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Polyester having π-conjugated group in side chain and charge transporting material using the same

Foreign code F110005458
File No. K05306US
Posted date Sep 6, 2011
Country United States of America
Application number 51365903
Gazette No. 20050228163
Gazette No. 7235620
Date of filing May 7, 2003
Gazette Date Oct 13, 2005
Gazette Date Jun 26, 2007
International application number JP2003005727
International publication number WO2003095519
Date of international filing May 7, 2003
Date of international publication Nov 20, 2003
Priority data
  • P2002-132598 (May 8, 2002) JP
  • 2003WO-JP05727 (May 7, 2003) WO
Title Polyester having π-conjugated group in side chain and charge transporting material using the same
Abstract (US7235620)
A polyester expressed by the following structural formula 1, and a charge transport material obtained by adding an electron acceptor compound or an electron donor compound to this polyester.
In the aforesaid structural formula, Ar is an aromatic group and this aromatic group may contain a heterocyclic ring.
R1 is a carbon atom or absent (direct bond), R2-R9 are hydrogen atoms, electron donor groups or electron attracting groups, R20, R21 are hydrogen atoms or organic groups, X is a hetero atom, hetero atom-containing group, organic group or absent (direct bond), and m is an integer equal to 2 or more.
Scope of claims [claim1]
1. A polyester having pi -conjugated electrons of the following structural formula 1:
wherein, R1 is a carbon atom or R1 is absent thereby providing a direct bond, in which case R20 and R21 are not present,R2-R9 are independently hydrogen atoms, electron donor groups or electron attracting groups,m is an integer equal to 2 or more, Ar is an aromatic group including an aromatic group having a heterocyclic ring, R20, R21 are, independently, hydrogen atoms, alkyl groups, aromatic groups, -- CN or ester groups, andX is -- O -- ;
-- NR -- where R is a hydrogen atom, alkyl group or aromatic group;
-- S -- ;
-- CH2 -- ;
or absent resulting in a direct bond.
[claim2]
2. The polyester according to claim 1, wherein the molecular weight of said polyester is from 400 to one million in terms of number average molecular weight.
[claim3]
3. The polyester according to claim 2, wherein the distance between the polycyclic groups in adjacent units in said polyester is 4-20 angstroms.
[claim4]
4. The polyester according to claim 1, wherein Tg of said polyester is 30-300 deg. C.
[claim5]
5. A composition obtained by adding an electron acceptor compound or an electron donor compound to the polyester according to claim 1.
[claim6]
6. The composition according to claim 5, wherein said composition forms a charge transfer complex.
[claim7]
7. A charge transport material formed using the composition according to claim 6.
[claim8]
8. The polyester of claim 1, wherein each Ar is phenyl and X is -- CH2 -- .
[claim9]
9. The polyester of claim 1, wherein R1 is absent thereby providing a direct bond, in which case R20 and R21 are not present.
[claim10]
10. The polyester of claim 1, wherein R2-R9 are independently hydrogen atoms, electron donor groups selected from F, Cl, Br, I, -- OH, -- OR, -- O(C.dbd.O)R, -- NR10R11, -- SR, -- SH or an alkyl group, or electron attracting groups selected from -- CN, -- (C.dbd.O)R, -- SO2, -- NO2, phenyl, -- COOH or -- COOR, where R, R10, and R11 are each independently a hydrogen atom, alkyl group or aromatic group.
[claim11]
11. The polyester of claim 10, wherein R2-R9 are selected from one of the following combinations: all H,R3 and R8 are -- NR10R11, and R2, R4-R7, and R9 are H,R3 R8 are -- H2, and R2, R4-R7, and R9 are H,R3 and R8 are -- N(phenyl)2, and R2, R4-R7, and R9 are H,R3, R6 and R8 are -- NO2, and R2, R4, R5, R7, and R9 are H,R3 and R8 are -- NO2, and R2, R4-R7, and R9 are H,R3, R6 and R8 are -- CN, and R2, R4, R5, R7, and R9 are H, orR3 and R8 are -- CN, and R2, R4-R7, and R9 are H.
[claim12]
12. The composition of claim 5, wherein the composition comprises an electron acceptor compound selected from halogen compounds, Lewis acid compounds, proton acid compounds, transition metal halides or (9-fluorenylidene)acetonitrile, (9-fluorenylidene)malononitrile, (2,4,7-trinitro-9-fluorenylidene)acetonitrile, (2,4,7-trinitro-9-fluorenylidene)malononitrile, o-dinitrobenzene, m-dinitrobenzene, p-dinitrobenzene, 2,4,6-trinitrobenzene, 2,4,6-trinitrotoluene, tetracyanoquinodimethane (TCNQ), tetracyanoethylene (TCNE) or 2,3-dichloro-5 ,6-dicyano-p-benzoquinone (DDQ).
[claim13]
13. The composition of claim 5, wherein the composition comprises an electron donor compound selected from hexamethylbenzene, an alkali metal compound, an ammonium ion compound or a lanthanoid compound.
[claim14]
14. The polyester of claim 1, wherein the molecular weight of said polyester is from 800 to 100,000 in terms of number average molecular weight.
[claim15]
15. The polyester of claim 1, wherein the Tg of said polyester is from 80-200 deg. C.
[claim16]
16. The charge transport material of claim 7, wherein the material is in the form of a hole transport layer of an organic electroluminescent (EL) device or solar cell.
[claim17]
17. The polyester of claim 1, which is a polyester of 9-hydroxy-9-fluorene carboxylic acid.
[claim18]
18. The polyester of claim 1, wherein each Ar ring is phenyl.
  • Inventor, and Inventor/Applicant
  • NAKANO TAMAKI
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
IPC(International Patent Classification)
Reference ( R and D project ) PRESTO Conversion and Control by Advanced Chemistry AREA
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