JP2013043858A - Novel condensed polycyclic compound and organic light emitting element having the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel condensed polycyclic compound having red light emission of good color purity and to provide an organic light emitting element of red light emission having high light emitting efficiency and low driving voltage.SOLUTION: The condensed polycyclic compound represented by general formula [1] is provided. (in formula, R1 to R4 are each independently selected from a hydrogen atom or a 1-4C alkyl group, Ar1 and Ar2 are each independently selected from aryl groups, the aryl group are any one of a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group and a naphthyl group, and the aryl group may have a 1-4C alkyl group).

Description

  The present invention relates to a novel polycyclic compound and an organic light emitting device having the same.

  An organic light emitting element is an element having a pair of electrodes and an organic compound layer disposed between them. By injecting electrons and holes from the pair of electrodes, excitons of the luminescent organic compound in the organic compound layer are generated, and light is emitted when the excitons return to the ground state.

  Patent Document 1 describes a derivative a-1 of the following compound as a compound that emits green light.

a-1

JP 2003-347057 A

  Patent Document 1 describes a compound that emits green light. In order to obtain a compound that emits red light, it is known to increase the emission wavelength of the compound by providing a substituent. However, when a substituent is provided, the stability of the compound may be impaired.

  An object of the present invention is to provide a novel condensed ring compound having a red luminescence with a good color purity and only a basic skeleton. Another object of the present invention is to provide an organic light-emitting device having the light emission efficiency and a low driving voltage having the novel condensed compound.

  Therefore, the present invention provides a condensed polycyclic compound represented by the following general formula [1].

[1]

In the general formula [1], R _{1 to} R ₄ are each independently selected from a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Ar ₁ and Ar ₂ are each independently selected from aryl groups.

  The aryl group is any one of a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a naphthyl group.

  The aryl group may have an alkyl group having 1 to 4 carbon atoms.

  According to the present invention, a novel fused ring compound that emits red light with good color purity can be provided. Moreover, the red organic light emitting element which has it and has high luminous efficiency and low driving voltage can be provided.

It is a schematic diagram of an example of the organic light emitting element of the light emitting layer laminated | stacked type which concerns on this embodiment. It is a cross-sectional schematic diagram which shows the organic light emitting element which concerns on this embodiment, and the switching element connected to an organic light emitting element.

  The present invention is a condensed polycyclic compound represented by the following general formula [1].

[1]

In the general formula [1], R _{1 to} R ₄ are each independently selected from a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Ar ₁ and Ar ₂ are each independently selected from aryl groups.

  The aryl group is any one of a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a naphthyl group.

  The aryl group may have an alkyl group having 1 to 4 carbon atoms.

  More specifically, an alkyl group having 1 to 4 carbon atoms is a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, or a tert-butyl group. It is a butyl group.

  The novel condensed polycyclic compound according to the present invention is a skeleton partially having the following skeleton a-1.

a-1

a-1 is a compound which emits light in the green region, as disclosed in Patent Document 1. On the other hand, the condensed polycyclic compound according to the present invention is a compound that emits light in the red region, and is greatly different in light emission characteristics from a-1.

  The compound emitting light in the red region means that the first emission peak is in the region from 580 nm to 650 nm when the emission spectrum is measured with a dilute solution.

  The compound emitting in the green region means that the first emission peak is in the region from 490 nm to 560 nm when the emission spectrum is measured with a dilute solution.

  Moreover, the novel condensed polycyclic compound according to the present invention is a compound containing a carbonyl group in the basic skeleton.

  Due to the electron-withdrawing effect of the carbonyl group, the basic skeleton of the condensed polycyclic compound according to the present invention has a high ionization potential, and thus is a stable skeleton that is not easily oxidized by oxygen or the like.

  The basic skeleton a-2 of the condensed polycyclic compound according to the present invention shown below has high planarity and tends to cause concentration quenching due to molecular association.

a-2

  Therefore, by providing an aryl group at Ar1 and Ar2 in the general formula [1], the planarity of the entire molecule is lost, so that concentration quenching can be suppressed. The aryl groups of Ar1 and Ar2 may be the same or different.

  The aryl group is preferably any one of a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a naphthyl group.

  This effect is the same even if it has any substituent of a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a naphthyl group.

  Moreover, the effect which suppresses concentration quenching becomes large because these aryl groups have a C1-C4 alkyl group.

  The alkyl group provided in the aryl group may be provided in any position.

Furthermore, in general formula [1], by providing an alkyl group having 1 to 4 carbon atoms in R _{1 to} R ₄ , there is an effect of further suppressing concentration quenching.

In this case, even if an alkyl group having 1 to ₄ carbon atoms is substituted for R _{1 to} R ₄ , the emission wavelength of light emitted from the compound does not change significantly.

  Specific examples of the condensed polycyclic compound according to the present invention are shown below. However, the present invention is not limited to these.

(Properties of exemplary compounds)
The condensed polycyclic compounds exemplified in Group A are compounds in which Ar1 and Ar2 in General Formula [1] are phenyl groups. Since these compounds have a low molecular weight, they can be deposited at a low temperature when the compounds are deposited.

  A compound having a phenyl group having an alkyl group is preferable because it has a large effect of suppressing concentration quenching.

  The condensed polycyclic compound exemplified in Group B is a compound group in which Ar1 and Ar2 in General Formula [1] are a biphenyl group or a terphenyl group.

  Since the condensed polycyclic compound shown in Group B has a rigid condensed polycyclic group, in the film state, the amorphous property is maintained and the mobility of electrons and holes is high.

  The condensed polycyclic compounds exemplified in Group C are a group of compounds in which Ar1 and Ar2 in General Formula [1] are a fluorenyl group or a naphthyl group. Since the condensed polycyclic compound shown in Group C has a rigid fluorenyl group or naphthyl group, it maintains amorphousness in the film state and has high electron and hole mobility.

  The condensed polycyclic compounds exemplified in Group D are a group of compounds in which Ar1 and Ar2 in General Formula [1] are different aryl groups. These condensed polycyclic compounds are difficult to crystallize because of their asymmetric molecular structures. Therefore, a stable amorphous film can be formed.

(Description of synthesis route)
An example of a synthetic route for the condensed polycyclic compound according to the present invention will be described. The reaction formula is shown below.

  The exemplary compound according to the present embodiment can be synthesized by forming an arbitrary Ar-substituted anthracene pinacol borane d-3 in dibromodiiodobenzene through a Suzuki-Miyaura coupling and Heck reaction to form a 5-membered ring.

(Description of organic light emitting device)
Next, the organic light emitting device according to this embodiment will be described.

  The organic light-emitting device according to this embodiment has a pair of electrodes, an anode and a cathode, and an organic compound layer disposed therebetween, and the organic compound layer has an organic compound represented by the general formula [1]. It is an element.

  The organic compound layer included in the organic light emitting device according to this embodiment may be a single layer or a plurality of layers. The multiple layer is a layer appropriately selected from a hole injection layer, a hole transport layer, a light emitting layer, a hole block layer, an electron transport layer, an electron injection layer, an exciton block layer, and the like. Of course, it is possible to select a plurality from the group and use them in combination.

  Furthermore, the light emitting layer may be a single layer or a stacked layer. For example, in the case of a white light-emitting element, the organic light-emitting element includes a plurality of light-emitting layers, and each of the light-emitting layers emits a different color, so that an element that emits white can be used.

  Since one of the plurality of light emitting layers of the organic light emitting element emitting white according to the present embodiment has the condensed polycyclic compound represented by the general formula [1], it is a light emitting layer emitting red.

  Since the light emitting layers other than the light emitting layer emitting red color among the plurality of light emitting layers emit a color different from red, the whole element emits white color. That is, it is an element that emits white by mixing colors of red and other colors.

  In addition, the light emitting layer is a single layer, and can emit white light by including a plurality of light emitting materials.

Although the structure of the light emitting layer as shown below is mentioned in the form of the organic light emitting element emitting white according to the present embodiment, it is of course not limited thereto.
(1) Single layer: element including blue, green and red light emitting materials (2) Lamination: element including light blue and yellow light emitting materials (3) Two layers: light emission including blue light emitting layer and green and red light emitting materials Layer or laminated element of red light emitting layer and light emitting layer containing blue and green light emitting materials (4) 2 layers: laminated element of light emitting layer and yellow light emitting layer (5) 3 layers: blue light emitting layer and green light emitting Layered Element of Layer and Red Light-Emitting Layer FIG. 1 is a schematic cross-sectional view showing an example of an element configuration having the light-emitting layer (5) as an example of the white organic light-emitting element according to the present embodiment. In this figure, an organic light emitting device having three color light emitting layers is shown. Details of the structure will be described below.

  This organic light-emitting device has an anode 1, a hole injection layer 2, a hole transport layer 3, a blue light-emitting layer 4, a green light-emitting layer 5, a red light-emitting layer 6, an electron transport layer 7, and an electron injection on a substrate such as glass. This is an element configuration in which a layer 8 and a cathode 9 are laminated. However, the lamination of the blue, green, and red light emitting layers may be in any order.

In the organic light-emitting device that emits white according to the present embodiment, the organic compound layer includes a plurality of light-emitting layers, and at least one of the plurality of light-emitting layers includes the condensed polycyclic compound and emits red light. Yes,
It is an organic light emitting device that emits white from a mixed color of a light emitting layer other than a light emitting layer emitting red and a red color.

  Further, the light emitting layer is not limited to the stacked form, and may be arranged side by side. The term “side by side” means that the light emitting layers arranged side by side are arranged so as to be in contact with the hole transport layer and the electron transport layer.

  The light emitting layer may have a form in which a domain of a light emitting layer emitting another color is formed in a light emitting layer emitting one color.

  It can also be said that the light emitting portion has a plurality of light emitting layers.

  When obtaining an organic light-emitting element that emits white, the blue light-emitting material is not particularly limited, but a light-emitting material having a fluoranthene skeleton or an anthracene skeleton is preferable.

  The green light emitting material is not particularly limited, but a light emitting material having a fluoranthene skeleton or an anthracene skeleton is preferable.

  The condensed polycyclic compound represented by the general formula [1] of the present invention can be used as the host material or guest material of the light emitting layer. In particular, when used as a guest material, a highly efficient light-emitting element that emits light in a red region having an emission peak in a region from 580 nm to 660 nm is provided.

  The light emitting material for the blue light emitting layer and the light emitting material for the green light emitting layer are not particularly limited, but it is preferable to use a compound having a fluoranthene skeleton or an anthracene skeleton.

  Here, the host material is a compound having the largest weight ratio in the light emitting layer. The guest compound is a compound having a weight ratio smaller than that of the host material in the light emitting layer, and is a compound that mainly emits light. The assist material is a compound having a weight ratio smaller than that of the host material in the light emitting layer, and is a compound that helps the light emission of the guest material.

  When the condensed polycyclic compound according to this embodiment is used as a guest material, the concentration of the guest material with respect to the host material is preferably 0.1% by mass or more and 30% by mass or less, and 0.5% by weight or more and 10% by weight or less. It is more preferable that

  In addition to the condensed polycyclic compound according to the present invention, the organic light-emitting device according to this embodiment may be a conventionally known hole-injecting material, transporting material, host material, guest material, electron-injecting material, or electron, if necessary. Transportable materials etc. can be used together. These materials may be low molecules or polymers.

  Examples of these compounds are given below.

  The hole injecting material or hole transporting material is preferably a material having high hole mobility. Low molecular and high molecular weight materials having hole injection performance or hole transport performance include triarylamine derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly (vinylcarbazole), poly (thiophene), In addition, although a conductive polymer is mentioned, of course, it is not limited to these.

  Host materials include triarylamine derivatives, phenylene derivatives, condensed ring aromatic compounds (for example, naphthalene derivatives, phenanthrene derivatives, fluorene derivatives, chrysene derivatives, etc.), organometallic complexes (for example, tris (8-quinolinolato) aluminum, etc. Organic aluminum complexes, organic beryllium complexes, organic iridium complexes, organic platinum complexes, etc.) and poly (phenylene vinylene) derivatives, poly (fluorene) derivatives, poly (phenylene) derivatives, poly (thienylene vinylene) derivatives, poly (acetylene) derivatives Of course, the polymer derivatives are not limited to these.

  Table 1 shows specific structural formulas of the host compound. The host compound may be a compound that is a derivative having the structural formula shown in Table 4. In addition to these, condensed ring compounds (for example, fluorene derivatives, naphthalene derivatives, anthracene derivatives, pyrene derivatives, carbazole derivatives, quinoxaline derivatives, quinoline derivatives, etc.), organoaluminum complexes such as tris (8-quinolinolato) aluminum, organozinc complexes, And polymer derivatives such as a triphenylamine derivative, a poly (fluorene) derivative, and a poly (phenylene) derivative, but of course not limited thereto.

  The electron injecting material or the electron transporting material is selected in consideration of the balance with the hole mobility of the hole injecting material or the hole transporting material. Examples of materials having electron injection performance or electron transport performance include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, etc. It is not limited to.

  An anode material having a work function as large as possible is preferable. For example, simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, or alloys thereof, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide, etc. It is a metal oxide. Further, conductive polymers such as polyaniline, polypyrrole, and polythiophene may be used. These electrode materials may be used alone or in combination. Further, the anode may have a single layer structure or a multilayer structure.

  On the other hand, a cathode material having a small work function is preferable. Examples thereof include alkali metals such as lithium, alkaline earth metals such as calcium, and simple metals such as aluminum, titanium, manganese, silver, lead, and chromium. Or the alloy which combined these metal single-piece | units can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, etc. can be used. A metal oxide such as indium tin oxide (ITO) can also be used. These electrode materials may be used alone or in combination. Further, the cathode may have a single layer structure or a multilayer structure.

  In the organic light-emitting device according to this embodiment, the layer containing the condensed polycyclic compound according to this embodiment and the layer made of other organic compounds are formed by the following method.

  For example, the layer is formed by a known coating method such as spin coating, dipping, casting method, LB method, and ink jet method by dissolving in a vacuum deposition method, ionization deposition method, sputtering method, plasma, or an appropriate solvent.

  Here, when a layer is formed by a vacuum deposition method, a solution coating method, or the like, crystallization or the like hardly occurs and the temporal stability is excellent. Moreover, when forming by the apply | coating method, a film | membrane can also be formed combining with a suitable binder resin.

  Examples of the binder resin include, but are not limited to, polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, urea resin, and the like. .

  Moreover, these binder resins may be used alone as a homopolymer or a copolymer, or may be used as a mixture of two or more. Furthermore, you may use together additives, such as a well-known plasticizer, antioxidant, and an ultraviolet absorber, as needed.

(Use of organic light emitting device according to this embodiment)
The organic light emitting element according to this embodiment can be used for a display device or a lighting device. In addition, it can be used for an exposure light source of an electrophotographic image forming apparatus, a backlight of a liquid crystal display device, and the like.

  The display device includes the organic light emitting element according to the present embodiment in a display unit. This display unit has a plurality of pixels. This pixel includes a TFT element as an example of the organic light emitting element according to the present embodiment and a switching element for controlling light emission luminance. In the switching element, the anode or cathode of the organic light emitting element and the drain electrode or source electrode of the thin film transistor are connected.

  The display device can be used as an image display device such as a PC, a head mounted display, or a mobile phone. The displayed image may be a two-dimensional image or a three-dimensional image.

  The display device may include an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, or the like, and may output an input image to the display unit.

  The image output apparatus may be a digital camera having an image input unit as an image pickup device such as a CCD sensor and having an image pickup optical system.

  The display device may have an input function that allows input by touching the output image. For example, a touch panel function etc. are mentioned.

  The display device may be used for a display unit of a multifunction printer.

  The organic light emitting element according to this embodiment may be used in a lighting device. This illuminating device has the organic light emitting element which concerns on this embodiment, and the inverter circuit connected to the organic light emitting element.

  The color of the illumination light of the illumination device according to the present embodiment may be white, daylight white, or other colors.

  In the case of emitting white, the light emitting part of the organic light emitting element has a plurality of light emitting layers, the compound of the present invention emits red, and the other layers emit other than red, thereby emitting white as the element.

  FIG. 2 is a schematic cross-sectional view of a display device having the organic light emitting element according to this embodiment and a TFT element connected thereto.

  In this display device, a substrate 10 made of glass or the like and a moisture-proof film 11 for protecting the TFT element or the organic compound layer are provided on the substrate 10. Reference numeral 12 denotes a metal gate electrode 12. Reference numeral 13 denotes a gate insulating film 13, and reference numeral 14 denotes a semiconductor layer.

  The TFT element 17 has a semiconductor layer 14, a drain electrode 15, and a source electrode 16. An insulating film 18 is provided on the TFT element 17. The anode 20 and the source electrode 16 of the organic light emitting element are connected via the contact hole 19.

  The display device according to the present embodiment is not limited to this configuration, and any one of the anode and the cathode may be connected to either the TFT element source electrode or the drain electrode.

  Although the organic compound layer 21 is illustrated as a single layer in the drawing, the organic compound layer 21 may be a plurality of layers. A first protective layer 23 and a second protective layer 24 are provided on the cathode 22 to suppress deterioration of the organic light emitting device.

  The light emitting luminance of the organic light emitting device according to this embodiment is controlled by a TFT device which is an example of a switching device. By providing the organic light emitting elements in a plurality of planes, an image can be displayed with each light emission luminance.

  The switching element included in the organic light emitting element according to the present embodiment is not limited to the TFT element, and an active matrix driver is formed on a substrate such as a transistor, an MIM element, or a Si substrate, and the organic light emitting element is provided on the active matrix driver. Form may be sufficient.

  This is selected depending on the definition. For example, in the case of a definition of 1 inch and QVGA, it is preferable to provide an organic light emitting element on the Si substrate.

  By driving the display device using the organic light emitting element according to the present embodiment, it is possible to perform stable display even with long-time display with good image quality.

Example 1
[Synthesis of Exemplary Compound A-1]
The synthesis was performed according to the following synthesis scheme.

Synthesis of Compound e-3 In a 50 ml three-necked flask, in a nitrogen atmosphere, Compound e-1, 0.636 g (1.2 mmol), Compound e-2, 0.371 g (1.2 mmol), Sodium carbonate, 2 g of toluene 10 ml Then, 5 ml of ethanol and 10 ml of water were added, and tetrakis (triphenylphosphine) palladium (0), 70 mg was added with stirring at room temperature in a nitrogen atmosphere. The temperature was raised to 80 degrees and stirred for 12 hours. After the reaction, the organic layer was extracted with toluene, dried over anhydrous sodium sulfate, and then purified by a silica gel column (mixed with chloroform and heptane, developing solvent) to obtain 0.540 g (yield 71%) of compound e-3 (yellow solid). It was.

Synthesis of Compound A-1 A 50 ml three-necked flask was charged with diglyme, 20 ml, diazabicycloundecene (DBU) 3.0 ml, tert-butoxy potassium, 5.0 g. In a nitrogen atmosphere, the temperature was raised to 130 ° C., Compound e-3, 0.350 g (0.56 mmol) was added, and the mixture was stirred for 2 hours. After the reaction, 20 ml of water was added to the organic layer, and the reaction solution was neutralized with concentrated hydrochloric acid. After extracting with chloroform and concentrating the organic layer, it was purified with a silica gel column (mixed with chloroform and heptane, developing solvent) to obtain 308 mg (yield 87%) of Exemplary Compound A-1 (red crystals).
¹ H NMR (CDCl ₃ , 500 MHz) σ (ppm): 8.68 (d, 1H), 8.46 (d, 1H), 8.30 (d, 1H), 8.27 (d, 1H), 8.16 (d, 1H), 8.11 (d, 1H), 8.10 (d, 1H), 7.96 (d, 1H) 7.74-7.57 (m, 11H), 7. 51-7.40 (m, 5H), 6.59 (d, 1H), 6.56 (d, 1H)
By mass spectrometry, 630, which was M + of the exemplary compound A-1, was confirmed.

When the emission spectrum in the toluene dilute solution was measured about exemplary compound A-1, the maximum light emission wavelength was 621 nm. The emission spectrum was measured by measuring the emission spectrum of a toluene solution (1 × 10 ⁻⁴ mol / l) at an excitation wavelength of 530 nm and using the first emission peak. The apparatus used was a Hitachi spectrophotometer U-3010.

(Example 2)
[Synthesis of Exemplary Compound A-3]
In the same manner as in Example 1, Compound e-1 was changed to the following Compound f-1 to synthesize Example Compound A-3.
By mass spectrometry, 743, which was M + of the exemplary compound A-3, was confirmed.
Moreover, when the emission spectrum in the toluene dilute solution was measured about Example compound A-3 like Example 1, the light emission maximum wavelength was 622 nm.

(Example 3)
[Synthesis of Exemplary Compound B-4]
In the same manner as in Example 1, Compound e-1 was changed to the following Compound f-2 to synthesize Example Compound B-4.
By mass spectrometry, 935 which was M + of the exemplary compound B-4 was confirmed.
Moreover, when the emission spectrum in the toluene dilute solution was measured about Example compound B-4 like Example 1, the emission maximum wavelength was 623 nm.

Example 4
[Synthesis of Exemplary Compound C-1]
In the same manner as in Example 1, Compound e-1 was changed to the following Compound f-3 to synthesize Example Compound C-1.
By mass spectrometry, 863, which was M + of the exemplary compound C-1, was confirmed.
Further, T1 in a toluene dilute solution was measured for Exemplified Compound C-1 in the same manner as in Example 1, and it was 622 nm.

(Example 5)
[Synthesis of Exemplary Compound A-4]
In the same manner as in Example 1, Compound e-1 was changed to the following Compound f-4 to synthesize Example Compound A-4.
By mass spectrometry, 687 which was M + of the exemplary compound A-4 was confirmed.
Moreover, when T1 in the toluene dilute solution was measured about exemplary compound A-4 like Example 1, it was 625 nm.

(Example 6)
[Synthesis of Exemplary Compound B-2]
In the same manner as in Example 1, Compound e-1 was changed to the following Compound f-5 to synthesize Example Compound B-2.
By mass spectrometry, 783 which was M + of the exemplary compound B-2 was confirmed.
Moreover, when T1 in the toluene dilute solution was measured about exemplary compound B-2 like Example 1, it was 622 nm.

(Example 7)
In this example, an organic light-emitting device having a structure in which an anode / hole transport layer / light-emitting layer / electron transport layer / cathode was sequentially provided on a substrate was produced by the method described below.

A transparent conductive support substrate (ITO substrate) obtained by depositing ITO as a positive electrode with a film thickness of 120 nm on a glass substrate was used. On this ITO substrate, the following organic compound layer and electrode layer were continuously formed by vacuum deposition by resistance heating in a vacuum chamber of 10 ⁻⁵ Pa. At this time, the opposing electrode area was 3 mm ² .
Hole transport layer (30 nm) g-1
Light emitting layer (30 nm) Host g-2, Guest: A-1 (weight ratio 1%), Assist: g-3 (weight ratio 5%)
Electron transport layer (40 nm) g-4
Metal electrode layer 1 (1 nm) LiF
Metal electrode layer 2 (100 nm) Al

  The obtained organic light-emitting device was applied with an applied voltage of 6.0 V using the ITO electrode as a positive electrode and the Al electrode as a negative electrode. Red light emission at coordinates (0.69, 0.29) was observed.

Further, for the organic light emitting device of this example, the device was continuously driven for 100 hours while maintaining the current density at 100 mA / cm ² in a nitrogen atmosphere. As a result, the luminance degradation was within 20% with respect to the initial luminance.

(Example 8)
In Example 7, the organic light emitting element was produced by the method similar to Example 6 except having made the light emitting layer guest A-1 into exemplary compound A-3.
When an applied voltage of 6.0 V was applied, a current density of 52.0 mA / cm 2, an emission luminance of 1056 cd / m 2, and red emission of CIE chromaticity coordinates (0.69, 0.29) were observed.

Example 9
In Example 7, the organic light emitting element was produced by the same method as Example 6 except having made luminous layer guest A-1 into exemplary compound B-4.
When an applied voltage of 6.0 V was applied, a current density of 51.5 mA / cm 2, an emission luminance of 1098 cd / m 2, and red emission of CIE chromaticity coordinates (0.68, 0.30) were observed.

(Example 10)
In Example 7, the organic light emitting element was produced by the method similar to Example 6 except having made the light emitting layer guest A-1 into the exemplary compound C-1.
When an applied voltage of 6.0 V was applied, a red light emission of CIE chromaticity coordinates (0.68, 0.31) was observed at a current density of 53.5 mA / cm 2 and an emission luminance of 1050 cd / m 2.

(Example 11)
In this example, a white organic light emitting device having a structure in which an anode / hole transport layer / blue light emitting layer / green light emitting layer / red light emitting layer / electron transport layer / electron injection layer / cathode are sequentially provided on a substrate is shown below. It was produced by the method.

A transparent conductive support substrate (ITO substrate) obtained by depositing ITO as a positive electrode with a film thickness of 120 nm on a glass substrate was used. On this ITO substrate, the following organic compound layer and electrode layer were continuously formed by vacuum deposition by resistance heating in a vacuum chamber of 10 ⁻⁵ Pa. At this time, the opposing electrode area was 3 mm ² .
Hole transport layer (30 nm) g-1
Blue light emitting layer (10 nm) Host g-5 (weight ratio 95.0%), guest: g-6 (weight ratio 5.0%)
Green light emitting layer (10 nm) Host g-5 (99.5% by weight), Guest: g-7 (5.0% by weight)
Red light emitting layer (10 nm) Host 1 g-5 (39.5% by weight), Host 2 g-3 (60.0% by weight), Guest: A-1 (0.5% by weight)
Electron transport layer (30 nm) g-4
Electron injection layer (1 nm) LiF
Metal electrode layer (100 nm) Al

  When the applied voltage was applied to the obtained organic light emitting device using the ITO electrode as the positive electrode and the Al electrode as the negative electrode, C.I. I. E. White light emission with a chromaticity coordinate of (0.33, 0.35) was observed.

(Example 12)
In the same manner as in Example 11, an organic light emitting device in which the guest A-1 was changed to A-3 was produced.
When the applied voltage was applied to the obtained organic light emitting device using the ITO electrode as the positive electrode and the Al electrode as the negative electrode, C.I. I. E. White light emission with chromaticity coordinates of (0.33, 0.34) was observed.

(Example 13)
In the same manner as in Example 11, an organic light emitting device in which the guest A-1 was changed to B-4 was produced.
When the applied voltage was applied to the obtained organic light emitting device using the ITO electrode as the positive electrode and the Al electrode as the negative electrode, C.I. I. E. White light emission with chromaticity coordinates of (0.34, 0.33) was observed.

4 Blue light emitting layer 5 Green light emitting layer 6 Red light emitting layer 17 TFT element 20 Anode 21 Organic compound layer 22 Cathode

Claims (9)

A condensed polycyclic compound represented by the following general formula [1]:

[1]
In the general formula [1], R _{1 to} R ₄ are each independently selected from a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Ar ₁ and Ar ₂ are each independently selected from aryl groups.
The aryl group is any one of a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a naphthyl group.
The aryl group may have an alkyl group having 1 to 4 carbon atoms.   An organic light emitting device comprising: a pair of electrodes; and an organic compound layer disposed between the pair of electrodes, wherein the organic compound layer includes the condensed polycyclic compound according to claim 1.   The organic light emitting device according to claim 2, wherein the organic compound layer includes a light emitting layer, the light emitting layer includes a host material and a guest material, and the guest material is the condensed polycyclic compound.   The organic light-emitting device according to claim 2, which emits red light. The organic compound layer has a light emitting portion, the light emitting portion has a plurality of light emitting layers,
At least one of the plurality of light emitting layers has the condensed polycyclic compound,
The plurality of light emitting layers are light emitting layers in which each light emitting layer emits different light emission colors,
The organic light-emitting element according to claim 2, wherein the organic light-emitting element emits white by mixing the different emission colors. The organic compound layer includes a plurality of light emitting layers, and at least one of the plurality of light emitting layers includes the condensed polycyclic compound and emits red light.
4. The organic light emitting element according to claim 2, wherein the organic light emitting element emits white from a mixed color of a light emitting layer other than the light emitting layer emitting red and the red color. 5.   A display device comprising a plurality of pixels, wherein the pixels include the organic light-emitting element according to claim 2 and a switching element connected to the organic light-emitting element. A display unit for displaying an image and an input unit for inputting image information;
The display unit includes a plurality of pixels, and the pixels include the organic light emitting element according to any one of claims 2 to 6 and a switching element connected to the organic light emitting element. Image input device.   An illumination device comprising: the organic light-emitting element according to claim 2; and an inverter circuit connected to the organic light-emitting element.