Nonlinear optical element, electro-optic element, and compound
The present invention relates to a nonlinear optical material or an electro-optic material and which is suited for manufacturing nonlinear optical elements or electro-optic elements. The nonlinear optical or electro-optic material is represented by Formula (I): wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , E 1 , E 2 , A 1 , B 1 , B 2 , m, n, D 1 , D 2 , R 1 , and L 1 are defined in the specification respectively.
1 . A nonlinear optical element comprising a layer that contains the compound represented by Formula (I):
wherein Ar 1 , Ar 2 , Ar 3 , and Ar 4 each independently represent a five- or six-membered aromatic ring, a five- or six-membered heterocyclic aromatic ring, or a condensed ring thereof, and wherein the rings may have a substituent or substituents; E 1 represents a hydrogen atom or an electron-attracting group; E 2 represents an electron-attracting group; A 1 represents a hydrogen atom or an electron-attracting group; B 1 and B 2 each independently represent a single bond, —CH═CH—, —C≡C—, —N═N—, *—COO—, or *—COS—, wherein a bond marked by * is on the left side in Formula (I); m and n each independently represent 1 or 2; D 1 represents an oxygen atom, a sulfur atom or —NR 2 —; R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms and R 1 and R 2 may be coupled to each other to form a ring; L 1 represents a bivalent linking group; D 2 represents an oxygen atom, a sulfur atom or —NR 3 —; R 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; L 1 and R 3 may be coupled to each other to form a ring; and R 1 , R 2 , R 3 , and L 1 may each independently have a substituent or substituents.
2 . The nonlinear optical element of claim 1 , wherein the electron-attracting group represented by A 1 is —CN, —NO 2 , —C═C(CN) 2 , —C═C(CN)COO—R 4 , —COO—R 4 , or —SO 2 —R 4 , wherein R 4 represents an alkyl group having 1 to 20 carbon atoms, and the alkyl group may have a hydroxyl group, an amino group, an ester group, an amide group, an ether group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom.
3 . The nonlinear optical element of claim 1 , wherein B 1 and B 2 are each independently a single bond, —C≡C— or —N═N—.
4 . The nonlinear optical element of claim 2 , wherein B 1 and B 2 are each independently a single bond, —C≡C— or —N═N—.
5 . The nonlinear optical element of claim 1 , wherein E 2 is an electron-attracting group having a sp value of 0.2 to 1.2.
6 . The nonlinear optical element of claim 1 , wherein E 1 is hydrogen.
7 . The nonlinear optical element of claim 2 , wherein E 1 is hydrogen.
8 . The nonlinear optical element of claim 3 , wherein E 1 is hydrogen.
9 . The nonlinear optical element of claim 5 , wherein E 1 is hydrogen.
10 . The nonlinear optical element of claim 1 , wherein Ar 1 , Ar 2 , Ar 3 and Ar 4 each independently represent a five- or six-membered aromatic ring, a five- or six-membered heterocyclic aromatic ring, or a condensed ring thereof, and wherein the rings are unsubstituted.
11 . An electro-optic element comprising a layer that contains the compound represented by Formula (I):
Wherein Ar 1 , Ar 2 , Ar 3 , and Ar 4 each independently represent a five- or six-membered aromatic ring, a five- or six-membered heterocyclic aromatic ring, or a condensed ring thereof, wherein the rings may have a substituent or substituents; E 1 represents a hydrogen atom or an electron-atttacting group; E 2 represents an electron-attracting group; A 1 represents a hydrogen atom or an electron-attracting group; B 1 and B 2 each independently represent a single bond, —CH═CH—, —C≡C—, —N═N—, *—COO—, or *—COS—, wherein a bond marked by * is on the left side in Formula (I); m and n each independently represent 1 or 2; D 1 represents an oxygen atom, a sulfur atom or —NR 2 —; R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms and R 1 and R 2 may be coupled to each other to form a ring; L 1 represents a bivalent linking group; D 2 represents an oxygen atom, a sulfur atom or —NR 3 —; R 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; L 1 and R 3 may be coupled to each other to form a ring; and R 1 , R 2 , R 3 , and L 1 may each independently have a substituent or substituents.
12 . The electro-optic element of claim 11 , wherein the electron-attracting group represented by A 1 is —CN, —NO 2 , —C═C(CN) 2 , —C═C(CN)COO—R 4 , —COO—R 4 , or —SO 2 —R 4 , wherein R 4 represents an alkyl group having 1 to 20 carbon atoms, and the alkyl group may have a hydroxyl group, an amino group, an ester group, an amide group, an ether group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom.
13 . The electro-optic element of claim 11 , wherein B 1 and B 2 are each independently a single bond, —C≡C— or —N═N—.
14 . The electro-optic element of claim 12 , wherein B 1 is and B 2 are each independently a single bond, —C≡C— or —N═N—.
15 . The electro-optic element of claim 11 , wherein E 2 is an electron-attracting group having a sp value of 0.2 to 1.2.
16 . The electro-optic element of claim 11 , wherein E 1 is hydrogen.
17 . The electro-optic element of claim 12 , wherein E 1 is hydrogen.
18 . The electro-optic element of claim 13 , wherein E 1 is hydrogen.
19 . The electro-optic element of claim 15 , wherein E 1 is hydrogen.
20 . The electro-optic element of claim 11 , wherein Ar 1 , Ar 2 , Ar 3 and Ar 4 each independently represent a five- or six-membered aromatic ring, a five- or six-membered heterocyclic aromatic ring, or a condensed ring thereof, and wherein the rings are unsubstituted.
21 . A compound represented by Formula (II):
wherein Ar 1 , Ar 2 , Ar 3 , and Ar 4 each independently represent a five- or six-membered aromatic ring, a five- or six-membered heterocyclic aromatic ring, or a condensed ring thereof, wherein the rings may have a substituent or substituents; E 2 represents an electron-attracting group having a σp value of 0.2 to 1.2; A 1 represents a hydrogen atom or an electron-attracting group having a σp value of 0.2 to 1.2; B 1 and B 2 each independently represent a single bond, —CH═CH—, —C≡C—, —N═N—, *—COO—, or *—COS—, wherein a bond marked by * is on the left side in Formula (II); m and n each independently represent 1 or 2; D 1 represents an oxygen atom, a sulfur atom or —NR 2 —; R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms and R 1 and R 2 may be coupled to each other to form a ring; L 1 represents an alkylene group having 1 to 20 carbon atoms; D 2 represents an oxygen atom, a sulfur atom or —NR 3 —; R 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; L 1 and R 3 may be coupled to each other to form a ring; and R 1 , R 2 , R 3 , and L 1 may each independently have a substituent or substituents.
22 . The compound of claim 21 , wherein the compound represented by Formula (II) is also represented by the following Formula (III):
wherein A 1 has the same meaning as defined in Formula (II); the four benzene rings may have a substituent or substituents, wherein the substituents on the benzene rings may be the same or different; and B 1 , B 2 , m, n, R 1 , R 2 , L 1 , D 1 , and D 2 each have the same meaning as defined in Formula (II).
23 . The compound of claim 21 , wherein the electron-attracting group represented by A 1 is —CN, —NO 2 , —C═C(CN) 2 , —C═C(CN)COO—R 4 , —COO—R 4 , or —SO 2 —R 4 , wherein R 4 represents an alkyl group having 1 to 20 carbon atoms, and the alkyl group may have a hydroxyl group, an amino group, an ester group, an amide group, an ether group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom.
24 . The compound of claim 22 , wherein the electron-attracting group represented by A 1 is —CN, —NO 2 , —C═C(CN) 2 , —C═C(CN)COO—R 4 , —COO—R 4 , or —SO 2 —R 4 , wherein R 4 represents an alkyl group having 1 to 20 carbon atoms, and the alkyl group may have a hydroxyl group, an amino group, an ester group, an amide group, an ether group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom.
25 . The compound of claim 21 , wherein B 1 and B 2 are each independently a single bond, —C≡C— or —N═N—.
26 . The compound of claim 22 , wherein B 1 and B 2 are each independently a single bond, —C≡C— or —N═N—.
27 . The compound of claim 21 , wherein Ar 1 , Ar 2 , Ar 3 and Ar 4 each independently represent a five- or six-membered aromatic ring, a five- or six-membered heterocyclic aromatic ring, or a condensed ring thereof, and wherein the rings are unsubstituted.