Organic light-emitting device and organic light-emitting display apparatus including the same

1. An organic light-emitting device comprising:

a first electrode, a second electrode facing the first electrode, a phosphorescent emission layer between the first electrode and the second electrode, and an electron transport layer between the phosphorescent emission layer and the second electrode,

wherein:

the phosphorescent emission layer comprises a compound represented by one of Formulae 1a to 1c, and

the electron transport layer comprises a metal-containing compound and a compound represented by Formula 2:

wherein:

R 1 to R 12 are each independently a hydrogen atom, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxyl group, 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 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, or a substituted or unsubstituted C 6 -C 30 aryl group;

one of Ar 1 or Ar 2 is a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, or a substituted or unsubstituted C 6 -C 30 arylthio group, and the other of Ar 1 and Ar 2 is a substituted or unsubstituted C 2 -C 30 heteroaryl group;

one or two of Ar 11 , A 12 , or Ar 13 are each independently an unsubstituted phenyl group, a substituted or unsubstituted C 7 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, or a substituted or unsubstituted C 6 -C 30 arylthio group, and the others of Ar 11 , A 12 , and Ar 13 are each independently a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted bipyridinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, or a substituted or unsubstituted benzocarbazolyl group;

L 11 , L 12 and L 13 are each independently an unsubstituted phenylene group, or a substituted or unsubstituted C 7 -C 30 arylene group; and

a, b, and c are each independently an integer from 0 to 3.

2. The organic light-emitting device of claim 1 , wherein R 1 to R 12 are each independently a hydrogen atom, a deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted pyrenyl group, and

one of Ar 1 or Ar 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted fluoranthenyl group, and the other of Ar 1 or Ar 2 is a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted bipyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted benzocarbazolyl group.

3. The organic light-emitting device of claim 1 , wherein R 1 to R 12 are each independently a hydrogen atom, a deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, or a substituted or unsubstituted butyl group, and

one of Ar 1 or Ar 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted anthryl group, and the other Ar 1 or Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted pyridazinyl group.

4. The organic light-emitting device of claim 1 , wherein R 1 to R 12 are hydrogen atoms, and one of Ar 1 or Ar 2 is a substituted or unsubstituted phenyl group, and the other Ar 1 or Ar 2 is a substituted or unsubstituted pyrimidinyl group.

5. The organic light-emitting device of claim 1 , wherein one or two of Ar 11 , Ar 12 , or Ar 13 are each independently an unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted fluoranthenyl group, and the others of Ar 11 , Ar 12 , or Ar 13 are each independently a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted bipyridinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, or a substituted or unsubstituted benzocarbazolyl group,

L 11 , L 12 , and L 13 are each independently an unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted fluoranthenylene group, and

a, b, and c are each independently an integer from 0 to 1.

6. The organic light-emitting device of claim 1 , wherein one or two of Ar 11 , Ar 12 , or Ar 13 are each independently an unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted anthryl group, and the others of Ar 11 , Ar 12 , or Ar 13 are each independently a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted isoquinolinyl group,

L 11 , L 12 , and L 13 are each independently an unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenylene group, or a substituted or unsubstituted anthrylene group, and

a, b, and c are each independently an integer from 0 to 1.

7. The organic light-emitting device of claim 1 , wherein one or two of Ar 11 , Ar 12 , or Ar 13 are each independently an unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthrenyl group, and the others of Ar 11 , Ar 12 , or Ar 13 are each independently a substituted or unsubstituted quinolinyl group or a substituted or unsubstituted isoquinolinyl group,

L 11 , L 12 , and L 13 are each independently an unsubstituted phenylene group, and

a, b, and c are each independently an integer from 0 to 1.

8. The organic light-emitting device of claim 1 , wherein R 1 to R 12 are hydrogen atoms,

one of Ar 1 or Ar 2 is a substituted or unsubstituted phenyl group, and the other of Ar 1 or Ar 2 is a substituted or unsubstituted pyrimidinyl group,

one or two of Ar 11 , Ar 12 , or Ar 13 are each independently an unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthrenyl group, and the others of Ar 11 , Ar 12 , or Ar 13 are each independently a substituted or unsubstituted quinolinyl group or a substituted or unsubstituted isoquinolinyl group,

L 11 , L 12 , and L 13 are each independently an unsubstituted phenylene group, and

a, b, and c are each independently an integer from 0 to 1.

9. The organic light-emitting device of claim 1 , wherein the compound represented by one of Formulae 1a to 1c comprises a compound selected from the group consisting of Compounds 1 to 6:

10. The organic light-emitting device of claim 1 , wherein the compound represented by Formula 2 comprises a compound selected from the group consisting of Compounds 11 to 16:

11. The organic light-emitting device of claim 1 , wherein the metal-containing compound comprises an alkali metallic element.

12. The organic light-emitting device of claim 1 , wherein the metal-containing compound comprises at least one selected from the group consisting of lithium quinolate (LiQ), lithium fluoride (LiF), and Compound 101:

13. The organic light-emitting device of claim 1 , wherein the metal-containing compound is present in an amount of about 20 to about 80 wt % based on the total weight of the electron transport layer.

14. The organic light-emitting device of claim 1 , wherein the phosphorescent emission layer is a red emission layer.

15. The organic light-emitting device of claim 1 , further comprising at least one layer between the first electrode and the phosphorescent emission layer, the at least one layer being selected from the group consisting of a hole injection layer, a hole transport layer, and a functional layer having both hole injecting and hole transporting capabilities.

16. The organic light-emitting device of claim 1 , further comprising a hole transport layer between the first electrode and the phosphorescent emission layer, wherein the hole transport layer comprises a compound represented by Formula 3:

wherein R 50 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted pyridyl group,

L 21 is a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, a substituted or unsubstituted C 6 -C 30 arylene group, or a substituted or unsubstituted C 2 -C 30 heteroarylene group,

R 51 to R 67 are each independently a hydrogen atom, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, 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 1 -C 30 alkylthiol group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, or —N(Q 11 )(Q 12 ),

wherein Q 11 and Q 12 are each independently a hydrogen atom, a deuterium, a halogen atom, a hydroxyl group, a cyano group, an amino group, a nitro group, a carboxyl group, a C 1 -C 30 alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, a C 1 -C 30 alkoxy group, C 1 -C 30 alkylthiol group, a C 3 -C 30 cycloalkyl group, a C 3 -C 30 cycloalkenyl group, a C 6 -C 30 aryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, or a C 2 -C 30 heteroaryl group, and

k is an integer from 0 to 3.

17. The organic light-emitting device of claim 16 , wherein the hole transport layer further comprises a charge-generating material, wherein the charge-generating material comprises at least one of a quinone derivative, a metal oxide, or a cyano group-containing compound.

18. The organic light-emitting device of claim 16 , further comprising a hole injection layer between the first electrode and the hole transport layer, wherein the hole injection layer comprises a compound represented by Formula 4:

wherein Ar 41 and Ar 42 are each independently a substituted or unsubstituted C 6 -C 30 arylene group or a substituted or unsubstituted C 2 -C 30 heteroarylene group, and

R 71 and R 72 are each independently a hydrogen atom, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 30 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, or a substituted or unsubstituted C 6 -C 30 aryloxy group, or a substituted or unsubstituted C 6 -C 30 arylthio group.

19. The organic light-emitting device of claim 1 , further comprising an electron injection layer between the second electrode and the electron transport layer.

20. An organic light-emitting display apparatus comprising the organic light-emitting device of claim 1 , and a transistor comprising a source, a drain, a gate, and an active layer,

wherein the first electrode of the organic light-emitting device is electrically connected to the source or the drain of the transistor.