general Formula (1),
A denotes a seven-membered ring or eight-membered ring structure that may have a substituent group and forms a conjugated system with a benzene ring bound to A,
Y1 and Y2 each denote, independently, a substituent group selected from a halogen atom, an aliphatic hydrocarbon group with 1-20 carbons that may have a substituent group, an aryl group with 6-20 carbons that may have a substituent group, an alkoxy group with 1-10 carbons that may have a substituent group, an cyano group, and a heterocyclic compound group having 5-8 atoms forming a ring, and when a plurality of substituent groups Y1 and Y2 are provided, respective substituent groups may be the same as each other or may be different from each other,
a1 denotes the number of the substituent groups Y1, and a2 denotes the number of the substituent groups Y2,
Y3 denotes a substituent group selected from a halogen atom, an alkyl group with 1-20 carbons that may have a substituent group, an alkynyl group with 2-20 carbons that may have a substituent group, an aryl group with 6-20 carbons that may have a substituent group, an alkoxy group with 1-10 carbons that may have a substituent group, a carboxylic acid ester group with 2-20 carbons that may have a substituent group, a carboxyl group, a hydroxyl group, and a cyano group, when a plurality of substituent groups Y3 are provided, respective substituent groups may be the same as each other or may be different from each other,
b denotes the number of the substituent groups Y3,
m and n each denote, independently, an integer greater than or equal to 0 and less than or equal to 3, when m is an integer greater than or equal to 1 and less than or equal to 3, Y1 may be substituted with a structure portion defined by m, and similarly, when n is an integer greater than or equal to 1 and less than or equal to 3, Y2 may be substituted with a structure portion defined by n, and
B1 and B2 each denote, independently, any of the structures represented by general Formulas (2-1) to (2-3):
wherein in general Formulas (2-1) to (2-3),
C1 denotes a structure containing a cyclic hydrocarbon compound,
C2 and C3 each denote a structure containing a cyclic hydrocarbon compound but may have no structure containing a cyclic hydrocarbon compound, and when C2 and C3 have no structure containing a cyclic hydrocarbon compound, D2, D3, E2, and E3 are arranged in a framework of a compound represented by general Formula (1),
D1, D2, and D3 each denote a substructure that inhibits aggregation,
E2, and E3 each denote a polymerizable substructure,
Z1 each denote, independently, a substituent group selected from a hydrogen atom, a halogen atom, an alkyl group with 1-20 carbons that may have a substituent group, an alkynyl group with 2-20 carbons that may have a substituent group, an aryl group with 6-20 carbons that may have a substituent group, an alkoxy group with 1-10 carbons that may have a substituent group, and a cyano group and may form a ring with C1, and when a plurality of substituent groups Z1 are provided, respective substituent groups may be the same as each other or may be different from each other,
c denotes the number of substituent groups Z1, and
Z2 and Z3 each denote, independently, a substituent group selected from a hydrogen atom, a halogen atom, an alkyl group with 1-20 carbons that may have a substituent group, an alkynyl group with 2-20 carbons that may have a substituent group, an aryl group with 6-20 carbons that may have a substituent group, an alkoxy group with 1-10 carbons that may have a substituent group, and a cyano group, and Z2 and Z3 may each form a ring with C2, independently.

[claim2]
2. The compound according to claim 1, wherein in the general Formula (1), the A is represented by general Formula (3) or (4):
wherein in general Formula (4), Q denotes an O atom, an S atom, a Se atom, or an N atom or a P atom having an alkyl group as a substituent group.

[claim3]
3. The compound according to claim 1, wherein in the general Formula (1), the B1 and B2 have any structure of general Formulas (5-1) to (5-3):
wherein Z4 in general Formula (5-2) is the same as the Z2 and Z3.

[claim4]
4. The compound according to claim 1, wherein the E1, E2, and E3 each denote a polymerizable substituent group.

[claim5]
5. The compound according to claim 1, wherein the D1, D2, and D3 have any of following structures:
wherein R1 to R7 each denote H, a linear, branched, or cyclic alkyl group with 1-20 carbons, an aryl group with 6-20 carbons, F, Cl, Br, I, CF3, CCl3, CN, or OCH3, and R1 to R7 may be the same or different.

[claim6]
6. The compound according to claim 1, wherein the E1, E2, and E3 are any of the Formulas (E-1) to (E-18):
wherein in the Formulas (E-12) and (E-13), X denotes amide or ester but may not be included, R1 in the Formulas (E-12) and (E-13) denotes H, a linear, branched, or cyclic alkyl group with 1-20 carbons, an aryl group with 6-20 carbons, F, Cl, Br, I, CF3, CN, or OCH2, R in Formulas (E-1) to (E-18) denotes a linear, branched, or cyclic alkyl group with 1-20 carbons or an aryl group with 6-20 carbons, R in Formulas (E-1) to (E-11) may not be included, and each filled circle represents D1, D2, or D3.

[claim7]
7. The compound according to claim 3, wherein in the general Formula (1), the B1 and B2 have any of structures of the general Formulas (5-1) and (5-2).

[claim8]
8. The compound according to claim 3,
wherein in the general Formula (1), the B1 and B2 have a structure of the general Formula (5-3), and
wherein m and n of a compound represented by the general Formula (1) are 0 or 3.

[claim9]
9. The compound according to claim 1, wherein in the general Formula (1),
the a1
denotes an integer of 0 to 3 when m is 0, and
denotes an integer that Y1 can be substituted in accordance with the number 0 to m when m is an integer greater than or equal to 1 and less than or equal to 3,
the a2
denotes an integer of 0 to 3 when n is 0, and
denotes an integer that Y2 can be substituted in accordance with the number 0 to n when n is an integer greater than or equal to 1 and less than or equal to 3, and
the b denotes an integer greater than or equal to 0 and less than or equal to 4,

[claim10]
10. The compound according to claim 2, wherein in the general Formula (1), the A is the general Formula (4).

[claim11]
11. The compound according to claim 1, wherein in the general Formula (1), the b is an integer greater than or equal to 1 and less than or equal to 4.

[claim12]
12. A polymer compound made by polymerizing the compound described in claim 1.

[claim13]
13. The polymer compound according to claim 12, wherein the compound is bound to the polymer compound via a urethane binding in the polymer compound.

[claim14]
14. The polymer compound according to claim 12 further comprising, in a main chain of the polymer compound, a chemical structure included in the compound.

[claim15]
15. The polymer compound according to claim 12 further comprising a cross-linked site made of a chemical structure included in the compound.

[claim16]
16. The compound according to claim 2, wherein in the general Formula (1), the B1 and B2 have any structure of general Formulas (5-1) to (5-3):
wherein Z4 in general Formula (5-2) is the same as the Z2 and Z3.

[claim17]
17. The compound according to claim 2, wherein the D1, D2, and D3 have any of following structures:
wherein R1 to R7 each denote H, a linear, branched, or cyclic alkyl group with 1-20 carbons, an aryl group with 6-20 carbons, F, Cl, Br, I, CF3, CCl3, CN, or OCH3, and R1 to R7 may be the same or different.

[claim18]
18. The compound according to claim 3, wherein the D1, D2, and D3 have any of following structures:
wherein R1 to R7 each denote H, a linear, branched, or cyclic alkyl group with 1-20 carbons, an aryl group with 6-20 carbons, F, Cl, Br, I, CF3, CCl3, CN, or OCH3, and R1 to R7 may be the same or different.

[claim19]
19. The compound according to claim 2, wherein the E1, E2, and E3 are any of the Formulas (E-1) to (E-18):
wherein in the Formulas (E-12) and (E-13), X denotes amide or ester but may not be included, R1 in the Formulas (E-12) and (E-13) denotes H, a linear, branched, or cyclic alkyl group with 1-20 carbons, an aryl group with 6-20 carbons, F, Cl, Br, I, CF3, CCl3, CN, or OCH3, R in Formulas (E-1) to (E-18) denotes a linear, branched, or cyclic alkyl group with 1-20 carbons or an aryl group with 6-20 carbons, R in Formulas (E-1) to (E-11) may not be included, and each filled circle represents D1, D2, or D3.

[claim20]
20. The compound according to claim 3, wherein the E1, E2, and E3 are any of the Formulas (E-1) to (E-18):
wherein in the Formulas (E-12) and (E-13), X denotes amide or ester but may not be included, R1 in the Formulas (E-12) and (E-13) denotes H, a linear, branched, or cyclic alkyl group with 1-20 carbons, an aryl group with 6-20 carbons, F, Cl, Br, I, CF3, CCl3, CN, or OCH3, R in Formulas (E-1) to (E-18) denotes a linear, branched, or cyclic alkyl group with 1-20 carbons or an aryl group with 6-20 carbons, R in Formulas (E-1) to (E-11) may not be included, and each filled circle represents D1, D2, or D3.
  • 発明者/出願人(英語)
  • SAITO SHOHEI
  • YABU HIROSHI
  • ABE HIROYA
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
参考情報 (研究プロジェクト等) PRESTO Fully-controlled photons and their proactive usage for new era creation AREA
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