Polymer compound and organic light-emitting device using the same

1. A polymer compound for hole-injection or hole-transportation, the polymer compound represented by Formula 1:

where x and y are each real numbers from 0.01 to 0.99;

R 1 and R 2 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 cycloalkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 4 -C 30 heterocyclic group, and C 6 -C 30 fused aryl group, and R 1 and R 2 can be joined to form a ring;

Ar 1 and Ar 2 are each independently selected from the group consisting of a phenylene, a tolylene, a naphthylene, a stilbenylene, an anthracenylene, a terphenylene, a pyrenylene, a diphenylanthracenylene, a dinaphthylanthracenylene, a pentacenylene, derivatives thereof, a substituted or unsubstituted C 2 -C 30 heteroarylene group, and a substituted or unsubstituted C 2 -C 30 heterocyclic group;

Ar 3 is each independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heterocyclic group, and a C 6 -C 30 fused aryl group;

Ar 4 is each independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heterocyclic group, and a substituted or unsubstituted C 6 -C 30 fused aryl group;

Q is CH═CH, O, S, Se, or (CH 2 ) m where m is a real number from 1 to 10; and

n is the degree of polymerization, and is a real number from 10 to 300.

2. The polymer compound of claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of a hydrogen, a methyl, an ethyl, a propyl, an isopropyl, a butyl, an isobutyl, a pentyl, a hexyl, an ethylhexyl, a heptyl, an octyl, an isooctyl, a nonyl, a decyl, a dodecyl, a hexadecyl, an octadecyl, a docodecyl, a cyclopropyl, a cyclopentyl, a cyclohexyl, an acetyl, an octanoyl, a benzoyl, a methoxy, an ethoxy, an ethylenedioxy, a butoxy, a hexyloxy, a methoxyethoxyethyl, a methoxyethoxyethoxyethyl, a cyanoethyl, a carboxymethyl, a phenyl, a phenoxy, a tolyl, a benzyl, a naphthylanthracenyl, a terphenyl, a pyrenyl, a diphenylanthracenyl, a pentacenyl, a triphenylamine, and derivatives thereof.

3. The polymer compound of claim 1 , wherein Ar 3 is selected from the group consisting of a hydrogen, a phenyl, a tolyl, a naphthyl, a stilbenzyl, a fluorenyl, an anthracenyl, a terphenyl, a pyrenyl, a diphenylanthracenyl, a dinaphthylanthracenyl, a pentacenyl and their derivatives, a hexylphenyl, an octanoylphenyl, a bromophenyl, a hydroxyphenyl, a thienyl, a pyridyl, an azobenzenyl, a ferrocenyl, a carbazoyl, a porphyrin and derivatives thereof.

4. The polymer compound of claim 1 , wherein the polymer compound is represented by Formula 7:

where x and y are each real numbers from 0.01 to 0.99, n is the degree of polymerization and is a real number from 10 to 150.

5. An organic electroluminescent device comprising an organic layer between a pair of electrodes, the organic layer containing the polymer compound of claim 1 .

6. The organic electroluminescent device of claim 5 , wherein the organic layer containing the polymer compound comprises at least one of a hole injection layer and a hole transport layer.

7. The organic electroluminescent device of claim 5 , wherein the organic layer further comprises a dopant.

8. The organic electroluminescent device of claim 7 , wherein the dopant is at least one selected from the group consisting of an acceptor material, an organic metal complex, a metal oxide, and an ion salt.

9. The organic electroluminescent device of claim 5 , wherein the number-average molecular weight (Mn) of the polymer compound is 10,000 through 200,000.

10. A polymer compound for hole-rejection or hole-transportation, the polymer compound represented by Formula 1:

where x and y are each real numbers from 0.01 to 0.99;

R 1 and R 2 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 cycloalkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 4 -C 30 heterocyclic group, and C 6 -C 30 fused aryl group, and R 1 and R 2 can be joined to form a ring;

Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 2 -C 30 heteroarylene group, and a substituted or unsubstituted C 2 -C 30 heterocyclic group;

Ar 3 and Ar 4 are each independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heterocyclic group, and a C 6 -C 30 fused aryl group;

Q is CH═CH; and

n is the degree of polymerization, and is a real number from 10 to 300; and

the number-average molecular weight (Mn) of the polymer compound is 10,000 through 200,000.

11. The polymer compound of claim 10 , wherein R 1 and R 2 are each independently selected from the group consisting of a hydrogen, a methyl, an ethyl, a propyl, an isopropyl, a butyl, an isobutyl, a pentyl, a hexyl, an ethylhexyl, a heptyl, an octyl, an isooctyl, a nonyl, a decyl, a dodecyl, a hexadecyl, an octadecyl, a docodecyl, a cyclopropyl, a cyclopentyl, a cyclohexyl, an acetyl, an octanoyl, a benzoyl, a methoxy, an ethoxy, an ethylenedioxy, a butoxy, a hexyloxy, a methoxyethoxyethyl, a methoxyethoxyethoxyethyl, a cyanoethyl, a carboxymethyl, a phenyl, a phenoxy, a tolyl, a benzyl, a naphthylanthracenyl, a terphenyl, a pyrenyl, a diphenylanthracenyl, a pentacenyl, a triphenylamine, and derivatives thereof;

Ar 1 and Ar 2 are each independently selected from the group consisting of a phenylene, a tolylene, a naphthylene, a stilbenzylene, a fluorenylene, an anthracenylene, a terphenylene, a pyrenylene, a diphenylanthracenylene, a dinaphthylanthracenylene, a pentacenylene, and derivatives thereof; and

Ar 3 and Ar 4 are selected from the group consisting of a hydrogen, a phenyl, a tolyl, a naphthyl, a stilbenzyl, a fluorenyl, an anthracenyl, a terphenyl, a pyrenyl, a diphenylanthracenyl, a dinaphthylanthracenyl, a pentacenyl and their derivatives, a hexylphenyl, an octanoylphenyl, a bromophenyl, a hydroxyphenyl, a thienyl, a pyridyl, an azobenzenyl, a ferrocenyl, a carbazoyl, a porphyrin and derivatives thereof.

12. An organic electroluminescent device comprising an organic layer between a pair of electrodes, wherein the organic layer contains the polymer compound of claim 10 .

13. An organic electroluminescent device, comprising:

a first electrode;

a second electrode; and

an organic layer between the first electrode and the second electrode, the organic layer comprising an emissive layer and at least one of a hole injection layer and a hole transport layer between the emissive layer and the first electrode, said at least one of the hole injection layer and the hole transport layer comprising a polymer represented by Formula 1:

where x and y are each real numbers from 0.01 to 0.99;

R 1 and R 2 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 cycloalkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 4 -C 30 heterocyclic group, and C 6 -C 30 fused aryl group, and R 1 and R 2 can be joined to form a ring;

Ar 1 and Ar 2 are each independently selected from the group consisting of a phenylene, a tolylene, a naphthylene, a stilbenylene, an anthracenylene, a terphenylene, a pyrenylene, a diphenylanthracenylene, a dinaphthylanthracenylene, a pentacenylene, derivatives thereof, a substituted or unsubstituted C 2 -C 30 heteroarylene group, and a substituted or unsubstituted C 2 -C 30 heterocyclic group;

Ar 3 is each independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heterocyclic group, and a C 6 -C 30 fused aryl group;

Ar 4 is each independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heterocyclic group, and a substituted or unsubstituted C 6 -C 30 fused aryl group;

Q is CH═CH, O, S, Se, or (CH 2 ) m , where m is a real number from 1 to 10; and

n is the degree of polymerization, and is a real number from 10 to 300.

14. The organic electroluminescent device of claim 13 , wherein R 1 and R 2 are each independently selected from the group consisting of a hydrogen, a methyl, an ethyl, a propyl, an isopropyl, a butyl, an isobutyl, a pentyl, a hexyl, an ethylhexyl, a heptyl, an octyl, an isooctyl, a nonyl, a decyl, a dodecyl, a hexadecyl, an octadecyl, a docodecyl, a cyclopropyl, a cyclopentyl, a cyclohexyl, an acetyl, an octanoyl, a benzoyl, a methoxy, an ethoxy, an ethylenedioxy, a butoxy, a hexyloxy, a methoxyethoxyethyl, a methoxyethoxyethoxyethyl, a cyanoethyl, a carboxymethyl, a phenyl, a phenoxy, a tolyl, a benzyl, a naphthylanthracenyl, a terphenyl, a pyrenyl, a diphenylanthracenyl, a pentacenyl, a triphenylamine, and derivatives thereof;

Ar 1 and Ar 2 are each independently selected from the group consisting of a phenylene, a tolylene, a naphthylene, a stilbenzylene, an anthracenylene, a terphenylene, a pyrenylene, a diphenylanthracenylene, a dinaphthylanthracenylene, a pentacenylene, and derivatives thereof;

Ar 3 is selected from the group consisting of a hydrogen, a phenyl, a tolyl, a naphthyl, a stilbenzyl, a fluorenyl, an anthracenyl, a terphenyl, a pyrenyl, a diphenylanthracenyl, a dinaphthylanthracenyl, a pentacenyl and their derivatives, a hexylphenyl, an octanoylphenyl, a bromophenyl, a hydroxyphenyl, a thienyl, a pyridyl, an azobenzenyl, a ferrocenyl, a carbazoyl, a porphyrin and derivatives thereof; and

Ar 4 is selected from the group consisting of a hydrogen, a thienyl, a pyridyl, a carbazoyl, a porphyrin and derivatives thereof.

15. The organic electroluminescent device of claim 13 , wherein the polymer compound is represented by Formula 7:

where x and y are each real numbers from 0.01 to 0.99, n is the degree of polymerization and is a real number from 10 to 150, and Hex is a hexyl group.

16. The organic electroluminescent device of claim 13 , wherein the emissive layer further comprises a dopant.

17. The organic electroluminescent device of claim 16 , wherein the dopant is at least one selected from the group consisting of an acceptor material, an organic metal complex, a metal oxide, and an ion salt.

18. The organic electroluminescent device of claim 16 , wherein the number-average molecular weight (Mn) of the polymer compound is 10,000 through 200,000.

19. The organic electroluminescent device of claim 16 , wherein the emissive layer is formed of at least one selected from the group consisting of a green-phosphorescence dopant and a red-phosphorescence dopant.