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

Patent metadata

Field	Value
Publication number	US-9385336-B2
Application number	US-201414267103-A
Country	US
Kind code	B2
Filing date	May 1, 2014
Priority date	Jun 24, 2013
Publication date	Jul 5, 2016
Grant date	Jul 5, 2016

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.

First claim

What is claimed is:

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, a

Assignees

• Samsung Display Co Ltd

Inventors

• 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

Classifications

• C07D213/38

  having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C07D239/26

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title