JP2004091334A - 2,6-arylaminoanthracene compound, charge transport material, and organic electroluminescent element - Google Patents

2,6-arylaminoanthracene compound, charge transport material, and organic electroluminescent element Download PDF

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JP2004091334A
JP2004091334A JP2002251263A JP2002251263A JP2004091334A JP 2004091334 A JP2004091334 A JP 2004091334A JP 2002251263 A JP2002251263 A JP 2002251263A JP 2002251263 A JP2002251263 A JP 2002251263A JP 2004091334 A JP2004091334 A JP 2004091334A
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Japan
Prior art keywords
group
arylaminoanthracene
general formula
compound
substituent
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JP2002251263A
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Japanese (ja)
Inventor
Akiko Ichinosawa
Hideki Sato
Yoshiharu Sato
佐藤 佳晴
佐藤 秀樹
市野澤 晶子
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Mitsubishi Chemicals Corp
三菱化学株式会社
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Abstract

<P>PROBLEM TO BE SOLVED: To provide a new compound with low ionization potential and excellent hole transport properties and to provide a charge transport material and an organic electroluminescent element both using the compound. <P>SOLUTION: The new compound is a 2,6-arylaminoanthracene compound represented by general formula (I). The charge transport material contains this new compound. The organic electroluminescent element has a pair of electrodes and an organic light-emitting layer disposed between the electrodes on a substrate; in the element, a layer containing the anthracene compound is disposed as the organic light-emitting layer and/or as a layer disposed between the organic light-emitting layer and the electrode. <P>COPYRIGHT: (C)2004,JPO

Description

[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a novel 2,6-arylaminoanthracene-based compound which is expected to be used as a charge transporting material in a hole transporting material or a host material of an organic electroluminescent device, an organic photoreceptor (OPC), and the like. The present invention relates to a charge transport material comprising a 6-arylaminoanthracene-based compound and an organic electroluminescent device using the 2,6-arylaminoanthracene-based compound.
[0002]
[Prior art]
In general, the simplest structure of an electroluminescent element using an organic substance includes a structure including a light emitting layer and a pair of opposed electrodes sandwiching the layer. This is because when an electric field is applied between the two electrodes, electrons are injected from the cathode side, holes are injected from the anode, and they recombine in the light emitting layer, and the energy level changes from the conduction band to the valence band. It uses the phenomenon of emitting light as energy when returning.
[0003]
In order to apply an organic electroluminescent device to a display device such as a flat panel display, it is necessary to ensure sufficient reliability of the device.
[0004]
The device may be degraded due to the high symmetry and low glass transition temperature of the compounds contained in each layer, which may cause crystallization due to a rise in temperature, or may cause mutual interference between the light emitting layer and the adjacent charge transporting layer. Or cause a diffusion phenomenon. For example, in a two-layer element structure of a hole transport layer and a light emitting layer, an interdiffusion phenomenon may occur between the two layers.
[0005]
Further, for example, when the hole-transporting ability of the compound constituting the hole-transporting layer is insufficient, the organic electroluminescent device using the compound loses the charge injection balance when driven and the hole space charge is reduced. As a result, the amount of electrons injected into the light-emitting layer increases, causing reduction and degradation of the light-emitting material. As a result, a deterioration phenomenon in which the light emitting characteristics of the element, particularly the driving voltage is increased, appears, which ultimately leads to a shortened driving life.
[0006]
In order to solve such a problem, a hole transporting material having a high hole transporting ability (hole transporting property) and a high glass transition temperature has been demanded.
[0007]
Conventionally, JP-A-2001-131541 describes the following exemplary compound (P-1) as a material for a light-emitting layer or a hole transport layer in an organic electroluminescent device.
[0008]
Embedded image
[0009]
However, since this compound (P-1) has a small number of arylamine units and a low hole-transport property, an organic electroluminescent device using the compound does not easily allow a current to flow through the device, resulting in poor luminous brightness and luminous efficiency. Fear to be enough.
[0010]
Further, JP-A-10-302960 describes the following compound (P-2) as a material for an organic electroluminescent device.
[0011]
Embedded image
[0012]
This compound (P-2) has a large number of arylamine units in one molecule, but the arylamine unit in the center of the compound is surrounded by a triphenylmethane unit. It is considered that the hole transportability cannot be sufficiently exhibited. In addition, since the molecular weight is very large, it is expected that it is difficult to form a thin film by vapor deposition.
[0013]
In addition, JP-A-10-72580 describes the following compound (P-3), and JP-A-7-109449 describes the following compound (P-4).
[0014]
Embedded image
[0015]
However, in the compound (P-3), the arylamine unit is substituted at the 9,10-position of anthracene, which prevents conjugation of the entire molecule. For this reason, it is difficult to obtain a low ionization potential, which is not preferable as a molecular design of the hole transporting material.
[0016]
In addition, compound (P-4) is considered to have an insufficient hole transporting property because the compound has a small number of arylamine units in the molecule, similarly to compound (P-1) described above.
[0017]
Compounds (P-2) and (P-3) each have an arylamino group substituted with an arylamino group. However, since the molecular design, specifically, the substitution position and the like are not appropriate, sufficient It cannot be said that it has a hole transporting property, and further improvement of the hole transporting property is required.
[0018]
[Problems to be solved by the invention]
An object of the present invention is to solve the above conventional problems and to provide a novel compound having a low ionization potential and excellent hole transportability, and a charge transport material and an organic electroluminescent device using such a compound. And
[0019]
[Means for Solving the Problems]
The 2,6-arylaminoanthracene-based compound of the present invention is represented by the following general formula (I).
[0020]
Embedded image
[0021]
(In the above general formula (I), R 1 ~ R 6 Each independently represents an alkyl group, an aromatic hydrocarbon group or an aromatic heterocyclic group, each of which may have a substituent. Also, R 1 Or R 6 May form a ring by bonding adjacent groups or by bonding to a carbon atom constituting a benzene ring or an anthracene ring in the above general formula (I).
Further, the benzene ring and the anthracene ring in the general formula (I) may have a substituent other than the amino group specified in the formula. )
[0022]
That is, the present inventors have eagerly considered a compound having an excellent hole transporting property as to a substitution position of an arylamino group effective for effectively expanding an intramolecular conjugated double bond system in order to lower the ionization potential of the compound. By repeating studies and substituting an arylamino group having a high hole transporting property at the 2,6-position of the anthracene skeleton, the intramolecular conjugated double bond system can be effectively expanded, and the ionization potential of the compound can be reduced. The present inventors have found that it is possible to improve the hole transport property by lowering the pressure, and have reached the present invention.
[0023]
The 2,6-arylaminoanthracene-based compound of the present invention represented by the above general formula (I) is also preferable in that it has low crystallinity.
[0024]
That is, for example, in an anthracene-based compound in which an arylamino group is substituted at the 9,10-position described in Japanese Patent Application Laid-Open No. 10-72580, the crystallinity is high due to too high symmetry of the molecule. Although the thin film containing the compound has a problem that it is easily crystallized, the anthracene-based compound of the present invention represented by the general formula (I) is a 2,6-substituted compound, so that the tendency of crystallization is reduced.
[0025]
The 2,6-arylaminoanthracene-based compound of the present invention has low crystallinity, a high glass transition temperature (Tg), and a high charge transporting property. It can be suitably used for an electroluminescent element, a photoelectric conversion element, an organic solar cell, an organic rectifying element, and the like.
[0026]
The charge transport material of the present invention contains such a 2,6-arylaminoanthracene-based compound of the present invention, and has a low ionization potential and excellent hole transportability.
[0027]
The organic electroluminescent device of the present invention is an organic electroluminescent device having a pair of electrodes and an organic light emitting layer provided between both electrodes on a substrate. A layer provided between the layer and the electrode has a layer containing the 2,6-arylaminoanthracene compound of the present invention, has a low ionization potential, is excellent in hole transportability, and has low crystallinity. Furthermore, an organic electroluminescent element having high emission luminance and luminous efficiency and excellent light emitting element characteristics can be realized by using a 2,6-arylaminoanthracene compound having a high melting point and a high Tg.
[0028]
BEST MODE FOR CARRYING OUT THE INVENTION
Hereinafter, embodiments of the present invention will be described in detail.
[0029]
First, the 2,6-arylaminoanthracene-based compound of the present invention will be described.
[0030]
The 2,6-arylaminoanthracene-based compound of the present invention is represented by the general formula (I), and is an arylamino group substituted with an amino group, that is,
Embedded image
And is characterized in that the 2,6-position of the anthracene skeleton as a mother skeleton is substituted.
[0031]
In the general formula (I), R 1 Or R 6 Each independently represents an alkyl group which may have a substituent, an aromatic hydrocarbon group or an aromatic heterocyclic group which may have a substituent, and specifically, for example, a methyl group, ethyl Or a linear or branched alkyl group having 1 to 6 carbon atoms such as a tert-butyl group or a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a thienyl group, a furyl group, a carbazolyl group or the like. A group consisting of a 6-membered monocyclic ring or a 2 to 3 condensed ring is exemplified.
[0032]
The substituent which the alkyl group, aromatic hydrocarbon group or aromatic heterocyclic group may have is not particularly limited, and may be, for example,
A halogen atom which is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
A linear or branched alkyl group having 1 to 6 carbon atoms such as a methyl group and an ethyl group;
A linear or branched alkenyl group having 2 to 7 carbon atoms such as a vinyl group and an allyl group;
A linear or branched alkoxy group having 1 to 6 carbon atoms such as a methoxy group and an ethoxy group;
An alkoxycarbonyl group having 2 to 7 carbon atoms such as a methoxycarbonyl group and an ethoxycarbonyl group;
Aryloxy groups such as phenoxy and naphthoxy;
An aralkyloxy group such as a benzyloxy group;
A dialkylamino group having a linear or branched alkyl group having 1 to 6 carbon atoms, such as a diethylamino group, a diisopropylamino group, and a methylethylamino group;
Diarylamino groups such as diphenylamino group and phenylnaphthylamino group;
A diaralkylamino group such as a dibenzylamino group or a diphenethylamino group;
Aralkyl groups such as benzyl and phenethyl;
Aromatic hydrocarbon groups such as phenyl and naphthyl;
Aromatic heterocyclic groups such as a thienyl group, a furyl group, a pyridyl group and a quinolyl group;
And the like.
[0033]
R 1 And R 6 Is particularly preferably a phenyl group, a naphthyl group, a phenanthryl group or a methyl group which may have a substituent. As the naphthyl group, a β-naphthyl group is particularly preferred.
[0034]
Also, R 1 Or R 6 May form a ring by bonding adjacent groups or by bonding to a carbon atom constituting a benzene ring or an anthracene ring in the general formula (I).
[0035]
Specifically, the following structure in the general formula (I)
Embedded image
At
R 1 And R 2 ,
R 1 And / or R 2 And -NR 1 R 2 A carbon atom constituting a benzene ring to which the group is bonded,
R 3 And -NR 3 A carbon atom constituting a benzene ring or an anthracene ring to which-is bonded,
May combine with each other to form a ring.
[0036]
In the above structure, examples of forming such a ring include the following.
[0037]
Embedded image
[0038]
Although the description is omitted in the above example, the portion corresponding to the benzene ring specified in Chemical formula 8 may have a substituent described later. Also, R 1 Or R 3 May also have a substituent, and the substituent may be R 1 Or R 3 Examples of the group which may have the above-mentioned groups.
[0039]
Similarly, the following structure in the general formula (I)
Embedded image
R in 4 Or R 6 May form a similar ring.
[0040]
The benzene ring and the anthracene ring in the general formula (I) are an amino group specified in the formula, that is,
Embedded image
In addition, they may have a substituent.
[0041]
The substituent is not particularly limited as long as the performance of the compound of the present invention is not impaired.For example, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, Selected from an aromatic hydrocarbon group optionally having a substituent, an aromatic heterocyclic group optionally having a substituent, and an aryloxy group optionally having a substituent, or A ring condensed with a benzene ring or an anthracene ring in the formula (II) is formed. Specific examples of the above substituents include R 1 Or R 6 In the above, the alkyl group, aromatic hydrocarbon group and aromatic heterocyclic group, and the groups which these may have may be those described above.
[0042]
The 2,6-arylaminoanthracene-based compound of the present invention represented by the general formula (I) is particularly preferably represented by the following general formula (II).
[0043]
Embedded image
[0044]
(In the above general formula (II), R 1 ~ R 6 Has the same meaning as in formula (I). R 7 And R 8 Each independently represents an alkyl group, an aromatic hydrocarbon group or an aromatic heterocyclic group, each of which may have a substituent. Further, the benzene ring and the anthracene ring in the general formula (II) represent an amino group, R 7 And R 8 It may have a substituent in addition to the above. )
[0045]
R in the above general formula (II) 7 And R 8 As a specific example of, R in the general formula (I) 1 ~ R 6 The same groups as those mentioned in the description section can be used. R 7 And R 8 Is preferably an aromatic hydrocarbon group which may have a substituent, more preferably a phenyl group which may have a substituent.
[0046]
In the compound represented by the general formula (II), in particular, in the general formula (II), R 7 And R 8 Is an aromatic hydrocarbon group, the base skeleton (anthracene skeleton in which an aromatic hydrocarbon group is bonded to the 9,10-position) is rigid, so that the terminal group (the 2,6-position arylamino group) This is also preferable in that a decrease in the glass transition temperature (Tg), which is a concern when the length is longer, can be avoided and a high melting point and high Tg material can be obtained.
[0047]
In the general formula (II), a benzene ring and an anthracene ring represent an amino group, R 7 And R 8 In addition, they may have a substituent.
[0048]
Examples of the substituent include the same groups as the groups which the benzene ring and the anthracene ring in the formula (I) may have in addition to the amino group specified in the formula.
[0049]
The following compounds (A-1) to (A-72) are illustrated as typical examples of the 2,6-arylaminoanthracene-based compound of the present invention. It is not limited to these.
[0050]
[Table 1]
[0051]
[Table 2]
[0052]
[Table 3]
[0053]
[Table 4]
[0054]
[Table 5]
[0055]
[Table 6]
[0056]
[Table 7]
[0057]
[Table 8]
[0058]
[Table 9]
[0059]
[Table 10]
[0060]
Embedded image
[0061]
The 2,6-arylaminoanthracene compound represented by the general formula (I) generally has a molecular weight of about 450 to 2,000, preferably about 800 to 1,500.
[0062]
Further, the 2,6-arylaminoanthracene-based compound of the present invention is suitable for obtaining a compound having a low ionization potential. The ionization potential of the compound is preferably 5.3 eV or less. The lower limit of the ionization potential is not particularly limited, but is preferably about 4.5 eV.
[0063]
The 2,6-arylaminoanthracene-based compound of the present invention has low crystallinity, a high glass transition temperature (Tg), and a high charge transporting property. It can be suitably used for an electroluminescent element, a photoelectric conversion element, an organic solar cell, an organic rectifying element, and the like.
[0064]
Next, the organic electroluminescent device of the present invention using such a 2,6-arylaminoanthracene compound of the present invention as a charge transporting material will be described.
[0065]
The organic electroluminescent device of the present invention has a pair of electrodes consisting of an anode and a cathode, and an organic light emitting layer provided between the two electrodes, and as the organic light emitting layer, and / or the organic light emitting layer and the electrode As a layer provided therebetween, a layer containing the 2,6-arylaminoanthracene-based compound of the present invention represented by the general formula (I) is provided.
[0066]
The layer containing the 2,6-arylaminoanthracene compound of the present invention may be any layer between the anode and the cathode, and may be used as a host material or a dopant material in, for example, a light-emitting layer described below. Alternatively, it may be used as a charge transporting layer provided between the electrode and the light emitting layer. Among them, it is preferable to provide a hole injecting / transporting layer between the anode and the light emitting layer.
[0067]
In the organic electroluminescent device of the present invention, two or more anthracene-based compounds may be contained in the same layer, and when the anthracene-based compound is contained in two or more layers, these may be used. The anthracene-based compounds contained in the layer may be the same or different.
[0068]
Hereinafter, embodiments of the organic electroluminescent device of the present invention will be described in detail with reference to the drawings.
[0069]
In the organic electroluminescent device of the present invention, when the number of layers between the anode and the light-emitting layer is one, the layer is referred to as a “hole transport layer”. Buffer layer "and other layers are collectively referred to as" hole transport layer ".
[0070]
1 to 3 are cross-sectional views schematically showing examples of the structure of the organic electroluminescent device of the present invention, but the organic electroluminescent device of the present invention is not limited to those shown in the drawings. 1 to 3, 1 represents a substrate, 2 represents an anode, 3 represents a positive buffer layer, 4 represents a hole transport layer, 5 represents a light emitting layer, 6 represents an electron transport layer, and 7 represents a cathode.
[0071]
The substrate 1 serves as a support for the organic electroluminescent element, and a quartz plate, a glass plate, a metal plate or a metal foil, a plastic film or a sheet, or the like is used. Particularly, a glass plate or a transparent synthetic resin sheet such as polyester, polymethacrylate, polycarbonate, and polysulfone is preferable. When using a synthetic resin for the substrate, it is necessary to pay attention to gas barrier properties. If the gas barrier property of the substrate is low, the organic electroluminescent element may be deteriorated by the outside air passing through the substrate. Therefore, when a synthetic resin is used for the substrate, it is preferable to provide a dense silicon oxide film or the like on one or both surfaces of the substrate to enhance gas barrier properties.
[0072]
An anode 2 is provided on a substrate 1. The anode 2 plays a role of injecting holes into the hole transport layer 4. The anode 2 is usually made of a metal such as aluminum, gold, silver, nickel, palladium, and platinum; a conductive metal oxide such as an oxide of indium and / or tin; a metal halide such as copper iodide; Alternatively, it is formed of a conductive polymer such as poly (3-methylthiophene), polypyrrole, or polyaniline. The anode 2 is usually formed by sputtering, vacuum deposition, or the like on the substrate 1 in many cases. When the anode 2 is formed of silver or other metal fine particles, copper iodide or other fine particles, carbon black, conductive metal oxide fine particles, conductive polymer fine powder, or the like, an appropriate binder resin solution may be used. It can also be formed by a method of dispersing and applying on the substrate 1. Further, when the anode 2 is formed of a conductive polymer, a method of directly forming a polymerized thin film on the substrate 1 by electrolytic polymerization or a method of applying a conductive polymer solution on the substrate 1 can be employed (Appl. Phys. Lett., 60, 2711, 1992). The anode 2 usually has a single-layer structure, but may have a laminated structure of a plurality of materials if desired.
[0073]
The anode 2 may be opaque, but is preferably transparent. Usually, the transmittance of visible light is preferably 60% or more, particularly preferably 80% or more. In order to ensure this transparency, the upper limit of the thickness of the anode 2 is usually 1000 nm, preferably 500 nm, and the lower limit is usually 5 nm, preferably 10 nm. If it is opaque, the thickness of the anode 2 is arbitrary, and the anode 2 may be formed of metal and serve as the substrate 1 as desired.
[0074]
In the case of the device having the configuration shown in FIG. 1, a hole transport layer 4 is provided on the anode 2. As a condition required for the material of the hole transport layer 4, it is necessary that the material has a high hole injection efficiency from the anode 2 and can efficiently transport the injected holes. For this purpose, it is required that the ionization potential is low, the transparency to visible light is high, the hole mobility is high, the stability is excellent, and impurities serving as traps are hardly generated during manufacturing or use. Is done. In addition to the above general requirements, the element is required to have a heat resistance of 100 ° C. or more depending on the application. Therefore, a material having a glass transition temperature (Tg) of 100 ° C. or more is preferable.
[0075]
The organic electroluminescent device of the present invention preferably contains one or two or more anthracene-based compounds selected from the group consisting of the compounds represented by the general formula (I) as the hole transporting material.
[0076]
The hole transport layer 4 may contain a known hole transport material in addition to the anthracene compound represented by the general formula (I), as long as the object of the present invention is not impaired.
[0077]
Known hole-transporting materials include, for example, aromatic diamine compounds linked to tertiary aromatic amine units such as 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane (JP-A-59-1984). 194393) and two or more condensed aromatic rings containing two or more tertiary amines represented by 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl Substituted aromatic amine (JP-A-5-234681), aromatic triamine having a starburst structure as a derivative of triphenylbenzene (U.S. Pat. No. 4,923,774), N, N'-diphenyl-N , N'-bis (3-methylphenyl) biphenyl-4,4'-diamine and other aromatic diamines (U.S. Pat. No. 4,764,625); α, α, α ', α'-tetramethyl- α, α'-bis (4-di-p-tolylaminophenyl) -p-xylene (JP-A-3-269084) and triphenylamine derivatives which are sterically asymmetric as a whole molecule (JP-A-4-129271) Gazette), a compound in which a pyrenyl group is substituted with a plurality of aromatic diamino groups (JP-A-4-175395), and an aromatic diamine in which a tertiary aromatic amine unit is linked by an ethylene group (JP-A-4-264189). , An aromatic diamine having a styryl structure (JP-A-4-290851), an aromatic tertiary amine unit linked by a thiophene group (JP-A-4-304466), and a starburst type aromatic triamine (JP-A-4-304466). 4-308688), a benzylphenyl compound (JP-A-4-364153), and a tertiary amine with a fluorene group. (JP-A-5-25473), triamine compound (JP-A-5-239455), bisdipyridylaminobiphenyl (JP-A-5-320634), N, N, N-triphenylamine derivative ( JP-A-6-1972), aromatic diamines having a phenoxazine structure (JP-A-7-138562), diaminophenylphenanthridine derivatives (JP-A-7-252474), and hydrazone compounds (JP-A-2-132). 315991), silazane compounds (U.S. Pat. No. 4,950,950), silanamin derivatives (JP-A-6-49079), phosphamine derivatives (JP-A-6-25659), quinacridone compounds and the like. . These compounds may be used alone, or may be used as a mixture as necessary.
[0078]
In addition to the above compounds, examples of materials for the hole transport layer 4 include polyvinyl carbazole and polysilane (Appl. Phys. Lett., Vol. 59, p. 2760, 1991), polyphosphazene (JP-A-5-310949), Polyamide (JP-A-5-310949), polyvinyl triphenylamine (JP-A-7-53953), polymer having a triphenylamine skeleton (JP-A-4-1330065), methylene group having a triphenylamine unit (Synthetic Metals, vol. 55-57, p. 4163, 1993), polymethacrylate containing an aromatic amine (J. Polym. Sci., Polym. Chem. Ed., 21, 969). , 1983).
[0079]
The hole transport layer 4 containing the anthracene compound represented by the general formula (I) is formed on the anode 2 by a coating method or a vacuum deposition method.
[0080]
In the case of using the coating method, a coating solution prepared by adding one or more hole transport materials and, if necessary, an additive such as a binder resin or a coating property improving agent that does not trap holes, The hole transport layer 4 is formed by applying the solution on the anode 2 by a known application method such as a spin coating method and drying. As the binder resin, polycarbonate, polyarylate, polyester, or the like is used. If the amount of the binder resin in the hole transport layer 4 is large, the hole mobility decreases, so the binder resin is preferably used so that the content in the hole transport layer 4 is 50% by weight or less, and 30% by weight. % Is more preferable.
[0081]
In the case of using the vacuum evaporation method, the hole transporting material is put in a crucible, placed in a vacuum vessel, and the anode 2 is arranged to face the crucible. Vacuum pump inside the vacuum vessel 10 -4 After evacuation to about Pa, the crucible is heated to evaporate the hole transporting material, and the generated vapor is deposited on the anode 2.
[0082]
When the anthracene-based compound of the present invention is used in combination with a known hole-transporting material, in order to sufficiently exhibit the effects of the anthracene-based compound of the present invention, the content of the anthracene-based compound in the total amount of the hole-transporting material is included. The amount is preferably at least 50% by weight, especially at least 80% by weight.
[0083]
The upper limit of the thickness of the hole transport layer 4 containing the anthracene compound of the present invention is usually 300 nm, preferably 100 nm, and the lower limit is usually 5 nm, preferably 10 nm. It is preferable that the thin hole transport layer 4 be formed by a vacuum deposition method that can easily form a thin film uniformly.
[0084]
In the device having the layer configuration shown in FIG. 1, a light emitting layer 5 is provided on the hole transport layer 4. The light emitting layer 5 is formed of a material that efficiently recombines electrons injected from the cathode 7 and holes injected from the anode 2 between electrodes to which an electric field is applied, and emits light efficiently by the recombination.
[0085]
Materials satisfying such conditions include aromatic compounds such as tetraphenylbutadiene (JP-A-57-51781) and metal complexes such as aluminum complex of 8-hydroxyquinoline (JP-A-59-194393). Metal complex of 10-hydroxybenzo [h] quinoline (JP-A-6-322362), mixed ligand aluminum chelate complex (JP-A-5-198377, JP-A-5-198378, JP-A-5-1983) 214332, JP-A-6-172751), cyclopentadiene derivative (JP-A-2-289675), perinone derivative (JP-A-2-289676), and oxadiazole derivative (JP-A-2-216791) ), Bisstyrylbenzene derivatives (Japanese Patent Application Laid-Open Nos. 1-245087 and 2- JP-A-222484), perylene derivatives (JP-A-2-189890, JP-A-3-791), coumarin compounds (JP-A-2-191694 and JP-A-3-792), rare-earth complexes (JP-A-1-18998). No. 256584), distyrylpyrazine derivatives (JP-A-2-252793), p-phenylene compounds (JP-A-3-33183), thiadiazolopyridine derivatives (JP-A-3-37292), pyrrolopyridine Derivatives (JP-A-3-37293), naphthyridine derivatives (JP-A-3-203982), and silole derivatives (The 70th Annual Meeting of the Chemical Society of Japan, 2D102 and 2D103)
, 1996).
[0086]
It is effective to dope a luminescent dye with the above luminescent layer material as a host material for the purpose of improving the driving life of the device. For example, a naphthacene derivative represented by rubrene (JP-A-4-335087) and a quinacridone derivative (JP-A-5-70773) using a metal complex such as an 8-hydroxyquinoline driving element complex of an aluminum element as a host material. By doping 0.1 to 10% by weight of a condensed polycyclic aromatic ring such as perylene or the like (Japanese Patent Laid-Open No. 5-198377) with respect to the host material, the light-emitting characteristics of the device, particularly the driving stability, can be increased. Can be improved.
[0087]
As described above, the 2,6-arylaminoanthracene-based compound of the present invention may be used in this light emitting layer. In that case, the host material as described above may be used by doping it, and the 2,6-arylaminoanthracene-based compound of the present invention may be used as the host material, and the above-described luminescent dye (fluorescent dye or phosphorescent dye) may be used. May be used after doping.
[0088]
The light emitting layer 5 can be formed in the same manner as the hole transport layer 4, but usually, a vacuum evaporation method is used. As a method for doping the host material of the light emitting layer 5 with a light emitting dye, there are a method of co-evaporation and a method of previously mixing an evaporation source at a predetermined concentration.
[0089]
When each of the above dopants is doped into the light emitting layer 5, it is usually uniformly doped in the thickness direction of the light emitting layer 5, but may have a concentration distribution in the film thickness direction. For example, doping may be performed only in the vicinity of the interface on the hole transport layer 4 side, or conversely, may be performed only in the vicinity of the interface on the cathode 7 side.
[0090]
The upper limit of the thickness of the light emitting layer 5 is usually 200 nm, preferably 100 nm, and the lower limit is usually 10 nm, preferably 30 nm.
[0091]
In the device of FIG. 1, the cathode 7 provided on the light emitting layer 5 plays a role of injecting electrons into the light emitting layer 5. As the material used for the cathode 7, the same material as the material used for the anode 2 can be used. However, for efficient electron injection, a metal having a low work function is preferable. Suitable metals such as indium, calcium, aluminum, silver and the like or alloys thereof are used. Specific examples include a low work function alloy electrode such as a magnesium-silver alloy, a magnesium-indium alloy, and an aluminum-lithium alloy.
[0092]
The thickness of the cathode 7 is usually the same as that of the anode 2.
[0093]
For the purpose of protecting the cathode 7 made of a low work function metal, a metal layer having a high work function and being stable to the atmosphere is preferably further laminated thereon to increase the stability of the device. As the stable metal layer, a metal such as aluminum, silver, nickel, chromium, gold, and platinum is used.
[0094]
Further, LiF, LiF is provided at the interface between the cathode 7 and the light emitting layer 5 or the electron transport layer 6 shown in FIG. 2 Inserting an ultrathin film (0.1 to 5 nm) of O or the like is also an effective method for improving the efficiency of the device, and is preferable (Appl. Phys. Lett., 70, 152, 1997; IEEE Trans). Electron Devices, 44, 1245, 1997).
[0095]
Further, an interface layer made of an organic compound may be provided between the cathode 7 and the light emitting layer 5 or the electron transport layer 6 shown in FIG. Compounds used in the cathode interface layer include aromatic diamine compounds (JP-A-6-267658), quinacridone compounds (JP-A-6-330031), naphthacene derivatives (JP-A-6-330032), and organic compounds. Silicon compounds (JP-A-6-325871), organic phosphorus compounds (JP-A-5-325872), compounds having an N-phenylcarbazole skeleton (JP-A-8-60144), N-vinylcarbazole polymers ( JP-A-8-60145) and the like.
[0096]
The upper limit of the thickness of such an interface layer is usually 100 nm, preferably 30 nm, and the lower limit is usually 2 nm, preferably 5 nm.
[0097]
Instead of providing the interface layer, a region containing 50% by weight or more of the material of the interface layer may be provided near the interface of the light emitting layer 5 or the electron transport layer 6 in FIG.
[0098]
In the device having the configuration shown in FIG. 1, the hole transport layer 4 has a function of receiving holes from the anode 2 (hole injection) and a function of transporting the received holes toward the light emitting layer 5 (hole transport). The light emitting layer 5 also has a function of receiving electrons from the cathode 8 (electron injection), a function of transporting electrons received from the cathode 8 to the light emitting layer 5 (electron transport), and a light emitting function.
[0099]
However, in order to further improve the light emitting characteristics and driving stability of the device of the present invention, for example, as shown in FIG. 3, an electron transporting layer 6 is provided between the cathode 7 and the light emitting layer 5; As shown in FIG. 3, it is also possible to provide an anode buffer layer 3 between the anode 2 and the hole transport layer 4 to form a structure in which the layers are separated for each function, that is, a function-separated element.
[0100]
In the organic electroluminescent device shown in FIG. 3, the material forming the electron transport layer 6 is required to be capable of easily injecting electrons from the cathode 7 and having a high electron transport ability. Examples of such an electron transporting material include metal complexes such as an aluminum complex of 8-hydroxyquinoline (JP-A-59-194393), and 10-hydroxybenzo [h] quinoline, which have already been mentioned as a material for forming the light-emitting layer 5. Metal complex (JP-A-6-322362), mixed ligand aluminum chelate complex (JP-A-5-198377, JP-A-5-198378, JP-A-5-214332, JP-A-6-172751) Patent Document 1: Cyclopentadiene derivative (JP-A-2-289675), Perinone derivative (JP-A-2-289676), oxadiazole derivative (JP-A-2-216791), bisstyrylbenzene derivative (JP-A-1-289675) Nos. 245087 and 2-222484), perylene derivatives (Japanese Unexamined Patent Publication No. Nos. 89890 and 3-791), coumarin compounds (JP-A-2-191694 and JP-A-3-792), rare earth complexes (JP-A-1-256584), and distyrylpyrazine derivatives (JP-A-Heisei 2-256584). JP-A-2-252793), p-phenylene compound (JP-A-3-33183), thiadiazolopyridine derivative (JP-A-3-37292), pyrrolopyridine derivative (JP-A-3-37293), naphthyridine Derivatives (JP-A-3-203982), and silole derivatives (The 70th Annual Meeting of the Chemical Society of Japan, 2D102 and 2D103, 1996).
[0101]
The electron transport layer 6 is formed by laminating on the light emitting layer 5 by a coating method or a vacuum deposition method in the same manner as the hole transport layer 4. Usually, a vacuum evaporation method is used.
[0102]
The upper limit of the thickness of the electron transport layer 6 is usually 200 nm, preferably 100 nm, and the lower limit is usually 5 nm, preferably 10 nm.
[0103]
As shown in FIGS. 2 and 3, an anode buffer layer 3 is provided between the hole transport layer 4 and the anode 2 for the purpose of improving the efficiency of hole injection and improving the adhesion of the entire organic layer to the anode. Inserting has also been done.
[0104]
The insertion of the anode buffer layer 3 has the effect of reducing the initial drive voltage of the device and suppressing the voltage rise when the device is continuously driven with a constant current. The conditions required for the material used for the anode buffer layer 3 include a good contact with the anode 2, a uniform thin film can be formed, and thermal stability, that is, a high melting point and a high glass transition temperature. Is preferable, and the glass transition temperature is preferably 100 ° C. or more. In addition, the ionization potential is low, holes can be easily injected from the anode, and the hole mobility is high.
[0105]
For this purpose, porphyrin derivatives, phthalocyanine compounds (JP-A-63-295695), hydrazone compounds, alkoxy-substituted aromatic diamine derivatives, p- (9-anthryl) -N, N'-di -P-tolylaniline, polythienylenevinylene, poly-p-phenylenevinylene, polyaniline (Appl. Phys. Lett., 64, 1245, 1994), polythiophene (Optical Materials, 9, 125, 1998) ), An organic compound such as a star-bust type aromatic triamine (Japanese Patent Application Laid-Open No. 4-308688), a sputtered carbon film (Synth. Met., Vol. 91, p. 73, 1997), vanadium oxide, ruthenium oxide Oxides, metal oxides such as molybdenum oxide (JP ys. D, 29, pp. 2750, 1996) have been reported.
[0106]
Further, a layer containing a low-molecular organic compound having a hole injecting / transporting property and an electron-accepting compound (described in JP-A-11-251067 and JP-A-2000-159221), an aromatic amino group, and the like may be used. A layer formed by doping a non-conjugated polymer compound containing an electron-accepting compound as necessary (Japanese Patent Application Laid-Open Nos. 11-135262, 11-283750, 2000-36390, and Japanese Unexamined Patent Publication No. 2000-150168, Japanese Unexamined Patent Application Publication No. 2001-223084, and WO97 / 33193), or a layer containing a conductive polymer such as polythiophene (Japanese Unexamined Patent Application Publication No. 10-92584). However, the present invention is not limited to this.
[0107]
As the material for the anode buffer layer, any of low-molecular and high-molecular compounds can be used.
[0108]
Of the low molecular weight compounds, porphine compounds or phthalocyanine compounds are often used. These compounds may have a central metal or may be non-metallic. Preferred examples of these compounds include the following compounds:
Porfin
5,10,15,20-tetraphenyl-21H, 23H-porphine
5,10,15,20-Tetraphenyl-21H, 23H-porphine cobalt (II)
5,10,15,20-Tetraphenyl-21H, 23H-porphine copper (II)
5,10,15,20-Tetraphenyl-21H, 23H-porphine zinc (II)
5,10,15,20-tetraphenyl-21H, 23H-porphine vanadium (IV) oxide
5,10,15,20-tetra (4-pyridyl) -21H, 23H-porphine
29H, 31H-phthalocyanine
Copper (II) phthalocyanine
Zinc (II) phthalocyanine
Titanium phthalocyanine oxide
Magnesium phthalocyanine
Lead phthalocyanine
Copper (II) 4,4'4 ", 4 '"-tetraaza-29H, 31H-phthalocyanine
[0109]
Incidentally, the 2,6-arylaminoanthracene-based compound of the present invention may be used for this anode buffer layer. When used for the layer, those having a relatively low ionization potential are preferred, and specifically those having about 4.9 eV or less are particularly preferred.
[0110]
In the case of the anode buffer layer, when a low-molecular compound is used, a thin film can be formed in the same manner as the above-described hole transport layer.However, when an inorganic substance is used, a sputtering method, an electron beam evaporation method, The CVD method is used.
[0111]
As described above, the lower limit of the thickness of the anode buffer layer 3 formed by using a low molecular compound is usually 3 nm, preferably about 10 nm, and the upper limit is usually 100 nm, preferably about 50 nm.
[0112]
When a polymer compound is used, for example, the polymer compound and the electron-accepting compound, and if necessary, an additive such as a coatability improving agent such as a binder resin or a leveling agent that does not trap holes are added and dissolved. The coating solution is prepared, applied to the anode 2 by a usual coating method such as a spray method, a printing method, a spin coating method, a dip coating method, a die coating method, or an ink jet method, and dried to form an anode buffer layer 3. Can be formed as a thin film.
[0113]
Examples of the binder resin used here include polycarbonate, polyarylate, polyester and the like. If the content of the binder resin in the layer is large, the hole mobility may be reduced. Therefore, the content is preferably small, and the content in the anode buffer layer 3 is preferably 50% by weight or less.
[0114]
Further, a thin film is formed in advance on a medium such as a film, a support substrate, and a roll by the above-described thin film forming method, and the thin film on the medium is thermally or pressure-transferred onto the anode 2 to form the thin film. Can also be.
[0115]
As described above, the lower limit of the thickness of the anode buffer layer 3 formed using a polymer compound is usually 5 nm, preferably about 10 nm, and the upper limit is usually 1000 nm for the same reason as described above. , Preferably about 500 nm.
[0116]
Although not shown, by providing a hole blocking layer in contact with the cathode side interface of the light emitting layer 5, it is possible to further improve the luminous efficiency of the device.
[0117]
The hole blocking layer has a role of preventing holes moving from the hole transport layer from reaching the cathode and a role of efficiently transporting electrons injected from the electron injection layer toward the light emitting layer, It is formed by a compound having such a function. The material of the hole blocking layer also needs to have a wider band gap than the material of the light emitting layer in order to confine excitons generated by recombination in the light emitting layer in the light emitting layer. The band gap in this case is determined from the difference between the oxidation potential and the reduction potential determined electrochemically, or the light absorption edge. The hole blocking layer has a function of confining both charge carriers and excitons in the light emitting layer to improve the light emission efficiency.
[0118]
As a hole blocking layer material satisfying such conditions, a mixed distribution of bis (2-methyl-8-quinolinolato) (phenolato) aluminum, bis (2-methyl-8-quinolinolato) (triphenylsilanolato) aluminum and the like is preferred. Ligand complexes, metal complexes such as bis (2-methyl-8-quinolato) aluminum-μ-oxo-bis- (2-methyl-8-quinolylato) aluminum binuclear metal complexes, styryl compounds such as distyrylbiphenyl derivatives ( JP-A-11-242996), triazole derivatives such as 3- (4-biphenylyl) -4-phenyl-5 (4-tert-butylphenyl) -1,2,4-triazole (JP-A-7-41759). And phenanthroline derivatives such as bathocuproin (JP-A-10-79297).
[0119]
The lower limit of the thickness of the hole blocking layer is usually about 0.1 nm, preferably about 1 nm, and the upper limit is usually about 300 nm, preferably about 100 nm.
[0120]
It is to be noted that the structure opposite to that of FIG. 1, that is, the cathode 7, the light emitting layer 5, the hole transport layer 4, and the anode 2 can be laminated in this order on the substrate 1, and at least one of them is transparent as described above. It is also possible to provide the organic electroluminescent device of the present invention between two substrates having high properties. Similarly, it is also possible to laminate in a structure opposite to the above-mentioned respective layer constitutions shown in FIGS. Further, in addition to the layers shown in FIGS. 1 to 3, an arbitrary layer may be provided between the anode or the cathode and the light emitting layer.
[0121]
The organic electroluminescent device of the present invention is applicable to any of a single organic electroluminescent device, a device having a structure arranged in an array, and a structure in which an anode and a cathode are arranged in an XY matrix. can do.
[0122]
As described above, in the organic electroluminescent device of the present invention, by providing a layer containing the specific anthracene-based compound represented by the general formula (I) as a hole-transporting layer, emission luminance and luminous efficiency are improved. It is possible to provide an organic electroluminescent device excellent in the above.
[0123]
The anthracene compound of the present invention represented by the general formula (I) is basically suitable for use in a hole injecting / transporting layer. The present invention is not limited to this, and can be adopted for any layer provided between the anode and the light emitting layer.
[0124]
【Example】
Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples. However, the present invention is not limited to these Examples as long as the gist is not exceeded. It should be noted that in the following examples, the anthracene-based compound of the present invention was no. Is the No. of the compound in Table 1 above. Corresponding to
[0125]
Example 1: Synthesis of compound (A-1)
8.58 g (26 mmol) of 9,10-diphenylanthracene and 23.13 g (130 mmol) of N-bromosuccinimide were added to 177 ml of N, N-dimethylformamide and reacted at 80 ° C. under nitrogen for 36.5 hours. . After completion of the reaction, the precipitate was separated by filtration, washed with methanol and washed with acetone to obtain 5.18 g of a yellow-brown powdery 2,6-dibromo-9,10-diphenylanthracene represented by the following structural formula ( Yield 41%).
[0126]
Embedded image
[0127]
Mass spec. Of the product MS = 486, melting point = 310 ° C., and 1 From the result of the H-NMR measurement, it was confirmed that the bromine substitution positions were at the 2-position and the 6-position.
[0128]
1 H-NMR (CDCl 3 (Δ = ppm)): 7.37 (dd, 2H), 7.42 (m, 4H), 7.53 (d, 2H), 7.58 (m, 2H), 7.61 (m, 4H) ), 7.82 (d, 2H)
[0129]
1.21 g (2.5 mmol) of the obtained 2,6-dibromo-9,10-diphenylanthracene, 2.01 g (6.0 mmol) of N, N, N′-triphenyl-1,4-phenylenediamine, 0.7 g (7.3 mmol) of sodium tert-butoxide was added to 11 ml of o-xylene, and the mixture was heated to 60 ° C under nitrogen.
[0130]
In it, tris (dibenzylideneacetone) dipalladium (0) -chloroform adduct (Pd 2 (Dba) 3 ・ CHCl 3 ) Was added to 2 ml of an o-xylene solution in which 0.02 g (0.02 mmol) of tert-butyl phosphine was dissolved and 0.17 g (0.8 mmol) of tertiary butyl phosphine, and reacted at 120 ° C for 4 hours.
[0131]
After completion of the reaction, the precipitate was collected, washed with water, and washed with hot acetone, and 0.83 g of vermilion powdered 2,6-bis (N- (4-diphenylamino) phenyl-formula represented by the following structural formula was obtained. N-phenyl) amino-9,10-diphenylanthracene (A-1) was obtained (33% yield). In addition, the obtained solid (powder) showed yellow fluorescence by UV light irradiation.
[0132]
Embedded image
[0133]
The MS of this product was 998, which was consistent with the intended product. In addition, as a result of differential thermal analysis measurement using DSC-20 manufactured by Seiko Denshi Co., Ltd., the glass transition temperature (Tg) showed a high value of 135 ° C. The melting point was 350 ° C and the crystallization temperature was 235 ° C.
[0134]
Next, the glass substrate is subjected to ultrasonic cleaning with acetone, water cleaning with pure water, ultrasonic cleaning with isopropyl alcohol, drying with dry nitrogen, and UV / ozone cleaning. The degree of vacuum is 3 × 10 -6 Evacuation was performed using an oil diffusion pump until the pressure became Torr or less.
[0135]
The anthracene-based compound (A-1) was put in a ceramic crucible, and heated by a tantalum wire heater around the crucible to perform vapor deposition. The degree of vacuum during evaporation is 1.7 × 10 -6 Torr (about 2.3 × 10 -4 At Pa), a uniform and transparent film having a thickness of 91 nm was obtained at a deposition rate of 0.1 to 0.2 nm / sec. The ionization potential of this thin film sample was measured using an ultraviolet electron analyzer (AC-1) manufactured by Riken Keiki Co., Ltd., and showed a low value of 4.95 eV.
[0136]
Example 2: Synthesis of compound (A-2)
Example 1 was repeated except that N, N ′-(1-naphthyl) -N-phenyl-1,4-phenylenediamine was used instead of N, N, N′-triphenyl-1,4-phenylenediamine. The synthesis was performed in the same manner, and vermilion powdery 2,6-bis (((N- (1-naphthyl) -N-phenyl) amino) phenyl-N- (1-naphthyl)) amino represented by the following structural formula was obtained. -9,10-Diphenylanthracene (A-2) was obtained.
[0137]
Embedded image
[0138]
The product, MS = 1198, was in agreement with the intended product. Further, the glass was subjected to differential thermal analysis measurement using DSC-20 manufactured by Seiko Instruments Inc., and as a result, the glass transition temperature (Tg) was as high as 163 ° C. Since this compound (A-2) had a very high amorphous property, no clear melting point was observed.
[0139]
Next, the compound (A-2) was placed in a ceramic crucible in the same manner as in Example 1 to obtain a uniform and transparent film having a thickness of 99 nm. When the ionization potential of this thin film sample was measured, it showed a low value of 4.93 eV.
[0140]
Example 3: Synthesis of compound (A-5)
The procedure was performed except that N, N '-(4-tert-butyl) phenyl-N-phenyl-1,4-phenylenediamine was used instead of N, N, N'-triphenyl-1,4-phenylenediamine. Synthesis was carried out in the same manner as in Example 1, and vermilion powdered 2,6-bis (((N- (4-tert-butyl) phenyl-N-phenyl) amino) phenyl-N- ( 4-tert-butyl) phenyl) amino-9,10-diphenylanthracene (A-5) was obtained.
[0141]
Embedded image
[0142]
The product, MS = 1222, was in agreement with the intended product. In addition, as a result of differential thermal analysis measurement using DSC-20 manufactured by Seiko Denshi, the glass transition temperature (Tg) showed a high value of 160 ° C. Since this compound (A-5) was very amorphous, a clear melting point was not observed.
[0143]
Next, the compound (A-5) was placed in a ceramic crucible in the same manner as in Example 1 to obtain a uniform and transparent film having a thickness of 95 nm. When the ionization potential of this thin film sample was measured, it showed a low value of 4.64 eV.
[0144]
Example 4: Production of organic electroluminescent device
An organic electroluminescent device having the structure shown in FIG. 3 was manufactured by the following method.
A transparent conductive film of indium tin oxide (ITO) deposited on a glass substrate 1 with a thickness of 120 nm (manufactured by Geomatics Co .; electron beam film-formed product; sheet resistance of 15Ω) is 2 mm wide using ordinary photolithography and hydrochloric acid etching. The anode 2 was formed by patterning into a stripe. The patterned ITO substrate was cleaned by ultrasonic cleaning with acetone, water cleaning with pure water, and ultrasonic cleaning with isopropyl alcohol, dried with nitrogen blow, and finally subjected to ultraviolet ozone cleaning.
[0145]
Next, as the anode buffer layer 3, an aromatic diamine-containing polyether ((G-1); a homopolymer; a weight average molecular weight of 25,000; a glass transition temperature of 199 ° C.) comprising the following repeating unit and 10% by weight thereof An amount of the acceptor (J-1) having the following structure was used as a coating solution, and this was spin-coated on the glass substrate, and then dried to form a uniform thin film having a thickness of 30 nm.
[0146]
Embedded image
[0147]
The film forming conditions at this time were as follows.
Solvent Cyclohexanone
Coating solution concentration 13 [mg / ml]
Spinner rotation speed 1500 [rpm]
Spinner rotation time 30 [seconds]
Drying conditions at 100 ° C for 188 minutes
[0148]
Next, the substrate on which the above-mentioned polyether (G-1) was formed was placed in a vacuum evaporation apparatus, and rough evacuation of the apparatus was performed by an oil rotary pump. -6 Evacuation was performed using an oil diffusion pump equipped with a liquid nitrogen trap until the pressure became Torr or less.
[0149]
An anthracene-based compound represented by the following structural formula (A-1) placed in a ceramic crucible disposed in the above apparatus was heated by a Ta wire heater around the crucible and evaporated in a vacuum vessel. The degree of vacuum during evaporation is 1.0 × 10 -6 Torr. Thus, the hole transport layer 4 having a thickness of 40 nm was deposited. The deposition time was 3 minutes and 17 seconds.
[0150]
Embedded image
[0151]
Subsequently, by a similar operation, as a material of the light emitting layer 5, an 8-hydroxyquinoline complex (E-1) of aluminum represented by the following structural formula was heated at a temperature of 274 to 276 ° C. and a degree of vacuum of 0.9 × 10. -6 Torr, vapor deposition at a deposition rate of 0.2 nm / sec for 2 minutes and 59 seconds, and at the same time, rubrene (D-1) having a structure shown below in the light emitting layer 5 in an amount of 2.3 weight of the compound (E-1). The light emitting layer 5 was obtained with a thickness of 30 nm which was uniformly doped in the thickness direction at a concentration of 30%.
[0152]
Embedded image
[0153]
Subsequently, as a material for the electron transport layer 6, an 8-hydroxyquinoline complex of aluminum (E-1) was deposited. At this time, the temperature of the crucible was controlled in the range of 279 to 286 ° C. The degree of vacuum during evaporation is 0.8 × 10 -6 Torr, deposition time was 2 minutes and 35 seconds. As a result, an electron transport layer 6 having a thickness of 30 nm was obtained.
[0154]
The substrate temperature during vacuum deposition of the above-described hole transport layer 4, light-emitting layer 5, and electron transport layer 6 was kept at room temperature.
[0155]
Here, the element on which the electron transport layer 6 has been vapor-deposited is once taken out of the vacuum vapor deposition apparatus into the atmosphere, and a stripe-shaped shadow mask having a width of 2 mm is used as a mask for cathode vapor deposition. And placed in a separate vacuum deposition apparatus so that the degree of vacuum in the apparatus is 2 × 10 -6 Evacuation was performed until the pressure became Torr or less. Subsequently, lithium fluoride was deposited as a cathode interface layer using a molybdenum board so as to have a thickness of 0.3 nm. Vacuum degree at the time of vapor deposition is 6 × 10 -6 Torr.
[0156]
Next, as the cathode 7, aluminum was deposited with a thickness of 100 nm using a molybdenum board. The degree of vacuum during vapor deposition of aluminum is 8.5 × 10 -6 Torr, deposition time was 4 minutes and 39 seconds.
[0157]
As described above, an organic electroluminescent device having a light emitting area of 2 mm × 2 mm was obtained. As a characteristic of this element, 250 mA / cm 2 Brightness at current density of 100 cd / m 2 And the slope of the luminance-current density characteristic was examined.
[0158]
Comparative Example 1
An organic electroluminescent device was prepared in the same manner as in Example 4 except that the following compound (C-1) was used in place of the compound (A-1) in the hole transport layer, and the device characteristics are shown in Table 11. Was.
[0159]
Embedded image
[0160]
[Table 11]
[0161]
As is clear from Table 11, the organic electroluminescent device using the 2,6-arylaminoanthracene-based compound of the present invention has excellent emission luminance, luminous efficiency, and luminance-current density characteristics. On the other hand, when the compound (C-1) is used, the emission luminance, the luminous efficiency, and the luminance-current density characteristics are all less than half that of the case where the compound (A-1) is used, which is very poor. Was something. From this result, even when the same 9,10-diphenylanthracene skeleton was substituted with an arylamino group at the 2,6-position, the compound (C-1) in which the diphenylamino group was simply directly substituted had a positive hole. In contrast to the low transport property and the lack of practicality, the compound (A-1) in which an arylamino group is substituted via an arylamino group at the 2,6-position of the anthracene skeleton has a hole transport property. It can be seen that the light emission luminance, the light emission efficiency, and the luminance-current density characteristics are significantly improved.
[0162]
【The invention's effect】
As described in detail above, the 2,6-arylaminoanthracene-based compound of the present invention has a low ionization potential, a high hole-transport property, and is extremely useful as a charge transport material. In addition, since it can have various substituents, all desired characteristics can be exhibited.
[0163]
Further, in the organic electroluminescent device of the present invention, by using such an anthracene-based compound of the present invention, in terms of luminous efficiency and luminous brightness, performance is superior to a device containing a conventionally known anthracene-based compound. can do.
[Brief description of the drawings]
FIG. 1 is a schematic cross-sectional view showing an example of an embodiment of an organic electroluminescent device of the present invention.
FIG. 2 is a schematic sectional view showing another example of the embodiment of the organic electroluminescent device of the present invention.
FIG. 3 is a schematic sectional view showing another example of the embodiment of the organic electroluminescent device of the present invention.
[Explanation of symbols]
1 substrate
2 Anode
3 Anode buffer layer
4 Hole transport layer
5 Light-emitting layer
6 electron transport layer
7 Cathode

Claims (8)

  1. A 2,6-arylaminoanthracene compound represented by the following general formula (I).
    (In the general formula (I), R 1 to R 6 each independently represent an alkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group, and any of these may have a substituent. Further, R 1 to R 6 may be bonded to each other by adjacent groups or may be bonded to carbon atoms constituting a benzene ring or an anthracene ring in the general formula (I) to form a ring.
    Further, the benzene ring and the anthracene ring in the general formula (I) may have a substituent other than the amino group specified in the formula. )
  2. The 2,6-arylaminoanthracene-based compound according to claim 1, which is represented by the following general formula (II).
    (In the general formula (II), R 1 to R 6 have the same meaning as in the general formula (I). R 7 and R 8 are each independently an alkyl group, an aromatic hydrocarbon group or an aromatic heterocyclic group. And the benzene ring and the anthracene ring in the general formula (II) may be substituted by a substituent other than the amino group, R 7 and R 8 specified in the formula. (It may have a group.)
  3. In the general formula (II), the substituent that the benzene ring and the anthracene ring may have in addition to the amino group, R 7 and R 8 specified in the formula (II) has a halogen atom and a substituent. Alkyl group, alkoxy group optionally having substituent (s), aromatic hydrocarbon group optionally having substituent group, aromatic heterocyclic group optionally having substituent group, and substituent group 3. The 2,6- compound according to claim 2, which is a group selected from aryloxy groups which may have a benzene ring or an anthracene ring in formula (II). Arylaminoanthracene compounds.
  4. The 2,6-arylaminoanthracene compound according to claim 2 or 3, wherein in the general formula (II), R 7 and R 8 are a phenyl group which may have a substituent.
  5. The 2,6-arylaminoanthracene compound according to any one of claims 1 to 4, wherein the ionization potential is 5.3 eV or less.
  6. A charge transport material comprising the 2,6-arylaminoanthracene compound according to claim 1.
  7. In an organic electroluminescent element having a pair of electrodes and an organic light emitting layer provided between both electrodes on a substrate, as the organic light emitting layer, and / or as a layer provided between the organic light emitting layer and the electrode, An organic electroluminescent device comprising a layer containing the 2,6-arylaminoanthracene-based compound according to any one of claims 1 to 5.
  8. The organic electroluminescent device according to claim 7, wherein a layer containing the 2,6-arylaminoanthracene-based compound according to any one of claims 1 to 5 is provided between an anode and an organic light emitting layer.
JP2002251263A 2002-08-29 2002-08-29 2,6-arylaminoanthracene compound, charge transport material, and organic electroluminescent element Pending JP2004091334A (en)

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