IP Library Granted Patent US 10,411,212
Granted Patent B2
US 10,411,212 · App. 14/349,626 · Granted Sep 10, 2019

Organic electroluminescent element

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,411,212
App. No.
14/349,626
Granted
Sep 10, 2019
Kind
B2
Abstract

An organic electroluminescence device including: an anode; a cathode; two or more emitting units that are disposed between the anode and the cathode, each unit having an emitting layer; and a charge-generating layer that is disposed between the emitting units, wherein the charge-generating layer comprises an N layer nearer to the anode and a P layer nearer to the cathode, and the P layer comprises a compound represented by the following formula (I).

Claims (55)

1. A substrate comprising two or more adjacent organic electroluminescence devices, each organic electroluminescence device comprising:

an anode;

a cathode;

two or more emitting units that are disposed between the anode and the cathode, each unit having an emitting layer; and

a charge-generating layer that is disposed between the emitting units,

wherein the charge-generating layer comprises an N layer nearer to the anode and a P layer nearer to the cathode, and

the P layer comprises a compound represented by the following formula (I):

wherein in the formula (I),

Ar 1 is an aromatic ring including 6 to 24 ring carbon atoms, or a heterocyclic ring including 5 to 24 ring atoms, and

Rg 1 and Rg 2 may be the same or different from each other and are represented by the following formula (i) or (ii):

wherein X 1 and X 2 may be the same or different from each other and are represented by any one of divalent groups represented by the following (a) to (g):

wherein R 21 to R 24 may be the same or different from each other, and are a hydrogen atom, a substituted or unsubstituted fluoroalkyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, and R 22 and R 23 may be bonded to each other to form a ring;

R 1 to R 4 may be the same or different from each other, and a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a halogen atom, a substituted or unsubstituted fluoroalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted fluoroalkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, or a cyano group;

R 1 and R 2 may be bonded to each other to form a ring and R 3 and R 4 may be bonded to each other to form a ring; and

Y 1 to Y 4 may be the same or different from each other, and are —N═, —CH═, or C(R 5 )═, R 5 is the same as R 1 to R 4 , and adjacent groups of R 1 to R 5 may be bonded to each other to form a ring,

wherein the charge-generating layer are common among the organic electroluminescence device, and

each organic electroluminescence device comprises a color filter.

2. The substrate according to claim 1 , wherein at least one of the emitting units comprises a hole-transporting layer, and the P layer of the charge-generating layer is contacted with the hole-transporting layer.

3. The substrate according to claim 1 , wherein the N layer of the charge-generating layer comprises at least one selected from the group consisting of an electron-donating metal, an electron-donating metal compound and an electron-donating metal complex.

4. The substrate according to claim 3 , wherein the N layer of the charge-generating layer comprises at least one selected from the group consisting_of an alkali metal, an alkali metal compound, an alkali metal-containing organic metal complex, an alkaline-earth metal, an alkaline-earth metal compound, an alkaline-earth metal-containing organic metal complex, a rare-earth metal, a rare-earth metal compound and a rare-earth metal-containing organic metal complex.

5. The substrate according to claim 1 , wherein the N layer of the charge-generating layer comprises a nitrogen-containing heterocyclic compound.

6. The substrate according to claim 5 , wherein the nitrogen-containing heterocyclic compound is represented by the following formula (9):

wherein, A 14 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon group including 6 to 60 carbon atoms that comprises a polycyclic aromatic hydrocarbon group formed by 3 to 40 aromatic rings being fused, or a nitrogen-containing heterocyclic group,

B is a single bond, or a substituted or unsubstituted aromatic ring group,

R 31 and R 32 are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 60 carbon atoms, a substituted or unsubstituted nitrogen-containing heterocyclic group, or a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms.

7. The substrate according to claim 1 , wherein a material constituting the emitting layer(s) of at least one of the emitting units is different from a material constituting the emitting layer(s) of other emitting unit(s).

8. The substrate_according to claim 1 , wherein at least one of the emitting units comprises a hole-transporting region, and the P layer of the charge-generating region is contacted with the hole-transporting region.

9. The substrate according to claim 8 , wherein the hole-transporting region comprises an aromatic amine derivative represented by the following formula (4):

wherein Ar 31 to Ar 34 are an aromatic hydrocarbon group including 6 to 50 ring carbon atoms that may have a substituent, a fused aromatic hydrocarbon group including 6 to 50 ring carbon atoms that may have a substituent, an aromatic heterocyclic group including 2 to 40 ring carbon atoms that may have a substituent, a fused aromatic heterocyclic group including 2 to 40 ring carbon atoms that may have a substituent, a group formed by bonding of the aromatic hydrocarbon group with the aromatic heterocyclic group, a group formed by bonding of the aromatic hydrocarbon group with the fused aromatic heterocyclic group, a group formed by bonding of the fused aromatic hydrocarbon group with the aromatic heterocyclic group, or a group formed by bonding of the fused aromatic hydrocarbon group with the fused aromatic heterocyclic group; and

L is a single bond, an aromatic hydrocarbon group including 6 to 50 ring carbon atoms that may have a substituent, a fused aromatic hydrocarbon group including 6 to 50 ring carbon atoms that may have a substituent, an aromatic heterocyclic group including 2 to 40 ring carbon atoms that may have a substituent, a fused aromatic heterocyclic group including 2 to 40 ring carbon atoms that may have a substituent, a group formed by bonding of the aromatic hydrocarbon group with the aromatic heterocyclic group, a group formed by bonding of the aromatic hydrocarbon group with the fused aromatic heterocyclic group, a group formed by bonding of the fused aromatic hydrocarbon group with the aromatic heterocyclic group, or a. group formed by bonding of the fused aromatic hydrocarbon group with the fused aromatic heterocyclic group.

10. The substrate according to claim 8 , wherein the hole-transporting region comprises an aromatic amine derivative represented by the following formula (5):

wherein Ar 31 to Ar 33 are an aromatic hydrocarbon group including 6 to 50 ring carbon atoms that may have a substituent, a fused aromatic hydrocarbon group including 6 to 50 ring carbon atoms that may have a substituent, an aromatic heterocyclic group including 2 to 40 ring carbon atoms that may have a substituent, a fused aromatic heterocyclic group including 2 to 40 ring carbon atoms that may have a substituent, a group formed by bonding of the aromatic hydrocarbon group with the aromatic heterocyclic group, a group formed by bonding of the aromatic hydrocarbon group with the fused aromatic heterocyclic group, a group formed by bonding of the fused aromatic hydrocarbon group with the aromatic heterocyclic group, or a group formed by bonding of the fused aromatic hydrocarbon group with the fused aromatic heterocyclic group.

11. The substrate according to claim I, wherein the compound represented by the formula (I) is a compound represented by the following formula (I-A) or (I-B):

wherein in the formula (I-A), Ar 1 , X 1 , X 2 , R 1 to R 4 , and Y 1 to Y 4 are the same as Ar 1 , X 1 , X 2 , R 1 to R 4 , and Y 1 to Y 4 in the formula (I): and

in the formula (I-B) Ar 2 is the same as Ar 1 in the formula (I), X 3 and X 4 are the same as X 1 and X 2 in the formula (I), Y 5 to Y 8 are the same as Y 1 to Y 4 in the formula (I) and R 1 to R 4 are the same as R 1 to R 4 in the formula (I).

12. The substrate according to claim 1 , wherein the compound represented by the formula (I) is a compound represented by any one of the following formulas (II) to (X):

wherein X 1 , X 2 and R 1 to R 4 are the same as X 1 , X 2 and R 1 to R 4 in the formula (I): and Y 21 to Y 26 , Y 31 to Y 38 and Y 41 to Y 50 are the same as Y 1 to Y 4 in the formula (I).

13. The substrate according to claim 1 , wherein the compound represented by the formula (I) is a compound represented by any one of the following formulas (I-a) to (I-r):

wherein R 31 to R 52 are the same as R 1 to R 4 in the formula (I) and adjacent two of R 31 to R 52 may be bonded to each other to form a ring.

14. The substrate according to claim 1 , wherein the P layer of the charge-generating layer consists of the compound represented by the formula (I).

15. The substrate according to claim 1 , wherein in the formula (I), Ar 1 is a benzene ring, a pyrazine ring, or a pyridine ring.

16. The substrate according to claim 15 , wherein R 1 and R 2 are not bonded to each other to form a ring, R 3 and R 4 are not bonded to each other to form a ring, and adjacent groups of R 1 to R 5 are not bonded to each other to form a ring.

17. The substrate according to claim 16 , wherein R 1 to R 4 may be the same or different from each other, and a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a halogen atom, a substituted or unsubstituted fluoroalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted fluoroalkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, or a cyano group.

18. The substrate of claim 1 , wherein the anode of each organic electroluminescence device is a stripe shape.

19. The substrate of claim 1 , wherein in the compound of formula (1)

Y 1 to Y 4 are —CH═;

and

at least one of R 1 and R 2 and at least one or R 3 and R 4 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted fluoroalkoxy group.

20. The substrate of claim 19 , wherein the emitting layer disposed nearer to the cathode is a blue emitting layer comprising:

an anthracene derivative represented by the following formula (1):

wherein Ar 11 and Ar 12 are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group including 5 to 30 ring atoms; and

R 101 to R 108 are independently a halogen atom, a fluorine atom, a substituted or unsubstituted alkyl group including 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group including 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group including 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group including 5 to 30 ring atoms, and

a fused polycyclic amine derivative represented by the following formula (2)

wherein Y is a substituted or unsubstituted fused aryl group including 10 to 50 ring carbon atoms, and

Ar 21 and Ar 22 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 8, 2025
From: JOLED INC.
To: JDI DESIGN AND DEVELOPMENT G.K.
Reel/Frame 071059/0449 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 7, 2017
From: SONY CORPORATION
To: JOLED INC.
Reel/Frame 043477/0926 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 23, 2014
From: KAMBE, EMIKO; NAKAMURA, MASATO; ENDO, JUN; FUNAHASHI, MASAKAZU; MORISHITA, HIRONOBU
To: SONY CORPORATION; IDEMITSU KOSAN CO., LTD.
Reel/Frame 032738/0338 →
Cited By (1)
US 12,701,890