IP Library › Granted Patent US 10,361,377
Granted Patent B2
US 10,361,377 · App. 15/102,912 · Granted Jul 23, 2019

Condensed cyclic compound and organic light emitting device including the same

Inventors: Hyung-Sun Kim (Suwon-si, KR); Byung-Ku Kim (Suwon-si, KR); Young-Kwon Kim (Suwon-si, KR); Chang-Woo Kim (Suwon-si, KR); Joo-Hee Seo (Suwon-si, KR); Chang-Ju Shin (Suwon-si, KR); Seung-Jae Lee (Suwon-si, KR); Kyu Young Hwang (Suwon-si, KR)
Assignee: Samsung SDI Co., Ltd.
H01L51/0071C07D519/00C07D519/02C09K11/025C09K11/06H01L51/006H01L51/0052H01L51/0061H01L51/0072H01L51/0081C09K2211/185H01L51/0085H01L51/5016H01L51/5024H01L51/5056H01L51/5072H01L51/5088H01L51/5092H01L51/5096H01L2251/5384
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Quick Facts
Patent No.
US 10,361,377
App. No.
15/102,912
Granted
Jul 23, 2019
Kind
B2
Abstract

A novel condensed cyclic compound and an organic light emitting device including the same are disclosed.

Claims (81)

1. A condensed cyclic compound represented by the following Formula 1:

wherein, in the Formulae,

in the Formula 1, the ring A 11 is represented by the Formula 1A;

in the Formula 1, the ring A 12 is represented by the Formula 1B;

X 11 is N-[(L 11 ) a11 -(R 11 ) b11 ], S, O, S(═O), S(═O) 2 , C(═O), C(R 13 )(R 14 ), Si(R 13 )(R 14 ), P(R 13 ), P(═O)R 13 or C═N(R 13 );

X 12 is N-[(L 12 ) a12 -(R 12 ) b12 ], S, O, S(═O), S(═O) 2 , C(═O), C(R 15 )(R 16 ), Si(R 15 )(R 16 ), P(R 15 ), P(═O)R 15 or C═N(R 15 );

X 1 is N—[(L 1 ) a1 -(R 1 ) b1 ], S, O, S(═O), S(═O) 2 , C(═O), Si(R 5 )(R 6 ), P(R 5 ), P(═O)R 5 or C═N(R 5 );

L 1 to L 4 , L 11 and L 12 are independently a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 2 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group;

a1 to a4, a11 and a12 are independently selected from integers of 0 to 3;

R 1 to R 6 , R 11 to R 16 and R 21 to R 30 are independently one of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, 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 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 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), or one of the groups represented by the Formula 2A to Formula 2F, provided that the R 1 to R 6 are not one of the groups represented by the Formula 2A, Formula 2B, Formula 2C, Formula 2D, Formula 2E, or Formula 2F, and provided that at least one of R 11 to R 16 or R 21 to R 30 is a group represented by one of the Formula 2A, Formula 2B, Formula 2C, Formula 2D, Formula 2E, or Formula 2F;

b1 to b4, b11 and b12 are independently selected from integers of 1 to 3;

i) in the Formula 1, when X 11 is N—[(L 11 ) a11 -(R 11 ) b11 ] and X 12 is not N-[(L 12 ) a12 -(R 12 ) b12 ], in the Formula 1, at least one of b11 R 11 's and R 21 to R 30 is selected from the group represented by the Formula 2A to the group represented by the Formula 2F;

ii) in the Formula 1, when X 11 is not N-[(L 11 ) a11 -(R 11 ) b11 ] and X 12 is N-[(L 12 ) a12 -(R 12 ) b12 ], in the Formula 1, at least one of b12 R 12 's and R 21 to R 30 is selected from the group represented by the Formula 2A to the group represented by the Formula 2F; and

iii) in the Formula 1, when X 11 is N-[(L 11 ) a11 -(R 11 ) b11 ] and X 12 is N-[(L 12 ) a12 -(R 12 ) b12 ], in the Formula 1, at least one of b11 R 11 's, and b12 R 12 's and R 21 to R 30 is selected from the group represented by the Formula 2A to the group represented by the Formula 2F;

at least one substituent of the substituted C 3 -C 10 cycloalkylene group, the substituted C 2 -C 10 heterocycloalkylene group, the substituted C 3 -C 10 cycloalkenylene group, the substituted C 2 -C 10 heterocycloalkenylene group, the substituted C 6 -C 60 arylene group, the substituted C 2 -C 60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic heterocondensed polycyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 2 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 2 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 2 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic heterocondensed polycyclic group is,

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group or a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group or a C 1 -C 60 alkoxy group each of which is substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ) and —B(Q 16 )(Q 17 );

a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group or a monovalent non-aromatic heterocondensed polycyclic group;

a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group each of which is substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ) and —B(Q 26 )(Q 27 ); or —N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ) or —B(Q 36 )(Q 37 );

wherein the Q 1 to Q 7 , Q 1 to Q 17 , Q 21 to Q 27 and Q 31 to Q 37 are independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group or a monovalent non-aromatic heterocondensed polycyclic group.

2. The condensed cyclic compound of claim 1 , wherein X 11 is N-[(L 11 ) a11 -(R 11 ) b11 ], S or O;

X 12 is N-[(L 12 ) a12 -(R 12 ) b12 ], S or O; and

X 1 is N-[(L 1 ) a1 -(R 1 ) b1 ], S or O.

3. The condensed cyclic compound of claim 1 , wherein the L 1 to L 4 , L 11 and L 12 are independently represented by one of Formulae 2-1 to 2-13:

wherein, in the Formulae 2-1 to 2-13,

Z 1 to Z 4 are independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group or —Si(Q 33 )(Q 34 )(Q 35 );

wherein the Q 33 to Q 35 are independently hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, quinazolinyl group or quinoxalinyl group; and

d1 is selected from integers of 1 to 4, d2 is selected from integers of 1 to 3, d3 is selected from integers of 1 to 6, d4 is selected from integers of 1 to 8, d6 is selected from integers of 1 to 5, * and *′ indicate bonding sites with a neighboring atom.

4. The condensed cyclic compound of claim 1 , wherein R 1 to R 6 , R 11 to R 16 and R 21 to R 30 are independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group each of which is substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof and a phosphoric acid or a salt thereof;

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphihyridinyl 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 benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobcnzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group or imidazopyrimidinyl 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 benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl 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, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group or an imidazopyrimidinyl group each of which is substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —Si(Q 33 )(Q 34 )(Q 35 ), 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 benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl 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, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and a biphenyl group;

—Si(Q 3 )(Q 4 )(Q 5 ), provided that the R 13 to R 16 and R 5 and R 6 are not —Si(Q 3 )(Q 4 )(Q 5 ); or

one of the groups represented by the Formula 2A to Formula 2F, provided that the R 1 to R 6 are not the group represented by the Formula 2A, Formula 2B, Formula 2C, Formula 2D, Formula 2E, or Formula 2F, and provided that at least one of R 11 to R 16 or R 21 to R 30 is a group represented by one of the Formula 2A, Formula 2B, Formula 2C, Formula 2D, Formula 2E, or Formula 2F;

wherein the Q 3 to Q 5 and Q 33 to Q 35 are independently hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group or a quinoxalinyl group.

5. The condensed cyclic compound of claim 1 , wherein the R 1 to R 6 , R 11 to R 16 and R 21 to R 30 are independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group each of which is substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof and a phosphoric acid or a salt thereof;

one of the following Formulae 4-1 to 4-31;

—Si(Q 3 )(Q 4 )(Q 5 ), provided that the R 13 to R 16 and R 5 to R 6 are not —Si(Q 3 )(Q 4 )(Q 5 ); or

one of the groups represented by the Formula 2A to Formula 2F, provided that R 1 to R 6 are not one of the groups represented by the Formula 2A, Formula 2B, Formula 2C, Formula 2D, Formula 2E, or Formula 2F, and provided that at least one of R 11 to R 16 or R 21 to R 30 is a group represented by one of the Formula 2A, Formula 2B, Formula 2C, Formula 2D, Formula 2E, or Formula 2F,

wherein, in the Formulae 4-1 to 4-31,

Y 31 is O, S, C(Z 33 )(Z 34 ), N(Z 35 ) or Si(Z 36 )(Z 37 ) (provided that in the Formula 4-23, Y 31 is not NH);

Z 31 to Z 37 are independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group or —Si(Q 33 )(Q 34 )(Q 35 );

wherein the Q 3 to Q 5 and Q 33 to Q 35 are independently hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group or a quinoxalinyl group;

e1 is selected from integers of 1 to 5, e2 is selected from integers of 1 to 7, e3 is selected from integers of 1 to 3, e4 is selected from integers of 1 to 4, e5 is 1 or 2, e6 is selected from integers of 1 to 6, and * indicates a bonding site with a neighboring atom.

6. The condensed cyclic compound of claim 1 , wherein R 2 in the Formula 2A and 2B, R 3 in the Formulae 2C and 2D, and at least one of R 2 and R 3 in the Formulae 2E and 2F is

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 benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl 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 benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group or an imidazopyrimidinyl group; or

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 benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl 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 benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group or an imidazopyrimidinyl group each of which is substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —Si(Q 33 )(Q 34 )(Q 35 ), 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 benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl 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 pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl 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 benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and a biphenyl group; and

wherein the Q 33 to Q 35 are independently hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group or a quinoxalinyl group.

7. The condensed cyclic compound of claim 1 , which is represented by one of the following Formulae 1-1 to 1-6:

wherein, in the Formulae 1-1 to 1-6, X 11 , X 12 and R 21 to R 30 are the same as in claim 1 .

8. The condensed cyclic compound of claim 7 , wherein the condensed cyclic compound is

i) represented by the Formula 1-1 or 1-2, wherein in the Formulae 1-1 and 1-2, R 21 is selected from the groups represented by the Formula 2A to Formula 2F, or

ii) represented by the Formula 1-1 or 1-6, wherein in the Formulae 1-1 and 1-6, X 11 is N-[(L 11 ) a11 -(R 11 ) b11 ], and R 11 is selected from the groups represented by the Formulae 2A to Formula 2F.

9. The condensed cyclic compound of claim 1 , which is one of the following compounds 1 to 40:

10. An organic light emitting device comprising

a first electrode; a second electrode facing the first electrode; and an organic layer including an emission layer interposed between the first electrode and the second electrode; wherein the organic layer comprises the condensed cyclic compound of claim 1 .

11. The organic light emitting device of claim 10 , wherein the condensed cyclic compound is present in the emission layer.

12. The organic light emitting device of claim 10 , wherein

the emission layer comprises a first host, a second host and a dopant,

the first host and the second host are different from each other,

the first host comprises the condensed cyclic compound,

the second host comprises at least one of a first compound represented by the following Formula 41 and a second compound represented by the following Formula 61:

wherein, in the Formulae

X 41 is N-[(L 42 ) a42 -(R 42 ) b42 ], S, O, S(═O), S(═O) 2 , C(═O), C(R 43 )(R 44 ), Si(R 43 )(R 44 ), P(R 43 ), P(═O)R 43 or C═N(R 43 );

in the Formula 61, the ring A 61 is represented by the Formula 61A;

in the Formula 61, the ring A 62 is represented by the Formula 61B;

X 61 is N-[(L 62 ) a62 -(R 62 ) b62 ], S, O, S(═O), S(═O) 2 , C(═O), C(R 63 )(R 64 ), Si(R 63 )(R 64 ), P(R 63 ), P(═O)R 63 or C═N(R 63 );

X 71 is C(R 71 ) or N, X 72 is C(R 72 ) or N, X 73 is C(R 73 ) or N, X 74 is C(R 74 ) or N, X 75 is C(R 75 ) or N, X 76 is C(R 76 ) or N, X 77 is C(R 77 ) or N, X 78 is C(R 78 ) or N;

Ar 41 , L 41 , L 42 , L 61 and L 62 are independently a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 2 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group;

n1 and n2 are independently selected from integers of 0 to 3;

a41, a42, a61 and a62 are independently selected from integers of 0 to 3;

R 41 to R 44 , R 51 to R 54 , R 61 to R 64 and R 71 to R 79 are independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, 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 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 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ) or —B(Q 6 )(Q 7 );

b41, b42, b51 to b54 b61, b62 and b79 are independently selected from integers of 1 to 3;

at least one substituent of the substituted C 3 -C 10 cycloalkylene group, the substituted C 2 -C 10 heterocycloalkylene group, the substituted C 3 -C 10 cycloalkenylene group, the substituted C 2 -C 10 heterocycloalkenylene group, the substituted C 6 -C 60 arylene group, the substituted C 2 -C 60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic heterocondensed polycyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 2 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 2 -C 60 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 2 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic heterocondensed polycyclic group is,

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group or a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group or a C 1 -C 60 alkoxy group each of which is substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ) and —B(Q 16 )(Q 17 );

a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group or a monovalent non-aromatic heterocondensed polycyclic group;

a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group each of which is substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ) and —B(Q 26 )(Q 27 ); or

—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ) or —B(Q 36 )(Q 37 );

wherein the Q 1 to Q 7 , Q 11 to Q 17 , Q 21 to Q 27 and Q 31 to Q 37 are independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group or a monovalent non-aromatic heterocondensed polycyclic group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 9, 2016
From: KIM, HYUNG-SUN; KIM, BYUNG-KU; KIM, YOUNG-KWON; KIM, CHANG-WOO; SEO, JOO-HEE; SHIN, CHANG-JU; LEE, SEUNG-JAE; HWANG, KYU YOUNG
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 038853/0578 →
Priority Claims (1)
KR 10-2014-0004697 · Jan 14, 2014 · national
Continuity (1)
Related Publication 20160308143A1 · Oct 20, 2016
Cited By (1)
US 12,201,020