Organic light-emitting compound and organic light-emitting device containing the same
View Patent ↗Provided are an organic light-emitting compound of Formula 1 and an organic light-emitting device using the organic light-emitting compound: where Ar, R 1 , R 2 , R 3 , R 4 , and R 5 are the same as defined in the detailed description. The organic light-emitting device manufactured using the organic light-emitting compound has a low turn-on voltage and high efficiency and color purity.
1. An organic light-emitting device comprising an organic layer containing an organic light-emitting compound represented by Formula 1:
where Ar is a substituted or unsubstituted C 10 -C 30 aryl group;
R 1 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a nitro group, a hydroxyl group, an unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
each of R 3 , R 4 , and R 5 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
R 2 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group with the proviso that a substituent of the substituted C6-C50 aryl group is not an amino group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, and R 2 is not an anthracene group; and
X is selected from the group consisting of C(Z 6 )(Z 7 ), N(Z 8 ), O, S, SO 2 , Se, and SeO 2 wherein each of Z 6 and Z 7 is independently a substituted or unsubstituted C 1 -C 20 alkyl group, and Z 8 is independently hydrogen, or a substituted or unsubstituted C 1 -C 20 alkyl group.
2. The organic light-emitting device of claim 1 , being a compound represented by Formula 2:
where R 1 is selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, an unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, —N(Z 2 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
each of R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
R 2 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group with the proviso that a substituent of the substituted C 6 -C 30 aryl group is not an amino group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, and R 2 is not an anthracene group; and
X is selected from the group consisting of C(Z 6 )(Z 7 ), N(Z 8 ), O, S, SO 2 , Se, and SeO 2 wherein each of Z 6 and Z 7 is independently a substituted or unsubstituted C 1 -C 20 alkyl group, and Z 8 is independently hydrogen, or a substituted or unsubstituted C 1 -C 20 alkyl group.
3. The organic light-emitting device of claim 1 , being a compound represented by Formula 3:
where R 1 is selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, an unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
each of R 3 , R 4 , R 5 , R 6 , and R 7 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
R 2 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group with the proviso that a substituent of the substituted C 6 -C 30 aryl group is not an amino group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, and R 2 is not an anthracene group; and
X is selected from the group consisting of C(Z 6 )(Z 7 ), N(Z 8 ), O, S, SO 2 , Se, and SeO 2 wherein each of Z 6 and Z 7 is independently a substituted or unsubstituted C 1 -C 20 alkyl group, and Z 8 is independently hydrogen, or a substituted or unsubstituted C 1 -C 20 alkyl group.
4. The organic light-emitting device of claim 1 , wherein each of the substituted alkyl group, the substituted alkoxy group, the substituted aryl group, the substituted heteroaryl group, the substituted cycloalkyl group, and the substituted heterocycloalkyl group has at least one substituent selected from the group consisting of —F; —Cl; —Br; —CN; —NO 2 ; —OH; an unsubstituted C 1 -C 20 alkyl group or a C 1 -C 20 alkyl group substituted with —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 1 -C 20 alkoxy group or a C 1 -C 20 alkoxy group substituted with —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 6 -C 30 aryl group or a C 6 -C 30 aryl group substituted with a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 2 -C 30 heteroaryl group or a C 2 -C 30 heteroaryl group substituted with a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 5 -C 20 cycloalkyl group or a C 5 -C 20 cycloalkyl group substituted with a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 5 -C 30 heterocycloalkyl group or a C 5 -C 30 heterocycloalkyl group substituted with a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 , or —OH; and —N(Z 9 )(Z 10 ), wherein each of Z 9 and Z 10 is independently selected from the group consisting of hydrogen, a C 1 -C 10 alkyl group; and a C 6 -C 30 aryl group substituted with a C 1 -C 10 alkyl group.
5. The organic light-emitting device of claim 1 , wherein each of R 2 , R 3 , R 4 , and R 5 is independently selected from the group consisting of hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a biphenylenyl group, an anthracenyl group, an azulenyl group, a heptalenyl group, an acenaphthylenyl group, a phenalenyl group, a fluorenyl group, a methylanthryl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, an ovalenyl group, a carbazolyl group, a thiophenyl group, an indolyl group, a purinyl group, a benzimidazolyl group, a quinolinyl group, a benzothiophenyl group, a parathiazinyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, an imidazolinyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thianthrenyl group, a cyclopentyl group, a cyclohexyl group, an oxiranyl group, a pyrrolidinyl group, a pyrazolidinyl group, an imidazolidinyl group, a piperidinyl group, a pyrazinyl group, a morpholinyl group, a di(C 6 -C 30 aryl)amino group, a tri(C 6 -C 30 aryl)silyl group, and a derivative thereof.
6. The organic light-emitting device of claim 1 , wherein each of R 2 , R 3 , R 4 , and R 5 is independently selected from the group consisting of a methyl group, a methoxy group, a phenyl group, a tolyl group, a naphthyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, an imidazolinyl group, an indolyl group, a quinolinyl group, a diphenylamino group, a 2,3-di-p-tolylaminophenyl group, a triphenylsilyl group, and a derivative thereof.
7. The organic light-emitting compound of claim 1 , where X is one of N—CH 3 , O, and S.
8. The organic light-emitting device of claim 1 , wherein the organic light-emitting compound is one of compounds represented by the following Formulas:
9. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
at least one organic layer interposed between the first electrode and the second electrode, said at least one organic, layer containing a compound represented by Formula 1:
where Ar is a substituted or unsubstituted C 6 -C 30 aryl group;
R 1 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a nitro group, a hydroxyl group, an unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
each of R 3 , R 4 , and R 5 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
R 2 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group with the proviso that a substituent of the substituted C 6 -C 50 aryl group is not an amino group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, and R 2 is not an anthracene group; and
X is selected from the group consisting of C(Z 6 )(Z 7 ), N(Z 8 ), O, S, SO 2 , Se, and SeO 2 wherein each of Z 6 , Z 7 , and Z 8 is independently hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group.
10. The organic light-emitting device of claim 9 , wherein the compound is represented by Formula 2:
where R 1 is selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, an unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
each of R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is independently group hydrogen, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
R 2 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group with the proviso that a substituent of the substituted C 6 -C 30 aryl group is not an amino group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, and R 2 is not an anthracene group; and
X is selected from the group consisting of C(Z 6 )(Z 7 ), N(Z 8 ), O, S, SO 2 , Se, and SeO 2 wherein each of Z 6 , Z 7 , and Z 8 is independently hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group.
11. The organic light-emitting device of claim 9 , wherein the compound is represented by Formula 3:
where R 1 is selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, an unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
each of R 3 , R 4 , R 5 , R 6 , and R 7 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group;
R 2 is independently selected from the group consisting of hydrogen, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 50 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group with the proviso that a substituent of the substituted C 6 -C 30 aryl group is not an amino group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Z 1 )(Z 2 ), and —Si(Z 3 )(Z 4 )(Z 5 ), wherein each of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group, and R 2 is not an anthracene group; and
X is selected from the group consisting of C(Z 6 )(Z 7 ), N(Z 8 ), O, S, SO 2 , Se, and SeO 2 wherein each of Z 6 , Z 7 , and Z 8 is independently hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group.
12. The organic light-emitting device of claim 9 , wherein each of the substituted alkyl group, the substituted alkoxy group, the substituted aryl group, the substituted heteroaryl group, the substituted cycloalkyl group, and the substituted heterocycloalkyl group has at least one substituent selected from the group consisting of —F; —Cl; —Br; —CN; —NO 2 ; —OH; an unsubstituted C 1 -C 20 alkyl group or a C 1 -C 20 alkyl group substituted with —F, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 1 -C 20 alkoxy group or a C 1 -C 20 alkoxy group substituted with —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 6 -C 30 aryl group or a C 6 -C 30 aryl group substituted with a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 2 -C 30 heteroaryl group or a C 2 -C 30 heteroaryl group substituted with a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 5 -C 20 cycloalkyl group or a C 5 -C 20 cycloalkyl group substituted with a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 5 -C 30 heterocycloalkyl group or a C 5 -C 30 heterocycloalkyl group substituted with a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 , or —OH; and —N(Z 9 )(Z 10 ), wherein each of Z 9 and Z 10 is independently selected from the group consisting of hydrogen, a C 1 -C 20 alkyl group; and a C 6 -C 30 aryl group substituted with a C 1 -C 20 alkyl group.
13. The organic light-emitting device of claim 9 , wherein each of R 2 , R 3 , R 4 , and R 5 is independently selected from the group consisting of hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a biphenylenyl group, an anthracenyl group, an azulenyl group, a heptalenyl group, an acenaphthylenyl group, a phenalenyl group, a fluorenyl group, a methylanthryl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, an ovalenyl group, a carbazolyl group, a thiophenyl group, an indolyl group, a purinyl group, a benzimidazolyl group, a quinolinyl group, a benzothiophenyl group, a parathiazinyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, an imidazolinyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thianthrenyl group, a cyclopentyl group, a cyclohexyl group, an oxiranyl group, a pyrrolidinyl group, a pyrazolidinyl group, an imidazolidinyl group, a piperidinyl group, a pyrazinyl group, a morpholinyl group, a di(C 6 -C 30 aryl) amino group, a tri(C 6 -C 30 aryl)silyl group, and a derivative thereof.
14. The organic light-emitting device of claim 9 , wherein said at least one organic layer containing the compound represented by Formula 1 is at least one of an emitting layer, a hole injecting layer, and a hole transporting layer.
15. The organic light-emitting device of claim 9 , wherein the compound represented by Formula 1 is a host material of said at least one organic layer.
16. The organic light-emitting device of claim 9 , wherein the compound represented by Formula 1 is a dopant material of said at least one organic layer.
17. The organic light-emitting device of claim 9 , further comprising at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer.
18. The organic light-emitting device of claim 17 , having a structure including a first electrode, a hole injecting layer, an emitting layer, an electron transporting layer, an electron injecting layer, and a second electrode which are sequentially stacked, a structure including a first electrode, a hole injecting layer, a hole transporting layer, an emitting layer, an electron transporting layer, an electron injecting layer, and a second electrode which are sequentially stacked, or a structure including a first electrode, a hole injecting layer, a hole transporting layer, an emitting layer, a hole blocking layer, an electron transporting layer, an electron injecting layer, and a second electrode which are sequentially stacked.
19. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
at least one organic layer interposed between the first electrode and the second electrode, said at least one organic layer containing the compound represented by Formula 2 or 3:
where R 1 is selected from the group consisting of a methoxy group, a phenyl group, a tolyl group, a naphthyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, an indolyl group, a quinolinyl group, a diphenylamino group, a 2,3-di-p-tolylaminophenyl group, a triphenylsilyl group, and a derivative thereof;
each of R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is independently selected from the group consisting of a methyl group, a methoxy group, a phenyl group, a tolyl group, a naphthyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, an imidazolinyl group, an indolyl group, a quinolinyl group, a diphenylamino group, a 2,3-di-p-tolylaminophenyl group, a triphenylsilyl group, and a derivative thereof; and
X is one of N—CH 3 , O, and S.