IP Library Granted Patent US 9,365,767
Granted Patent B2
US 9,365,767 · App. 11/816,672 · Granted Jun 14, 2016

Organic electric field light emitting element and production therefor

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Quick Facts
Patent No.
US 9,365,767
App. No.
11/816,672
Granted
Jun 14, 2016
Kind
B2
Abstract

A composition for an organic electroluminescent device is a composition for forming an organic light emitting layer of an organic electroluminescent device by wet coating process. The composition contains a phosphorescent material, a charge transport material, and a solvent, in which the phosphorescent material and the charge transport material are each an unpolymerized organic compound, and the first oxidation potential of the phosphorescent material E D + , the first reduction potential of the phosphorescent material E D − , the first oxidation potential of the charge transporting material E T + , and the first reduction potential of the charge transporting material E T − satisfy the following condition: E T − +0.1≦E D − <E T + ≦E D + −0.1 or E D − +0.1≦E T − <E D + ≦E T + −0.1.

Claims (51)

1. A composition for an organic electroluminescent device, comprising a phosphorescent material, a charge transport material, and a solvent,

wherein each of the phosphorescent material and the charge transport material is independently an unpolymerized organic compound,

wherein at least one of the phosphorescent material and the charge transport material comprises two or more different materials,

wherein the first oxidation potential of the phosphorescent material E D+ ,

the first reduction potential of the phosphorescent material E D− ,

the first oxidation potential of the charge transport material E T+ , and

the first reduction potential of the charge transport material E T−

satisfy the following condition:

E D − +0.1≦ E T − <E D + ≦E T + −0.1,

wherein when the composition contains two or more different charge transport materials, the first oxidation potential of the charge transport material E T+ refers to the first oxidation potential of a charge transport material which has the smallest first oxidation potential, and the first reduction potential of the charge transport material E T− refers to the first reduction potential of a charge transport material which has the largest first reduction potential,

wherein when the composition contains two or more different phosphorescent materials, the first oxidation potential of the phosphorescent material E D+ refers to the first oxidation potential of a phosphorescent material which has the smallest first oxidation potential, and the first reduction potential of the phosphorescent material E D− refers to the first reduction potential of a phosphorescent material which has the largest first reduction potential,

wherein the phosphorescent material or each of the two or more different phosphorescent materials is represented by the following Formulae (4a), (4b), or (4c):

wherein each of Rings Q1 and Q1′ are independently a phenyl group which can be optionally substituted,

wherein Ring Q2 and Ring Q2′ are each independently a pyridyl group which can be optionally substituted,

wherein Ring Q2, Ring Q2′, or both are optionally substituted,

wherein each of M a , M b , and M c are iridium, and

wherein each q a , q b , and q c represents the valency of the metal M a , M b , and M c , respectively,

wherein the charge transport material or each of the two or more different charge transport materials is an organic compound represented by the following formula:

(A) n -Z,

wherein “A” represents an aromatic hydrocarbon group having from 6 to 30 carbon atoms, or an aromatic heterocyclic group having from 1 to 29 carbon atoms,

“n” is an integer from 2 to 6;

“Z” is an aromatic hydrocarbon group having from 6 to 20 carbon atoms, an aromatic heterocyclic group having from 3 to 19 carbon atoms, or an amino group substituted with an alkyl group having from 1 to 36 carbon atoms or an aromatic hydrocarbon group having from 6 to 36 carbon atoms;

wherein plural “A”s may be the same or different from each other,

wherein a molecular weight of “A” is 2000 or less, and

wherein a molecular weight of “Z” is 2000 or less,

“A” and “Z” may each further be substituted with a linear or branched alkyl group having from 1 to 12 carbon atoms, an aromatic hydrocarbon group having from 6 to 14 carbon atoms, or an aromatic heterocyclic group having from 3 to 13 carbon atoms,

wherein a molecular weight of the phosphorescent material is from 400 to 3000,

wherein a molecular weight of the charge transport material is from 500 to 3000, and

wherein the first oxidation potential and the first reduction potential are determined by cyclic voltammetry, wherein a tested material is dissolved in an organic solvent containing 0.1 mol/L of a supporting electrolyte to yield a 0.1 to 2 mM solution, oxygen is removed from the solution by bubbling of dry nitrogen, degassing under reduced pressure, or application of ultrasound, the solution in an electrically neutral state is subjected to electrolytic oxidation or reduction using a working electrode and a counter electrode at a sweep rate of 100 mV/sec, the potential of a first peak detected in the electrolytic oxidation or reduction is compared with the oxidation/reduction potential of a reference material, thereby determining the oxidation or reduction potential of the tested material, and the oxidation or reduction potential thus determined is further converted into a value versus saturated calomel electrode (SCE) as the reference electrode, and the converted value is defined as the first oxidation or reduction potential.

2. The composition for an organic electroluminescent device according to claim 1 , wherein each of the phosphorescent material and the charge transport material independently has a molecular weight of 100 to 10000.

3. The composition for an organic electroluminescent device according to claim 1 , wherein the composition has a water content of 1 percent by weight or less.

4. A thin film for an organic electroluminescent device formed from the composition for an organic electroluminescent device of claim 1 by a wet coating process.

5. The thin film for an organic electroluminescent device according to claim 4 , wherein the thin film has a refractive index of 1.78 or less with respect to light having a wavelength of 500 nm to 600 nm.

6. A transfer member for a thin film for an organic electroluminescent device, comprising a base material and a thin film arranged on the base material, wherein the thin film is formed from the composition for an organic electroluminescent device of claim 1 by a wet coating process.

7. An organic electroluminescent device comprising a substrate bearing an anode, a cathode, and an organic light emitting layer arranged between the two electrodes, wherein the organic light emitting layer is a layer formed by using the transfer member for a thin film for an organic electroluminescent device of claim 6 .

8. An organic electroluminescent device comprising a substrate bearing an anode, a cathode, and an organic light emitting layer arranged between the anode and cathode, wherein the organic light emitting layer is a layer formed from the composition for an organic electroluminescent device of claim 1 by a wet coating process.

9. The organic electroluminescent device according to claim 7 , further comprising a hole injection layer between the organic light emitting layer and the anode.

10. The organic electroluminescent device according to claim 8 , further comprising a hole injection layer between the organic light emitting layer and the anode.

11. The organic electroluminescent device according to claim 7 , further comprising an electron injection layer between the organic light emitting layer and the cathode.

12. The organic electroluminescent device according to claim 8 , further comprising an electron injection layer between the organic light emitting layer and the cathode.

13. A method of manufacturing an organic electroluminescent device, wherein the device comprises a substrate bearing an anode, a cathode, and an organic light emitting layer arranged between the anode and cathode, the method comprising forming the organic light emitting layer by a wet coating process using the composition for an organic electroluminescent device of claim 1 .

14. A composition for an organic electroluminescent device, comprising a phosphorescent material, a charge transport material, and a solvent,

wherein each of the phosphorescent material and the charge transport material is independently an unpolymerized organic compound, and

wherein the first oxidation potential of the phosphorescent material ED + ,

the first reduction potential of the phosphorescent material ED − ,

the first oxidation potential of the charge transport material ET + , and

the first reduction potential of the charge transport material ET −

satisfy the following condition:

E D − +0.1≦ E T − <E D + ≦E T + −0.1

wherein the phosphorescent material is represented by at least one formula selected from the group consisting of (D1), (D2), and (D3), and the charge transporting material is represented by at least one formula selected from the group consisting of (T1) to (T8):

wherein the first oxidation potential and the first reduction potential are determined by cyclic voltammetry, wherein a tested material is dissolved in an organic solvent containing 0.1 mol/L of a supporting electrolyte to yield a 0.1 to 2 mM solution, oxygen is removed from the solution by bubbling of dry nitrogen, degassing under reduced pressure, or application of ultrasound, the solution in an electrically neutral state is subjected to electrolytic oxidation or reduction using a working electrode and a counter electrode at a sweep rate of 100 mV/sec, the potential of a first peak detected in the electrolytic oxidation or reduction is compared with the oxidation/reduction potential of a reference material, thereby determining the oxidation or reduction potential of the tested material, and the oxidation or reduction potential thus determined is further converted into a value versus saturated calomel electrode (SCE) as the reference electrode, and the converted value is defined as the first oxidation or reduction potential.

Assignments (3)
CHANGE OF NAME Recorded Sep 5, 2017
From: MITSUBISHI RAYON CO., LTD.
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 043750/0834 →
MERGER Recorded Sep 4, 2017
From: MITSUBISHI CHEMICAL CORPORATION
To: MITSUBISHI RAYON CO., LTD.
Reel/Frame 043750/0207 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 20, 2007
From: YABE, MASAYOSHI; OGATA, TOMOYUKI; SATO, HIDEKI; IIDA, KOICHIRO; TANAKA, ASATO; TANAMURA, MITSURU; KAWAMURA, YUICHIRO; ISHIKAWA, HIRONORI; OKABE, KAZUKI
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 019717/0617 →