IP Library Granted Patent US 9,525,141
Granted Patent B2
US 9,525,141 · App. 14/327,106 · Granted Dec 20, 2016

Organic light emitting device

Inventors: Dong-Hyun Kim (Yongin, KR); Mi-Kyung Kim (Yongin, KR); Se-Hun Kim (Yongin, KR); Hwan-Hee Cho (Yongin, KR); Chang-Woong Chu (Yongin, KR); Kwan-Hee Lee (Yongin, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H01L51/006H01L51/0061H01L51/0072H01L51/0073H01L51/0085H01L51/0087H01L51/5056H01L51/5072
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Quick Facts
Patent No.
US 9,525,141
App. No.
14/327,106
Granted
Dec 20, 2016
Kind
B2
Abstract

Provided is an organic light-emitting device, including a first electrode; a second electrode facing the first electrode; an emission layer (EML) disposed between the first electrode and the second electrode; a hole transporting region between the first electrode and the EML; and an electron transporting region between the EML and the second electrode. The hole transporting region includes an amine-based compound represented by one of Formulae 1A and 1C: The EML includes an organic metal complex and a compound represented by one of Formulae formula 2, 10A, 10B, 10C, 10D, and 10E:

Claims (102)

1. An organic light-emitting device, comprising:

a first electrode;

a second electrode facing the first electrode;

an emission layer (EML) disposed between the first electrode and the second electrode;

a hole transporting region between the first electrode and the EML; and

an electron transporting region between the EML and the second electrode,

wherein:

the hole transporting region includes an amine-based compound represented by one of Formulae 1A and 1C:

 and

the EML includes a host and a dopant, the dopant includes an organic metal complex and the host includes a compound represented by one of Formulae Formula 2, 10A, and 10E:

wherein Z 11 is N or C(R 11 ), Z 12 is N or C(R 12 ), Z 13 is N or C(R 13 ), Z 14 is N or C(R 14 ), Z 15 is N or C(R 15 ), Z 16 is N or C(R 16 ), Z 17 is N or C(R 17 ), Z 18 is N or C(R 18 ), Z 19 is N or C(R 19 ), Z 20 is N or C(R 20 ), and Z 21 is N or C(R 21 );

A 1 , A 2 , A 3 , and A 4 are each independently selected from benzene and naphthalene;

ring A and ring B are each independently selected from

i) a benzene or a naphthalene; and

ii) a benzene or a naphthalene, each substituted with at least one of a deuterium atom, a halogen atom, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, and a C 2 -C 60 heteroaryl group;

C 1 to C 4 each independently represent a carbon forming ring A or ring B;

X 1 is CR 1 or N;

X 2 is CR 2 or N;

R 1 and R 2 are each independently selected from a hydrogen, a deuterium, a halogen atom, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a C 2 -C 60 heteroaryl group, and —N(Q 1 )(Q 2 ), wherein Q 1 and Q 2 are each independently a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a C 2 -C 60 heteroaryl group, wherein R 1 and R 2 are optionally linked to each other to form a saturated or unsaturated C 6 -C 20 ring;

Y 1 is N-(L 1 ), n1 -Ar 11 ;

Y 2 is N-(L 2 ) n2 -Ar 12 , O, S, C(R 31 )(R 32 ), or Si(R 33 )(R 34 );

X 11 is O, S, C(R 41 )(R 42 ), Si(R 41 )(R 42 ), P(R 41 ), B(R 41 ), or P(═O)(R 41 );

E 1 is a substituted or unsubstituted electron transporting-cyclic group including at least one N as a ring-forming atom;

L 1 , L 2 , L 11 , L 21 , and L 22 are each independently selected from

a C 3 -C 10 cycloalkylene group, a C 2 -C 10 heterocycloalkylene group, a C 3 -C 10 cycloalkenylene group, a C 2 -C 10 heterocycloalkenylene group, a C 6 -C 60 arylene group, and a C 2 -C 60 heteroarylene group; and

a C 3 -C 10 cycloalkylene group, a C 2 -C 10 heterocycloalkylene group, a C 3 -C 10 cycloalkenylene group, a C 2 -C 10 heterocycloalkenylene group, a C 6 -C 60 arylene group, and a C 2 -C 60 heteroarylene group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 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, and a C 2 -C 60 heteroaryl group;

a1, a2, and a11 are each independently an integer selected from 0 to 5;

Ar 11 , Ar 12 , Ar 21 , and Ar 22 are each independently selected from

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, and a C 2 -C 60 heteroaryl group; and

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, and a C 2 -C 60 heteroaryl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 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, and a C 2 -C 60 heteroaryl group;

R 51 to R 54 , R 11 to R 21 , R 61 to R 64 , R 41 , R 42 , and R 31 to R 34 are each independently selected from

a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and 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, and a C 1 -C 60 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 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 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, and a C 2 -C 60 heteroaryl 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, and a C 2 -C 60 heteroaryl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 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, and a C 2 -C 60 heteroaryl group; and

—N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 ), wherein Q 11 to Q 17 are each independently a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, or a C 2 -C 60 heteroaryl group;

p, b1, b2, b3, and b4 are each independently an integer selected from 1 to 4;

q is an integer of 1 or 2; and

n1 and n2 are each independently an integer selected from 0 to 3,

wherein the amount of the organic metal complex is selected from a range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host.

2. The organic light-emitting device as claimed in claim 1 , wherein, in Formulae 1A and 1C, Z 11 is C(R 11 ), Z 12 is C(R 12 ), Z 13 is C(R 13 ), Z 14 is C(R 14 ), Z 15 is C(R 15 ), Z 16 is C(R 16 ), Z 17 is C(R 17 ), Z 18 is C(R 18 ), Z 19 is C(R 19 ), Z 20 is C(R 20 ), and Z 21 is C(R 21 ).

3. The organic light-emitting device as claimed in claim 1 , wherein the host includes a compound represented by Formula 2:

4. The organic light-emitting device as claimed in claim 1 , wherein, in Formula 2, A 1 is naphthalene or benzene, and A 2 , A 3 , and A 4 are benzene.

5. The organic light-emitting device as claimed in claim 1 , wherein, in Formula 2, X 11 is O, S, C(R 41 )(R 42 ), or Si(R 41 )(R 42 ), and R 41 and R 42 are optionally linked to each other to form a saturated or unsaturated ring.

6. The organic light-emitting device as claimed in claim 1 , wherein, in Formula 2, E 1 is selected from

a pyrrolyl group, an imidazolyl group, a pyrazolyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, and a triazinyl group; and

a pyrrolyl group, an imidazolyl group, a pyrazolyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 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, —Si(Q 21 )(Q 22 )(Q 23 ), and a C 6 -C 60 aryl group substituted with at least one —Si(Q 21 )(Q 22 )(Q 23 ), wherein Q 21 to Q 23 are each independently a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, and a C 2 -C 20 heteroaryl group.

7. The organic light-emitting device as claimed in claim 1 , wherein, in Formula 2, E 1 is selected from Formulae 11-1 to 11-17:

wherein Z 41 and Z 42 are each independently selected from a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl 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 carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a quinazolinyl group, —Si(Q 21 )(Q 22 )(Q 23 ), and a phenyl group substituted with at least one —Si(Q 21 )(Q 22 )(Q 23 ), wherein Q 21 to Q 23 are each independently a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, or a naphthyl group;

f1 is an integer of 1 to 4;

f2 is an integer of 1 to 3;

f3 is an integer of 1 or 2;

f4 is an integer of 1 to 6; and

f5 is an integer of 1 to 5.

8. The organic light-emitting device as claimed in claim 1 , wherein ring A and ring B are each independently selected from

i) benzene and naphthalene; and

ii) benzene and naphthalene, each substituted with at least one of a deuterium atom, a methyl group, an ethyl group, a t-butyl group, an octyl group, a phenyl group, a naphthyl group, a pyridyl group, and a pyrimidyl group.

9. The organic light-emitting device as claimed in claim 1 , wherein Ar 11 and Ar 12 are each independently represented by one selected from Formulae H1 to H81:

wherein * is a binding site with N, L 1 or L 2 .

10. The organic light-emitting device as claimed in claim 1 , wherein one of Formulae 10A, 10B, 10C, and 10E is represented by one selected from Formulae 1-1, 1-2, 1-4 to 1-12, and 1-16 to 1-28:

wherein Y 1 is N-(L 1 ) n1 -Ar 11 ;

Y 2 is N-(L 2 ) n2 -Ar 12 , O, S, C(R 31 )(R 32 ), or Si(R 33 )(R 34 );

L 1 and L 2 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenylene group, and a substituted or unsubstituted C 2 -C 60 heteroarylene group;

n1 and n2 are each independently an integer of 0 to 3;

Ar 1 and Ar 12 are each independently selected from

i) 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, and a C 2 -C 60 heteroaryl group; and

ii) 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, and a C 2 -C 60 heteroaryl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 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, and a C 2 -C 60 heteroaryl group;

R 31 to R 34 are each independently selected from

i) a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;

ii) a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 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, and a C 2 -C 60 heteroaryl group;

iii) 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, and a C 2 -C 60 heteroaryl group; and

iv) 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, and a C 2 -C 60 heteroaryl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 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, and a C 2 -C 60 heteroaryl group.

11. The organic light-emitting device as claimed in claim 1 , wherein L 1 , L 2 , L 11 , L 21 , and L 22 are each independently selected from

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzooxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group; and

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a Spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzooxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl 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 carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a quinazolinyl group.

12. The organic light-emitting device as claimed in claim 1 , wherein L 1 , L 2 , L 11 , L 21 , and L 22 are each independently selected from Formulae 3-1 to 3-32:

wherein Y 11 is O, S, S(═O), S(═O) 2 , C(Z 3 )(Z 4 ), N(Z 5 ), or Si(Z 6 )(Z 7 );

Z 1 to Z 7 are each independently selected from a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl 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 carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group

d1 is an integer of 1 to 4;

d2 is an integer of 1 to 3;

d3 is an integer of 1 to 6;

d4 is an integer of 1 to 8;

d5 is an integer of 1 to 2;

d6 is an integer of 1 to 5; and

* is a binding site with a neighboring atom.

13. The organic light-emitting device as claimed in claim 1 , wherein, in Formulae 1A and 1C, Ar 21 and Ar 22 are each independently selected from

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinylene group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinylene group, a carbazolyl group, and a triazinyl group.

14. The organic light-emitting device as claimed in claim 1 , wherein, in Formulae 1A and 1C, Ar 21 and Ar 22 are each independently represented by one of Formulae 5-1 to 5-20:

wherein * in Formulae 5-1 to 5-20 is a binding site with nitrogen (N), a binding site with L 21 , or a binding site with L 22 .

15. The organic light-emitting device as claimed in claim 1 , wherein, in Formula 1A and 1C, at least one of Ar 21 and Ar 22 is selected from

a naphthyl group; and

a naphthyl group substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinylene group, a carbazolyl group, and a triazinyl group.

16. The organic light-emitting device as claimed in claim 1 , wherein, in Formulae 1A and 1C, R 51 and R 52 are each independently selected from

a C 1 -C 20 alkyl group;

a C 1 -C 20 alkyl group substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinylene group, a carbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinylene group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinylene group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, a quinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinylene group, a carbazolyl group, and a triazinyl group.

17. The organic light-emitting device as claimed in claim 1 , wherein, in Formulae 1A, 1C, and 2, R 53 , R 54 , R 11 to R 21 , R 61 to R 64 , R 41 , and R 42 are each independently selected from a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, and groups represented by Formulae 5-1 to 5-20:

18. The organic light-emitting device as claimed in claim 1 , wherein, the amine-based compound is represented by one of Formulae 1A-1 and 1C-1:

19. The organic light-emitting device as claimed in claim 1 , wherein the amine-based compound is selected from Compounds 1 to 10:

20. The organic light-emitting device as claimed in claim 1 , wherein the host includes a compound selected from one of the following Compounds:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2014
From: KIM, DONG-HYUN; KIM, MI-KYUNG; KIM, SE-HUN; CHO, HWAN-HEE; CHU, CHANG-WOONG; LEE, KWAN-HEE
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 033274/0342 →
Priority Claims (1)
KR 10-2013-0102023 · Aug 27, 2013 · national
Continuity (1)
Related Publication 20150060796A1 · Mar 5, 2015