JP5304653B2 - Organic electroluminescence element, display device and lighting device - Google Patents

Abstract

Disclosed is an organic electroluminescent device having high emission luminance and low driving voltage. Also disclosed are an illuminating device and a display device each using such an organic electroluminescent device. The organic electroluminescent device is characterized by containing at least one compound represented by the following general formula (1). (In the formula (1), A represents a group represented by the above general formula (A), and a plurality of A's may be the same as or different from each other; n1 represents an integer of 6-8; X11 and X12 respectively represent a nitrogen atom or CR13; R13 and R14 respectively represent a hydrogen atom or a substituent, but do not combine together to form a ring; when X11 and X12 both represent CR13, R13's may be the same as or different from each other; x represents an integer of 0 or 1, and when x is 1, -Y- and -Z- respectively represent a direct bond or -O-, -S- or -N(R15)-; and R15 represents a substituent.)

Description

  The present invention relates to an organic electroluminescence element, a display device, and a lighting device.

  Conventionally, as a light-emitting electronic display device, there is an electroluminescence display (hereinafter referred to as ELD). Examples of constituent elements of ELD include inorganic electroluminescent elements and organic electroluminescent elements (hereinafter also referred to as organic EL elements).

  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 EL device has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, injects electrons and holes into the light emitting layer, and recombines them to generate excitons (exciton). It is an element that emits light by using light emission (fluorescence / phosphorescence) when this exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts, and is also self-luminous. In addition, it is attracting attention from the viewpoints of space saving, portability and the like because it is a thin film type complete solid element with a wide viewing angle and high visibility.

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

  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 an improvement in light emission luminance and a longer device lifetime. Further, an element having an organic light-emitting layer in which an 8-hydroxyquinoline aluminum complex is used as a host compound and a small amount of phosphor is doped thereto (for example, JP-A 63-264692), and an 8-hydroxyquinoline aluminum complex is used as a host compound. For example, an element having an organic light emitting layer doped with a quinacridone dye (for example, JP-A-3-255190) is known.

  In the technique disclosed in the above document, when the emission from excited singlet is used, the generation ratio of singlet excitons and triplet excitons is 1: 3. In addition, since the light extraction efficiency is about 20%, the limit of the external extraction quantum efficiency (η) is set to 5%.

  However, since Princeton University reported on an organic EL device using phosphorescence emission from an excited triplet (MA Baldo et al., Nature, 395, 151-154 (1998)), Research on materials that exhibit phosphorescence has become active.

  For example, M.M. A. Baldo et al. , Nature, 403, 17, 750-753 (2000), US Pat. No. 6,097,147, and the like.

  When the excited triplet is used, the upper limit of the internal quantum efficiency is 100%. In principle, the luminous efficiency is four times that of the excited singlet, and there is a possibility that almost the same performance as a cold cathode tube can be obtained. Therefore, it is attracting attention as a lighting application.

  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.

  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 luminance by introducing a hole blocking layer (exciton blocking layer) is also disclosed. For example, Pioneer achieves highly efficient light emission by using an example of using a certain aluminum complex and a fluorine-substituted compound (for example, see 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).
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 Appl. Phys. Lett. 79, 156 (2001)

  An object of the present invention is to provide an organic electroluminescence element exhibiting high light emission luminance and having a low driving voltage, and an illumination device and a display device using the element.

  The above object of the present invention can be achieved by the following constitution.

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

(Wherein, A is represented by the following general formula (A), a plurality of A may be the same as or different from each other. N1 represents an integer of 6 to 8. n2 represents an integer of 0 to 2. , n1 + n2 If _{.X 11, X 12} representing the 8 represented by any _{CR 13} of .X ₁₁ and _{X 12} which represents a nitrogen atom or _{CR 13, R 13} good .x be the same or different are If .x represents an integer of 0 or 1 is 1, -Y -, - Z- is a direct bond or -O -, - S -, - N (R 15) -. represented by any one of _{R 11} , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ are a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkoxy group, cyclo Alkoxy group, aryloxy group, alkylthio group, cycloalkyl group Group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, amino group Represents a halogen atom, a fluorinated hydrocarbon group, a cyano group, a nitro group, a hydroxy group, a mercapto group or a silyl group, but they are not bonded to each other to form a ring .
2. 2. The organic electroluminescence device according to 1 above, wherein the general formula (1) is represented by the following general formula (2).

(In the formula, A is represented by the general formula (A), and a plurality of A may be the same or different from each other. R ₂₁ represents a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic group. Aromatic hydrocarbon group, aromatic heterocyclic group, heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl Group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, amino group, halogen atom, fluorinated hydrocarbon group, cyano group, nitro group, hydroxy group Represents a mercapto group or a silyl group , but is bonded to each other to form a ring The plurality of R ₂₁ may be the same or different, n3 represents an integer of 6 to 8, n4 represents an integer of 0 to 2, and n3 + n4 represents 8.)
3. 2. The organic electroluminescence device according to 1 above, wherein the general formula (1) is represented by the following general formula (3).

(In the formula, A is represented by the general formula (A), and a plurality of A may be the same or different from each other. R ₃₁ is a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic group. Aromatic hydrocarbon group, aromatic heterocyclic group, heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl Group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, amino group, halogen atom, fluorinated hydrocarbon group, cyano group, nitro group, hydroxy group Represents a mercapto group or a silyl group , but is bonded to each other to form a ring The plurality of R ₃₁ may be the same or different, n5 represents an integer of 6 to 8, n6 represents an integer of 0 to 2, and n5 + n6 represents 8.)
4). 2. The organic electroluminescence device according to 1 above, wherein the general formula (1) is represented by the following general formula (4).

(In the formula, A is represented by the general formula (A), and a plurality of A may be the same or different from each other. R ₄₁ is a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic group. Aromatic hydrocarbon group, aromatic heterocyclic group, heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl Group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, amino group, halogen atom, fluorinated hydrocarbon group, cyano group, nitro group, hydroxy group Represents a mercapto group or a silyl group , but is bonded to each other to form a ring The plurality of R ₄₁ may be the same or different, n7 represents an integer of 6 to 8, n8 represents an integer of 0 to 2, and n7 + n8 represents 8.)
5. 2. The organic electroluminescence device according to 1 above, wherein the general formula (1) is represented by the following general formula (5).

(Wherein, A is represented by the general formula (A), a plurality of A may be the same or different. R ₅₁ and R ₅₂ are a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group. Group, aromatic hydrocarbon ring group, aromatic heterocyclic group, heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl Group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, amino group, halogen atom, fluorinated hydrocarbon group, cyano group, nitro group , hydroxy group, represents a mercapto group or a silyl group, bonded to one another Do not form a ring. Multiple _{R 51} is .n9 which may be the same or different is an integer of 6-8, n10 represents an integer of 0 to 2, n9 + n10 represents 8.)
6). The organic electroluminescent element according to any one of 1 to 5, wherein the general formula (A) is represented by the following general formula (A1).

(In the formula, R _a1 , R _a2 , R _a3 and R _a4 are a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, and an alkoxy group. Group, cycloalkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, An alkylsulfonyl group, an arylsulfonyl group, a heteroarylsulfonyl group, an amino group, a halogen atom, a fluorinated hydrocarbon group, a cyano group, a nitro group, a hydroxy group, a mercapto group, or a silyl group (* represents a bonding site)
7). 6. The organic electroluminescence element according to any one of 1 to 5, wherein the general formula (A) is represented by the following general formula (A2).

Wherein R _b1 , R _b2 and R _b3 are a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkoxy group, a cyclo group Alkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group An arylsulfonyl group, a heteroarylsulfonyl group, an amino group, a halogen atom, a fluorinated hydrocarbon group, a cyano group, a nitro group, a hydroxy group, a mercapto group, or a silyl group, and * represents a bonding site.
8). 6. The organic electroluminescent element according to any one of 1 to 5, wherein the general formula (A) is represented by the following general formula (A3).

(Wherein R _c1 , R _c2 and R _c3 are a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkoxy group, cyclo Alkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group An arylsulfonyl group, a heteroarylsulfonyl group, an amino group, a halogen atom, a fluorinated hydrocarbon group, a cyano group, a nitro group, a hydroxy group, a mercapto group, or a silyl group, and * represents a bonding site.
9. 6. The organic electroluminescence device according to any one of 1 to 5, wherein the general formula (A) is represented by the following general formula (A4).

(Wherein R _d1 and R _d2 are a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkoxy group, a cycloalkoxy group, Aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group A group, a heteroarylsulfonyl group, an amino group, a halogen atom, a fluorinated hydrocarbon group, a cyano group, a nitro group, a hydroxy group, a mercapto group, or a silyl group (* represents a bonding site).
10. 10. The organic material according to any one of 1 to 9 above, wherein the electron transport layer or the hole blocking layer contains at least one of the compounds represented by the general formulas (1) to (5). Electroluminescence element.

  11. 10. The organic electroluminescent device according to any one of 1 to 9, wherein the light emitting layer contains at least one of compounds represented by the general formulas (1) to (5).

  12 In an organic electroluminescence device comprising a host compound and a phosphorescent compound, the host compound is at least one compound selected from the compounds represented by formulas (1) to (5). The organic electroluminescence device according to any one of 1 to 11, wherein the organic electroluminescence device is any one of the above.

  13. In the organic electroluminescence device characterized by containing a host compound, a phosphorescent compound and an electron transporting compound, the electron transporting compound is selected from the compounds represented by the general formulas (1) to (5). 13. The organic electroluminescence device according to any one of 1 to 12 above, which is at least one compound selected.

  14 14. The organic electroluminescence device as described in 12 or 13, wherein the phosphorescent compound is an iridium compound or a platinum compound.

  15. 15. The organic electroluminescence device as described in 14 above, wherein the phosphorescent compound is an iridium compound.

  16. The organic electroluminescent element characterized by forming the organic layer containing the compound of any one of said 1-15 by a wet process.

  17. 17. A display device comprising the organic electroluminescence element according to any one of 1 to 16.

  18. An illuminating device comprising the organic electroluminescence element according to any one of 1 to 16 above.

  According to the present invention, an organic electroluminescence element exhibiting high light emission luminance and a low driving voltage, and an illumination device and a display device using the element can be provided.

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

  Hereinafter, the present invention will be described in detail.

  As a result of intensive studies, the present inventors have used organic compounds that exhibit high emission luminance and low driving voltage by using at least one of the compounds represented by the general formulas (1) to (5). It has been found that an 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 device of the present invention includes at least one compound represented by the general formula (1) to the general formula (5) in at least one layer constituting the organic EL device. Although it is an essential requirement for obtaining the effect described in the invention, it is preferable that the above-mentioned compound is contained in the light emitting layer, the hole blocking layer or the electron transporting layer.

  Heterocyclic derivatives such as pyridine derivatives and pyrimidine derivatives are known as electron transporting materials, and their molecular structures are substituted as a substituent on a specific mother nucleus as in general formulas (1) to (5). It was found that the drive voltage of the device can be greatly reduced as compared with conventional compounds by introducing eight specific heterocyclic derivatives.

  Furthermore, in the compounds according to the present invention, the optimization of the kind and number of a specific mother nucleus and its substituent was examined. As a result, naphthalene, dibenzofuran, dibenzothiophene, carbazole, and the like are preferably used as a specific mother nucleus, and 6 to 8 pyridines, pyrimidines, triazines, and derivatives thereof are used as the heterocyclic derivatives of substituents. Has been found to be preferably used. These structural features have led to the achievement of high light emission efficiency and low drive voltage as seen in the present invention.

The background of the use of derivatives in which aromatic heterocycles are polysubstituted as used in the present invention is largely due to the development of new synthetic methods. According to a recent new synthesis method, an aryl halide and an aromatic compound are coupled in the presence of a ruthenium catalyst and an organophosphorus compound to obtain a biaryl structure. By using a metal catalyst during this reaction, A plurality of bonds between sp ² carbons can be formed at a time by coupling of a carbon-hydrogen bond between an aryl halide and an aromatic compound. According to this synthesis method, it is possible to efficiently synthesize an asymmetric polysubstituted aromatic compound which has heretofore been difficult to synthesize. This synthesis method was found to be applicable to polysubstituted pyridine derivatives, polysubstituted pyrimidine derivatives, and the like. Therefore, it has been found that even a special structure such as the general formulas (1) to (5) can be synthesized as in the present invention.

  This synthesis method improves the yield of polysubstituted aromatic compounds by simplifying the synthesis process, manufactures new polysubstituted aromatic compounds, and also provides safety and harmony with the environment when producing polysubstituted aromatic compounds. Can be improved.

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

  Here, the compounds represented by the general formulas (1) to (5) according to the present invention will be described.

In the general formula (1), A is represented by the general formula (A), but a plurality of A may be the same as or different from each other. X ₁₁ and X _{12 each} represent a nitrogen atom or CR ₁₃ . R ₁₁ , R ₁₂ and R ₁₃ each represent a hydrogen atom or a substituent, but they are not bonded to each other to form a ring. When both X ₁₁ and X ₁₂ are represented by CR ₁₃ , R ₁₃ may be the same or different. * Represents a binding site.

Examples of the substituent represented by R ₁₁ , R ₁₂ and R ₁₃ include an alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group). Group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (eg, vinyl group, allyl group, etc.), alkynyl group (eg, ethynyl group, propargyl group, etc.), Aromatic hydrocarbon ring group (also called aromatic carbocyclic group, aryl group, etc., for example, phenyl group, p-chlorophenyl group, mesityl group, tolyl group, xylyl group, naphthyl group, anthryl group, azulenyl group, acenaphthenyl group, Fluorenyl group, phenanthryl group, indenyl group, pyrenyl group, biphenylyl group, etc.), aromatic compound A cyclic group (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, quinolyl group, benzofuryl group, dibenzofuryl group, benzothienyl group, A dibenzothienyl group, an indolyl group, a carbazolyl group, a carbolinyl group, a diazacarbazolyl group (in which one of the carbon atoms constituting the carboline ring of the carbolinyl group is replaced by a nitrogen atom), a quinoxalinyl group, a pyridazinyl group, Triazinyl group, quinazolinyl group, lid Razinyl group, etc.), heterocyclic groups (eg, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.), alkoxy groups (eg, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group, octyloxy group) 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 (eg, phenylthio group, naphthylthio group, etc.), alkoxy Carbonyl group (for example, methyloxycarbonyl group, ethyloxycarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (for example, 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, acetyl group, ethylcarbonyl group, propylcarbonyl group, Nylcarbonyl 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, dimethylcarbonylamino group, propylcarbonylamino group, pentylcarbonyl) Amino group, cyclohexylcarbonylamino group, 2-ethylhexylcarbonylamino group, octylcarbonylamino group, dodecylcarbonylamino group, phenyl Carbonylamino group, naphthylcarbonylamino group, etc.), carbamoyl group (for example, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexylaminocarbonyl 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-pyridylaminoureido group, etc.), sulfinyl group (for example, Tylsulfinyl group, ethylsulfinyl group, butylsulfinyl group, cyclohexylsulfinyl group, 2-ethylhexylsulfinyl group, dodecylsulfinyl group, phenylsulfinyl group, naphthylsulfinyl group, 2-pyridylsulfinyl group, etc.), 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, phenylsulfonyl group, naphthylsulfonyl group, 2-pyridylsulfonyl group) Etc.), amino group (for example, amino group, ethylamino group, dimethylamino group, butylamino group, cyclopentylamino group, 2-ethylhexyl) Mino group, dodecylamino group, anilino group, naphthylamino group, 2-pyridylamino group, etc.), halogen atom (eg, fluorine atom, chlorine atom, bromine atom etc.), fluorinated hydrocarbon group (eg, fluoromethyl group, trimethyl group) Fluoromethyl 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.

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

In General formula (1), n1 represents the integer of 6-8. n2 represents an integer of 0 to 2, but n1 + n2 represents 8. x represents an integer of 0 or 1. For x = 1, -Y -, - Z- is a direct bond or, -O -, - S -, - N (R 15) - is represented by any one of the. R ₁₄ represents a hydrogen atom or a substituent. R ₁₅ represents a substituent. When R <_14> , R < ₁₅ > represents a substituent, it is synonymous with R < ₁₁ >, R < ₁₂ >, R < ₁₃ >.

In the general formula (2), A is represented by the general formula (A), but a plurality of A may be the same as or different from each other. R ₂₁ represents a hydrogen atom or a substituent, but is not bonded to each other to form a ring. A plurality of R ₂₁ may be the same or different. n3 represents an integer of 6 to 8, n4 represents an integer of 0 to 2, and n3 + n4 represents 8. The substituent represented by R ₂₁ has the same meaning as R ₁₁ , R ₁₂ and R ₁₃ .

In the general formula (3), A is represented by the general formula (A), but a plurality of A may be the same as or different from each other. R ₃₁ represents a hydrogen atom or a substituent, but does not bond to each other to form a ring. A plurality of R ₃₁ may be the same or different. n5 represents an integer of 6 to 8, n6 represents an integer of 0 to 2, and n5 + n6 represents 8. Substituents R ₃₁ is represented has the same meaning as _{R 11, R 12, R 13} .

In the general formula (4), A is represented by the general formula (A), but a plurality of A may be the same as or different from each other. R ₄₁ represents a hydrogen atom or a substituent, but is not bonded to each other to form a ring. The plurality of R ₄₁ may be the same or different. n7 represents an integer of 6 to 8, n8 represents an integer of 0 to 2, and n7 + n8 represents 8. Substituents R ₄₁ is represented has the same meaning as _{R 11, R 12, R 13} .

In the general formula (5), A is represented by the general formula (A), but a plurality of A may be the same as or different from each other. R ₅₁ represents a hydrogen atom or a substituent, but is not bonded to each other to form a ring. A plurality of R ₅₁ may be the same or different. R ₅₂ represents a substituent. n9 represents an integer of 6 to 8, n10 represents an integer of 0 to 2, and n9 + n10 represents 8. The substituents represented by R ₅₁ and R ₅₂ have the same meanings as R ₁₁ , R ₁₂ and R ₁₃ .

As general formula (A), the structure chosen from the said general formula (A1)-general formula (A4) is preferable. The substituents represented by R _a1 , R _a2 , R _a3 , R _a4 , R _b1 , R _b2 , R _b3 , R _c1 , R _c2 , R _c3 , R _d1 , R _d2 are R ₁₁ , R ₁₂ , It has the same meaning as R _13.

  Hereinafter, specific examples of the compounds according to the present invention represented by the general formulas (1) to (5) are shown below.

  The synthesis example of a typical compound is shown below.

Synthesis of Exemplary Compound 1 Under a nitrogen atmosphere, 2-naphthylpyridine (1.0 mmol), ruthenium complex [(η ⁶ -C ₆ H ₆ ) RuCl ₂ ] ₂ (0.05 mmol), triphenylphosphine (0.2 mmol), Potassium carbonate (12 mmol) was mixed in 3 ml of NMP (N-methyl-2-pyrrolidone). The temperature was raised to 140 ° C., and a solution of 2-bromopyridine (12.0 mmol) in NMP (N-methyl-2-pyrrolidone) (2.0 ml) was added dropwise over 20 hours (using a syringe pump). The mixture was further stirred at that temperature for 4 hours.

After cooling the reaction solution to room temperature, 5 ml of dichloromethane is added and the reaction solution is filtered. The filtrate was distilled off the solvent under reduced pressure (800 Pa, 80 ° C.), and the residue (N-methyl-2-pyrrolidone) was subjected to silica gel flash chromatography (CH ₂ Cl ₂ : Et ₃ N = 20: 1 to 10: 1). It refine | purified in.

  Each fraction was collected and the solvent was distilled off under reduced pressure. The residue was redissolved in dichloromethane and washed three times with water. The organic phase was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain Exemplary Compound 1.

<< Application of the Compound of the Present Invention to an Organic EL Element >>
When producing the organic EL device of the present invention using the compound according to the present invention, the light emitting layer, the hole blocking layer or the electron transporting layer is included in the present invention in the constituent layers (details will be described later) of the organic EL device. It is preferable to use such a compound. In the light emitting layer, it is preferably used as a host compound (also referred to as a light emitting host) as described above.

(Light emitting host and light emitting dopant)
The mixing ratio of the light-emitting dopant to the light-emitting host, which is the host compound as the main component in the light-emitting layer, is preferably adjusted to a range of 0.1 to less than 30% by mass.

  Luminescent dopants can be broadly classified into two types: fluorescent compounds that emit fluorescence and phosphorescent compounds that emit phosphorescence.

  Representative examples of the former (fluorescent compound) include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, Examples include perylene dyes, stilbene dyes, polythiophene dyes, and rare earth complex phosphors.

  A typical example of the latter (phosphorescent compound) is preferably a complex compound containing a transition metal element of Group 8, 9, or 10 in the periodic table, and more preferably an iridium complex compound or a platinum complex compound. It is.

  Specifically, it is a compound described in the following patent publications.

  WO 00/70655 pamphlet, JP 2002-280178, JP 2001-181616, JP 2002-280179, JP 2001-181617, JP 2002-280180, JP 2001-247859, JP 2002-299060, JP 2001-313178, JP 2002-302671, JP 2001-345183, JP 2002-324679, International Publication No. 02/15645 pamphlet, JP 2002-332291 A, JP 2002-50484 A, JP 2002-332292 A, JP 2002-83684 A, JP 2002-540572 A, JP 2002-2002 A. No. 117978, JP 20 JP-A-2-338588, JP-A-2002-170684, JP-A-2002-352960, WO01 / 93642, JP-A-2002-50483, JP-A-2002-1000047, JP-A-2002. No. -173744, JP-A No. 2002-359082, JP-A No. 2002-17584, JP-A No. 2002-363552, JP-A No. 2002-184582, JP-A No. 2003-7469, JP-T-2002-525808. Gazette, JP2003-7471, JP2002-525833, JP2003-31366, JP2002-226495, JP2002-234894, JP2002-2335076 JP 2002-241751 A JP 2001-319779, JP 2001-319780, JP 2002-62824, JP 2002-1000047, JP 2002-203679, JP 2002-343572, JP 2002-203678 gazette etc.

  Some specific examples are shown below.

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

(Light emitting host)
The host compound used in the present invention represents a compound having a phosphorescence quantum yield of phosphorescence emission of less than 0.01 at room temperature (25 ° C.) among the compounds contained in the light emitting layer.

  The light-emitting host that may be used in combination with the compound according to the present invention is not particularly limited in terms of structure, but is typically a carbazole derivative, a triarylamine derivative, an aromatic borane derivative, a nitrogen-containing heterocyclic compound, or a thiophene derivative. , Furan derivatives, oligoarylene compounds, etc. having a basic skeleton, or carboline derivatives or derivatives having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative is substituted with a nitrogen atom Etc. Among these, carbazole derivatives, carboline derivatives, and derivatives having a ring structure in which at least one carbon atom of the hydrocarbon ring constituting the carboline ring of the carboline derivative is substituted with a nitrogen atom are preferably used.

  Although the specific example of the light emission host which may be used together with the compound concerning this invention is given to the following, this invention is not limited to these. These compounds are also preferably used as hole blocking materials.

  In the light emitting layer according to the present invention, a plurality of known host compounds may be used in combination as a host compound. By using a plurality of types of host compounds, it is possible to adjust the movement of charges, and the organic EL element can be made highly efficient. As these known host compounds, 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) are preferable.

  The light emitting host used in the present invention may be a low molecular compound, a high molecular compound having a repeating unit, or a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (evaporation polymerizable light emitting host). .

  As the light-emitting host, a compound having a hole transporting ability and an electron transporting ability, preventing a long wavelength of light emission and having a high Tg (glass transition temperature) is preferable.

  As specific examples of the light-emitting host, compounds described in the following documents are suitable. For example, Japanese Patent Laid-Open Nos. 2001-257076, 2002-308855, 2001-313179, 2002-319491, 2001-357777, 2002-334786, JP2002-8860, JP2002-334787, JP2002-15871, JP2002-334788, JP2002-43056, JP2002-334789, JP JP 2002-75645 A, JP 2002-338579 A, JP 2002-105445 A, JP 2002-343568 A, JP 2002-141173 A, JP 2002-352957 A, JP 2002-2002 A. No. 203683, JP-A-2002-3632 7, JP 2002-231453, JP 2003-3165, JP 2002-234888, JP 2003-27048, JP 2002-255934, JP 2002-286061. JP, JP-A-2002-280183, JP-A-2002-299060, JP-A-2002-302516, JP-A-2002-305083, JP-A-2002-305084, JP-A-2002-308837, etc. .

  The light emitting layer may further contain a host compound having a fluorescence maximum wavelength as a host compound. In this case, the energy transfer from the other host compound and the phosphorescent compound to the fluorescent compound allows electroluminescence as an organic EL element to be emitted from the other host compound having a fluorescence maximum wavelength. A host compound having a fluorescence maximum wavelength is preferably a compound having a high fluorescence quantum yield in a solution state. Here, the fluorescence quantum yield is preferably 10% or more, particularly preferably 30% or more.

  The fluorescence quantum yield can be measured by the method described in Spectroscopic II, page 362 (1992 version, Maruzen) of the Fourth Edition Experimental Chemistry Course 7.

  Next, a configuration of a typical organic EL element will be described.

<< Constituent layers of organic EL elements >>
The constituent layers of the organic EL element of the present invention will be described.

  Although the preferable specific example of the layer structure of the organic EL element of this invention is shown below, this invention is not limited to these.

(I) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode (ii) Anode / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode (iii) Anode / Hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode (iv) Anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode ( v) Anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode (vi) Anode / anode buffer layer / hole transport layer / electron blocking layer / light emitting layer / Hole blocking layer / electron transport layer / cathode buffer layer / cathode (vii) Anode / anode buffer layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode 《Blocking layer (electron blocking layer, hole blocking layer)》
The blocking layer (for example, electron blocking layer, hole blocking layer) according to the present invention will be described.

  In the present invention, the compound according to the present invention is preferably used for the hole blocking layer, and particularly preferably used for the hole blocking layer.

  When the hole blocking layer contains the compound according to the present invention, the compound according to the present invention may be included in a state of 100% by mass as a layer constituting component of the hole blocking layer, or mixed with other organic compounds, etc. May be.

  The thickness of the blocking layer according to the present invention is preferably 3 to 100 nm, and more preferably 5 to 30 nm.

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

《Electron blocking layer》
On the other hand, the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed.

《Hole transport layer》
The hole transport layer includes 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.

  The hole transport material is not particularly limited, and is conventionally used as a hole charge injection / transport material in optical transmission materials, or a well-known material used for a hole injection layer or a hole transport layer of an organic EL device. 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.

  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. The hole transport layer may have a single layer structure composed of one or more of the above materials.

《Electron transport layer》
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 with a single layer or a plurality of layers.

  Conventionally, in the case of a single-layer electron transport layer and a plurality of layers, the following materials are used as the electron transport material (also serving as a hole blocking material) used for the electron transport layer adjacent to the cathode side with respect to the light emitting layer. Are known.

  Further, the electron transport layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer, and any material can be selected and used from conventionally known compounds.

  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, carboline derivatives, or at least one carbon atom of the hydrocarbon ring constituting the carboline ring of the carboline derivative is substituted with a nitrogen atom Examples thereof include derivatives having a ring structure.

  Furthermore, in the above oxadiazole derivative, a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, or 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 transport 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 an inorganic semiconductor such as n-type-Si, n-type-SiC, etc. as in the case of the hole injection layer and hole transport layer Can also be used as an electron transporting material.

  This electron transport layer can be formed by thinning the electron 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 an electron carrying layer, Usually, it is about 5-5000 nm. This electron transport layer may have a single layer structure composed of one or more of the above materials.

  Next, an injection layer used as a constituent layer of the organic EL element of the present invention will be described.

<< Injection Layer >>: Electron Injection Layer, Hole Injection Layer An injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, as described above, between the anode and the light emitting layer or the hole transport layer, and the cathode. Between the light emitting layer and the electron transport layer.

  An injection layer is a layer that is provided between an electrode and an organic layer in order to lower drive voltage and improve light emission brightness. “Organic EL elements and the forefront of their industrialization (issued by NTT Corporation on November 30, 1998) 2 of 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. Representative examples thereof include copper phthalocyanine. Phthalocyanine buffer layers, oxide buffer layers typified by vanadium oxide, amorphous carbon buffer layers, polymer buffer layers using conductive polymers such as polyaniline (emeraldine) and polythiophene, and the like.

  The details of the cathode buffer layer (electron injection layer) are also described in JP-A-6-325871, JP-A-9-17574, and JP-A-10-74586, and more specifically, strontium, aluminum, etc. Examples include a metal buffer layer represented by an alkali metal compound buffer layer represented by lithium fluoride, an alkaline earth metal compound buffer layer represented by magnesium fluoride, and an oxide buffer layer represented by aluminum oxide.

  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.

  This injection layer can be formed by thinning the above 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 an injection | pouring layer, Usually, it is about 5-5000 nm. The injection layer may have a single layer structure composed of one or more of the above materials.

"anode"
As the anode according to the organic EL device of the present invention, an electrode having a work function (4 eV or more) metal, alloy, electrically conductive compound and a mixture thereof as an electrode material is preferably used. Specific examples of such electrode substances 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, these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not so high (about 100 μm or more) A pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material. 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.

"cathode"
On the other hand, as the cathode according to the present invention, a cathode having a work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof 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, from the point of durability against electron injection and oxidation, etc., a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this, 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.

<< Substrate (also referred to as substrate, substrate, support, etc.) >>
The substrate of the organic EL device of the present invention is not particularly limited as to the type of glass, plastic and the like, 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.

<< Method for producing organic EL element >>
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. In view of the above, the vacuum deposition method or the spin coating method is particularly preferable. Further, different film forming methods 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.

<Display device>
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.

《Lighting device》
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.

  Further, 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 for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a 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 held continuously 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 pixels 3 connected to the applied scanning line 5 emit 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.

  In addition, the compound according to 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. Since other layers are common, patterning of the mask or the like is not necessary. 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, if it is a backlight in a liquid crystal display element, the phosphorescent compound which concerns on this invention so that it may suit the wavelength range corresponding to CF (color filter) characteristic In addition, 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 kind of lamp such as household illumination, interior lighting, and exposure light source as various light emitting light sources and lighting devices in addition to the display device and display. 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 demonstrates this invention, this invention is not limited to these.

Example 1
<< Production of Organic EL Element 1-1 >>
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 vapor deposition apparatus, while α-NPD, H-4, Ir-1, BAlq, and Alq ₃ are placed in five tantalum resistance heating boats, respectively. (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 H-4 and the boat containing Ir-1 are energized independently, and the deposition rate of H-4 as a light emitting host and Ir-1 as a light emitting dopant becomes 100: 6. The light emitting layer was provided by evaporating 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, electricity was supplied to the boat containing aluminum, and a cathode having a film thickness of 150 nm was attached at a deposition rate of 1 to 2 nm / second to produce an organic EL device 1-1.

<< Production of Organic EL Elements 1-2 to 1-38 >>
In the production of the organic EL element 1-1, organic EL elements 1-2 to 1-38 were produced in the same manner except that the host compound H-4 was changed to the host compounds shown in Table 1.

<< Evaluation of organic EL elements >>
When evaluating the obtained organic EL elements 1-1 to 1-38, the non-light-emitting surface of each organic EL element after production was covered with a glass case, and a glass substrate having a thickness of 300 μm was 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 is a schematic view 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 1-1 as 100.

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

(Change in drive voltage over time)
The organic EL element was continuously lit at a constant current of ^2.5 mA / cm ² at room temperature, and the driving voltage when the luminance reached 70% of the initial luminance was measured. As shown below, the measurement results are shown as relative values with the organic EL element 1-1 (comparative) as 100.

  Voltage = (drive voltage of each element / drive voltage of the organic EL element 1-1) × 100

  From Table 1, 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 driving voltage than the comparative organic EL device.

Example 2
<< Preparation of Organic EL Element 2-1 >>
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, H-1, Ir-13, BAlq, and Alq ₃ are placed in five tantalum resistance heating boats, respectively. (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.

  Further, the heating boat containing H-1 and the boat containing Ir-13 are energized independently, and the deposition rate of H-1 as a light emitting host and Ir-13 as a light emitting dopant becomes 100: 6. The light emitting layer was provided by evaporating 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, and a cathode having a film thickness of 150 nm was attached at a deposition rate of 1 to 2 nm / second to produce an organic EL element 2-1.

<< Production of Organic EL Elements 2-2 to 2-38 >>
In the production of the organic EL element 2-1, the organic EL elements 2-2 to 2-38 were similarly performed except that the host compound H-1 and the hole blocking compound BAlq were changed to the compounds shown in Table 2, respectively. Was made.

<< Evaluation of organic EL elements >>
Evaluation similar to Example 1 was performed. The obtained results are shown in Table 2. In addition, it has each shown by the relative value which set the organic EL element 2-1 to 100.

  From Table 2, 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.

  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 3
<Production of full-color display device>
(Production of blue light emitting element)
The organic EL element 2-6 of Example 2 was used as a blue light emitting element.

(Production of green light emitting element)
The organic EL element 1-6 of Example 1 was used as a green light emitting element.
(Production of red light emitting element)
In the organic EL element 2-1 of Example 2, a red light emitting element was produced in the same manner except that Ir-13 was changed to Ir-9, and this was used as a red light emitting element.

  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 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 4
<< Preparation of white light emitting element and white lighting device >>
The electrode of the transparent electrode substrate of Example 1 was patterned to 20 mm × 20 mm, and α-NPD was formed as a hole injection / transport layer with a thickness of 25 nm thereon as in Example 1, and further H-4 The heated boat containing Ir, the boat containing Ir-13, and the boat containing Ir-9 are energized independently, and H-4 as a light emitting host and Ir-13 and Ir-9 as light emitting dopants. The vapor deposition rate was adjusted to 100: 5: 0.6, vapor deposition was performed to a thickness of 30 nm, and a light emitting layer was provided.

Next, Example Compound 1 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.

Claims (18)

An organic electroluminescence device comprising at least one compound represented by the following general formula (1).
(Wherein, A is represented by the following general formula (A), a plurality of A may be the same as or different from each other. N1 represents an integer of 6 to 8. n2 represents an integer of 0 to 2. , n1 + n2 If _{.X 11, X 12} representing the 8 represented by any _{CR 13} of .X ₁₁ and _{X 12} which represents a nitrogen atom or _{CR 13, R 13} good .x be the same or different are If .x represents an integer of 0 or 1 is 1, -Y -, - Z- is a direct bond or -O -, - S -, - N (R 15) -. represented by any one of _{R 11} , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ are a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkoxy group, cyclo Alkoxy group, aryloxy group, alkylthio group, cycloalkyl group Group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, amino group Represents a halogen atom, a fluorinated hydrocarbon group, a cyano group, a nitro group, a hydroxy group, a mercapto group or a silyl group, but they are not bonded to each other to form a ring . The organic electroluminescence device according to claim 1 , wherein the general formula (1) is represented by the following general formula (2).
(In the formula, A is represented by the general formula (A), and a plurality of A may be the same or different from each other. R ₂₁ represents a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic group. Aromatic hydrocarbon group, aromatic heterocyclic group, heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl Group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, amino group, halogen atom, fluorinated hydrocarbon group, cyano group, nitro group, hydroxy group Represents a mercapto group or a silyl group , but is bonded to each other to form a ring The plurality of R ₂₁ may be the same or different, n3 represents an integer of 6 to 8, n4 represents an integer of 0 to 2, and n3 + n4 represents 8.) The organic electroluminescence device according to claim 1 , wherein the general formula (1) is represented by the following general formula (3).
(In the formula, A is represented by the general formula (A), and a plurality of A may be the same or different from each other. R ₃₁ is a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic group. Aromatic hydrocarbon group, aromatic heterocyclic group, heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl Group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, amino group, halogen atom, fluorinated hydrocarbon group, cyano group, nitro group, hydroxy group Represents a mercapto group or a silyl group , but is bonded to each other to form a ring The plurality of R ₃₁ may be the same or different, n5 represents an integer of 6 to 8, n6 represents an integer of 0 to 2, and n5 + n6 represents 8.) The organic electroluminescence device according to claim 1 , wherein the general formula (1) is represented by the following general formula (4).
(In the formula, A is represented by the general formula (A), and a plurality of A may be the same or different from each other. R ₄₁ is a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic group. Aromatic hydrocarbon group, aromatic heterocyclic group, heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl Group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, amino group, halogen atom, fluorinated hydrocarbon group, cyano group, nitro group, hydroxy group Represents a mercapto group or a silyl group , but is bonded to each other to form a ring The plurality of R ₄₁ may be the same or different, n7 represents an integer of 6 to 8, n8 represents an integer of 0 to 2, and n7 + n8 represents 8.) The said general formula (1) is represented by the following general formula (5), The organic electroluminescent element of Claim 1 characterized by the above-mentioned.
(Wherein, A is represented by the general formula (A), a plurality of A may be the same or different. R ₅₁ and R ₅₂ are a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group. Group, aromatic hydrocarbon ring group, aromatic heterocyclic group, heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl Group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, amino group, halogen atom, fluorinated hydrocarbon group, cyano group, nitro group , hydroxy group, represents a mercapto group or a silyl group, bonded to one another Do not form a ring. Multiple _{R 51} is .n9 which may be the same or different is an integer of 6-8, n10 represents an integer of 0 to 2, n9 + n10 represents 8.) The said general formula (A) is represented by the following general formula (A1), The organic electroluminescent element of any one of Claims 1-5 characterized by the above-mentioned.
(In the formula, R _a1 , R _a2 , R _a3 and R _a4 are a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, and an alkoxy group. Group, cycloalkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, An alkylsulfonyl group, an arylsulfonyl group, a heteroarylsulfonyl group, an amino group, a halogen atom, a fluorinated hydrocarbon group, a cyano group, a nitro group, a hydroxy group, a mercapto group, or a silyl group (* represents a bonding site) The said general formula (A) is represented by the following general formula (A2), The organic electroluminescent element of any one of Claims 1-5 characterized by the above-mentioned.
Wherein R _b1 , R _b2 and R _b3 are a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkoxy group, a cyclo group Alkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group An arylsulfonyl group, a heteroarylsulfonyl group, an amino group, a halogen atom, a fluorinated hydrocarbon group, a cyano group, a nitro group, a hydroxy group, a mercapto group, or a silyl group, and * represents a bonding site. The said general formula (A) is represented by the following general formula (A3), The organic electroluminescent element of any one of Claims 1-5 characterized by the above-mentioned.
(Wherein R _c1 , R _c2 and R _c3 are a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkoxy group, cyclo Alkoxy group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group An arylsulfonyl group, a heteroarylsulfonyl group, an amino group, a halogen atom, a fluorinated hydrocarbon group, a cyano group, a nitro group, a hydroxy group, a mercapto group, or a silyl group, and * represents a bonding site. The said general formula (A) is represented by the following general formula (A4), The organic electroluminescent element of any one of Claims 1-5 characterized by the above-mentioned.
(Wherein R _d1 and R _d2 are a hydrogen atom , an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkoxy group, a cycloalkoxy group, Aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, acyl group, acyloxy group, amide group, carbamoyl group, ureido group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group A group, a heteroarylsulfonyl group, an amino group, a halogen atom, a fluorinated hydrocarbon group, a cyano group, a nitro group, a hydroxy group, a mercapto group, or a silyl group (* represents a bonding site). The electron transport layer or the hole blocking layer contains at least one of the compounds represented by the general formula (1) to the general formula (5), according to any one of claims 1 to 9 . Organic electroluminescence device. The light emitting layer contains at least one of the compounds represented by the general formulas (1) to (5). The organic electroluminescent element according to any one of claims 1 to 9 , In an organic electroluminescence device comprising a host compound and a phosphorescent compound, the host compound is at least one compound selected from the compounds represented by formulas (1) to (5). The organic electroluminescence element according to claim 1 , wherein the organic electroluminescence element is any one of the following. In the organic electroluminescence device characterized by containing a host compound, a phosphorescent compound and an electron transporting compound, the electron transporting compound is selected from the compounds represented by the general formulas (1) to (5). It is at least 1 sort (s) of compound chosen, The organic electroluminescent element of any one of Claims 1-12 characterized by the above-mentioned. 12. or organic electroluminescence device according to 13, wherein the phosphorescent compound is an iridium compound or a platinum compound. The organic electroluminescent device according to claim 14 , wherein the phosphorescent compound is an iridium compound. The organic layer containing the compound of any one of Claims 1-15 is formed by a wet process, The organic electroluminescent element characterized by the above-mentioned. A display device comprising the organic electroluminescence element according to claim 1 . An illuminating device comprising the organic electroluminescence element according to claim 1 .