JP2009246097A - Organic electroluminescence device, display device, and illuminating device - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescence device providing a high light-emitting luminance, having a longer operating life and a low driving voltage, and also to provide an illuminating device and a display device, using the device. <P>SOLUTION: The organic electroluminescence device comprises at least one type of compound expressed by a general expression (1). In the general expression, the Z expresses n linking group or a mere coupling hand. A is a group expressed by the general expression (A1). The n expresses an integer of 2 to 6. The X<SB>11</SB>and X<SB>12</SB>express nitrogen atom or -CR<SB>11</SB>, however at least one of them is a nitrogen atom. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to an organic electroluminescence (hereinafter also abbreviated as organic EL) element, a display device using the same, and a lighting device, and more specifically, an organic electroluminescence element excellent in emission luminance and a display using the same. Device, lighting device.

  As a light-emitting electronic display device, there is an electroluminescence display (ELD). As a component of ELD, an inorganic electroluminescent element and an organic electroluminescent element are mentioned. Inorganic electroluminescent elements have been used as planar light sources, but an alternating high voltage is required to drive the light emitting elements. An organic electroluminescence device has a structure in which a light-emitting layer containing a light-emitting compound is sandwiched between a cathode and an anode, and excitons (excitons) are generated by injecting electrons and holes into the light-emitting layer and recombining them. The device emits light by utilizing the emission of light (fluorescence / phosphorescence) when the exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts. Therefore, it has a wide viewing angle, high visibility, and since it is a thin-film type completely solid element, it has attracted attention from the viewpoints of space saving and portability.

  However, for organic EL elements for practical use in the future, development of organic EL elements that emit light efficiently and with high brightness with further low power consumption is desired.

  Various organic EL elements have been reported so far. For example, Appl. Phys. Lett. , Vol. 51, 913, or a combination of a hole injection layer described in JP-A-59-194393 and an organic light-emitting layer, and a hole injection layer described in JP-A-63-295695 and electron injection A combination with a transport layer, Jpn. Journal of Applied Physics, vol. 127, no. 2, 269-271, a combination of a hole transport layer, a light emitting layer, and an electron transport layer is disclosed. However, a device with higher luminance is demanded, and further improvement in energy conversion efficiency and light emission quantum efficiency is expected.

  In addition, a problem that the light emission life is short has been pointed out. The cause of such deterioration in luminance over time has not been fully elucidated, but electroluminescent devices that emit light are decomposed by the organic compounds themselves that constitute the thin film due to the light emitted by itself and the heat generated at that time. Factors derived from organic compounds that are organic EL element materials, such as crystallization of organic compounds, have also been pointed out.

  In addition, no useful high-performance electron transport material that can withstand practical use has been found. For example, a research group at Kyushu University has obtained 2- (4-biphenyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole (t-BuPBD), which is an oxadiazole derivative. First, 1,3-bis (4-tert-butylphenyl-1,3,4-oxadizolyl) biphenylene (OXD-1), 1,3-bis, which is an oxadiazole dimer derivative with improved thin film stability (4-t-butylphenyl-1,3,4-oxadizolyl) phenylene (OXD-7) (Jpn. J. Appl. Phys. Vol. 31 (1992), p. 1812) has been proposed. In addition, a research group at Yamagata University has produced a white light-emitting element by using a triazole electron transport material having excellent electron blocking properties (Science, 3 March 1995, Vol. 267, p. 1332). Further, JP-A-5-331459 describes that phenanthroline derivatives are useful as electron transport materials.

  However, the conventional electron transporting material has a low thin film forming ability and is easily crystallized, so that there is a problem that the light emitting element is destroyed. As organic electroluminescent materials for solving these problems, compounds disclosed in JP-A-9-87616, JP-A-9-194487, and JP-A-2000-186094 include compounds containing silicon atoms in the molecule as luminescent materials or electrons. Although the example used as a transport material is described, it was not enough about coexistence of luminous efficiency and luminous lifetime.

  On the other hand, a technique has been reported in which the luminous efficiency is improved by constituting the light emitting layer with a host compound and a small amount of phosphor. For example, in Japanese Patent No. 3093796, a small amount of a phosphor is doped into a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative to achieve improvement in light emission luminance and a longer device lifetime. An 8-hydroxyquinoline aluminum complex as a host compound, a device having an organic light-emitting layer doped with a small amount of phosphor (Japanese Patent Laid-Open No. 63-264692), an 8-hydroxyquinoline aluminum complex as a host compound, An element having an organic light emitting layer doped with a quinacridone dye (Japanese Patent Laid-Open No. 3-255190) is known. As described above, the emission luminance is improved by doping a phosphor having a high fluorescence quantum yield as compared with the conventional device.

  However, the light emission from the small amount of the phosphor to be doped is light emission from the excited singlet, and when the light emission from the excited singlet is used, the generation ratio of the singlet exciton and the triplet exciton is 1: 3, the generation probability of the luminescent excited species is 25%, and the light extraction efficiency is about 20%. Therefore, the limit of the external extraction quantum efficiency (η) is 5%.

  However, since the University of Princeton reported an organic EL device using phosphorescence emission from an excited triplet (MA Baldo et al., Nature, 395, 151-154 (1998)), In recent years, research on phosphorescent materials has been actively conducted (for example, MA Baldo et al., Nature, 403, 17, 750-753 (2000), US Pat. No. 6,097). No. 147, etc.). When the excitation triplet is used, the upper limit of the internal quantum efficiency is 100%. In principle, the emission efficiency is up to four times that of the excitation singlet, and the performance is almost the same as that of a cold cathode tube. It can be applied to and attracts attention.

  For example, S.M. Lamansky et al. , J .; Am. Chem. Soc. , 123, 4304 (2001), etc., many compounds are being studied for synthesis centering on heavy metal complexes such as iridium complexes. In addition, the aforementioned M.I. A. Baldo et al. , Nature, 403, 17, 750-753 (2000), studies have been made using tris (2-phenylpyridine) iridium as a dopant.

  Ortho-metalated complexes with platinum instead of iridium as the central metal are also attracting attention. With respect to this type of complex, many examples are known in which ligands are characterized.

  Of course, the host when using the phosphorescent compound as a dopant needs to have an emission maximum wavelength in a region shorter than the emission maximum wavelength of the phosphorescent compound. I know that there is. Host compound of phosphorescent compound: C.I. Adachi et al. , Appl. Phys. Lett. , 77, 904 (2000), etc., but a new approach is necessary for the properties required for the host compound in order to obtain a high-brightness organic electroluminescence device. . As host compounds of these phosphorescent dopants, carbazole derivatives represented by CBP and m-CP are well known (for example, see Patent Documents 1 and 2). In particular, as a blue light emitting host compound, m-CP having a large band gap and derivatives thereof are known.

  On the other hand, a technique for obtaining high emission luminance by introducing a hole blocking layer (exciton blocking layer) is also disclosed. An example of using a certain type of aluminum complex and high efficiency emission by using a fluorine-substituted compound. (For example, refer to Patent Document 3 and Non-Patent Document 1).

Examples in which a pyridine derivative or a pyrimidine derivative is used as an electron transport material are disclosed (for example, see Patent Documents 4 and 5). Moreover, the example which uses a pyridine derivative for an electron transport material is disclosed (for example, refer patent document 6, 7, 8).
International Publication No. 03/80760 Pamphlet WO04 / 74399 pamphlet Japanese Patent Laid-Open No. 2002-8860 International Publication No. 06/103909 Pamphlet JP 2003-45662 A JP-A-4-68076 US Pat. No. 5,077,142 Japanese Patent No. 3925265 Appl. Phys. Lett. 79, 156 (2001)

  Therefore, the present invention has been made for the purpose of achieving both improvement in light emission luminance and durability of the device using a nitrogen-containing heterocyclic compound having a specific structure, and the present invention uses the compound for phosphorescence emission. By using the compound as a host compound, or by using the compound as an electron transport material (hole blocker), an organic electroluminescence device that achieves both improvement in emission luminance and durability, and high emission luminance and long time using the organic electroluminescence device. The present invention provides a display device and a lighting device that have a long life and low driving voltage.

  The above object of the present invention has been achieved by the following constitution.

  1. An organic electroluminescence device comprising at least one compound represented by the following general formula (1).

(In the formula, Z represents an n-valent linking group or a simple bond, and A represents a group represented by the general formula (A1). N represents an integer of 2 or more and 6 or less. In the general formula (A1), , Ar represents an arylene group, R _{1 to} R ₆ each represent a hydrogen atom or a substituent, and X ₁₁ and X ₁₂ represent a nitrogen atom or —CR _11, and at least one of X ₁₁ and X ₁₂ R ₁₁ represents a hydrogen atom or a substituent, and among R _{1 to} R ₆ and R ₁₁ , adjacent substituents may be condensed with each other to form a ring.
2. 2. The organic electroluminescence device according to 1 above, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).

(In the formula, A represents the general formula (A1), Z1 represents the following, and n represents an integer of 2 or more and 6 or less.)

(In Z1, at least two of Ra to Re are substituents represented by the general formula (A1), and the plurality of substituents may be the same or different. Of Ra to Re, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent, and adjacent substituents may be condensed with each other to form a ring.)
3. 2. The organic electroluminescence device according to 1 above, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (3).

(In the formula, A represents the general formula (A1), Z2 represents the following, and n represents an integer of 2 or more and 6 or less.)

(In Z2, at least two of Ra to Rf are substituents represented by the general formula (A1), and the plurality of substituents may be the same or different. Of Ra to Rf, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent, and adjacent substituents may be condensed with each other to form a ring.)
4). 2. The organic electroluminescent device according to 1 above, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (4).

(In the formula, A represents the general formula (A1), Z3 represents the following, and n represents an integer of 2 or more and 6 or less.)

(In Z3, at least two of Ra to Rf are substituents represented by the general formula (A1), and the plurality of substituents may be the same or different. Of Ra to Rf, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent, and adjacent substituents may be condensed with each other to form a ring.)
5. 2. The organic electroluminescence device according to 1 above, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (5).

(In the formula, A represents the general formula (A1), Z4 represents the following, and n represents 2 or 3.)

(In Z4, at least two of Ra to Rc are substituents represented by the general formula (A1), and the plurality of substituents may be the same or different. Of Ra to Rc, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent.)
6). 2. The organic electroluminescence device according to 1 above, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (6).

(In the formula, A represents the general formula (A1), Z5 represents the following, and n represents 2 or 3.)

(In Z5, at least two of Ra to Rc are substituents represented by the general formula (A1), and the plurality of substituents may be the same or different. Of Ra to Rc, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent.)
7). 2. The organic electroluminescence device according to 1 above, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (7).

(In the formula, A represents the general formula (A1), Z6 represents the following, and n represents 3 or 4.)

(In Z6, at least two of Ra to Rd are substituents represented by formula (A1), and the plurality of substituents may be the same or different. Of Ra to Rd, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent, and adjacent substituents may be condensed with each other to form a ring.)
8). 2. The organic electroluminescence device according to 1 above, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (8).

(In the formula, Ar ₁ represents an n-valent arylene group, and R _{1 to} R ₆ each represents a hydrogen atom or a substituent. X ₁₁ and X ₁₂ represent a nitrogen atom or —CR ₁₁ , but X ₁₁ , X ₁₂ At least one of them is a nitrogen atom, R ₁₁ represents a hydrogen atom or a substituent, n represents an integer of 2 to 6. Among R _{1 to} R ₆ and R ₁₁ , adjacent substituents May be condensed with each other to form a ring.)
9. An electron transport layer contains at least one compound selected from the compounds represented by the general formulas (1) to (8).

  10. The light emitting layer contains at least one compound selected from the compounds represented by the general formulas (1) to (8).

  11. In the organic electroluminescence device having a light emitting layer containing a host compound and a phosphorescent compound, the host compound is at least one compound selected from the compounds represented by the general formulas (1) to (8). An organic electroluminescence device characterized by the above.

  12 12. The organic electroluminescence device as described in 11 above, wherein the phosphorescent compound is an iridium compound, an osmium compound or a platinum compound.

  13. 13. The organic electroluminescence device as described in 12 above, wherein the phosphorescent compound is an iridium compound.

  14 14. The organic electroluminescence device as described in any one of 1 to 13 above, wherein the organic layer is formed by a wet process.

  15. A display device comprising the organic electroluminescence element according to any one of 1 to 14 above.

  16. 15. An illumination device comprising the organic electroluminescence element according to any one of 1 to 14 above.

  According to the present invention, it was possible to provide an organic electroluminescence element that exhibits high emission luminance, has a long lifetime, and has a low driving voltage, and an illumination device and a display device using the element.

  Hereinafter, the present invention will be described in detail.

  As a result of intensive studies, the present inventors have used at least one of the compounds represented by the general formulas (1) to (8), thereby exhibiting a high emission luminance and a highly durable organic electroluminescence element ( It was also found that an organic EL element) and a lighting device and a display device having the organic EL element can be provided. In addition, it was found that a highly efficient full-color image display device can be obtained by combining the above compounds.

  The organic EL element of the present invention includes at least one compound represented by the general formulas (1) to (8) in at least one layer constituting the organic EL element. Although it is an indispensable requirement for obtaining the described effect, it is preferable to include the above-mentioned compound in the light emitting layer, the hole blocking layer or the electron transporting layer.

  Nitrogen-containing heterocyclic derivatives typified by pyridine, pyrimidine, and triazine are known as electron transport materials, and their molecular structure is changed into a specific form represented by general formulas (1) to (8) of the present invention. In addition, it has been found that the performance of a conventional device can be greatly improved by introducing a heterocyclic group containing at least two nitrogen atoms at specific positions. This is presumably because the introduction of two or more nitrogen atoms lowered the potential of the whole molecule and optimized the carrier balance.

  Hereinafter, details of each component according to the present invention will be sequentially described.

  Here, the compounds represented by the general formulas (1) to (8) according to the present invention will be described. In the general formula (1), the n-valent linking group represented by Z is not particularly limited, but is preferably a linking group represented by Z1 to Z6 in the general formulas (2) to (8).

A is represented by the general formula (A1), and a plurality of A may be the same as or different from each other. X ₁₁ and X ₁₂ represent a nitrogen atom or CR _11, and at least one of X ₁₁ and X ₁₂ is a nitrogen atom, but one of X ₁₁ and X ₁₂ is a nitrogen atom Is preferred. R ₁₁ represents a hydrogen atom or a substituent, and when R ₁₁ represents a substituent, it is synonymous with R _{1 to} R _{6 in} the general formula (1).

  In the general formulas (1) to (4) and (8), n represents an integer of 2 to 6, and in the general formulas (5) and (6), n represents 2 or 3, and the general formula (7) In the above, n represents 3 or 4.

In the general formula (1), R _{1 to} R ₆ each represent a hydrogen atom or a substituent, and examples of the substituent include an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, t-butyl group). Group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (for example, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (for example, vinyl group, allyl group, etc.) ), Alkynyl group (for example, ethynyl group, propargyl group, etc.), aromatic hydrocarbon ring group (aromatic carbocyclic group, aryl group, etc., for example, phenyl group, p-chlorophenyl group, mesityl group, tolyl group, Xylyl, naphthyl, anthryl, azulenyl, acenaphthenyl, fluorenyl, phenanthryl, For example, pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, imidazolyl group, benzoimidazolyl group, pyrazolyl group, pyrazinyl group, triazolyl group (for example, 1, 2,4-triazol-1-yl group, 1,2,3-triazol-1-yl group, etc.), oxazolyl group, benzoxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, furazanyl group, thienyl group, A quinolyl group, a benzofuryl group, a dibenzofuryl group, a benzothienyl group, a dibenzothienyl group, an indolyl group, a carbazolyl group, a carbolinyl group, a diazacarbazolyl group (one of the carbon atoms constituting the carboline ring of the carbolinyl group is a nitrogen atom) ), Quinoxalinyl group, Pyridazinyl group, triazinyl group, quinazolinyl group, phthalazinyl group, etc.), heterocyclic group (eg, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.), alkoxy group (eg, methoxy group, ethoxy group, propyloxy group, pentyl) Oxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxy group (eg, cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group (eg, phenoxy group, naphthyloxy group, etc.), alkylthio group (Eg, methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group ( For example, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (eg, methyloxycarbonyl group, ethyloxycarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (eg, Phenyloxycarbonyl group, naphthyloxycarbonyl group, etc.), sulfamoyl group (for example, aminosulfonyl group, methylaminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octylaminosulfonyl group) , Dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2-pyridylaminosulfonyl group, etc.), acyl group (for example, Til group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group, cyclohexylcarbonyl group, octylcarbonyl group, 2-ethylhexylcarbonyl group, dodecylcarbonyl group, phenylcarbonyl group, naphthylcarbonyl group, pyridylcarbonyl group, etc.), acyloxy group ( For example, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.), amide group (for example, methylcarbonylamino group, ethylcarbonylamino group, dimethylcarbonyl) Amino group, propylcarbonylamino group, pentylcarbonylamino group, cyclohexylcarbonylamino group, 2-ethylhexylcarbonylamino group, octylcal Bonylamino group, dodecylcarbonylamino group, phenylcarbonylamino group, naphthylcarbonylamino group, etc.), carbamoyl group (for example, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexyl) Aminocarbonyl group, octylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, dodecylaminocarbonyl group, phenylaminocarbonyl group, naphthylaminocarbonyl group, 2-pyridylaminocarbonyl group, etc.), ureido group (for example, methylureido group, ethylureido) Group, pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenylureido group, naphthylureido group, 2-pi Dilaminoureido group, etc.), sulfinyl group (for example, methylsulfinyl group, ethylsulfinyl group, butylsulfinyl group, cyclohexylsulfinyl group, 2-ethylhexylsulfinyl group, dodecylsulfinyl group, phenylsulfinyl group, naphthylsulfinyl group, 2-pyridylsulfinyl group) Group), alkylsulfonyl group (for example, methylsulfonyl group, ethylsulfonyl group, butylsulfonyl group, cyclohexylsulfonyl group, 2-ethylhexylsulfonyl group, dodecylsulfonyl group, etc.), arylsulfonyl group or heteroarylsulfonyl group (for example, phenyl) Sulfonyl group, naphthylsulfonyl group, 2-pyridylsulfonyl group, etc.), amino group (for example, amino group, ethylamino group, dimethylamino group, butyl) Mino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, anilino group, naphthylamino group, 2-pyridylamino group, etc.), halogen atom (eg, fluorine atom, chlorine atom, bromine atom), fluorinated carbonization Hydrogen group (for example, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyano group, nitro group, hydroxy group, mercapto group, silyl group (for example, trimethylsilyl group, triisopropylsilyl group) , Triphenylsilyl group, phenyldiethylsilyl group, etc.). These substituents may be further substituted with the above substituents, and adjacent substituents may be condensed with each other to form a ring.

  Among these substituents, an alkyl group, an aromatic hydrocarbon ring group, and an aromatic heterocyclic group are preferable.

In the general formulas (2) to (7), Ra to Rf each represent a hydrogen atom or a substituent, and specific examples thereof have the same meanings as R _{1 to} R ₆ .

  In the general formulas (1) to (7), the arylene group represented by Ar is a residue obtained by removing two hydrogen atoms or substituents from an arbitrary position of an arbitrary aromatic compound, and the arylene group May be composed of a hydrocarbon, a heterocycle containing a heteroatom, or a condensed ring.

  In the general formula (8), the n-valent arylene group represented by Ar1 is a residue obtained by removing n hydrogen atoms or substituents from any position of any aromatic compound, and the arylene group is It may be composed of a hydrocarbon, a heterocycle containing a heteroatom, or may be condensed.

  Each compound according to the present invention represented by the general formulas (1) to (8) is a compound having strong fluorescence in a solid state, is excellent in electroluminescence, and can be effectively used as a light emitting material. In addition, since the excellent electron injecting property and electron transporting property from the metal electrode are very excellent, in the device using another light emitting material or the above compound according to the present invention as a light emitting material, the compound according to the present invention is an electron. When used as a transport material or hole blocker, it exhibits excellent luminous efficiency.

  Specific examples of the compounds represented by the general formulas (1) to (8) are listed below, but the present invention is not limited to these.

  The above compound according to the present invention can be easily synthesized according to a known synthesis method, but can be more easily synthesized by the synthesis route shown below.

  The above reaction is described in Organic Letter, Vol. 3, No. 16, p 2579-2581 (2001).

  In addition, as a result of extensive studies on the host compound of the phosphorescent compound, the present inventors have produced an organic electroluminescence device using the phenylpyrimidine compound and the phenyltriazine compound according to the present invention as the host compound. The present inventors have found that the light emission luminance and lifetime of the device and the driving voltage are improved.

  The host compound used in the present invention will be described. Here, the host compound in the present invention is a phosphorescent quantum yield of phosphorescence emission at a room temperature (25 ° C.) having a mass ratio of 20% or more in the compound contained in the light emitting layer. Is defined as a compound with less than 0.1. The phosphorescence quantum yield is preferably less than 0.01. Moreover, it is preferable that the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.

  As the host compound, known host compounds may be used alone or in combination of two or more. By using a plurality of types of host compounds, it is possible to adjust the movement of charges, and the efficiency of the organic EL element can be increased. Moreover, it becomes possible to mix different light emission by using multiple types of light emission dopants mentioned later, and, thereby, arbitrary luminescent colors can be obtained.

  Moreover, as a light emission host used for this invention, the compound represented by General formula (1)-(8) is used preferably. Moreover, you may use together a conventionally well-known light emission dopant as shown below. A conventionally known low molecular compound or a polymer compound having a repeating unit may be used, or a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (evaporation polymerizable light-emitting host) may be used. As known host compounds that may be used in combination with the present invention, there are compounds having a hole transporting ability and an electron transporting ability, preventing the emission of longer wavelengths, and having a high Tg (glass transition temperature). preferable.

  Specific examples of host compounds that can be used in combination with the present invention are shown below, but the present invention is not limited thereto.

  As the electron transport material (hole blocking material) used in the present invention, compounds represented by the general formulas (1) to (8) are preferably used.

  The phosphorescent compound according to the present invention is a compound in which light emission from an excited triplet is observed, and is a compound having a phosphorescence quantum yield of 0.001 or more at 25 ° C. Preferably it is 0.01 or more. More preferably, it is 0.1 or more.

  The phosphorescence quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of Experimental Chemistry Course 4 of the 4th edition. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence quantum yield used in the present invention is only required to achieve the phosphorescence quantum yield in any solvent.

  Preferably, it is a complex compound containing a Group VIII metal in the periodic table of elements, more preferably an iridium, onium, or platinum complex compound, and more preferably an iridium complex compound.

  Specific examples of the phosphorescent compound used in the present invention are shown below, but are not limited thereto. These compounds are described, for example, in Inorg. Chem. 40, 1704-1711, and the like.

  Furthermore, the following compounds are also used in the present invention.

  In another embodiment, in addition to the host compound and the phosphorescent compound, at least one fluorescent compound having a fluorescence maximum wavelength is contained in a region longer than the maximum wavelength of light emission from the phosphorescent compound. There is also. In this case, electroluminescence as an organic EL element can be emitted from the fluorescent compound by energy transfer from the host compound and the phosphorescent compound. Preferred as the fluorescent compound is one having a high fluorescence quantum yield in a solution state.

  Here, the fluorescence quantum yield is preferably 0.1 or more, particularly preferably 0.3 or more. Specifically, coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes, stilbene dyes , Polythiophene dyes, or rare earth complex phosphors. The fluorescence quantum yield mentioned here can also be measured by the method described in Spectra II, page 362 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7.

  Hereinafter, components of the organic electroluminescence element of the present invention will be described.

  In the present invention, preferred specific examples of the layer structure of the organic EL element are shown below, but the present invention is not limited thereto.

(I) Anode / light emitting layer / electron transport layer / cathode (ii) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (iii) Anode / hole transport layer / light emitting layer / hole blocking layer / electron Transport layer / cathode (iv) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode (v) Anode / anode buffer layer / hole transport layer / light emitting layer / hole Blocking layer / electron transport layer / cathode buffer layer / cathode As the anode in the organic EL device, a material having a high work function (4 eV or more) metal, alloy, electrically conductive compound and a mixture thereof is preferably used. . Specific examples of such electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO ₂ and ZnO. Alternatively, an amorphous material such as IDIXO (In ₂ O ₃ —ZnO) capable of forming a transparent conductive film may be used.

  For the anode, a thin film may be formed by depositing these electrode materials by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by photolithography, or when the pattern accuracy is not so high (about 100 μm or more) ), A pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. When light emission is extracted from the anode, it is desirable that the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred Ω / □ or less. Further, although the film thickness depends on the material, it is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.

On the other hand, as the cathode, a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.

Among these, a mixture of an electron injecting metal and a second metal, which is a stable metal having a larger work function value than this, from the point of durability against electron injection and oxidation, for example, a magnesium / silver mixture, Suitable are a magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al ₂ O ₃ ) mixture, a lithium / aluminum mixture, aluminum and the like.

  The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually selected in the range of 10 to 1000 nm, preferably 50 to 200 nm. In order to transmit light, if either one of the anode or the cathode of the organic EL element is transparent or translucent, the light emission luminance is improved, which is convenient.

  Next, an injection layer, a hole transport layer, an electron transport layer, a light emitting layer, and the like will be described.

  The injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, and as described above, it exists between the anode and the light emitting layer or the hole transport layer and between the cathode and the light emitting layer or the electron transport layer. May be.

  An injection layer is a layer provided between an electrode and an organic layer in order to reduce driving voltage and improve light emission luminance. “Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166) in detail, and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).

  The details of the anode buffer layer (hole injection layer) are described in JP-A Nos. 9-45479, 9-260062, and 8-288069. Specific examples thereof include copper phthalocyanine. Examples thereof include a phthalocyanine buffer layer represented by an oxide, an oxide buffer layer represented by vanadium oxide, an amorphous carbon buffer layer, and a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.

  Details of the cathode buffer layer (electron injection layer) are also described in JP-A-6-325871, 9-17574, 10-74586, and the like. Specifically, strontium, aluminum, etc. Metal buffer layer typified by lithium, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer layer typified by aluminum oxide, etc. .

  The buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 to 100 nm, although it depends on the material.

  As described above, the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film. For example, it is described in JP-A Nos. 11-204258 and 11-204359, page 237 of “Organic EL elements and the forefront of industrialization (issued on November 30, 1998 by NTS Corporation)”, and the like. There is a hole blocking (hole blocking) layer.

  The hole blocking layer is an electron transporting layer in a broad sense, and is made of a material that has a function of transporting electrons and has a very small ability to transport holes. By blocking holes while transporting electrons, The recombination probability of holes can be improved.

  On the other hand, the electron blocking layer is a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has a very small ability to transport electrons, and blocks electrons while transporting holes. The recombination probability of electrons and holes can be improved.

  The hole transport layer is made of a material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer.

  The hole transport layer and the electron transport layer can be provided as a single layer or a plurality of layers.

  The light emitting layer is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is adjacent to the light emitting layer even in the light emitting layer. It may be an interface with the layer.

  The material used for the light emitting layer (hereinafter referred to as the light emitting material) is preferably an organic compound or complex that emits fluorescence or phosphorescence, and is appropriately selected from known materials used for the light emitting layer of the organic EL device. Can be used. Such a light-emitting material is mainly an organic compound, and may have a desired color tone, for example, Macromol. Synth. 125, pages 17 to 25, and the like.

  The light emitting material may have a hole transporting function and an electron transporting function in addition to the light emitting performance, and most of the hole transporting material and the electron transporting material can be used as the light emitting material. The light emitting material may be a polymer material such as p-polyphenylene vinylene or polyfluorene, and a polymer material in which the light emitting material is introduced into a polymer chain or the light emitting material is a polymer main chain is used. May be.

  This light emitting layer can be formed by forming the above compound by a known thinning method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. Although the film thickness as a light emitting layer does not have a restriction | limiting in particular, Usually, it selects in 5 nm-5 micrometers. The light emitting layer may have a single layer structure composed of one or more of these light emitting materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions. In a preferred embodiment of the organic EL device of the present invention, the light emitting layer is composed of two or more materials, and at least one of them is the compound according to the present invention.

  Further, as described in JP-A-57-51781, this light-emitting layer is prepared by dissolving the above light-emitting material in a solvent together with a binder such as a resin, and then using a spin coat method or the like. It can be formed as a thin film. There is no restriction | limiting in particular about the film thickness of the light emitting layer formed in this way, Although it can select suitably according to a condition, Usually, it is the range of 5 nm-5 micrometers.

  As described above, when there are two or more materials for the light emitting layer, the main component is called a host, and the other components are called dopants. The mixing ratio of the dopant is preferably 0.1% or more and less than 15% by mass ratio.

  The host compound of the light emitting layer is preferably an organic compound or a complex, and in the present invention, preferably the fluorescence maximum wavelength is shorter than the dopant. As the host compound, any of known materials used in organic EL devices can be selected and used, and most of the hole transport materials and electron transport materials described below are also used as the light emitting layer host compound. it can.

  A polymer material such as polyvinyl carbazole or polyfluorene may be used, and a polymer material in which the host compound is introduced into a polymer chain or the host compound is used as a polymer main chain may be used. As the host compound, a compound having a hole transport ability and an electron transport ability and a high Tg (glass transition temperature) is preferable.

  The hole transport layer is made of a material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer. The hole transport layer can be provided as a single layer or a plurality of layers.

  There are no particular restrictions on the hole transport material, and conventionally known photoconductive materials are commonly used as hole charge injection and transport materials, and well-known materials used for hole injection layers and hole transport layers of EL devices. Any one can be selected and used.

  The hole transport material has one of hole injection or transport and electron barrier properties, and may be either organic or inorganic. For example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.

  The above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.

  Representative examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl; N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminophenyl) phenylmethane; N, N'-diphenyl-N, N ' − (4-methoxyphenyl) -4,4'-diaminobiphenyl; N, N, N ', N'-tetraphenyl-4,4'-diaminodiphenyl ether; 4,4'-bis (diphenylamino) quadriphenyl; N, N, N-tri (p-tolyl) amine; 4- (di-p-tolylamino) -4 '-[4- (di-p-tolylamino) styryl] stilbene; 4-N, N-diphenylamino- (2-diphenylvinyl) benzene; 3-methoxy-4′-N, N-diphenylaminostilbenzene; N-phenylcarbazole, and also two of those described in US Pat. No. 5,061,569. Having a condensed aromatic ring in the molecule, for example, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), JP-A-4-3086 4,4 ', 4 "-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 8 are linked in a starburst type ( MTDATA) and the like.

  Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used. In addition, inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.

  In the present invention, the hole transport material for the hole transport layer is preferably a compound having a shorter fluorescence maximum wavelength and a higher Tg than the compound used for the light emitting layer.

  This hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. Although there is no restriction | limiting in particular about the film thickness of a positive hole transport layer, Usually, it is about 5-5000 nm. This hole transport layer may have a single layer structure composed of one or more of the above materials.

  The electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer. The electron transport layer can be provided as a single layer or a plurality of layers. Furthermore, the electron transport layer used as necessary only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer, and as the material, an arbitrary material is selected from conventionally known compounds. Can be used.

  Examples of materials used for the electron transport layer (hereinafter referred to as electron transport materials) include heterocyclic tetracarboxylic acid anhydrides such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, carbodiimides, and the like. , Fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives and the like. Furthermore, in the above oxadiazole derivative, a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.

  Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.

  In addition, metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum. Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and the like, and the central metals of these metal complexes are In, Mg, Metal complexes replaced with Cu, Ca, Sn, Ga or Pb can also be used as the electron transport material.

  In addition, metal-free or metal phthalocyanine, or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material. In addition, the distyrylpyrazine derivative exemplified as the material of the light emitting layer can also be used as an electron transport material, and similarly to the hole injection layer and the hole transport layer, inorganic such as n-type-Si and n-type-SiC can be used. A semiconductor can also be used as an electron transport material.

  Similarly to the compound used for the hole transport layer, the compound used for the electron transport layer is preferably a compound having a shorter fluorescence maximum wavelength and a higher Tg than the compound used for the light emitting layer.

  The substrate related to the organic EL device of the present invention is not particularly limited in the type of glass, plastic, etc., and is not particularly limited as long as it is transparent. Examples of the substrate preferably used include glass and quartz. And a light transmissive resin film. A particularly preferable substrate is a resin film that can give flexibility to the organic EL element.

  Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), and cellulose. Examples include films made of triacetate (TAC), cellulose acetate propionate (CAP), and the like.

An inorganic or organic film or a hybrid film of both may be formed on the surface of the resin film, and it is preferably a high barrier film having a water vapor transmission rate of 0.01 g / m ² · day or less.

  The external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 2% or more. Here, the external extraction quantum efficiency (%) = the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element × 100.

  Further, a hue improving filter such as a color filter may be used in combination.

  When used in lighting applications, a film (such as an antiglare film) that has been roughened to reduce unevenness in light emission can be used in combination.

  When used as a multicolor display device, it is composed of at least two types of organic EL elements having different light emission maximum wavelengths. A suitable example for producing an organic EL element will be described.

  As an example of the method for producing the organic EL device of the present invention, a method for producing an organic EL device comprising an anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode. Will be described.

  First, a thin film made of a desired electrode material, for example, an anode material, is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 μm or less, preferably 10 to 200 nm, thereby producing an anode. To do. Next, a thin film containing an organic compound such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, or an electron transport layer, which is an element material, is formed thereon.

As a method for thinning a thin film containing an organic compound, there are a spin coating method, a casting method, an ink jet method, a vapor deposition method, a printing method, and the like, but a homogeneous film is easily obtained and pinholes are not easily generated. In view of the above, the vacuum deposition method or the spin coating method is particularly preferable. Further, a different film forming method may be applied for each layer. When employing a vapor deposition method for film formation, the vapor deposition conditions vary depending on the type of compound used, but generally a boat heating temperature of 50 to 450 ° C., a degree of vacuum of 10 ⁻⁶ to 10 ⁻² Pa, and a vapor deposition rate of 0.01 to It is desirable to select appropriately within the range of 50 nm / second, substrate temperature of −50 to 300 ° C., and film thickness of 0.1 to 5 μm.

  After these layers are formed, a thin film made of a cathode material is formed thereon by a method such as vapor deposition or sputtering so as to have a film thickness of 1 μm or less, preferably in the range of 50 to 200 nm, and a cathode is provided. Thus, a desired organic EL element can be obtained. The organic EL element is preferably produced from the hole injection layer to the cathode consistently by a single evacuation, but may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.

  The display device of the present invention will be described. The display device of the present invention has the organic EL element.

  Although the display device of the present invention may be single color or multicolor, the multicolor display device will be described here. In the case of a multicolor display device, a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by vapor deposition, casting, spin coating, ink jet, printing, or the like.

  When patterning is performed only on the light-emitting layer, the method is not limited, but a vapor deposition method, an inkjet method, and a printing method are preferable. In the case of using a vapor deposition method, patterning using a shadow mask is preferable.

  Moreover, it is also possible to reverse the production order and produce the cathode, the electron transport layer, the hole blocking layer, the light emitting layer, the hole transport layer, and the anode in this order.

  When a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode. Further, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the-state. The alternating current waveform to be applied may be arbitrary.

  The multicolor display device can be used as a display device, a display, and various light emission sources. In a display device or display, full-color display is possible by using three types of organic EL elements of blue, red, and green light emission.

  Examples of the display device and display include a television, a personal computer, a mobile device, an AV device, a character broadcast display, and an information display in an automobile. In particular, it may be used as a display device for reproducing still images and moving images, and the driving method when used as a display device for reproducing moving images may be either a simple matrix (passive matrix) method or an active matrix method.

  Light emitting sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, light sources for optical sensors, etc. However, it is not limited to this.

  The lighting device of the present invention will be described. The illuminating device of this invention has the said organic EL element.

  The organic EL element of the present invention may be used as an organic EL element having a resonator structure. The purpose of use of the organic EL element having such a resonator structure is as follows. The light source of a machine, the light source of an optical communication processing machine, the light source of a photosensor, etc. are mentioned, However It is not limited to these. Moreover, you may use for the said use by making a laser oscillation.

  The organic EL element of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device that projects an image, or a type that directly recognizes a still image or a moving image. It may be used as a display device (display). The driving method when used as a display device for moving image reproduction may be either a simple matrix (passive matrix) method or an active matrix method. Alternatively, a full-color display device can be manufactured by using two or more organic EL elements of the present invention having different emission colors.

  Hereinafter, an example of a display device having the organic EL element of the present invention will be described with reference to the drawings.

  FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements. It is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.

  The display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like. The control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside, and the pixels for each scanning line respond to the image data signal by the scanning signal. The image is scanned sequentially by emitting light, and the image information is displayed on the display unit A.

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

  The display unit A includes a wiring unit including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3 and the like on a substrate. The main members of the display unit A will be described below.

  In the figure, the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward). The scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions (details are illustrated). Not)

  When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6 and emits light according to the received image data. Full-color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.

  Next, the light emission process of the pixel will be described.

  FIG. 3 is a schematic diagram of a pixel.

  The pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like. A full color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 in a plurality of pixels, and juxtaposing them on the same substrate.

  In FIG. 3, an image data signal is applied from the control unit B to the drain of the switching transistor 11 through the data line 6. When a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5, the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is supplied to the capacitor 13 and the driving transistor 12. Is transmitted to the gate.

  By transmitting the image data signal, the capacitor 13 is charged according to the potential of the image data signal, and the drive of the drive transistor 12 is turned on. The drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10, and the organic EL element 10 is connected from the power supply line 7 according to the potential of the image data signal applied to the gate. Is supplied with current.

  When the scanning signal is moved to the next scanning line 5 by the sequential scanning of the control unit B, the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 11 is turned off, the capacitor 13 maintains the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied. Until then, the light emission of the organic EL element 10 continues. When the scanning signal is next applied by sequential scanning, the driving transistor 12 is driven and the organic EL element 10 emits light according to the potential of the next image data signal synchronized with the scanning signal.

  That is, the organic EL element 10 emits light by emitting the organic EL element 10 of each of the plurality of pixels 3 by providing the switching transistor 11 and the driving transistor 12 as active elements to the organic EL elements 10 of the plurality of pixels. Is going. Such a light emitting method is called an active matrix method.

  Here, the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or by turning on / off a predetermined light emission amount by a binary image data signal. Good. The potential of the capacitor 13 may be maintained until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.

  In the present invention, not only the active matrix method described above, but also a passive matrix light emission drive in which the organic EL element emits light according to the data signal only when the scanning signal is scanned.

  FIG. 4 is a schematic diagram of a passive matrix display device. In FIG. 4, a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.

  When the scanning signal of the scanning line 5 is applied by sequential scanning, the pixel 3 connected to the applied scanning line 5 emits light according to the image data signal.

  In the passive matrix system, the pixel 3 has no active element, and the manufacturing cost can be reduced.

  The organic EL material of the present invention can be applied to an organic EL element that emits substantially white light as a lighting device. A plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials to obtain white light emission by color mixing. The combination of a plurality of emission colors may include three emission maximum wavelengths of the three primary colors of blue, green, and blue, or two using the relationship of complementary colors such as blue and yellow, blue green and orange, etc. The thing containing the light emission maximum wavelength may be used.

  In addition, the combination of luminescent materials for obtaining multiple luminescent colors is a combination of multiple phosphorescent or fluorescent materials that emit light, fluorescent materials or phosphorescent materials, and light from the luminescent materials. Any combination with a dye material that emits light as light may be used, but in the white organic EL device according to the present invention, it is only necessary to mix and mix a plurality of light emitting dopants. It is only necessary to provide a mask only when forming a light emitting layer, a hole transport layer, an electron transport layer, etc., and simply arrange them separately by coating with the mask. In addition, for example, an electrode film can be formed by a vapor deposition method, a cast method, a spin coating method, an ink jet method, a printing method, etc., and productivity is also improved. According to this method, unlike a white organic EL device in which light emitting elements of a plurality of colors are arranged in parallel in an array, the elements themselves are luminescent white.

  There is no restriction | limiting in particular as a luminescent material used for a light emitting layer, For example, in the case of the backlight in a liquid crystal display element, the light emission dopant which concerns on this invention, Any one of known light emitting materials may be selected and combined to be whitened.

  As described above, the white light-emitting organic EL element according to the present invention is used as a light-emitting light source and a lighting device in addition to the display device and display. Further, it is also useful for display devices such as backlights for liquid crystal display devices. Others such as backlights for watches, signboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, light sources for optical sensors, etc. There are a wide range of uses such as household appliances.

  EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated in detail, the aspect of this invention is not limited to this.

Example 1
<< Production of organic EL element >>
After patterning on a substrate (NH Techno Glass: NA-45) made of ITO (Indium Tin Oxide) with a thickness of 150 nm on glass as an anode, the transparent support substrate provided with this ITO transparent electrode was i- After ultrasonic cleaning with propyl alcohol and drying with dry nitrogen gas, UV ozone cleaning was performed for 5 minutes.

This transparent support substrate was fixed to a substrate holder of a commercially available vacuum deposition apparatus, while 200 mg of α-NPD was placed in a molybdenum resistance heating boat, and 200 mg of Comparative Compound 1 was placed in another molybdenum resistance heating boat. 200 mg of bathocuproine (BCP) was placed in a resistance heating boat, and 200 mg of Alq ₃ was placed in another molybdenum resistance heating boat, which was attached to a vacuum deposition apparatus.

Next, after reducing the vacuum chamber to 4 × 10 ⁻⁴ Pa, the heating boat containing α-NPD was heated by heating, and the film thickness was formed on the transparent support substrate at a deposition rate of 0.1 to 0.3 nm / sec. Vapor deposition was performed at 50 nm to provide a hole transport layer. The substrate temperature during vapor deposition was room temperature.

Next, the heating boat containing the comparative compound 1 was energized and heated to provide a light emitting layer having a film thickness of 30 nm at a deposition rate of 0.1 to 0.3 nm / sec. Further, the heating boat containing BCP was heated by energization to provide a hole blocking layer having a thickness of 10 nm. Further, the heating boat containing Alq ₃ was energized and heated to provide an electron transport layer having a film thickness of 20 nm at a deposition rate of 0.1 to 0.3 nm / sec.

Next, a vacuum chamber is opened, and a stainless steel rectangular perforated mask is placed on the electron injection layer. On the other hand, 3 g of magnesium is placed in a molybdenum resistance heating boat, and 0.02 of silver is placed in a tungsten vapor deposition basket. After putting 5 g and depressurizing the vacuum chamber to 2 × 10 ⁻⁴ Pa again, the magnesium-containing boat was energized to deposit magnesium at a deposition rate of 1.5 to 2.0 nm / sec. At this time, a silver basket was heated at the same time, and silver was deposited at a deposition rate of 0.1 nm / sec to form a cathode made of the mixture of magnesium and silver, so that the comparative organic EL element OLED1 shown in Table 1 was used. -1 was produced.

  Next, in the production of the organic EL element OLED1-1, organic EL elements OLED1-2 to 1-26 were produced in the same manner except that the comparative compound 1 was changed to each compound described in Table 1. In addition, the luminescent color of each organic EL element showed blue to green.

<< Evaluation of organic EL elements >>
(External quantum efficiency)
The organic EL element is lit at room temperature (about 23 to 25 ° C.) under a constant current condition of ^2.5 mA / cm ² , and the light emission luminance (L) [cd / m ² ] immediately after the start of lighting and the time to halve the luminance Was measured to calculate the external extraction quantum efficiency (η) and half-life. Here, CS-1000 (manufactured by Konica Minolta Sensing) was used for measurement of light emission luminance. The external extraction quantum efficiency and half-life were expressed as relative values with the organic EL element 1-1 being 100.

  The results obtained as described above are shown in Table 1.

  As is apparent from Table 1, it can be seen that the organic EL device using the compound according to the present invention has improved light emission luminance at the start of lighting and time until the light emission luminance is reduced by half.

Example 2
In the production of the organic EL element OLED1-7 of Example 1, organic electroluminescence was similarly conducted except that a light emitting layer having a film thickness of 30 nm obtained by evaporating the exemplified compound B9 and DCM2 according to the present invention at a mass ratio of 100: 1 was used. Luminescence element OLED2-1 was produced. When the produced organic EL element OLED2-1 was applied with a DC voltage of 10 V in a dry nitrogen gas atmosphere at a temperature of 23 degrees, red light emission was obtained.

  In the production of the organic EL element OLED2-1, green or blue light emission was obtained by replacing DCM2 with Qd2 or BCzVBi, respectively.

Example 3
<< Production of organic EL element >>
After patterning on a substrate (NH Techno Glass: NA-45) made of ITO (indium tin oxide) with a film thickness of 150 nm on glass as an anode, a transparent support substrate provided with this ITO transparent electrode was i- After ultrasonic cleaning with propyl alcohol and drying with dry nitrogen gas, UV ozone cleaning was performed for 5 minutes.

This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of m-MTDATA is put into a molybdenum resistance heating boat, and 200 mg of DPVBi is put into another molybdenum resistance heating boat. 200 mg of Comparative Compound 3 is put into a molybdenum resistance heating boat, and vacuum deposition is performed. Then, after the vacuum chamber is depressurized to 4 × 10 ⁻⁴ Pa, the heating boat containing m-MTDATA is energized and heated, and the deposition rate is increased. Vapor deposition is performed at a film thickness of 25 nm on a transparent support substrate at 0.1 to 0.3 nm / sec, and the heating boat containing DPVBi is energized and heated to form a film at a vapor deposition rate of 0.1 to 0.3 nm / sec. A light emitting layer was provided by vapor deposition with a thickness of 20 nm. The substrate temperature during vapor deposition was room temperature.

  Next, the heating boat containing the comparative compound 3 was energized and heated to provide an electron transport layer having a film thickness of 30 nm at a deposition rate of 0.1 to 0.3 nm / sec.

Next, a vacuum chamber is opened, and a stainless steel rectangular perforated mask is placed on the electron transport layer. On the other hand, 3 g of magnesium is placed in a molybdenum resistance heating boat, and 0.02 of silver is placed in a tungsten vapor deposition basket. After putting 5 g and depressurizing the vacuum tank to 2 × 10 ⁻⁴ Pa again, energizing the boat containing magnesium to deposit magnesium at a deposition rate of 1.5 to 2.0 nm / sec. Was heated, and silver was deposited at a deposition rate of 0.1 nm / sec to form a cathode made of the mixture of magnesium and silver, thereby producing a comparative organic EL element OLED3-1.

  In the production of the organic EL element OLED3-1, organic EL elements OLED3-2 to 3-33 were produced in the same manner except that the comparative compound 3 was replaced with each compound described in Table 2.

<< Evaluation of organic EL elements >>
The external extraction quantum efficiency (η) and half-life were evaluated in the same manner as in Example 1. In addition, the luminescent color of all the organic EL elements was blue.

  As is apparent from Table 2, the organic EL device using the compound according to the present invention has improved light emission luminance at the start of lighting, light emission efficiency, and a time for halving the luminance with respect to the comparative example. It can be seen that the time to halve has been improved.

Example 4
Except that the cathode of the organic EL element OLED3-29 produced in Example 3 was replaced with Al, and a cathode buffer layer was provided by vapor deposition of lithium fluoride to a thickness of 0.5 nm between the electron transport layer and the cathode. In the same manner, an organic EL element OLED4-1 was produced.

When the produced organic EL element OLED4-1 was measured in the same manner as described in Example 3 for the light emission luminance (cd / m ² ) at the start of lighting and the time during which the luminance was reduced by half, the organic EL element OLED3 As a result of introducing a cathode buffer layer, it was confirmed that the effect was further exhibited as a result of introducing a cathode buffer layer.

Example 5
Each organic EL element was similarly manufactured except that the light emitting layer of each organic EL element produced in Example 3 was changed from DPVBi to a light emitting layer in which Alq ₃ or Alq ₃ and DCM 2 were deposited at a mass ratio of 100: 1. The emission luminance at the start of lighting (cd / m ² ) and the time for half the luminance were measured by the same method. As a result, as in Example 3, the organic EL device using the compound according to the present invention for the electron transport layer was turned on relative to the comparative examples (organic EL devices 3-1, 3-2, and 3-3). It was confirmed that the light emission luminance at the start (cd / m ² ) and the time for halving the luminance were improved.

In the case of using the Alq ₃ in the light emitting layer green light was obtained, the Alq ₃ and DCM2 100: The light-emitting layer were co-deposited at 1, red light was emitted.

Example 6
<< Production of organic EL element >>
After patterning a substrate (made by NH Techno Glass: NA-45) having a 150 nm ITO film formed on glass as an anode, the transparent support substrate provided with this ITO transparent electrode was ultrasonically cleaned with iso-propyl alcohol, Drying was performed with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.

This transparent support substrate is fixed to a substrate holder of a commercially available vacuum deposition apparatus, while α-NPD, H4, Ir-12, BAlq, and Alq ₃ are placed in five tantalum resistance heating boats, respectively, and a vacuum deposition apparatus (first (Vacuum chamber).

  Further, lithium fluoride was put into a tantalum resistance heating boat and aluminum was put into a tungsten resistance heating boat, respectively, and attached to the second vacuum tank of the vacuum evaporation apparatus.

First, after reducing the pressure of the first vacuum tank to 4 × 10 ⁻⁴ Pa, the heating boat containing α-NPD was energized and heated, and the transparent support substrate was deposited at a deposition rate of 0.1 to 0.2 nm / sec. The film was deposited to a thickness of 20 nm, and a hole injection / transport layer was provided.

  Further, the heating boat containing H4 and the boat containing Ir-12 were energized independently to adjust the deposition rate of H4 as a light emitting host and Ir-12 as a light emitting dopant to 100: 6. The light emitting layer was provided by vapor deposition to a thickness of 30 nm.

Subsequently, the said heating boat containing BAlq was heated by supplying electricity, and a hole blocking layer having a thickness of 10 nm was provided at a deposition rate of 0.1 to 0.2 nm / second. Further, the heating boat containing Alq ₃ was energized and heated to provide an electron transport layer having a film thickness of 20 nm at a deposition rate of 0.1 to 0.2 nm / second.

  Next, after the element deposited up to the electron transport layer was transferred to the second vacuum chamber while being vacuumed, it was remotely controlled from the outside of the apparatus so that a stainless steel rectangular perforated mask was placed on the electron transport layer. Installed.

After depressurizing the second vacuum tank to 2 × 10 ⁻⁴ Pa, a cathode buffer layer having a film thickness of 0.5 nm was provided at a deposition rate of 0.01 to 0.02 nm / second by energizing a boat containing lithium fluoride. Next, a boat containing aluminum was energized, a cathode having a film thickness of 150 nm was attached at a deposition rate of 1 to 2 nm / second, and an organic EL element OLED6-1 was produced.

  In the production of the organic EL element OLED6-1, organic EL elements OLED6-2 to 6-32 were produced in the same manner except that the host compound H4 was changed to the host compounds shown in Table 3.

<< Evaluation of organic EL elements >>
When evaluating the obtained organic EL elements OLED6-1 to 6-32, the non-light-emitting surface of each organic EL element after production is covered with a glass case, and a glass substrate having a thickness of 300 μm is used as a sealing substrate. An epoxy photo-curing adhesive (Lux Track LC0629B manufactured by Toagosei Co., Ltd.) is applied as a sealant around the periphery, and this is placed on the cathode so as to be in close contact with the transparent support substrate and irradiated with UV light from the glass substrate side. Then, it was cured and sealed, and an illumination device as shown in FIGS. 5 and 6 was formed and evaluated.

  FIG. 5 shows a schematic diagram of the lighting device, and the organic EL element 101 is covered with a glass cover 102 (in addition, the sealing operation with the glass cover is performed in a nitrogen atmosphere without bringing the organic EL element 101 into contact with the atmosphere. (In a high purity nitrogen gas atmosphere with a purity of 99.999% or more). 6 shows a cross-sectional view of the lighting device. In FIG. 6, reference numeral 105 denotes a cathode, 106 denotes an organic EL layer, and 107 denotes a glass substrate with a transparent electrode. The glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.

(External quantum efficiency)
By lighting the organic EL element under a constant current condition of room temperature (about 23 to 25 ° C.) and ^2.5 mA / cm ² , and measuring the emission luminance (L) [cd / m ² ] immediately after the start of lighting, The external extraction quantum efficiency (η) was calculated. Here, CS-1000 (manufactured by Konica Minolta Sensing) was used for measurement of light emission luminance. The external extraction quantum efficiency was expressed as a relative value with the organic EL element 6-1 as 100.

(Drive voltage)
Each voltage was measured when the organic EL element was driven at room temperature (about 23 to 25 ° C.) under a constant current condition of ^2.5 mA / cm ² , and the measurement result is as shown below. (Comparative example) is taken as 100 and each is shown as a relative value.

Voltage = (drive voltage of each element / drive voltage of the organic EL element 1-1) × 100
A smaller value indicates a lower drive voltage for comparison.

  From Table 3, it is clear that the organic EL device produced using the compound according to the present invention can achieve higher luminous efficiency and lower drive voltage than the comparative organic EL device.

Example 7
<< Production of organic EL element >>
After patterning a substrate (made by NH Techno Glass: NA-45) having a 150 nm ITO film formed on glass as an anode, the transparent support substrate provided with this ITO transparent electrode was ultrasonically cleaned with iso-propyl alcohol, Drying was performed with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.

This transparent support substrate is fixed to a substrate holder of a commercially available vacuum deposition apparatus, while α-NPD, H4, Ir-13, comparative compound 4 and Alq ₃ are placed in five tantalum resistance heating boats, respectively, and a vacuum deposition apparatus ( (First vacuum chamber).

  Further, lithium fluoride was placed in a resistance heating boat made of tantalum, and aluminum was placed in a resistance heating boat made of tungsten, and attached to the second vacuum tank of the vacuum evaporation apparatus.

First, after reducing the pressure of the first vacuum tank to 4 × 10 ⁻⁴ Pa, the heating boat containing α-NPD was energized and heated, and the transparent support substrate was deposited at a deposition rate of 0.1 to 0.2 nm / sec. The film was deposited to a thickness of 20 nm, and a hole injection / transport layer was provided.

  Furthermore, the heating boat containing H4 and the boat containing Ir-13 are energized independently to adjust the deposition rate of H4 as a light emitting host and Ir-13 as a light emitting dopant to 100: 6. The light emitting layer was provided by vapor deposition to a thickness of 30 nm.

Next, the heating boat containing the comparative compound 4 was energized and heated, and a hole blocking layer having a thickness of 10 nm was provided at a deposition rate of 0.1 to 0.2 nm / second. Further, the heating boat containing Alq ₃ was energized and heated to provide an electron transport layer having a film thickness of 20 nm at a deposition rate of 0.1 to 0.2 nm / second.

  Next, after the element deposited up to the electron transport layer was transferred to the second vacuum chamber while being vacuumed, it was remotely controlled from the outside of the apparatus so that a stainless steel rectangular perforated mask was placed on the electron transport layer. Installed.

After depressurizing the second vacuum tank to 2 × 10 ⁻⁴ Pa, a cathode buffer layer having a film thickness of 0.5 nm was provided at a deposition rate of 0.01 to 0.02 nm / second by energizing a boat containing lithium fluoride. Next, a boat containing aluminum was energized, a cathode having a film thickness of 150 nm was attached at a deposition rate of 1 to 2 nm / second, and an organic EL element OLED7-1 was produced.

  In the production of the organic EL element OLED7-1, organic EL elements OLED7-2 to 7-33 were produced in the same manner except that the comparative compound 4 of the electron transport layer compound was changed to the compounds shown in Table 4, respectively.

<< Evaluation of organic EL elements >>
Evaluation similar to Example 6 was performed. Table 4 shows the obtained results. In addition, it has each shown by the relative value which set the organic EL element OLED7-1 to 100.

  From Table 4, it is clear that the organic EL device produced using the compound according to the present invention can achieve higher light emission efficiency and lower drive voltage than the comparative organic EL device.

  Even when Ir-1, Ir-9, 1-8 is used as the light emitting dopant instead of Ir-13 and the compound according to the present invention is used as a hole blocking material, the luminous efficiency is improved and the driving voltage is reduced. It was found that there was a decrease.

Example 8
<Production of full-color display device>
(Production of blue light emitting element)
The organic EL element 6-5 of Example 6 was used as a blue light emitting element.

(Production of green light emitting element)
A green light emitting device was produced in the same manner as in the organic EL device 6-5 of Example 6 except that Ir-12 was changed to Ir-1, and this was used as a green light emitting device.

(Production of red light emitting element)
A red light emitting device was produced in the same manner as in the organic EL device 6-5 of Example 6 except that Ir-12 was changed to Ir-9, and this was used as a red light emitting device.

  The red, green, and blue light-emitting organic EL elements produced above were juxtaposed on the same substrate to produce an active matrix type full-color display device having a configuration as shown in FIG. In FIG. 2, only the schematic diagram of the display part A of the produced display device is shown.

  That is, a plurality of pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) juxtaposed with a wiring portion including a plurality of scanning lines 5 and data lines 6 on the same substrate. The scanning lines 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a lattice shape and are connected to the pixels 3 at the orthogonal positions (for details, see FIG. Not shown).

  The plurality of pixels 3 are driven by an active matrix system provided with an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5. The image data signal is received from the data line 6 and light is emitted according to the received image data. In this way, a full color display device was produced by appropriately juxtaposing red, green, and blue pixels.

  It has been found that when this full-color display device is driven, a high-brightness, high durability, and clear full-color moving image display can be obtained.

Example 9
<< Preparation of white light emitting element and white lighting device >>
The electrode of the transparent electrode substrate of Example 1 is patterned to 20 mm × 20 mm, and α-NPD is formed as a hole injection / transport layer with a thickness of 25 nm thereon, as in Example 1, and further contains H4. Further, the heating boat, the boat containing the exemplified compound Ir-13, and the boat containing Ir-9 were energized independently to deposit H4 as the light emitting host and Ir-13 and Ir-9 as the light emitting dopants. Was adjusted to be 100: 5: 0.6, vapor deposition was performed so as to have a thickness of 30 nm, and a light emitting layer was provided.

Next, Example Compound A30 was deposited to a thickness of 10 nm to provide a hole blocking layer. Further, Alq ₃ was deposited at 40 nm to provide an electron transport layer.

  Next, as in Example 1, a square perforated mask having the same shape as the transparent electrode made of stainless steel was placed on the electron injection layer, and lithium fluoride 0.5 nm was used as the cathode buffer layer and aluminum 150 nm was used as the cathode. Evaporated film was formed.

  This element was provided with a sealing can having the same method and the same structure as in Example 1, and a flat lamp as shown in FIGS. 5 and 6 was produced. When this flat lamp was energized, almost white light was obtained, and it was found that it could be used as a lighting device.

  Similar effects were obtained when Exemplified Compounds B30 and C30 were used instead of Exemplified Compound A30.

It is the schematic diagram which showed an example of the display apparatus comprised from an organic EL element. 4 is a schematic diagram of a display unit A. FIG. It is a schematic diagram of a pixel. It is a schematic diagram of a passive matrix type full-color display device. It is the schematic of an illuminating device. It is a schematic diagram of an illuminating device.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 Display 3 Pixel 5 Scan line 6 Data line 7 Power supply line 10 Organic EL element 11 Switching transistor 12 Drive transistor 13 Capacitor A Display part B Control part 102 Glass cover 105 Cathode 106 Organic EL layer 107 Glass substrate with a transparent electrode 108 Nitrogen gas 109 Water catcher

Claims (16)

An organic electroluminescence device comprising at least one compound represented by the following general formula (1).

(In the formula, Z represents an n-valent linking group or a simple bond, and A represents a group represented by the general formula (A1). N represents an integer of 2 or more and 6 or less. In the general formula (A1), , Ar represents an arylene group, R _{1 to} R ₆ each represent a hydrogen atom or a substituent, and X ₁₁ and X ₁₂ represent a nitrogen atom or —CR _11, and at least one of X ₁₁ and X ₁₂ R ₁₁ represents a hydrogen atom or a substituent, and among R _{1 to} R ₆ and R ₁₁ , adjacent substituents may be condensed with each other to form a ring. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).

(In the formula, A represents the general formula (A1), Z1 represents the following, and n represents an integer of 2 or more and 6 or less.)

(In Z1, at least two of Ra to Re are substituents represented by the general formula (A1), and the plurality of substituents may be the same or different. Of Ra to Re, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent, and adjacent substituents may be condensed with each other to form a ring.) The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (3).

(In the formula, A represents the general formula (A1), Z2 represents the following, and n represents an integer of 2 or more and 6 or less.)

(In Z2, at least two of Ra to Rf are substituents represented by the general formula (A1), and the plurality of substituents may be the same or different. Of Ra to Rf, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent, and adjacent substituents may be condensed with each other to form a ring.) The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (4).

(In the formula, A represents the general formula (A1), Z3 represents the following, and n represents an integer of 2 or more and 6 or less.)

(In Z3, at least two of Ra to Rf are substituents represented by the general formula (A1), and the plurality of substituents may be the same or different. Of Ra to Rf, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent, and adjacent substituents may be condensed with each other to form a ring.) The organic electroluminescence device according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (5).

(In the formula, A represents the general formula (A1), Z4 represents the following, and n represents 2 or 3.)

(In Z4, at least two of Ra to Rc are substituents represented by the general formula (A1), and the plurality of substituents may be the same or different. Of Ra to Rc, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent.) The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (6).

(In the formula, A represents the general formula (A1), Z5 represents the following, and n represents 2 or 3.)

(In Z5, at least two of Ra to Rc are substituents represented by the general formula (A1), and the plurality of substituents may be the same or different. Of Ra to Rc, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent.) The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (7).

(In the formula, A represents the general formula (A1), Z6 represents the following, and n represents 3 or 4.)

(In Z6, at least two of Ra to Rd are substituents represented by formula (A1), and the plurality of substituents may be the same or different. Of Ra to Rd, Those not represented by the general formula (A1) each represent a hydrogen atom or an arbitrary substituent, and adjacent substituents may be condensed with each other to form a ring.) The organic electroluminescence device according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (8).

(In the formula, Ar ₁ represents an n-valent arylene group, and R _{1 to} R ₆ each represents a hydrogen atom or a substituent. X ₁₁ and X ₁₂ represent a nitrogen atom or —CR ₁₁ , but X ₁₁ , X ₁₂ At least one of them is a nitrogen atom, R ₁₁ represents a hydrogen atom or a substituent, n represents an integer of 2 to 6. Among R _{1 to} R ₆ and R ₁₁ , adjacent substituents May be condensed with each other to form a ring.) An electron transport layer contains at least one compound selected from the compounds represented by the general formulas (1) to (8). The light emitting layer contains at least one compound selected from the compounds represented by the general formulas (1) to (8). In the organic electroluminescence device having a light emitting layer containing a host compound and a phosphorescent compound, the host compound is at least one compound selected from the compounds represented by the general formulas (1) to (8). An organic electroluminescence device characterized by the above. 12. The organic electroluminescence device according to claim 11, wherein the phosphorescent compound is an iridium compound, an osmium compound, or a platinum compound. The organic electroluminescent device according to claim 12, wherein the phosphorescent compound is an iridium compound. The organic electroluminescence device according to claim 1, wherein the organic layer is formed by a wet process. A display device comprising the organic electroluminescence element according to claim 1. An illuminating device comprising the organic electroluminescence element according to claim 1.

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