JP-7855774-B2 - Fluorene derivatives, methods for producing the same, and their uses

Inventors

• 小西 孝治
• 安田 理恵
• 宮内 信輔
• 元廣 伊吹
• 光實 真哉人
• 安田 祐一郎

Assignees

• 大阪ガスケミカル株式会社

Dates

Publication Date

20260508

Application Date

20250829

Priority Date

20191226

Claims (3)

1. The following formula (2) (In the formula, Z1a and Z1b each independently represent a naphthalene ring or a biphenyl ring.) R1a and R1b each independently represent a linear or branched C1-4 alkyl group, and k1 and k2 each independently represent an integer from 0 to 3. m1 and m2 indicate 1. R2a and R2b each independently represent a linear or branched C1-4 alkyl group, and n1 and n2 each independently represent an integer from 0 to 3. A1a and A1b each independently represent linear or branched C1-6 alkylene groups. A2a and A2b each independently represent a linear or branched C2-4 alkylene group, and p1 and p2 each independently represent an integer from 0 to 3. A compound represented by the formula.
2. In formula (2) above, Z1a and Z1b are naphthalene rings, A1a and A1b are linear or branched C1-4 alkylene groups. The compound according to claim 1, wherein p1 and p2 are 0.
3. The following formula (5A) (In the formula, R 4a and R 4b each independently represent a hydrogen atom or an alkyl group, A3a and A3b each independently represent alkylene groups with one less carbon atom, corresponding to A1a and A1b in formula (2). Z1a and Z1b , R1a and R1b , k1 and k2, m1 and m2, R2a and R2b , and n1 and n2 are the same as in formula (2) above. A method for producing the compound according to claim 1 or 2, comprising a reduction step of reducing the compound represented by .

Description

This disclosure relates to novel di(meth)acrylate compounds having a fluorene skeleton, as well as methods for producing the same and their applications. Compounds containing a 9,9-bisarylfluorene skeleton exhibit excellent optical properties, such as a high refractive index, and are therefore effectively used in various optical components as optical plastics (or optical resin materials). Many compounds containing such a 9,9-bisarylfluorene skeleton are known, including (meth)acrylate compounds. Patent documents 1 and 2 describe (meth)acrylate compounds containing a 9,9-bis-condensed polycyclic arylfluorene skeleton and curable compositions containing these (meth)acrylate compounds, particularly those exhibiting a high refractive index. Furthermore, Patent Document 3 describes the synthesis of 9,9-bis(3-acryloyloxypropyl)fluorene. Japanese Patent Publication No. 2009-173648Japanese Patent Publication No. 2018-059059U.S. Patent Application Publication No. 2003/0049173 [Di(meth)acrylate compounds] The novel di(meth)acrylate compounds of this disclosure are represented by the following formula (1). (In the formula, Z1a and Z1b each independently represent an arene ring.) R1a and R1b each independently represent substituents, and k1 and k2 each independently represent integers greater than or equal to 0. m1 and m2 each independently represent integers from 0 to 4, and at least one of m1 and m2 is 1 or greater. R2a and R2b each independently represent substituents, and n1 and n2 each independently represent integers from 0 to 4. m1 + n1 and m2 + n2 are each less than or equal to 4. A1a and A1b each independently represent linear or branched alkylene groups. A2a and A2b each independently represent a linear or branched alkylene group, and p1 and p2 each independently represent an integer of 0 or more. R3a and R3b each independently represent a hydrogen atom or a methyl group. In formula (1) above, the arene rings (aromatic hydrocarbon rings) represented by Z1a and Z1b include, for example, monocyclic arene rings such as benzene rings, and polycyclic arene rings. Examples of polycyclic arene rings include condensed polycyclic arene rings (condensed polycyclic aromatic hydrocarbon rings) and ring-aggregated arene rings (ring-aggregated polycyclic aromatic hydrocarbon rings). Examples of fused polycyclic arene rings include fused bicyclic arene rings, fused tricyclic arene rings, and other fused bicyclic to tetracyclic arene rings. Examples of fused bicyclic arene rings include fused bicyclic C10-16 arene rings such as naphthalene rings and indene rings. Examples of fused tricyclic arene rings include fused tricyclic C14-20 arene rings such as anthracene rings and phenanthrene rings. A preferred fused polycyclic arene ring is a fused polycyclic C10-14 arene ring, such as a naphthalene ring. Examples of ring-assembled arene rings include bialene rings such as biphenyl rings, phenylnaphthalene rings, and binaphthyl rings; and telarene rings such as terphenyl rings. Preferred ring-assembled arene rings are C12-18 bialene rings such as biphenyl rings. In this specification and within the claims, "ring-assembled arene ring" refers to an arene ring in which two or more ring systems (arene ring systems) are directly connected by single or double bonds, and the number of bonds directly connecting the rings is one less than the number of ring systems. For example, as mentioned above, bialene rings such as biphenyl rings, phenylnaphthalene rings, and binaphthyl rings are classified as ring-assembled arene rings even if they have a fused polycyclic arene ring skeleton such as a naphthalene ring skeleton. Therefore, "ring-assembled arene rings" are clearly distinguished from "fused polycyclic arene rings" such as naphthalene rings (aring-assembled arene rings). Preferred rings Z1a and Z1b include C6-14 arene rings, more preferably C6-12 arene rings such as benzene rings, naphthalene rings, and biphenyl rings, and even more preferably C6-10 arene rings such as benzene rings and naphthalene rings, and especially naphthalene rings. The types of rings Z1a and Z1b may be different from each other, but it is preferable that they be the same. Also, if m1 is 2 or more, the types of the two or more rings Z1a may be the same or different from each other. The same applies to m2 and Z1b . Furthermore, rings Z1a and Z1b may be substituted at any of the positions 1-4 and 5-8 of the fluorene skeleton, respectively, but positions 2, 3 and/or 7 are preferred. When m1 and m2 are 1, preferred substitution positions (or bonding positions) are positions that are symmetrical on the plane of the paper in formula (1), such as positions 1,8, 2,7, 3,6, and 4,5, with positions 2,7 being particularly preferred. Examples of substituents represented by R1a and R1b (non-reactive substituents or non-polymerizable substituents) include halogen atoms, hydrocarbon groups (or groups [ -Rh ]), groups [ -ORh ] (wherein Rh represents the hydrocarbon group), groups [