Second-order nonlinear optical compound and nonlinear optical element comprising the same

Patent metadata

Field	Value
Publication number	US-9977150-B2
Application number	US-201615208976-A
Country	US
Kind code	B2
Filing date	Jul 13, 2016
Priority date	Aug 24, 2009
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

Problem to Be Solved: to provide a chromophore having a far superior nonlinear optical activity to conventional chromophores and to provide a nonlinear optical element comprising said chromophore.
Solution: a chromophore comprising a donor structure D, a π-conjugated bridge structure B, and an acceptor structure A, the donor structure D comprising an aryl group substituted with a substituted oxy group; and a nonlinear optical element comprising said chromophore.

First claim

The invention claimed is:

1. A chromophore represented by formula D-B-A, wherein B is represented by the formula B-I:

wherein
π 1 and π 2 independently represent the same or different carbon-carbon conjugated π-bonds, and π 1 and π 2 each may have the same or different substituents; and
R B 1 and R B 2 independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an alkenyl group, a cycloalkyl group, a cycloalkenyl group, a haloalkyl group, an aralkyl group, an aryloxy group, or an aralkyloxy group, and R B 1 and R B 2 each may have the same or different substituents and

D is represented by the formula D-1-1:

wherein
R D 1 represents an alkoxy group, an aryloxy group, an aralkyloxy group, a silyloxy group, an alkenyloxy group, an alkenylcarbonyloxy group, an alkynyloxy group, or a hydroxy group, and R D 1 may have a substituent selected from the group consisting of an alkyl group, a haloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a silyl group, an alkenyl group, an alkynyl group, an acyl group, and an alkenylcarbonyl group;
R D 2 and R D 3 independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, a silyloxy group, an alkenyloxy group, an alkenylcarbonyloxy group, an alkynyloxy group, or a hydroxy group, and R D 2 and R D 3 each may have the same or different substituents selected from the group consisting of an alkyl group, a haloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a silyl group, an alkenyl group, an alkynyl group, an acyl group, and an alkenylcarbonyl group
when R D 2 and R D 3 are each attached to adjacent carbon atoms of the aryl of D,
R D 2 and R D 3 may form, together with the two adjacent carbon atoms, a ring optionally having a substituent selected from the group consisting of an alkyl group, a haloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a silyl group, an alkenyl group, an alkynyl group, an acyl group, and an alkenylcarbonyl group; and
R D 4 and R D 5 independently represent a hydrogen atom, an alkyl group, a haloalkyl group, a hydroxyalkyl group, an acyloxyalkyl group, a silyloxyalkyl group, an aminoalkyl group, or an aryl group, or
R D 4 and R D 5 form, together with the nitrogen atom to which they are attached, a heterocyclic ring; or
(a) R D 2 and —NR D 4 R D 5 and (b) R D 3 and —NR D 4 R D 5 independently form, together with the carbon atoms to which they are attached, a heterocyclic ring,

A is represented by the formula

wherein
Y represents —CR A 1 R A 2 —, —O—, —S—, —SO—, —SiR A 1 R A 2 —, —NR— wherein R represents a hydrogen atom or an alkyl group, or —C(═CH 2 )—; and
R A 1 and R A 2 independently represent a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, a cycloalkenyl group, an alkoxy group, a haloalkyl group, or an aryl group, or
R A 1 and R A 2 form, together with the carbon atom to which they are attached, a structure that is represented by the following formula:

2. The chromophore according to claim 1 , wherein the chromophore is represented by the formula I-1-1:

wherein
π 1 and π 2 independently represent the same or different carbon-carbon conjugated π-bonds, and π 1 and π 2 each may have the same or different substituents;
R D 1 represents an alkoxy group, an aryloxy group, an aralkyloxy group, a silyloxy group, an alkenyloxy group, an alkenylcarbonyloxy group, an alkynyloxy group, or a hydroxy group, and R D 1 may have a substituent as defined in claim 1 ;
R D 2 and R D 3 independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, a silyloxy group, an alkenyloxy group, an alkenylcarbonyloxy group, an alkynyloxy group, or a hydroxy group, and R D 2 and R D 3 each may have the same or different substituents as defined in claim 1
when R D 2 and R D 3 are each attached to adjacent carbon atoms of the aryl of D,
R D 2 and R D 3 may form, together with the two adjacent carbon atoms, a ring optionally having a substituent as defined in claim 1 ;
R D 4 and R D 5 independently represent a hydrogen atom, an alkyl group, a haloalkyl group, a hydroxyalkyl group, an acyloxyalkyl group, a silyloxyalkyl group, an aminoalkyl group, or an aryl group, or
R D 4 and R D 5 form, together with the nitrogen atom to which they are attached, a heterocyclic ring containing the nitrogen atom as a hetero atom; or
(a) R D 2 and —NR D 4 R D 5 and (b) R D 3 and —NR D 4 R D 5 independently form, together with the carbon atoms to which they are attached, a heterocyclic ring containing the nitrogen atom as a hetero atom;
R B 1 and R B 2 independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, an aryloxy group, or an aralkyloxy group, and R B 1 and R B 2 each may have the same or different substituents; and
R A 1 and R A 2 independently represent a hydrogen atom, an alkyl group, a haloalkyl group, or an aryl group.

3. A chromophore represented by formula D-B-A, wherein B is represented by the formula B-III:

wherein
m and m′ independently represent an integer of 0 to 3; and
R B 1 , R B 2 , and R B 3 independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an alkenyl group, a cycloalkyl group, a cycloalkenyl group, a haloalkyl group, an aralkyl group, an aryloxy group, or an aralkyloxy group, and R B 1 , R B 2 , and R B 3 each may have the same or different substituents and

D is represented by the formula D-1-1:

wherein
R D 1 represents an alkoxy group, an aryloxy group, an aralkyloxy group, a silyloxy group, an alkenyloxy group, an alkenylcarbonyloxy group, an alkynyloxy group, or a hydroxy group, and R D 1 may have a substituent selected from the group consisting of an alkyl group, a haloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a silyl group, an alkenyl group, an alkynyl group, an acyl group, and an alkenylcarbonyl group;
R D 2 and R D 3 independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, a silyloxy group, an alkenyloxy group, an alkenylcarbonyloxy group, an alkynyloxy group, or a hydroxy group, and R D 2 and R D 3 each may have the same or different substituents selected from the group consisting of an alkyl group, a haloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a silyl group, an alkenyl group, an alkynyl group, an acyl group, and an alkenylcarbonyl group
when R D 2 and R D 3 are each attached to adjacent carbon atoms of the aryl of D,
R D 2 and R D 3 may form, together with the two adjacent carbon atoms, a ring optionally having a substituent selected from the group consisting of an alkyl group, a haloalkyl group, an aryl group, a heteroaryl group, an aralkyl group, a silyl group, an alkenyl group, an alkynyl gr

Assignees

• Nat Inst Inf & Comm Tech
• Sumitomo Electric Industries
• Univ Kyushu Nat Univ Corp

Inventors

• Otomo Akira
• Aoki Isao
• Miki Hideki
• Tazawa Hidehisa
• Yokoyama Shiyoshi

Classifications

• G02F1/3615

  containing polymers · CPC title

• G02F1/3611

  containing Nitrogen · CPC title

• C07D307/30

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C09B69/107

  containing an azomethine dye · CPC title

• G02F1/3612

  Heterocycles having N as heteroatom · CPC title