Light-emitting polymer and organoelectroluminescent display using the same

1. A light-emitting polymer represented by the formula I:

wherein X and U are independently selected from the group consisting of a single bond, —O—, —S—, —CO—, —Si(R′)(R″)—, —N(R′)— and —C(R′)(R″)—, and at least one of X and U is not a single bond;

A, B, C and D are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C3-C20 cyclic alkylene group, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group;

R 1 , R 2 and R 3 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C20 cyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, a hydroxy group, a cyano group, and —N(R′)(R″) in which R′ and R″ are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a substituted or unsubstituted C3-C20 cyclic alkyl group; and

m is a degree of polymerization and is a real number from 5 to 1,000.

2. The light-emitting polymer of claim 1 , wherein the light-emitting polymer of claim 1 further comprises at least one repeating unit of Ar 1 repeating unit and Ar 2 repeating unit, and the light-emitting polymer is represented by the formula II:

wherein X and U are independently selected from the group consisting of a single bond, —O—, —S—, —CO—, —Si(R′)(R″)—, —N(R′)— and —C(R′)(R″)—, and at least one of X and U is not a single bond;

A, B, C and D are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C3-C20 cyclic alkylene group, a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C2-C30 heteroarylene group;

R 1 , R 2 and R 3 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C20 cyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, a hydroxy group, a cyano group and —N(R′)(R″) in which R′ and R″ are independently selected from the group consisting of a hydrogen atom, a C1-C30 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group and a C3-C20 cyclic alkyl group;

Ar 1 and Ar 2 are independently selected from the group consisting of a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C2-C30 heteroarylene group;

m is a degree of polymerization and is a real number from 5 to 1,000; and

a represents 0 to 20% by mole, b represents 60 to 99% by mole, and c represents 0 to 20% by mole, but a and c do not represent simultaneously 0 mole %.

3. The light-emitting polymer of claim 2 , wherein the Ar 1 repeating unit and the Ar 2 repeating unit are independently selected from the group consisting of the formulae IIIa through IIIr:

wherein R 4 and R 5 are independently selected from the group consisting of a hydrogen atom, a C1-C30 alkyl group, a C1-C30 alkoxy group, a C6-C30 aryl group, and —N(R′)(R″) in which R′ and R″ are independently selected from the group consisting of a hydrogen atom, a C1-C12 alkyl group and a C6-C14 aryl group.

4. The light-emitting polymer of claim 1 , wherein the weight-average molecular weight (Mw) of the polymer represented by the formula I is 10,000 to 200,000, and the molecular weight distribution (MWD) is 1.5 to 5.

5. The light-emitting polymer of claim 2 , wherein the weight-average molecular weight (Mw) of the polymer represented by the formula II is 10,000 to 200,000, and the molecular weight distribution (MWD) is 1.5 to 5.

6. The light-emitting polymer of claim 1 , wherein the polymer is represented by the formula IV:

wherein R′ and R″ each represent a C1-C20 alkyl group, and m is a real number from 5 to 1,000.

7. The light-emitting polymer of claim 6 , wherein the polymer is represented by the formula VI:

wherein m is a real number from 5 to 1,000.

8. The light-emitting polymer of claim 2 , wherein the polymer is represented by the formula V:

wherein R, R′ and R″ each represent a C1-C20 alkyl group, m is a real number from 5 to 1,000, b represents 80 to 99% by mole, and c represents 1 to 20% by mole.

9. The light-emitting polymer of claim 8 , wherein the polymer is represented by the formula VII:

wherein m is a real number from 5 to 1,000, b represents 80 to 99% by mole, and c represents 1 to 20% by mole.

10. An organic electroluminescent display comprising an organic film between a pair of electrodes, wherein the organic film comprises the light-emitting polymer of claim 1 .

11. The organic electroluminescent display of claim 10 , wherein the organic film is a light emitting layer.

12. A light-emitting polymer represented by the formula II:

wherein X and U are independently selected from the group consisting of a single bond, —O—, —S—, —CO—, —Si(R′)(R″)—, —N(R′)— and —C(R′)(R″)—, and at least one of X and U is not a single bond;

A, B, C and D are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C3-C20 cyclic alkylene group, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group;

R 1 , R 2 and R 3 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C20 cyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, a hydroxy group, a cyano group, and —N(R′)(R″) in which R′ and R″ are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a substituted or unsubstituted C3-C20 cyclic alkyl group;

m is a degree of polymerization and is a real number from 5 to 1,000;

Ar 1 and Ar 2 are independently selected from the group consisting of a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C2-C30 heteroarylene group; and

a represents 0 to 20% by mole, b represents 60 to 99% by mole, and c represents 0 to 20% by mole.

13. An organic electroluminescent display, comprising:

a pair of electrodes;

a light emitting layer between said pair of electrodes, said light emitting layer comprising a polymer represented by the formula I or the formula II:

wherein X and U are independently selected from the group consisting of a single bond, —O—, —S—, —CO—, —Si(R′)(R″)—, —N(R′)— and —C(R′)(R″)—, and at least one of X and U is not a single bond;

A, B, C and D are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C3-C20 cyclic alkylene group, a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C2-C30 heteroarylene group;

R 1 , R 2 and R 3 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C20 cyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, a hydroxy group, a cyano group and —N(R′)(R″) in which R′ and R″ are independently selected from the group consisting of a hydrogen atom, a C1-C30 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group and a C3-C20 cyclic alkyl group;

Ar 1 and Ar 2 are independently selected from the group consisting of a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C2-C30 heteroarylene group;

m is a degree of polymerization and is a real number from 5 to 1,000; and

a represents 0 to 20% by mole, b represents 60 to 99% by mole, and c represents 0 to 20% by mole, but a and c do not represent simultaneously 0 mole %.

14. The organic electroluminescent display of claim 13 , wherein the Ar 1 repeating unit and the Ar 2 repeating unit are independently selected from the group consisting of the formulae IIIa through IIIr:

wherein R 4 and R 5 are independently selected from the group consisting of a hydrogen atom, a C1-C30 alkyl group, a C1-C30 alkoxy group, a C6-C30 aryl group, and —N(R′)(R″) in which R′ and R″ is selected from the group consisting of a hydrogen atom, a C1-C12 alkyl group and a C6-C14 aryl group.

15. The organic electroluminescent display of claim 13 , wherein the weight-average molecular weight (Mw) of the polymer is 10,000 to 200,000.

16. The organic electroluminescent display of claim 15 , wherein the molecular weight distribution (MWD) of the polymer is 1.5 to 5.

17. The organic electroluminescent display of claim 13 , wherein the polymer is represented by the formula IV:

wherein R′ and R″ each represent a C1-C20 alkyl group, and m is a real number from 5 to 1,000.

18. The organic electroluminescent display of claim 17 , wherein the polymer is represented by the formula VI:

wherein m is a real number from 5 to 1,000.

19. The organic electroluminescent display of claim 13 , wherein the polymer is represented by the formula V:

wherein R, R′ and R″ each represent a C1-C20 alkyl group, m is a real number from 5 to 1,000, b represents 80 to 99% by mole, and c represents 1 to 20% by mole.

20. The organic electroluminescent display of claim 19 , wherein the polymer is represented by the formula VII:

wherein m is a real number from 5 to 1,000, b represents 80 to 99% by mole, and c represents 1 to 20% by mole.