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

• US 7,880,164 B2
• Filed: 07/06/2006
• Issued: 02/01/2011
• Est. Priority Date: 12/19/2005
• Status: Active Grant

• Current Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Original Assignee: Samsung Mobile Display Company Limited (Samsung Electronics Co. Ltd.)
• Inventors: Lee, Tae-Woo, Park, Jong-Jin, Lyu, Yi-Yeol
• Primary Examiner(s): Such; Matthew W
• Application Number:
  US11/480,876
• Publication Number:
  US 20070138483A1
• Time in Patent Office: 1,671 Days
• Field of Search: 257/40, 257E51001-E51052, 438/99, 313/504, 428/690
• US Class Current: 257/40
• CPC Class Codes: C08G 77/54 Nitrogen-containing linkages C08G77/485 takes precedence
• CPC Class Codes: C08L 83/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C08L83/10 takes precedence
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

A conducting polymer composition containing a siloxane material of Formula (1) below and a conducting polymer, and an electronic device including a layer formed using the conducting polymer composition:

where A and a are the same as described in the detailed description of the invention. The electronic device including the layer formed using the conducting polymer composition has excellent electrical characteristics and long lifetime.

Claims

1. 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 a conducting polymer composition, the conducting polymer composition, comprising;

a conducting polymer; and

a siloxane material of Formula (1);

2. The organic light-emitting device of claim 1, wherein A is —

(CH₂)_n-MZ₁Z₂Z₃, and at least one of Z₁, Z₂, and Z₃ is the cross-linkable unit selected from the group consisting of a hydroxyl group, a C1-C20 alkoxy group, and a halogen atom.

3. The organic light-emitting device of claim 1, wherein A is —

(CH₂)_n-MZ₁Z₂Z₃, and at least one of Z₁, Z₂, and Z₃ is the hole transport unit selected from the group consisting of;

4. The organic light-emitting device of claim 1, wherein A is —

(CH₂)_n-MZ₁Z₂Z₃, and at least one of Z₁, Z₂, and Z₃ is the electron transport unit selected from the group consisting of;

5. The organic light-emitting device of claim 1, wherein A is —

(CH₂)_n-MZ₁Z₂Z₃, and at least one of Z₁, Z₂, and Z₃ is the emissive unit being a C6-C30 aromatic cyclic system or a C5-C30 hetero aromatic cyclic system, which include one or at least two rings which are fused or are bonded by a single bond or a vinylene group.

6. The organic light-emitting device of claim 1, wherein the siloxane material has Formula (2):

7. The organic light-emitting device of claim 1, wherein the siloxane material has one of Formulae (2a), (2b), and (2c):

8. The organic light-emitting device of claim 1, wherein the weight average molecular weight of the siloxane material of Formula (1) is 500,000 or less.

9. The organic light-emitting device 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.

10. The organic light-emitting device of claim 1, wherein the siloxane material of Formula (1) and the conducting polymer are contained in a weight ratio of 0.01:

99.9 to 20;

80.

11. The organic light-emitting device of claim 1, wherein the conducting polymer composition further comprises acid.

12. The organic light-emitting device 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a halogen atom, a cyano group, a nitro group, a C6-C30 aryl group, a C1-C20 alkylamino group, a C6-C30 aryloxy group, a C6-C30 arylamino group, a C1-C20 alkyl epoxy group, a vinyl group, a C1-C20 alkylmercapto, an acetoxy group, a thiol group, and an imide group.

13. The organic light-emitting device 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 an alkali metal ion.

14. The organic light-emitting device of claim 1, wherein the conducting polymer composition further comprises a crosslinking agent.

15. The organic light-emitting device of claim 1, wherein the conducting polymer composition further comprises at least one of metal nanoparticles and inorganic nanoparticles.

16. The organic light-emitting device of claim 1, wherein the siloxane material is (i) a compound represented by Formula (2), or (ii) a hydrolysate or a condensate of at least one compound selected from the group consisting of the compound of said Formula (2), a compound of Formula (3), a compound of Formula (4), a compound of Formula (5), and a compound of Formula (6):

17. The organic light-emitting device of claim 16, wherein the siloxane material is (i) a compound represented by Formula (2), or (ii) the hydrolysate or the condensate of the compound of Formula (3) and optionally at least one compound selected from the group consisting of the compound of Formula (2), the compound of Formula (4), the compound of Formula (5), and the compound of Formula (6), and the compound of Formula (3) is represented by one of Formulae (3a), (3b), (3c), (3d), (3e), (3f), and (3g):

18. The organic light-emitting device of claim 16, wherein the siloxane material is (i) a compound represented by Formula (2), or (ii) the hydrolysate or the condensate of the compound of Formula (4) and optionally at least one compound selected from the group consisting of the compound of Formula (2), the compound of Formula (3), the compound of Formula (5), and the compound of Formula (6), and the compound of Formula (4) is represented by one of Formulae (4a), (4b), (4c), and (4d):

19. The organic light-emitting device of claim 16, wherein the siloxane material is (i) a compound represented by Formula (2), or (ii) the hydrolysate or the condensate of the compound of Formula (5) and optionally at least one compound selected from the group consisting of the compound of Foimula (2), the compound of Formula (3), the compound of Formula (4), and the compound of Formula (6), and the compound of Formula (5) is represented by one of Formulae (5a), (5b), (5c), (5d), (5e), (5f, and (5g):

20. The organic light-emitting device of claim 16, wherein the siloxane material is (i) a compound represented by Formula (2), or (ii) the hydrolysate or the condensate of the compound of Formula (6) and optionally at least one compound selected from the group consisting of the compound of Formula (2), the compound of Formula (3), the compound of Formula (4), and the compound of Formula (5), and the compound of Formula (6) is represented by one of Formulae (6a) and (6b):

Si(OCH₃)₄  

 

(6a)

SiCH₃(OCH₃)₃  

 

(6b).

21. A conducting polymer composition, comprising:

a conducting polymer; and

a siloxane material of Formula (1);

22. An electronic device comprising a layer obtained from the conducting polymer composition of claim 21.

23. The electronic device of claim 22, being an organic light-emitting device, wherein the layer is at least one of a hole injecting layer and a hole transporting layer.

24. The conducting polymer composition of claim 21, wherein the siloxane material is (i) a compound represented by Formula (2), or (ii) a hydrolysate or a condensate of at least one compound selected from the group consisting of the compound of said Formula (2), a compound of Formula (3), a compound of Formula (4), a compound of Formula (5), and a compound of Formula (6):

25. The conducting polymer composition of claim 21, wherein the siloxane material is (i) a compound represented by Formula (2), or (ii) the hydrolysate or the condensate of the compound of Formula (3) and optionally at least one compound selected from the group consisting of the compound of Formula (2), the compound of Formula (4), the compound of Formula (5), and the compound of Formula (6), and the compound of Formula (3) is represented by one of Formulae (3a), (3b), (3c), (3d), (3e), (3f), and (3g):

26. The conducting polymer composition of claim 21, wherein the siloxane material is (i) a compound represented by Formula (3), or (ii) the hydrolysate or the condensate of the compound of Formula (4) and optionally at least one compound selected from the group consisting of the compound of Formula (2), the compound of Formula (3), the compound of Formula (5), and the compound of Formula (6), and the compound of Formula (4) is represented by one of Formulae (4a), (4b), (4c), and (4d):

27. The conducting polymer composition of claim 21, wherein the siloxane material is (i) a compound represented by Formula (2), or (ii) the hydrolysate or the condensate of the compound of Formula (5) and optionally at least one compound selected from the group consisting of the compound of Formula (2), the compound of Formula (3), the compound of Formula (4), and the compound of Formula (6), and the compound of Formula (5) is represented by one of Formulae (5a), (5b), (5c), (5d), (5e), (5f), and (5g):

28. The conducting polymer composition of claim 21, wherein the siloxane material is (i) a compound represented by Formula (2), or (ii) the hydrolysate or the condensate of the compound of Formula (6) and optionally at least one compound selected from the group consisting of the compound of Formula (2), the compound of Formula (3), the compound of Formula (4), and the compound of Formula (5), and the compound of Formula (6) is represented by one of Formulae (6a) and (6b):

Si(OCH₃)₄ 

 

(6a)

SiCH₃(OCH₃)₃ 

 

(6b).