JP2002280178A - Organic luminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic luminescent element having extremely high efficiency, high luminance, a long-life optical output and extremely high durability, showing various kinds of luminescent hues, easy to manufacture and producible at a relatively low cost. SOLUTION: This organic luminescent element has at least a couple of electrodes comprising a positive electrode and a negative electrode, and one or more layers including organic compounds interposed between the couple of electrodes. In this case, at least one layer out of the layers containing the organic compounds contains a compound expressed by the following general formula [1].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an organic light emitting device, and more particularly, to a device that emits light by applying an electric field to a thin film containing an organic compound.

[0002]

2. Description of the Related Art In an organic light emitting device, a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode, and electrons and holes (holes) are injected from each electrode to exciton the fluorescent compound. It is an element that utilizes light emitted when this exciton is returned to the ground state.

In 1987, a study by Kodak Company (Appl.
Phys. Lett. 51, 913 (1987)), a function-separated type 2 using ITO as an anode, magnesium-silver alloy as a cathode, an aluminum quinolinol complex as an electron transporting material and a luminescent material, and a triphenylamine derivative as a hole transporting material. This device has a layered structure, and has an applied voltage of about 10 V and 1000 cd / m ^2.
A degree of luminescence has been reported. Related patents include U.S. Pat. No. 4,539,507 and U.S. Pat.
0,432, U.S. Pat. No. 4,885,211 and the like.

[0004] In addition, by changing the type of the fluorescent organic compound, light emission from ultraviolet to infrared can be achieved, and various compounds have recently been actively studied. For example, US Pat. No. 5,151,629 and US Pat.
409,783, U.S. Patent No. 5,382,477,
JP-A-2-247278, JP-A-3-25519
0, JP-A-5-202356, JP-A-9-206
JP-A-202878 and JP-A-9-227576.

[0005] In addition to the organic light-emitting device using the above low-molecular material, an organic light-emitting device using a conjugated polymer is also a group of Cambridge University (Nature,
347, 539 (1990)).
In this report, light emission was confirmed in a single layer by forming a film of polyphenylenevinylene (PPV) in a coating system.
Patents related to organic light-emitting devices using conjugated polymers include US Pat. No. 5,247,190 and US Pat.
No. 514,878, US Pat. No. 5,672,678,
JP-A-4-145192, JP-A-5-24746
No. 0 publication.

As described above, recent advances in organic light-emitting devices have been remarkable, and their characteristics are that high luminance, a variety of emission wavelengths, high-speed response, a thin and lightweight light-emitting device can be realized at a low applied voltage. It suggests potential for a wide range of applications.

However, at present, light output with higher luminance or higher conversion efficiency is required. In addition, there are still many problems in terms of durability such as a change with time due to long-term use and deterioration due to an atmospheric gas containing oxygen or moisture. Further, when application to a full-color display or the like is considered, light emission of blue, green, and red with good color purity is required, but this problem has not yet been sufficiently solved.

[0008]

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems of the prior art, and an organic light-emitting device having extremely high efficiency, high brightness, and long life light output has been developed. To provide. Another object of the present invention is to provide an organic light-emitting device that has various emission wavelengths, exhibits various emission hues, and is extremely durable. Another object of the present invention is to provide an organic light emitting device that can be easily manufactured and can be manufactured at relatively low cost.

[0009]

The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that a pair of electrodes including an anode and a cathode and one or more electrodes sandwiched between the pair of electrodes are provided. In an organic light-emitting device having at least a layer containing an organic compound, at least one of the layers containing the organic compound contains a specific compound, thereby producing an organic light-emitting device having a higher efficiency and a higher luminance light output. It has been found that the present invention can be performed, and the present invention has been completed.

That is, the organic light emitting device of the present invention is an organic light emitting device having at least a pair of electrodes comprising an anode and a cathode, and at least a layer containing one or more organic compounds sandwiched between the pair of electrodes. At least one of the layers containing an organic compound contains a compound represented by the following general formula [1].

[0011]

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(In the formula [1], R _{1 to} R ₁₂ are hydrogen, substituted or unsubstituted alkyl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkoxy group, A substituted or unsubstituted aryl group,
It represents any of a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted amino group, a halogen, and a substituted or unsubstituted azo group. Where R ₁
To R ₁₂ may be the same or different. Also, R
_In each of the substituents _{1 to} R ₆ and R _{7 to} R ₁₂ , two or more adjacent substituents may form a condensed ring. Two or more of these fused rings may be formed simultaneously. The fused ring may be formed by a hetero ring.

-Cm- and -Cn- are carbon chains having 1 to 11 carbon atoms, and m and n represent the number of carbon atoms. When m and n = 1,
This carbon and the nitrogen atom specified in the formula have a single bond. When m and n ≧ 2, the carbon chain may contain an unsaturated bond, including the bond to the nitrogen atom specified in the formula. When m and n ≧ 3, the carbon chain may contain a nitrogen atom.

Ri and Rj are substituents in -Cm- and -Cn-, and are hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted. An alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted amino group, a halogen, a substituted or unsubstituted azo group Show. Although the numbers of Ri and Rj also vary depending on the number of m and n and the bonding state of the carbon atom and the nitrogen atom, these Ri and Rj may be the same or different. Two or more adjacent substituents may form a condensed ring. Two or more of these fused rings may be formed simultaneously. The fused ring may be formed by a hetero ring.

M is a monovalent to pentavalent metal and includes all transition elements in the periodic table. A is the number of metal atoms, be is the number of hydrogen atoms, a is 0 to 2, and be is 0 or 1.

The numbers b to e represent the bonding state with nitrogen, the valence of M, the number of M, and the number of carbon atoms at the end of the carbon atoms of Cm and Cn bonded to nitrogen, which are specified in the formula. , Cn and the bonding state thereof. )

[0017]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.

First, the compound represented by the above general formula [1] used in the present invention will be described.

Specific examples of the substituents R _{1 to} R ₁₂ in the general formula [1] are shown below.

Examples of the substituted or unsubstituted alkyl group and aralkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a ter-butyl group, an octyl group, a benzyl group and a phenethyl group.

Examples of the substituted or unsubstituted alkenyl group include a vinyl group, an allyl group (2-propenyl group), a 1-propenyl group, an iso-propenyl group and a 2-butenyl group.

Examples of the substituted or unsubstituted alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a phenoxy group, a 4-butylphenoxy group and a benzyloxy group.

Examples of the substituted or unsubstituted aryl groups include phenyl, 4-methylphenyl, 4-ethylphenyl, 3-chlorophenyl, 3,5-dimethylphenyl, triphenylamino, biphenyl, Examples include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a tolyl group, a tosyl group, and a halogen-substituted naphthyl group.

As the substituted or unsubstituted heterocyclic group,
Thienyl group, furyl group, pyrrolyl group, imidazolyl group,
5-membered heterocycle such as pyrazolyl group, isothiazolyl group, isoxazolyl group, 6-membered heterocycle such as pyranyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, bipyridyl group, methylpyridyl group, terthienyl group, propylthienyl Group, isobenzofuranyl group, indolizinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, indolinyl group, isoindolinyl group, chromenyl group, quinolizinyl group, isoquinolyl group, quinolyl group, phthalazinyl group, naphthyridinyl group, quinazolinyl group, A carbazolyl group, an N-ethylcarbazolyl group, a thianthrenyl group, a phenanthridinyl group, a perimidinyl group and the like.

Examples of the substituted or unsubstituted carbonyl group include an acetyl group, a propionyl group, an isobutyryl group, a methacryloyl group, a benzoyl group, a naphthoyl group, an anthroyl group and a toluoyl group.

Examples of the substituted or unsubstituted amino group include methylamino, ethylamino, dimethylamino, diethylamino, methylethylamino, benzylamino, methylbenzylamino, anilino, diphenylamino, phenyl Examples thereof include a tolylamino group and a ditolylamino group.

As the halogen, fluorine, chlorine, bromine,
Iodine.

As the substituted or unsubstituted azo group, in addition to an unsubstituted azo group, an azo group substituted with the above substituents can be used.

As the condensed ring, benzo, naphtho, anthra, acenaphtho and the like can be used, and hetero rings such as furo, imidazo, pyrido, quino and thieno can also be contained.

The substituents which R _{1 to} R ₁₂ may have include the above-mentioned alkyl group, aralkyl group, alkenyl group, alkoxy group, aryl group, heterocyclic group, carbonyl group, amino group and the like. Groups, halogens, azo groups, condensed rings, and the like, but are not limited thereto.

Next, the compounds represented by the general formula [1] include the general formulas specifically showing -Cm- and -Cn- (compounds (1) to (16)). However, it is not limited to these compounds. Compounds (1) to (1)
A and a 'in 6) represent 0 or 1.

Compound (1) is an example when m = n = 1, compounds (2) and (3) are examples when m = n = 2, and compound (4) is an example when m = n = 3. Examples, compounds (5) and (6)
Is an example when m = n = 4, compound (7) is an example when m = n = 5, compounds (8) and (9) are examples when m = n = 6, and compound (10) is Example where m = n = 7, compound (11), example where m = 4, n = 3, compound (12)
Is an example when m = 4 and n = 5. Compound (1)
3) to (16) are the cases where nitrogen atoms are included in -Cm- and -Cn-.

[0033]

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[0034]

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[0035]

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[0036]

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Specific examples of Ri and Rj (R _{13 to} R _{32 in the} compounds (1) to (16)) can be the same as those described above for R _{1 to} R ₁₂ .

Next, examples of substituent introduction in the case where m = n = 3 (compound (4)) for the compound represented by the general formula [1] are shown in the case where a = 0 (compounds (17) to (40)). ). Substituents can be introduced in the same manner when coordinating to other m, n, and various metals. However, it is not limited to these compounds.

[0039]

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[0040]

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[0041]

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M is a monovalent to pentavalent metal or the like;
(II), Pt (II), Zn (II), Mg (I
I), Sn (IV), Pb (II), Al, Cd, Si
(IV), Ge (IV), Ba, Sr, Be, Sc (I
II), Ti (IV), Zr (IV), Hf (IV),
Nb (V), Ta (V), Co (III), Rh (II
I), Ir, Ni (II), Sn (II), Ru (II)
I), Cu (II), Ag, Co (II), Ca, H
g, Mn (II), Fe (II), Fe (III) and the like. Other than this, without being limited to these,
Common metals can be used. Also, Ru (I
I) CO, VO, Ru (II) L ₂ , Nb (V) O, T
a (V) O or the like can also be used.

A is arbitrary, but be is in the form of a compound represented by the general formula [1], that is, carbon at the end of —Cm— or —Cn— The valence of the compound skeleton represented by the general formula [1] is determined by the atomic bonding state, the presence and the bonding state of the nitrogen atom in -Cm- and -Cn-, the valence of M, and a. You.

The ionic valence of the compound skeleton represented by the general formula [1] is, for example, when b = d = 0 in the compound (4),
It becomes minus divalent, that is, it becomes a divalent anion ligand, and coordinates well with, for example, a divalent metal ion (a =
1). When M is a non-divalent cation, it can be combined with another ligand or counter ion.
When b = d = 1, a = 0 and it does not become a ligand.

The compound (2) can be a neutral ligand with a valence of 0, and when coordinated with a metal, can have a counter ion of the same valence as the metal. .

When be to e = 0 in the compound (3),
The compound becomes a tetravalent anionic ligand and coordinates well with metal ions. When M is a non-tetravalent cation, it can be combined with another ligand or counter ion.

When b = 0 in the compound (11), the compound becomes a monovalent anion ligand.

Compounds (13) and (14) are -Cm-,-
When there is a nitrogen atom in Cn-, compound (13) has 2
It becomes a valent anionic ligand. The compound (14) can take any of the forms of 0, 1, and 2 metals, and becomes a divalent anion ligand when b = d = 0.

The compounds represented by the general formula [1] can be an anion, but As other anionic ligand or counter ion, for example F ^-, Cl ^-, Br
_{^{-, I -, O 2 -}} , (O 2) 2-, (O 2) -, (OH) -, (S
_{^{H) -, (SO 4)}} 2-, S 2-, N 3-, (CN) -, (NC
O) ^- , (NCS) ^- , (NO ₂ ) ^- , (OAc) ^- , (C
_{^{lO 4) -, (SbO 4}} ) -, (acac) -, OEt -,
^{(Im) -, OMe -,} OR -, OPh -, R - , and the like. In addition, general ligands and counter ions can be used without being limited to these.

Examples of the cationic ligand or counter ion include K ⁺ , Na ⁺ , NH ₄ ⁺ , Li ⁺ ,
Al ³⁺ , Cr ^{3+ and the} like. In addition, general ligands and counter ions can be used without being limited to these.

Further, as the neutral ligand, for example, N
H ₃ , H ₂ O, pyridine, EtOH, imidazole and the like can be mentioned. In addition, general ligands can be used without being limited to these.

When a = 0, the compound represented by the general formula [1] does not become a metal ligand, but can be used as it is.

When a = 1 and 2, each of these compounds can be combined with the above M, various ligands, and various counter ions. Table 1 shows an example of a combination of M, a ligand and a counter ion when the ionic valence of the compound skeleton represented by the general formula [1] is divalent. These are {the ionic valence of the compound skeleton represented by the general formula [1]} + {the total number of ionization numbers of M} + {the total number of ionization numbers of other ligands} + {the total number of ionization numbers of counter ions. The combination may be performed so that｝ = 0, and when the ionic valence of the compound skeleton represented by the general formula [1] is other than 2, the combination may be similarly performed. Also, the combinations are not limited to Table 1.

[0054]

[Table 1]

Next, the organic light emitting device of the present invention will be described with reference to the drawings.

FIG. 1 is a sectional view showing an example of the organic light emitting device of the present invention. FIG. 1 shows a structure in which an anode 2, a light emitting layer 3 and a cathode 4 are sequentially provided on a substrate 1. The light-emitting element used here is useful when it has a single hole-transporting ability, electron-transporting ability, and light-emitting performance, or when a mixture of compounds having the respective properties is used.

FIG. 2 is a sectional view showing another example of the organic light emitting device of the present invention. FIG. 2 shows a configuration in which an anode 2, a hole transport layer 5, an electron transport layer 6, and a cathode 4 are sequentially provided on a substrate 1. In this case, as the luminescent material, a material having one or both functions of a hole transporting property and an electron transporting property is used for each layer, and used in combination with a mere hole transporting substance having no light emitting property or an electron transporting substance. Useful in cases. Further, in this case, the light emitting layer is composed of either the hole transport layer 5 or the electron transport layer 6.

FIG. 3 is a sectional view showing another example of the organic light emitting device of the present invention. FIG. 3 shows a structure in which an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, and a cathode 4 are sequentially provided on a substrate 1. It separates the functions of carrier transport and light emission, and is used in a timely combination with a compound having hole transport, electron transport, and light emitting properties. Can be used, so that the emission hue can be diversified. Further, it is possible to effectively confine each carrier or exciton in the central light emitting layer 3 to improve the luminous efficiency.

However, FIGS. 1 to 3 show only very basic device configurations, and the configuration of the organic light-emitting device using the compound of the present invention is not limited to these. For example, various layer configurations such as providing an insulating layer at the interface between the electrode and the organic layer, providing an adhesive layer or an interference layer, and forming the hole transport layer from two layers having different ionization potentials can be employed.

The compound represented by the general formula [1] used in the present invention is a compound excellent in electron injecting property, electron transporting property and light emitting property as compared with the conventional compound.
3 can be used.

In particular, an organic layer using the compound represented by the general formula [1] of the present invention is useful as an electron transport layer,
It is also useful as a light emitting layer.

In the organic light emitting device of the present invention, the compound represented by the general formula [1] is formed between the anode 2 and the cathode 4 by a vacuum deposition method or a solution coating method. The thickness of the organic layer is thinner than 10 μm, preferably 0.5 μm or less, more preferably 0.01 to 0.5 μm.

In the present invention, the compound represented by the above general formula [1] is used as a component for the electron transporting and light emitting layer. A compound, a light-emitting layer matrix compound, an electron-transporting compound, a charge-transporting polymer material, and a light-emitting polymer material (for example, compounds shown below) can be used together as necessary. However, it is needless to say that the present invention is not limited to these. Hole transport compound

[0064]

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Electron transporting luminescent material

[0066]

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Light emitting material

[0068]

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Emitting layer matrix material and electron transporting material

[0070]

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Polymer-based hole transporting material

[0072]

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Polymer-based light emitting material and charge transporting material

[0074]

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In the organic light emitting device of the present invention, the layer containing the compound represented by the general formula [1] and the layer containing another organic compound are generally formed by a vacuum deposition method or a coating method by dissolving in a suitable solvent. To form a thin film. In particular, when forming a film by a coating method, the film can be formed in combination with an appropriate binder resin.

The binder resin can be selected from a wide range of binder resins, for example, polyvinyl carbazole resin,
Polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, acrylic resin, methacrylic resin, butyral resin, polyvinyl acetal resin,
Examples include, but are not limited to, diallyl phthalate resin, phenol resin, epoxy resin, silicone resin, polysulfone resin, urea resin, and the like. These may be used alone or as a copolymer, alone or as a mixture of two or more.

The anode material preferably has a work function as large as possible. For example, simple metals such as gold, platinum, nickel, palladium, cobalt, selenium, and vanadium or alloys thereof, tin oxide, zinc oxide, indium tin oxide ( Metal oxides such as ITO) and indium zinc oxide can be used. Further, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. These electrode substances may be used alone or in combination of two or more.

On the other hand, the cathode material preferably has a small work function, such as lithium, sodium, potassium, calcium, magnesium, aluminum, indium, silver, and the like.
It can be used as a single metal or a plurality of alloys such as lead, tin and chromium. It is also possible to use metal oxidation such as indium tin oxide (ITO). Further, the cathode may have a single-layer structure or a multilayer structure.

The substrate used in the present invention is not particularly limited, but an opaque substrate such as a metal substrate or a ceramic substrate, or a transparent substrate such as glass, quartz, or a plastic sheet is used. Further, it is also possible to control the emitted light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film or the like on the substrate.

Incidentally, a protective layer or a sealing layer may be provided on the produced device for the purpose of preventing contact with oxygen, moisture, or the like. Examples of the protective layer include an inorganic material film such as a diamond thin film, a metal oxide, and a metal nitride; a polymer film such as a fluorine resin, polyparaxylene, polyethylene, a silicone resin, and a polystyrene resin; and a photocurable resin. Can be Alternatively, the device itself can be covered with glass, a gas impermeable film, metal, or the like, and the element itself can be packaged with an appropriate sealing resin.

[0081]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

Example 1 An element having the structure shown in FIG. 1 was prepared.

On a glass substrate as a substrate 1, indium tin oxide (ITO) as an anode 2 was
A film having a thickness of 0 nm was used as a transparent conductive support substrate. This was ultrasonically washed sequentially with acetone and isopropyl alcohol (IPA), boiled and washed with IPA, and dried. Further, the substrate subjected to UV / ozone cleaning was used as a transparent conductive support substrate.

The compound (4) in which a polyaza macrocyclic compound and OPh are coordinated to Al (III) shown below
1) 0.050 g and polyvinyl carbazole 1.0
0 g was dissolved in 75 ml of tetrahydrofuran to prepare a solution. Using this solution, an organic layer film (light-emitting layer 3) having a thickness of 120 nm was formed on a transparent support substrate by a spin coating method (2000 rpm).

[0085]

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Next, a metal layer film (cathode 4) having a thickness of 150 nm was formed on the above-mentioned organic layer by a vacuum deposition method using a deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%). . The degree of vacuum during vapor deposition is 1.0 × 1
The film was formed under the conditions of 0 ^-4 Pa and a film formation speed of 1.0 to 1.2 nm / sec.

When a DC voltage of 8 V is applied to the device thus obtained with an ITO electrode serving as a positive electrode and an Al—Li electrode serving as a negative electrode, a current flows at a current density of 2.4 mA / cm ² , and an initial luminance is obtained. 160 cd / m ² yellow emission was observed.

Example 2 An element having the structure shown in FIG. 2 was prepared.

On the same transparent conductive support substrate as in Example 1, α-NPD shown in Chemical Formula 10 was applied to a thickness of 70 nm by vacuum evaporation.
The hole transport layer 5 was formed. further,
The following polyaza macrocyclic compounds (42)
Was formed into a film having a thickness of 50 nm by a vacuum evaporation method to form an electron transport layer 6. The degree of vacuum during deposition is 1.0 × 10 ^-4 P
a, The film was formed under the conditions of a film forming speed of 0.2 to 0.3 nm / sec.

[0090]

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Next, an Al-Li electrode was formed in the same manner as in Example 1.

When a DC voltage of 8 V is applied to the device thus obtained with an ITO electrode serving as a positive electrode and an Al-Li electrode serving as a negative electrode, a current flows at a current density of 5.1 mA / cm ² , and an initial luminance is obtained. Orange emission of 320 cd / m ² was observed.

Example 3 An element having the structure shown in FIG. 3 was prepared.

On the same transparent conductive support substrate as in Example 1, a hole transport layer 5 was formed by depositing TPD shown in Chemical Formula 10 to a thickness of 70 nm by a vacuum evaporation method. The light emitting layer 3 was formed to a thickness of 25 nm by a vacuum evaporation method using aluminum trisquinolinol. Furthermore, C shown below
o (III) with polyaza macrocyclic compound and C
The compound (43) to which N was coordinated was converted to 40 by vacuum evaporation.
The electron transport layer 6 was formed to a thickness of nm. The degree of vacuum at the time of vapor deposition was 1.0 × 10 ⁻⁴ Pa, and the film formation rate was 0.2 to 0.
The film was formed under the condition of 3 nm / sec.

[0095]

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Next, an Al—Li electrode was formed in the same manner as in Example 1.

When a DC voltage of 8 V was applied to the device thus obtained with an ITO electrode serving as a positive electrode and an Al-Li electrode serving as a negative electrode, a current flowed at a current density of 5.4 mA / cm ² , resulting in an initial luminance. Green light emission of 560 cd / m ² was observed.

Further, this device was placed under a nitrogen atmosphere.
When the voltage was applied for 1000 hours while maintaining the current density at 5.0 mA / cm ² , the initial luminance was 520 cd / m ² to 10
After 00 hours, the luminance was 470 cd / m ² and the luminance deterioration was very small.

Comparative Example 1 A device of Comparative Example 1 was prepared in exactly the same manner as the device of Example 3 except that the compound used for the electron transport layer 6 of Example 3 was changed to a compound having the following structural formula. .

[0100]

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When a DC voltage of 8 V is applied to the device thus obtained with an ITO electrode serving as a positive electrode and an Al-Li electrode serving as a negative electrode, a current flows at a current density of 3.7 mA / cm ² , and an initial luminance is obtained. Green emission of 55 cd / m ² was observed.

Further, this device was placed under a nitrogen atmosphere.
When a voltage was applied for 1000 hours while maintaining the current density at 5.0 mA / cm ² , the initial luminance was 60 cd / m ² to 100.
No light emission was observed after 0 hour.

[0103]

According to the organic light-emitting device using the polyaza macrocyclic compound of the present invention, high-intensity light emission can be obtained at a low applied voltage, as shown in Examples and Comparative Examples.
Also has excellent durability.

In particular, an organic layer using the polyaza macrocyclic compound of the present invention is useful as an electron transporting layer, and is also useful, for example, as a light emitting layer that emits yellow light.

Further, the device can be prepared by using a vacuum evaporation method or a casting method, and a relatively inexpensive device having a large area can be easily prepared.

[Brief description of the drawings]

FIG. 1 is a cross-sectional view illustrating an example of an organic light emitting device according to the present invention.

FIG. 2 is a cross-sectional view illustrating another example of the organic light emitting device according to the present invention.

FIG. 3 is a cross-sectional view illustrating another example of the organic light emitting device according to the present invention.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Substrate 2 Anode 3 Light emitting layer 4 Cathode 5 Hole transport layer 6 Electron transport layer

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Hiroshi Tanabe 3-30-2 Shimomaruko, Ota-ku, Tokyo Inside Canon Inc. (72) Inventor Kazunori Ueno 3-30-2 Shimomaruko, Ota-ku, Tokyo Canon F term (for reference) 3K007 AB02 AB03 AB04 AB06 AB11 AB18 CA01 CB01 DA01 DB03 EB00

Claims (1)

[Claims] A pair of electrodes comprising an anode and a cathode;
In an organic light-emitting element having at least a layer containing one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers containing the organic compound contains a compound represented by the following general formula [1]. An organic light-emitting device, comprising: Embedded image (In the formula [1], R _{1 to} R ₁₂ represent hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxy group, It represents any of a substituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted amino group, a halogen, and a substituted or unsubstituted azo group, provided that R ₁ to R ₁₂ may be the same or different, and R _{1 to} R ₆ , R ₇
In each of the substituents of R ₁₂ to R ₁₂ , two or more adjacent substituents may form a condensed ring. Two or more of these fused rings may be formed simultaneously. The fused ring may be formed by a hetero ring. -Cm- and -Cn- have 1 to 1 carbon atoms.
In one carbon chain, m and n represent the number of carbons. When m and n = 1, this carbon and the nitrogen atom specified in the formula have a single bond. When m and n ≧ 2, the carbon chain may contain an unsaturated bond, including the bond to the nitrogen atom specified in the formula. When m and n ≧ 3, the carbon chain may contain a nitrogen atom. Ri and Rj are substituents in -Cm- and -Cn-, and are hydrogen, substituted or unsubstituted alkyl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkoxy group. A substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted amino group, a halogen, or a substituted or unsubstituted azo group. The numbers of Ri and Rj also vary depending on the number of m and n and the bonding state of the carbon atom and the nitrogen atom.
Rj may be the same or different. Two adjacent
One or more substituents may form a condensed ring. Two or more of these fused rings may be formed simultaneously. The fused ring may be formed by a hetero ring. M is a monovalent to pentavalent metal and includes all transition elements in the periodic table. A is the number of metal atoms, be is the number of hydrogen atoms, a is 0 to 2, and be is 0 or 1. The number of be is C
Of the carbon atoms of m and Cn, the state of the carbon atom at the end bonded to nitrogen specified in the formula, the bonding state with nitrogen, the valence of M, M
, The presence of nitrogen atoms in Cm and Cn, and their bonding state. )