IP Library Granted Patent US 8,004,177
Granted Patent B2
US 8,004,177 · App. 11/517,480 · Granted Aug 23, 2011

Conducting polymer composition and electronic device including layer obtained using the conducting polymer composition

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Quick Facts
Patent No.
US 8,004,177
App. No.
11/517,480
Granted
Aug 23, 2011
Kind
B2
Abstract

Provided are a conducting polymer composition and an electronic device including a layer formed using the conducting polymer composition. The conducting polymer composition contains: at least one compound selected from the group consisting of a siloxane compound of formula (1) below, a siloxane compound of formula (2) below, and a silane compound of formula (3) below; and a conducting polymer: where R 1 , R 2 , X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , D, p, m, q, and r are the same as described in the detailed description of the invention. The electronic device including a layer formed using the conducting polymer composition has excellent electroluminescent characteristics and long lifetime.

Claims (71)

1. A conducting polymer composition, comprising:

a conducting polymer;

at least one compound selected from the group consisting of a siloxane compound of formula (1), a siloxane compound of formula (2), and a silane compound of formula (3):

where each of R 1 and R 2 is independently selected from the group consisting of —CH 2 (CH 2 ) m SiX 1 X 2 X 3 , —O—SiX 4 X 5 X 6 , a cross-linkable unit, a hole transport unit, an electron transport unit, an emissive unit, hydrogen, a halogen atom, a C 1 -C 20 alkyl group, and a C 6 -C 30 aryl group, and at least one of R 1 and R 2 is —CH 2 (CH 2 ) m SiX 1 X 2 X 3 , —O—SiX 4 X 5 X 6 , or a cross-linkable unit;

each of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , and X 20 is independently selected from the group consisting of a cross-linkable unit, a hole transport unit, an electron transport unit, an emissive unit, hydrogen, and a C 1 -C 20 alkyl group, and at least one of X 1 , X 2 , and X 3 , at least one of X 4 , X 5 , and X 6 , at least one of X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , and X 14 , and at least one of X 15 , X 16 , X 17 , X 18 , X 19 , and X 20 are a cross-linkable unit;

D is a C 1 -C 20 alkylene group, a C 1 -C 20 alkylene group substituted with at least one halogen atom, a C 1 -C 20 alkylene group substituted with at least one hole transport unit, electron transport unit or emissive unit, or a divalent hole transport unit;

p is an integer from 3 to 8;

m is an integer from 1 to 10;

q is zero or an integer from 1 to 10;

r is zero or an integer from 1 to 10;

q X 10 are the same or different;

q X 11 are the same or different; and

r D are the same or different; and

the cross-linkable unit in the siloxane compound of formula (2) is one of a hydroxyl group, a C 1 -C 20 alkoxy group, and a halogen atom; and

at least one selected from the group consisting of an acid, metal nanoparticles and inorganic nanoparticles.

2. The conducting polymer composition of claim 1 , wherein the cross-linkable unit is one of a hydroxyl group, a C 1 -C 20 alkoxy group, and a halogen atom.

3. The conducting polymer composition of claim 1 , wherein said at least one compound includes at least one hole-transport unit, and the hole transport unit is selected from the group consisting of

where each of Q 1 , Q 2 , Q 3 , Q 4 , and Q 5 is independently N, O, or S.

4. The conducting polymer composition of claim 1 , wherein said at least one compound includes the electron transport unit, and the electron transport unit is selected from the group consisting of

where each of Q 6 , Q 7 and Q 8 is independently N, O, or S.

5. The conducting polymer composition of claim 1 , wherein said at least one compound includes the emissive unit, and the emissive unit is a C 6 -C 30 aromatic cyclic system or a C 5 -C 30 hetero aromatic cyclic system.

6. The conducting polymer composition of claim 1 , wherein said at least one compound includes the siloxane compound of formula (1), and the siloxane compound of formula (1) is represented by one of formulae (1a), (1b), (1c), (1d), (1e), (1f), and (1g):

7. The conducting polymer composition of claim 1 , wherein the siloxane compound of formula (2) is represented by one of formulae (2a), (2b), (2c), and (2d):

8. The conducting polymer composition of claim 1 , wherein the silane compound of formula (3) is represented by one of formulae (3a), (3b), (3c), and (3d):

9. The conducting polymer composition of claim 1 , wherein the conducting polymer is selected from the group consisting of polythiophene, polyaniline, polypyrrole, polyacetylene, polyvinylenephenylene, polyphenylene, polyfluorene, poly(ethylenedioxythiophene), poly(arylamine), and a derivative thereof, etc.

10. The conducting polymer composition of claim 1 , wherein said at least one compound selected from the group consisting of the siloxane compound of formula (1), the siloxane compound of formula (2), and the silane compound of formula (3), and the conducting polymer are contained in a weight ratio of 0.01:99.9 to 20:80.

11. The conducting polymer composition of claim 1 , further comprising an acid.

12. The conducting polymer composition of claim 11 , wherein the acid include at least one of an atom selected from the group consisting of C, S, N, O, Si, F, Cl, and H; and a functional group selected from the group consisting of a hydroxyl group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a halogen atom, a cyano group, a nitro group, a C 6 -C 30 aryl group, a C 1 -C 20 alkylamino group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylamino group, a C 1 -C 20 alkyl epoxy group, a vinyl group, a C 1 -C 20 alkylmercapto, an acetoxy group, a thiol group, and an imide group.

13. The conducting polymer composition of claim 11 , wherein the acid includes organic ions selected from the group consisting of sulfonic acid, phosphonic acid, and carboxylic acid, and counter ions selected from the group consisting of H and alkali metal ions.

14. The conducting polymer composition of claim 1 , further comprising a crosslinking agent.

15. The conducting polymer composition of claim 1 , further comprising at least one of metal nanoparticles and inorganic nanoparticles.

16. An electronic device comprising a layer obtained from the conducting polymer composition of claim 1 .

17. The electronic device of claim 16 , being an organic light-emitting device.

18. The electronic device of claim 17 , wherein the layer is a hole injecting layer or a hole transporting layer.

19. The electronic device of claim 16 , being one of a photovoltaic device, an electrochromic device, an electrophoretic device, an organic thin film transistor, and an organic memory device.

20. A conducting polymer composition, comprising:

a conducting polymer; and

at least one compound selected from the group consisting of siloxane compounds of formulae (1), (2a), (2c) and (2d) and silane compounds of formulae (3a), (3b), (3c), and (3d):

where each of R 1 and R 2 is independently selected from the group consisting of —CH 2 (CH 2 ) m SiX 1 X 2 X 3 , —O—SiX 4 X 5 X 6 , a cross-linkable unit, a hole transport unit, an electron transport unit, an emissive unit, hydrogen, a halogen atom, a C 1 -C 20 alkyl group, and a C 6 -C 30 aryl group, and at least one of R 1 and R 2 is —CH 2 (CH 2 ) m SiX 1 X 2 X 3 , —O—SiX 4 X 5 X 6 , or a cross-linkable unit;

each of X 1 , X 2 , X 3 , X 4 , X 5 and X 6 , is independently selected from the group consisting of a cross-linkable unit, a hole transport unit, an electron transport unit, an emissive unit, hydrogen, and a C 1 -C 20 alkyl group, and at least one of X 1 , X 2 , and X 3 and at least one of X 4 , X 5 , and X 6 , are a cross-linkable unit;

p is an integer from 3 to 8;

m is an integer from 1 to 10;

21. The conducting polymer composition of claim 20 , wherein said at least one compound and the conducting polymer are contained in a weight ratio of 0.01:99.9-20:80.

22. A conducting polymer composition comprising:

a conducting polymer; and

at least one compound selected from the group consisting of a siloxane compound of formula (1), a siloxane compound of formula (2), and a silane compound of formula (3):

where each of R 1 and R 2 is independently selected from the group consisting of —CH 2 (CH 2 ) m SiX 1 X 2 X 3 , —O—SiX 4 X 5 X 6 , a cross-linkable unit, a hole transport unit, an electron transport unit, an emissive unit, hydrogen, a halogen atom, a C 1 -C 20 alkyl group, and a C 6 -C 30 aryl group, and at least one of R 1 and R 2 is —CH 2 (CH 2 ) m SiX 1 X 2 X 3 , —O—SiX 4 X 5 X 6 , or a cross-linkable unit;

each of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , and X 20 is independently selected from the group consisting of a cross-linkable unit, a hole transport unit, an electron transport unit, an emissive unit, hydrogen, and a C 1 -C 20 alkyl group, and at least one of X 1 , X 2 , and X 3 , at least one of X 4 , X 5 , and X 6 , at least one of X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , and X 14 , and at least one of X 15 , X 16 , X 17 , X 18 , X 19 , and X 20 are a cross-linkable unit;

D is a C 1 -C 20 alkylene group, a C 1 -C 20 alkylene group substituted with at least one halogen atom, a C 1 -C 20 alkylene group substituted with at least one hole transport unit, electron transport unit or emissive unit, or a divalent hole transport unit;

p is an integer from 3 to 8;

m is an integer from 1 to 10;

q is zero or an integer from 1 to 10;

r is zero or an integer from 1 to 10;

q X 10 are the same or different;

q X 11 are the same or different; and

r D are the same or different; and

the cross-linkable unit in the siloxane compound of formula (2) is one of a hydroxyl group, a C 1 -C 20 alkoxy group, and a halogen atom; and

wherein said at least one compound includes at least one of the electron transport unit and the emissive unit;

when said at least one compound includes the electron transport unit, the electron transport unit is selected from the group consisting of

where each of Q 6 , Q 7 and Q 8 is independently N, O, or S; and

when said at least one compound includes the emissive unit, the emissive unit is a C 6 -C 30 aromatic cyclic system or a C 5 -C 30 hetero aromatic cyclic system.

23. An organic light-emitting device, comprising:

a first electrode;

a second electrode;

an emitting layer interposed between the first electrode and the second electrode; and

at least one of a hole transporting layer and a hole injecting layer interposed between the emitting layer and the first electrode, said at least one of the hole transporting layer and the hole injecting layer obtained from the conducting polymer composition of claim 22 .

24. An organic light-emitting device, comprising:

a first electrode;

a second electrode;

an emitting layer interposed between the first electrode and the second electrode; and

at least one of a hole transporting layer and a hole injecting layer interposed between the emitting layer and the first electrode, said at least one of the hole transporting layer and the hole injecting layer obtained from the conducting polymer composition of claim 20 .

Assignments (3)
MERGER Recorded Sep 21, 2012
From: SAMSUNG MOBILE DISPLAY CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 029241/0599 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2008
From: SAMSUNG SDI CO., LTD.
To: SAMSUNG MOBILE DISPLAY CO., LTD.
Reel/Frame 022034/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 8, 2006
From: LEE, TAE-WOO; PARK, JONG-JIN; LYU, YI-YEOL; PU, LYONG-SUN; KIM, SANG-YEOL; KIM, MU-GYEOM; HAN, EUN-SIL
To: SAMSUNG SDI CO., LTD.
Reel/Frame 018289/0017 →