IP Library Granted Patent US 8,273,467
Granted Patent B2
US 8,273,467 · App. 11/711,689 · Granted Sep 25, 2012

Organic electroluminescent device

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Quick Facts
Patent No.
US 8,273,467
App. No.
11/711,689
Granted
Sep 25, 2012
Kind
B2
Abstract

An organic electroluminescent device, which comprises: a pair of electrodes; and an organic compound layer including a light-emitting layer between the pair of electrodes, wherein the organic compound layer comprises a compound represented by formula (I): wherein Z 1 , Z 2 , Z 3 and Z 4 each independently represents an atom selected from the group consisting of carbon, nitrogen, sulfur and oxygen and necessary for forming an unsaturated 6 -membered ring skeleton, the atom may have a hydrogen atom or a substituent; a bond in the unsaturated 6 -membered ring indicates a single bond or a double bond; and R 1 represents a substituent.

Claims (50)

1. An organic electroluminescent device, which comprises:

a pair of electrodes; and

an organic compound layer including a light-emitting layer between the pair of electrodes,

wherein the organic compound layer comprises a compound represented by formula (III):

wherein R 3 , R 5 , R 8 and R 13 each represents a hydrogen atom;

R 4 represents a hydrogen atom, a phenyl group, a substituted phenyl group, an alkyl group, or a substituted alkyl group;

R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 14 and R 15 each independently represents a hydrogen atom or a substituent, when R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 14 and R 15 each represents a substituent, the substituent may further have a substituent; and

pairs of R 6 and R 7 , R 9 and R 10 , R 11 and R 12 , and R 14 and R 15 , each may combine to form a ring, wherein the compound represented by formula (III) has the lowest excited triplet energy level of from 65 kcal/mol (272.35 kJ/mol) to 95 kcal/mol (398.05 kJ/mol) and has a glass transition temperature of from 110 to 400° C.

2. The organic electroluminescent device according to claim 1 ,

wherein formula (III) is represented by formula (IV):

Formula (IV):

wherein R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 and R 25 each independently represents a hydrogen atom or a substituent, when R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 and R 25 each represents a substituent, the substituent may further have a substituent; and

pairs of R 14 and R 16 , R 7 and R 25 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 and R 20 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , and R 24 and R 25 , each may combine to form a ring;

R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 have the same meanings as R 3 , R 4 , R 5 , R 7 , R 9 , R 9 and R 10 in formula (III); and

R 11 , R 12 , R 13 and R 14 have the same meanings as R 11 , R 12 , R 13 and R 14 in formula (III).

3. The organic electroluminescent device according to claim 1 , wherein formula (III) is represented by formula (V):

Formula (V):

wherein R 26 , R 28 , R 29 , R 30 , R 31 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 and R 43 each independently represents a hydrogen atom or a substituent, when R 26 , R 28 , R 29 , R 30 , R 31 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 and R 43 each represents a substituent, the substituent may further have a substituent, provided that pairs of R 26 and R 43 , R 26 and R 39 , R 28 and R 29 , R 30 and R 31 , R 33 and R 34 , R 33 and R 38 , R 34 and R 35 , R 35 and R 36 , R 36 and R 37 , R 37 and R 38 , R 39 and R 40 , R 40 and R 41 , R 41 and R 42 , and R 42 and R 43 , each does not combine to form a condensed ring; R 27 and R 32 each represents a hydrogen atom; and R 4 has the same meanings as R 4 in formula (III).

4. The organic electroluminescent device according to claim 1 ,

wherein formula (III) is represented by formula (VI):

wherein R 44 , R 45 , R 48 and R 49 each independently represents a hydrogen atom or a substituent, when R 44 , R 45 , R 48 and R 49 each represents a substituent, the substituent may further have a substituent;

pairs of R 44 and R 45 , and R 48 and R 49 , each may combine to form a ring;

R 46 and R 47 each independently represents a hydrogen atom or a substituent, when R 46 and R 47 each represents a substituent, the substituent may further have a substituent, provided that when R 28 , R 29 , R 30 , R 31 , R 46 and R 47 each represents a substituent, pairs of R 44 and R 46 , R 45 and R 46 , R 47 and R 48 , and R 47 and R 49 , each does not combine to form a condensed ring;

R 4 has the same meanings as R 4 in formula (III);

R 27 and R 32 each represents a hydrogen atom; and

R 28 , R 29 , R 30 and R 31 each independently represents a hydrogen atom or a substituent, when R 28 , R 29 , R 30 and R 31 each represents a substituent, the substituent may further have a substituent, but pairs of R 28 and R 29 , and R 30 and R 31 , each does not combine to form a condensed ring.

5. The organic electroluminescent device according to claim 1 ,

wherein the light-emitting layer comprises at least one kind of a triplet-emission material.

6. The organic electroluminescent device according to claim 5 ,

wherein the at least one kind of triplet-emission material is a platinum complex or an iridium complex.

7. The organic electroluminescent device according to claim 6 ,

wherein the at least one kind of triplet-emission material is a platinum complex.

8. The organic electroluminescent device according to claim 1 ,

wherein a layer comprising the compound represented by formula (III) is adjacent to a layer comprising an oxide containing at least one of an alkaline metal and an alkaline earth metal.

9. The organic electroluminescent device according to claim 1 ,

wherein a layer comprising the compound represented by formula (III) is adjacent to a layer comprising at least one of an alkaline metal and an alkaline earth metal.

10. The organic electroluminescent device according to claim 1 ,

wherein a layer comprising the compound represented by formula (III) is adjacent to a layer comprising a halide containing at least one of an alkaline metal and an alkaline earth metal.

11. The organic electroluminescent device according to claim 1 ,

wherein the substituent and the further substituent are independently selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, a halogen atom, a cyano group, a heterocyclic group, and a nitro group.

12. The organic electroluminescent device according to claim 1 ,

wherein each of R 3 , R 4 , and R 5 is a hydrogen atom.

13. A compound represented by formula (V):

Formula (V):

wherein R 26 , R 28 , R 29 , R 30 , R 31 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 and R 43 each independently represents a hydrogen atom or a substituent, when R 26 , R 28 , R 29 , R 30 , R 31 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 and R 43 each represents a substituent, the substituent may further have a substituent, provided that pairs of R 26 and R 43 , R 26 and R 39 , R 28 and R 29 , R 30 and R 31 , R 33 and R 34 , R 33 and R 38 , R 34 and R 35 , R 35 and R 36 , R 36 and R 37 , R 37 and R 38 , R 39 and R 40 , R 40 and R 41 , R 41 and R 42 , and R 42 and R 43 , each does not combine to form a condensed ring; R 27 and R 32 each represents a hydrogen atom; and R 4 has the same meanings as R 4 in formula (III).

14. A compound represented by formula (VI):

wherein R 44 , R 45 , R 48 and R 49 each independently represents a hydrogen atom or a substituent, when R 44 , R 45 , R 48 and R 49 each represents a substituent, the substituent may further have a substituent; and

pairs of R 44 and R 45 , and R 48 and R 49 , each may combine to form a ring;

R 46 and R 47 each independently represents a hydrogen atom or a substituent, when R 46 and R 47 each represents a substituent, the substituent may further have a substituent, provided that when R 28 , R 29 , R 30 , R 31 , R 46 and R 47 each represents a substituent, pairs of R 44 and R 46 , R 45 and R 46 , R 47 and R 48 , and R 47 and R 49 , each does not combine to form a condensed ring; and R 4 represents a hydrogen atom or a substituent; and

R 28 , R 29 , R 30 , and R 31 each independently represents a hydrogen atom or a substituent, when R 28 , R 29 , R 30 , and R 31 represents a substituent, the substituent may further have a substituent, but pairs of R 28 and R 29 , R 30 and R 31 each does not combine to form a condensed ring; and R 27 and R 32 each represents a hydrogen atom.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 1, 2012
From: FUJIFILM CORPORATION
To: UDC IRELAND LIMITED
Reel/Frame 028889/0636 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 28, 2007
From: SANO, SATOSHI; IGARASHI, TATSUYA; KINOSHITA, MASARU
To: FUJIFILM CORPORATION
Reel/Frame 018995/0948 →