Composition for organic photoelectronic element, organic photoelectronic element, and display apparatus

• US 10,644,245 B2
• Filed: 05/11/2016
• Issued: 05/05/2020
• Est. Priority Date: 06/19/2015
• Status: Active Grant

• Current Assignee: Samsung SDI Company Limited
• Original Assignee: Samsung SDI Company Limited
• Inventors: Lee, Sangshin, Kang, Giwook, Kang, Dong Min, Kim, Youngkwon, Yu, Eun Sun, Lee, Byoungkwan, Jang, Kipo, Park, Youngsung
• Primary Examiner(s): Clark, Gregory D
• Application Number:
  US15/540,090
• Publication Number:
  US 20180006238A1
• Time in Patent Office: 1,455 Days
• Field of Search: None
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 251/24 to three ring carbon atoms
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 403/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C09K 11/02 Use of particular materials as binders, particle coatings or suspension media therefor
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/90 Multiple hosts in the emissive layer
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

The present invention relates to: a composition for an organic photoelectronic element comprising at least one type of a first chemical compound represented by chemical formula 1 and at least one type of a second chemical compound represented by chemical formula 2; an organic photoelectronic element comprising the same; and a display apparatus comprising said organic photoelectronic element. Chemical formulas 1 and 2 are described in the specification of the present invention.

Claims

1. A composition for an organic optoelectronic device, the composition comprising:

at least one first compound and at least one second compound mixed together, the at least one first compound being represented by Chemical Formula 1 and the at least one second compound being represented by Chemical Formula 2,

2. The composition for an organic optoelectronic device of claim 1, wherein the Chemical Formula 1 is represented by one of Chemical Formula 1-I to Chemical Formula 1-III:

3. The composition for an organic optoelectronic device of claim 1, wherein the L¹ is:

a phenylene group that is unsubstituted or substituted with deuterium, a C1 to C40 silyl group, a C to C30 alkyl group, or a C6 to C30 aryl group;

a biphenylene group that is unsubstituted or substituted with deuterium, a C1 to C40 silyl group, a C1 to C30 alkyl group, or a C6 to C30 aryl group;

a terphenylene group that is unsubstituted or substituted with deuterium, a C to C40 silyl group, a C1 to C30 alkyl group, or a C6 to C30 aryl group;

or

a quarterphenylene group that is unsubstituted or substituted with deuterium, a C1 to C40 silyl group, a C1 to C30 alkyl group, or a C6 to C30 aryl group.

4. The composition for an organic optoelectronic device of claim 1, wherein the L¹ is selected from substituted or unsubstituted linking groups of Group 2:

[Group 2]

5. The composition for an organic optoelectronic device of claim 1, wherein X¹ to X¹² of Chemical Formula 1 are independently N, C, or CR^a,

three of X¹ to X⁶ are N,

one to three of X⁷ to X¹² are N,

R^a is independently, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and

L¹ is a C6 to C30 arylene group that is substituted or unsubstituted with deuterium, a C1 to C30 alkyl group, or a C6 to C30 aryl group,

wherein “

substituted”

refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxy group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, or a C2 to C30 heterocyclic group.

6. The composition for an organic optoelectronic device of claim 5, wherein the R^a is a substituted or unsubstituted C6 to C30 aryl group,

wherein the C6 to C30 aryl group is substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quarterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted phenanthrenyl group.

7. The composition for an organic optoelectronic device of claim 1, wherein the Chemical Formula 2 is represented by one of Chemical Formulae 2-I to 2-VI:

8. The composition for an organic optoelectronic device of claim 7, wherein Ar¹ and Ar² of Chemical Formulae 2-I to 2-VI are independently, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

9. The composition for an organic optoelectronic device of claim 7, wherein Ar¹ and Ar² of Chemical Formula 2-I to 2-VI are selected from substituted or unsubstituted groups of Group 4:

[Group 4]

10. The composition for an organic optoelectronic device of claim 1, wherein the first compound is represented by Chemical Formula 1-Ia, and

the second compound is represented by Chemical Formula 1a or 2a-1

11. The composition for an organic optoelectronic device of claim 1, which further comprises a phosphorescent dopant.

12. An organic optoelectronic device, comprising:

an anode and a cathode facing each other, and

one or more organic layers interposed between the anode and the cathode, wherein the composition for an organic optoelectronic device of claim 1 forms a same organic layer of the one or more organic layers, the at least one first compound and at least one second compound being simultaneously present as a mixture in the same organic layer.

13. The organic optoelectronic device of claim 12, wherein the same organic layer is an emission layer in which the at least one first compound and at least one second compound are present in the mixture.

14. The organic optoelectronic device of claim 12, wherein the organic optoelectronic device is selected from an organic light emitting diode, an organic photoelectric device, an organic solar cell, an organic transistor, an organic photo conductor drum, and an organic memory device.

15. A display device comprising the organic optoelectronic device of claim 12.

16. A composition for an organic optoelectronic device, the composition comprising:

at least one first compound represented by Chemical Formula 1; and

at least one second compound represented by one of Chemical Formulae 2-I to 2-VI,