Compound for uses in optical and electrooptical devices

Patent metadata

Field	Value
Publication number	US-10144744-B2
Application number	US-201615193630-A
Country	US
Kind code	B2
Filing date	Jun 27, 2016
Priority date	Jun 27, 2016
Publication date	Dec 4, 2018
Grant date	Dec 4, 2018

Abstract

A compound having the following formula:

which can also be embedded into a conjugated oligomeric of polymeric backbone, is proposed for optical and electro optical applications.

First claim

The invention claimed is:

1. A compound having the following formula:

wherein
Q 1 , Q 2 are one or a mixture of π-conjugated aromatic cores;
R 1 and R 2 are selected, independently from each other, from the following group: H, halogen, methyl, Sn(R R,1 ) 3 , B(OH) 2 , OR R,2 , NR R,3 R R,4 , NO 2 , COOR R,5 , COR R,6 , SR R,7 , —CN, —CCR R,8 , —SO 3 H, —CH═C(CN) 2 , —CH═C(CN)(COOR R,9 ), —C(CN)═C(CN) 2 , substituted and unsubstituted ferrocene and derivatives thereof, substituted and unsubstituted pyridine and derivatives thereof, pentafluorophenol, and substituted and unsubstituted fullerene and derivatives thereof; with the residues R R,1 ,-R R,9 selected, independently from each other, from the group consisting of: methyl, ethyl, propyl, isopropyl, phenyl, benzyl, and primary, secondary, and tertiary amines;
V 1 and V 2 are selected, independently from each other, from the following group: CH 2 , S, O, NH, COO, CO, CONR V,1 , and NR V,2 CO, with the residues R V,1 and R V,2 selected, independently from each other, from the group consisting of H, methyl, ethyl, propyl, isopropyl, phenyl and benzyl;
X 1 and X 2 are selected, independently from each other, from the following group: N, and CH;
Z 1 and Z 2 are selected, independently from each other, from the following group: halogen, methyl, ethyl, propyl, isopropyl, phenyl, benzyl, SR Z,1 , OR Z,2 , COOR Z,3 , NR Z,4 R Z,5 NO 2 , —CN, and —SO 3 H, with the residues R Z,1 -R Z,5 selected, independently from each other, from the group consisting of H, methyl, ethyl, propyl, isopropyl, benzyl, primary amines, secondary amines, and tertiary amines;
L is a hydrocarbon chain with 5-15 carbon atoms in which up to 3 hydrocarbon moieties (—CH 2 —) can be replaced by one of the following moieties: O, NR L,1 , S, and/or in which there can be up to 3 double or triple bonds, in which pairs of the type —CH 2 —CH 2 — are replaced by —C≡C—, —R L,2 C═CR L,3 -, or —N═CR L,4 -, with the residues R L,1 -R L,4 selected, independently from each other, from the group consisting of H, methyl, ethyl, propyl, isopropyl and benzyl;
W is selected from the group consisting of: H, halogen, SR W,1 , methyl, ethyl, OR W,2 , and COOR W,3 , with the residues R W,1 -R W,3 selected, independently from each other, from the group consisting of H, methyl, ethyl, propyl, isopropyl, phenyl and benzyl;
S 1 —S 9 are selected, independently from each other, from the group consisting of: H, halogen, methyl, ethyl, phenyl, benzyl, OR S,1 , SR S,2 , COOR S,3 , C(═O)R S,4 , NR S,5 R S,6 , NO 2 , and SO 3 H,
with the proviso that pairs of S 1 -S 4 , S 5 and S 6 , pairs of S 7 -S 9 can be given by bridging conjugated structural elements selected from the group consisting of:
ortho (CH) 2 -benzene,
—(CR S,9 )(CR S,10 )(CR S,11 )—, —(CR S,12 )(CR S,13 )(CR S,14 )(CR S,15 )—, and —(CR S,16 )(CR S,17 )(CR S,18 )(CR S,19 )(CR S,20 )—, in which CR S,N moieties can be replaced by N, NH, O, and/or S,
with the residues R S,1 -R S,20 selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, phenyls and benzyl

P 1 , P 2 are one or a mixture of π-conjugated aromatic cores
l is selected to be an integer in the range of 0-10
m is selected to be an integer in the range of 1-10
n is selected to be an integer in the range of 0-10
x is selected to be an integer in the range of 1-10,000
with the proviso that 1+n is at least 1.

2. The compound according to claim 1 , wherein at least one of P 1 and P 2 is selected from the group consisting of at least one of: 2,1,3-benzothiadiazole, azole, diazole, triazole, tetrazole, thiophene, pyrrole, furane, selenophene, vinylene, selenazole, thiazole, thiadiazole, oxazole, oxadiazole, pyridine, diazine, triazine, tetrazine, selenazine, thiazine, azepine, diazepine, phenyl based cores, biphenyl based cores, arylamine derivatives, tetraphenylbenzidine, carbazole, pyrrole-based macrocycles, boron derivatives, difluoroboradiaza indacene, ethylenedioxythiophene, phosphorus derivatives, perylene derivatives, N,N dialkyl perylene dicarboximide, N,N dibenzyl perylene dicarboximide, naphthalene derivatives, N,N dialkyl naphthalene dicarboximide, N,N dibenzyl naphthalene dicarboximide, polycyclic aromatic hydrocarbons, thienothiophene and its derivatives, benzodithiophene and its derivatives, and tetrathiafulvalene and its derivatives.

3. The compound according to claim 1 , wherein at least one of P 1 and P 2 is selected to be thiophene or a bridged π-conjugated biphenyl.

4. The compound according to claim 1 , wherein one of Q 1 and Q 2 is given by one of the following structural moieties:

wherein R is R 1 or R 2 , respectively,
A 1 , A 2 , and A 3 are selected, independently from each other, from the following group: S, O, NH, NR A,1 , BH, BR A,1 , PR A,1 , PR A,1 R A,2 , Se, CH═CH, CH═N, CH═PR A,1 , CH═PR A,1 R A,2 , CH 2 , C═O, C═CH 2 , and C═CR A,1 R A,2 , with the residues R A,1 and R A,2 selected, independently from each other, from the group consisting of H, methyl, ethyl, propyl and benzyl;
S 11 and S 13 are selected, independently from each other, from the group consisting of: H, halogen, methyl, ethyl, phenyl, benzyl, OR S,21 , SR S,22 , COOR S,23 , C(═O)R S,24 , NR S,25 R S,26 , NO 2 , and SO 3 H, with the residues R S,21 -R S,26 selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, phenyl and benzyl.

5. The compound according to claim 4 , wherein S11 and S13 are each selected to be H.

6. The compound according to claim 1 , wherein Q 1 -Q 2 are each selected to be thiophene.

7. The compound according to claim 1 , wherein X 1 and X 2 are each selected to be N.

8. The compound according to claim 1 , wherein V 1 and V 2 are each selected to be O.

9. The compound according to claim 1 , wherein Z 1 and Z 2 are each selected to be methyl.

10. The compound according to claim 1 , wherein W is selected from the group consisting of methyl and methoxy.

11. The compound according to claim 1 , wherein L is selected to be a hydrocarbon chain with 8-12 carbon atoms, in which up to 2 hydrocarbon moieties can be replaced by one of the following moieties: O, NH, S, and in which there can be up to 2 carbon-carbon double or triple bonds.

12. The compound according to claim 1 , wherein L is selected to be a (CH 2 ) chain with 8-12 carbon atoms, and two of the (CH 2 ) moieties are replaced by (CH) to form a double bond.

13. The compound according to claim 1 , wherein L is selected to be a (CH 2 ) chain with 10 carbon atoms, and two of the (CH 2 ) moieties are replaced by (CH) to form a double bond at the position of the fifth carbon atom of the chain of L.

14. The compound according to claim 1 , wherein S 1 -S 9 are each selected to be H.

15. The compound according to claim 1 , wherein x is selected to be an integer in the range of 10-1000.

16. The compound according to claim 1 , wherein at least one of P1 and P2 is selected from the group consisting of at least one of: 2,1,3-benzothiadiazole, azole, imidazole and pyrazole, triazole, tetrazole, thiophene, pyrrole, furane, selenophene, vinylene, selenazole, thiazole, thiadiazole, oxazole, oxadiazole, pyridine, pyrimidine, triazine, tetrazine, selenazine, thiazine, azepine, diazepine, phenyl based cores, biphe

Assignees

• Ecole Polytechnique Fed Lausanne Epfl

Inventors

• Sforazzini Giuseppe

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C08G2261/57

  photorefractive, e.g. change of refractive index · CPC title

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• C08G2261/92

  TFT applications · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title