JP5907289B1 - Material for organic electroluminescence device and use thereof - Google Patents

Abstract

When used in an organic EL device, it can be formed by vapor deposition or spin coating, and has excellent performance ((high glass transition temperature, high luminous efficiency, low voltage drive, high color purity, long life, deep Provided is a light-emitting material that exhibits red (long wavelength) and can be suitably used particularly for a red light-emitting material.3,6-Dithiophenylpyrrolo [3,4-c] pyrrole-1,4 A luminescent material comprising a (2H, 5H) -dione derivative and a material having a peak wavelength of the photoexcitation emission spectrum of the solid film between 550 and 630 nm.

Description

  The present invention relates to a material for a novel organic electroluminescence element (hereinafter abbreviated as an organic EL element) used for a planar light source and display and its use. More specifically, when used in an organic EL device, it can be formed by vapor deposition or spin coating, and has excellent performance (high glass transition temperature, high luminous efficiency, low voltage drive, high color purity, long life, deep The present invention relates to a material for an organic EL element that exhibits red (long wavelength light emission) and can be suitably used particularly for a red light emitting material.

In recent years, organic EL elements have been required to have a long lifetime. There are various factors that can affect the lifetime of the device. One of the factors is that the glass transition temperature ( _Tg ) of the material constituting the device has a significant effect on the lifetime of the device. Yes. That is, it is pointed out that when the temperature of the element exceeds the Tg of the constituent material due to the use environment of the element or the heat generated during driving, the constituent material is crystallized and a non-light emitting region called a dark spot is generated. ing. Therefore, a material exhibiting a higher T _g has been demanded (Non-Patent Document 1).

  Among these organic EL elements, organic EL elements that emit red light have been researched on elements using various materials because of their usefulness. However, a small amount of dopant is co-deposited in the host material. A method of forming a light emitting layer by mixing by a method and obtaining light emission from a dopant has been studied as an effective method (Non-Patent Document 2). In this method, an organic EL device that emits orange to red light using tris (8-hydroxyquinolinate) aluminum as a host material and 4H-pyran derivatives such as DCM, DCJ, DCJT, and DCJTB as a dopant is reported. ing.

  Moreover, several patents are reported about the organic EL element using the compound which has a 1, 4- diketopyrrolo (3,4-c) pyrrole structure known as a red pigment (patent documents 1-6). However, all are 1,4-diketopyrrolo (3,4-c) pyrrole structures having a benzene ring.

  On the other hand, it has been reported that the absorption wavelength of a 1,4-diketopyrrolo (3,4-c) pyrrole derivative having a pyrrole ring, a furan ring or a thiophene ring is increased (Patent Document 7). However, since the crystallinity is high, there is a disadvantage that the lifetime of the element is short and it is difficult to be a practical material.

Japanese Patent Laid-Open No. 2-29691 JP-A-5-320633 JP 2001-139940 A WO03 / 048268 pamphlet JP 2003-155286 A JP 2010-235870 A Japanese Patent Application Laid-Open No. 2006-117591

Appl. Phys. Lett. 51, 913, 1987 Macromol. Symp. 125, 34-36 and 49-58, 1997

  An object of the present invention is to provide an organic EL element for obtaining high-luminance red light described in the prior art, and an organic EL element using a 4H-pyran derivative as a dopant has an x value of CIE1931 chromaticity coordinate system of 0. There is a problem that the emission is orange or orange-red light of about 58 to 0.62, not red or deep red of 0.62 or more, and in addition, the drive voltage is high and the light emission efficiency is low. In addition, in an organic EL device using a compound having a 1,4-diketopyrrolo (3,4-c) pyrrole structure as a dopant, an element with high color purity can be produced, but the concentration is high due to high molecular cohesion. Quenching is likely to occur and control of the doping concentration is an important issue. Therefore, there has been a demand for a material for an organic EL element that can obtain deep red light emission with high color purity that exhibits high light emission efficiency and long life without causing problems such as concentration quenching.

As a result of intensive studies to solve the above problems, the present inventors have arrived at the present invention. That is, the present invention comprises a material represented by the following general formula [ 5 ] and / or the following general formula [ 6 ], and a material having a peak wavelength of the photoexcitation emission spectrum of the solid film of 550 to 630 nm. The present invention relates to a light emitting material.

General formula [5]

(In the formula, each X independently represents a sulfur atom or an oxygen atom, and R ²⁶ and R ²⁷ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted group. Or an unsubstituted aryloxycarbonyl group,
R ^{28 to} R ⁴¹ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted silyl group, or a substituted amino group. Represent. )

General formula [6]

(In the formula, each X independently represents a sulfur atom or an oxygen atom, and R ⁴² and R ⁴³ each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted group. Or an unsubstituted aryloxycarbonyl group,
R ^{44 to} R ⁵⁷ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted silyl group, or a substituted amino group. Represent. )

Further, the present invention is represented by the general formula [5], and / or materials may be represented by a general formula [6], represented by the following general formula [7], and / or the following general formula [8] Materials It is related with said luminescent material which is.

General formula [7]

(Wherein R ⁵⁸ and R ⁵⁹ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryloxycarbonyl group;
R ^{60 to} R ⁶³ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted silyl group, or a substituted amino group. Represent. )

General formula [8]

(Wherein R ⁶⁴ and R ⁶⁵ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryloxycarbonyl group;
R ^{66 to} R ⁶⁹ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted silyl group, or a substituted amino group. Represent. )

  Further, the present invention provides an organic electroluminescence device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes composed of an anode and a cathode. The present invention relates to an organic electroluminescence element including a material.

  The organic EL device material containing the compound of the present invention has a high color purity and deep (long wavelength) red light emission due to the specific structure of the material, hardly causes concentration quenching, has high light emission luminance and long life. It is characterized by being compatible. Furthermore, an organic EL device created using this material can be suitably used as a flat panel display such as a wall-mounted television or a flat light emitter, such as a light source such as a copying machine or a printer, a light source such as a liquid crystal display or instruments, It can be applied to display boards, beacon lights, etc. In particular, it is suitable for applications that are difficult in the prior art, such as agricultural light sources adapted to the absorption band of chlorophyll due to the deep red color, and medical sensors that utilize the difference between red and near infrared absorption characteristics depending on the presence or absence of oxygen in hemoglobin. I can do it.

  Hereinafter, embodiments of the present invention will be described in detail.

 There are various embodiments of the organic EL element in the present invention, and one of the embodiments will be described here. The material represented by the general formula [1] and / or the general formula [2], and the solid film An organic EL element using a light-emitting material including a material having a peak wavelength of a photoexcitation emission spectrum between 550 and 630 nm. Here, the solid film of the material is a single film of the material. The photoexcitation emission spectrum of the solid film is a photoexcitation emission spectrum when the thin film is irradiated with excitation light.

 The excitation light for obtaining the photoexcitation emission spectrum uses a wavelength at which the target material single film has light absorption.

 In general, photoexcitation luminescence is fluorescence, but some compounds such as an iridium complex and a platinum complex can emit phosphorescence by the heavy atom effect.

 When the photoexcitation emission spectrum of the solid film has two or more peaks, the peak wavelength of the strongest emission intensity is set as the peak wavelength of the photoexcitation emission spectrum of the solid film.

  In the present invention, with respect to light emission, there are three types of light emission from a compound or material composition: (1) photoexcitation light emission from a solution, (2) photoexcitation light emission from a solid film, and (3) EL light emission from an element. However, these are the same phenomena only in the molecular state and the excitation mode. Therefore, when it is not necessary to distinguish between states and styles, it is simply referred to as light emission unless otherwise specified. However, the light emission related to the element itself and the film constituting the element is all EL light emission unless otherwise specified.

  As one form of the organic EL element in the present invention, the material represented by the general formula [1] and / or the general formula [2] is a dopant material in the light emitting layer, and the peak wavelength of the photoexcitation emission spectrum of the solid film is The material that is between 550 and 630 nm is the host. When the excitation mechanism of the dopant material is regarded as energy transfer from the host material, it is ideal that there is a large overlap between the emission spectrum of the host and the absorption spectrum of the dopant. Considering the Stokes shift of the dopant (difference between the absorption peak wavelength and the emission peak wavelength), it is understood that a host having an emission spectrum from yellow to red is preferable for a red emitting dopant.

  In a specific peak wavelength, if the peak wavelength on the short wavelength side is 550 nm or more, it is suitable as a host compound in a light emitting layer for an organic EL element that can emit red light. On the long wavelength side, if the area on the long wavelength side of the emission spectrum of the host is larger than the absorption spectrum of the dopant, energy transfer cannot be expected because the area is exceeded, so the emission peak of the host is larger than the absorption peak wavelength of the dopant. While shorter wavelengths are preferred, on the other hand, if the host spectrum is broad, it will sufficiently cover the spectral range of the dopant, so if the area overlap is large, the characteristics of the dopant itself will Depending on the compatibility with the host, it is possible to expect not only an improvement in color purity but also a significant improvement in light emission luminance and efficiency, rather than light emission from a host-only layer without addition of a dopant.

  However, the region of 630 nm or more in the emission spectrum of the host emits red to red light directly without transferring energy to the dopant when a red light emitting dopant is added. Purity will deteriorate. Therefore, it is preferable that the emission peak wavelength of the host is 630 nm or less and that the area of the region of 630 nm or more is as small as possible. If the combination of the host and dopant does not match, even if both have strong emission intensity, energy transfer from the host to the dopant will not be successful, so good results will not be obtained, and in some cases, emission from the host will remain Therefore, the target color tone may not be obtained.

  In addition, the single film of the dopant material represented by the general formula [1] and / or the general formula [2] has a lower emission intensity because the excitation energy is deactivated due to the proximity of the same kind of molecule. “Concentration quenching” is likely to occur, and the emission spectrum of the single dopant film is often considerably longer than that of the doping film used in the device. The compound used as a dopant is contained in an amount of about 0.01 to 10% by weight based on the compound used as a host as a normal EL device light emitting film, but the emission spectrum slightly changes depending on the compounding ratio of the dopant. The area distribution of the spectrum also changes slightly.

  Film formation for obtaining a solid film of host material may be performed by a film formation method used for an element to be described later such as vapor deposition or spin coating. However, not only observation of a photoexcitation emission spectrum but also determination of film formation aptitude. Therefore, it is preferable to use the same film formation method as that for the element formation and to keep the conditions as uniform as possible.

  In the photoexcitation emission spectrum of a solid film, depending on the properties of the film and the specifications of the device, it is often difficult to eliminate the influence of scattered light that reaches the detection part of the device due to the diffuse reflection of the excitation light on the film surface and others. The scattered light portion may be removed by data processing after measurement, or it is also necessary to judge from the spectrum from the longer wavelength portion by avoiding scattered light of 400 nm or more, regardless of the range of 400 to 800 nm. In some cases.

  It is known that the emission color of the organic EL element is easily affected by light interference because the film thickness of the ITO and the organic layer used is approximately the same as the wavelength in the visible light region. For this reason, even if the same compound is used, if the film thickness of ITO is different, or if the structure and film thickness of the organic layer including not only the light emitting layer but also the hole injection layer and the electron injection layer are changed, the chromaticity In some cases, even if the photoexcitation emission spectrum of a solid film is measured at the same film thickness as the light emitting layer of the device, the order of the photoexcitation emission spectrum and the order of the EL emission spectrum between the compounds may be reversed. Sometimes it is. Conversely, by actively utilizing this effect, the chromaticity can be brought close to the target numerical value.

  The relationship between the host and the dopant in the light emitting layer is taken from the functional viewpoint of the film forming function and the light emitting function, and does not merely indicate a quantitative ratio. The ratio of the host is 50% by weight to 99.99% by weight, more preferably 90% by weight to 99.9%, from the viewpoint of making full use of the film forming property of the host and efficiently emitting light without quenching the concentration of the dopant. % By weight.

  On the contrary, the proportion of the dopant is usually 50% by weight or less, preferably 25% by weight or less, and more preferably 10% by weight or less.

  As a form other than the above, it is possible to use a light emission assist dopant material, and this assist dopant material has a function of smoothly transferring energy from the host material to the dopant material. Representative examples of this include Technical Report of IEICE. OME, Organic Electronics 100 (651), 13-18, 2001-03-02, Surface Technology. 56, No. 5, 2005, etc. are reported.

  Also in the present application, as one embodiment, the light emitting layer has a general wavelength [1] and / or a material for an organic electroluminescence element represented by the following general formula [2], or a peak wavelength of a photoexcitation emission spectrum of a solid film. May include a component other than the material having a thickness of 550 to 630 nm, and the component may serve as a host material or an assist dopant material. Furthermore, the material whose peak wavelength of the photoexcitation emission spectrum of the solid film is between 550 and 630 nm may fulfill the function of the assist dopant material.

  As another form of the organic EL device in the present invention, the material represented by the general formula [1] and / or the general formula [2] is a dopant material in the light emitting layer, and the peak of the photoexcitation emission spectrum of the solid film A material whose wavelength is between 550 and 630 nm is an assist dopant. In this case, as the host material, a conventionally known light-emitting material or a material having a peak wavelength of the photoexcitation emission spectrum of the solid film between 550 to 630 nm, which is different from the assist dopant, can be used.

  The ratio of the host in the light emitting layer comprising the dopant, the assist dopant and the host is preferably 50% by weight to 99.9% by weight, and particularly preferably 65% by weight to 95% by weight.

  Moreover, as a weight ratio of a dopant and an assist dopant in the light emitting layer which consists of a dopant, an assist dopant, and a host, 1: 20-1: 1 are preferable.

  The organic EL element includes a material other than the material having a peak wavelength of the photoexcitation emission spectrum of the solid film of 550 to 630 nm and the dopant material represented by the general formula [1] and / or the general formula [2], for example, In addition, various polymers to be described later for enhancing the film-forming ability, materials having a peak wavelength of the photoexcitation emission spectrum of the solid film between 550 and 630 nm, and the general formula [1] and / or the general formula [2] A light emitting material other than the dopant material represented, a hole injection material, an electron injection material, or various additives such as an antioxidant, an ultraviolet absorber, and a plasticizer may be included.

  Specific compounds that can be used as a host material in the present invention include quinolinol complexes of metals such as aluminum and zinc, benzoazole-based metal complexes such as benzoxazole complexes, benzothiazole complexes, benzimidazole complexes, and benzotriazole complexes, Bisstyryl derivative, stilbene derivative, butadiene derivative, benzidine type triphenylamine derivative, styrylamine type triphenylamine derivative, diaminoanthracene type triphenylamine derivative, diaminophenanthrene type triphenylamine derivative, rubrene, coumarin dye, phthaloperinone, naphthaloperinone, Polymer materials such as quinacridone derivatives, polyparaphenylene vinylene derivatives, oligothiophene derivatives, rare earth metal complexes such as terbium, Etc. involved luminescent material triplet state which is a metal complex or the like such as Rijiumu numerous those materials exhibiting red light emission from yellow are mentioned as candidates. Of these, quinolinol complexes, benzoazole complexes, bisstyryl derivatives, triphenylamine derivatives, etc., have a relatively simple structure and have blue to blue-green photoexcitation emission, so they are used as green to yellow light-emitting materials. It is preferable to extend the wavelength of photoexcited light emission by introducing a condensed aromatic ring or heterocyclic ring, ring expansion, or attaching a polar, particularly electron-donating substituent.

  Among these, a compound having a perylene ring is particularly effective as a component of the host material. The reason for this is that a compound having a perylene ring can easily obtain a compound having a strong yellow light emission particularly in a solid state due to the addition of a substituent having a relatively simple structure, and many of the compounds having an emission spectrum extending over a wide wavelength are short. A tail is drawn on each of the wavelength and long wavelength sides.

  The material represented by the general formula [1] and / or the general formula [2] of the present invention does not emit so strong fluorescence in the solid state, and the coloration of the thin film is strong. In addition, the material has a relatively narrow emission spectrum.

  Hereinafter, the material represented by the general formula [1] and / or the general formula [2] will be described in detail.

In the organic EL device material represented by the general formula [1], R ¹ and R ² are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxycarbonyl. Group, or a substituted or unsubstituted aryloxycarbonyl group, and R ^{3 to} R ⁸ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or It represents an unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, a substituted silyl group, or a substituted amino group. However, any of R ^{3 to} R ⁸ represents a substituent represented by the general formula [3] or the general formula [4].

Examples of the unsubstituted alkyl group represented by R ¹ and R ^{2 in} the present invention include a linear alkyl group, a cyclic alkyl group, and an aliphatic heterocyclic group. The linear alkyl group includes a methyl group, an ethyl group, and the like. Propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, pentadecyl group, octadecyl group, etc. Examples thereof include a linear alkyl group having 1 to 18 carbon atoms.

  Examples of the cyclic alkyl group include cycloalkyl groups having 3 to 18 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and cyclooctadecyl group.

  The substituted alkyl group includes a fluoromethyl group, a chloromethyl group, a bromomethyl group, a benzyl group, a 4-biphenylylmethyl group, a 4- (p-terphenylyl) methyl group, a 1-naphthylmethyl group, and a 2-naphthylmethyl group. , 9-phenanthrylmethyl group, 9-anthrylmethyl group, 2-phenethyl group, 2- (4-biphenylyl) ethyl group, 2- {4- (p-terphenylyl)} ethyl group, 2- (1- Naphthyl) ethyl group, 2- (2-naphthyl) ethyl group, 2- (9-phenanthryl) ethyl group, 2- (9-anthryl) ethyl group, 3-phenylpropyl group, 3- (4-biphenylyl) propyl group , 3- {4- (p-terphenylyl)} propyl group, 3- (1-naphthyl) propyl group, 3- (2-naphthyl) propyl group, 3- (9-phenanthri ) Propyl group, 3- (9-anthryl) propyl group, 2-thienylmethyl group, 2-benzo [b] thienylmethyl group, 2-naphtho [2,3-b] thienylmethyl group, 2-furylmethyl group, (2H-pyran-3-yl) methyl group, 1-isobenzofuranylmethyl group, 1-methyl-2-pyrrolylmethyl group, 1-methyl-2-imidazolylmethyl group, 2-pyrazinylmethyl group, 2-pyridylmethyl group 2-pyrimidinylmethyl group, 3-pyridazinylmethyl group, 3-methylcyclohexyl group, 3.5-dimethylcyclohexyl group and the like.

  Examples of the aliphatic heterocyclic group include 1,3-dioxolanyl group, 1,3-dioxanyl group, 1,4-dioxanyl group, 2-tetrahydrofuryl group, 2-morpholino group, 4-morpholino group, piperidino group and the like. And a monovalent aliphatic heterocyclic group having 3 to 18 carbon atoms.

Examples of the unsubstituted aryl group represented by R ¹ and R ^{2 in} the present invention include a single ring, a condensed ring, a ring assembly hydrocarbon group, and an aromatic heterocyclic group.

  Here, the monocyclic aromatic hydrocarbon group has 6 carbon atoms such as phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, p-cumenyl group and mesityl group. -18 monocyclic aromatic hydrocarbon groups.

  Examples of the condensed ring hydrocarbon group include 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 5-anthryl group, 1-phenanthryl group, 9-phenanthryl group, 1-acenaphthyl group, Examples thereof include condensed ring hydrocarbon groups having 10 to 18 carbon atoms such as 2-azurenyl group, 1-pyrenyl group and 2-triphenylyl group.

  Examples of the ring assembly hydrocarbon group include ring assembly hydrocarbon groups having 12 to 18 carbon atoms such as an o-biphenylyl group, an m-biphenylyl group, and a p-biphenylyl group.

Furthermore, examples of the aromatic heterocyclic group include triazolyl group, 3-oxadiazolyl group, 2-furanyl group, 3-furanyl group, 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 1- Pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrazyl group, 2-oxazolyl group, 3-isoxazolyl group, 2 -Thiazolyl group, 3-isothiazolyl group, 2-imidazolyl group, 3-pyrazolyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8 -Quinolyl group, 1-isoquinolyl group, 2-quinoxalinyl group, 2-benzofuryl group, 2-benzothienyl group, N-indolyl group, N-carbazolyl group,
Examples thereof include aromatic heterocyclic groups having 2 to 18 carbon atoms such as N-acridinyl group, 2-thiophenyl group, 3-thiophenyl group, bipyridyl group and phenanthryl group.

The unsubstituted alkoxycarbonyl group for R ¹ and R ^{2 in} the present invention is preferably an alkoxycarbonyl group having 2 to 14 carbon atoms. Examples of such include, but are not limited to, the following examples: methoxycarbonyl group, ethoxycarbonyl group, and benzyloxycarbonyl group.

The unsubstituted aryloxycarbonyl group for R ¹ and R ^{2 in} the present invention is preferably an aryloxycarbonyl group having 2 to 14 carbon atoms. As such, although not limited to the following examples, a phenoxycarbonyl group and a naphthyloxycarbonyl group are exemplified.

The unsubstituted alkyl group represented by R ^{3 to} R ^{8 in} the present invention has the same meaning as the unsubstituted alkyl group in R ¹ and R ² .

The unsubstituted aryl group represented by R ^{3 to} R ^{8 in} the present invention has the same meaning as the unsubstituted aryl group in R ¹ and R ² .

As the unsubstituted alkoxyl group of R ^{3 to} R ^{8 in} the present invention, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a tert-butoxy group, an octyloxy group, a tert-octyloxy group, and the like. Of the alkoxyl group.

Examples of the unsubstituted aryloxy group represented by R ^{3 to} R ^{8 in} the present invention include a phenoxy group, a 4-tert-butylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and a 9-anthryloxy group. Examples include aryloxy groups having 6 to 14 carbon atoms.

Examples of the unsubstituted thioalkoxyl group represented by R ^{3 to} R ^{8 in} the present invention include carbon such as thiomethoxy group, thioethoxy group, thiopropoxy group, thiobutoxy group, tert-thiobutoxy group, thiooctyloxy group, and tert-octylthioxy group. The thioalkoxyl group of number 1-8 is mentioned.

Examples of the unsubstituted thioaryloxy group represented by R ^{3 to} R ^{8 in} the present invention include a thiophenoxy group, a 4-tert-butylthiophenoxy group, a 1-naphthylthioxy group, a 2-naphthylthioxy group, and a 9-anne. Examples thereof include a thioaryloxy group having 6 to 14 carbon atoms such as a thiryloxy group.

The substituted silyl group of R ^{3 to} R ^{8 in} the present invention is a substituted or unsubstituted alkyl group, or a silyl group substituted by a substituted or unsubstituted aryl group, and is a monoalkylsilyl group or monoarylsilyl group. And substituted silyl groups such as a group, a dialkylsilyl group, a diarylsilyl group, a trialkylsilyl group, and a triarylsilyl group.

  Here, as the monoalkylsilyl group, a monoalkylsilyl group such as a monomethylsilyl group, a monoethylsilyl group, a monobutylsilyl group, a monoisopropylsilyl group, a monodecanesilyl, a monoicosanesilyl group, or a monotriacontanesilyl group Is mentioned.

  Examples of the monoarylsilyl group include monoarylsilyl such as monophenylsilyl group, monotolylsilyl group, mononaphthylsilyl group, and monoanthrylsilyl group.

Examples of the dialkylsilyl group include dialkylsilyl groups such as dimethylsilyl group, diethylsilyl group, dimethylethylsilyl group, diisopropylsilyl group, dibutylsilyl group, dioctylsilyl group, and didecanesilyl group.

  Examples of the diarylsilyl group include diarylsilyl such as diphenylsilyl group and ditolylsilyl group.

  Examples of the trialkylsilyl group include trialkylsilyl groups such as trimethylsilyl group, triethylsilyl group, dimethylethylsilyl group, triisopropylsilyl group, tributylsilyl group, and trioctylsilyl group.

  Examples of the triarylsilyl group include triarylsilyl groups such as a triphenylsilyl group and a tolylsilylsilyl group.

The substituted amino group of R ^{3 to} R ^{8 in} the present invention includes a mono-substituted amino group and a di-substituted amino group. As the mono-substituted amino group, an N-methylamino group and an N-ethylamino group are di-substituted. As the amino group, N, N-diethylamino group, N, N-diisopropylamino group, N, N-dibutylamino group, N-benzylamino group, N, N-dibenzylamino group, N-phenylamino group, N -Phenyl-N-methylamino group, N, N-diphenylamino group, N, N-bis (m-tolyl) amino group, N, N-bis (p-tolyl) amino group, N, N-bis (p -Biphenylyl) amino group, bis [4- (4-methyl) biphenylyl] amino group, N-α-naphthyl-N-phenylamino group, N-β-naphthyl-N-phenylamino group, etc. Substituted amino groups of And the like.

In the organic EL device material represented by the general formula [2], an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxycarbonyl group, and an unsubstituted aryloxy group represented by R ⁹ and R ¹⁰ The carbonyl group has the same meaning as the unsubstituted alkyl group, unsubstituted aryl group, unsubstituted alkoxycarbonyl group, and unsubstituted aryloxycarbonyl group in R ¹ and R ² .

In the organic EL device material represented by the general formula [2], an unsubstituted alkyl group of R ^{11 to} R ¹⁶ , an unsubstituted aryl group, an unsubstituted alkoxyl group, an unsubstituted aryloxy group, an unsubstituted As the thioalkoxyl group, the unsubstituted thioaryloxy group, the substituted silyl group, and the substituted amino group, an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxyl group, an unsubstituted group in R ^{3 to} R ⁸ It is synonymous with a substituted aryloxy group, an unsubstituted thioalkoxyl group, an unsubstituted thioaryloxy group, a substituted silyl group, and a substituted amino group.

In the general formula [3] and the general formula [4], an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxyl group, or an unsubstituted aryloxy group represented by R ^{17 to} R ¹⁸ and R ^{20 to} R ²² Groups, unsubstituted thioalkoxyl groups, unsubstituted thioaryloxy groups, substituted silyl groups, and substituted amino groups include unsubstituted alkyl groups, unsubstituted aryl groups, and unsubstituted amino groups in R ^{3 to} R ⁸ . It is synonymous with an alkoxyl group, an unsubstituted aryloxy group, an unsubstituted thioalkoxyl group, an unsubstituted thioaryloxy group, a substituted silyl group, and a substituted amino group.

  Y in general formula [3] and general formula [4] is a carbon atom having a hydrogen atom, a carbon atom having a substituent, or a nitrogen atom. The substituent which the carbon atom may have is the above-mentioned substituent or unsubstituted alkyl group, substituted or unsubstituted aryl group, unsubstituted alkoxyl group, unsubstituted aryloxy group, substituted or unsubstituted A thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, and a substituted silyl group.

In the organic EL device material represented by the general formula [5] and the general formula [6], an unsubstituted alkyl group, an unsubstituted aryl group, or an unsubstituted alkoxy group represented by R ²⁶ and R ²⁷ , R ⁴² and R ⁴³ Examples of the carbonyl group and the unsubstituted aryloxycarbonyl group include an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxycarbonyl group, and an unsubstituted aryl in R ¹ and R ² . Synonymous with oxycarbonyl group.

In the general formula [5] and an organic EL element material represented by the general formula [6], unsubstituted alkyl groups R ²⁸ to R ^41, and R ⁴⁴ to R ^57, unsubstituted aryl groups, unsubstituted As an alkoxyl group, an unsubstituted aryloxy group, an unsubstituted thioalkoxyl group, an unsubstituted thioaryloxy group, a substituted silyl group, and a substituted amino group, an unsubstituted alkyl group in R ^{3 to} R ⁸ , It is synonymous with an unsubstituted aryl group, an unsubstituted alkoxyl group, an unsubstituted aryloxy group, an unsubstituted thioalkoxyl group, an unsubstituted thioaryloxy group, a substituted silyl group, and a substituted amino group.

In the organic EL device material represented by the general formula [7] and the general formula [8], an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxy group represented by R ⁵⁸ and R ⁵⁹ , R ⁶⁴ and R ⁶⁵ The carbonyl group and the unsubstituted aryloxycarbonyl group include an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxycarbonyl group, and an unsubstituted aryloxy group in R ¹ and R ² . Synonymous with carbonyl group.

In the organic EL device material represented by the general formula [7] and the general formula [8], an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted aryl group of R ^{60 to} R ⁶² and R ^{66 to} R ⁶⁹ As an alkoxyl group, an unsubstituted aryloxy group, an unsubstituted thioalkoxyl group, an unsubstituted thioaryloxy group, a substituted silyl group, and a substituted amino group, an unsubstituted alkyl group in R ^{3 to} R ⁸ , It is synonymous with an unsubstituted aryl group, an unsubstituted alkoxyl group, an unsubstituted aryloxy group, an unsubstituted thioalkoxyl group, an unsubstituted thioaryloxy group, a substituted silyl group, and a substituted amino group.

  The above-mentioned alkyl group, aryl group, alkoxycarbonyl group, aryloxycarbonyl group, alkoxyl group, aryloxy group, thioalkoxyl group, thioaryloxy group, silyl group, or amino group, It may be substituted with a substituent described in the general formula [1]. These substituents may be bonded to each other to form a ring.

Further, R ^{17 to} R ¹⁸ and R ^{20 to} R ²¹ may be bonded to each other to form a ring, and specific examples thereof include a benzene ring, a cyclohexyl ring, a pyridine ring, a pyrrole ring, For example, a furan ring or a thiophene ring is formed.

Further, at least one of R ^{3 to} R ⁸ and at least one of R ^{11 to} R ¹⁶ are substituents represented by the general formula [3] or the general formula [4], and in particular, R ³ and When general formula [3] or general formula [4] is bonded to one of R ⁶ and one of R ¹² and R ¹⁵ , general formula [3] or general formula [4] is electron donated. As an electronic effect based on this, the absorption wavelength of the molecule is increased.

In addition, the number of substitution by the general formula [3] or the general formula [4] is the longest wavelength (deep red coloration) by replacing the positions of R ³ and R ⁶ , and R ¹² and R ¹⁵ . ) Is possible. However, the molecular weight of these organic EL device materials is preferably 2000 or less, and more preferably 1500 or less. This is because, when the molecular weight is large, there is a concern that the vapor deposition property in the case of producing an element by vapor deposition is deteriorated.

  Table 1 below shows typical examples of the organic EL element material represented by the general formula [1] or the general formula [2] that can be used as the organic EL element material of the present invention. It is not limited to these.

  Next, the material used in the present invention for which the peak wavelength of the photoexcitation emission spectrum of the solid film is between 550 and 630 nm will be described.

General formula [1] and / or general formula [2], or general formula [5], and / or general formula [6], or general formula [7], and / or general formula [8] of this application. The peak wavelength of the photoexcitation emission spectrum of the solid film shown in the present application is between 550 and 630 nm, with respect to the range of 550 to 630 nm in which the main portion such as the peak of the absorption spectrum of the material represented by The materials are overlapped by their photoexcitation luminescence.

  Examples of materials that meet the above conditions include monoaminoperylene derivatives, diaminoperylene derivatives, perylene derivatives, diketopyrrolopyrrole derivatives, pyromethene complexes, pyran derivatives, naphthacene derivatives, styryl derivatives, iridium complexes, platinum complexes, and the like.

  Although not limited to the present invention, photoexcitation luminescence emitted by a material having a peak wavelength of the photoexcitation emission spectrum of the solid film between 550 and 630 nm includes fluorescence, phosphorescence, and Nature Communications 5, Article number: 4016, etc. The heat-activated delayed fluorescence (TADF) etc. which are reported are mentioned, These light emission may be compounded.

  Details of the monoaminoperylene derivative will be described below. As for organic EL elements having a perylene structure, for example, JP-A-10-251633, JP-A-11-144869, JP-A-2001-11031, JP-A-2001-176664, 2002-2002. No. 129043 and JP-A-2003-201472 are known.

  A monoaminoperylene derivative of a material having a peak wavelength of a photoexcitation emission spectrum of a solid film between 550 and 630 nm shown in the present application is represented by the following general formula [9].

General formula [9]

(In the formula, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group,
R ^{101 to} R ¹¹¹ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, substituted or unsubstituted It represents an unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, or a substituted silyl group. )

In the material represented by the general formula [9], the unsubstituted alkyl group and the unsubstituted aryl group of Ar ¹ and Ar ² are the unsubstituted alkyl group in the general formulas [1] and [2], It is synonymous with a substituted aryl group.

Further, in the material represented by the general formula [9], an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxyl group, an unsubstituted aryloxy group, an unsubstituted thio group of R ^{101 to} R ¹¹¹ is used. An alkoxyl group, an unsubstituted thioaryloxy group, and a substituted silyl group are an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxyl group, an unsubstituted aryl group in the general formulas [1] and [2]. -Synonymous with a ruoxy group, an unsubstituted thioalkoxyl group, an unsubstituted thioaryloxy group, and a substituted silyl group.

  The alkyl group, aryl group, alkoxyl group, aryloxy group, thioalkoxyl group, thioaryloxy group, or silyl group described above is substituted by the substituents described in the general formulas [1] and [2]. May be.

  Table 2 below shows representative examples of the material represented by the general formula [9] that can be used in the present invention, but the present invention is not limited to these.

Table 2

  Details of the diaminoperylene derivative will be described below. As for an organic EL element having a diaminoperylene structure, for example, JP-A-2002-3833 is known.

  The diaminoperylene derivative of the material having a peak wavelength of the photoexcitation emission spectrum of the solid film between 550 and 630 nm shown in the present application is represented by the following general formula [10] and general formula [11].

Formula [10]

(In the formula, Ar ^{3 to} Ar ⁶ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group,
R ^{112 to} R ¹²¹ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, substituted or unsubstituted It represents an unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, or a substituted silyl group. )

In the material represented by the general formula [10], the unsubstituted alkyl group and the unsubstituted aryl group represented by Ar ^{3 to} Ar ⁶ are the unsubstituted alkyl group and the unsubstituted alkyl group in the general formulas [1] and [2]. It is synonymous with a substituted aryl group.

Further, in the material expressed by the general formula [10], an unsubstituted alkyl group R ¹¹² to R ^121, unsubstituted aryl groups, unsubstituted alkoxy groups, unsubstituted ant - aryloxy group, unsubstituted thio An alkoxyl group, an unsubstituted thioaryloxy group, and a substituted silyl group are an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxyl group, an unsubstituted aryl group in the general formulas [1] and [2]. -Synonymous with a ruoxy group, an unsubstituted thioalkoxyl group, an unsubstituted thioaryloxy group, and a substituted silyl group.

  The alkyl group, aryl group, alkoxyl group, aryloxy group, thioalkoxyl group, thioaryloxy group, or silyl group described above is substituted with the substituents described in the general formulas [1] and [2]. May be.

General formula [11]

(Wherein Ar ^{7 to} Ar ¹⁰ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group,
R ^{122 to} R ¹³¹ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, substituted or unsubstituted It represents an unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, or a substituted silyl group. )

In the material represented by the general formula [11], the unsubstituted alkyl group and the unsubstituted aryl group of Ar ^{7 to} Ar ¹⁰ are the unsubstituted alkyl group in the general formulas [1] and [2], It is synonymous with a substituted aryl group.

Further, in the material expressed by the general formula [11], an unsubstituted alkyl group R ¹²² to R ^131, unsubstituted aryl groups, unsubstituted alkoxy groups, unsubstituted ant - aryloxy group, unsubstituted thio An alkoxyl group, an unsubstituted thioaryloxy group, and a substituted silyl group are an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxyl group, an unsubstituted aryl group in the general formulas [1] and [2]. -Synonymous with a ruoxy group, an unsubstituted thioalkoxyl group, an unsubstituted thioaryloxy group, and a substituted silyl group.

The alkyl group, aryl group, alkoxyl group, aryloxy group, thioalkoxyl group, thioaryloxy group, or silyl group described above is substituted with the substituents described in the general formulas [1] and [2]. May be.

  Table 3 below shows typical examples of materials represented by the general formula [10] and the general formula [11] that can be used in the present invention, but the present invention is not limited to these.

Table 3

  Details of the dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative will be described below. Further, as an organic EL device using a compound having a dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative as a dopant, for example, Japanese Patent Application Laid-Open No. 10-125 No. -329595, JP-A-11-233261, JP-A 2000-48958, and JP-A-2000-86549 are known.

  Dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] of a material in which the peak wavelength of the photoexcitation emission spectrum of the solid film shown in the present application is between 550 and 630 nm The perylene derivative is represented by the following general formula [12].

Formula [12]

Wherein R ^{132 to} R ¹⁵¹ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy Represents a group, a substituted or unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, or a substituted silyl group.)

In the material represented by the general formula [12], an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxyl group, an unsubstituted aryloxy group, an unsubstituted thio group of R ^{132 to} R ¹⁵¹ An alkoxyl group, an unsubstituted thioaryloxy group, and a substituted silyl group are an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted alkoxyl group, an unsubstituted aryl group in the general formulas [1] and [2]. -Synonymous with a ruoxy group, an unsubstituted thioalkoxyl group, an unsubstituted thioaryloxy group, and a substituted silyl group.

  The alkyl group, aryl group, alkoxyl group, aryloxy group, thioalkoxyl group, thioaryloxy group, or silyl group described above is substituted with the substituents described in the general formulas [1] and [2]. May be.

  Hereinafter, typical examples of the material represented by the general formula [12] that can be used in the present invention are shown in Table 4, but the present invention is not limited to these.

Table 4

  Details of the diketopyrrolopyrrole derivative will be described below. As for organic EL elements having a diketopyrrolopyrrole structure, for example, WO2003-048268, JP2006-160982A, and JP2006-160982A are known.

  The diketopyrrolopyrrole derivative of the material whose peak wavelength of the photoexcitation emission spectrum of the solid film shown in the present application is between 550 and 630 nm is represented by the following general formula [13].

Formula [13]

(In the formula, Ar ^{11 to} Ar ¹⁴ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group,
R ¹⁵² and R ¹⁵³ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryloxy Represents a carbonyl group. )

In the material represented by the general formula [13], the unsubstituted alkyl group and the unsubstituted aryl group represented by Ar ^{11 to} Ar ¹⁴ are the unsubstituted alkyl group and the unsubstituted alkyl group in the general formulas [1] and [2]. It is synonymous with a substituted aryl group.

In the material represented by the general formula [13], the unsubstituted alkyl group, unsubstituted aryl group, unsubstituted alkoxycarbonyl group, and unsubstituted aryloxycarbonyl group of R ¹⁵² and R ¹⁵³ are: It is synonymous with the unsubstituted alkyl group, the unsubstituted aryl group, the unsubstituted alkoxycarbonyl group, and the unsubstituted aryloxycarbonyl group in the general formulas [1] and [2].

  The alkyl group, aryl group, alkoxycarbonyl group, and aryloxycarbonyl group described above may be substituted with the substituents described in the general formulas [1] and [2].

  Hereinafter, typical examples of the material represented by the general formula [13] that can be used in the present invention are shown in Table 5, but the present invention is not limited to these.

Table 5

  Details of the pyromethene derivative will be described below. Furthermore, as an organic EL device using a compound having a pyromethene skeleton or a metal complex thereof as a dopant, for example, JP 2000-208265 A, JP 2000-208266 A, JP 2000-208267 A, JP 2000-2000 A, and the like. JP-A-208268, JP-A-2000-208269, JP-A-2000-208270, JP-A-2000-208271, JP-A-2000-208272, JP-A-2000-208273, JP-A-3129200 JP-A-2001-223081, JP-A-2001-223082, JP-A-2001-257077, JP-A-2001-297881, JP-A-2001-307484, JP-A-2002-134274, Open 2002-13427 JP are known JP 2003-12676.

  The pyromethene derivative of the material having a peak wavelength of the photoexcitation emission spectrum of the solid film shown in the present application between 550 to 630 nm is represented by the following general formula [14].

General formula [14]

(Wherein, R ¹⁵⁴ to R ¹⁶⁰ represent respectively independently, a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted amino group.)

In the material represented by the general formula [14], the unsubstituted alkyl group, the unsubstituted aryl group, or the substituted amino group represented by R ^{154 to} R ¹⁶⁰ may be the same as those in the general formulas [1] and [2]. It is synonymous with a substituted alkyl group, an unsubstituted aryl group, and a substituted amino group.

  The alkyl group, aryl group, and amino group described above may be substituted with the substituents described in the general formulas [1] and [2].

  Table 6 below shows typical examples of the material represented by the general formula [14] that can be used in the present invention, but the present invention is not limited to these.

Table 6

  Details of the pyran derivative will be described below. Furthermore, as an organic EL device using a compound having a pyran derivative as a dopant, for example, C.I. H. Chen et al., Macromol. Symp. 125, 34-36 and 49-58, published in 1997, tris (8-hydroxyquinolinate) aluminum as a host material and 4H such as DCM, DCJ, DCJT, DCJTB -An organic EL device capable of emitting orange to red light using a pyran derivative as a dopant has been reported. Japanese Laid-Open Patent Publication No. 11-292875 is known as this similar structure.

  A pyran derivative of a material having a peak wavelength of a photoexcitation emission spectrum of a solid film between 550 and 630 nm shown in the present application is represented by the following general formula [15].

General formula [15]

(Wherein R ^{161 to} R ¹⁶⁷ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted silyl group, a cyano group, a nitro group, Group or a substituted amino group,
R ¹⁶⁸ and R ¹⁶⁹ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. R ¹⁶¹ and R ¹⁶² , R ¹⁶⁵ and R ¹⁶⁸ , R ¹⁶⁶ and R ¹⁶⁹ may form a ring with each other.

In the material represented by the general formula [15], the unsubstituted alkyl group, unsubstituted aryl group, unsubstituted alkoxyl group, substituted silyl group, and substituted amino group of R ^{161 to} R ¹⁶⁷ It is synonymous with the unsubstituted alkyl group, the unsubstituted aryl group, the unsubstituted alkoxyl group, the substituted silyl group, and the substituted amino group in the formulas [1] and [2].

In the material represented by the general formula [15], the unsubstituted alkyl group and the unsubstituted aryl group represented by R ¹⁶⁸ and R ¹⁶⁹ are the same as the unsubstituted alkyl group in the general formulas [1] and [2]. It is synonymous with a substituted aryl group.

  The alkyl group, aryl group, alkoxyl group, aryloxy group, thioalkoxyl group, silyl group, or amino group described above is substituted with the substituent described in the general formulas [1] and [2]. Also good. These substituents may be bonded to each other to form a ring.

  Table 7 shows typical examples of the material represented by the general formula [15] that can be used in the present invention, but the present invention is not limited to these.

Table 7

  Details of the naphthacene derivative will be described below. Moreover, as an organic EL device using a compound having a naphthacene derivative as a dopant, for example, JP 2002-97465 PR, JP 2002-167578 PR, and JP 2002-167579 PR are known.

  The naphthacene derivative of the material having a peak wavelength of the photoexcitation emission spectrum of the solid film shown in the present application between 550 to 630 nm is represented by the following general formula [16].

Formula [16]

(Wherein Ar ^{15 to} Ar ¹⁸ each independently represents a hydrogen atom, a substituted or unsubstituted aryl group,
R ^{170 to} R ¹⁷⁷ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted silyl group, a cyano group, a nitro group, or Represents a substituted amino group. )

In the material represented by the general formula [16], the unsubstituted aryl group of Ar ^{15 to} Ar ^{18 has} the same meaning as the unsubstituted aryl group in the general formulas [1] and [2].

In the material represented by the general formula [16], the unsubstituted alkyl group, the unsubstituted aryl group, the unsubstituted alkoxyl group, the substituted silyl group, and the substituted amino group represented by R ^{170 to} R ¹⁷⁷ It is synonymous with the unsubstituted alkyl group, the unsubstituted aryl group, the unsubstituted alkoxyl group, the substituted silyl group, and the substituted amino group in the formulas [1] and [2].

  Hereinafter, typical examples of the material represented by the general formula [16] that can be used in the present invention are shown in Table 8, but the present invention is not limited to these.

Table 8

  Hereinafter, the styryl derivative will be described in detail. Moreover, as an organic EL device using a compound having a styryl derivative as a dopant, for example, JP-A 05-121168, JP-A 06-9953, JP-A 06-100857, JP-A 06-207170 , WO2003-037836, JP 2009-4761, etc. are known.

  The styryl derivative of the material having a peak wavelength of the photoexcitation emission spectrum of the solid film shown in the present application between 550 to 630 nm is represented by the following general formula [17].

General formula [17]

(Wherein Ar ^{20 to} Ar ²² each independently represents a hydrogen atom, a substituted or unsubstituted aryl group,
Ar ²³ represents a divalent linking group. )

In the material represented by the general formula [17], the unsubstituted aryl group of Ar ^{20 to} Ar ^{22 has} the same meaning as the unsubstituted aryl group in the general formulas [1] and [2].

  The aryl group described above may be further substituted with a substituent described in the general formula [1]. These substituents may be bonded to each other to form a ring. Moreover, there exists a cyano group as a substituent which may be substituted by an aryl group.

In the material represented by the general formula [17], Ar ²³ represents a divalent linking group, and specific examples thereof include a phenylene group and a naphthylene group.

  Table 9 below shows typical examples of the material represented by the general formula [17] that can be used in the present invention, but the present invention is not limited to these.

Table 9

  Details of the iridium complex and platinum complex will be described below. In addition, as an organic EL device using a compound having an iridium complex or a platinum complex as a dopant, it emits light from a triplet excited state in which efficiency is significantly improved as compared with a conventional organic EL device using a singlet excited state. Use Nature 395, 151 pages, 1998, Applied Physics Letters, 75 pages, 4 pages, 1999, J. Am. Chem. Soc. 123, 4304, 2001, etc., and attracts attention. As a specific material, Japanese Patent Application Laid-Open No. 2010-161071 is known.

  The iridium complex of the material whose peak wavelength of the photoexcitation emission spectrum of the solid film shown in this application is between 550 and 630 nm is represented by the following general formula [18].

General formula [18]

(Wherein R ^{180 to} R ¹⁸⁹ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and R ^{180 to} R ¹⁸³ and R ^{184 to} R ¹⁸⁷ are respectively Adjacent substituents may form a ring, and n and m each represents an integer of 0 to 3, and the sum of n and m is 3.)

Further, in the material represented by the general formula [18], an unsubstituted alkyl group represented by R ^{180 to} R ¹⁸⁹ , an unsubstituted aryl group, an unsubstituted alkyl group represented by the general formulas [1] and [2], unsubstituted It is synonymous with the aryl group.

  The alkyl group and aryl group described above may be further substituted with a substituent described in the general formula [1]. These substituents may be bonded to each other to form a ring.

  Table 10 below shows typical examples of materials represented by the general formula [18] and platinum complexes that can be used in the present invention, but the present invention is not limited to these.

Table 10

  By the way, the organic EL element is composed of an element in which a single layer or a multilayer organic layer is formed between an anode and a cathode. Here, the single layer type organic EL element is composed only of a light emitting layer between an anode and a cathode. The element which becomes. On the other hand, the multilayer organic EL element facilitates injection of holes and electrons into the light emitting layer in addition to the light emitting layer, and facilitates recombination of holes and electrons in the light emitting layer. For the purpose of this, it refers to a layer in which a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and the like are laminated. Therefore, typical element configurations of the multilayer organic EL element include (1) anode / hole injection layer / light emitting layer / cathode, and (2) anode / hole injection layer / hole transport layer / light emitting layer / cathode. (3) Anode / hole injection layer / light emitting layer / electron injection layer / cathode, (4) Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode, (5) Anode / positive Hole injection layer / light emitting layer / hole blocking layer / electron injection layer / cathode, (6) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron injection layer / cathode, (7) An element structure in which a multilayer structure of anode / light emitting layer / hole blocking layer / electron injection layer / cathode, (8) anode / light emitting layer / electron injection layer / cathode, etc., is considered.

  Moreover, each organic layer mentioned above may be formed by the layer structure of two or more layers, respectively, and several layers may be laminated | stacked repeatedly. As such an example, an element configuration called “multi-photon emission” in which a part of the above-described multilayer organic EL element is multilayered has been proposed in recent years for the purpose of improving light extraction efficiency. For example, in an organic EL device composed of a glass substrate / anode / hole transport layer / electron transporting light emitting layer / electron injection layer / charge generating layer / light emitting unit / cathode, the charge generating layer and the light emitting unit A method of laminating a plurality of layers is an example.

For the hole injection layer, a hole injection material that exhibits an excellent hole injection effect with respect to the light emitting layer and that can form a hole injection layer excellent in adhesion to the anode interface and thin film formability is used. In addition, when such materials are laminated in multiple layers and a material having a high hole injection effect and a material having a high hole transport effect are laminated, the materials used for each are called a hole injection material and a hole transport material. Sometimes. The organic electroluminescent element material of the present invention can be suitably used for both hole injection materials and hole transport materials. These hole injection materials and hole transport materials need to have a high hole mobility and a small ionization energy of usually 5.5 eV or less. Such a hole injection layer is preferably a material that transports holes to the light emitting layer with a lower electric field strength, and further has a hole mobility of at least when an electric field of 10 ⁴ to 10 ⁶ V / cm is applied. What is 10 ^<-6 > cm ^{< 2} > / V * second is preferable. Other hole injection materials and hole transport materials that can be used by mixing with the organic electroluminescence device material of the present invention are not particularly limited as long as they have the above-mentioned preferable properties. An arbitrary material can be selected and used from those commonly used as a charge transport material for holes in an optical transmission material and known materials used for a hole injection layer of an organic EL element.

  Specific examples of such hole injection materials and hole transport materials include triazole derivatives (see US Pat. No. 3,112,197) and oxadiazole derivatives (US Pat. No. 3,189). , 447, etc.), imidazole derivatives (see Japanese Patent Publication No. 37-16096), polyarylalkane derivatives (US Pat. Nos. 3,615,402 and 3,820,989). No. 3,542,544, JP-B-45-555, JP-A-51-10983, JP-A-51-93224, JP-A-55-17105, JP-A-56-4148 55-108667, 55-156953, 56-36656, etc.), pyrazoline derivatives and pyrazolone derivatives (US Pat. No. 3,180, No. 29, No. 4,278,746, JP-A 55-88064, No. 55-88065, No. 49-105537, No. 55-51086, No. 56-80051. No. 56-88141, No. 57-45545, No. 54-112437, No. 55-74546, etc.), phenylenediamine derivatives (US Pat. No. 3,615,404, Japanese Patent Publication Nos. 51-10105, 46-3712, 47-25336, JP 54-53435, 54-110536, 54-1119925, etc.), Ali- Ruamine derivatives (US Pat. Nos. 3,567,450, 3,180,703, 3,240,597, No. 658,520, No. 4,232,103, No. 4,175,961, No. 4,012,376, JP-B 49-35702, No. 39 -27577, JP-A-55-144250, JP-A-56-119132, JP-A-56-22437, West German Patent No. 1,110,518, etc.), amino-substituted chalcone derivatives (US patents) No. 3,526,501 etc.), oxazole derivatives (disclosed in US Pat. No. 3,257,203 etc.), styryl anthracene derivatives (see JP 56-46234 A, etc.) ), Fluorenone derivatives (see JP-A-54-110837, etc.), hydrazone derivatives (US Pat. No. 3,717,462, JP-A-54-59143, 55-52063, 55-52064, 55-46760, 55-85495, 57-11350, 57-148749, JP-A-2-311591, etc. Stilbene derivatives (Japanese Patent Laid-Open Nos. 61-210363, 61-228451, 61-14642, 61-72255, 62-47646, 62-36674) 62-10652, 62-30255, 60-93455, 60-94462, 60-174749, 60-175052, etc.), silazane derivatives (US) Patent No. 4,950,950), polysilane (JP-A-2-204996), aniline copolymer (JP-A-2-282263), a conductive polymer disclosed in Japanese Patent Laid-Open No. 1-211399 oligomer - (particularly thiophene oligomer -) and the like.

As the hole injecting material and the hole transporting material, those described above can be used. Porphyrin compounds (Japanese Patent Laid-Open No. 63-295965), aromatic tertiary amine compounds and styrylamine compounds (US Pat. No. 4,127,412, JP-A-53-27033, 54-58445, 54-149634, 54-64299, 55-79450, 55-144250 No. 56-119132, No. 61-295558, No. 61-98353, No. 63-295695, etc.) can also be used. For example, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl having two condensed aromatic rings in the molecule described in US Pat. No. 5,061,569, etc. And 4,4 ′, 4 ″ -tris (N- (3-methylphenyl)-, in which three triphenylamine units described in JP-A-4-308688 are linked in a starburst type. N-phenylamino) triphenylamine, etc. In addition, examples of the hole injection material include phthalocyanine derivatives such as copper phthalocyanine and hydrogen phthalocyanine, and other aromatic dimethylidene compounds, p-type Si, p Inorganic compounds such as type SiC can also be used as the material for the hole injection material and the hole transport material.

  Specific examples of the aromatic tertiary amine derivative include, for example, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N, N , N ′, N ′-(4-methylphenyl) -1,1′-phenyl-4,4′-diamine, N, N, N ′, N ′-(4-methylphenyl) -1,1′- Biphenyl-4,4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N ′-(methylphenyl) -N, N '-(4-N-butylphenyl) -phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane, N, N'-bis (4 '-Diphenylamino-4-biphenylyl) -N, N'-diphenyl Nzine, N, N′-bis (4′-diphenylamino-4-phenyl) -N, N′-diphenylbenzidine, N, N′-bis (4′-diphenylamino-4-phenyl) -N, N ′ -Di (1-naphthyl) benzidine, N, N'-bis (4'-phenyl (1-naphthyl) amino-4-phenyl) -N, N'-diphenylbenzidine, N, N'-bis (4'- Phenyl (1-naphthyl) amino-4-phenyl) -N, N′-di (1-naphthyl) benzidine and the like can be mentioned, and these can be used for both hole injection materials and hole transport materials.

  Table 11 shows examples particularly preferable as the hole injection material.

Table 11

  Moreover, as a hole transport material which can be used with the compound (organic EL element material) of this invention, the well-known compound shown in following Table 12 is mention | raise | lifted.

Table 12

  In order to form this hole injection layer, the above compound is thinned by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. Although there is no restriction | limiting in particular, Usually, they are 5 nm-5 micrometers.

On the other hand, for the electron injection layer, an electron injection material that exhibits an excellent electron injection effect with respect to the light emitting layer and that can form an electron injection layer excellent in adhesion to the cathode interface and thin film formability is used. Examples of such electron injection materials include metal complex compounds, nitrogen-containing five-membered ring derivatives, fluorenone derivatives, anthraquinodimethane derivatives, diphenoquinone derivatives, thiopyrandioxide derivatives, perylenetetracarboxylic acid derivatives, fluorenylidenemethane. Derivatives, anthrone derivatives, silole derivatives, triarylphosphine oxide derivatives, calcium acetylacetonate, sodium acetate and the like. In addition, inorganic / organic composite materials doped with metal such as cesium in bathophenanthroline (Proceedings of the Society of Polymer Science, Vol. 50, No. 4, 660, published in 2001) and the 50th Association of Applied Physics Lecture Proceedings, No. Examples of electron injection materials include BCP, TPP, T5MPyTZ, etc. published on page 3, 1402, 2003. Electrons can be transported by forming a thin film necessary for device fabrication and injecting electrons from the cathode. If it is material, it will not specifically limit to these.

  Among the electron injection materials, particularly effective electron injection materials include metal complex compounds, nitrogen-containing five-membered ring derivatives, silole derivatives, and triarylphosphine oxide derivatives. As a preferable metal complex compound that can be used in the present invention, a metal complex of 8-hydroxyquinoline or a derivative thereof is suitable. Specific examples of the metal complex of 8-hydroxyquinoline or its derivatives include tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (4-methyl- 8-hydroxyquinolinato) aluminum, tris (5-methyl-8-hydroxyquinolinato) aluminum, tris (5-phenyl-8-hydroxyquinolinato) aluminum, bis (8-hydroxyquinolinato) G) (1-naphtholato) aluminum, bis (8-hydroxyquinolinato) (2-naphtholato) aluminum, bis (8-hydroxyquinolinato) (phenolate) aluminum, bis (8 -Hydroxyquinolinato) (4-cyano-1-naphtholato) aluminum, bis (4-methyl-8) Hydroxyquinolinato) (1-naphtholato) aluminum, bis (5-methyl-8-hydroxyquinolinato) (2-naphtholato) aluminum, bis (5-phenyl-8-hydroxyquinolina) G) (phenolate) aluminum, bis (5-cyano-8-hydroxyquinolinato) (4-cyano-1-naphtholato) aluminum, bis (8-hydroxyquinolinato) chloroaluminum, bis Aluminum complex compounds such as (8-hydroxyquinolinato) (o-cresolato) aluminum, tris (8-hydroxyquinolinato) gallium, tris (2-methyl-8-hydroxyquinolinato) gallium , Tris (4-methyl-8-hydroxyquinolinato) gallium, tris (5-methyl-8-hydroxyquinolinato) Gallium, tris (2-methyl-5-phenyl-8-hydroxyquinolinato) gallium, bis (2-methyl-8-hydroxyquinolinato) (1-naphtholato) gallium, bis (2-methyl) -8-hydroxyquinolinato) (2-naphtholato) gallium, bis (2-methyl-8-hydroxyquinolinato) (phenolate) gallium, bis (2-methyl-8-hydroxyquinolina) -To) (4-cyano-1-naphtholato) gallium, bis (2,4-dimethyl-8-hydroxyquinolinato) (1-naphtholato) gallium, bis (2,5-dimethyl-8) -Hydroxyquinolinato) (2-naphtholato) gallium, bis (2-methyl-5-phenyl-8-hydroxyquinolinato) (phenolate) gallium, bis (2-methyl-5- Cyano-8-hydroxyquinolinato) (4-cyano-1-naphtholato) gallium, bis (2-methyl-8-hydroxyquinolinato) chlorogallium, bis (2-methyl-8-hydroxyquino) In addition to gallium complex compounds such as linato) (o-cresolato) gallium, 8-hydroxyquinolinatolithium, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) Metal complex compounds such as manganese, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (8-hydroxyquinolinato) zinc, bis (10-hydroxybenzo [h] quinolinato) zinc It is done.

Among the electron injection materials that can be used in the present invention, preferred nitrogen-containing five-membered ring derivatives include oxazole derivatives, thiazol derivatives, oxadiazol derivatives, thiadiazol derivatives, and triazole derivatives. Specifically, 2,5-bis (1-phenyl) -1,3,4-oxazole, 2,5-bis (1-phenyl) -1,3,4-thiazol, 2 , 5-bis (1-phenyl) -1,3,4-oxadiazol, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) 1,3,4-oxadiazol, 2,5-bis (1-naphthyl) -1,3,4-oxadiazol, 1,4-bis [2- (5-phenyloxadiazolyl)) benzene, 1,4-bis [2- (5 -Phenyloxadiazolyl) -4-tert-butylben ], 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-thiadiazol, 2,5-bis (1-naphthyl) -1,3,4 -Thiadiazol, 1,4-bis [2- (5-phenylthiadiazolyl). ) Benzene, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-triazole, 2,5-bis (1-naphthyl) -1,3,4 -Triazol, 1,4-bis [2- (5-phenyltriazolyl)] benzene and the like.

  As the nitrogen-containing aromatic heterocyclic group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 3-pyridyl group, 4-pyridazyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, Monovalent nitrogen-containing monocyclic aromatic heterocyclic groups such as 2-pyrazyl group and 1-imidazolyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7 -Quinolyl group, 8-quinolyl group, 2-quinazolyl group, 4-quinazolyl group, 5-quinazolyl group, 2-quinoxalyl group, 5-quinoxalyl group, 6-quinoxalyl group, 1-indolyl group, 9-caribazolyl group, etc. Monovalent nitrogen-containing fused ring aromatic heterocyclic group, 2,2′-bipyridyl-3-yl group, 2,2′-bipyridyl-4-yl group, 3,3′-bipyridyl-2-yl group, 3 , 3′-bipyridyl-4- Group, 4,4'-bipyridyl-2-yl group, a monovalent nitrogen-containing ring set aromatic heterocyclic group such as 4,4'-bipyridyl-3-yl group.

  Table 13 shows specific examples of oxadiazole derivatives.

Table 13

  Table 14 shows specific examples of triazole derivatives.

Table 14

  Table 15 shows specific examples of silole derivatives.

Table 15

  Furthermore, a hole blocking material that can prevent holes from passing through the light emitting layer from reaching the electron injection layer and form a layer having excellent thin film formability is used for the hole blocking layer. Examples of such hole blocking materials include aluminum complex compounds such as bis (8-hydroxyquinolinato) (4-phenylphenolato) aluminum, and bis (2-methyl-8-hydroxyquinolina). -To) (4-phenylphenolato) gallium complex compounds such as gallium, and nitrogen-containing condensed aromatic compounds such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP). .

  Moreover, when using the light emitting material of this invention for a light emitting layer, you may contain other materials as a host material and a dopant. In this case, the concentration of the dopant with respect to the light emitting material of the present invention is preferably contained in the range of 0.001 to 30% by weight with respect to the light emitting material of the present invention, and in the range of 0.01 to 10% by weight. More preferably, it is contained in the range of 0.1 to 5% by weight.

Furthermore, the material used for the anode of the organic EL device of the present invention is preferably a material having a work function (4 eV or more) metal, alloy, electrically conductive compound or a mixture thereof as an electrode substance. Specific examples of such an electrode substance include metals such as Au, and conductive materials such as CuI, ITO, SNO ₂ and ZnO. In order to form this anode, a thin film can be formed from these electrode materials by a method such as vapor deposition or sputtering. The anode desirably has such a characteristic that when light emitted from the light emitting layer is extracted from the anode, the transmittance of the anode for light emission is greater than 10%. The sheet resistance of the anode is preferably several hundred Ω / □ or less. Further, although the film thickness of the anode depends on the material, it is usually selected in the range of 10 nm to 1 μm, preferably 10 to 200 nm.

  The material used for the cathode of the organic EL device of the present invention is a material having a small work function (4 eV or less) metal, alloy, electrically conductive compound and a mixture thereof as an electrode substance. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / silver alloy, aluminum / aluminum oxide, aluminum / lithium alloy, indium, and rare earth metals. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. Here, when light emitted from the light-emitting layer is extracted from the cathode, the transmittance of the cathode for light emission is preferably greater than 10%. The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually 10 nm to 1 μm, preferably 50 to 200 Nm.

  Regarding the method for producing the organic EL device of the present invention, an anode, a light emitting layer, a hole injection layer as necessary, and an electron injection layer as necessary are formed by the above materials and methods, and finally a cathode is formed. do it. Moreover, an organic EL element can also be produced from the cathode to the anode in the reverse order.

  This organic EL element is manufactured on a translucent substrate. This translucent substrate is a substrate that supports the organic EL element, and for the translucency, it is desirable that the transmittance of light in the visible region of 400 to 700 nm is 50% or more, preferably 90% or more, Further, it is preferable to use a smooth substrate.

  These substrates have mechanical and thermal strengths and are not particularly limited as long as they are transparent. For example, glass plates, synthetic resin plates and the like are preferably used. Examples of the glass plate include plates made of soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz, and the like. Examples of the synthetic resin plate include polycarbonate resin, acrylic resin, polyethylene terephthalate resin, polyethersulfide resin, and polysulfone resin.

As a method for forming each layer of the organic EL device of the present invention, a dry film forming method such as vacuum deposition, electron beam irradiation, sputtering, plasma, ion plating, or spin coating, dipping, flow coating, etc. , A wet film forming method such as an ink jet method, a method of depositing a light emitter on a donor film, and Japanese Patent Application Laid-Open No. 2002-534782 and S.A. T. T. et al. Lee, et al. Proceedings of SID'02, p. LITI (Laser Induced Thermal Imaging) method described in 784 (2002), printing (offset printing, flexographic printing, gravure printing, screen printing), inkjet, and the like can also be applied.
The organic layer is particularly preferably a molecular deposited film. Here, the molecular deposited film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidifying from a material compound in a solution state or a liquid phase state. Can be classified from a thin film (accumulated film) formed by the LB method according to a difference in an agglomerated structure and a higher-order structure and a functional difference resulting therefrom. Also, as disclosed in JP-A-57-51781, a binder such as a resin and a material compound are dissolved in a solvent to form a solution, and then this is thinned by a spin coat method or the like. Also, an organic layer can be formed. The film thickness of each layer is not particularly limited, but if the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. Conversely, if the film thickness is too thin, the pinhole is Or the like, and even when an electric field is applied, it is difficult to obtain sufficient light emission luminance. Accordingly, the thickness of each layer is suitably in the range of 1 nm to 1 μm, but more preferably in the range of 10 nm to 0.2 μm.

  Further, in order to improve the stability of the organic EL element with respect to temperature, humidity, atmosphere and the like, a protective layer may be provided on the surface of the element, or the entire element may be covered or sealed with a resin or the like. In particular, when the entire element is covered or sealed, a photocurable resin that is cured by light is preferably used.

  The current applied to the organic EL element of the present invention is usually a direct current, but a pulse current or an alternating current may be used. The current value and the voltage value are not particularly limited as long as the element is within a range not destroying the element. However, considering the power consumption and life of the element, it is desirable to efficiently emit light with as little electrical energy as possible.

  The organic EL device driving method of the present invention can be driven not only by the passive matrix method but also by the active matrix method. Further, the method for extracting light from the organic EL device of the present invention is applicable not only to the method of bottom emission for extracting light from the anode side but also to the method of top emission for extracting light from the cathode side. These methods and techniques are described in Shinji Kido, “All about organic EL”, published by Nihon Jitsugyo Shuppansha (published in 2003).

  The main methods of the full color method of the organic EL element of the present invention include a three-color coating method, a color conversion method, and a color filter method. In the three-color coating method, there are a vapor deposition method using a shadow mask, an ink jet method and a printing method. In addition, Special Tables 2002-534882 and S.A. T.A. Lee, et al. , Proceedings of SID'02, p. 784 (2002) can also be used. The laser thermal transfer method (also referred to as Laser Induced Thermal Imaging, LITI method) can also be used. In the color conversion method, a blue light emitting layer is used to convert green and red having a longer wavelength than blue through a color conversion (CCM) layer in which fluorescent dyes are dispersed. The color filter method uses a white light emitting organic EL element to extract light of three primary colors through a color filter for liquid crystal. In addition to these three primary colors, a part of white light is directly extracted and used for light emission. Thus, the luminous efficiency of the entire device can be increased.

Furthermore, the organic EL element of the present invention may adopt a microcavity structure. This is because the organic EL element has a structure in which the light emitting layer is sandwiched between the anode and the cathode, and the emitted light causes multiple interference between the anode and the cathode, but the reflectance and transmission of the anode and the cathode. This is a technology that actively uses the multiple interference effect and controls the emission wavelength extracted from the device by appropriately selecting the optical characteristics such as the rate and the film thickness of the organic layer sandwiched between them. . Thereby, it is also possible to improve the emission chromaticity. For the mechanism of this multiple interference effect, see J.A. Yamada et al., AM-LCD Digest of Technical Papers, OD-2, p. 77-80 (2002).
As described above, the organic EL element can obtain deep red light emission exhibiting high color purity and luminance at a low driving voltage. Therefore, this organic EL device can be applied to flat panel displays such as wall-mounted televisions and flat light emitters, as well as light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights. Can be considered.

  EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to the following Example.

  Method for synthesizing organic EL device material of the present invention

The synthesis method of 1,4-diketopyrrolo (3,4-c) pyrrole is described in Journal of
The method described in Coatings Technology, 60, 37 (1988) was referred to.

  The synthesis method of 1,4-diketopyrrolo (3,4-c) pyrrole substituted with N-alkyl was referred to the method described in JP-A-7-188234.

  First, synthesis examples of the present invention will be described, but the present invention is not limited to these synthesis examples.

Synthesis example 2
Synthesis Method of Organic EL Device Material (2) Compound (2) was synthesized according to Reaction Formula 1 to Reaction Formula 4.

Reaction formula 1

Hereinafter, the synthesis method will be described with reference to Reaction Scheme 1.
Under a nitrogen atmosphere, 9.6 g (0.24 mol) of sodium hydride (60%) and 25 g (0.25 mol) of 2-cyanothiophene are added at room temperature in 200 ml of tert-pentyl alcohol with stirring. Thereafter, the temperature was raised to 100 ° C., and 16 g (0.08 mol) of diisopropyl succinate was added dropwise at this temperature. During the addition, the temperature of the reaction product was maintained at 100 ° C. After completion of the dropwise addition, stirring was performed for 3 hours at the same temperature while removing by-produced isopropyl alcohol out of the system. Thereafter, the mixture was cooled to 60 ° C., and at this temperature, a mixed solution of 21 g of acetic acid and 300 g of methanol was added dropwise. It was then filtered, washed with methanol and dried at 60 ° C. Further, the mixture was heated in methanol at 60 ° C. for 30 minutes, filtered while hot, and washed with methanol. 19g of (III) was obtained as dark red powder by drying at 60 degreeC.

Reaction formula 2

Hereinafter, the synthesis method will be described with reference to Reaction Scheme 2.
Under a nitrogen atmosphere, the compound (9 g) represented by (III) obtained by the above method is suspended in 230 g of dimethylacetamide and heated to 50 ° C. with stirring. At this temperature, 8.64 g of sodium tert-butoxy are added and stirred at 50 ° C. for 30 minutes. Next, 25 g of 1-bromo-2-ethylhexane is added dropwise, and after completion of the addition, stirring is performed at 50 ° C. for 2 hours. When the reaction solution is cooled to room temperature and gradually poured into a mixed solution of 1000 g of water and 800 g of methanol, a dark red solid precipitates and becomes suspended. The mixture was stirred at room temperature for 1 hour, filtered, washed with water, washed with methanol and dried to obtain 13.5 g of (V) as a dark red powder.

Reaction formula 3

Hereinafter, the synthesis method will be described with reference to Reaction Scheme 3.
Under a nitrogen atmosphere, the compound (5 g) represented by (V) obtained by the above method is suspended in 100 g of chloroform and cooled to 0 ° C. with stirring. At this temperature, 3.74 g of N-bromosuccinimide (NBS) is added, and the mixture is returned to room temperature and stirred for 12 hours. When the reaction solution is cooled to room temperature and gradually poured into a mixed solution of 1000 g of water and 800 g of methanol, a dark red-purple solid is precipitated and becomes a suspended state. The mixture was stirred at room temperature for 1 hour, filtered, washed with water, washed with methanol, and dried to obtain 3.5 g of (VI) as a dark red-purple powder.

Reaction formula 4

Hereinafter, the synthesis method will be described with reference to Reaction Scheme 4.
1.6 g (2.4 mmol) of the compound represented by (VI) 2 obtained by the above method under a nitrogen atmosphere, 1.014 g (5.7 mmol) of benzo [b] thiophen-2-ylboronic acid, 10 ml of ethanol, Tetrakis (triphenylphosphine) palladium (0.1 g), potassium carbonate (2M aqueous solution) (10 g), and ethylene glycol dimethyl ether (30 g) were added to a four-necked flask and heated to reflux for 6 hours. Thereafter, the reaction solution was poured into 400 ml of methanol, and the precipitated solid was collected by filtration and dried in a heat vacuum to obtain 0.57 g of compound (2) as a blue powder. The obtained crude product was further purified by silica gel column chromatography. Compound (2) was identified by mass spectrum (manufactured by Bruker Daltonics, Autoflex II), ¹ H-NMR, and ¹³ C-NMR (manufactured by JEOL, ECX-400P).

  A commercially available reagent was used for benzo [b] thiophen-2-ylboronic acid used for the synthesis of compound (3).

Synthesis Examples 1 and 3-56
The compounds in Table 1 were synthesized by combining the following reaction formulas 5 to 13.

Reaction formula 5

In Reaction Scheme 5, R ^{3 to} R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryl group, Represents a ruoxy group, a substituted or unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, a substituted silyl group, or a substituted amino group; However, any of R ^{3 to} R ⁸ represents a substituent represented by the general formula [3] or the general formula [4].

Reaction formula 6

In Reaction Scheme 6, R ¹ and R ² are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryl group. Represents a ruoxycarbonyl group,
R ^{3 to} R ⁸ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, substituted or unsubstituted It represents an unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, a substituted silyl group, or a substituted amino group. However, any of R ^{3 to} R ⁸ represents a substituent represented by the general formula [3] or the general formula [4].

Reaction formula 7

In Reaction Scheme 7, R ¹ and R ² are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryl group. Represents a ruoxycarbonyl group,
R ^{4 to} R ⁵ and R ^{7 to} R ⁸ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryl group. -Represents a ruoxy group, a substituted or unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, a substituted silyl group, or a substituted amino group. However, any of R ^{4 to} R ⁵ and R ^{7 to} R ⁸ represents a substituent represented by the general formula [3] or the general formula [4].

Reaction formula 8

In Reaction Scheme 8, R ¹ and R ² are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryl group. Represents a ruoxycarbonyl group,
R ^{3 to} R ⁸ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, substituted or unsubstituted It represents an unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, a substituted silyl group, or a substituted amino group. However, any of R ^{3 to} R ⁸ represents a substituent represented by the general formula [3] or the general formula [4].

Reaction formula 9

In Reaction Scheme 9, R ^{11 to} R ¹⁶ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryl group. Represents a ruoxy group, a substituted or unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, a substituted silyl group, or a substituted amino group; However, any of R ^{11 to} R ¹⁶ represents a substituent represented by the general formula [3] or the general formula [4].

Reaction formula 10

In Reaction Scheme 10, R ⁹ and R ¹⁰ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryl group. Represents a ruoxycarbonyl group,
R ^{11 to} R ¹⁶ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, substituted or unsubstituted It represents an unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, a substituted silyl group, or a substituted amino group. However, any of R ^{11 to} R ¹⁶ represents a substituent represented by the general formula [3] or the general formula [4].

Reaction formula 11

In Reaction Scheme 11, R ⁹ and R ¹⁰ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryl group. Represents a ruoxycarbonyl group,
R ¹¹ and R ¹³ are each independently R ¹⁴ and R ¹⁶ are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted group An aryloxy group, a substituted or unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, a substituted silyl group, or a substituted amino group is represented. However, R ¹¹ and R ^13, any of R ¹⁴ and R ^16, represents a substituent represented by the general formula [3] or the general formula [4].

Reaction formula 12

In Reaction Scheme 12, R ⁹ and R ¹⁰ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryl group. Represents a ruoxycarbonyl group,
R ^{11 to} R ¹⁶ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, substituted or unsubstituted It represents an unsubstituted thioalkoxyl group, a substituted or unsubstituted thioaryloxy group, a substituted silyl group, or a substituted amino group. However, any of R ^{11 to} R ¹⁶ represents a substituent represented by the general formula [3] or the general formula [4].

The structure of the compound of the present invention obtained by combining the above reaction formulas (5) to (12) was identified by mass spectrum, ¹ H-NMR, and ¹³ C-NMR as in Synthesis Example 1. The measurement results of the mass spectrum of the synthesized compound are shown in Table 16. The compound numbers are the same as those described in Table 1 in this specification.

Table 16

Confirmation of peak wavelength of photoexcitation emission spectrum of solid film.
Example 1
The compound H-1 shown in Table 2 was vacuum-deposited with a thickness of 30 nm on the washed quartz glass substrate. The vacuum deposition method was performed in a vacuum of 10 ⁻⁶ Torr and without temperature control such as substrate heating and cooling. With respect to the obtained quartz substrate with a deposited film, the spectrum of light emission by photoexcitation was measured. As a result of discriminating whether the peak wavelength of the obtained emission spectrum was in the range of 550 to 630 nm, it was confirmed to be within the range.

Examples 2-108
A quartz substrate with a deposited film was prepared in the same manner as in Example 1 except that the compound shown in Table 9 was used instead of the compound H-1 in Table 2, and the spectrum of light emission by photoexcitation was measured. Table 17 shows the result of determining whether the peak wavelength of the obtained light emission is in the range of 550 to 630 nm.

Comparative Examples 1-2
A quartz substrate with a deposited film was prepared in the same manner as in Example 1 except that the following compounds (A) to (B) were used in place of the compound H-1 in Table 2, and the emission spectrum by photoexcitation was measured. Table 17 shows the result of determining whether the peak wavelength of the obtained light emission is in the range of 550 to 630 nm.

Table 17

Examples of Organic EL Device The present invention will be specifically described below with reference to examples, but the present invention is not limited to the following examples. In the examples, all mixing ratios are weight ratios unless otherwise specified. The vacuum deposition method was performed in a vacuum of 10 ⁻⁶ Torr and without temperature control such as substrate heating and cooling. In the evaluation of the light emission characteristics of the element, the characteristics of an organic EL element having an electrode area of 2 mm × 2 mm were measured.
The external quantum efficiency η _exp was measured by the following method as the luminous efficiency of the prepared organic EL device. A predetermined voltage was applied using a DC power source, and the amount of current flowing through the device immediately after the application and the spectral radiance were measured. The spectral radiance was measured using a spectral radiance meter CS-1000 manufactured by Minolta. The luminous efficiency η _exp was calculated by measuring the spectral radiance spectrum with the above-mentioned spectral radiance meter and calculating the external quantum efficiency η _exp (unit:%) on the assumption that Lambtian emission was performed from the obtained spectral radiance spectrum. The external quantum efficiency is measured by energizing the organic EL element at a current density of 12.5 mA / cm ² . In addition, as a stability test during repeated use, the time required for the luminance to be halved from the initial value when driven continuously under a constant current at an initial luminance of 1000 cd / m ^{2 in} an environment of 40 ° C. Was evaluated as the luminance half-life of the organic EL device. Moreover, the luminescent color of the element was implemented with said spectral radiance meter.

Example 109
On the washed glass plate with an ITO electrode, α-NPD was vacuum-deposited to obtain a 50 nm-thick hole transport layer. Subsequently, the compound (1) of Table 1 and the compound H-1 of Table 2 were vacuum-deposited by weight ratio of 3:97, and the light emitting layer with a film thickness of 40 nm was obtained. Next, tris (8-hydroxyquinolinato) aluminum (Alq ₃ ) was deposited to obtain an electron injection layer having a thickness of 30 nm. Further thereon, 1 nm of LiF was vapor-deposited, and then Al was vapor-deposited to form an electrode having a thickness of 150 nm to obtain an organic EL device. When an energization test was performed on this device, deep red EL light emission with high color purity was obtained, and the x value in CIE 1931 chromaticity coordinates was 0.67. The external quantum efficiency of this device was 4.4%, and the luminance half life was 500 hours or more. .

Example 110 to Example 204
An organic EL device was produced in the same manner as in Example 109 except that the compound shown in Table 18 was used instead of the compound (2) in Table 1 and the compound H-1 in Table 2. Table 18 shows the external quantum efficiency and luminance half-life of these devices. Further, all of the x values in the CIE1931 chromaticity coordinates of these elements were 0.65 or more.

Comparative Example 3
An organic EL device was produced in the same manner as in Example 109 except that the following compound (C) was used instead of the compound (2) in Table 1. This device emitted orange light, and the x value in CIE1931 chromaticity coordinates was less than 0.62. Table 18 shows the external quantum efficiency and luminance half-life of this device.

Comparative Example 4
An organic EL device was produced in the same manner as in Example 109 except that the compound (A) was used instead of the compound H-1 in Table 2. This element emitted yellow light, and the x value in CIE1931 chromaticity coordinates was less than 0.62. Table 18 shows the external quantum efficiency and luminance half-life of this device.

Comparative Example 5
An organic EL device was produced in the same manner as in Example 109 except that the compound (B) was used instead of the compound H-1 in Table 2. This device showed light blue emission, and the x value in CIE 1931 chromaticity coordinates was less than 0.62. Table 18 shows the external quantum efficiency and luminance half-life of this device.

Table 18

Example 205
On the washed glass plate with an ITO electrode, the compound HTM-4 of Table 12 was vacuum-deposited to obtain a hole transport layer having a thickness of 40 nm. Subsequently, the compound (2) of Table 1, the compound H-25 of Table 4, and the compound H-1 of Table 2 were vacuum-deposited by weight ratio of 3: 7: 90, and the light emitting layer with a film thickness of 40 nm was obtained. It was. Subsequently, compound ES-1 of Table 15 was vapor-deposited and the 30-nm-thick electron injection layer was obtained. Furthermore, after depositing 0.5 nm of LiF on it, Al was vapor-deposited to form an electrode having a thickness of 150 nm to obtain an organic EL device. When an energization test was performed on this device, deep red EL emission with high color purity was obtained, and the x value in CIE 1931 chromaticity coordinates was 0.66. This device had an external quantum efficiency of 3.3% and a luminance half life of 500 hours or more.

Example 206 to Example 414
Except for using the compound shown in Table 19 instead of the compound (2) in Table 1, the compound H-25 in Table 4, and the compound H-1 in Table 2, they were all organic in the same manner as in Example 205. An EL element was produced. Table 19 shows the measurement results of the external quantum efficiency and the luminance half life of these elements. In addition, the compound (D) used in some Examples is described below. Further, all of the x values in the CIE1931 chromaticity coordinates of these elements were 0.65 or more.

Table 19

Example 415
On the cleaned glass plate with an ITO electrode, Clevios (registered trademark) P VP CH 8000 (registered trademark) manufactured by Heraeus was spin-coated to obtain a hole transport layer having a thickness of 50 nm. Next, the compound (1) in Table 1 and the compound H-1 in Table 2 were adjusted to a toluene solution with a solid content concentration of 2 wt% at a weight ratio of 3:97, and the solution was spin-coated to be on the hole transport phase. A light emitting layer having a thickness of 70 nm was stacked on the substrate. Subsequently, tris (8-hydroxyquinolinate) aluminum (Alq ₃ ) was deposited to obtain an electron injection layer having a film thickness of 15 nm. Further thereon, 1 nm of LiF was vapor-deposited, and then Al was vapor-deposited to form an electrode having a thickness of 150 nm to obtain an organic EL device. When an energization test was performed on this element, deep red EL light emission was obtained, and the x value in CIE 1931 chromaticity coordinates was 0.66. The external quantum efficiency of this device was 3.7%, and the luminance half life was 500 hours or more.

Example 416 to Example 510
An organic EL device was produced in the same manner as in Example 415 except that the compound shown in Table 20 was used instead of the compound (1) in Table 1 and the compound H-1 in Table 2. Table 20 shows the external quantum efficiency and luminance half-life of these devices. In addition, the x value in CIE 1931 chromaticity coordinates was 0.65 or more for all the elements.

Table 20

Example 511
On the cleaned glass plate with an ITO electrode, Clevios (registered trademark) P VP CH 8000 manufactured by Heraeus was spin-coated to obtain a hole transport layer having a thickness of 60 nm. Subsequently, the compound (3) in Table 1, the compound H-25 in Table 4, and the compound H-1 in Table 2 were adjusted to a toluene solution with a solid content concentration of 1.5 wt% at a weight ratio of 3: 7: 90. Then, the solution was spin-coated, and a light emitting layer having a thickness of 50 nm was laminated on the hole transport phase. Subsequently, the compound ET-6 of Table 14 was vapor-deposited, and the electron injection layer with a film thickness of 30 nm was obtained. Further thereon, 1 nm of LiF was vapor-deposited, and then Al was vapor-deposited to form an electrode having a thickness of 150 nm to obtain an organic EL device. When an energization test was performed on this element, deep red EL light emission was obtained, and the x value in CIE 1931 chromaticity coordinates was 0.66. The external quantum efficiency of this device was 2.9%, and the luminance half life was 500 hours or more.

Example 512-Example 720
In the same manner as in Example 511, except that the compound shown in Table 21 was used instead of the compound (3) in Table 1, Compound H-25 in Table 4, and Compound H-1 in Table 2, respectively. An organic EL element was produced. Table 21 shows the external quantum efficiency and luminance half-life of these devices. In all the elements, the x value in CIE1931 chromaticity coordinates was 0.65 or more.

Table 21

Example 721
A quartz substrate with a deposited film was prepared in the same manner as in Example 1 except that the following compound (E) was used in place of the compound H-1 in Table 2, and the emission spectrum by photoexcitation was measured. It was determined whether the peak wavelength of the obtained emission was in the range of 550 to 630 nm, and it was confirmed that it was in the range of 550 to 630 nm.

Example 722
On the washed glass plate with an ITO electrode, the compound HTM-2 of Table 12 was vacuum-deposited to obtain a 40 nm-thick hole transport layer. Subsequently, the compound (2) of Table 1, the said compound (E), and the said compound (D) were vacuum-deposited by weight ratio of 1:14:85, and the light emitting layer with a film thickness of 50 nm was obtained. Subsequently, compound EX-9 of Table 13 was vapor-deposited and the 30-nm-thick electron injection layer was obtained. Furthermore, after depositing 0.5 nm of LiF on it, Al was vapor-deposited to form an electrode having a thickness of 150 nm to obtain an organic EL device. When an energization test was performed on this device, deep red EL emission with high color purity was obtained, and the x value in CIE 1931 chromaticity coordinates was 0.66. This device had an external quantum efficiency of 3.1% and a luminance half life of 500 hours or more.

Example 723
A quartz substrate with a deposited film was prepared in the same manner as in Example 1 except that the following compound (F) was used in place of the compound H-1 in Table 2, and the emission spectrum by photoexcitation was measured. It was determined whether the peak wavelength of the obtained light emission was in the range of 550 to 630 nm, and it was confirmed that it was outside the range of 550 to 630 nm.

Example 724
On the washed glass plate with an ITO electrode, the compound HTM-2 of Table 12 was vacuum-deposited to obtain a 40 nm-thick hole transport layer. Next, a weight ratio of 0.5: 3.5: 11: 85 of the compound (2) of Table 1, the compound H-14 of Table 3, the compound (F), and the compound (D) Was vacuum evaporated to obtain a light-emitting layer having a thickness of 50 nm. Subsequently, compound EX-9 of Table 13 was vapor-deposited and the 30-nm-thick electron injection layer was obtained. Furthermore, after depositing 0.5 nm of LiF on it, Al was vapor-deposited to form an electrode having a thickness of 150 nm to obtain an organic EL device. When an energization test was performed on this device, deep red EL emission with high color purity was obtained, and the x value in CIE 1931 chromaticity coordinates was 0.66. This device had an external quantum efficiency of 2.8% and a luminance half-life of 500 hours or more.

Comparative Example 6
Instead of the compound H-14 in Table 3, the compound (2) in Table 1, the compound (F), and the compound (D) according to the ratio of materials when the compound (F) is used. Were prepared in the same manner as in Example 724 except that a light emitting layer was obtained by vacuum deposition at a weight ratio of 0.5: 14.5: 85. When an energization test was performed on this element, orange EL light emission was obtained, and the x value in CIE 1931 chromaticity coordinates was less than 0.62. This device had an external quantum efficiency of 0.8% and a luminance half life of 13 hours.

As described above, by using the light emitting material of the present invention, a high performance organic EL element can be produced. It is clear that remarkably high performance is exhibited as compared with the comparative example. The organic EL element has high luminous efficiency, low driving voltage, long life, high color purity, and x value of 0 in CIE1931 chromaticity coordinates. A deep red color of 65 or more can be achieved. This includes the material represented by the general formula [1] and / or the general formula [2] of the present invention and a material having a peak wavelength of the photoexcitation emission spectrum of the solid film of 550 to 630 nm. By using the light emitting material, energy transfer inside the device is excellent, and light emission from the material represented by the general formula [1] and / or the general formula [2] can be efficiently obtained. It is considered that light emission from materials other than [1] and / or the general formula [2] is sufficiently suppressed.

Claims (3)

A light-emitting material comprising a material represented by the following general formula [ 5 ] and / or the following general formula [ 6 ] and a material having a photoexcitation emission spectrum peak wavelength of the solid film of between 550 and 630 nm.
General formula [ 5 ]

(In the formula, each X independently represents a sulfur atom or an oxygen atom, and R ²⁶ and R ²⁷ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted group. Or an unsubstituted aryloxycarbonyl group,
R ^{28 to} R ⁴¹ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted silyl group, or a substituted amino group. Represent. )
General formula [ 6 ]

(In the formula, each X independently represents a sulfur atom or an oxygen atom, and R ⁴² and R ⁴³ each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted group. Or an unsubstituted aryloxycarbonyl group,
R ^{44 to} R ⁵⁷ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted silyl group, or a substituted amino group. Represent. ) General formula [5], and / or material represented by a general formula [6], the following general formula [7], and / or claim 1, wherein a material represented by the following general formula [8] Luminescent material.
General formula [7]

(Wherein R ⁵⁸ and R ⁵⁹ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryloxycarbonyl group;
R ^{60 to} R ⁶³ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted silyl group, or a substituted amino group. Represent. )
General formula [8]

(Wherein R ⁶⁴ and R ⁶⁵ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted aryloxycarbonyl group;
R ^{66 to} R ⁶⁹ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted silyl group, or a substituted amino group. Represent. ) Between a pair of electrodes including an anode and a cathode in the organic electroluminescent device obtained by forming an organic compound thin film of multiple layers including a light emitting layer or the emitting layer, the light emitting layer, according to claim 1 or 2, wherein the light emitting material An organic electroluminescence device comprising: