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

• US 8,987,709 B2
• Filed: 09/30/2010
• Issued: 03/24/2015
• Est. Priority Date: 10/09/2009
• Status: Active Grant

• Current Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Original Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Inventors: Kim, Hee-Yeon, Yang, Seung-Gak, Lee, Jae-Yong, Yi, Jeoung-In, Kwak, Yoon-Hyun, Lee, Jong-Hyuk
• Primary Examiner(s): HENRY, CALEB E
• Application Number:
  US12/895,374
• Publication Number:
  US 20110084254A1
• Time in Patent Office: 1,636 Days
• Field of Search: 257/40, 257/E51.027, 313/504, 528/403
• US Class Current: 257/40
• CPC Class Codes: C08G 2261/344 containing heteroatoms
• CPC Class Codes: C08G 2261/512 Hole transport
• CPC Class Codes: C08G 61/122 derived from five- or six-membered heterocyclic compounds, other than imides
• CPC Class Codes: C08G 73/06 Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
• CPC Class Codes: C08G 73/0688 with only one nitrogen atom in the ring, e.g. polyquinolines
• CPC Class Codes: C08G 73/0694 with only two nitrogen atoms in the ring, e.g. polyquinoxalines
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/1135 Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
• CPC Class Codes: H10K 85/115 Polyfluorene; Derivatives thereof
• CPC Class Codes: H10K 85/151 Copolymers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/623 containing five rings, e.g. pentacene

Abstract

A polymer and an organic light-emitting device including the polymer. An example of the polymer is

• • wherein in Formula 1, Ar₁ is each independently represented by -(Q₁)_n-, and Q₁ is selected from the group consisting of a substituted or unsubstituted C₅-C₃₀ arylene group, a substituted or unsubstituted C₄-C₃₀ heteroarylene group, a substituted or unsubstituted C₂-C₃₀ alkenylene group, and a group represented by —N(Z₁)—, and n is an integer from 1 to 10, and n groups of Q₁ in -(Q₁)_n- is identical to or different from each other, and
  • X₁ and X₂ are each independently selected from the group consisting of —O—, —S—, —N(Z₂)—, and —C(Z₃)(Z₄)—.

Claims

1. A polymer comprising Formula 1 below:

2. The polymer of claim 1, wherein Q₁ is selected from the group consisting of a substituted or unsubstituted C₅-C₁₄ arylene group, a substituted or unsubstituted C₄-C₁₄ heteroarylene group, a substituted or unsubstituted C₂-C₁₀ alkenylene group, and a group represented by —

N(Z₁)—

;

wherein Z₁ is selected from the group consisting of hydrogen, a substituted or unsubstituted C₁-C₃₀ alkyl group, a substituted or unsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstituted C₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxy group, a substituted or unsubstituted C₃-C₁₂ cycloalkyl group, a substituted or unsubstituted C₃-C₁₂ cycloheteroalkyl group, a substituted or unsubstituted C₅-C₃₀ aryl group, and a substituted or unsubstituted C₄-C₃₀ heteroaryl group.

3. The polymer of claim 1, wherein Q₁ is selected from the group consisting of a C₂-C₁₀ alkenylene group and Formulae 2a through 2x below:

4. The polymer of claim 3, wherein T₁ through T₄ are each independently selected from the group consisting of hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, and a group represented by —

N(Z₅)(Z₆), and Z₅ and Z₆ are each independently selected from the group consisting of hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ 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 Ar₁ is each independently selected from the group consisting of Formulae 2a through 2x and Formulae 3a through 31 below:

7. The polymer of claim 1, wherein Ar₁ is represented by Formula 2d, and T₁ and T₂ of Formula 2d are hydrogen, and T₃ and T₄ are each independently selected from the group consisting of hydrogen, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group:

8. The polymer of claim 1, wherein Ar₁ is represented by Formula 2e below, and T₁ and T₂ of Formula 2e are hydrogen, and T₃ and T₄ are each independently selected from the group consisting of hydrogen, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group:

9. The polymer of claim 1, wherein each of X₁ and X₂ are —

O—

.

10. The polymer of claim 1, wherein R₁ and R₂ are each independently selected from the group consisting of a C₅-C₁₄ aryl group;

a C₄-C₁₄ heteroaryl group;

a C₅-C₁₄ aryl group substituted with at least one selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₅-C₁₄ aryl group; and

a C₄-C₁₄ heteroaryl group substituted with at least one selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, and a C₅-C₁₄ aryl group.

11. The polymer of claim 1, wherein R₁ and R₂ are each represented by Formula 4a below:

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:

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;

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: