JP2003031367A - Organic electroluminescent element and display device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element of excellent luminous efficiency with a long service life, and a display device of low power consumption with a long service life using the organic electroluminescent element. SOLUTION: This organic electroluminescent element with an organic layer clamped between two electrodes contains a compound expressed by a general formula (1), in at least one layer of the organic layer. In the formula, B represents a boron atom, C represents a carbon atom, A11 , A12 and A13 represent a carbon atom or a nitrogen atom, Z11 , Z12 and Z13 represent an atomic group required to complete an aromatic ring, R11 , R12 and R13 independently represent an alkyl group, an alkyloxy group, an aryloxy group or an halogen atom, R14 , R15 and R16 independently represent a hydrogen atom or a monovalent substituent, and l, m, n independently represent 0-7.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence (hereinafter, may be abbreviated as organic EL) element and a display device, and more specifically to an organic electroluminescence element and display excellent in light emission brightness and life. Regarding the device.

[0002]

2. Description of the Related Art An electroluminescent display (ELD) is used as a light emitting type electronic display device.
Is mentioned. An inorganic electroluminescence element or an organic electroluminescence element is used as a constituent element of the ELD. Although the inorganic electroluminescent device has been used as a planar light source, a high alternating voltage was required to drive the light emitting device. On the other hand, an organic electroluminescence device has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and electrons and holes are injected into the light emitting layer to recombine to generate excitons. It is a light-emitting element that utilizes the fact that light is emitted (fluorescence / phosphorescence) when (exciton) is deactivated and this exciton is deactivated, and can emit light at a voltage of several V to several tens of V Further, since it is a self-luminous type, it has a wide viewing angle and high visibility, and since it is a thin-film type complete solid-state element, it is attracting attention from the viewpoints of space saving, portability and the like.

Up to now, various organic EL devices have been reported. For example, Appl. Phys. Lett. , V
ol. 51, 913 or JP-A-59-19439.
JP-A-63-295695 discloses a combination of a hole injection layer and an organic light emitting layer, JP-A-63-295695 discloses a combination of a hole injection layer and an electron injection transport layer, Jpn. J
individual of Applied Physic
s, vol. 127, No. 2, pp. 269 to 271, each discloses a combination of a hole transfer layer, a light emitting layer and an electron transfer layer, but a device with higher brightness has been demanded and energy conversion efficiency has been increased. Therefore, further improvement of the quantum efficiency of light emission is expected. It has also been pointed out that the organic EL element has a short light emission life. The cause of the deterioration of luminance over time has not been completely clarified, but the cause is that the electroluminescent element decomposes the organic compound itself that constitutes the thin film by the light emitted by itself and the heat generated at that time, or the thin film. It has been pointed out that factors derived from the organic compound, which is a material of the organic EL device, such as crystallization of the organic compound. Further, at present, electron transport materials have little knowledge, and in combination with utilizing antibonding orbitals, no high-performance electron transport materials useful for practical use have been found. For example, the research group at Kyushu University has been developing 2-
(4-biphenyl) -5- (4-t-butylphenyl)
-1,3,4-Oxadiazole (t-BuPBD) and oxadiazole dimer derivative 1,3-bis (4-t-butylphenyl-) having improved thin film stability
1,3,4-oxadizodyl) biphenylene (OXD-
1), 1,3-bis (4-t-butylphenyl-1,
3,4-Oxadizolyl) phenylene (OXD-7)
(Jpn. J. Appl. Phys. Vol. 31 (1
992), p. 1812) is proposed. In addition, a research group at Yamagata University has created a white light emitting device by using a triazole-based electron transport material having an excellent hole blocking property (Science, 3 March).
1995, Vol. 267, p. 1332). further,
JP-A-5-331459 describes that a phenanthroline derivative is useful as an electron transport material. However, conventional electron-transporting materials have a low thin-film forming ability and easily crystallize, so that there is a problem that the light-emitting element is destroyed, and the element performance that can be practically used cannot be expressed.

As an organic electroluminescent material that solves these problems, Japanese Patent Laid-Open No. 2000-290645 has been proposed.
JP-A-2000-294373, JP-A-20
Nos. 01-72971 and 2001-93670 describe examples of using a compound containing a boron atom in the molecule as a light emitting material or an electron transporting material.
It was not sufficient to achieve both luminous efficiency and luminous lifetime. In addition, in Japanese Patent Nos. 2,795,932, JP-A-9-245511, and JP-A-5-258860, light emitted from an organic EL element is converted into a maximum emission wavelength different from that by a color conversion layer. Is described, and an organic fluorescent dye is exemplified as a compound that converts the light emitted from the organic EL element. These methods can obtain a desired luminescent color only by changing the organic phosphor used for the color conversion layer, and thus the complicated patterning required when manufacturing a full-color organic EL is not necessary, and the cost can be reduced. Although it is possible to achieve this, the organic EL element described in the above patent does not have sufficient emission intensity,
The luminescence intensity obtained after conversion was not yet sufficient.

[0005]

Therefore, the first aspect of the present invention
It is an object of the invention to provide an organic electroluminescence device having excellent luminous efficiency and a long life. A second object of the present invention is to provide a display device using an organic electroluminescence element, which has low power consumption and long life. A third object of the present invention is to provide a low cost display device using a color conversion layer.

[0006]

The above objects of the present invention have been achieved by the following constitutions. (1) In an organic electroluminescence device having an organic layer sandwiched between two electrodes, at least one organic layer contains at least one compound represented by the following general formula (1): An organic electroluminescence device that does.

[0007]

[Chemical 4] In the formula, B represents a boron atom, C represents a carbon atom, and A
₁₁ , A ₁₂ and A ₁₃ represent a carbon atom or a nitrogen atom,
Z ₁₁ , Z ₁₂ and Z ₁₃ represent an atomic group necessary for completing an aromatic ring, and R ₁₁ , R ₁₂ and R ₁₃ each independently represent an alkyl group, an alkyloxy group, an aryloxy group or a halogen atom. , R ₁₄ , R ₁₅ and R ₁₆ each independently represent a hydrogen atom or a monovalent substituent, and l, m and n each independently represent 0 to 7. (2) In the general formula (1), R ₁₄ , R ₁₅ , and R ₁₆ are each an alkyl group or a halogen atom, and the organic electroluminescence device according to (1) above. (3) The organic electroluminescent device as described in (1) or (2) above, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).

[0008]

[Chemical 5] In the formula, B represents a boron atom, C represents a carbon atom, and A
_{twenty one}, A_{twenty two}, A_{twenty three}, A_{twenty four}, A_{twenty five}And A₂₆Is a carbon atom
Represents a nitrogen atom, Z_{twenty one}, Z_{twenty two}And Z_{twenty three}Completes the aromatic ring
Represents the atomic group required to form_{twenty one}, R_{twenty two}, R_{twenty three}, R
_{twenty four}, R_{twenty five}And R₂₆Are each independently an alkyl group,
A kyloxy group, an aryloxy group or a halogen atom
Represent, R₂₇, R₂₈And R₂₉Are each independently a hydrogen atom
Or represents a monovalent substituent,₂, M₂And n₂Is it
Each represents 0 to 7 independently. (4) In the general formula (1) or the general formula (2),
Z₁₁, Z₁₂, Z₁₃, Z_{twenty one}, Z _{twenty two}And Z_{twenty three}Formed by
Characterized in that the aromatic ring formed is an aromatic hydrocarbon ring
The organic elect according to any one of (1) to (3) above
Luminescence element. (5) The compound represented by the general formula (1) has the following general formula:
The above, which is a compound represented by (3)
The organic electroluminescence according to (1) or (2).
Element.

[0009]

[Chemical 6] In the formula, B represents a boron atom and R₃₁, R₃₅, R₄₁,
R₄₅, R₅₁And R₅₅Is an alkyl group or halogen atom
Represents R₃₂, R₃₃, R₃₄, R₄₂, R₄₃, R₄₄, R ₅₂,
R₅₃And R₅₄Represents a hydrogen atom or a monovalent substituent.
However, R₃₂, R₃₃, R₃₄At least one of R₄₂, R
₄₃, R₄₄At least one of R₅₂, R₅₃And R₅₄Small
At least one kind is an aromatic ring group. (6) Chemical formula represented by the general formula (1), (2) or (3)
The compound band gap is 2.96 eV to 3.80 eV
In any of the above (1) to (5), characterized in that
The organic electroluminescence device described. (7) Chemical formula represented by the general formula (1), (2) or (3)
The band gap of the compound is 3.20 eV to 3.60 eV
In any one of the above (1) to (6),
The organic electroluminescence device described. (8) Chemical formula represented by the general formula (1), (2) or (3)
The compound is contained in the light emitting layer,
The organic electroluminescence according to any one of (1) to (7).
Ness element. (9) Chemical formula represented by the general formula (1), (2) or (3)
In addition, the compound is contained in the electron transport layer.
The organic electroluminescence according to any one of (1) to (8)
Luminescence element. (10) A cathode buffer layer is provided between the cathode and the electron transport layer.
Any of the above (1) to (9) characterized by having
The organic electroluminescence device described in 1. (11) Organic according to any one of (1) to (10) above
Characterized by having an electroluminescence element
Display device. (12) At least one is in any one of Claims 1-10.
The described organic electroluminescence device,
Two or more types of organic electroluminescence that emit light of the maximum wavelength
The luminescent elements are arranged side by side on the same substrate.
The display device according to (11) above. (13) Organic according to any one of (1) to (10) above
Electroluminescence element and the organic electroluminescence
Absorbs the light emitted by the luminescence element and is different from it
Characterized by having a color conversion layer that emits light of maximum wavelength
Display device. (14) Two or more color changes that emit different maximum wavelengths of light
The replacement layers are juxtaposed on the same substrate.
The display device according to item (13).

The present invention will be described in detail below. First, the compound represented by the general formula (1) used in the organic electroluminescent device of the present invention will be described.
In the general formula (1), B represents a boron atom, C represents a carbon atom, A ₁₁ , A ₁₂ and A ₁₃ represent a carbon atom or a nitrogen atom, and Z ₁₁ , Z ₁₂ and Z ₁₃ represent an aromatic ring. Represents an atomic group necessary for completion, R ₁₁ , R ₁₂ and R ₁₃ each independently represent an alkyl group, an alkyloxy group, an aryloxy group or a halogen atom, and R ₁₄ , R ₁₅ and R ₁₆ each independently Represents a hydrogen atom or a monovalent substituent, and l, n and m each independently represent 0 to 7.
In the general formula (1), a carbon atom, A ₁₁ and Z ₁₁ , a carbon atom, and A ₁₂ and Z ₁₂ are a carbon atom,
The aromatic ring formed by A ₁₃ and Z ₁₃ is a ring in which the number of π electrons satisfies 4n + 2 [n is a natural number], and may be an aromatic hydrocarbon ring or an aromatic heterocycle. Representative examples of the aromatic ring satisfying the number of π electrons of 4n + 2 [n is a natural number] are benzene ring, naphthalene ring, anthracene ring, azulene ring, phenanthrene ring, triphenylene ring, pyrene ring, chrysene ring, naphthacene ring and perylene ring. , Pentacene ring, hexacene ring, coronene ring, trinaphthylene ring,
Furan ring, thiophene ring, pyrrole ring, imidazole ring, pyrazole ring, 1,2,4-triazole ring, 1,
2,3-triazole ring, oxazole ring, thiazole ring, isoxazole ring, isothiazole ring, furazan ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, indolizine ring, quinoline ring, isoindole ring, indole ring, Examples thereof include isoquinoline ring, phthalazine ring, purine ring, naphthyridine ring, quinoxaline ring, quinazoline ring, cinnoline ring, pteridine ring, carbazole ring, phenanthridine ring, acridine ring, perimidine ring, phenanthroline ring and phenazine ring.

R₁₁, R₁₂And R₁₃Alkyl represented by
Examples of the group include a methyl group, an ethyl group and i-propyl group.
Group, hydroxyethyl group, methoxymethyl group, trif
Luoromethyl group, t-butyl group, cyclopentyl group,
Examples thereof include chlorhexyl group and benzyl group.
Examples of the xy group include methoxy group, ethoxy group, i
-Propoxy group, butoxy group, etc.
Examples of the xy group include a phenoxy group and the like,
Halogen atoms include fluorine, chlorine and bromine
Child, iodine atom and the like. R₁₁, R₁₂And R₁₃
Is preferably an alkyl group or a halogen atom,
In addition, methyl group, ethyl group, isopropyl group or fluorine group
Elemental atoms are preferred. R₁₄, R₁₅And R₁₆Represented by
The valent substituent is not particularly limited, for example,
R₁₁, R₁₂And R₁₃Alkyl group shown in the explanation of
Of a killoxy group, an aryloxy group and a halogen atom
In addition, aryl groups (eg, phenyl group, naphthyl group,
p-tolyl group, p-chlorophenyl group, etc.), alkyl group
Group (eg, methylthio group, ethylthio group, i-pro group
Pilthio group, etc., arylthio group (eg, phenylthio group)
Group, etc.), cyano group, nitro group, heterocyclic group (eg,
Roll group, pyrrolidyl group, pyrazolyl group, imidazolyl
Group, pyridyl group, benzimidazolyl group, benzthiazo
Ryl group, benzoxazolyl group, etc.) and the like.
When each of l, m and n is 2 or more, each R
₁₄, R₁₅And R ₁₆May be the same or different. Well
Further, the compound represented by the general formula (1) is a boron atom.
Aromatic ring group bonded to, for example, a boron atom bonded
A carbon atom adjacent to a carbon atom is directly or through a substituent
And bond to form a ring containing a boron atom
Also included are compounds. Specifically, the following structure is adopted.
May be.

[0012]

[Chemical 7] (In the formula, R ₆₁ and R ₆₂ have the same meanings as R ₁₁ , R ₁₂ and R _13. )

Next, the organic electroluminescence of the present invention
The compound represented by the general formula (2) used for the sensor element.
Describe the thing. In the general formula (2), B is a ho
Represents an elementary atom, C represents a carbon atom, and A_{twenty one}, A_{twenty two},
A_{twenty three}, A_{twenty four}, A_{twenty five}And A₂₆Is a carbon atom or a nitrogen atom
Represents Z_{twenty one}, Z _{twenty two}And Z_{twenty three}To complete the aromatic ring
Represents a necessary atomic group, R_{twenty one}, R_{twenty two}, R_{twenty three}, R_{twenty four}, R_{twenty five}Oh
And R₂₆Are each independently an alkyl group, alkyloxy
A group, an aryloxy group or a halogen atom,
R₂₇, R₂₈And R₂₉Are each independently a hydrogen atom or
Represents a monovalent substituent,₂, N₂And m₂Each is German
It stands for 0 to 7. In the general formula (2), a carbon atom,
A_{twenty one}, A_{twenty two}And Z_{twenty one}Depending on the carbon atom, A_{twenty three}, A_{twenty four}
And Z_{twenty two}Depending on the carbon atom, A_{twenty five}, A₂₆And Z_{twenty three}
The aromatic ring formed by
And carbon atom, A₁₁And Z₁₁By a carbon atom,
A₁₂And Z₁₂Depending on the carbon atom, A₁₃And Z₁₃To
Therefore, the aromatic ring shown in the description of the aromatic ring formed is
Be done. R_{twenty one}, R_{twenty two}, R_{twenty three}, R_{twenty four}, R_{twenty five}And R₂₆Represented by
Alkyl group, alkyloxy group, aryloxy group
Alternatively, as the halogen atom, in the general formula (1),
R₁₁, R₁₂And R₁₃Alkyl group shown in the explanation of
Examples include a killoxy group, an aryloxy group, and a halogen atom.
To be R₂₇, R₂₈And R₂₉Monovalent substituent represented by
In the general formula (1)₁₄, R₁₅And R
₁₆The monovalent substituents shown in the explanation of are mentioned. l₂, M₂
And n₂When each is 2 or more, each R₂₇,
R₂₈And R₂₉May be the same or different. Also,
R₂₇, R₂₈And R₂₉Are fused together to form a ring
May be In the general formula (2), preferably
Is R_{twenty one}, R_{twenty two}, R_{twenty three}, R_{twenty four}, R_{twenty five}And R ₂₆Is Archi
Group or halogen atom, and more preferably,
Chill group, ethyl group, isopropyl group or fluorine atom
Yes, Z_{twenty one}, Z_{twenty two}And Z_{twenty three}The aromatic ring completed by
This is when it is an aromatic hydrocarbon ring.

Next, the organic electroluminescence of the present invention
The compound represented by the general formula (3) used for the sensor element.
Describe the thing. In the general formula (3), B is a ho
Represents an elementary atom, R₃₁, R₃₅, R₄₁, R₄₅, R ₅₁And R
₅₅Represents an alkyl group or a halogen atom, R₃₂,
R₃₃, R₃₄, R₄₂, R₄₃, R₄₄, R₅₂, R₅₃And R₅₄
Represents a hydrogen atom or a monovalent substituent. However, R₃₂,
R₃₃, R₃₄At least one of R₄₂, R₄₃, R₄₄Little
At least one, R₅₂, R₅₃And R₅₄At least one of
It is an aromatic ring group. In the general formula (3), R₃₁, R₃₅,
R₄₁, R₄₅, R₅₁And R₅₅An alkyl group represented by
In the general formula (1), the Rogen atom is R₁₁, R
₁₂And R₁₃Alkyl group and halogen atom shown in the explanation of
Is mentioned. R₃₂, R₃₃, R₃₄, R₄₂, R₄₃, R₄₄,
R₅₂, R₅₃And R₅₄As a monovalent substituent represented by
Is R in the general formula (1).₁₄, R₁₅And R₁₆Theory of
The monovalent substituents shown in the above can be mentioned. R₃₂, R₃₃, R
₃₄At least one of R₄₂, R₄₃, R₄₄At least one of
Seed, R ₅₂, R₅₃And R₅₄At least one kind of aromatic ring group
However, as these aromatic ring groups, the number of π electrons is 4n.
Any of compounds having a ring satisfying +2 [n is a natural number]
One hydrogen atom is removed from the position. Ring is good
It may be an aromatic hydrocarbon ring or an aromatic heterocycle. Number of π electrons
Is 4n + 2 [n is a natural number]
Benzene, naphthalene, anthracene, azure
N, phenanthrene, triphenylene, pyrene, chrysene
, Naphthacene, perylene, pentacene, hexacene,
Coronene, trinaphthylene, furan, thiophene, pyro
, Imidazole, pyrazole, 1,2,4-tria
Sol, 1,2,3-triazole, oxazole, thi
Azole, isoxazole, isothiazole, flaza
, Pyridine, pyrazine, pyrimidine, pyridazine, a
Ndridine, quinoline, isoindole, indole,
Isoquinoline, phthalazine, purine, naphthyridine, chi
Noxaline, quinazoline, cinnoline, pteridine, mosquito
Lubazole, phenanthridine, acridine, perimidii
And phenanthroline, phenazine and the like. Well
In addition, these may have any substituents,
May have fused rings in which a number of substituents are fused together
Yes.

The compounds represented by the general formulas (1), (2) and (3) used in the organic electroluminescence device of the present invention have a band gap of 2.96 eV to 3.
The compound is preferably 80 eV, more preferably 3.20 eV to 3.60 eV. When the band gap is within the above range, the hole blocking property is improved while maintaining the electron transport property, and the light emission efficiency can be further improved.

The band gap represents the difference between the ionization potential and the electron affinity of a compound, and the ionization potential and the electron affinity are determined with the vacuum level as a reference. The ionization potential is defined as the energy required to release the electron at the HOMO (highest occupied molecular orbital) level of the compound to the vacuum level, and the electron affinity is the LUMO of the electron at the vacuum level (lowest unoccupied molecule) (Orbit) defined as the energy that falls to the level and stabilizes. In addition,
The difference between the ionization potential and the electron affinity can be converted from the absorption edge of the absorption spectrum of the compound. In the present invention, the absorption spectrum of the vapor deposition film when the compound is vapor-deposited on glass to 100 nm is measured, and The wavelength Ynm at the absorption edge was converted to XeV. At this time,
The following conversion formula was used. Specific examples of the compounds represented by the general formulas (1) to (3) (hereinafter, sometimes referred to as the compound of the present invention) are shown below at X = 1240 / Y. The compounds usable in the present invention are It is not limited to these.

[0017]

[Chemical 8]

[0018]

[Chemical 9]

[0019]

[Chemical 10]

[0020]

[Chemical 11]

[0021]

[Chemical 12]

Synthetic Example Compound I-13 [tris (biphenyldury
l) synthesis of borane]

[0023]

[Chemical 13] tri (bromoduryl) borane (Or
g. Lett. , 2000, 4129) 0.
65 g, biphenyl-4-yl-boronic
acid (J. Chem. Soc., 1966, 566).
0.65 g, K ₂ CO ₃ 0.75 g, Pd
150 ml of THF solution containing 0.15 g of (PPh ₃ ) ₄ was refluxed for 4 hours, and the obtained crude product was purified by silica gel column chromatography and recrystallization method to give compound I
0.43 g of -13 was obtained. The structure was identified by NMR and mass spectra.

The compound of the present invention is a compound having strong fluorescence in the solid state and is excellent in electroluminescence.
It can be effectively used as a light emitting material. In addition, since it is very excellent in the electron injection property and the electron transport property from the metal electrode, when it is used as an electron transport material in an element using another light emitting material, excellent luminous efficiency can be obtained.
The organic EL device of the present invention has a hole transport layer, an electron transport layer, an anode buffer layer, a cathode buffer layer, etc., if necessary, in addition to the light emitting layer, and has a structure sandwiched between a cathode and an anode. You can Specifically, the following structures are given as examples. (I) Anode / light emitting layer / cathode (ii) Anode / hole transport layer / light emitting layer / cathode (iii) Anode / light emitting layer / electron transport layer / cathode (iv) Anode / hole transport layer / light emitting layer / electron Transport layer / cathode (v) anode / anode buffer layer / hole transport layer / light emitting layer /
Electron Transport Layer / Cathode Buffer Layer / Cathode The compound of the present invention may be contained in any layer, but is preferably contained in the light emitting layer or the electron transport layer, and contained in the electron transport layer. Is particularly preferable.

The light emitting layer is a layer which emits light by recombination of electrons and holes injected from the electrode, the electron transporting layer or the hole transporting layer, and the light emitting portion is even in the layer of the light emitting layer. It may be the interface between the light emitting layer and the adjacent layer. The material used for the light emitting layer (hereinafter referred to as the light emitting material) is preferably an organic compound or complex that emits fluorescence or phosphorescence. Besides the compound of the present invention, it is used for the light emitting layer of an organic EL device. It can be appropriately selected and used from known ones. Such a light emitting material is mainly an organic compound, and depending on a desired color tone, for example, Macromol.
Synth. , 125, pp. 17-25, and the like. The light emitting material may have a hole transporting function and an electron transporting function in addition to the light emitting performance, and most of the hole transporting material and the electron transporting material can also be used as the light emitting material. The luminescent material may be a polymeric material such as p-polyphenylene vinylene or polyfluorene,
Further, a material in which the light emitting material is introduced into a polymer chain, or a polymer material in which the light emitting material has a polymer main chain may be used.

Further, a dopant (guest substance) may be used in combination in the light emitting layer, and an arbitrary one may be selected and used from the publicly known ones used as the dopant of the EL element. Specific examples of the dopant include quinacridone, DCM, coumarin derivative, rhodamine, rubrene, decacyclene, pyrazoline derivative, squarylium derivative, europium complex, iridium complex, platinum complex and the like. The light emitting layer can be formed by forming the above compound into a film by a known thinning method such as a vacuum vapor deposition method, a spin coating method, a casting method, and an LB method. The thickness of the light emitting layer is not particularly limited, but is usually selected in the range of 5 nm to 5 μm. The light emitting layer may have a single-layer structure composed of one or more of these light-emitting materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions. Further, as described in JP-A-57-51781, the light emitting layer is formed into a solution by dissolving the above light emitting material in a solvent together with a binder such as a resin, and then forming a thin film by spin coating or the like. It can be formed by converting. When the organic electroluminescence device of the present invention has a color conversion layer, it is preferable that the light emitted from the light emitting layer is light in the blue-violet region from the viewpoint of conversion efficiency.
Light in the blue-violet region is measured with a measuring instrument such as a spectral radiance meter CS-1000 (manufactured by Minolta), and the coordinates are CIE chromaticity coordinates (“New Color Science Handbook” (edited by the Japan Color Association,
When referring to FIG. 4.16) on page 108 of the University of Tokyo Press, 1985), it refers to light in the area of Purpurish Blue (purple blue) or Bluish Purple (purple blue).

As a general feature, the maximum fluorescence wavelength in a solution of a compound exhibiting blue-violet emission is 350 nm.
Those having a wavelength of 420 nm or less are preferable, and those having a fluorescence quantum yield of 0.1 or more are preferable. Specific examples of such a light emitting material are described in Japanese Patent Application No. 11-365996 (corresponding EP published: EP1067165A) and Japanese Patent Application No. 2000-.
265045, Japanese Patent Application No. 2000-285050, Japanese Patent Application No. 2000-292124, Japanese Patent Application 2
000-290466, Japanese Patent Application No. 11-3419
23, Japanese Patent Application No. 11-265312, Japanese Patent Application No. 11-274848, Japanese Patent Application 2000-24.
No. 0880, Japanese Patent Application No. 2000-345267 and the like. Some of the above specific examples are shown below, but the light emitting material used in the present invention is not limited thereto.

[0028]

[Chemical 14]

[0029]

[Chemical 15]

[0030]

[Chemical 16]

[0031]

[Chemical 17]

[0032]

[Chemical 18]

[0033]

[Chemical 19]

Next, the hole transport layer and the electron transport layer will be described. The hole transport layer has a function of transmitting holes injected from the anode to the light emitting layer, and by interposing the hole transport layer between the anode and the light emitting layer, many holes are generated at a lower electric field. It is injected into the light emitting layer. Besides, the light emitting layer has a cathode,
Electrons injected from the cathode buffer layer or the electron transport layer are accumulated at the interface of the light emitting layer and the hole transport layer due to the barrier of electrons existing at the interface, and the light emitting efficiency is improved. It becomes an element. The material for the hole transport layer (hereinafter referred to as the hole injection material or the hole transport material) is not particularly limited as long as it has the above-mentioned preferable properties, and conventionally, in the optical transmission material, the Any material can be selected and used from the materials commonly used as the charge injection / transport material and the known materials used for the hole transport layer of the EL element. The hole transport material has one of hole injection or transport and electron barrier properties, and may be an organic substance or an inorganic substance. Examples of the hole transport material include a triazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, a pyrazoline derivative and a pyrazolone derivative, a phenylenediamine derivative, an arylamine derivative, an amino-substituted chalcone derivative, an oxazole derivative, and a styrylanthracene. Examples thereof include derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, especially thiophene oligomers.
As the hole transport material, any of the above materials can be used, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.

Typical examples of aromatic tertiary amine compounds and styrylamine compounds are N, N, N ', N'-tetraphenyl-4,4'-diaminophenyl; N, N'.
-Diphenyl-N, N'-bis (3-methylphenyl)
-(1,1'-biphenyl) -4,4'-diamine (T
PD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ', N'-
Tetra-p-tolyl-4,4'-diaminophenyl;
1,1-bis (4-di-p-tolylaminophenyl)-
4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-
Di-p-tolylaminophenyl) phenylmethane; N,
N'-diphenyl-N, N'-di (4-methoxyphenyl) -4,4'-diaminobiphenyl; N, N, N ',
N'-Tetraphenyl-4,4'-diaminodiphenyl ether; 4,4'-bis (diphenylamino) quadriphenyl; N, N, N-tri (p-tolyl) amine; 4- (di-p-tolylamino) ) -4 '-[4- (Di-p-tolylamino) styryl] stilbene; 4-N,
N-diphenylamino- (2-diphenylvinyl) benzene; 3-methoxy-4′-N, N-diphenylaminostilbenzene; N-phenylcarbazole, and further described in US Pat. No. 5,061,569. Having two condensed aromatic rings described in the molecule, for example, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), JP-A-4-308.
No. 688, 4,4 ′, in which three triphenylamine units are linked in a starburst type,
4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (MTDATA) and the like. Further, these compounds are introduced into a polymer chain, or these compounds are It is also possible to use a polymer material having a main chain of a molecule.
Inorganic compounds such as p-type-SiC can also be used as the hole transport material. The hole transport layer can be formed by forming the above hole transport material into a thin film by a known method such as a vacuum vapor deposition method, a spin coating method, a casting method, and an LB method. The thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 μm.
The hole-transporting layer may have a single-layer structure composed of one or more of the above materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.

The electron transport layer has only to have a function of transmitting the electrons injected from the cathode to the light emitting layer, and as the material thereof, any one selected from conventionally known compounds can be used. it can. Examples of materials used for the electron transport layer (hereinafter referred to as electron transport materials) include, in addition to the compounds of the present invention, heterocycles such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, and naphthaleneperylene. Examples include tetracarboxylic acid anhydride, carbodiimide, fluorenylidene methane derivative, anthraquinodimethane and anthrone derivative, oxadiazole derivative, triazole derivative, phenanthroline derivative. Furthermore, in the above oxadiazole derivative, a thiadiazole derivative in which an oxygen atom of the oxadiazole ring is substituted with a sulfur atom, or a quinoxaline derivative having a quinoxaline ring known as an electron-withdrawing group can also be used as the electron transport material. Further, it is also possible to use a polymer material in which these materials are introduced into a polymer chain or where these materials are used as a polymer main chain. In addition, a metal complex of an 8-quinolinol derivative,
For example, tris (8-quinolinol) aluminum (A
1q), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum, tris (2-methyl-8-).
Quinolinol) aluminum, tris (5-methyl-8)
-Quinolinol) aluminum, bis (8-quinolinol) zinc (Znq) and the like, and metal complexes in which the central metal of these metal complexes is replaced with In, Mg, Cu, Ca, Sn, Ga or Pb are also used as electron transport materials. be able to. In addition, metal-free or metal phthalocyanine, or those whose terminal is substituted with an alkyl group, a sulfonic acid group or the like can be preferably used as the electron transport material. Further, the distyrylpyrazine derivative used as the material of the light emitting layer can also be used as the electron transporting material, and an inorganic semiconductor such as n-type-Si or n-type-SiC can also be used as the electron transporting material as in the hole transporting layer. Can be used. The electron transport layer can be formed by forming the above compound into a film by a known thinning method such as a vacuum deposition method, a spin coating method, a casting method, and an LB method. The thickness of the electron transport layer is not particularly limited, but is usually selected in the range of 5 nm to 5 μm. The electron-transporting layer may have a single-layered structure composed of one or more kinds of electron-transporting materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.

Further, a buffer layer (electrode interface layer) may be present between the anode and the light emitting layer or the hole transport layer or between the cathode and the light emitting layer or the electron transport layer. The buffer layer is a layer provided between the electrode and the organic layer in order to reduce the driving voltage and improve the light emission efficiency. “The organic EL device and its industrial front line (November 30, 1998, NT・ Published by Essha Co., Ltd.), Chapter 2 "Electrode Materials" (Chapter 12)
Pages 3 to 166), the buffer layer includes an anode buffer layer and a cathode buffer layer. The details of the anode buffer layer are described in JP-A-9-45479, JP-A-9-260062, JP-A-8-288069, and the like.
A phthalocyanine buffer layer typified by copper phthalocyanine, an oxide buffer layer typified by vanadium oxide, an amorphous carbon buffer layer, a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene, and the like. . The cathode buffer layer is described in JP-A-6-325871 and 9-1.
The details are also described in Japanese Patent Nos. 7574, 10-74586, and the like, and specifically, a metal buffer layer typified by strontium, aluminum, and the like, an alkali metal compound buffer layer typified by lithium fluoride,
Examples thereof include an alkaline earth metal compound buffer layer typified by magnesium fluoride and an oxide buffer layer typified by aluminum oxide. In particular, the organic EL of the present invention
In the device, when the cathode buffer layer was present, a large reduction in driving voltage and improvement in luminous efficiency were obtained. The buffer layer is preferably a very thin film, and the film thickness is preferably in the range of 0.1 to 100 nm, although it depends on the material. Further, in addition to the above-mentioned basic constituent layers, a layer having other functions may be laminated if necessary. Frontline ”(1998
It may have a functional layer such as a hole blocking (hole blocking) layer described on page 237, etc. of November 30, published by NTS Co., Ltd.).

Next, the electrodes will be described. The electrodes of the organic EL element consist of a cathode and an anode. As the anode, an anode using a metal, an alloy, an electrically conductive compound having a large work function (4 eV or more) and a mixture thereof as an electrode substance is preferable. Specific examples of such an electrode material include metals such as Au, CuI, indium tin oxide (ITO), and Sn.
Conductive transparent materials such as O ₂ and ZnO are mentioned. The anode can be obtained by forming a thin film of these electrode substances by a method such as vapor deposition or sputtering and forming a pattern having a desired shape by a photolithography method. Further, when the pattern accuracy is not required so much (about 100 μm or more), the electrode material may be vapor-deposited through a mask having a desired shape or may be sputtered to form the pattern. When the emitted light is taken out from the anode, the light transmittance of the anode is preferably higher than 10%, and the sheet resistance of the anode is preferably several hundred Ω / □ or less. The thickness of the anode depends on the material, but is usually 10 nm to 1
μm, preferably 10 nm to 200 nm. On the other hand, the cathode has a low work function (4 eV or less)
A metal (hereinafter, referred to as an electron injecting metal), an alloy, an electrically conductive compound, or a mixture thereof is used as an electrode material. Specific examples of such an electrode material include:
Sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) mixture, indium, lithium /
Examples include aluminum mixtures and rare earth metals. Of these, a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than that of the electron injecting metal, for example, a magnesium / silver mixture, from the viewpoint of electron injecting property and durability against oxidation and the like. Magnesium / aluminum mixture, magnesium / indium mixture, aluminum /
Aluminum oxide (Al ₂ O ₃ ) mixtures, lithium / aluminum mixtures and the like are suitable. Further, as the cathode used in the organic EL device of the present invention, an aluminum alloy is preferable, and particularly, the aluminum content is 90% by mass or more and less than 100% by mass, and most preferably 95% by mass or more and 10% by mass or more.
Aluminum alloys of less than 0% by weight are preferred. By using these aluminum alloys, it is possible to greatly improve the light emission life and the ultimate brightness of the organic EL element. The cathode is formed by a method such as vapor deposition or sputtering.
It can be produced by forming a thin film of the above electrode substance. The sheet resistance of the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually 10 nm to 1 μm, preferably 50.
Is selected in the range of up to 200 nm. In order to transmit and take out the emitted light, it is convenient that either the anode or the cathode of the organic EL element is transparent or semi-transparent so that the emission efficiency is improved.

The organic EL device of the present invention is usually formed on a substrate. The substrate preferably used is glass, plastic or the like, and the type thereof is not particularly limited. In addition, a transparent substrate is used when the substrate is required to have optical transparency. The substrate preferably used in the electroluminescent element of the present invention, for example, a glass plate,
Examples thereof include a quartz plate and a plastic film.
Examples of the light-transmissive plastic film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyether sulfone (PE).
S), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.

Next, the method for producing an organic EL device of the present invention will be described.
Anode / Anode buffer layer / Hole transport layer / Emission mentioned above
Layer / electron transport layer / cathode buffer layer / cathode organic
An EL element will be described below as an example. Have other structure
The organic EL device of the present invention can be easily manufactured by referring to the following description.
Can be made. First, from the anode material on the substrate
Thin film of 1 μm or less, preferably 10-200 nm
For example, evaporation or spatter
Then, the anode is formed by a method such as the method described above. Then this
Anode buffer layer, hole transport layer, light emitting layer, electron transport on top
Layer and cathode buffer layer
It As a method for forming these thin films, the spin
There are coating method, casting method, vapor deposition method, etc., but a homogeneous film
Is easy to obtain, and pinholes are hard to generate, etc.
In view of the above, the vacuum deposition method or the spin coating method is preferable.
Yes. To form these layers, different film forming methods are used for each layer.
May be used. When forming a film using the vapor deposition method, vapor deposition
The conditions depend on the type of compound used and the purpose of the molecular deposition film.
Generally, it depends on the crystal structure, association structure, etc.
Is a boat heating temperature of 50 to 450 ° C. and a vacuum degree of 10 ^-6~ 1
0^-2Pa, evaporation rate 0.01 to 50 nm / sec, substrate temperature
Appropriately selected in the range of -50 to 300 ° C and film thickness of 5 nm to 5 μm.
It is desirable to wear After forming these layers,
A thin film made of a cathode material is 1 μm or less, preferably 50
Vapor deposition to obtain a film thickness in the range of up to 200 nm.
And the cathode is formed by a method such as sputtering
As a result, a desired EL element can be obtained. Organic EL element
Is a consistent vacuum from one hole transport layer to the cathode.
It is preferable to make it, but take it out in the middle and make a different film
You may apply the law. However, in that case, dry the work
It is necessary to consider such things as dry atmosphere of inert gas. Well
In addition, reverse the order of production to replace the cathode, cathode buffer layer, and
Child transport layer, light emitting layer, hole transport layer, anode buffer layer, positive
It is also possible to fabricate in the order of the poles. Get in this way
In the organic EL device thus prepared, the anode has a positive polarity and the cathode has a negative polarity.
When a direct current voltage of about 5 to 40 V is applied,
Can be observed. Moreover, even if voltage is applied with the opposite polarity, the current is
It does not flow and no light emission occurs. In addition, apply AC voltage
If the anode is +, the cathode is-
Only emits light. The AC waveform to be applied may be arbitrary.
Yes.

The organic EL device of the present invention may be used as a kind of lamp for lighting or as an exposure light source, or may be a projection device of a type for projecting an image or a type for directly visually recognizing a still image or a moving image. It may be used as a display device (display). When used as a display device for reproducing a moving image, the drive system may be either a simple matrix (passive matrix) system or an active matrix system. Further, by using two or more kinds of the organic EL elements of the present invention having different emission colors, it is possible to make a full-color display device.

Next, the color conversion layer will be described. The color conversion layer is a layer having a function of converting light of a certain wavelength into light of a different wavelength, and specifically, the layer absorbs light emitted from the light emitting layer of the organic EL element and is different from that. It contains a substance that emits light of the maximum wavelength. By the color conversion layer,
It is possible to display not only the color emitted by the light emitting layer of the organic EL element but also other colors. Examples of the substance that absorbs the light emitted by the light-emitting layer of the organic EL element and emits light having a wavelength different from that include a phosphor, and the phosphor may be either an organic phosphor or an inorganic phosphor. It can be used according to the wavelength you want. Examples of organic phosphors include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squarylium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes, Examples include stilbene dyes and polythiophene dyes.

The inorganic phosphors are preferably fine particles having a particle size of 3 μm or less, and more preferably ultra-fine particle phosphors which are synthesized by a liquid phase method and are nearly monodisperse. Examples of the inorganic phosphor include an inorganic phosphor composed of a crystal matrix and an activator, and a rare earth complex phosphor. The composition of the inorganic phosphor is not particularly limited, but it is Y ₂ O ₂ S which is a crystal matrix.
, Zn ₂ SiO ₄ , Ca ₅ (PO ₄ ) ₃ Cl, and other metal oxides, and ZnS, SrS, CaS, and other sulfides include Ce, Pr, Nd, Pm, Sm, Eu, Gd,
A combination of rare earth metal ions such as Tb, Dy, Ho, Er, Tm, and Yb and metal ions such as Ag, Al, Mn, In, Cu, and Sb as an activator or coactivator is preferable. The crystal matrix is preferably a metal oxide, for example, (X) ₃ Al ₁₆ O ₂₇ , (X) ₄ Al ₁₄ O ₂₅ ,
(X) ₃ Al ₂ Si ₂ O ₁₀ , (X) ₄ Si ₂ O ₈ , (X) ₂ S
i ₂ O ₆ , (X) ₂ P ₂ O ₇ , (X) ₂ P ₂ O ₅ , (X) ₅ (P
O ₄ ) ₃ Cl, (X) ₂ Si ₃ O ₈ ^-2 (X) Cl ₂ [where
X represents an alkaline earth metal. The alkaline earth metal represented by X may be a single component or a mixed component of two or more kinds, and the mixing ratio thereof is arbitrary. ] Alkaline earth metal substituted aluminum oxide, silicon oxide,
Phosphoric acid, halophosphoric acid, etc. are mentioned as a typical crystal matrix. Other preferred crystal bases include oxides and sulfides of zinc, oxides of rare earth metals such as yttrium, gadolinium and lanthanum, and partial sulfides obtained by replacing a part of oxygen of the oxides with sulfur atoms, rare earth metals. Sulfide,
In addition, a mixture of an oxide or a sulfide of a rare earth metal with an arbitrary metal element may be used.

Preferred examples of the crystal matrix are listed below. Mg_FourGeO_5.5F, Mg_FourGeO₆, ZnS, Y₂O₂S,
Y₃Al_FiveO₁₂, Y₂SiO_Ten, Zn₂SiO_Four , Y₂O₃,
BaMgAl_TenO₁₇, BaAl₁₂O₁₉, (Ba, Sr,
Mg) O ・ aAl₂O₃, (Y, Gd) BO₃, (Zn,
Cd) S, SrGa₂S_Four, SrS, GaS, SnO₂,
Ca_Ten(PO_Four)₆(F, Cl)₂, (Ba, Sr) (M
g, Mn) Al_TenO₁₇, (Sr, Ca, Ba, Mg)_Ten
(PO _Four)₆Cl₂, (La, Ce) PO_Four, CeMgAl
₁₁O₁₉, GdMgB_FiveO_Ten, Sr₂P₂O₇, Sr_FourAl₁₄
O_{twenty five}, Y₂SO_Four, Gd₂O₂S, Gd₂O₃, YVO_Four, Y
(P, V) O_Fouretc The crystal matrix and the activator or co-activator are combined with a homologous element.
It may be a partial replacement. There is no limit to the elemental composition
In particular, those that emit visible light by absorbing light in the blue-violet region
Is preferred. In the present invention, an activator for an inorganic phosphor,
Preferred co-activators are La, Eu, Tb, C.
e, Yb, Pr, and other lanthanoid element io
Ions of metals such as nickel, Ag, Mn, Cu, In, and Al.
And the doping amount is 0.001 to 100 with respect to the base material.
Mol% is preferable, and 0.01 to 50 mol% is more preferable.
Good The activator and co-activator are ions of the crystal matrix.
Replace some with ions like the lanthanoids above.
And it is doped into the crystal.

Typical inorganic phosphors (crystal matrix and
Inorganic phosphor composed of activator)
However, the inorganic phosphor used in the present invention is not limited to these.
It is not fixed. (Ba_zMg_1-z)_3-xyAl₁₆O₂₇: Eu²⁺ _x, M
n_{2 + y}, Sr_4-xAl₁₄O_{twenty five}: Eu²⁺ _x, (Sr_1-zB
a_z)_1-xAl₂Si₂O₈: Eu²⁺ _x, Ba_2-xSiO_Four: E
u²⁺ _x, Sr_2-xSiO_Four: Eu²⁺ _x, Mg_2-xSiO_Four: E
u²⁺ _x, (BaSr)_1-xSiO_Four: Eu²⁺ _x, Y_2-xyS
iO_Five: Ce³⁺ _x, Tb³⁺ _y, Sr_2-xP₂O_Five: Eu²⁺ _x,
Sr_2-xP₂O₇: Eu²⁺ _x, (Ba_yCa_zMg_1-yz)_5-x
(PO_Four)₃Cl: Eu²⁺ _x, Sr_2-xSi₃O_8-xSrCl
₂: Eu²⁺ _x[X, y and z are each 1 or less
Represents a number. ] Specific examples of the inorganic phosphors preferably used in the present invention are shown below.
Examples are shown below, but inorganic phosphors that can be used in the present invention
Is not limited to these compounds. In addition, firefly
The exact composition of the photonic crystal is, if strictly stated, the above.
It is represented by such a composition formula, but the amount of the activator is
Since it often does not affect the fluorescence characteristics,
There are no special remarks on the notation of machine phosphors.
Unless, for example, Sr_4-xAl₁₄O_{twenty five}: Eu²⁺ _xIs Sr_Four
Al₁₄O_{twenty five}: Eu²⁺And the numerical value of x is not described.

[Blue emitting inorganic phosphor] (BL-1) Sr ₂ P ₂ O ₇ : Sn ⁴⁺ (BL-2) Sr ₄ Al ₁₄ O ₂₅ : Eu ²⁺ (BL-3) BaMgAl ₁₀ O ₁₇ : Eu ²⁺ (BL-4) SrGa ₂ S ₄ : Ce ³⁺ (BL-5) CaGa ₂ S ₄ : Ce ³⁺ (BL-6) (Ba, Sr) (Mg, Mn) Al ₁₀ O ₁₇ : Eu ²⁺ (BL-7) (Sr, Ca, Ba, Mg) ₁₀ (PO ₄ ) ₆ Cl ₂ : Eu ²⁺ (BL-8) BaAl ₂ SiO ₈ : Eu ²⁺ (BL-9) Sr ₂ P ₂ O ₇ : Eu ²⁺ (BL-10) Sr ₅ (PO ₄ ) ₃ Cl: Eu ²⁺ (BL-11) (Sr, Ca, Ba) ₅ (PO ₄ ) ₃ Cl: Eu ²⁺ (BL- _{12) BaMg 2 Al 16 O 27} : Eu 2+ (BL-13) (Ba, Ca) 5 (PO 4) 3 Cl: Eu 2+ (BL-14) Ba 3 MgSi 2 O ^{_{8: Eu 2+ (BL-15}} ) Sr 3 MgSi 2 O 8: Eu 2+

[Green-Emitting Inorganic Phosphor] (GL-1) (Ba, Mg) Al ₁₆ O ₂₇ : Eu ²⁺ , Mn ²⁺ (GL-2) Sr ₄ Al ₁₄ O ₂₅ : Eu ²⁺ (GL -3) (Sr, Ba) Al ₂ Si ₂ O ₈ : Eu ²⁺ (GL-4) (Ba, Mg) ₂ SiO ₄ : Eu ²⁺ (GL-5) Y ₂ SiO ₅ : Ce ³⁺ , Tb _{^{3+ (GL-6) Sr 2}} P 2 O 7 -Sr 2 B 2 O 5: Eu 2+ (GL-7) (Ba, Ca, Mg) 5 (PO 4) 3 Cl: Eu 2+ (GL- 8) Sr ₂ Si ₃ O ₈ -2SrCl ₂ : Eu ²⁺ (GL-9) Zr ₂ SiO ₄ , MgAl ₁₁ O ₁₉ : Ce ³⁺ , Tb ³⁺ (GL-10) Ba ₂ SiO ₄ : Eu ²⁺ (GL-11) Sr ₂ SiO ₄ : Eu ²⁺ (GL-12) (Ba, Sr) SiO ₄ : Eu ²⁺

[Red-Emitting Inorganic Phosphor] (RL-1) Y ₂ O ₂ S: Eu ³⁺ (RL-2) YAlO ₃ : Eu ³⁺ (RL-3) Ca ₂ Y ₂ (SiO ₄ ) ₆ : Eu ³⁺ (RL-4) LiY ₉ (SiO ₄ ) ₆ O ₂ : Eu ³⁺ (RL-5) YVO ₄ : Eu ³⁺ (RL-6) CaS: Eu ³⁺ (RL-7) Gd ₂ O ₃ : Eu ³⁺ (RL-8) Gd ₂ O ₂ S: Eu ³⁺ (RL-9) Y (P, V) O ₄ : Eu ³⁺ (RL-10) Mg ₄ GeO _5.5 F: Mn ^{4 _{+ (RL-11) Mg 4}} GeO 6: Mn 4+ (RL-12) K 5 Eu 2.5 (WO 4) 6.25 (RL-13) Na 5 Eu 2.5 (WO 4) 6.25 (RL-14) K 5 Eu _2.5 (MoO ₄ ) _6.25 (RL-15) Na ₅ Eu _2.5 (MoO ₄ ) _{6.25 The} above inorganic phosphor may be subjected to a surface modification treatment, if necessary. The reason for this is chemical treatment with a silane coupling agent or the like, physical treatment with addition of submicron-order fine particles or the like, and further a combination thereof.

As the rare earth complex type phosphor, rare earth metals such as Ce, Pr, Nd, Pm, Sm, Eu, Gd and T are used.
Examples thereof include those having b, Dy, Ho, Er, Tm, Yb and the like. The organic ligand forming the complex may be either an aromatic type or a non-aromatic type, but the following general formula (B)
Compounds represented by are preferred. General formula (B) Xa- (Lx)-(Ly) n- (Lz) -Ya [In formula, Lx, Ly, Lz respectively independently represents the atom which has a 2 or more bond, n is 0 or Represents 1, X
a represents a substituent having an atom capable of coordinating to the adjacent position of Lx, and Ya represents a substituent having an atom capable of coordinating to the adjacent position of Lz. Further, any part of Xa and Lx may be condensed with each other to form a ring, any part of Ya and Lz may be condensed with each other to form a ring, and Lx and Lz may be condensed with each other. To form a ring, and at least one aromatic hydrocarbon ring or aromatic heterocycle exists in the molecule. However, Xa- (Lx)-(Ly) n- (L
z) -Ya is a β-diketone derivative, a β-ketoester derivative, a β-ketoamide derivative or a ketone in which the oxygen atom is replaced by a sulfur atom or —N (R ₂₀₁ ) —, crown ether, azacrown ether or thiacrown. The oxygen atom of the ether or crown ether may be any number of sulfur atoms or -N ( _R201 )-( _R201 is
It represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. In the case of a crown ether substituted with), an aromatic hydrocarbon ring or aromatic heterocycle may not be present in the molecule. In the general formula (B), the coordinable atom in Xa and Ya is specifically an oxygen atom, a nitrogen atom, a sulfur atom, a selenium atom or a tellurium atom, and particularly, an oxygen atom, a nitrogen atom, A sulfur atom is preferred. In formula (B), the atom having two or more bonds represented by Lx, Ly, and Lz is not particularly limited, but typically, carbon atom, oxygen atom, nitrogen atom, silicon atom, A titanium atom and the like can be mentioned, but a carbon atom is preferable. Specific examples of the rare earth complex-based phosphor preferably used in the present invention are shown below, but the rare earth complex-based phosphor that can be used in the present invention is not limited to these compounds.

[0050]

[Chemical 20]

[0051]

[Chemical 21]

[0052]

[Chemical formula 22]

[0053]

[Chemical formula 23]

[0054]

[Chemical formula 24]

The position where the color conversion layer is provided is not particularly limited as long as it can absorb the light emitted from the light emitting layer of the organic EL element, but it is between the transparent electrode and the transparent substrate or the transparent electrode of the transparent substrate. It is preferably provided on the side opposite to the side (the side from which emitted light is extracted). The color conversion layer is a layer in any form such as a layer formed by depositing a phosphor by vapor deposition or a sputtering method, a layer formed by applying a coating solution in which a phosphor is dispersed using a suitable resin as a binder. It doesn't matter. A suitable film thickness is about 100 nm to 5 mm. When a color conversion layer is obtained by applying a coating solution in which a phosphor is dispersed in a binder to form a film, the dispersed concentration of the phosphor in the binder does not cause concentration quenching of fluorescence and It is only necessary that the emission of light can be sufficiently absorbed.
Although it depends on the kind of the phosphor, it is suitable that the amount of the phosphor is 10 ⁻⁷ to 10 ⁻³ mol per 1 g of the resin used. In the case of an inorganic phosphor, concentration quenching is not a problem, so 0.1 to 10 g can be used per 1 g of resin. 400 to 50 as a color conversion layer when excited at the emission wavelength of the light emitting layer
A color conversion layer containing a phosphor that emits light having a maximum emission wavelength within a range of 0 nm, a phosphor that emits light having a maximum emission wavelength within a range of 501 to 600 nm when excited by the emission wavelength of the emission layer A color conversion layer containing a color conversion layer containing a phosphor that emits light having a maximum emission wavelength within the range of 601 to 700 nm when excited by the emission wavelength of the light emitting layer. Can be converted.

Next, the display device of the present invention having the organic electroluminescence element of the present invention will be described with reference to the drawings. FIG. 1 is a schematic diagram showing an example of a display device (display) including an organic electroluminescence element. The display device displays image information by the light emission of the organic electroluminescence element, and can be used as a display of a mobile phone or the like. The display 1 includes a display unit A having a plurality of pixels,
Control unit B for performing image scanning of display unit A based on image information
Etc. The control unit B is electrically connected to the display unit A, sends a scanning signal and an image data signal to the display unit A based on image information from the outside for each of a plurality of pixels, and scans sequentially selected by the scanning signal. Pixels on the line sequentially emit light according to the image data signal to display image information on the display unit A.

FIG. 2 is a schematic view of the display section. Display A
Has a wiring portion including a plurality of scanning lines 5 and a plurality of data lines 6 and a plurality of pixels 3 and the like on the substrate. Display A
The main members of the above will be described below. FIG. 2 shows a case where the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward). The plurality of scanning lines 5 and the plurality of data lines 6 of the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions (details). Is not shown.). When a scanning signal is applied to the scanning line 5, the pixel 3 receives an image data signal from the data line 6 and emits light according to the received image data. Full color display is possible by appropriately arranging pixels in the red region, pixels in the green region, and pixels in the blue region in the same color on the same substrate.

Next, the light emitting process of the pixel will be described. FIG. 3 is a schematic diagram of a pixel. The pixel is an organic electroluminescence element 10 and a switching transistor 1.
1, a drive transistor 12, a capacitor 13 and the like. Further, 5 is a scanning line, 6 is a data line, and 7 is a power supply line. In FIG. 3, an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6. Then, from the control unit B to the scanning line 5
When a scanning signal is applied to the gate of the switching transistor 11 via the, the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is transmitted to the capacitor 13 and the gate of the driving transistor 12. By transmitting the image data signal, the capacitor 13
Is charged according to the potential of the image data signal,
The drive of the drive transistor 12 is turned on. The drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic electroluminescence element 10. The drive transistor 12 is connected from the power supply line 7 to the organic electroluminescence element according to the potential of the image data signal applied to the gate. Current is supplied to 10 .

When the scanning signal is transferred to the next scanning line 5 by the sequential scanning of the control section B, the driving of the switching transistor 11 is turned off. However, the switching transistor 11
Since the capacitor 13 holds the potential of the charged image data signal even if the driving of the driving transistor 12 is turned off,
Is kept on, and the organic electroluminescence element 10 continues to emit light until the next scanning signal is applied. When a scanning signal is applied next by sequential scanning, the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic electroluminescence element 10 emits light. That is, light emitted from the organic electroluminescent device 10, the organic electroluminescent device 10 of each of the plurality of pixels, provided with a switching transistor 11 and driving transistor 12 are active elements, the plurality of pixels organic electroluminescent devices 10 Is emitting light. Such a light emitting method is called an active matrix method. Here, the light emission of the organic electroluminescence element 10 may be light emission of a plurality of gradations according to a multivalued image data signal having a plurality of gradation potentials,
A predetermined amount of light emission may be turned on or off by a binary image data signal. The potential of the capacitor 13 may be held continuously until the next scan signal is applied, or may be discharged immediately before the next scan signal is applied. In the present invention, the light emission drive of the organic electroluminescence element is not limited to the above-mentioned active matrix method, and may be a passive matrix light emission drive in which the organic electroluminescence element emits light according to the data signal only when the scanning signal is scanned. As the organic electroluminescence element 10 for a plurality of pixels, the red, green, and blue light emitting organic electroluminescence elements described in Examples 1 to 3 are used, and by arranging them in parallel on the same substrate, full color display can be performed.

FIG. 4 is an explanatory diagram for explaining a display device of the passive matrix system. The three elements shown in FIG. 4 are stacked and integrated. In FIG. 4, a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice pattern so as to face each other with the pixel 3 interposed therebetween. When the scanning signal of the scanning line 5 is applied by the sequential scanning, the applied scanning line 5
The pixel 3 connected to the light source emits light according to the image data signal. In the passive matrix system, the pixel 3 has no active element, and the manufacturing cost can be reduced.

[0061]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. The compounds used in the examples are shown below.

[0062]

[Chemical 25]

[0063]

[Chemical formula 26]

[0064]

[Chemical 27]

[0065]

[Chemical 28]

[0066]

[Chemical 29]

Example 1 After patterning was carried out on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) on which ITO was formed in a thickness of 150 nm on glass as an anode, a transparent support substrate provided with this ITO transparent electrode was used as i-propyl. Ultrasonic cleaning with alcohol, drying with dry nitrogen gas, and UV ozone cleaning for 5 minutes. This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation system, while the molybdenum resistance heating boat was fixed to m-MTD.
Put 200 mg of ATA, put 200 mg of TPD in another resistance heating boat made of molybdenum, put 200 mg of tris (8-hydroxyquinolinato) aluminum (Alq3) in another resistance heating boat made of molybdenum, and further put another resistance made of molybdenum. Comparative compound 1 on heating boat
200 mg was put and attached to a vacuum vapor deposition apparatus. Then, after depressurizing the vacuum chamber to 4 × 10 ⁻⁴ Pa, m-MTDAT was performed.
The heating boat containing A is heated to 220 ° C., vapor-deposited at a film thickness of 25 nm on a transparent support substrate at a vapor deposition rate of 0.1 to 0.3 nm / sec, and further the heating boat containing TPD. Was heated to 220 ° C. and vapor-deposited with a film thickness of 20 nm at a vapor deposition rate of 0.1 to 0.3 nm / sec to provide a hole transport layer composed of two layers. The substrate temperature during vapor deposition was room temperature.

Next, the heating boat containing the comparative compound 1 was energized and heated to 220 ° C., and the vapor deposition rate was 0.1.
A light emitting layer having a thickness of 30 nm was provided at ˜0.3 nm / sec. Further, by energizing the heating boat containing Alq3,
Heating up to 0 ° C, deposition rate 0.1-0.3nm / sec
Then, an electron transport layer having a thickness of 20 nm was provided. Next, the vacuum chamber was opened, a rectangular perforated mask made of stainless steel was placed on the electron transport layer, while 3 g of magnesium was placed in a resistance heating boat made of molybdenum, and silver was deposited in a basket for vapor deposition made of tungsten with a silver content of 0. Put 5g and put the vacuum chamber again at 2 × 10 ^-4 P
After the pressure was reduced to a, a boat containing magnesium was energized to vapor-deposit magnesium at a vapor deposition rate of 1.5 to 2.0 nm / sec, at the same time, a silver basket was heated at a vapor deposition rate of 0.1 nm / sec. A comparative organic EL element OLED1-1 shown in Table 1 was produced by vapor-depositing silver to form a cathode made of the mixture of magnesium and silver. Organic EL device OLE except that the compound 1 shown in Table 1 was used instead of the comparative compound 1 of the organic EL device OLED1-1.
Similarly to D1-1, organic EL element OLED1-2.
7 was produced. These devices were continuously lit by applying a DC voltage of 15 V in a dry nitrogen gas atmosphere at a temperature of 23 ° C., and the luminous brightness at the start of lighting (cd / m ² ), the time when the brightness was halved and the luminous efficiency (ln / W) Was measured. The light emission brightness is represented by a relative value with the light emission brightness of the organic EL element OLED1-1 being 100, and the time for which the brightness is reduced to half is the organic EL element OLE.
The time when the brightness of D1-1 is halved is expressed as a relative value, and the light emission efficiency is expressed as a relative value when the light emission efficiency of the organic EL element OLED1-1 is 100. The results are shown in Table 1.

[0069]

[Table 1] From Table 1, it can be seen that the organic EL device using the compound of the present invention has improved emission luminance at the start of lighting, emission efficiency, and the time for which the luminance is reduced by half. In particular, it can be seen that the time for the luminance to be reduced to half is improved.

Example 2 A light emitting layer was prepared by using the compound I-27 of the present invention and DCM2 10
An organic EL element OLED was manufactured in the same manner as in Example 1 except that a light emitting layer having a thickness of 30 nm was vapor-deposited at a weight ratio of 0: 1.
2-1 was produced. The organic EL device thus obtained has a temperature of 23
When a direct current voltage of 15 V was applied in a dry nitrogen gas atmosphere, red light emission was obtained. Further, organic EL elements OLED2-2 and OLED2-3 were manufactured in the same manner except that DCM2 was replaced with Qd-2 or BCzVBi. The obtained organic EL element OLED2-2 is green or OL
Blue light emission was obtained from ED2-3.

Example 3 As a positive electrode, after patterning was performed on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) on which ITO was formed in a thickness of 150 nm on glass, a transparent support substrate provided with this ITO transparent electrode was i-propyl. Ultrasonic cleaning with alcohol, drying with dry nitrogen gas, and UV ozone cleaning for 5 minutes. This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation system, while the molybdenum resistance heating boat was fixed to m-MTD.
200 mg of ATA was put in another resistance heating boat made of molybdenum, 200 mg of DPVBi was put in another resistance heating boat made of molybdenum, and 200 mg of compound BC was put in the resistance heating boat made of molybdenum, which was attached to a vacuum vapor deposition apparatus. Then, the vacuum chamber is set to 4 × 10 ^-4 P
After the pressure was reduced to a, the heating boat containing m-MTDATA was energized and heated to 220 ° C., and the vapor deposition rate was 0.
25 nm film thickness on transparent support substrate at 1-0.3 nm / sec
Then, the hole transport layer is further energized to the heating boat containing DPVBi, heated to 220 ° C., and vapor-deposited with a film thickness of 20 nm at a vapor deposition rate of 0.1 to 0.3 nm / sec to emit light. Layers were provided. The substrate temperature during vapor deposition was room temperature. Then, the heating boat containing the compound BC is energized and heated to 220 ° C., and the deposition rate is 0.1 to 0.3 n.
An electron transport layer of 30 nm was provided at m / sec.

Next, the vacuum chamber was opened, a rectangular perforated mask made of stainless steel was placed on the electron transport layer, while 3 g of magnesium was placed in a resistance heating boat made of molybdenum,
0.5 g of silver was placed in a tungsten vapor deposition basket, the vacuum chamber was decompressed again to 2 × 10 ⁻⁴ Pa, and a boat containing magnesium was energized to deposit a vapor deposition rate of 1.5 to 2.
Magnesium is vapor-deposited at 0 nm / sec, and at the same time, a silver basket is heated at a vapor deposition rate of 0.1 nm / se.
Comparative organic EL device OLE was prepared by vapor-depositing silver as c and using it as a cathode composed of a mixture of magnesium and silver.
D3-1 was produced. The organic EL element OLED3-1
Of the organic EL device O in the same manner as the organic EL device OLED3-1 except that the compound BC of Example 1 was replaced with the compound shown in Table 2.
LEDs 3-2 to 12 were produced. These elements are heated to 2
Continuous lighting was performed by applying a DC voltage of 15V in a dry nitrogen gas atmosphere three times, and the light emission luminance (cd /
m ² ), the time required for the luminance to halve, and the luminous efficiency (ln / W) were measured. The light emission brightness is represented by a relative value with the light emission brightness of the organic EL element OLED3-1 being 100, and the time for which the brightness is reduced by half is represented with a relative value with the time for which the brightness of the organic EL element OLED3-1 is reduced by half as 100. Is an organic EL element O
It was expressed as a relative value with the luminous efficiency of LED3-1 being 100. The results are shown in Table 2. The emission color was blue.

[0073]

[Table 2] From Table 2, it can be seen that the organic EL device using the compound of the present invention has improved emission luminance at the start of lighting, emission efficiency, and a half-time of luminance. In particular, it can be seen that the time for the luminance to be reduced to half is improved. Further, I-13, I-17, I-19, I-27, I-28, and I-33 used as the electron transporting materials of the organic EL devices OLED3-7 to 12 have a band gap of 3.20 eV to. 3.
It is in the range of 60 eV, and it can be seen that the emission luminance, the emission efficiency, and the time for which the luminance is reduced to half are significantly improved.

Example 4 The cathode of the organic EL element OLED3-8 manufactured in Example 3 was replaced with Al, and lithium fluoride was vapor-deposited to a thickness of 0.5 nm between the electron transport layer and the cathode to form a cathode buffer layer. An organic EL element OLED4-1 was produced in the same manner as the organic EL element OLED3-8 except that the above was provided. Example 3
Similarly, the emission luminance at the start of lighting (cd / m ² ), the emission efficiency (ln / W), and the time at which the luminance is reduced to half were measured, and the emission luminance, emission efficiency, and luminance Relative comparison was performed assuming that the time for halving each was 100. The light emission luminance was 263, the light emitting efficiency was 190, and the time required to reduce the luminance by half was 565. In addition, the organic EL element OLED3
Similarly, when the cathode buffer layer was introduced to -4 to 7 and 3 to 9 to 12, the same effect was obtained.

Example 5 Organic EL device OLEDs 3-4 to 12 produced in Example 3
An organic EL device was manufactured in the same manner except that each of the light emitting layers was replaced with a light emitting layer having Alq ₃ deposited thereon or a light emitting layer having Alq ₃ and DCM 2 deposited at a weight ratio of 100: 1. For each of the obtained organic EL devices, the emission luminance at the start of lighting (cd / m ² ) and the time at which the luminance was reduced to half were measured in the same manner as in Example 3, and the emission luminance at the start of lighting (cd / m ^{2 2} ) and the time required for the brightness to halve was confirmed to be improved. In the case of using the Alq ₃ as a light emitting layer emitting green light is obtained, Alq ₃ and DCM
Red light emission was obtained from the light emitting layer in which 2 was 100: 1.

Example 6 The red, green and blue light emitting organic EL devices produced in Examples 3 and 5, respectively, were placed side by side on the same substrate to produce the active matrix type full color display device shown in FIG. By driving the full-color display device, a clear full-color moving image display with high brightness was obtained.

Example 7 The organic EL element OLED7-1 was manufactured in the same manner except that the hole transport material of the organic EL element OLED4-1 manufactured in Example 4 was changed to m-MTDATXA and the organic compound of the light emitting layer was changed to DMPhen. Was produced. <Preparation of Color Conversion Filter Using Inorganic Phosphor> 15 g of ethanol and 0.2 g of γ-glycidoxypropyltriethoxysilane in 0.16 g of Aerosil having an average particle size of 5 nm
2 g was added and the mixture was stirred in an open system at room temperature for 1 hour. The obtained mixture and 20 g of RL-12 were transferred to a mortar and mixed well, then, in an oven at 70 ° C. for 2 hours, then at 120 ° C.
Was heated in the oven for 2 hours to obtain a surface-modified RL-12. Similarly, the surface modification of GL-10 and BL-3 was performed, and the surface modification GL-10 and BL-3 were obtained. To 10 g of the above surface-modified RL-12, 30 g of butyral (BX-1) dissolved in a mixed solution (300 g) of toluene / ethanol = 1/1 was added, and after stirring, the wet film thickness on the glass was 200 μm. Was applied. The coated glass obtained was heated and dried in an oven at 100 ° C. for 4 hours to prepare a red color conversion filter F-1 having a color conversion layer formed on the glass. In addition, surface modification G
A green conversion filter F-2 coated with L-10 and a blue conversion filter F-3 coated with surface modified BL-3 were produced. Then, on the lower side of the transparent substrate of the organic EL element OLED7-1, a blue conversion filter F- is formed as a color conversion unit.
3 was attached in a stripe shape.

The layer structure of the organic EL element to which the color conversion filter is attached is as follows. Color conversion part / transparent substrate / anode / organic compound thin film / cathode When a voltage of 15 V was applied to the organic EL element OLED 7-1 in which the blue conversion filter F-3 was attached in a stripe shape, a clear blue color of 320 cd / m ² was obtained. Luminescence was obtained. The maximum emission wavelength of the emission spectrum is 448 nm, CI
It was (0.15, 0.06) on the E chromaticity coordinate. Organic EL element OLED7 in which the green conversion filter F-2 is attached in a stripe shape in the same manner except that the blue conversion filter F-3 of the color conversion unit is replaced with the green conversion filter F-2 or the red conversion filter F-1. -1 and red conversion filter F-1 pasted in stripes on organic E
L element OLED7-1 was produced. From the organic EL element OLED 7-1 in which the obtained green color conversion filter F-2 was attached in a stripe shape, 250 cd / m ² , a maximum emission wavelength of 532 nm, and a CIE chromaticity coordinate (0.24, 0.6
The green light 3) is 1 from the organic EL element OLED 7-1 in which the red conversion filter F-1 is attached in a stripe shape.
Red light of 70 cd / m ² , a maximum emission wavelength of 615 nm, and (0.63, 0.33) on the CIE chromaticity coordinates were obtained. The above-mentioned emission luminosity of blue light, green light and red light is superior to that of the organic electroluminescence device described in the examples of Japanese Patent No. 2,795,932. In addition, an organic EL device having the following layer structure was prepared in which the color conversion part was provided on the upper side of the transparent substrate.
The layer structure is as follows. Transparent substrate / color conversion part / anode / organic compound thin film / cathode In the above organic EL element also, the organic EL element OLE in which the blue conversion filter F-3 is attached in a stripe shape
Organic EL element OLED 7-1 in which D7-1 and green conversion filter F-2 are attached in a stripe shape, and organic EL element in which red conversion filter F-1 is attached in a stripe shape
Maximum emission wavelength, CIE that is almost the same as that of the element OLED7-1
An emission spectrum in chromaticity coordinates was obtained.

Example 8 In the display section A having a plurality of pixels 3 shown in FIG. 2, all the plurality of organic electroluminescence elements provided in the plurality of pixels 3 are the organic EL elements OLE described in the example 7.
A display device designated as D7-1 was produced. When a voltage was applied to the display device, blue-violet light emission was obtained from all the pixels 3. Next, an organic EL element having a color conversion layer will be described with reference to the drawings. 5 and 6 are cross-sectional views illustrating the layer structure of the organic EL element having the color conversion layer. In FIG. 5, the organic electroluminescence device 10 is shown.
Is the organic EL unit Y on the upper side of the glass transparent substrate 10d.
However, the color conversion unit X is laminated on the lower side. Further, in FIG. 6, the organic electroluminescence element 10 is
The color conversion unit X and the organic E are provided on the upper side of the glass transparent substrate 10d.
The L portion Y is laminated in this order. In the figure, 10a is A
The cathode made of l, 10b is an organic compound thin film in which a hole transport layer, a light emitting layer, an electron transport layer, and a cathode buffer layer are laminated, 1
0c is an anode (ITO transparent electrode), 10d is a transparent substrate, 1
0e is the red color conversion filter F-1 produced in Example 7,
Green conversion filter F-2 or blue conversion filter F
-3 is a color conversion layer in which stripes are arranged side by side. In the organic EL device having the layer structure shown in FIG. 5, the cathode 1
0a and the transparent electrode 10c through the organic compound thin film 10b
When a current was supplied to the device, it emitted light according to the amount of current. The emitted light passes through the transparent substrate 10d and is absorbed by the color conversion layer 10e, and in the region where the color conversion layer has a red conversion capability (red conversion filter F-1 portion), the color in the red region and the green conversion capability (green conversion) are obtained. The color of the green region is emitted in the region of the filter F-2), and the color of the blue region is emitted in the region of the blue conversion filter F-3 (having the blue conversion capability), which can be extracted in the direction of the white arrow shown in the figure. did it. In the organic EL element having the layer structure shown in FIG. 6, the organic electroluminescent element 10 is a glass transparent substrate 10d.
The color conversion section X and the organic EL section Y are stacked in this order on the upper side of the, but like the organic EL element of FIG. 5, red, green, and blue light is emitted, and the direction of the white arrow shown in the figure. I was able to extract light. By driving the organic EL device having the color conversion layer shown in FIGS. 5 and 6, a clear full-color moving image display with high brightness was obtained.

[0080]

The organic electroluminescence device of the present invention can provide a display device having excellent luminous efficiency, long life, low power consumption and long life.

[Brief description of drawings]

FIG. 1 is a schematic view showing an example of a display device including an organic electroluminescence element.

FIG. 2 is a schematic diagram of a display unit.

FIG. 3 is a schematic diagram of a pixel.

FIG. 4 is an explanatory diagram illustrating a display device of a passive matrix system.

FIG. 5 is a cross-sectional view illustrating a layer structure of an organic electroluminescence element having a color conversion layer.

FIG. 6 is a cross-sectional view illustrating a layer structure of an organic electroluminescence element having a color conversion layer.

[Description of Reference Signs] 1 display 3 pixel 5 scanning line 6 data line 7 power supply line 10 organic electroluminescence element 10a cathode 10b organic compound thin film 10c transparent electrode 10d transparent substrate 10e color conversion layer 11 switching transistor 12 drive transistor 13 capacitor A display section (Display) B Control unit X Color conversion unit Y Organic EL unit

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) H05B 33/22 H05B 33/22 AB (72) Inventor Motoki Kinoshita 1 Sakura Town, Hino City, Tokyo Konica Corporation (72) Inventor Hiroshi Kita 1 Konica Co., Ltd., Sakura-cho, Hino-shi, Tokyo (72) Inventor Yasuhiko Shirota 3-5-7 F-term, Daikoku-cho, Toyonaka-shi, Osaka 3K007 AB02 AB03 AB04 AB11 BA06 CA01 CB01 DA01 DB03 EB00 5C094 AA07 AA08 AA10 AA22 BA03 BA12 BA27 BA32 CA19 CA24 CA25 DA13 EA04 EA05 EB02 ED03 FA01 FB01 FB20

Claims (14)

[Claims] 1. An organic electroluminescence device having an organic layer sandwiched between two electrodes, wherein at least one of the organic layers contains at least one compound represented by the following general formula (1). Characteristic organic electroluminescence device. [Chemical 1] In the formula, B represents a boron atom, C represents a carbon atom, and A
₁₁ , A ₁₂ and A ₁₃ represent a carbon atom or a nitrogen atom,
Z ₁₁ , Z ₁₂ and Z ₁₃ represent an atomic group necessary for completing an aromatic ring, and R ₁₁ , R ₁₂ and R ₁₃ each independently represent an alkyl group, an alkyloxy group, an aryloxy group or a halogen atom. , R ₁₄ , R ₁₅ and R ₁₆ each independently represent a hydrogen atom or a monovalent substituent, and l, m and n each independently represent 0 to 7. 2. In the general formula (1), R ₁₄ , R ₁₅ , R
_16. The organic electroluminescence device according to claim 1, wherein each of ₁₆ is an alkyl group or a halogen atom. 3. The organic electroluminescent element according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2). [Chemical 2] In the formula, B represents a boron atom, C represents a carbon atom, and A
₂₁ , A ₂₂ , A ₂₃ , A ₂₄ , A ₂₅ and A ₂₆ represent a carbon atom or a nitrogen atom, Z ₂₁ , Z ₂₂ and Z ₂₃ represent a group of atoms necessary for completing an aromatic ring, and R ₂₁ , R ₂₂ , R ₂₃ , R
₂₄ , R ₂₅ and R ₂₆ each independently represent an alkyl group, an alkyloxy group, an aryloxy group or a halogen atom, and R ₂₇ , R ₂₈ and R ₂₉ each independently represent a hydrogen atom or a monovalent substituent, l ₂ , m ₂ and n ₂ each independently represent 0 to 7. 4. The odor of general formula (1) or general formula (2)
Z₁₁, Z₁₂, Z ₁₃, Z_{twenty one}, Z_{twenty two}And Z_{twenty three}By
The aromatic ring formed is an aromatic hydrocarbon ring
The organic electro according to any one of claims 1 to 3.
Luminescence element. 5. The compound represented by the general formula (1) is
Characterized by being a compound represented by the general formula (3)
The organic electroluminescence according to claim 1 or 2.
S element. [Chemical 3] In the formula, B represents a boron atom and R₃₁, R₃₅, R₄₁,
R₄₅, R₅₁And R₅₅Is an alkyl group or halogen atom
Represents R₃₂, R₃₃, R₃₄, R₄₂, R₄₃, R₄₄, R ₅₂,
R₅₃And R₅₄Represents a hydrogen atom or a monovalent substituent.
However, R₃₂, R₃₃, R₃₄At least one of R₄₂, R
₄₃, R₄₄At least one of R₅₂, R₅₃And R₅₄Small
At least one kind is an aromatic ring group. 6. The band gap of the compound represented by formula (1), (2) or (3) is 2.96 eV to 3.8.
It is 0 eV, The organic electroluminescent element in any one of Claims 1-5 characterized by the above-mentioned. 7. The band gap of the compound represented by formula (1), (2) or (3) is 3.20 eV to 3.6.
It is 0 eV, The organic electroluminescent element in any one of Claims 1-6 characterized by the above-mentioned. 8. The organic electroluminescence according to claim 1, wherein the compound represented by the general formula (1), (2) or (3) is contained in the light emitting layer. element. 9. The organic electroluminescent device according to claim 1, wherein the compound represented by formula (1), (2) or (3) is contained in the electron transport layer. Luminescence element. 10. The organic electroluminescence device according to claim 1, further comprising a cathode buffer layer between the cathode and the electron transport layer. 11. A display device comprising the organic electroluminescence element according to claim 1. 12. At least one organic electroluminescent element according to any one of claims 1 to 10, wherein two or more organic electroluminescent elements emitting light of different maximum wavelengths are arranged side by side on the same substrate. The display device according to claim 11, wherein: 13. An organic electroluminescence device according to claim 1, and a color conversion layer which absorbs light emitted from the organic electroluminescence device and emits light having a maximum wavelength different from that of the organic electroluminescence device. A display device characterized by. 14. The display device according to claim 13, wherein two or more kinds of color conversion layers which emit light of different maximum wavelengths are arranged side by side on the same substrate.