IP Library Granted Patent US 9,385,336
Granted Patent B2
US 9,385,336 · App. 14/267,103 · Granted Jul 5, 2016

Organic light-emitting device using a mixture of electron transporting compounds

Inventors: Se-Jin Cho (Yongin, KR); Chang-Ho Lee (Yongin, KR); Dae-Yup Shin (Yongin, KR); Young-Mok Son (Yongin, KR); Il-Soo Oh (Yongin, KR); Hee-Joo Ko (Yongin, KR); Jin-Young Yun (Yongin, KR); Bo-Ra Lee (Yongin, KR); Yeon-Woo Lee (Yongin, KR); Beom-Joon Kim (Yongin, KR); Pyung-Eun Jeon (Yongin, KR); Hyun-Ju Choi (Yongin, KR); Chang-Min Lee (Yongin, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H01L51/5004C09K11/06H01L51/006H01L51/0061H01L51/5072C09K2211/1011C09K2211/1014C09K2211/1044H01L51/0058H01L51/0067H01L51/0077H01L51/5056H01L2251/308
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Quick Facts
Patent No.
US 9,385,336
App. No.
14/267,103
Granted
Jul 5, 2016
Kind
B2
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, and an electron-transporting layer disposed between the emission layer and the second electrode. The electron-transporting layer includes a first electron-transporting material and a second electron-transporting material. The lowest unoccupied molecular orbital (LUMO) energy level of the first electron-transporting material (EL 1 ) and the lowest unoccupied molecular orbital (LUMO) energy level of the second electron-transporting material (EL 2 ) satisfy the equation 0.1 eV≦|EL 1 −EL 2 |≦0.3 eV.

Claims (69)

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; and

an electron-transporting layer disposed between the emission layer and the second electrode; wherein

the electron-transporting layer includes a first electron-transporting material and a second electron-transporting material; and

a lowest unoccupied molecular orbital (LUMO) energy level of the first electron-transporting material (EL 1 ) and a lowest unoccupied molecular orbital (LUMO) energy level of the second electron-transporting material (EL 2 ) satisfy the equation 0.1 eV≦|EL 1 −EL 2 |≦0.3 eV,

wherein the first electron-transporting material and the second electron-transporting material are each independently selected from an amine-based compound represented by Formula 1 and an anthracene-based compound represented by Formula 2:

wherein in Formulae 1 and 2,

groups represented by X 1 and X 2 are each independently selected from a substituted or unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted C 2 -C 60 heteroarylene group;

m1 and m2 are each independently an integer of 0 to 5;

groups represented by Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted C 6 -C 60 aryl group and a substituted or unsubstituted C 2 -C 60 heteroaryl group; wherein

at least one of the groups represented by Ar 1 and Ar 2 is selected from i) a pyridyl group, a pyrimidyl group, and a triazinyl group, ii) a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group; iii) a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group each substituted with at least one of a pyridyl group, a pyrimidyl group, and a triazinyl group; and iv) a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group, which are each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group; and

a group represented by Ar 3 is selected from i) a pyridyl group, a pyrimidyl group, and a triazinyl group, ii) a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group; iii) a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group each substituted with at least one of a pyridyl group, a pyrimidyl group, and a triazinyl group; and iv) a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group, which are each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group.

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

a highest occupied molecular orbital (HOMO) energy level of the first electron-transporting material (EH 1 ) and the lowest unoccupied molecular orbital (LUMO) energy level of the first electron-transporting material (EL 1 ) satisfy the equation

2.7 eV≦| EL 1 −EH 1 |≦3.2 eV; and

a highest occupied molecular orbital (HOMO) of the second electron-transporting material (EH 2 ) and the lowest unoccupied molecular orbital (LUMO) energy level of the second electron-transporting material (EL 2 ) satisfy the equation,

2.7 eV≦| EL 2 −EH 2 |≦3.2 eV.

3. The organic light-emitting device as claimed in claim 1 , wherein a molecular weight of the first electron-transporting material (MW 1 ) and a molecular weight of the second electron-transporting material (MW 2 ) satisfy the equation, |MW 1 −MW 2 |≦30.

4. The organic light-emitting device as claimed in claim 1 , wherein both of the first electron-transporting material and the second electron-transporting material are each non-metal-atom-containing organic compounds.

5. The organic light-emitting device as claimed in claim 1 , wherein the first electron-transporting material and the second electron-transporting material are each independently selected from a pyridine derivative, a pyrimidine derivative, and a triazine derivative.

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

the LUMO energy level of the EL 1 satisfies the equation 2.6 eV≦|EL 1 |≦2.9 eV; and

the LUMO energy level of the EL 2 satisfies the equation 2.7 eV≦|EL 1 |≦3.0 eV.

7. The organic light-emitting device as claimed in claim 1 , wherein the first electron-transporting material and the second electron-transporting material are each independently selected from Compounds 1 to 15:

8. 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; and

an electron-transporting layer disposed between the emission layer and the second electrode, wherein

the electron-transporting layer includes a first electron-transporting material and a second electron-transporting material,

the first electron-transporting material and the second electron-transporting material are each independently selected from an amine-based compound represented by Formula 1 and an anthracene-based compound represented by Formula 2,

the first electron-transporting material and the second electron-transporting material are different:

wherein Formulae 1 and 2, groups represented by X 1 and X 2 are each independently selected from a substituted or unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted C 2 -C 60 heteroarylene group;

m1 and m2 are each independently an integer of 0 to 5;

groups represented by Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted C 6 -C 60 aryl group and a substituted or unsubstituted C 2 -C 60 heteroaryl group; wherein

at least one of the groups represented by Ar 1 and Ar 2 is selected from i) a pyridyl group, a pyrimidyl group, and a triazinyl group, ii) a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group; iii) a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group each substituted with at least one of a pyridyl group, a pyrimidyl group, and a triazinyl group; and iv) a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group, which are each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group; and

a group represented by Ar 3 is selected from i) a pyridyl group, a pyrimidyl group, and a triazinyl group, ii) a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group; iii) a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group each substituted with at least one of a pyridyl group, a pyrimidyl group, and a triazinyl group; and iv) a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group, which are each substituted with at least one of a C 6 -C 60 aryl group and a C 2 -C 60 heteroaryl group.

9. The organic light-emitting device as claimed in claim 8 , wherein groups represented by X 1 and X 2 are each independently selected from a substituted or unsubstituted a phenylene group, a substituted or unsubstituted a naphthylene group, a substituted or unsubstituted an anthrylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, and a substituted or unsubstituted triazolylene group.

10. The organic light-emitting device as claimed in claim 8 , wherein m1 and m2 are each independently an integer of 1 or 2.

11. The organic light-emitting device as claimed in claim 8 , wherein moieties represented by (X 1 ) m1 and (X 2 ) m2 are each independently selected from Formulae 3-1 to 3-4:

wherein groups represented by Z 1 to Z 8 are each independently selected from a hydrogen atom; a deuterium atom; —F; —Cl; —Br; —I; —CN; a hydroxyl group; —NO 2 ; a C 1 -C 20 alkyl group; a C 1 -C 20 alkoxy group; a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group each substituted with at least one of a deuterium atom, —F, —Cl, —Br, —I, —CN, a hydroxyl group, and —NO 2 ; a C 6 -C 20 aryl group; a C 2 -C 20 heteroaryl group; and a C 6 -C 20 aryl group and a C 2 -C 20 heteroaryl group each substituted with at least one of a deuterium atom, —F, —Cl, —Br, —I, —CN, a hydroxyl group, —NO 2 , 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;

* is a bonding site to anthracene of Formulae 1 and 2; and

** is a bonding site to a nitrogen atom of Formula 1 or a bonding site to a group represented by Ar 3 of Formula 2.

12. The organic light-emitting device as claimed in claim 8 , wherein groups represented by Ar 1 and Ar 2 are each independently represented by any one selected from Formulae 4-1 to 4-9, provided that at least one of groups represented by An and Ar e is represented by any one of Formulae 4-1 to 4-6:

wherein groups represented by Y 1 to Y 8 are each independently selected from a hydrogen atom, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group and a triazinyl group; wherein

* is a bonding site to a nitrogen atom of Formula 1.

13. The organic light-emitting device as claimed in claim 8 , wherein a group represented by Ar 3 is selected from i) a pyridyl group, a pyrimidyl group, and a triazinyl group; ii) a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, and a triazinyl group; iii) a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a pyridyl group, a pyrimidyl group, and a triazinyl group; and iv) a pyridyl group, a pyrimidyl group, and a triazinyl group each substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, and a triazinyl group, which are each substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, and a triazinyl group.

14. The organic light-emitting device as claimed in claim 8 , wherein a group represented by Ar 3 is represented by any one of Formulae 4-1 to 4-6:

wherein groups represented by Y 1 to Y 8 are each independently selected from a hydrogen atom, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, and a triazinyl group; and * is a bonding site to a nitrogen atom of Formula 1.

15. The organic light-emitting device as claimed in claim 8 , wherein the first electron-transporting material and the second electron-transporting material are each independently selected from Compounds 1 to 15:

16. The organic light-emitting device as claimed in claim 8 , wherein a lowest unoccupied molecular orbital energy level (LUMO) of the first electron-transporting material (EL 1 ) and a lowest unoccupied molecular orbital (LUMO) energy level of the second electron-transporting material (EL 2 ) satisfy the equation, 0.1 eV≦|EL 1 −EL 2 |≦0.3 eV.

17. The organic light-emitting device as claimed in claim 16 , wherein:

the LUMO energy level of the EL 1 satisfies the equation 2.6 eV≦|EL 1 |≦2.9 eV; and

the LUMO energy level of the EL 2 satisfies the equation 2.7 eV≦|EL 1 |≦3.0 eV.

18. The organic light-emitting device as claimed in claim 8 , wherein a highest occupied molecular orbital (HOMO) energy level of the first electron-transporting material (EH 1 ) and a lowest unoccupied molecular orbital (LUMO) energy level of the first electron-transporting material (EL 1 ) satisfy the equation, 2.7 eV≦|EL 1 −EH 1 |≦3.2 eV; and

a highest occupied molecular orbital (HOMO) energy level of the second electron-transporting material (EH 2 ) and a lowest unoccupied molecular orbital (LUMO) of the second electron-transporting material (EL 2 ) satisfy 2.7 eV≦|EL 2 −EH 2 |≦3.2 eV.

19. The organic light-emitting device as claimed in claim 8 , wherein:

i) the first electron-transporting material is at least one selected from amine-based compounds represented by Formula 1 and the second electron-transporting material is at least one selected from the amine-based compounds represented by Formula 1;

ii) the first electron-transporting material is at least one selected from the amine-based compounds represented by Formula 1 and the second electron-transporting material is at least one selected from anthracene-based compounds represented by Formula 2; or

iii) the first electron-transporting material is at least one selected from the anthracene-based compounds represented by Formula 2 and the second electron-transporting material is at least one selected from the anthracene-based compounds represented by Formula 2.

20. The organic light-emitting device as claimed in claim 8 , wherein:

i) the first electron-transporting material and the second electron-transporting material are each independently at least one selected from Compounds 1 to 5;

ii) the first electron-transporting material is at least one selected from Compounds 1 to 5 and the second electron-transporting material is at least one selected from Compounds 6 to 10;

iii) the first electron-transporting material is at least one selected from Compounds 1 to 5 and the second electron-transporting material is at least one selected from Compounds 11 to 15;

iv) the first electron-transporting material and the second electron-transporting material are each independently at least one selected from Compounds 6 to 10;

v) the first electron-transporting material is at least one selected from Compounds 6 to 10 and the second electron-transporting material is at least one selected from Compounds 11 to 15; or

vi) the first electron-transporting material and the second electron-transporting material are each independently at least one selected from Compounds 11 to 15,

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2014
From: CHO, SE-JIN; LEE, CHANG-HO; SHIN, DAE-YUP; SON, YOUNG-MOK; OH, IL-SOO; KO, HEE-JOO; YUN, JIN-YOUNG; LEE, BO-RA; LEE, YEON-WOO; KIM, BEOM-JOON; JEON, PYUNG-EUN; CHOI, HYUN-JU; LEE, CHANG-MIN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 032799/0709 →
Priority Claims (1)
KR 10-2013-0072707 · Jun 24, 2013 · national
Continuity (1)
Related Publication 20140374713A1 · Dec 25, 2014