Arylene containing polymer and organic light-emitting device including the same

1. A polymer comprising Formula 1 below:

wherein in Formula 1, Ar 1 is each independently represented by -(Q 1 ) n -, wherein Q 1 is selected from the group consisting of a substituted or unsubstituted C 5 -C 30 arylene group, a substituted or unsubstituted C 4 -C 30 heteroarylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, and a group represented by —N(Z 1 )—, wherein n is an integer from 1 to 10, and n groups of Q 1 in -(Q 1 ) n - are identical to or different from each other, and

wherein X 1 and X 2 are each independently selected from the group consisting of —O—, —S—, —N(Z 2 )—, and —C(Z 3 )(Z 4 )—, and

wherein R 1 , R 2 , Z 1 , Z 2 , Z 3 , and Z 4 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted C 3 -C 12 cycloalkyl group, a substituted or unsubstituted C 3 -C 12 cycloheteroalkyl group, a substituted or unsubstituted C 5 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 heteroaryl group, and

wherein a and b are independently a number from 0.01 to 0.99, wherein a+b=1.

2. The polymer of claim 1 , wherein Q 1 is selected from the group consisting of a substituted or unsubstituted C 5 -C 14 arylene group, a substituted or unsubstituted C 4 -C 14 heteroarylene group, a substituted or unsubstituted C 2 -C 10 alkenylene group, and a group represented by —N(Z 1 )—;

wherein Z 1 is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 3 -C 12 cycloalkyl group, a substituted or unsubstituted C 3 -C 12 cycloheteroalkyl group, a substituted or unsubstituted C 5 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 heteroaryl group.

3. The polymer of claim 1 , wherein Q 1 is selected from the group consisting of a C 2 -C 10 alkenylene group and Formulae 2a through 2x below:

wherein in Formulae 2a through 2x, T 1 through T 4 are each independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 2 -C 10 alkenyl group, a C 5 -C 14 aryl group, a C 4 -C 14 heteroaryl group, and a group represented by —N(Z 5 )(Z 6 );

p, q, r, and s are each independently an integer from 0 through 4;

Z 5 and Z 6 are each independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 2 -C 10 alkenyl group, a C 5 -C 14 aryl group, and a C 4 -C 14 heteroaryl group; and

p groups of T 1 in -(T 1 ) p are identical to or different from each other, q groups of T 2 in -(T 2 ) q are identical to or different from each other, r groups of T 3 in -(T 3 ), are identical to or different from each other, and s groups of T 4 in -(T 4 ), are identical to or different from each other.

4. The polymer of claim 3 , wherein T 1 through T 4 are each independently selected from the group consisting of hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, and a group represented by —N(Z 5 )(Z 6 ), and Z 5 and Z 6 are each independently selected from the group consisting of hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, and a naphthyl group.

5. The polymer of claim 1 , wherein n is 1, 2, 3, 4, 5, or 6.

6. The polymer of claim 1 , wherein Ar 1 is each independently selected from the group consisting of Formulae 2a through 2x and Formulae 3a through 31 below:

wherein in Formulae 2a through 2x and Formulae 3a through 31, T 1 through T 4 are each independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 2 -C 10 alkenyl group, a C 5 -C 14 aryl group, a C 4 -C 14 heteroaryl group, and a group represented by —N(Z 5 )(Z 6 );

Z 5 and Z 6 are each independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 2 -C 10 alkenyl group, a C 5 -C 14 aryl group, and a C 4 -C 14 heteroaryl group;

p, q, r, and s are each independently an integer from 0 to 4; and

p groups of T 1 in -(T 1 ) p are identical to or different from each other, q groups of T 2 in -(T 2 ) q are identical to or different from each other, r groups of T 3 in -(T 3 ), are identical to or different from each other, and s groups of T 4 in -(T 4 ), are identical to or different from each other.

7. The polymer of claim 1 , wherein Ar 1 is represented by Formula 2d, and T 1 and T 2 of Formula 2d are hydrogen, and T 3 and T 4 are each independently selected from the group consisting of hydrogen, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkoxy group:

8. The polymer of claim 1 , wherein Ar 1 is represented by Formula 2e below, and T 1 and T 2 of Formula 2e are hydrogen, and T 3 and T 4 are each independently selected from the group consisting of hydrogen, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkoxy group:

9. The polymer of claim 1 , wherein each of X 1 and X 2 are —O—.

10. The polymer of claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of a C 5 -C 14 aryl group; a C 4 -C 14 heteroaryl group; a C 5 -C 14 aryl group substituted with at least one selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 5 -C 14 aryl group; and a C 4 -C 14 heteroaryl group substituted with at least one selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 5 -C 14 aryl group.

11. The polymer of claim 1 , wherein R 1 and R 2 are each represented by Formula 4a below:

wherein T 10 in Formula 4a is selected from the group consisting of hydrogen, a halogen atom, a hydroxyl group, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 5 -C 14 aryl group, and a C 4 -C 14 heteroaryl group, and m groups of T 10 of -(T 10 ) m are identical to or different from each other, and m is an integer from 0 to 4.

12. The polymer of claim 1 , wherein a and b are each independently a number from 0.3 to 0.7.

13. The polymer of claim 1 , wherein the polymer is represented by Formula 6 or Formula 7 below:

wherein in Formulae 6 and 7, T 10 , T 3 , and T 4 are each independently selected from the group consisting of hydrogen, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkoxy group, and a and b are each independently a number in a range of 0.01 to 0.99, and a+b=1.

14. The polymer of claim 1 , wherein the polymer has an average weight molecular weight (Mw) of from about 10,000 through about 200,000.

15. The polymer of claim 1 , wherein the polymer has polydispersion index (PDI) of from about 1.5 through about 5.

16. An organic light emitting device (OLED) comprising: a substrate; a first electrode; a second electrode; and a first layer comprising the polymer of claim 1 and disposed between the first and second electrodes.

17. The organic light emitting device (OLED) of claim 16 , wherein the first layer is a hole transporting layer.

18. The organic light emitting device (OLED) of claim 16 , further comprising at least one layer selected from the group consisting of a conductive buffer layer, a hole injection layer, a hole transporting layer, an emissive layer, a hole blocking layer, an electron transporting layer, and an electron injection layer, and disposed between the first and second electrodes.

19. An organic light emitting device (OLED) comprising: a substrate; a first electrode; a second electrode; and a first layer comprising a polymer disposed between the first and second electrodes;

wherein the polymer is represented by Formula 6 or Formula 7 below:

wherein in Formulae 6 and 7, T 10 , T 3 , and T 4 are each independently selected from the group consisting of hydrogen, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkoxy group, and a and b are each independently a number in a range of 0.01 to 0.99, and a+b=1.

20. The organic light emitting device (OLED) of claim 19 , wherein the polymer has an average weight molecular weight (Mw) of from about 10,000 through about 200,000.

21. A polymer comprising Formula 1 below:

wherein in Formula 1, Ar 1 is each independently represented by -(Q 1 ) n -, wherein Q 1 is selected from the group consisting of a C 2 -C 10 alkenylene group, Formula 2e, Formula 2i, Formula 2j, Formula 2k, Formula 21 and Formula 2n through 2v below,

wherein n is an integer from 1 to 10, and n groups of Q 1 in -(Q 1 ) n - are identical to or different from each other, and

wherein X 1 and X 2 are each independently selected from the group consisting of —O—, —S—, —N(Z 2 )—, and —C(Z 3 )(Z 4 )—, and

wherein R 1 , R 2 , Z 2 , Z 3 , and Z 4 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 3 -C 12 cycloalkyl group, a substituted or unsubstituted C 3 -C 12 cycloheteroalkyl group, a substituted or unsubstituted C 5 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 heteroaryl group, and

wherein a and b are independently a number from 0.01 to 0.99, wherein a+b=1:

wherein in Formulae 2e, 2i, 2j, 2k, 21 and 2n through 2v, T 1 through T 4 are each independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 2 -C 10 alkenyl group, a C 5 -C 14 aryl group, a C 4 -C 14 heteroaryl group, and a group represented by —N(Z 5 )(Z 6 );

p, q, r, and s are each independently an integer from 0 through 4, provided that r and s in Formula 2e are 0;

Z 5 and Z 6 are each independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 2 -C 10 alkenyl group, a C 5 -C 14 aryl group, and a C 4 -C 14 heteroaryl group; and

p groups of T 1 in -(T 1 ) p are identical to or different from each other, q groups of T 2 in -(T 2 ) q are identical to or different from each other, r groups of T 3 in -(T 3 ), are identical to or different from each other, and s groups of T 4 in -(T 4 ), are identical to or different from each other.