JPH1174080A - Organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a luminous element excellent in luminous efficiency, and luminous in high luminance, by nipping at least one layer, containing at least one kind of a 11H-pyrid[2.1-b]quinazoline-11-on derivative, between a pair of electrodes. SOLUTION: A 11H-pyrid[2.1-b]quinazoline-11 on derivative, being contained in a luminous element, is preferably a compound expressed in a formula. In the formula, X1-X8 are independently expressing respectively hydrogen and halogen atoms, alkyl and alkoxy groups having straight chainlike and branched or ringlike states, and aralkyl and aryl or aryloxy groups substitutional or unsubstitutive; and moreover, adjoining groups, selected from X1 and X2, X2 and X3, X3 and X4, X5 and X6, X6 and X7, and X7 and X8, together with carbon atoms, joined with each other and substituted, may form a carbocyclic aliphatic ring, substitutive or unsubstitutive, or a carbocyclic aromatic ring, substitutive or unsubstitutive.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to an organic electroluminescent device.

[0002]

2. Description of the Related Art Conventionally, an inorganic electroluminescent element has been used as a panel-type light source such as a backlight. However, driving the light emitting element requires a high AC voltage. Recently, an organic electroluminescent device (organic electroluminescent device: organic EL device) using an organic material as a light emitting material has been developed [Appl. Phys. Lett., 51 ,
913 (1987)]. The organic electroluminescent element has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode,
An exciton is generated by injecting electrons and holes into the thin film and recombining them, and emits light using light emitted when the exciton is deactivated. is there. The organic electroluminescent element can emit light at a low DC voltage of about several volts to several tens of volts, and various colors (for example, red, blue, and green) can be obtained by selecting the type of the fluorescent organic compound. ) Is possible. Organic electroluminescent devices having such features include various light emitting devices,
Application to display elements and the like is expected. However,
Generally, the light emission luminance is low and is not practically sufficient.

As a method for improving light emission luminance, an organic electroluminescent device using, for example, tris (8-quinolinolato) aluminum as a host compound, a coumarin derivative, or a pyran derivative as a guest compound (dopant) has been proposed as a light emitting layer. (J. Appl. Phys., 65 , 3610
(1989)]. Further, bis (2-methyl-
An organic electroluminescent device using 8-quinolinolate) (4-phenylphenolate) aluminum as a host compound and an acridone derivative (for example, N-methyl-2-methoxyacridone) as a guest compound has been proposed (Japanese Patent Application Laid-Open No. Hei 8 (1999)). -67873). However, it is difficult to say that these light emitting elements also have sufficient light emission luminance. Further, an organic electroluminescent device using an acridone derivative (for example, N-methyl-2-methoxyacridone) for an electron injection / transport layer has been proposed (Japanese Patent Application Laid-Open No. H8-6787).
No. 3), the adhesion between the layer containing the acridone derivative and an electrode (for example, a cathode) is poor, and it has been found that improvement is necessary for long-term use. At present, an organic electroluminescent device that emits light with higher luminance is desired.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic electroluminescent device which is excellent in luminous efficiency and emits light with high luminance.

[0005]

Means for Solving the Problems The present inventors have made intensive studies on the organic electroluminescent device, and as a result, completed the present invention. That is, the present invention provides an organic electroluminescent device comprising at least one layer containing at least one 11H-pyrido [2,1-b] quinazolin-11-one derivative between a pair of electrodes. The organic electroluminescent device according to the above, wherein the layer containing the [2,1-b] quinazolin-11-one derivative is a light-emitting layer, and a layer containing the 11H-pyrido [2,1-b] quinazolin-11-one derivative. Is a light-emitting layer, wherein the layer containing the 11H-pyrido [2,1-b] quinazolin-11-one derivative has a polycyclic aromatic compound, a light-emitting organic metal complex or a triarylamine. The organic electroluminescent device according to any one of the above-mentioned, which contains a derivative, between a pair of electrodes, further, the organic electroluminescent device according to any one of the above-mentioned, which has a hole injection transport layer, between the pair of electrodes. And the electron injection transport layer The organic electroluminescent device according to any one of the above, wherein the 11H-pyrido [2,1-b] quinazolin-11-one derivative is a compound represented by the general formula (1). An organic electroluminescent device according to any one of the above.

[0006]

Embedded image (Wherein X _{1 to} X ₈ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aralkyl group, It represents a unsubstituted aryl group or a substituted or unsubstituted aryloxy group, further, X ₁
And X ₂ , X ₂ and X ₃ , X ₃ and X ₄ , X ₅ and X ₆ , X ₆ and X ₇ , and X ₇ and X ₈ are mutually bonded and substituted. Together with the carbon atom, it may form a substituted or unsubstituted carbocyclic aliphatic ring or a substituted or unsubstituted carbocyclic aromatic ring)

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The organic electroluminescent device of the present invention, between a pair of electrodes,
It comprises at least one layer containing at least one 11H-pyrido [2,1-b] quinazolin-11-one derivative. 11H-pyrido [2,1-b] according to the present invention
The quinazolin-11-one derivative (hereinafter abbreviated as compound A according to the present invention) is preferably a compound represented by general formula (1) (formula 3).

[0008]

Embedded image (Wherein X _{1 to} X ₈ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aralkyl group, It represents a unsubstituted aryl group or a substituted or unsubstituted aryloxy group, further, X ₁
And X ₂ , X ₂ and X ₃ , X ₃ and X ₄ , X ₅ and X ₆ , X ₆ and X ₇ , and X ₇ and X ₈ are mutually bonded and substituted. Together with the carbon atom, it may form a substituted or unsubstituted carbocyclic aliphatic ring or a substituted or unsubstituted carbocyclic aromatic ring)

In the compound represented by the general formula (1),
X _{1 to} X ₈ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aralkyl group,
Represents a substituted or unsubstituted aryl group or a substituted or unsubstituted aryloxy group, and furthermore, X ₁ and X ₂ ,
Adjacent groups selected from X ₂ and X ₃ , X ₃ and X ₄ , X ₅ and X ₆ , X ₆ and X ₇ , and X ₇ and X ₈ are bonded to each other to form, together with a substituting carbon atom, It represents that a substituted or unsubstituted carbocyclic aliphatic ring or a substituted or unsubstituted carbocyclic aromatic ring may be formed. Note that the aryl group represents a carbocyclic aromatic group such as a phenyl group and a naphthyl group, for example, a heterocyclic aromatic group such as a furyl group, a thienyl group, and a pyridyl group.

Preferably, X _{1 to} X ₈ are a hydrogen atom; a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom); a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms (for example, methyl Group, ethyl group, n-propyl group,
Isopropyl group, n-butyl group, isobutyl group, sec-
Butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, n-hexyl, 3,3-dimethylbutyl, cyclohexyl, n-heptyl, cyclohexylmethyl Group, n-octyl group, tert-octyl group, 2-
Ethylhexyl group, n-nonyl group, n-decyl group, n-
Dodecyl group, n-tetradecyl group, n-hexadecyl group, etc.);

A linear, branched or cyclic alkoxy group having 1 to 16 carbon atoms (for example, methoxy, ethoxy, n-
Propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, cyclopentyloxy group,
n-hexyloxy group, 3,3-dimethylbutyloxy group, cyclohexyloxy group, n-heptyloxy group,
n-octyloxy group, 2-ethylhexyloxy group,
n-nonyloxy group, n-decyloxy group, n-dodecyloxy group, n-tetradecyloxy group, n-hexadecyloxy group, etc .; a substituted or unsubstituted aralkyl group having 5 to 16 carbon atoms (for example, benzyl group) , Phenethyl group,
α-methylbenzyl group, α, α-dimethylbenzyl group,
1-naphthylmethyl group, 2-naphthylmethyl group, furfuryl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 4-ethylbenzyl group, 4
-Isopropylbenzyl group, 4-tert-butylbenzyl group, 4-n-hexylbenzyl group, 4-n-nonylbenzyl group, 3,4-dimethylbenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 4 -Ethoxybenzyl group, 4-n-butoxybenzyl group, 4-fluorobenzyl group, 3-fluorobenzyl group, 2-chlorobenzyl group, 4-chlorobenzyl group, etc.);

A substituted or unsubstituted aryl group having 4 to 16 carbon atoms (for example, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl,
-Ethylphenyl group, 4-n-propylphenyl group, 4
-Isopropylphenyl group, 4-n-butylphenyl group, 4-tert-butylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-cyclohexylphenyl group, 4
-N-octylphenyl group, 4-n-decylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 5-indanyl Group, 1,2,3,4-
Tetrahydro-5-naphthyl group, 1,2,3,4-tetrahydro-6-naphthyl group, 2-methoxyphenyl group,
3-methoxyphenyl group, 4-methoxyphenyl group, 3
-Ethoxyphenyl group, 4-ethoxyphenyl group, 4-
n-propoxyphenyl group, 4-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-n-hexyloxyphenyl group, 4-cyclohexyloxyphenyl group, 4-n- Heptyloxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 2,3-dimethoxyphenyl group, 2,5-dimethoxyphenyl group,
3,4-dimethoxyphenyl group, 2-methoxy-5-methylphenyl group, 3-methyl-4-methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group ,
3-chlorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-trifluoromethylphenyl group,
3,4-dichlorophenyl group, 2-methyl-4-chlorophenyl group, 2-chloro-4-methylphenyl group, 3-
Chloro-4-methylphenyl group, 2-chloro-4-methoxyphenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 4- (4′-methylphenyl) phenyl group, 4- (4′-methoxyphenyl) ) Phenyl group, 1-
Naphthyl group, 2-naphthyl group, 4-ethoxy-1-naphthyl group, 6-methoxy-2-naphthyl group, 7-ethoxy-2-naphthyl group, 2-furyl group, 2-thienyl group, 3
-Thienyl group, 2-pyridyl group, 3-pyridyl group, 4-
A pyridyl group);

Alternatively, a substituted or unsubstituted aryloxy group having 4 to 16 carbon atoms (for example, phenyloxy group, 2
-Methylphenyloxy group, 3-methylphenyloxy group, 4-methylphenyloxy group, 4-ethylphenyloxy group, 4-n-propylphenyloxy group, 4-isopropylphenyloxy group, 4-n-butylphenyloxy Group, 4-tert-butylphenyloxy group, 4-isopentylphenyloxy group, 4-tert-pentylphenyloxy group, 4-n-hexylphenyloxy group,
-Cyclohexylphenyloxy group, 4-n-octylphenyloxy group, 4-n-decylphenyloxy group,
2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 5-indanyloxy group, 1,2,3,4 -Tetrahydro-5-naphthyloxy group, 1,2,3,4-tetrahydro-6-naphthyloxy group, 2-methoxyphenyloxy group, 3-
Methoxyphenyloxy group, 4-methoxyphenyloxy group, 3-ethoxyphenyloxy group, 4-ethoxyphenyloxy group, 4-n-propoxyphenyloxy group, 4-isopropoxyphenyloxy group, 4-n-butoxyphenyloxy Group, 4-n-pentyloxyphenyloxy group, 4-n-hexyloxyphenyloxy group, 4-cyclohexyloxyphenyloxy group, 4-
n-heptyloxyphenyloxy group, 4-n-octyloxyphenyloxy group, 4-n-decyloxyphenyloxy group, 2,3-dimethoxyphenyloxy group,
2,5-dimethoxyphenyloxy group, 3,4-dimethoxyphenyloxy group, 2-methoxy-5-methylphenyloxy group, 3-methyl-4-methoxyphenyloxy group, 2-fluorophenyloxy group, 3-fluoro Phenyloxy group, 4-fluorophenyloxy group, 2-
Chlorophenyloxy group, 3-chlorophenyloxy group, 4-chlorophenyloxy group, 4-bromophenyloxy group, 4-trifluoromethylphenyloxy group,
3,4-dichlorophenyloxy group, 2-methyl-4-
Chlorophenyloxy group, 2-chloro-4-methylphenyloxy group, 3-chloro-4-methylphenyloxy group, 2-chloro-4-methoxyphenyloxy group, 4-
Phenylphenyloxy group, 3-phenylphenyloxy group, 4- (4′-methylphenyl) phenyloxy group, 4- (4′-methoxyphenyl) phenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4
-Ethoxy-1-naphthyloxy group, 6-methoxy-2
-Naphthyloxy group, 7-ethoxy-2-naphthyloxy group, 2-furyloxy group, 2-thienyloxy group, 3
-Thienyloxy group, 2-pyridyloxy group, 3-pyridyloxy group, 4-pyridyloxy group, etc.).

More preferably, a hydrogen atom, a fluorine atom,
Chlorine atom, alkyl group having 1 to 10 carbon atoms, 1 to 1 carbon atom
An alkoxy group having 0, an aralkyl group having 7 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aryloxy group having 6 to 10 carbon atoms, and more preferably a hydrogen atom, a fluorine atom, a chlorine atom, An alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, a carbocyclic aromatic group having 6 to 10 carbon atoms, or a carbocyclic aromatic group having 6 to 10 carbon atoms Group oxy group.

Adjacent groups selected from X ₁ and X ₂ , X ₂ and X ₃ , X ₃ and X ₄ , X ₅ and X ₆ , X ₆ and X ₇ , and X ₇ and X ₈ are bonded to each other. And, together with the substituted carbon atom, a substituted or unsubstituted carbocyclic aliphatic ring,
Alternatively, a substituted or unsubstituted carbocyclic aromatic ring may be formed, and preferably, a substituted or unsubstituted carbocyclic aliphatic ring having 5 to 10 carbon atoms in total, or 6 to 6 carbon atoms in total.
It may form 10 substituted or unsubstituted carbocyclic aromatic rings. Specific examples of a carbocyclic aliphatic ring or a carbocyclic aromatic ring include, for example, a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, a cyclooctene ring,
Examples thereof include a benzene ring and a naphthalene ring, and more preferred are a cyclohexene ring and a benzene ring.
Incidentally, the carbocyclic aliphatic ring, the carbocyclic aromatic ring may have a substituent, for example, may be monosubstituted or polysubstituted with the substituents described in X _{1 to} X ₈ , More preferably, it is an unsubstituted carbocyclic aliphatic ring or an unsubstituted carbocyclic aromatic ring.

Specific examples of the compound A according to the present invention include:
For example, the following compounds can be mentioned, but the present invention is not limited thereto. -Exemplified compound number 1. 11H-pyrido [2,1-b] quinazolin-11-one 2. 1-methyl-11H-pyrido [2,1-b] quinazolin-11-one 3. 2-n-dodecyl-11H-pyrido [2,1-b] quinazolin-11-one 4. 3-methyl-11H-pyrido [2,1-b] quinazolin-11-one 5. 3-tert-butyl-11H-pyrido [2,1-b] quinazolin-11-one 6. 4-n-hexyl-11H-pyrido [2,1-b] quinazolin-11-one 6. 6-methyl-11H-pyrido [2,1-b] quinazolin-11-one 8. 7-n-butyl-11H-pyrido [2,1-b] quinazolin-11-one 8. 8-Methyl-11H-pyrido [2,1-b] quinazolin-11-one 9. 9-Methyl-11H-pyrido [2,1-b] quinazolin-11-one 9. 9-ethyl-11H-pyrido [2,1-b] quinazolin-11-one 12. 3,8-dimethyl-11H-pyrido [2,1-b] quinazolin-11-one 13. 1-ethoxy-11H-pyrido [2,1-b] quinazolin-11-one 14. 2-methoxy-11H-pyrido [2,1-b] quinazolin-11-one 2-n-butoxy-11H-pyrido [2,1-b] quinazolin-11-one

[0017] 16. 16. 3-methoxy-11H-pyrido [2,1-b] quinazolin-11-one 17. 3-ethoxy-11H-pyrido [2,1-b] quinazolin-11-one 18. 3-n-pentyloxy-11H-pyrido [2,1-b] quinazolin-11-one 21. 3-n-tetradecyloxy-11H-pyrido [2,1-b] quinazolin-11-one 21. 4-cyclohexyloxy-11H-pyrido [2,1-b] quinazolin-11-one 21. 2-Methyl-8-methoxy-11H-pyrido [2,1-b] quinazolin-11-one 23. 3-Methoxy-9-methyl-11H-pyrido [2,1-b] quinazolin-11-one 21. 2-Bromo-11H-pyrido [2,1-b] quinazolin-11-one 25. 3-Fluoro-11H-pyrido [2,1-b] quinazolin-11-one 25. 3-Chloro-11H-pyrido [2,1-b] quinazolin-11-one 4-Chloro-11H-pyrido [2,1-b] quinazolin-11-one 27. 26. 6-Chloro-11H-pyrido [2,1-b] quinazolin-11-one 8-Fluoro-2-methyl-11H-pyrido [2,1-b] quinazolin-11-one 29. 30. 3-phenyl-11H-pyrido [2,1-b] quinazolin-11-one 3- (4'-methylphenyl) -11H-pyrido [2,1-b] quinazolin-11-one

31. 3- (4'-ethoxyphenyl) -11H-pyrido [2,1-b] quinazolin-11-one 32. 3- (4'-fluorophenyl) -11H-pyrido [2,1-b] quinazolin-11-one 33. 3- (2'-naphthyl) -11H-pyrido [2,1-b] quinazolin-11-one 34. 3- (3'-thienyl) -11H-pyrido [2,1-b] quinazolin-11-one 35. 3- (2'-furyl) -11H-pyrido [2,1-b] quinazolin-11-one 36. 37. 3- (4'-n-hexyloxyphenyl) -11H-pyrido [2,1-b] quinazolin-11-one 4- (3 ', 4'-dimethylphenyl) -11H-pyrido [2,1-b] quinazolin-11-one 38. 6- (4'-phenylphenyl) -11H-pyrido [2,1-b] quinazolin-11-one 39. 40. 7-phenyl-11H-pyrido [2,1-b] quinazolin-11-one 8- (3'-methylphenyl) -11H-pyrido [2,1-b] quinazolin-11-one 41. 2-benzyl-11H-pyrido [2,1-b] quinazolin-11-one 42. 3- (α, α-dimethylbenzyl) -11H-pyrido [2,1-b] quinazolin-11-one 43. 7- (4'-methylbenzyl) -11H-pyrido [2,1-b] quinazolin-11-one 44. 7- (α, α-dimethylbenzyl) -11H-pyrido [2,1-b] quinazolin-11-one 45. 8- (4'-chlorobenzyl) -11H-pyrido [2,1-b] quinazolin-11-one

46. 2-phenyloxy-11H-pyrido [2,1-b] quinazoline-11-one 47. 48. 2- (4'-methylphenyloxy) -11H-pyrido [2,1-b] quinazolin-11-one 3- (4'-methoxyphenyloxy) -11H-pyrido [2,1-b] quinazolin-11-one 49. 7- (4'-Fluorophenyloxy) -11H-pyrido [2,1-b] quinazolin-11-one 3,8-diphenyloxy-11H-pyrido [2,1-b] quinazolin-11-one 51. 2: 2-trimethylene-11H-pyrido [2,1-b] quinazolin-11-one 52. 1: 2-tetramethylene-11H-pyrido [2,1-b] quinazolin-11-one 53. 2: 3-tetramethylene-11H-pyrido [2,1-b] quinazolin-11-one 54. 8: 9-Tetramethylene-11H-pyrido [2,1-b] quinazolin-11-one 55. 2: 3-benzo-11H-pyrido [2,1-b] quinazolin-11-one 56. 3: 4-benzo-11H-pyrido [2,1-b] quinazolin-11-one 57. 6: 7-benzo-11H-pyrido [2,1-b] quinazolin-11-one 58. 7: 8-benzo-11H-pyrido [2,1-b] quinazolin-11-one 59. 8: 9-benzo-11H-pyrido [2,1-b] quinazolin-11-one 2: 3,7: 8-Dibenzo-11H-pyrido [2,1-b] quinazolin-11-one

The compound A according to the present invention can be produced according to a method known per se. For example, Synth. Com
m., 26 , 3869 (1996), Aust. J. Chem., 22 , 2497 (19
69) It can be produced according to the method described in J. Chem. Soc., 3673 (1964). That is, for example, a 2-halogenobenzoic acid derivative represented by the general formula (2) (Formula 4) is reacted with a 2-aminopyridine derivative represented by the general formula (3) (Formula 4) in the presence of copper. It can be manufactured by the following.

[0021]

Embedded image [In the above formula, X _{1 to} X ₈ represent the same meaning as in the general formula (1), and Z represents a halogen atom.]

The organic electroluminescent element usually has at least one light-emitting layer containing at least one light-emitting component sandwiched between a pair of electrodes. In consideration of the functional levels of hole injection and hole transport, electron injection and electron transport of the compound used in the light-emitting layer, a hole injection transport layer containing a hole injection transport component and / or An electron injection / transport layer containing an injection / transport component can also be provided. For example, when the hole injection function, hole transport function and / or electron injection function, and electron transport function of the compound used for the light emitting layer are good, the light emitting layer is formed of the hole injection transport layer and / or the electron injection transport layer. The element can also be configured to serve as Of course, depending on the case, a structure of a device (single-layer device) without both the hole injection transport layer and the electron injection transport layer may be employed. Further, each of the hole injection transport layer, the electron injection transport layer and the light emitting layer may have a single-layer structure or a multilayer structure,
The hole injecting and transporting layer and the electron injecting and transporting layer can be formed by separately providing a layer having an injection function and a layer having a transport function in each layer.

In the organic electroluminescent device of the present invention, the compound A according to the present invention is preferably used for a hole injection / transport component, a light emission component or an electron injection / transport component, and is preferably used for a light emission component or an electron injection / transport component. More preferred.
In the organic electroluminescent device of the present invention, the compound A according to the present invention may be used alone or in combination.

The structure of the organic electroluminescent device of the present invention is not particularly limited.
Hole injection / transport layer / emission layer / electron injection / transport layer / cathode device (FIG. 1), (B) anode / hole injection / transport layer / emission layer / cathode device (FIG. 2), (C) anode / emission Layer / electron injection / transport layer / cathode type device (FIG. 3), (D) anode / light emitting layer / cathode type device (FIG. 4) and the like. Further, the device is of a type in which a light emitting layer is sandwiched between electron injection and transport layers (E).
Anode / hole injection / transport layer / electron injection / transport layer / emission layer / electron injection / transport layer / cathode type device (FIG. 5).
The element configuration of the (D) type is, of course, an element of a type in which a light emitting component is sandwiched between a pair of electrodes in a single layer form, and further, for example, (F) a hole injection / transport component, a light emitting component, An element of a type in which an electron injection / transport component is mixed and sandwiched between a pair of electrodes (FIG. 6), and (G) a layer in which a hole injection / transport component and a light emitting component are mixed, between a pair of electrodes. There is an element of a sandwiched type (FIG. 7) or (H) an element of a type sandwiched between a pair of electrodes in a single-layer form in which a light emitting component and an electron injection / transport component are mixed (FIG. 8).

The organic electroluminescent device of the present invention is not limited to these device configurations, and each type of device may be provided with a plurality of hole injection / transport layers, light emitting layers, and electron injection / transport layers. it can. In each type of device, a light emitting component is provided between the hole injecting and transporting layer and the light emitting layer, and / or a mixed layer of the hole injecting and transporting component and the light emitting component and / or between the light emitting layer and the electron injecting and transporting layer. And a mixed layer of an electron injection and transport component. More preferred configurations of the organic electroluminescent device are (A) type device, (B) type device, and (C) type device.
Element, (E) element, (F) element, (G) element or (H) element, more preferably (A) element, (B) element, (C) element , (F) type element or (H) type element.

As the organic electroluminescent device of the present invention, for example, (A) anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode type device shown in FIG. 1 will be described.
In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injection / transport layer, 4 is a light emitting layer, 5 is an electron injection / transport layer, 6 is a cathode,
Reference numeral 7 denotes a power supply.

The organic electroluminescent device of the present invention is preferably supported on a substrate 1. The substrate is not particularly limited, but is preferably transparent or translucent. Transparent plastic sheet (for example, polyester, polycarbonate, polysulfone, polymethyl methacrylate, polypropylene,
A sheet made of polyethylene or the like), a translucent plastic sheet, quartz, a transparent ceramic, or a composite sheet combining these. Further, the luminescent color can be controlled by combining, for example, a color filter film, a color conversion film, and a dielectric reflection film on the substrate.

As the anode 2, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively large work function as an electrode material. As the electrode material used for the anode, for example, gold, platinum, silver, copper, cobalt, nickel,
Palladium, vanadium, tungsten, tin oxide, zinc oxide, ITO (indium tin oxide), polythiophene, polypyrrole, and the like can be given. These electrode substances may be used alone or in combination of two or more. The anode can be formed on the substrate by using such an electrode material by a method such as a vapor deposition method and a sputtering method. Further, the anode may have a single-layer structure or a multilayer structure. The sheet electric resistance of the anode is preferably several hundred Ω / □.
Hereinafter, more preferably, it is set to about 5 to 50 Ω / □. The thickness of the anode depends on the material of the electrode substance to be used, but is generally about 5 to 1000 nm, more preferably,
It is set to about 10 to 500 nm.

The hole injection / transport layer 3 is a layer containing a compound having a function of facilitating the injection of holes (holes) from the anode and a function of transporting the injected holes. The hole injecting and transporting layer is formed of the compound A according to the present invention and / or another compound having a hole injecting and transporting function (for example, a phthalocyanine derivative, a triarylmethane derivative, a triarylamine derivative, an oxazole derivative, a hydrazone derivative, a stilbene derivative). , Pyrazoline derivatives, polysilane derivatives, polyphenylenevinylene and its derivatives,
Polythiophene and a derivative thereof, a poly-N-vinylcarbazole derivative, and the like). The compounds having a hole injection / transport function may be used alone or in combination.

Other compounds having a hole injection / transport function used in the present invention include triarylamine derivatives (for example, 4,4′-bis [N-phenyl-N- (4 ″)).
-Methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N-
(3 ″ -methoxyphenyl) amino] biphenyl, 4,
4'-bis [N-phenyl-N- (1 "-naphthyl) amino] biphenyl, 3,3'-dimethyl-4,4'-bis [N-phenyl-N- (3" -methylphenyl) Amino] biphenyl, 1,1-bis [4 ′-[N, N-di (4 ″ -methylphenyl) amino] phenyl] cyclohexane, 9,10-bis [N- (4′-methylphenyl) -N -(4 "-n-butylphenyl) amino] phenanthrene, 3,8-bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-
N, N-bis [4 ″, 4 ′ ″-bis [N ′, N′-di (4-methylphenyl) amino] biphenyl-4-yl] aniline, N, N′-bis [4- ( Diphenylamino) phenyl] -N, N'-diphenyl-1,3-diaminobenzene, N, N'-bis [4- (diphenylamino) phenyl] -N, N'-diphenyl-1,4-diaminobenzene, 5,5 ″ -bis [4- (bis [4-methylphenyl] amino) phenyl] -2,2 ′: 5 ′,
2 ″ -terthiophene, 1,3,5-tris (diphenylamino) benzene, 4,4 ′, 4 ″ -tris (N-carbazoyl) triphenylamine, 4,4 ′, 4 ″ -tris [ N- (3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine, 4,4 ′, 4 ″ -tris [N, N-bis (4 ′ ″-tert-butylbiphenyl-)
4 ""-yl) amino] triphenylamine, 1,3
5-tris [N- (4-diphenylaminophenyl)-
N-phenylamino] benzene, polythiophene and derivatives thereof, and poly-N-vinylcarbazole derivatives are more preferred. When the compound A according to the present invention is used in combination with another compound having a hole injecting and transporting function, the proportion of the compound A according to the present invention in the hole injecting and transporting layer is preferably 0.1 to 40% by weight. Prepare to about.

The light emitting layer 4 has a function of injecting holes and electrons,
This is a layer containing a compound having a transport function thereof and a function of generating excitons by recombination of holes and electrons. The light-emitting layer is formed of the compound A according to the present invention and / or another compound having a light-emitting function (eg, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, a polycyclic aromatic compound [eg, rubrene, anthracene, tetracene, pyrene). , Perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthracenyl) ) Benzene, 4,4′-bis (9 ″ -ethynylanthracenyl) biphenyl], triarylamine derivatives [for example, the compounds described above as compounds having a hole injecting and transporting function], and organic metals Complexes [for example, tris (8-quino Linoleate) aluminum, bis (10-benzo [h] quinolinolate) beryllium, 2
Zinc salt of-(2'-hydroxyphenyl) benzoxazole, zinc salt of 2- (2'-hydroxyphenyl) benzothiazole, zinc salt of 4-hydroxyacridine,
Zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone], stilbene derivative [for example, 1,1,4,
4-tetraphenyl-1,3-butadiene, 4,4′-
Bis (2,2-diphenylvinyl) biphenyl, 4,
4'-bis [(1,1,2-triphenyl) ethenyl]
Biphenyl], coumarin derivatives [for example, coumarin 1,
Coumarin 6, Coumarin 7, Coumarin 30, Coumarin 10
6, Coumarin 138, Coumarin 151, Coumarin 15
2, Coumarin 153, Coumarin 307, Coumarin 31
1. Coumarin 314, Coumarin 334, Coumarin 33
8, coumarin 343, coumarin 500], pyran derivatives [for example, DCM1, DCM2], oxazone derivatives [for example, Nile Red], benzothiazole derivatives,
Benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamate derivatives, poly-
N-vinyl carbazole and its derivatives, polythiophene and its derivatives, polyphenylene and its derivatives, polyfluorene and its derivatives, polyphenylene vinylene and its derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and And at least one of its derivatives, polythienylenevinylene and derivatives thereof).

In the organic electroluminescent device of the present invention, the light emitting layer preferably contains the compound A of the present invention. When the compound A according to the present invention and a compound having another light-emitting function are used in combination, the ratio of the compound A according to the present invention in the light-emitting layer is preferably 0.001 to 99.99.
About 9% by weight, more preferably 0.01 to 99.99
% By weight, more preferably about 0.1 to 99.9% by weight.

As the other compound having a light emitting function used in the present invention, a polycyclic aromatic compound, a light emitting organic metal complex or a triarylamine derivative is more preferable.
For example, J. Appl. Phys., 65 , 3610 (1989);
As described in JP-A-214332, the light emitting layer may be composed of a host compound and a guest compound (dopant). The compound A according to the present invention can be used as a host compound to form a light emitting layer, and further can be used as a guest compound to form a light emitting layer. When the light emitting layer is formed using the compound A according to the present invention as a guest compound, the host compound is more preferably a light emitting organometallic complex or the above triarylamine derivative. In this case, the compound A according to the present invention is preferably used in an amount of about 0.001 to 40% by weight, more preferably about 0.01 to 30% by weight, based on the luminescent organometallic complex or the triarylamine derivative. I do.

The polycyclic aromatic compound used in combination with the compound A according to the present invention is not particularly limited. For example, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene , Pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9.1
0-bis (phenylethynyl) anthracene, 1,4-
Bis (9'-ethynylanthracenyl) benzene, 4,
4′-bis (9 ″ -ethynylanthracenyl) biphenyl and the like can be mentioned. Of course, the polycyclic aromatic compound may be used alone or in combination.

The luminous organometallic complex used in combination with the compound A according to the present invention is not particularly limited, but a luminous organoaluminum complex is preferable, and a luminescence having a substituted or unsubstituted 8-quinolinolate ligand. Organic aluminum complexes are more preferred. Preferred luminescent organometallic complexes include, for example, general formulas (a) to (c)
And a luminescent organic aluminum complex represented by (Q) ₃ -Al (a) (wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand) (Q) ₂ -Al-OL (b) (wherein Q represents substituted 8 -Represents a quinolinolate ligand, O
-L is a phenolate ligand, and L represents a hydrocarbon group having 6 to 24 carbon atoms including a phenyl moiety.) (Q) ₂ -Al-O-Al- (Q) ₂ (c) Q represents a substituted 8-quinolinolate ligand)

Specific examples of the luminescent organometallic complex include, for example, tris (8-quinolinolate) aluminum, tris (4-methyl-8-quinolinolate) aluminum, tris (5-methyl-8-quinolinolate) aluminum, tris ( 3,4-dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, tris (4,6-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-8-quinolinolate) (Phenolate) aluminum, bis (2-methyl-8-quinolinolate) (2-
Methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(4-methylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum,

Bis (2-methyl-8-quinolinolate)
(4-phenylphenolate) aluminum, bis (2
-Methyl-8-quinolinolate) (2,3-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,6-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(3,4-dimethylphenolato) aluminum, bis (2-methyl-8-quinolinolate) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8
-Quinolinolate) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2
4,6-trimethylphenolato) aluminum, bis (2-methyl-8-quinolinolate) (2,4,5,6
-Tetramethylphenolate) aluminum, bis (2
-Methyl-8-quinolinolate) (1-naphtholate)
Aluminum, bis (2-methyl-8-quinolinolate) (2-naphtholate) aluminum, bis (2,4
-Dimethyl-8-quinolinolate) (2-phenylphenolato) aluminum, bis (2,4-dimethyl-8)
-Quinolinolate) (3-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-
Dimethylphenolate) aluminum, bis (2,4-
Dimethyl-8-quinolinolate) (3,5-di-tert-
Butyl phenolate) aluminum,

Bis (2-methyl-8-quinolinolate)
Aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolato) aluminum, Bis (2-methyl-4-ethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-
4-ethyl-8-quinolinolate) aluminum, bis (2-methyl-4-methoxy-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-4-methoxy-8-quinolinolate) aluminum, bis (2-
Methyl-5-cyano-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-
Quinolinolate) aluminum, bis (2-methyl-5)
-Trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum. Of course, the luminescent organometallic complex may be used alone or in combination.

The triarylamine derivative used in combination with the compound A according to the present invention is not particularly limited, and examples thereof include the compounds described above as compounds having a hole injection / transport function. Of course, the triarylamine derivative may be used alone or in combination.

The electron injection / transport layer 5 is a layer containing a compound having a function of facilitating the injection of electrons from the cathode and a function of transporting the injected electrons. The electron injecting and transporting layer is formed of the compound A according to the present invention and / or another compound having an electron injecting and transporting function (for example, an organometallic complex [for example, tris (8-quinolinolate) aluminum, bis (10-benzo [h] quinolinolate) ) Beryllium, 5
-Beryllium salt of hydroxyflavone, aluminum salt of 5-hydroxyflavone], oxadiazole derivative, triazole derivative, triazine derivative, perylene derivative, quinoline derivative, quinoxaline derivative, diphenylquinone derivative, nitro-substituted fluorenone derivative, thiopyrandioxide derivative And the like can be formed using at least one of the above.

In the organic electroluminescent device of the present invention, the electron injecting and transporting layer preferably contains the compound A of the present invention. When the compound A according to the present invention and another compound having an electron injecting and transporting function are used in combination, the proportion of the compound A according to the present invention in the electron injecting and transporting layer is preferably 0.1% by weight or more, and more preferably. Is 0.1 to 40
%, More preferably about 0.2 to 30% by weight, particularly preferably about 0.5 to 20% by weight. In the present invention, the compound A according to the present invention and an organometallic complex [for example, the compounds represented by the general formulas (a) to (c)] are used together to form an electron injecting and transporting layer. preferable.

As the cathode 6, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively small work function as an electrode material. Examples of the electrode material used for the cathode include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium,
Manganese, yttrium, aluminum, an aluminum-lithium alloy, an aluminum-calcium alloy, an aluminum-magnesium alloy, a graphite thin film, and the like can be given. These electrode substances may be used alone or in combination of two or more.

The cathode can be formed on the electron injecting and transporting layer by using these electrode materials by, for example, a vapor deposition method, a sputtering method, an ionization vapor deposition method, an ion plating method, a cluster ion beam method, or the like. . Further, the cathode may have a single-layer structure or a multilayer structure. The sheet electric resistance of the cathode is several hundred Ω.
/ □ or less is preferable. The thickness of the cathode depends on the material of the electrode substance to be used, but generally ranges from 5 to 1000.
nm, more preferably about 10-500 nm. In order to efficiently extract the light emitted from the organic electroluminescent device, at least one electrode of the anode or the cathode is
It is preferably transparent or translucent, and in general, it is more preferable to set the material and thickness of the anode so that the transmittance of emitted light is 70% or more.

Further, in the organic electroluminescent device of the present invention, at least one of the layers may contain a singlet oxygen quencher. The singlet oxygen quencher is not particularly limited and includes, for example, rubrene,
Nickel complexes, diphenylisobenzofuran and the like can be mentioned, and rubrene is particularly preferred. The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injection transport layer, and more preferably a hole injection transport layer.
For example, when a singlet oxygen quencher is contained in the hole injecting and transporting layer, the singlet oxygen quencher may be contained uniformly in the hole injecting and transporting layer. (An electron injection / transport layer having a light emitting function). The content of the singlet oxygen quencher is from 0.01 to 50% by weight, preferably from 0.0 to 50% by weight of the total amount constituting the contained layer (for example, the hole injection / transport layer).
5 to 30% by weight, more preferably 0.1 to 20% by weight
It is.

The method for forming the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is not particularly limited, and may be, for example, a vacuum evaporation method, an ionization evaporation method, a solution coating method (for example, a spin coating method, a casting method, or the like). Method, dip coating method,
It can be manufactured by forming a thin film by a bar coating method, a roll coating method, a Langmuir-Brosette method, or the like. When forming each layer by a vacuum deposition method, the conditions of the vacuum deposition are not particularly limited,
It is carried out under a vacuum of about 10 ^-5 Torr or less, a boat temperature of about 50 to 400 ° C. (evaporation source temperature), a substrate temperature of about −50 to 300 ° C., and a deposition rate of about 0.005 to 50 nm / sec. Is preferred. In this case, by forming each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer continuously under a vacuum, an organic electroluminescent element having more excellent characteristics can be manufactured. When each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer is formed using a plurality of compounds by a vacuum deposition method, each boat containing the compounds is individually temperature-controlled and co-deposited. Is preferred.

When each layer is formed by a solution coating method,
The components forming each layer or the components and a binder resin or the like are dissolved or dispersed in a solvent to form a coating liquid. Examples of the binder resin that can be used for each of the hole injection transport layer, the light emitting layer, and the electron injection transport layer include poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl acrylate, and the like.
Polymethyl methacrylate, polyether, polycarbonate, polyamide, polyimide, polyamide imide,
High molecular compounds such as polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and its derivatives, polythiophene and its derivatives, polyphenylenevinylene and its derivatives, polyfluorene and its derivatives, and polythienylenevinylene and its derivatives. . The binder resin may be used alone or in combination.

When each layer is formed by a solution coating method,
The components forming each layer or the components and a binder resin are combined with a suitable organic solvent (for example, hexane, octane,
Decane, toluene, xylene, ethylbenzene, hydrocarbon solvents such as 1-methylnaphthalene, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, ketone solvents such as cyclohexanone, for example, dichloromethane, chloroform, tetrachloromethane, dichloroethane, trichloroethane, Halogenated hydrocarbon solvents such as tetrachloroethane, chlorobenzene, dichlorobenzene, and chlorotoluene, for example, ester solvents such as ethyl acetate, butyl acetate, and amyl acetate, for example, methanol, propanol, butanol, pentanol, hexanol, and cyclohexanol , Methyl cellosolve, ethyl cellosolve, alcohol solvents such as ethylene glycol, for example, dibutyl ether, tetrahydrofuran,
Dioxane, ether solvents such as anisole, for example,
Polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide) and / or dissolved in water Alternatively, a thin film can be formed by various coating methods by dispersing the mixture into a coating liquid.

The method of dispersion is not particularly limited. For example, the particles can be dispersed into fine particles using a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like. The concentration of the coating solution is not particularly limited, and can be set to a concentration range suitable for producing a desired thickness by a coating method to be performed. Preferably, the solution concentration is about 1 to 30% by weight. When a binder resin is used, the amount of the binder resin used is not particularly limited. 5) to 99.9% by weight
Level, preferably about 10 to 99% by weight, more preferably about 15 to 90% by weight.

The thicknesses of the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer are not particularly limited, but are generally preferably set to about 5 nm to 5 μm.
A protective layer (sealing layer) may be provided on the fabricated device for the purpose of preventing contact with oxygen, moisture, or the like, or the device may be formed of, for example, paraffin, liquid paraffin, silicon oil, fluorocarbon oil, zeolite, It can be protected by being enclosed in an inert substance such as a contained fluorocarbon oil. Examples of the material used for the protective layer include organic polymer materials (for example, fluorinated resin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene) , Polyphenylene oxide), inorganic materials (for example, diamond thin film, amorphous silica, electrically insulating glass, metal oxide, metal nitride, metal carbide,
Metal sulfide), and a photocurable resin. The material used for the protective layer may be used alone or in combination of two or more. The protective layer may have a single-layer structure or a multilayer structure.

Further, a metal oxide film (for example, an aluminum oxide film) or a metal fluoride film can be provided as a protective film on the electrode. Also, for example, on the surface of the anode,
For example, an interface layer (intermediate layer) composed of an organic phosphorus compound, polysilane, an aromatic amine derivative, and a phthalocyanine derivative
Can also be provided. Further, electrodes, eg, anodes, can be used by treating the surface with, eg, acid, ammonia / hydrogen peroxide, or plasma.

The organic electroluminescent device of the present invention is generally used as a DC-driven device, but can also be used as a pulse-driven or AC-driven device.
Incidentally, the applied voltage is generally about 2 to 30 V. The organic electroluminescent device of the present invention can be used for, for example, a panel light source, various light emitting devices, various display devices, various labels, various sensors, and the like.

[0052]

The present invention will be described in more detail with reference to the following examples, which, of course, are not intended to limit the scope of the present invention. Example 1 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec to a thickness of 75 nm. This was used as a hole injection transport layer. Next, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and 11H-pyrido [2,1-b] quinazolin-11-one (compound of Exemplified Compound No. 1) are further placed thereon.
From different deposition sources at a deposition rate of 0.2 nm / sec.
It was co-evaporated to a thickness of 0 nm (weight ratio: 100: 0.5) to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec for 200 n.
An organic electroluminescent device was prepared by co-evaporating the resultant to a thickness of 10 m (weight ratio: 10: 1) to form a cathode. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed. Brightness 2260c
Blue light emission of d / m ² was confirmed.

Examples 2 to 16 In Example 1, instead of using the compound of Exemplified Compound No. 1 in forming the light emitting layer, Exemplified Compound No. 4 was used.
(Example 2), compound of Exemplified Compound No. 7 (Example 3), compound of Exemplified Compound No. 9 (Example 4), compound of Exemplified Compound No. 11 (Example 5), compound of Exemplified Compound No. 14 (Example 6), Compound of Exemplified Compound No. 16 (Example 7), Compound of Exemplified Compound No. 24 (Example 8), Compound of Exemplified Compound No. 29 (Example 9), Compound of Exemplified Compound No. 42 (Example Example 10), Compound of Exemplified Compound No. 46 (Example 11), Exemplified Compound No. 48
(Example 12), the compound of Exemplified Compound No. 49 (Example 13), the compound of Exemplified Compound No. 52 (Example 14), the compound of Exemplified Compound No. 55 (Example 15),
An organic electroluminescent device was produced by the method described in Example 1 except that the compound of Exemplified Compound No. 57 (Example 16) was used. 12V in each element under dry atmosphere
As a result, blue to blue-green light emission was confirmed. The characteristics were further examined, and the results are shown in Table 1 (Table 1).

Comparative Example 1 In Example 1, when forming the light emitting layer, the compound of Exemplified Compound No. 1 was not used, and bis (2-methyl-8-
An organic electroluminescent device was prepared by the method described in Example 1, except that quinolinolate) (4-phenylphenolate) aluminum alone was used to form a light emitting layer by vapor deposition to a thickness of 50 nm. This device was exposed to a 12 V
As a result, blue light emission was confirmed. The characteristics were further examined, and the results are shown in Table 1 (Table 1).

Comparative Example 2 In Example 1, when forming the light emitting layer, instead of using the compound of Exemplified Compound No. 1, N-methyl-2-
An organic electroluminescent device was manufactured by the method described in Example 1 except that methoxyacridone was used. When a DC voltage of 12 V was applied to this device under a dry atmosphere, blue light emission was confirmed. Further investigate its properties,
The results are shown in Table 1 (Table 1).

[0056]

[Table 1]

Example 17 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec to a thickness of 75 nm. This was used as a hole injection transport layer. Next, bis (2-methyl-8-quinolinolate) (2-phenylphenolate) aluminum and the compound of Exemplified Compound No. 10 were deposited thereon from different evaporation sources at a deposition rate of 0.2 nm / sec and a thickness of 50 nm. Is co-deposited (weight ratio 100: 1.0),
It was a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further on that,
Magnesium and silver are deposited at a deposition rate of 0.2 nm / sec.
Co-deposit (weight ratio 10: 1) to a thickness of nm to form a cathode,
An organic electroluminescent device was manufactured. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 58 mA / cm ² flowed. Brightness 2250c
Blue light emission of d / m ² was confirmed.

Example 18 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec to a thickness of 75 nm. The hole injection transport layer was used. Then, on top of this, bis (2-methyl-8-quinolinolato) aluminum-μ
-Oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. 17 were co-evaporated from different evaporation sources to a thickness of 50 nm at a deposition rate of 0.2 nm / sec (weight ratio 100: 2. 0) to form a light emitting layer.
Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, the voltage was 57 mA /
cm ² of current flowed. Blue light emission with a luminance of 2240 cd / m ² was confirmed.

Example 19 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec to a thickness of 75 nm. This was used as a hole injection transport layer. Then, on this, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum and the compound of Exemplified Compound No. 31 were added from different evaporation sources. 5 at a deposition rate of 0.2 nm / sec
It was co-evaporated to a thickness of 0 nm (weight ratio: 100: 4.0) to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec for 200 n.
An organic electroluminescent device was prepared by co-evaporating the resultant to a thickness of 10 m (weight ratio: 10: 1) to form a cathode. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 60 mA / cm ² flowed. Brightness 2280c
Blue light emission of d / m ² was confirmed.

Example 20 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec to a thickness of 75 nm. This was used as a hole injection transport layer. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. 30 were deposited thereon from different evaporation sources at an evaporation rate of 0.2 n.
m / sec at a thickness of 50 nm (weight ratio 100:
1.0) to form a light-emitting layer also serving as an electron injection / transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm.
/ Sec to co-evaporate to a thickness of 200nm (weight ratio 10: 1)
This was used as a cathode to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 58 mA / cm ² flowed.
Blue-green light emission with a luminance of 2170 cd / m ² was confirmed.

Example 21 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec to a thickness of 75 nm. This was used as a hole injection transport layer. Then, on top of it,
1,4,4-tetraphenyl-1,3-butadiene is
Deposit to a thickness of 50 nm at a deposition rate of 0.2 nm / sec.
It was a light emitting layer. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. 1 were further deposited thereon from different evaporation sources at an evaporation rate of 0.2 nm / sec.
Co-evaporation (weight ratio: 100: 4.0) was performed to a thickness of 0 nm to obtain an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 14 V was applied to the manufactured organic electroluminescent device under a dry atmosphere, the voltage was 52 mA /
cm ² of current flowed. Blue light emission with a luminance of 2170 cd / m ² was confirmed.

Example 22 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec to a thickness of 75 nm. This was used as a hole injection transport layer. Next, the compound of Exemplified Compound No. 14 was deposited thereon from a different deposition source at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form a light emitting layer. Then, 1,3-bis [5 ′-(p-
[tert-butylphenyl) -1,3,4-oxadiazol-2'-yl] benzene at a deposition rate of 0.2 nm / sec.
Was deposited to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm.
/ Sec to co-evaporate to a thickness of 200nm (weight ratio 10: 1)
This was used as a cathode to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 14 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 48 mA / cm ² flowed.
Blue light emission with a luminance of 1840 cd / m ² was confirmed.

Example 23 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, a compound of Exemplified Compound No. 10 was deposited on an ITO transparent electrode to a thickness of 55 nm at a deposition rate of 0.2 nm / sec to form a light emitting layer. Then, on top of that, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-
Oxadiazol-2'-yl] benzene was deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device under a dry atmosphere, the voltage was 68 mA / c.
m ² of current flowed. Blue light emission with a luminance of 1250 cd / m ² was confirmed.

Example 24 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4 ′, 4 ″ -tris [N
-(3 "'-methylphenyl) -N-phenylamino]
Triphenylamine was deposited at a deposition rate of 0.1 nm / sec.
It was deposited to a thickness of 50 nm to form a first hole injection / transport layer.
Then, 4,4′-bis [N-phenyl-N- (1 ″-
Naphthyl) amino] biphenyl and the compound of Exemplified Compound No. 1 were obtained from different evaporation sources at an evaporation rate of 0.2 nm / sec.
And co-evaporation to a thickness of 20 nm (weight ratio 100: 30)
Thus, the light emitting layer also served as the second hole injection / transport layer. Next, tris (8-quinolinolate) aluminum was deposited thereon to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to form an electron injection transport layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm / sec at 200 nm.
And a cathode was formed by co-evaporation (weight ratio: 10: 1) to obtain an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 65 mA / cm ² flowed. Brightness 2650c
Blue-green light emission of d / m ² was confirmed.

Example 25 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4 ′, 4 ″ -tris [N
-(3 "'-methylphenyl) -N-phenylamino]
Triphenylamine was deposited at a deposition rate of 0.1 nm / sec.
It was deposited to a thickness of 50 nm to form a first hole injection / transport layer.
Then, 4,4′-bis [N-phenyl-N- (1 ″-
Naphthyl) amino] biphenyl and the compound of Exemplified Compound No. 14 were obtained from different evaporation sources at an evaporation rate of 0.2 nm / se.
c, co-deposition to a thickness of 20 nm (weight ratio 100: 20)
Thus, the light emitting layer also served as the second hole injection / transport layer. Next, tris (8-quinolinolate) aluminum was deposited thereon to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to form an electron injection transport layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm / sec at 200 nm.
And a cathode was formed by co-evaporation (weight ratio: 10: 1) to obtain an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 64 mA / cm ² flowed. Brightness 2850c
Blue-green light emission of d / m ² was confirmed.

Example 26 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl is deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 50 nm.
This was used as a hole injection transport layer. Next, the compound of Exemplified Compound No. 9 and decacyclene were co-evaporated from different evaporation sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio: 100: 10) to form a light emitting layer. Then, on top of that,
Tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, the voltage was 64 mA / c.
m ² of current flowed. Green light emission with a luminance of 2650 cd / m ² was confirmed.

Example 27 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl is deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 50 nm.
This was used as a hole injection transport layer. Next, the compound of Exemplified Compound No. 25 and rubrene were evaporated from different evaporation sources at an evaporation rate of 0.
Co-deposition at 2 nm / sec to a thickness of 50 nm (weight ratio 10
0: 7) to form a light emitting layer. Then tris (8-quinolinolato) aluminum was deposited thereon with a deposition rate of 0,1.
Vapor deposition was performed at 2 nm / sec to a thickness of 50 nm to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. The prepared organic electroluminescent device was dried under a dry atmosphere for 15 minutes.
When a DC voltage of V was applied, a current of 67 mA / cm ² flowed. Yellow light emission with a luminance of 3050 cd / m ² was confirmed.

Example 28 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, poly-N-vinylcarbazole (weight average molecular weight 1
50000), compound of Exemplified Compound No. 18, coumarin 6 [“3- (2′-benzothiazolyl) -7-diethylaminocoumarin” (green light-emitting component)], and DCM
1 ["4- (dicyanomethylene) -2-methyl-6
(4'-dimethylaminostyryl) -4H-pyran "
(Orange light-emitting component)] at a weight ratio of 10
Using a 3% by weight dichloroethane solution containing 0: 5: 3: 2, a thickness of 400 was obtained by dip coating.
A light emitting layer of nm was formed. Next, after fixing the glass substrate having the light emitting layer to a substrate holder of a vapor deposition device, the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. Further, 3- (4′-tert-butylphenyl) -4-phenyl-5- (4 ″ -biphenyl) -1,2,4-triazole was deposited on the light emitting layer at a deposition rate of 0.2 nm / After vapor deposition to a thickness of 20 nm in sec, tris (8-quinolinolate) aluminum was further vapor-deposited to a thickness of 30 nm at a vapor deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / se.
A co-evaporation (weight ratio 10: 1) was carried out to a thickness of 200 nm at c to obtain a cathode, thereby producing an organic electroluminescent device. In addition, evaporation is
The test was performed while maintaining the reduced pressure of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 74 mA / cm ² flowed. White light emission with a luminance of 1220 cd / m ² was confirmed.

Example 29 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, poly-N-vinylcarbazole (weight average molecular weight 1
50000), 1,3-bis [5 '-(p-tert-butylphenyl) -1,3,4-oxadiazole-2'-
Yl] benzene and the compound of Exemplified Compound No. 21
A 300 nm-thick light emitting layer was formed by a dip coating method using a 3 wt% dichloroethane solution containing each in a weight ratio of 100: 30: 3. Next, after fixing the glass substrate having the light emitting layer to a substrate holder of a vapor deposition device, the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. Further, on the light emitting layer, magnesium and silver were deposited at a deposition rate of 0.2.
at 200 nm / sec to a thickness of 200 nm (weight ratio: 10:
1) The resultant was used as a cathode to produce an organic electroluminescent device. When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 76 mA / cm ² flowed. Blue light emission with a luminance of 1380 cd / m ² was confirmed.

Comparative Example 3 The procedure of Example 29 was repeated, except that 1,1,4,4-tetraphenyl-1,3-butadiene was used instead of the compound of Exemplified Compound No. 21 in forming the light emitting layer. An organic electroluminescent device was produced by the method described in Example 29. When a DC voltage of 15 V was applied to the produced organic electric field device under a dry atmosphere, a current of 86 mA / cm ² flowed. Blue light emission with a luminance of 680 cd / m ² was confirmed.

Example 30 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, polycarbonate (weight average molecular weight: 50,000),
4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl, bis (2-methyl-8-
Quinolinolate) aluminum-μ-oxo-bis (2
-Methyl-8-quinolinolate) aluminum and the compound of Exemplified Compound No. 6 were added in a weight ratio of 100: 4, respectively.
Using a 3 wt% dichloroethane solution containing 0: 60: 1 in a ratio of 300 n by a dip coating method.
m light emitting layers were formed. Next, after fixing the glass substrate having the light emitting layer to a substrate holder of a vapor deposition device, the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. Further, on the light emitting layer, magnesium and silver were co-deposited (weight ratio: 10: 1) to a thickness of 200 nm at a deposition rate of 0.2 nm / sec to form an organic electroluminescent device. When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 66 mA / cm ² flowed. Brightness 77
Blue light emission of 0 cd / m ² was confirmed.

Example 31 A glass substrate was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, the compound of Exemplified Compound No. 1 was deposited on a glass substrate at a deposition rate of 0.2 nm /
Evaporated to a thickness of 100 nm in sec. On top of that, magnesium and silver were deposited at a deposition rate of 0.2 nm / sec at 200 nm.
To a cathode by co-evaporation (weight ratio: 10: 1).
In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank.
Then, after attaching the scotch tape on the cathode, the scotch tape was peeled off, and together with the cathode, the thin film of the compound of Exemplified Compound No. 1 was also peeled off the glass substrate, and it was found that the adhesion to the cathode was good. .

Comparative Example 4 A thin film obtained by depositing a cathode by the method described in Example 31 except that N-methyl-2-methoxyacridone was used instead of the compound of Exemplified Compound No. 1 in Example 31 was used. Produced. Then, after attaching the scotch tape on the cathode, when the scotch tape was peeled off, it peeled off between the cathode and the thin film of N-methyl-2-methoxyacridone, and the adhesion to the cathode was found to be poor. did.

[0074]

According to the present invention, it has become possible to provide an organic electroluminescent device having excellent light emission luminance.

[Brief description of the drawings]

FIG. 1 is a schematic structural view of an example (A) of an organic electroluminescent element.

FIG. 2 is a schematic structural diagram of an example (B) of an organic electroluminescent element.

FIG. 3 is a schematic structural view of an example (C) of an organic electroluminescent element.

FIG. 4 is a schematic structural diagram of an example (D) of an organic electroluminescent element.

FIG. 5 is a schematic structural diagram of an example (E) of an organic electroluminescent element.

FIG. 6 is a schematic structural diagram of an example (F) of an organic electroluminescent element.

FIG. 7 is a schematic structural diagram of an example (G) of an organic electroluminescent element.

FIG. 8 is a schematic structural view of an example (H) of an organic electroluminescent element.

[Explanation of symbols]

 1: substrate 2: anode 3: hole injection / transport layer 3a: hole injection / transport component 4: light emitting layer 4a: light emitting component 5: electron injection / transport layer 5 ″: electron injection / transport layer 5a: electron injection / transport component 6: Cathode 7: Power supply

Claims (7)

[Claims] 1. The method of claim 1, wherein 11H-pyrido [2,1-
b] An organic electroluminescent element comprising at least one layer containing at least one quinazolin-11-one derivative. 2. 11H-pyrido [2,1-b] quinazoline-1
2. The layer containing a 1-one derivative is a light emitting layer.
The organic electroluminescent device according to claim 1. 3. 11H-pyrido [2,1-b] quinazoline-1
The organic electroluminescent device according to claim 1, wherein the layer containing the 1-one derivative is an electron injection transport layer. 4. 11H-pyrido [2,1-b] quinazoline-1
The organic electroluminescent device according to any one of claims 1 to 3, wherein the layer containing the 1-one derivative contains a polycyclic aromatic compound, a luminescent organometallic complex, or a triarylamine derivative. 5. The organic electroluminescent device according to claim 1, further comprising a hole injection transport layer between the pair of electrodes. 6. The organic electroluminescent device according to claim 1, further comprising an electron injection / transport layer between the pair of electrodes. 7. 11H-pyrido [2,1-b] quinazoline-1
The organic electroluminescent device according to claim 1, wherein the 1-one derivative is a compound represented by the general formula (1). Embedded image (Wherein X _{1 to} X ₈ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aralkyl group, It represents a unsubstituted aryl group or a substituted or unsubstituted aryloxy group, further, X ₁
And X ₂ , X ₂ and X ₃ , X ₃ and X ₄ , X ₅ and X ₆ , X ₆ and X ₇ , and X ₇ and X ₈ are mutually bonded and substituted. Together with the carbon atom, it may form a substituted or unsubstituted carbocyclic aliphatic ring or a substituted or unsubstituted carbocyclic aromatic ring)