Indeno indene-based compound, organic light emitting device comprising the same, and method of manufacturing the organic light emitting device
Provided is an indeno indene-based compound represented by Formula 1: where R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are the same as in the detailed description. An organic light emitting device including the indeno indene-based compound has low driving voltage, high efficiency, and high color purity.
1 . An indeno indene-based compound represented by Formula 1:
where R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently, hydrogen, a substituted or unsubstituted C 1 -C 40 alkyl group, a substituted or unsubstituted C 1 -C 40 alkoxy group, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted C 5 -C 40 cycloalkyl group, a substituted or unsubstituted C 5 -C 40 hetero cycloalkyl group, —N(Q 1 )(Q 2 ) or —Si(Q 3 )(Q 4 )(Q 5 ) where Q 1 , Q 2 , Q 3 , Q 4 and Q 5 are each independently, hydrogen, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted C 5 -C 40 cycloalkyl group or a substituted or unsubstituted C 5 -C 40 hetero cycloalkyl group.
2 . The indeno indene-based compound of claim 1 , wherein the substituted C 1 -C 40 alkyl group, the substituted C 1 -C 40 alkoxy group, the substituted C 6 -C 50 aryl group, the substituted C 2 -C 50 heteroaryl group, the substituted C 5 -C 40 cycloalkyl group, and the substituted C 5 -C 40 hetero cycloalkyl group have at least one substituent independently selected from the group consisting of —F, —Cl, —Br, —CN, —NO 2 , —OH, a C 1 -C 50 alkyl group that is unsubstituted or substituted with —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 1 -C 50 alkoxy group that is unsubstituted or substituted with —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 6 -C 50 aryl group that is unsubstituted or substituted with a C 1 -C 50 alkyl group, a C 1 -C 50 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 2 -C 50 heteroaryl group that is unsubstituted or substituted with a C 1 -C 50 alkyl group, a C 1 -C 50 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 5 -C 50 cycloalkyl group that is unsubstituted or substituted with a C 1 -C 50 alkyl group, a C 1 -C 50 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 5 -C 50 heterocycloalkyl group that is unsubstituted or substituted with a C 1 -C 50 alkyl group, a C 1 -C 50 alkoxy group, —F, —Cl, —Br, —CN, —NO 2 or —OH; and a group represented by —N(Q 11 )(Q 12 ) where Q 11 and Q 12 are each independently hydrogen, a C 1 -C 50 alkyl group, or a C 6 -C 50 aryl group substituted with a C 1 -C 50 alkyl group.
3 . The indeno indene-based compound of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently hydrogen, a C 1 -C 40 alkyl group, a C 1 -C 40 alkoxy group, a phenyl group, a biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a biphenylenyl group, an anthracenyl group, an azurenyl 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 fluorenyl 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 imidazolinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a di(C 6 -C 50 aryl)amino group, a tri(C 6 -C50aryl)silyl group, or derivatives thereof.
4 . The indeno indene-based compound of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently selected from the group consisting of aryl groups having the following structures:
where R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 are each independently, hydrogen, a substituted or unsubstituted C 1 -C 40 alkyl group, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted C 5 -C 40 cycloalkyl group or a substituted or unsubstituted C 5 -C 40 hetero cycloalkyl group; and
an asterisk (*) indicates a binding site.
5 . The indeno indene-based compound of claim 1 , wherein at least one of R 1 and R 2 and at least one of R 3 and R 4 are each independently selected from the group consisting of a methyl group and functional groups represented by Formulae iii, x, xviii and xxii:
6 . The indeno indene-based compound of claim 1 , wherein the compound represented by Formula 1 is selected from the group consisting of compounds represented by Formulae Formula 2 through 7:
7 . An organic light emitting device comprising an organic layer comprised of the indeno indene-based compound of claim 1 .
8 . An organic light emitting device comprising:
a first electrode;
a second electrode; and
at least one organic layer between the first electrode and the second electrode,said at least one organic layer comprising an organic layer comprised of an indeno indene-based compound represented by Formula 1:
where R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently, hydrogen, a substituted or unsubstituted C 1 -C 40 alkyl group, a substituted or unsubstituted C 1 -C 40 alkoxy group, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted C 5 -C 40 cycloalkyl group, a substituted or unsubstituted C 5 -C 40 hetero cycloalkyl group, —N(Q 1 )(Q 2 ) or —Si(Q 3 )(Q 4 )(Q 5 ) where Q 1 , Q 2 , Q 3 , Q 4 and Q 5 are each independently, hydrogen, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted C 5 -C 40 cycloalkyl group or a substituted or unsubstituted C 5 -C 40 hetero cycloalkyl group.
9 . The organic light emitting device of claim 8 , wherein the organic layer comprised of the indeno indene-based compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, an emission layer, a hole blocking layer, an electron transport layer and an electron injection layer.
10 . The organic light emitting device of claim 8 , further comprising: between the first electrode and the second electrode, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
11 . The organic light emitting device of claim 8 , wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently hydrogen, a C 1 -C 40 alkyl group, a C 1 -C 40 alkoxy group, a phenyl group, a biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a biphenylenyl group, an anthracenyl group, an azurenyl 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 fluorenyl 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 imidazolinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a di(C 6 -C 50 aryl)amino group, a tri(C 6 -C 50 aryl)silyl group, or derivatives thereof.
12 . The organic light emitting device of claim 8 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is selected from the group consisting of aryl groups having the following structures:
where R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 are each independently, hydrogen, a substituted or unsubstituted C 1 -C 40 alkyl group, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted C 5 -C 40 cycloalkyl group or a substituted or unsubstituted C 5 -C 40 hetero cycloalkyl group.
13 . The organic light emitting device of claim 8 , wherein at least one of R 1 and R 2 , and at least one of R 3 and R 4 are each independently selected from the group consisting of a methyl group and functional groups represented by Formulae iii, x, xviii and xxii:
14 . The organic light emitting device of claim 8 , wherein the compound represented by Formula 1 is selected from the group consisting of compounds represented by Formulae Formula 2 through 4:
15 . The organic light emitting device of claim 8 , wherein the compound represented by Formula 1 is selected from the group consisting of compounds represented by Formulae Formula 5 through 7:
16 . A method of manufacturing an organic light emitting device, the method comprising:
forming a first electrode on a substrate;
forming at least one organic layer comprising an organic layer comprised of an indeno indene-based compound on the first electrode, the indeno indene-based compound represented by Formula 1:
where R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently, hydrogen, a substituted or unsubstituted C 1 -C 40 alkyl group, a substituted or unsubstituted C 1 -C 40 alkoxy group, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted C 5 -C 40 cycloalkyl group, a substituted or unsubstituted C 5 -C 40 hetero cycloalkyl group, —N(Q 1 )(Q 2 ) or —Si(Q 3 )(Q 4 )(Q 5 ) where Q 1 , Q 2 , Q 3 , Q 4 and Q 5 are each independently, hydrogen, a substituted or unsubstituted C 6 -C 50 aryl group, a substituted or unsubstituted C 2 -C 50 heteroaryl group, a substituted or unsubstituted C 5 -C 40 cycloalkyl group or a substituted or unsubstituted C 5 -C 40 hetero cycloalkyl group; and
forming a second electrode on the at least one organic layer.
17 . The method of claim 16 , wherein the organic layer comprised of the indeno indene-based compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an emission layer.
18 . The method of claim 16 , wherein the organic layer comprised of the indeno indene-based compound is formed using any one method selected from the group consisting of a deposition method, a spin coating method, a casting method, an inkjet printing method, and a microcontact printing method.
19 . The method of claim 16 , wherein the formation of said at least one organic layer comprises at least one process selected from the group consisting of a hole injection layer forming process, a hole transport layer forming process, an electron blocking layer forming process, a hole blocking layer forming process, an electron transport layer forming process, and an electron injection layer forming process.
20 . The organic light emitting device manufactured by the method of claim 16 .