IP Library › Granted Patent US 10,158,086

Granted Patent B2

US 10,158,086 · App. 14/252,092 · Granted Dec 18, 2018

Organic light-emitting device

Inventors: Hwan-Hee Cho (Yongin, KR); Mi-Kyung Kim (Yongin, KR); Se-Hun Kim (Yongin, KR); Dong-Hyun Kim (Yongin, KR); Chang-Woong Chu (Yongin, KR)

Assignee: SAMSUNG DISPLAY CO., LTD.

H01L51/0072 C09K11/06 H01L51/0067 H01L51/006 H01L51/0054 H01L51/0061 H01L51/0071 H01L51/0077 H01L51/0085 H01L51/5012 H01L51/5016 H01L51/5056 H01L2251/308

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Quick Facts

Patent No.: US 10,158,086
App. No.: 14/252,092
Granted: Dec 18, 2018
Kind: B2

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Abstract

Provided is an organic light-emitting device including a first electrode; a second electrode disposed opposite to the first electrode; an emission layer disposed between the first electrode and the second electrode, the emission layer including at least one specific light-emitting material; and a hole-transporting region disposed between the first electrode and the emission layer, the hole-transporting region including at least one specific hole-transporting material.

Claims (102)

1. An organic light-emitting device, comprising:

a first electrode;

a second electrode disposed opposite to the first electrode;

an emission layer disposed between the first electrode and the second electrode, the emission layer including at least one light-emitting material represented by any one of Formulae 1A to 1E:

wherein, in Formulae 1A to 1E,

ring A and ring B are each independently selected from

i) a C 6 -C 20 aromatic ring and a C 2 -C 20 heteroaromatic ring; and

ii) a C 6 -C 20 aromatic ring and a C 2 -C 20 heteroaromatic ring each substituted with at least one selected from 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);

C 1 to C 4 each independently represent carbon atoms forming the ring A or the 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 hydrogen, 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 may connect to each other to selectively form a C 6 -C 20 saturated ring or a C 6 -C 20 unsaturated 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 );

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 11 and Ar 12 are each independently selected from

i) a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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 deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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 selected from deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, and a C 2 -C 60 heteroaryl group each substituted with at least selected from deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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

a hole-transporting region disposed between the first electrode and the emission layer, the hole-transporting region including at least one hole-transporting material represented by Formula 2(2):

wherein, in Formula 2(2),

X 11 is CR 11 or N; X 12 is CR 12 or N; X 13 is CR 13 or N; X 14 is CR 14 or N; X 15 is CR 15 or N; X 16 is CR 16 or N; X 17 is CR 17 or N; X 18 is CR 18 or N; X 19 is CR 19 or N; X 20 is CR 20 or N; X 21 is CR 21 or N; X 22 is CR 22 or N; X 23 is CR 23 or N; X 24 is CR 24 or N;

Z 3 , Z 4 , and R 11 to R 24 are each independently selected from

i) hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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;

iii) a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, and a C 2 -C 60 heteroaryl group;

iv) a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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 deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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

v) —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);

provided that Z 3 is not an amino group, an amidino group, or —N(Q 11 )(Q 12 ),

Ar 13 and Ar 14 are each independently selected from

Z 1 and Z 2 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 selected from deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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;

iv) a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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 deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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

p and q are each independently an integer of 1 to 4, and

wherein emission layer is a green phosphorescent emission layer or a red phosphorescent emission layer.

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

i) a C 6 -C 20 aromatic ring and a C 2 -C 20 heteroaromatic ring; and

ii) a C 6 -C 20 aromatic ring and a C 2 -C 20 heteroaromatic ring each substituted with at least one selected from deuterium, a halogen atom, a C 1 -C 10 alkyl group, a C 6 -C 20 aryl group, a C 2 -C 20 heteroaryl group, and —N(Q 1 )(Q 2 ) (wherein, Q 1 and Q 2 are each independently a C 6 -C 10 aryl group).

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

i) benzene, naphthalene, anthracene, pyridine, pyrimidine, pyrazine, quinoline, and isoquinoline; and

ii) benzene, naphthalene, anthracene, pyridine, pyrimidine, pyrazine, quinoline, and isoquinoline each substituted with at least one selected from deuterium, a methyl group, an ethyl group, a t-butyl group, an octyl group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, and —N(Ph) 2 .

4. The organic light-emitting device as claimed in claim 1 , wherein at least one of n1 and n2 is nonzero, and L 1 and L 2 are each independently selected from

i) a phenylene group, a pyridylene group, a pyrimidylene group, a triazinylene group, and a quinazolinylene group;

ii) a phenylene group, a pyridylene group, a pyrimidylene group, a triazinylene group, and a quinazolinylene group each substituted with at least one selected from a phenyl group, a naphthyl group, and a pyridyl group;

iii) a phenylene group, a pyridylene group, a pyrimidylene group, a triazinylene group, and a quinazolinylene group each substituted with at least one selected from deuterium, a methyl group, an ethyl group, an n-octyl group, a methoxy group, an ethoxy group, a phenyl group, a naphthyl group, a pyridyl group, and a carbazole group.

5. The organic light-emitting device as claimed in claim 1 , wherein Ar 11 and Ar 12 are each independently selected from

i) a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group; and

ii) a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group each substituted with at least one selected from a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, and a C 2 -C 60 heteroaryl group.

6. The organic light-emitting device as claimed in claim 1 , wherein Ar 11 and Ar 12 are each independently a compound represented by any one of Formulae H1 to H81:

wherein, in Formulae H1 to H81, * is a bonding site to N, L 1 , or L 2 .

7. The organic light-emitting device as claimed in claim 1 , wherein:

L 1 and L 2 are each independently selected from

i) a phenylene group, a pyridylene group, a pyrimidylene group, a triazinylene group, and a quinazolinylene group;

n1 and n2 are each independently an integer of 0 or 1;

Ar 11 and Ar 12 are each independently a compound represented by any one of Formulae H1, H3, H4, H6, H12, and H77 to H80:

8. The organic light-emitting device as claimed in claim 1 , wherein the light-emitting material is represented by any one of Formulae 1-1 to 1-28:

wherein, in Formulae 1-1 to 1-28,

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 );

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

Ar 11 and Ar 12 are each independently selected from

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 selected from deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 0 -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;

iv) a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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 deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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.

9. The organic light-emitting device as claimed in claim 1 , wherein the light-emitting material is represented by any one of Compounds 100 to 236:

10. The organic light-emitting device as claimed in claim 1 , wherein X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), X 18 is C(R 18 ), X 19 is C(R 19 ), X 20 is C(R 20 ), X 21 is C(R 21 ), X 22 is C(R 22 ), X 23 is C(R 23 ), and X 24 is C(R 24 ).

11. The organic light-emitting device as claimed in claim 1 , wherein Ar 13 and Ar 14 are each independently selected from

i) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthryl 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

ii) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthryl 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 deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 anthryl 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.

12. The organic light-emitting device as claimed in claim 1 , wherein Ar 13 and Ar 14 are each independently represented by any one of Formulae 3-1 to 3-20:

wherein, in Formulae 3-1 to 3-20, * represents a bonding site to N of Formula 2(2).

13. The organic light-emitting device as claimed in claim 1 , wherein Z 1 and Z 2 are each independently selected from

i) a C 1 -C 20 alkyl group;

ii) a C 1 -C 20 alkyl group substituted with at least one selected from deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 anthryl 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;

iii) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthryl 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

iv) a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenanthrenyl group, an anthryl 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 deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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 anthryl 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 Z 1 and Z 2 are each independently selected from a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and a compound represented by any one of Formulae 3-1 to 3-20:

wherein, in Formulae 3-1 to 3-20, * represents a carbon atom of a fluorene ring in Formula 2(2).

15. The organic light-emitting device as claimed in claim 1 , wherein Z 3 , Z 4 , and R 11 to R 24 are each independently selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, and a C 1 -C 20 alkyl group, provided that Z 3 is not an amino group or an amidino group.

16. The organic light-emitting device as claimed in claim 1 , wherein Z 3 , Z 4 , and R 11 to R 24 are each independently selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and a compound represented by any one of Formulae 3-1 to 3-20, provided that Z 3 is not an amino group or an amidino group:

17. The organic light-emitting device as claimed in claim 1 , wherein the hole-transporting material is represented by Formula 2b:

wherein, in Formula 2b,

Ar 13 and Ar 14 are each independently represented by any one of Formulae 3-1 to 3-20:

Z 1 and Z 2 are each independently represented by any one of a C 1 -C 20 alkyl group and Formulae 3-1 to 3-20;

Z 3 , Z 4 , and R 11 to R 24 are each independently selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl 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, and compounds represented by any one of Formulae 3-1 to 3-20, provided that Z3 is not an amino group or an amidino group; and

p and q are each independently an integer of 1 to 4.

18. The organic light-emitting device as claimed in claim 1 , wherein the hole-transporting material is represented by any one of Compounds 6-73 to 6-144:

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2014

From: CHO, HWAN-HEE; KIM, MI-KYUNG; KIM, SE-HUN; KIM, DONG-HYUN; CHU, CHANG-WOONG

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 032667/0150 →

Priority Claims (1)

KR 10-2013-0068641 · Jun 14, 2013 · national

Continuity (1)

Related Publication 20140374711A1 · Dec 25, 2014