IP Library › Granted Patent US 11,056,654
Granted Patent B2
US 11,056,654 · App. 14/533,606 · Granted Jul 6, 2021

Carbazole-based compound and organic light emitting device including the same

Inventors: Myeong-Suk Kim (Yongin, KR); Yoon-Hyun Kwak (Yongin, KR); Soung-Wook Kim (Yongin, KR); Jae-Hong Kim (Yongin, KR); Moon-Jae Lee (Yongin, KR)
Assignee: Samsung Display Co., Ltd.
H01L51/0072C09K11/06H01L51/0074H01L51/5096
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Quick Facts
Patent No.
US 11,056,654
App. No.
14/533,606
Granted
Jul 6, 2021
Kind
B2
Abstract

A carbazole-based compound and an organic light-emitting device including the carbazole-based compound, the compound being represented by one of the following Formulae 1 to 3:

Claims (121)

1. An organic light-emitting device, comprising:

a first electrode;

a second electrode;

an organic layer between the first electrode and the second electrode, the organic layer including an emission layer; and

an electron blocking layer between the first electrode and the emission layer, the electron blocking layer including a carbazole-based compound represented by one of the following Formulae 1 to 3:

wherein, in Formulae 1 to 3,

X is an oxygen atom or a sulfur atom;

Y 1 and Y 2 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, and a substituted or unsubstituted C 2 -C 30 heteroaryl group;

R 1 , R 2 , R 5 , R 6 , R 11 , and R 12 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxy group, a carboxyl group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 1 -C 60 alkylthio group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 3 -C 60 cycloalkylene group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arythio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, and —N(Q 1 )(Q 2 ),

R 3 , R 4 , R 7 , R 8 , R 9 , and R 10 are each independently selected from:

a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxy group, C 1 -C 20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a quinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isooxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —N(Q 1 )(Q 2 ); and

a C 1 -C 20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a quinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isooxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one of a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, and a C 1 -C 30 heteroaryl group,

Q 1 and Q 2 are each independently selected from a hydrogen atom, a deuterium atom, a C 1 -C 10 alkyl group, a C 6 -C 30 aryl group, and a C 2 -C 30 heteroaryl group; or Q 1 and Q 2 bind to each other to form a saturated ring or an unsaturated ring formed of nitrogen, Q 1 , and Q 2 ;

a1, a5, a8, a9, a11, and a12 are each independently integers of 0 to 4;

a2, a3, and a6 are each independently integers of 0 to 3;

a4 is an integer of 0 to 2; and

a7 and a10 are each independently integers of 0 or 1, provided that at least one of a3, a4, a7, a8, a9, or a10 is not 0, and at least one of R 3 ,R 4 , R 7 , R 8 , R 9 , or R 10 is a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxy group, C 1 -C 20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a quinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isooxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or —N(Q 1 )(Q 2 ); or

a C 1 -C 20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a quinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isooxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each substituted with at least one of a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkyl group, a C 1 -C 10 heterocycloalkenyl 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 1 -C 30 heteroaryl group.

2. The organic light-emitting device as claimed in claim 1 , wherein Y 1 and Y 2 are each independently selected from:

a hydrogen atom, a deuterium atom, a C 1 -C 20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, and a hexacenyl group; and

a C 1 -C 20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, and a hexacenyl group, each substituted with at least one of a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, and a C 1 -C 30 heteroaryl group.

3. The organic light-emitting device as claimed in claim 1 , wherein Y 1 and Y 2 are each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one of a deuterium, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, iso-propyl group, an n-butyl group, a sec-butyl group, iso-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and an anthryl group.

4. The organic light-emitting device as claimed in claim 1 , wherein Y 1 and Y 2 are each independently selected from:

a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, and a 4-fluorenyl group; and

a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, and a 4-fluorenyl group, each substituted with at least one of a deuterium, a methyl group, an ethyl group, a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.

5. The organic light-emitting device as claimed in claim 1 , wherein:

Y 1 and Y 2 are each independently represented by one of Formulae 4-1 to 4-4 below:

and

in Formulae 4-1 to 4-4, * is a binding site to an N of a carbazole ring.

6. The organic light-emitting device as claimed in claim 1 , wherein:

R 1 , R 2 , R 5 , R 6 , R 11 , and R 12 are each independently selected from:

a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a hydroxy group, C 1 -C 20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a quinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isooxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —N(Q 1 )(Q 2 ); and

a C 1 -C 20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a quinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isooxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one of a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, and a C 1 -C 30 heteroaryl group, and

Q 1 and Q 2 are each independently selected from a C 6 -C 30 aryl group and a C 1 -C 30 heteroaryl group.

7. The organic light-emitting device as claimed in claim 1 , wherein:

R 1 , R 2 , R 5 , R 6 , R 11 , and R 12 are each independently selected from:

a hydrogen atom, a deuterium atom, —F, a cyano group, a nitro group, a hydroxy group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptadienyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthryl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, a benzothiazolyl group, a triazolyl group, a tetrazolyl group, a triazinyl group, and —N(Q 1 )(Q 2 ); and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthryl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, a benzothiazolyl group, a triazolyl group, a tetrazolyl group, and a triazinyl group, each substituted with at least one of a deuterium, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, iso-propyl group, an n-butyl group, a sec-butyl group, iso-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and an anthryl group,

R 3 , R 4 , R 7 , R 8 , R 9 and R 10 are each independently selected from:

a hydrogen atom, a deuterium atom, —F, a cyano group, a nitro group, a hydroxy group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptadienyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthryl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a thiazolyl group, a benzothiazolyl group, a triazolyl group, a tetrazolyl group, a triazinyl group, and —N(Q 1 )(Q 2 ); and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthryl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a thiazolyl group, a benzothiazolyl group, a triazolyl group, a tetrazolyl group, and a triazinyl group, each substituted with at least one of a deuterium, —F, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, iso-propyl group, an n-butyl group, a sec-butyl group, iso-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and an anthryl group, and

Q 1 and Q 2 are each independently selected from a phenyl group, a naphthyl group, an anthryl group, and a fluorenyl group.

8. The organic light-emitting device as claimed in claim 1 , wherein: R 1 to R 12 are each independently selected from:

a hydrogen atom, a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, and —N(Q 1 )(Q 2 );

a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, and a 4-carbazolyl group, each substituted with at least one of a deuterium, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and an anthryl group, and

Q 1 and Q 2 are each independently selected from a phenyl group, and a naphthyl group.

9. The organic light-emitting device as claimed in claim 1 , wherein:

R 1 to R 12 are each independently represented by one of the following Formulae 5-1 to 5-8:

and

in Formulae 5-1 to 5-8, * is a binding site.

10. The organic light-emitting device as claimed in claim 1 , wherein:

the carbazole-based compound is represented by one of the following Formulae 1a to 1d, 2a to 2d, and 3:

in Formulae 1a to 1d, 2a to 2d, and 3:

X is an oxygen atom or a sulfur atom;

Y 1 and Y 2 are each independently selected from:

a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, and a 4-fluorenyl group; and

a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, and a 4-fluorenyl group, each substituted with at least one of a deuterium, a methyl group, an ethyl group, a phenyl group, a 1-naphthyl group, and a 2-naphthyl group;

R 1 to R 12 are each independently selected from:

a hydrogen atom, a deuterium atom, an —F, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group and —N(Q 1 )(Q 2 ); and

a phenyl group, a naphthyl group, a fluorenyl group, and a carbazolyl group, each substituted with at least one of a deuterium, an —F, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and an anthryl group; a1, a5, a8, a9, a11, and a12 are each independently integers of 0 to 4;

Q 1 and Q 2 are each independently selected from a phenyl group, and a naphthyl group;

a2, a3, and a6 are each independently integers of 0 to 3;

a4 is an integer of 0 to 2; and

a7 and a10 are each independently integers of 0 or 1.

11. The organic light-emitting device as claimed in claim 1 , wherein:

the carbazole-based compound is represented by one of the following Formulae 1a to 1d, 2a to 2d, and 3:

in Formulae 1a to 1d, 2a to 2d, and 3:

X is an oxygen atom or a sulfur atom;

Y 1 and Y 2 are each independently represented by one of the following Formulae 4-1 to 4-4:

in Formulae 4-1 to 4-4, * is a binding site to N of a carbazole;

R 1 to R 12 are each independently represented by one of Formulae 5-1 to 5-8:

in Formulae 5-1 to 5-8, * is a binding site;

a1, a5, a8, a9, a11, and a12 are each independently integers of 0 to 4;

a2, a3, and a6 are each independently integers of 0 to 3;

a4 is an integer of 0 to 2; and

a7 and a10 are each independently integers of 0 or 1.

12. The organic light-emitting device as claimed in claim 1 , wherein:

the carbazole-based compound is represented by one of the following Formulae 1e to 1h, 2e to 2h, and 3a:

in Formulae 1e to 1h, 2e to 2h, and 3a:

X is an oxygen atom or a sulfur atom;

Y 1 and Y 2 are each independently selected from:

a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, and a 4-fluorenyl group; and

a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, and a 4-fluorenyl group, each substituted with at least one of a deuterium, a methyl group, an ethyl group, a phenyl group, 1-naphthyl group and 2-naphthyl group;

R 1 , R 5 , R 7 , R 8 , R 10 , R 11 , R 12 , R 41 and R 42 are each independently selected from:

a hydrogen atom, a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, and —N(Q 1 )(Q 2 ), in which Q 1 and Q 2 are each independently a phenyl group or a naphthyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, and a carbazolyl group, each substituted with at least one of a deuterium, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and an anthryl group.

13. The organic light-emitting device as claimed in claim 1 , wherein:

the carbazole-based compound is represented by one of Formulae 1e to 1h, 2e to 2h, and 3a:

in Formulae 1e to 1h, 2e to 2h, and 3a:

X is an oxygen atom or a sulfur atom;

Y 1 and Y 2 are each independently represented by one of the following Formulae 4-1 to 4-4:

in Formulae 4-1 to 4-4, * is a binding site to N of a carbazole ring; and

R 1 , R 5 , R 7 , R 8 , R 11 , R 10 , R 12 , R 41 , and R 42 are each independently represented by one of the following Formulae 5-1 to 5-8:

and

in Formulae 5-1 to 5-8, * is a binding site.

14. The organic light-emitting device as claimed in claim 1 , wherein:

the carbazole-based compound is represented by one of the following Formulae 1i, 1j, 2i, and 3b:

in Formulae 1i, 1j, 2i, and 3b:

X is an oxygen atom or a sulfur atom;

Y 1 and Y 2 are each independently selected from:

a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, and a 4-fluorenyl group; and

a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, and a 4-fluorenyl group, each substituted with at least one of a deuterium, a methyl group, an ethyl group, a phenyl group, 1-naphthyl group and 2-naphthyl group;

R 1 , R 5 , R 7 , R 8 , R 10 , R 11 , R 12 , R 41 and R 42 are each independently selected from:

a hydrogen atom, a deuterium atom, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group and —N(Q 1 )(Q 2 ); and

a phenyl group, a naphthyl group, a fluorenyl group and a carbazolyl group, each substituted with at least one of a deuterium, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and an anthryl group, and

Q 1 and Q 2 are each independently selected from a phenyl group and a naphthyl group.

15. The organic light-emitting device as claimed in claim 1 , wherein:

the carbazole-based compound is represented by one of the following Formulae 1i, 1j, 2i, and 3b:

in Formulae 1i, 1j, 2i, and 3b:

X is an oxygen atom or a sulfur atom;

Y 1 and Y 2 are each independently represented by one of the following Formula 4-1 to 4-4:

in Formulae 4-1 to 4-4, * is a binding site to N of a carbazole ring;

R 1 , R 5 , R 7 , R 8 , R 10 , R 11 , R 12 , R 41 , and R 42 are each independently represented by one of Formulae 5-1 to 5-8:

and

in Formulae 5-1 to 5-8, * is a binding site.

16. The organic light-emitting device as claimed in claim 1 , wherein the carbazole-based compound is one of Compounds 1 to 9:

17. The organic light-emitting device as claimed in claim 1 , wherein the organic layer includes:

a hole-transporting region between the first electrode and the emission layer, the hole-transporting region including at least one of hole injection layer, a hole transport layer, a functional layer having both hole injecting and hole transporting capabilities, and a buffer layer, and

an electron transport region between the emission layer and the second electrode, the electron transport region including at least one of an electron transport layer and an electron injection layer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 5, 2014
From: KIM, MYEONG-SUK; KWAK, YOUN-HYUN; KIM, SOUNG-WOOK; KIM, JAE-HONG; LEE, MOON-JAE
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 034109/0285 →
Priority Claims (1)
KR 10-2014-050179 · Apr 25, 2014 · national
Continuity (1)
Related Publication 20150311451A1 · Oct 29, 2015