IP Library Granted Patent US 9,966,536
Granted Patent B2
US 9,966,536 · App. 14/701,307 · Granted May 8, 2018

Organic electroluminescence device

Inventor: Hiroaki Itoi (Yokohama, JP)
Assignee: SAMSUNG DISPLAY CO., LTD.
H01L51/0061H01L51/006H01L51/0058H01L51/0067H01L51/0072H01L51/0073H01L51/0074H01L51/0081H01L51/5004H01L51/506H01L51/5012H01L51/5056H01L51/5064H01L2251/308H01L2251/552
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Quick Facts
Patent No.
US 9,966,536
App. No.
14/701,307
Granted
May 8, 2018
Kind
B2
Abstract

An organic electroluminescent (EL) device including an anode; an emission layer for obtaining luminescence via a singlet excited state; and a laminated structure between the anode and the emission layer, the laminated structure including at least three layers having different components, wherein the laminated structure includes a first layer including a hole transport compound, the hole transport compound being obtained by doping an electron accepting compound having a lowest unoccupied molecular orbital (LUMO) level of about −9.0 eV to about −4.0 eV; and a second layer between the first layer and the emission layer, the second layer being closer to the emission layer than the first layer and including a compound represented by the following Formula 1:

Claims (49)

1. An organic electroluminescent (EL) device, comprising:

an anode;

an emission layer for obtaining luminescence via a singlet excited state; and

a laminated structure between the anode and the emission layer, the laminated structure including at least three layers having different components,

wherein the laminated structure includes:

a first layer including a hole transport compound, the hole transport compound being doped with an electron accepting compound that has a lowest unoccupied molecular orbital (LUMO) level of about −9.0 eV to about −4.0 eV;

a second layer between the first layer and the emission layer, the second layer being closer to the emission layer than the first layer and including a compound represented by the following Formula 1,

a third layer between the first layer and the second layer, the third layer includes a compound represented by the following Formula 2:

wherein, in Formula 1,

Ar 5 to Ar 8 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms,

adjacent Ar 7 s can be combined to form a ring, and adjacent Ar 8 s can be combined to form a ring,

each m is independently an integer of 0 to 4, and

L 2 and L 3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms,

wherein, in Formula 2,

Ar 1 , Ar 2 , and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms,

Ar 4 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and

L 1 is a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms.

2. The organic EL device as claimed in claim 1 , wherein the first layer includes a compound represented by Formula 2.

3. The organic EL device as claimed in claim 1 , wherein the emission layer includes an anthracene-containing compound represented by the following Formula 3:

wherein, in Formula 3,

each Ar 9 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and

n is an integer of 1 to 10.

4. The organic EL device as claimed in claim 3 , wherein the second layer includes one of the following Compounds 1 to 22:

5. The organic EL device as claimed in claim 1 , wherein the third layer includes one of the following Compounds 23 to 38:

6. The organic EL device as claimed in claim 3 , wherein the anthracene-containing compound includes one of the following Compounds a-1 to a-12:

7. An organic electroluminescent (EL) device, comprising:

an anode;

an emission layer for obtaining luminescence via a singlet excited state; and

a laminated structure between the anode and the emission layer, the laminated structure including at least three layers having different components,

wherein the laminated structure includes:

a first layer including an electron accepting compound having a lowest unoccupied molecular orbital (LUMO) level of about −9.0 eV to about −4.0 eV as a main component;

a second layer between the first layer and the emission layer, the second layer being adjacent to the emission layer and including a compound represented by the following Formula 1, and

a third layer between the first layer and the second layer, the third layer includes a compound represented by the following Formula 2:

wherein, in Formula 1,

Ar 5 to Ar 8 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms,

adjacent Ar 7 s can be combined to form a ring, and adjacent Ar 8 s can be combined to form a ring,

each m is independently an integer of 0 to 4, and

L 2 and L 3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms,

wherein, in Formula 2,

Ar 1 , Ar 2 , and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms,

Ar 4 is a substituted or unsubstitute aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and

L 1 is a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms.

8. The organic EL device as claimed in claim 7 , wherein the emission layer includes an anthracene-containing compound represented by the following Formula 3:

wherein, in Formula 3,

each Ar 9 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50ring carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and

n is an integer of 1 to 10.

9. The organic EL device as claimed in claim 7 , wherein the second layer includes one of the following Compounds 1 to 22:

10. The organic EL device as claimed in claim 9 , wherein the third layer includes one of the following Compounds 23 to 38:

11. The organic EL device as claimed in claim 8 , wherein the anthracene-containing compound includes one of the following Compounds a-1 to a-12:

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE NAME OF ASSIGNEE PREVIOUSLY RECORDED ON REEL 035541 FRAME 0474. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jul 27, 2015
From: ITOI, HIROAKI
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 036190/0662 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2015
From: ITOI, HIROAKI
To: SAMSUNG DISPLAY CO., LT.D
Reel/Frame 035541/0474 →
Priority Claims (2)
JP 2014-183625 · Sep 9, 2014 · national
JP 2014-183626 · Sep 9, 2014 · national
Continuity (1)
Related Publication 20160079542A1 · Mar 17, 2016