Organosiloxane compound and organic light-emitting device comprising the same

1. An organosiloxane compound represented by Formula 1:

where L 1 , L 2 , L 3 , and L 4 are each independently a substituted or unsubstituted C 6 -C 30 arylene group, or a substituted or unsubstituted C 2 -C 30 heteroarylene group;

M 1 and M 2 are each independently

L 5 , L 6 , and L 7 are each independently a substituted or unsubstituted C 6 -C 30 aryl group, or a substituted or unsubstituted C 2 -C 30 heteroaryl group, and L 5 and L 6 are optionally connected to form a substituted or unsubstituted ring having the N atom;

A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 are each independently hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, or a substituted or unsubstituted C 6 -C 30 aryl group;

B 1 , B 2 , B 3 , and B 4 are each independently hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl group, or a substituted or unsubstituted C 6 -C 30 aryl group;

n is an integer of 0 through 5;

l is an integer of 1; and

m is an integer of 0 through 3.

2. The organosiloxane compound of claim 1 , wherein L 1 , L 2 , L 3 , and L 4 are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazoylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted thiazolylene group;

M 1 and M 2 are each independently

L 5 , L 6 , and L 7 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group; and

L 5 , and L 6 can be connected to form a substituted or unsubstituted ring containing the N atom.

3. The organosiloxane compound of claim 1 , wherein a substituent of the alkyl group, the aryl group, the heteroaryl group, and the cycloalkyl group comprises at least one material selected from the group consisting of —F; —Cl; —Br; —CN; —NO 2 ; —OH; an unsubstituted C 1 -C 20 alkyl group; 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; 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; a C 6 -C 30 aryl group substituted with —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 2 -C 30 heteroaryl group; a C 2 -C 30 heteroaryl group substituted with —F, —Cl, —Br, —CN, —NO 2 , or —OH; an unsubstituted C 5 -C 20 cycloalkyl group; and a C 5 -C 20 cycloalkyl group substituted with —F, —Cl, —Br, —CN, —NO 2 , or —OH.

4. The organosiloxane compound of claim 1 , wherein L 1 , L 2 , L 3 , and L 4 are each independently a phenylene group, a (C 1 -C 10 alkyl)phenylene group, a (C 1 -C 10 alkoxy)phenylene group, a halophenylene group, a cyanophenylene group, a dicyanophenylene group, a trifluoromethoxyphenylene group, an o-, m-, or p-tolylene group, an o-, m-, or p-cumenylene group, a mesitylene group, a phenoxyphenylene group, an (α,α-dimethylbenzene)phenylene group, a (N,N′-dimethyl)aminophenylene group, a (N,N′-diphenyl)aminophenylene group, a ((C 1 -C 10 alkyl)cyclohexyl)phenylene group, an (anthracenyl)phenylene group, a biphenylene group, a (C 1 -C 10 alkyl)biphenylene group, a (C 1 -C 10 alkoxy)biphenylene group, a pentalenyl group, an indenylene group, a naphthylene group, a (C 1 -C 10 alkyl naphthylene group, a (C 1 -C 10 alkoxy)naphthylene group, a halonaphthylene group, a cyanonaphthylene group, a biphenylenylene group, a (C 1 -C 10 alkyl)biphenylene group, a (C 1 -C 10 alkoxy)biphenylene group, an anthracenylene group, an azulenylene group, a heptarenylene group, an acenaphthylenylene group, a phenalenylene group, a fluorenylene group, an anthraquinolylene group, a methylanthrylene group, a phenanthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, an ethyl-chrysenylene group, a picenylene group, a perylenylene group, a chloroperylenylene group, a pentaphenylene group, a pentacenylene group, a tetraphenylenylene group, a hexaphenylene group, a hexacenylene group, a rubicenylene group, a coronenylene group, a trinaphthylenylene group, a heptaphenylene group, a heptacenylene group, a pyranthrenylene group, an ovalenylene group, a carbazolylene group, a (C 1 -C 10 alkyl)carbazolylene group, a thio phenylene group, an indolylene group, a purinylene group, a benzimidazolylene group, a quinolinylene group, a benzothiophenylene group, a parathiazinylene group, a pyrrolylene group, a pyrazolylene group, an imidazolylene group, an imidazolinylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a pyridinylene group, a pyridazinylene group, a pyrimidinylene group, a pyrazinylene group, a thianthrenylene group, a pyrrolidinylene group, a pyrazolidinylene group, an imidazolidinylene group, a piperidinylene group, a piperazinylene group, or a morpholynylene group.

5. The organosiloxane compound of claim 1 , wherein L 5 , L 6 , and L 7 are each independently a phenyl group, a (C 1 -C 10 alkyl)phenyl group, a (C 1 -C 10 alkoxy)phenyl group, a halophenyl group, a cyanophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, or p-tolyl group, an o-, m-, or p-cumenyl group, a mesityl group, a phenoxyphenyl group, an (α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, a ((C 1 -C 10 alkyl)cyclohexyl)phenyl group, an (anthracenyl)phenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a (C 1 -C 10 alkyl)naphthyl group, a (C 1 -C 10 alkoxy)naphthyl group, a halonaphthyl group, a cyanonaphthyl group, a biphenylenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, an anthracenyl group, an azulenyl group, a heptarenyl group, an acenaphthylenyl group, a phenalenyl group, a fluorenyl group, an anthraquinolyl 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 (C 1-10 alkyl)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 pyrrolidinyl group, a pyrazolidinyl group, an imidazolidinyl group, a piperidinyl group, a piperazinyl group, a carbazoryl group, a bezoxazolyl group, a phenothiazinyl group, a 5H-dibenzazepinyl group, a 5H-tribenzazepinyl group, or a morpholynyl group.

6. The organosiloxane compound of claim 1 , wherein A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 are each independently hydrogen, methyl, ethyl, propyl, butyl, methoxy, ethoxy, a propoxy group, a butoxy group, a phenyl group, a (C 1 -C 10 alkyl)phenyl group, a (C 1 -C 10 alkoxy)phenyl group, a halophenyl group, a cyanophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, or p-tolyl group, an o-, m- or p-cumenyl group, a mesityl group, a phenoxyphenyl group, an (α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, a ((C 1 -C 10 alkyl)cyclohexyl)phenyl group, an (anthracenyl)phenyl group, a biphenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a (C 1 -C 10 alkyl)naphthyl group, a (C 1 -C 10 alkoxy)naphthyl group, a halonaphthyl group, a cyanonaphthyl group, a biphenylenyl group, a (C 1 -C 10 alkyl)biphenyl, a (C 1 -C 10 alkoxy)biphenyl group, an anthracenyl group, an azulenyl group, a heptarenyl group, an acenaphthylenyl group, a phenalenyl group, a fluorenyl group, an anthraquinolyl 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, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, an ovalenyl group, a carbazolyl group, a cyclopentyl group, a cyclohexyl group, a (C 1 -C 10 alkyl)cyclohexyl group, or a (C 1 -C 10 alkoxy)cyclohexyl group.

7. The organosiloxane compound of claim 1 , wherein B 1 , B 2 , B 3 , and B 4 are each independently hydrogen, methyl, ethyl, propyl, butyl, a phenyl group, a (C 1 -C 10 alkyl)phenyl group, a (C 1 -C 10 alkoxy)phenyl group, a halophenyl group, a cyanophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, or p-tolyl group, an o-, m-, or p-cumenyl group, a mesityl group, a phenoxyphenyl group, an (α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, a ((C 1 -C 10 alkyl)cyclohexyl)phenyl group, an (anthracenyl)phenyl group, biphenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a (C 1 -C 10 alkyl)naphthyl group, a (C 1 -C 10 alkoxy)naphthyl group, a halonaphthyl group, a cyanonaphthyl group, a biphenylenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, an anthracenyl group, an azulenyl group, a heptarenyl group, an acenaphthylenyl group, a phenalenyl group, a fluorenyl group, an anthraquinolyl 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 cyclopentyl group, a cyclohexyl group, a (C 1 -C 10 alkyl)cyclohexyl group, or a (C 1 -C 10 alkoxy)cyclohexyl group.

8. The organosiloxane compound of claim 1 , being represented by one of the following Formulae:

9. The organosiloxane compound of claim 1 , wherein L 1 , L 2 , L 3 , and L 4 are each independently a phenylene group, a (C 1 -C 10 alkyl)phenylene group, a (C 1 -C 10 alkoxy)phenylene group, a halophenylene group, a cyanophenylene group, a dicyanophenylene group, a trifluoromethoxyphenylene group, an o-, m-, or p-tolylene group, an o-, m-, or p-cumenylene group, a mesitylene group, a phenoxyphenylene group, an (α,α-dimethylbenzene)phenylene group, a (N,N′-dimethyl)aminophenylene group, a (N,N′diphenyl)aminophenylene group, a ((C 1 -C 10 alkyl)cyclohexyl)phenylene group, an (anthracenyl)phenylene group, a biphenylene group, a (C 1 -C 10 alkyl)biphenylene group, a (C 1 -C 10 alkoxy)biphenylene group, a pentalenyl group, an indenylene group, a naphthylene group, a (C 1 -C 10 alkyl)naphthylene group, a (C 1 -C 10 alkoxy)naphthylene group, a halonaphthylene group, a cyanonaphthylene group, a biphenylenylene group, a (C 1 -C 10 alkyl)biphenylene group, a (C 1 -C 10 alkoxy)biphenylene group, an anthracenylene group, an azulenyl group, a hepatarenylene group, an acenaphthylenylene group, a phenalenylene group, a fluorenylene group, an anthraquinolylene group, a methylanthrylene group, a phenanthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, an ethyl-chrysenylene group, a picenylene group, a perylenylene group, a chloroperylenylene group, a pentaphenylene group, a pentacenylene group, a tetraphenylene group, a hexaphenylene group, a hexacenylene group, a rubicenylene group, a coronenylene group, a trinaphthylenylene group, a heptaphenylene group, a heptacenylene group, a pyranthrenylene group, an ovalenylene group, a carbazolylene group, a (C 1 -C 10 alkyl)carbazolylene group, a thio phenylene group, an indolylene group, a purinylene group, a benzimidazolylene group, a quinolinylene group, a benzothiophenylene group, a parathiazinylene group, a pyrrolylene group, a pyrazolylene group, an imidazolylene group, an imidazolinylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a pyridinylene group, a pyridazinylene group, a pyrimidinylene group, a pyrazinylene group, a thianthrenylene group, a pyrrolidinylene group, a pyrazolidinylene group, an imidazolidinylene group, a piperidinylene group, a piperazinylene group, or a morpholynylene group;

L 5 , L 6 , and L 7 are each independently a phenyl group, a (C 1 -C 10 alkyl)phenyl group, a (C 1 -C 10 alkoxy)phenyl group, a halophenyl group, a cyanophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, or p-tolyl group, an o-, m-, or p-cumenyl group, a mesityl group, a phenoxyphenyl group, a (N,N′-diphenyl)aminophenyl group, a ((C 1 -C 10 alkyl)cyclohexyl)phenyl group, an (anthracenyl)phenyl group, a biphenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a (C 1 -C 10 alkyl)naphthyl group, a (C 1 -C 10 alkoxy)naphthyl group, a halonaphthyl group, a cyanonaphthyl group, a biphenylenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, an anthracenyl group, an azulenyl group, a heptarenyl group, an acenaphthylenyl group, a phenalenyl group, a fluorenyl group, an anthraquinolyl 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 (C 1-10 alkyl)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 pyrrolidinyl group, a pyrazolidinyl group, an imidazolidinyl group, a piperidinyl group, a piperazinyl group, a carbazoryl group, a bezoxazolyl group, a phenothiazinyl group, a 5H-dibenzazepinyl group, a 5H-tribenzazepinyl group, or a morpholynyl group;

A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 are each independently hydrogen, methyl, ethyl, propyl, butyl, methoxy, ethoxy, a propoxy group, a butoxy group, a phenyl group, a (C 1 -C 10 alkyl)phenyl group, a (C 1 -C 10 alkoxy)phenyl group, a halophenyl group, a cyanophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, or p-tolyl group, an o-, m- or p-cumenyl group, a mesityl group, a phenoxyphenyl group, an (α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, a ((C 1 -C 10 alkyl)cyclohexyl)phenyl group, an (anthracenyl)phenyl group, a biphenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a (C 1 -C 10 alkyl)naphthyl group, a (C 1 -C 10 alkoxy)naphthyl group, a halonaphthyl group, a cyanonaphthyl group, a biphenylenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, an anthracenyl group, an azulenyl group, a heptarenyl group, an acenaphthylenyl group, a phenalenyl group, a fluorenyl group, an anthraquinolyl 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, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, an ovalenyl group, a carbazolyl group, a cyclopentyl group, a cyclohexyl group, a (C 1 -C 10 alkyl)cyclohexyl group, or a (C 1 -C 10 alkoxy)cyclohexyl group; and

B 1 , B 2 , B 3 , and B 4 are each independently hydrogen, methyl, ethyl, propyl, butyl, a phenyl group, a (C 1 -C 10 alkyl)phenyl group, a (C 1 -C 10 alkoxy)phenyl group, a halophenyl group, a cyanophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, or p-tolyl group, an o-, m-, or p-cumenyl group, a mesityl group, a phenoxyphenyl group, an (α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, a ((C 1 -C 10 alkyl)cyclohexyl)phenyl group, an (anthracenyl)phenyl group, biphenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a (C 1 -C 10 alkyl)naphthyl group, a (C 1 -C 10 alkoxy)naphthyl group, a halonaphthyl group, a cyanonaphthyl group, a biphenylenyl group, a (C 1 -C 10 alkyl)biphenyl group, a (C 1 -C 10 alkoxy)biphenyl group, an anthracenyl group, an azulenyl group, a heptarenyl group, an acenaphthylenyl group, a phenalenyl group, a fluorenyl group, an anthraquinolyl 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 cyclopentyl group, a cyclohexyl group, a (C 1 -C 10 alkyl)cyclohexyl group, or a (C 1 -C 10 alkoxy)cyclohexyl group.

10. An organic light-emitting device having the compound of claim 1 .

11. The organosiloxane compound of claim 1 , wherein M 1 and M 2 are each independently L 7 .