ORGANIC ELECTROLUMINESCENT DEVICE

• US 20100171418A1
• Filed: 01/06/2010
• Published: 07/08/2010
• Est. Priority Date: 01/06/2009
• Status: Active Grant

• Current Assignee: UDC Ireland Limited
• Original Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Inventors: TAKEDA, Akira, ISE, Toshihiro, KATO, Takashi, INOUE, Masaaki, TAKIZAWA, Hiroo, KINOSHITA, Ikuo
• Granted Patent: US 8,420,234 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

An organic electroluminescent device is provided and includes: a pair of electrodes; an organic layer including a light emitting layer between the electrodes. The organic layer contains a compound represented by formula (I).

In formula (I), R₁₁, R₁₂, and R₁₃ each independently represents a C_1-6 alkyl group, Q₁ represents a carbon atom or a silicon atom, R₁₄ represents a hydrogen atom or -Q₂(R₁₆)(R₁₇)R₁₈ in which Q₂ represents a carbon atom or a silicon atom and R₁₆, R₁₇, and R₁₈ each independently represents a C_1-6 alkyl group, R₁₅ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and n stands for 1 or 2.

Claims

1. An organic electroluminescent device comprising:

a pair of electrodes;

an organic layer including a light emitting layer between the electrodes, wherein the organic layer contains a compound represented by formula (I);

wherein R₁₁, R₁₂, and R₁₃ each independently represents a C_1-6 alkyl group, Q₁ represents a carbon atom or a silicon atom, R₁₄ represents a hydrogen atom or -Q₂(R₁₆)(R₁₇)R₁₈ in which Q₂ represents a carbon atom or a silicon atom and R₁₆, R₁₇, and R₁₈ each independently represents a C_1-6 alkyl group, R₁₅ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and n stands for 1 or 2.

2. The organic electroluminescent device according to claim 1, wherein the compound represented by formula (I) is a compound represented by formula (II):

wherein, R₂₁, R₂₂, and R₂₃ each independently represents a C_1-6 alkyl group, R₂₄ represents a hydrogen atom or —

C(R₂₆)(R₂₇)R₂₈ in which R₂₆, R₂₇, and R₂₈ each independently represents a C_1-6 alkyl group, R₂₅ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

3. The organic electroluminescent device according to claim 2, wherein the compound represented by formula (II) is a compound represented by formula (III):

wherein R₃₁ represents a C_1-6 alkyl group, R₃₄ represents a hydrogen atom or —

C(CH₃)₂R₃₆ in which R₃₆ represents a C_1-6 alkyl group, R₃₅ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

4. The organic electroluminescent device according to claim 3, wherein the compound represented by formula (III) is a compound represented by formula (IV):

wherein R₄₁ represents a methyl or ethyl group, R₄₄ represents a hydrogen atom or —

C(CH₃)₂R₄₆ in which R₄₆ represents a methyl or ethyl group, R₄₅ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

5. The organic electroluminescent device according to claim 4, wherein the compound represented by formula (IV) is a compound represented by formula (V):

wherein R₅₁ represents a methyl or ethyl group and R₅₅ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

6. The organic electroluminescent device according to claim 5, wherein R₅₅ is a hydrogen atom.

7. The organic electroluminescent device according to claim 1, wherein the compound represented by formula (I) is a compound represented by formula (VII):

wherein R₇₁, R₇₂, and R₇₃ each independently represents a C_1-6 alkyl group, R₇₄ represents a hydrogen atom or —

C(R₇₆)(R₇₇)R₇₈ in which R₇₆, R₇₇, and R₇₈ each independently represents a C_1-6 alkyl group, and R₇₅ and R₇₉ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

8. The organic electroluminescent device according to claim 7, wherein the compound represented by formula (VII) is a compound represented by formula (VIII):

wherein R₈₁ represents a C_1-6 alkyl group, R₈₄ represents a hydrogen atom or —

C(CH₃)₂R₈₆ in which R₈₆ represents a C_1-6 alkyl group, and R₈₅ and R₈₉ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

9. The organic electroluminescent device according to claim 8, wherein the compound represented by formula (VIII) is a compound represented by formula (IX):

wherein R₉₁ represents a methyl or ethyl group, R₉₄ represents a hydrogen atom or —

C(CH₃)₂R₉₆ in which R₉₆ represents a methyl or ethyl group, and R₉₅ and R₉₉ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

10. The organic electroluminescent device according to claim 9, wherein the compound represented by formula (IX) is a compound represented by formula (X):

wherein R₁₀₁ represents a methyl or ethyl group, R₁₀₅ and R₁₀₉ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

11. The organic electroluminescent device according to claim 10, wherein each of R₁₀₅ and R₁₀₉ is a hydrogen atom.

12. The organic electroluminescent device according to claim 1, wherein the compound represented by formulae has T₁ of 61 kcal/mol or greater.

13. The organic electroluminescent device according to claim 1, wherein the compound represented by formulae (I) has a molecular weight of from 450 to 1200.

14. The organic electroluminescent device according to claim 1, wherein the light emitting layer further contains at least one phosphorescent metal complex containing a metal having an atomic weight of 40 or greater and a monoanionic bidentate ligand represented by one of formulae (A1) to (A4):

wherein E_1a to E_1q each independently represents a carbon atom or a hetero atom, R_1a to R_1i each independently represents a hydrogen atom or a substituent, and skeletons represented by the formulae (A1) to (A4) each has a 18π

electronic structure in total.

15. The organic electroluminescent device according to claim 1, wherein the light emitting layer further contains at least one tetradentate platinum complex represented by formula (1):

wherein X¹, X², X³, and X⁴ each independently represents a carbon atom or a nitrogen atom, with the proviso that at least one of X¹, X², X³, and X⁴ represents a nitrogen atom, X⁵, X⁶, X⁷, X^s, X⁹, and X¹⁰ each independently represents a carbon atom or a nitrogen atom, X¹¹ and X¹² each independently represents a carbon atom or a nitrogen atom, X¹³, X¹⁴, and X¹⁵ each independently represents a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom, with the proviso that the number of nitrogen atoms contained in a 5-membered ring skeleton represented by X¹¹, X¹², X¹³, X¹⁴, and X¹⁵ is 2 or less, and L represents a single bond or a divalent linking group.

16. The organic electroluminescence according to claim 10, wherein the light emitting layer contains a compound represented by formula (a):

wherein R₁ to R₄ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an alkoxy group, an acyl group, an acyloxy group, an amino group, a nitro group, a cyano group, an ester group, an amide group, a halogen group, a perfluoroalkyl group, or a silyl group, with the proviso that at least one of R₁ to R₄ is a group having a double bond or a triple bond, and X₁ to X₁₂ each independently represents a hydrogen atom, an alkyl group, an alkynyl group, an aryl group, a heteroaryl group, an alkoxy group, an acyl group, an acyloxy group, an amino group, a nitro group, a cyano group, an ester group, an amide group, a halogen group, a perfluoroalkyl group, or a silyl group.