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CN-121986129-A - Compound, method for producing same, curable resin composition, and cured product thereof

CN121986129ACN 121986129 ACN121986129 ACN 121986129ACN-121986129-A

Abstract

The invention provides a compound with excellent low dielectric property, a hardening resin composition and a hardening product thereof. The compound of the present invention is represented by the following formula (1). In the above formula (1), R 1 present in plural are each independently a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms. R 2 present in plural numbers independently represents a hydrocarbon group represented by the following formula (a). X is a structure represented by the following formulas (c) to (f). L present in plural numbers independently represents an integer of 1 to 4. M present in plural numbers independently represents an integer of 0 to 3, and the average value m ave of m is 0<m ave ≤3. n is a repetition number of times, n ave is 0.05- ave -20; In the above formula (a), the bonding position to the fluorene structure of formula (1) is represented. R 3 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, and k represents an integer of 1 to 5; In the above formulas (c) to (f), the bonding position to the fluorene structure of formula (1) is represented. R 4 present in plural independently represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms. P present in plural are each independently an integer of 1 to 4, and q present in plural are each independently an integer of 1 to 3.

Inventors

  • Toshima Takashiroyuki
  • HARAMOTO MASANORI

Assignees

  • 日本化药株式会社

Dates

Publication Date
20260505
Application Date
20240909
Priority Date
20230921

Claims (7)

  1. 1. A compound represented by the following formula (1); In the above formula (1), R 1 existing in a plurality of groups independently represent a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, R 2 existing in a plurality of groups independently represent a hydrocarbon group having the following formula (a), X is a structure having the following formulas (c) to (f), l existing in a plurality of groups independently represent an integer having 1 to 4, m existing in a plurality of groups independently represent an integer having 0 to 3, m ave is 0<m ave ≤3, n is a repetition number, and nave is 0.05≤n ave ≤20; in the above formula (a), x represents a bonding position to the fluorene structure of formula (1), R 3 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, and k represents an integer of 1 to 5; In the above formulae (c) to (f), each of R 4 existing in plural is independently a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, each of p existing in plural is independently an integer of 1 to 4, and each of q existing in plural is independently an integer of 1 to 3.
  2. 2. A compound obtained by reacting a compound represented by the following formula (A) with a compound represented by the following formula (B); In the above formula (A), R 2 existing in plural are each independently a hydrocarbon group represented by the following formula (a), X is a structure represented by the following formulas (c) to (f), m existing in plural are each independently an integer of 0 to 3, the average value m ave of m is 0<m ave ≤3, n is a repetition number, and the average value n ave of n is 0.05≤n ave ≤20; In the above formula (a), x represents a bonding position to the fluorene structure of formula (a), R 3 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, and k represents an integer of 1 to 5; In the above formulas (c) to (f), the bonding position to the fluorene structure of formula (a) is represented, R 4 existing in plural is independently represented by a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, p existing in plural is independently represented by an integer of 1 to 4, and q existing in plural is independently represented by an integer of 1 to 3; In the above formula (B), R 1 represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, k represents an integer of 1 to 4, and Y represents a halogen atom.
  3. 3. A curable resin composition comprising the compound according to claim 1 or 2.
  4. 4. A cured product obtained by curing the compound according to claim 1 or 2.
  5. 5. A cured product obtained by curing the curable resin composition according to claim 3.
  6. 6. A method for producing a compound, wherein a compound represented by the following formula (A) and a compound represented by the following formula (B) are reacted in an aprotic polar solvent in the presence of a basic catalyst to obtain a compound; In the above formula (A), R 2 existing in plural are each independently a hydrocarbon group represented by the following formula (a), X is a structure represented by the following formulas (c) to (f), m existing in plural are each independently an integer of 0 to 3, the average value m ave of m is 0<m ave ≤3, n is a repetition number, and the average value n ave of n is 0.05≤n ave ≤20; In the above formula (a), x represents a bonding position to the fluorene structure of formula (a), R 3 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, and k represents an integer of 1 to 5; In the above formulas (c) to (f), the bonding position to the fluorene structure of formula (1), R 4 existing in plural numbers independently represent a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, p existing in plural numbers independently represent an integer of 1 to 4, and q existing in plural numbers independently represent an integer of 1 to 3; In the above formula (B), R 1 represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, k represents an integer of 1 to 4, and Y represents a halogen atom.
  7. 7. A compound represented by the following formula (a); In the above formula (A), R 2 existing in plural are each independently a hydrocarbon group represented by the following formula (a), X is a structure represented by the following formulas (c) to (f), m existing in plural are each independently an integer of 0 to 3, the average value m ave of m is 0<m ave ≤3, n is a repetition number, and the average value n ave of n is 0.05≤n ave ≤20; In the above formula (a), x represents a bonding position to the fluorene structure of formula (a), R 3 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, and k represents an integer of 1 to 5; In the above formulae (c) to (f), each of R 4 existing in plural is independently a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, each of p existing in plural is independently an integer of 1 to 4, and each of q existing in plural is independently an integer of 1 to 3.

Description

Compound, method for producing same, curable resin composition, and cured product thereof Technical Field The present invention relates to a compound having a specific structure, a curable resin composition, and a cured product thereof, which are suitable for use in electrical/electronic parts such as semiconductor sealing materials, printed wiring boards, laminate boards, lightweight high-strength materials such as carbon fiber reinforced plastics and glass fiber reinforced plastics, and 3D printing applications. Background In recent years, a laminate board on which an electrical/electronic component is mounted is demanded to have wide characteristics and to be highly advanced due to expansion of its application field. Although a semiconductor chip (chip) is mainly mounted on a metal lead frame, a semiconductor chip (chip) having high processing capacity such as a central processing unit (hereinafter, referred to as a CPU) is often mounted on a laminate board made of a polymer material. The fifth generation communication system "5G" which is now under accelerated development is predicted to be more capacitative and to communicate at a higher speed. Although the frequency used in 5G is increasing, it is important to reduce the transmission loss and further lower the dielectric characteristics of the substrate material in order to realize high-speed communication using high frequencies. The transmission loss generated on the printed board is derived from the conductor loss and the dielectric loss. As described in non-patent document 1, since the dielectric loss α D is proportional to the square root of the specific permittivity epsilon r and the dielectric tangent tan δ of the dielectric material, it is possible to effectively improve the dielectric tangent tan δ having a high contribution to the specific permittivity epsilon r or more by reducing the transmission loss. The low dielectric material is a thermoplastic material typified by PTFE (polytetrafluoroethylene) or LCP (liquid crystal polymer), but is inferior to a thermosetting resin in moldability. Accordingly, development of a thermosetting resin excellent in low dielectric characteristics is desired. With such a background, a polymer material having excellent low dielectric characteristics has been studied. For example, patent document 1 proposes a thermosetting resin composition containing an imide compound having a maleimide group and a phenol aralkyl resin having an aliphatic unsaturated bond. However, on the other hand, phenolic hydroxyl groups which do not participate in the reaction remain during the hardening reaction, and therefore it is difficult to obtain sufficient electrical characteristics. Further, patent document 2 discloses an allyl ether-modified biphenyl aralkyl novolak resin to which a phenolic hydroxyl group is added to allyl group. However, the allyl ether-modified biphenyl aralkyl novolak resin exhibits Claisen (Claisen) translocation at 190 ℃ and phenolic hydroxyl groups which do not contribute to the hardening reaction at 200 ℃ which is a molding temperature of a general substrate, and thus, electrical characteristics are not satisfactory. [ Prior Art literature ] [ Non-patent literature ] Non-patent document 1, "cause of signal loss in high-speed signal transmission on a printed circuit board", the 29 th electronic packaging society, the spring lecture university, session ID 16P1-17, 2015. [ Patent literature ] Patent document 1 Japanese patent laid-open No. 04-359911 Patent document 2 International publication No. 2016/002704. Disclosure of Invention [ Problem to be solved by the invention ] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a compound having excellent low dielectric characteristics, a method for producing the compound, a curable resin composition, and a cured product thereof. [ Means for solving the problems ] That is, the present invention relates to the following [1] to [7]. In the present invention, "(numerical value 1) to" (numerical value 2) "means that the upper and lower limit values are included. [1] A compound represented by the following formula (1). In the above formula (1), R 1 existing in plural are each independently a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, R 2 existing in plural are each independently a hydrocarbon group represented by the following formula (a), X is a structure represented by any one of the following formulas (c) to (f), l existing in plural are each independently an integer of 1 to 4, m existing in plural are each independently an integer of 0 to 3, the average value m ave of m is 0<m ave≤3, n is a repetition number, and the average value n ave of n is 0.05≤n ave≤20; in the above formula (a), x represents a bonding position to the fluorene structure of formula (1), R 3 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, and k represents an integer of 1