IP Library Granted Patent US 9,815,821
Granted Patent B2
US 9,815,821 · App. 13/681,208 · Granted Nov 14, 2017

Condensed-cyclic compound and organic light emitting diode including the same

Inventors: Myeong-Suk Kim (Yongin-si, KR); Tae-Kyung Kim (Yongin-si, KR); Jeoung-In Yi (Yongin-si, KR); Jeong-Soo Kim (Cheongwon-gun, KR); Su-Jin Lee (Cheongwon-gun, KR); Hyun-Jung Kwon (Cheongwon-gun, KR); Sang-Won Ko (Cheongwon-gun, KR)
Assignees: Samsung Display Co., Ltd.; SFC Co., Ltd
C07D403/14C07D209/86C07D307/91C07D333/76C07D403/10H01L51/006H01L51/5092H01L51/0054H01L51/0081H01L51/5012H01L2251/308
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Quick Facts
Patent No.
US 9,815,821
App. No.
13/681,208
Granted
Nov 14, 2017
Kind
B2
Abstract

Embodiments of the present invention are directed to a condensed-cyclic compound and an OLED including the same.

Claims (50)

1. A condensed-cyclic compound represented by Formula 1:

Ar 1 Ar 2 ) q   Formula 1

wherein:

q is an integer of 1 to 6, and when q is 2 or greater, 2 or more of Ar 2 are identical to or different from each other;

Ar 2 is represented by Formula 2:

 wherein Cy is a substituted or unsubstituted C 3 to C 8 cycloalkane;

X 1 is N(R 11 ), B(R 11 ), Si(R 11 )(R 12 ), O, or S;

X 2 is a single bond or —[C(R 15 )(R 16 )] n —, wherein n is an integer of 1 to 3, and when n is 2 or greater, 2 or more R 15 and R 16 groups are identical to or different from each other;

L 1 is a single bond, a substituted or unsubstituted C 1 -C 60 alkylene group, a substituted or unsubstituted C 2 -C 60 alkynylene group, a substituted or unsubstituted C 3 -C 60 cycloalkylene group, a substituted or unsubstituted C 2 -C 60 heterocycloalkylene group, a substituted or unsubstituted C 5 -C 60 arylene group, or a substituted or unsubstituted C 2 -C 60 heteroarylene;

R 1 through R 3 , R 11 , R 12 , R 15 , and R 16 are each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group 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 1 -C 60 alkylthio group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 5 -C 60 aryl group, a substituted or unsubstituted C 5 -C 60 aryloxy group, a substituted or unsubstituted C 5 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a (substituted or unsubstituted C 1 -C 60 alkyl) amino group, a di(substituted or unsubstituted C 1 -C 60 alkyl) amino group, or a (substituted or unsubstituted C 5 -C 60 aryl) amino group, a di(substituted or unsubstituted C 5 -C 60 aryl) amino group;

a is an integer of 1 to 3, and when a is 2 or greater, 2 or more R 3 groups are identical to or different from each other; and

* is a binding site to Ar 1 of Formula 1; and

Ar 1 is represented by any one of Formulae 3A through 3C and 3E-3G:

wherein R 20 through R 39 are each independently a binding site to Ar 2 represented by Formula 2, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group 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 1 -C 60 alkylthio group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 5 -C 60 aryl group, a substituted or unsubstituted C 5 -C 60 aryloxy group, a substituted or unsubstituted C 5 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a(substituted or unsubstituted C 1 -C 60 alkyl) amino group, a di(substituted or unsubstituted C 1 -C 60 alkyl) amino group, or a (substituted or unsubstituted C 5 -C 60 aryl) amino group or a di(substituted or unsubstituted C 5 -C 60 aryl) amino group, wherein one to six groups selected from R 20 through R 39 are binding sites to Ar 2 represented by Formula 2.

2. The condensed-cyclic compound of claim 1 , wherein Ar 1 is represented by any one of Formulae 3A-1 through 3C-1 and 3E-1 through 3G-1:

wherein R 20 through R 25 are each independently any one of a binding site to Ar 2 represented by Formula 2; hydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; hydrazine; hydrazone; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; a C 1 -C 10 alkylthio group; a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and C 1 -C 10 alkylthio group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; an anthryl group; a pyrenyl group; a chrysenyl group; a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a chrysenyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group; an indolyl group; a benzoimidazolyl group; a carbazolyl group; an imidazolyl group; an imidazolynyl group; an imidazopyridinyl group; an imidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; a triazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolyl group, a carbazolyl group, an imidazolyl group, an imidazolynyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and a quinolinyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 1 -C 10 alkylthio group, a phenyl group, and a naphthyl group; a di(C 1 -C 10 alkyl) amino group; and a di(C 6 -C 20 aryl) amino group, wherein the C 6 -C 20 aryl group is a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, or a chrysenyl group;

at least one of R 20 through R 23 of Formulae 3A-1 and 3C-1 is a binding site to Ar 2 represented by Formula 2 ;

at least one of R 24 through R 25 of Formula 3 A- 2 is a binding site to Ar 2 represented by Formula 2;

at least one of R 20 through R 21 of Formulae 3B-1, 3E-1, 3F-1, and 3G-1 is a binding site to Ar 2 represented by Formula 2; and

at least one of R 22 through R 23 of Formulae 3B-2, 3E-2, and 3F-2 is a binding site to Ar 2 represented by Formula 2.

3. The condensed-cyclic compound of claim 1 , wherein Ar 1 is represented by any one of Formulae 3A-1 through 3B-1 below:

wherein R 20 through R 23 are each independently a binding site to Ar 2 represented by Formula 2; hydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; hydrazine; hydrazone; a carboxyl group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid or a salt thereof; a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; a C 1 -C 10 alkylthio group; a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid or a salt thereof; a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; an anthryl group; a pyrenyl group; a chrysenyl group; a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a chrysenyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group; a di(C 1 -C 10 alkyl) amino group; and a di(C 6 -C 20 aryl) amino group, wherein the C 6 -C 20 aryl group is a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, or a chrysenyl group;

at least one of R 20 through R 23 of Formula 3A-1 is a binding site to Ar 2 represented by Formula 2; and

at least one of R 20 and R 21 of Formula 3B-1 is a binding site to Ar 2 represented by Formula 2.

4. The condensed-cyclic compound of claim 1 , wherein X 1 in Formula 2 is N(R 11 ), B(R 11 ), or Si(R 11 )(R 12 ), wherein R 11 and R 12 are each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted azulenyl, a substituted or unsubstituted heptalenyl, a substituted or unsubstituted indacenyl, a substituted or unsubstituted acenaphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pentaphenyl group, a substituted or unsubstituted hexacenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted imidazolinyl group, a substituted or unsubstituted imidazopyridinyl group, a substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted indolizinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted pyranyl group, a substituted or unsubstituted chromenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted oxadiazolyl group.

5. The condensed-cyclic compound of claim 1 , wherein X 1 in Formula 2 is N(R 11 ), B(R 11 ), or Si(R 11 )(R 12 ), wherein R 11 and R 12 are each independently represented by any one of Formulae 4A through 4H:

wherein Z 1 through Z 7 are each independently any one of hydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; hydrazine; hydrazone; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; a C 1 -C 10 alkylthio group; a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; an anthryl group; a pyrenyl group; a chrysenyl group; a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a chrysenyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group; an indolyl group; a benzoimidazolyl group; a carbazolyl group; an imidazolyl group; an imidazolynyl group; an imidazopyridinyl group; an imidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; a triazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolyl group, a carbazolyl group, an imidazolyl group, an imidazolynyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and a quinolinyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 1 -C 10 alkylthio group, a phenyl group, and a naphthyl group; a di(C 1 -C 10 alkyl) amino group; and a di(C 6 -C 20 aryl) amino group, wherein the C 6 -C 20 aryl group is a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, or a chrysenyl group.

6. The condensed-cyclic compound of claim 1 , wherein X 1 in Formula 2 is O or S.

7. The condensed-cyclic compound of claim 1 , wherein X 2 in Formula 2 is a single bond.

8. The condensed-cyclic compound of claim 1 , wherein L 1 in Formula 2 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted azulenylene group, a substituted or unsubstituted heptalenylene group, a substituted or unsubstituted indacenylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenalenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted naphthacenylene group, a substituted or unsubstituted pycenylene group, a substituted or unsubstituted perylenylene group, a substituted or unsubstituted pentacenylene group, a substituted or unsubstituted hexacenylene group, a substituted or unsubstituted pyrrolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted imidazolylene group, a substituted or unsubstituted imidazolinylene group, a substituted or unsubstituted imidazopyridinylene group, a substituted or unsubstituted imidazopyrimidinylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted indolizinylene group, a substituted or unsubstituted naphthyridinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted cinnolinylene group, a substituted or unsubstituted indazolylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted phenazinylene group, a substituted or unsubstituted phenanthridinylene group, a substituted or unsubstituted pyranylene group, a substituted or unsubstituted chromenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted isothiazolylene group, a substituted or unsubstituted benzoimidazolylene group, a substituted or unsubstituted isoxazolylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted triazinylene group, or a substituted or unsubstituted oxadiazolylene group.

9. The condensed-cyclic compound of claim 1 , wherein L 1 in Formula 2 is a single bond or any one of Formulae 5A through 5K:

wherein Z 11 through Z 16 are each independently one of hydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; hydrazine; hydrazone; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; a C 1 -C 10 alkylthio group; a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; an anthryl group; a pyrenyl group; a chrysenyl group; a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a chrysenyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group; an indolyl group; a benzoimidazolyl group; a carbazolyl group; an imidazolyl group; an imidazolinyl group; an imidazopyridinyl group; an imidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; a triazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolyl group, a carbazolyl group, an imidazolyl group, an imidazolinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and a quinolinyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 1 -C 10 alkylthio group, a phenyl group, and a naphthyl group; a di(C 1 -C 10 alkyl) amino group; and a di(C 6 -C 20 aryl) amino group, wherein the C 6 -C 20 aryl group is a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, or a chrysenyl group.

10. The condensed-cyclic compound of claim 1 , wherein Ar 2 is represented by any one of Formulae 2A through 2K:

wherein X 1 , L 1 , R 1 through R 3 , a, and * are as described in claim 1 ;

R 40 through R 51 are each independently one of hydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; hydrazine; hydrazone; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; a C 1 -C 10 alkylthio group; a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group substituted by one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; an anthryl group; a pyrenyl group; a chrysenyl group; a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a chrysenyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group; an indolyl group; a benzoimidazolyl group; a carbazolyl group; an imidazolyl group; an imidazolinyl group; an imidazopyridinyl group; an imidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; a triazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolyl group, a carbazolyl group, an imidazolyl group, an imidazolinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and a quinolinyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 1 -C 10 alkylthio group, a phenyl group, and a naphthyl group; a di(C 1 -C 10 alkyl) amino group; and a di(C 6 -C 20 aryl) amino group, wherein the C 6 -C 20 aryl group is a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, or a chrysenyl group.

11. The condensed-cyclic compound of claim 10 , wherein R 40 through R 51 are each independently any one of hydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; hydrazine; hydrazone; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; a C 1 -C 10 alkylthio group; and a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof.

12. The condensed-cyclic compound of claim 10 , wherein R 1 through R 3 are each independently any one of hydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; hydrazine; hydrazone; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; a C 1 -C 10 alkylthio group; and a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof.

13. The condensed-cyclic compound of claim 1 , wherein Ar 2 is represented by Formula 2-1:

wherein L 1 , R 1 through R 3 , a, and Cy are as described in claim 1 ;

Z 1 through Z 5 are each independently any one of hydrogen; deuterium; a halogen atom; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; hydrazine; hydrazone; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; a C 1 -C 10 alkylthio group; a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; an anthryl group; a pyrenyl group; a chrysenyl group; a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a chrysenyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 1 -C 10 alkylthio group; an indolyl group; a benzoimidazolyl group; a carbazolyl group; an imidazolyl group; an imidazolinyl group; an imidazopyridinyl group; an imidazopyrimidinyl group; a pyridinyl group; a pyrimidinyl group; a triazinyl group; a quinolinyl group; an indolyl group, a benzoimidazolyl group, a carbazolyl group, an imidazolyl group, an imidazolinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and a quinolinyl group substituted with one or more of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 1 -C 10 alkylthio group, a phenyl group, and a naphthyl group; a di(C 1 -C 10 alkyl) amino group; and a di(C 6 -C 20 aryl) amino group, wherein the C 6 -C 20 aryl group is a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, or a chrysenyl group.

14. The condensed-cyclic compound of claim 1 , wherein the condensed-cyclic compound is one of Compounds 38, 262, 586, 726, or 929:

15. An organic light-emitting diode comprising:

a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises the condensed-cyclic compound according to claim 1 .

16. The organic light-emitting diode of claim 15 , wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a functional layer having hole injection and hole transport abilities, an emission layer, an electron transport layer, and an electron injection layer.

17. The organic light-emitting diode of claim 16 , wherein the organic layer comprises an emission layer comprising the condensed-cyclic compound.

18. The organic light-emitting diode of claim 17 , wherein the emission layer further comprises a host and the condensed-cyclic compound in the emission layer acts as a dopant.

19. The organic light-emitting diode of claim 18 , wherein the host comprises an anthracene-based compound represented by Formula 60:

wherein Ar 11 and Ar 12 are each independently a substituted or unsubstituted C 5 -C 60 arylene group;

Ar 13 and Ar 14 are each independently a substituted or unsubstituted C 1 -C 10 alkyl group or a substituted or unsubstituted C 5 -C 60 aryl group; and

e and f are each independently an integer of 0 to 5.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 21, 2012
From: KIM, MYEONG-SUK; KIM, TAE-KYUNG; YI, JEOUNG-IN; KIM, JEONG-SOO; LEE, SU-JIN; KWON, HYUN-JUNG; KO, SANG-WON
To: SAMSUNG DISPLAY CO., LTD; SFC CO., LTD.
Reel/Frame 029339/0200 →
Priority Claims (1)
KR 10-2011-0143911 · Dec 27, 2011 · national
Continuity (1)
Related Publication 20130175509A1 · Jul 11, 2013