JP5055689B2 - ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, LIGHTING DEVICE AND DISPLAY DEVICE - Google Patents

Description

  The present invention relates to an organic electroluminescence element, an illuminating device, and a display device, and particularly relates to an organic electroluminescent element, an illuminating device, and a display device having the same that are excellent in light emission luminance, luminous efficiency, and durability.

  Conventionally, there is an electroluminescence display (ELD) as a light-emitting electronic display device. Examples of the 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.

  On the other hand, an organic EL element has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode. By injecting electrons and holes into the light emitting layer and recombining them, excitons (exciton) are obtained. And emits light using the emission of light (fluorescence / phosphorescence) when the exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts. Since it is a light-emitting type, it has a wide viewing angle, high visibility, and since it is a thin-film type complete solid-state device, it has attracted attention from the viewpoints of space saving and portability.

  For the development of organic EL elements for practical use in the future, organic EL elements that emit light efficiently and with high brightness with lower power consumption are desired. For example, stilbene derivatives, distyrylarylene derivatives, or tris A technique for doping a styrylarylene derivative with a small amount of a phosphor to improve emission luminance and extend the lifetime of the device (see, for example, Patent Document 1), and 8-hydroxyquinoline aluminum complex as a host compound. A device having an organic light-emitting layer doped with a trace amount of phosphor (for example, see Patent Document 2), a device having an organic light-emitting layer doped with a quinacridone dye as a host compound using 8-hydroxyquinoline aluminum complex (for example, , See Patent Document 3).

  In the technique disclosed in the above-mentioned patent document, when the emission from the excited singlet is used, the generation ratio of the singlet exciton and the triplet exciton is 1: 3, so the generation probability of the luminescent excited species is 25%. Since the light extraction efficiency is about 20%, the limit of the external extraction quantum efficiency (ηext) is set to 5%.

  However, since Princeton University has reported on organic EL devices that use phosphorescence emission from excited triplets (see, for example, Non-Patent Document 1), research on materials that exhibit phosphorescence at room temperature has become active. (For example, see Non-Patent Document 2 and Patent Document 4.)

  When excited triplets are used, the upper limit of internal quantum efficiency is 100%, so in principle the luminous efficiency is four times that of excited singlets, and the performance is almost the same as that of cold cathode tubes. It can be applied to and attracts attention.

  For example, many compounds have been studied focusing on heavy metal complexes such as iridium complexes (see, for example, Non-Patent Document 3).

  Further, studies using tris (2-phenylpyridine) iridium as a dopant have been made (for example, see Non-Patent Document 2).

In addition, L ₂ Ir (acac), for example, (ppy) ₂ Ir (acac) (see, for example, Non-Patent Document 4) as a dopant, and tris (2- (p-tolyl) pyridine) iridium (as a dopant) Studies using Ir (ptpy) ₃ ), tris (benzo [h] quinoline) iridium (Ir (bzq) ₃ ), Ir (bzq) ₂ ClP (Bu) _3, etc. (for example, see Non-Patent Document 5). Has been done.

  In addition, in order to obtain high luminous efficiency, a hole transporting compound is used as a host of the phosphorescent compound (see, for example, Non-Patent Document 6).

  Further, various electron transporting materials are used as a phosphorescent compound host, doped with a novel iridium complex (see, for example, Non-Patent Document 4). Furthermore, high luminous efficiency is obtained by introducing a hole blocking layer (see, for example, Non-Patent Document 5).

  Currently, further improvement in light emission efficiency and life of organic EL elements using phosphorescence emission are being studied.

However, although the external extraction efficiency of 20%, which is the theoretical limit for green light emission, has been achieved, it is only in the low current region (low luminance region), and the theoretical limit is still in the high current region (high luminance region). Not achieved. Furthermore, sufficient efficiency has not yet been obtained for other luminescent colors, and improvements are required. In addition, organic EL devices for practical application in the future will emit light efficiently and with high brightness. Development of the organic EL element which does is desired. In particular, there is a demand for an element that emits light with high efficiency in an organic EL element that emits blue phosphorescence.
Japanese Patent No. 3093796 Japanese Unexamined Patent Publication No. 63-264692 JP-A-3-255190 US Pat. No. 6,097,147 M.M. A. Baldo et al. , Nature, 395, 151-154 (1998) M.M. A. Baldo et al. , Nature, 403, 17, 750-753 (2000) S. Lamansky et al. , J .; Am. Chem. Soc. , 123, 4304 (2001) M.M. E. Thompson et al. , The 10th International Works on Organic and Organic Electroluminescence (EL'00, Hamamatsu) Moon-Jae Youn. 0 g, Tsutsuo Tsutsui et al. , The 10th International Works on Organic and Organic Electroluminescence (EL'00, Hamamatsu) Ikai et al. , The 10th International Works on Organic and Organic Electroluminescence (EL'00, Hamamatsu)

The present invention has been made in view of the problems that written, solving problems of the present invention, an organic EL element material luminous efficiency is increased, the organic EL device using the organic EL element material, illumination device and It is to provide a display device. Furthermore, it is providing the organic EL element material which becomes long life, the organic EL element using this organic EL element material, an illuminating device, and a display apparatus.

The above object of the present invention is Ru are solved by the following means 15.

(Claim 1)
A material for an organic electroluminescence device, which is a compound represented by the following general formula (1).

〔式中、Ｒ _１８ およびＲ _１９ は、各々、下記一般式（９）で表される基を表す。〕

〔式中、Ｌは、アルキル基または芳香族炭化水素基を置換基として有してもよいフェニレン基、メチレン基またはシクロヘキシレン基から選ばれる１〜５つの基から構成される連結基を表す。
Ｒ _２０ 、Ｒ _２１ 、Ｒ _２３ およびＲ _２４ は、各々、水素原子、アルキル基または芳香族炭化水素基を表す。また、Ｒ _２２ は、下記一般式（９）で表される基を表す。〕

〔式中、Ｒ _２５ およびＲ _２６ は、各々、下記一般式（９）で表される基を表す。〕

〔式中、Ｚ１およびＺ２は、前記一般式（１）中のＺ１およびＺ２と同義である。〕
２．前記Ｚ１はベンゼン環が縮環してもよいピリジン環を形成する原子群を表し、前記Ｚ２はベンゼン環、ナフタレン環またはベンゼン環が縮環してもよいピリジン環を形成する原子群を表すことを特徴とする前記１に記載の有機エレクトロルミネッセンス素子用材料。
３．下記一般式（２）で表される化合物であることを特徴とする有機エレクトロルミネッセンス素子用材料。 [Wherein R ₁ represents a group represented by the following general formula (6), (7) or (8), and Z1 represents an atomic group forming a pyridine ring to which an aromatic hydrocarbon ring may be condensed. the stands, Z2 represents an atomic group forming an aromatic hydrocarbon ring or may pyridine ring optionally aromatic hydrocarbon ring condensed. Provided that at least one of the ring formed by each Z1 and Z2 is a fused aromatic hydrocarbon ring or fused aromatic heterocyclic ring. When R ₁ is a group represented by the following general formula (7), the general formula (1) has an axis of symmetry. ]

[Wherein, R ₁₈ and R ₁₉ each represent a group represented by the following general formula (9). ]

[In formula, L represents the coupling group comprised from 1-5 groups chosen from the phenylene group, the methylene group, or the cyclohexylene group which may have an alkyl group or an aromatic hydrocarbon group as a substituent.
R ₂₀ , R ₂₁ , R ₂₃ and R ₂₄ each represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group. R ₂₂ represents a group represented by the following general formula (9). ]

[Wherein, R ₂₅ and R ₂₆ each represent a group represented by the following general formula (9). ]

[In formula, Z1 and Z2 are synonymous with Z1 and Z2 in the said General formula (1). ]
2. Z1 represents an atomic group forming a pyridine ring to which a benzene ring may be condensed, and Z2 represents an atomic group forming a pyridine ring to which a benzene ring, a naphthalene ring or a benzene ring may be condensed. 2. The material for an organic electroluminescence element as described in 1 above.
3. A material for an organic electroluminescence device, which is a compound represented by the following general formula (2).

〔式中、Ｌは、アルキル基または芳香族炭化水素基を置換基として有してもよいフェニレン基、メチレン基またはシクロヘキシレン基から選ばれる１〜４つの基から構成される連結基を表す。
Ｒ _２０ 、Ｒ _２１ 、Ｒ _２３ およびＲ _２４ は、各々水素原子、アルキル基または芳香族炭化水素基を表す。また、Ｒ _２２ は、下記一般式（９）で表される基を表す。〕

〔式中、Ｚ１およびＺ２は、各々、前記一般式（２）中のＺ１およびＺ２と同義である。〕 [Wherein R ₂ , R ₃ , R ₅ and R ₆ each represent a hydrogen atom or a substituent, R ₄ represents a group represented by the following general formula (7), and Z 1 represents an aromatic hydrocarbon ring represents an atomic group forming a good pyridine ring condensed, Z2 represents an atomic group forming an aromatic hydrocarbon ring or aromatic optionally pyridine ring hydrocarbon rings are condensed. Provided that at least one of the ring formed by each Z1 and Z2 is a fused aromatic hydrocarbon ring or fused aromatic heterocyclic ring. The general formula (2) has an axis of symmetry. ]

[In formula, L represents the coupling group comprised from 1-4 groups chosen from the phenylene group, the methylene group, or the cyclohexylene group which may have an alkyl group or an aromatic hydrocarbon group as a substituent.
R ₂₀ , R ₂₁ , R ₂₃ and R ₂₄ each represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group. R ₂₂ represents a group represented by the following general formula (9). ]

[In formula, Z1 and Z2 are synonymous with Z1 and Z2 in the said General formula (2), respectively. ]

4). A material for an organic electroluminescence device, which is a compound represented by the following general formula (3).

〔式中、Ｌは、アルキル基または芳香族炭化水素基を置換基として有してもよいフェニレン基、メチレン基またはシクロヘキシレン基から選ばれる１〜４つの基から構成される連結基を表す。
Ｒ _２０ 、Ｒ _２１ 、Ｒ _２３ およびＲ _２４ は、各々水素原子、アルキル基または芳香族炭化水素基を表す。また、Ｒ _２２ は、下記一般式（９）で表される基を表す。〕

〔式中、Ｚ１は芳香族炭化水素環が縮環してもよいピリジン環を形成する原子群を表し、Ｚ２は、前記一般式（３）中のＺ２と同義である。〕
５．下記一般式（４）で表される化合物であることを特徴とする有機エレクトロルミネッセンス素子用材料。 [Wherein R ₂ , R ₃ , R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each represents a hydrogen atom or a substituent, and R ₄ represents a group represented by the following general formula (7) the stands, Z2 represents an atomic group forming an aromatic hydrocarbon ring or may pyridine ring optionally aromatic hydrocarbon ring condensed. However, when Z2 is not condensed, R ₇ and R ₈ are bonded to form a ring. The general formula (3) has an axis of symmetry. ]

[In formula, L represents the coupling group comprised from 1-4 groups chosen from the phenylene group, the methylene group, or the cyclohexylene group which may have an alkyl group or an aromatic hydrocarbon group as a substituent.
R ₂₀ , R ₂₁ , R ₂₃ and R ₂₄ each represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group. R ₂₂ represents a group represented by the following general formula (9). ]

[In the formula, Z1 represents an atomic group forming a pyridine ring to which an aromatic hydrocarbon ring may be condensed, and Z2 has the same meaning as Z2 in the general formula (3). ]
5. A material for an organic electroluminescence device, which is a compound represented by the following general formula (4).

〔式中、Ｌは、アルキル基または芳香族炭化水素基を置換基として有してもよいフェニレン基、メチレン基またはシクロヘキシレン基から選ばれる１〜４つの基から構成される連結基を表す。
Ｒ _２０ 、Ｒ _２１ 、Ｒ _２３ およびＲ _２４ は、各々水素原子、アルキル基または芳香族炭化水素基を表す。また、Ｒ _２２ は、下記一般式（９）で表される基を表す。〕

〔式中、Ｚ１は芳香族炭化水素環が縮環してもよいピリジン環を形成する原子群を表し、Ｚ２は、前記一般式（４）中のＺ２と同義である。〕
６．下記一般式（５）で表される化合物であることを特徴とする有機エレクトロルミネッセンス素子用材料。 [Wherein R ₂ , R ₃ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ and R ₁₃ each represents a hydrogen atom or a substituent, and R ₄ represents the following general formula (7 represents a group represented by), Z2 represents an atomic group forming an aromatic hydrocarbon ring or may pyridine ring optionally aromatic hydrocarbon ring condensed. The general formula (4) has an axis of symmetry. ]

[In formula, L represents the coupling group comprised from 1-4 groups chosen from the phenylene group, the methylene group, or the cyclohexylene group which may have an alkyl group or an aromatic hydrocarbon group as a substituent.
R ₂₀ , R ₂₁ , R ₂₃ and R ₂₄ each represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group. R ₂₂ represents a group represented by the following general formula (9). ]

[In formula, Z1 represents the atomic group which forms the pyridine ring which an aromatic hydrocarbon ring may be condensed, and Z2 is synonymous with Z2 in the said General formula (4). ]
6). A material for an organic electroluminescence device, which is a compound represented by the following general formula (5).

〔式中、Ｌは、アルキル基または芳香族炭化水素基を置換基として有してもよいフェニレン基、メチレン基またはシクロヘキシレン基から選ばれる１〜４つの基から構成される連結基を表す。
Ｒ _２０ 、Ｒ _２１ 、Ｒ _２３ およびＲ _２４ は、各々水素原子、アルキル基または芳香族炭化水素基を表す。また、Ｒ _２２ は、下記一般式（９）で表される基を表す。〕

〔式中、Ｚ１は芳香族炭化水素環が縮環してもよいピリジン環を形成する原子群を表し、Ｚ２は、前記一般式（５）中のＺ２と同義である。〕
７．前記１〜６のいずれか１項に記載の有機エレクトロルミネッセンス素子用材料を用いたことを特徴とする有機エレクトロルミネッセンス素子。 [Wherein R ₂ , R ₃ , R ₅ , R ₆ , R ₇ , R ₁₄ , R ₁₅ , R ₁₆ and R ₁₇ each represent a hydrogen atom or a substituent, and R ₄ represents the following general formula (7 represents a group represented by), Z2 represents an atomic group forming an aromatic hydrocarbon ring or may pyridine ring optionally aromatic hydrocarbon ring condensed. The general formula (5) has an axis of symmetry. ]

[In formula, L represents the coupling group comprised from 1-4 groups chosen from the phenylene group, the methylene group, or the cyclohexylene group which may have an alkyl group or an aromatic hydrocarbon group as a substituent.
R ₂₀ , R ₂₁ , R ₂₃ and R ₂₄ each represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group. R ₂₂ represents a group represented by the following general formula (9). ]

[In formula, Z1 represents the atomic group which forms the pyridine ring which an aromatic hydrocarbon ring may be condensed, and Z2 is synonymous with Z2 in the said General formula (5). ]
7). 7. An organic electroluminescent element using the organic electroluminescent element material according to any one of 1 to 6 above.

8). 8. The organic electroluminescence device as described in 7 above, wherein the organic electroluminescence device has a light emitting layer containing a phosphorescent compound as a constituent layer.

9. The organic electroluminescent device according to the organic electroluminescent device material as described in any one of the 1-6 in the 7 characterized by containing the light emitting layer.

10. 8. The organic electroluminescence device according to 7 above, which has a hole blocking layer containing the material for an organic electroluminescence device according to any one of 1 to 6 as a constituent layer.

11. 11. The organic electroluminescence element according to any one of 7 to 10 above, which emits blue light.

12 11. The organic electroluminescence element according to any one of 7 to 10 above, which emits white light.

13. A display device comprising the organic electroluminescence element according to any one of 7 to 12 above .

14 An illumination device comprising the organic electroluminescence element according to any one of 7 to 12 above .

15. 15. A display device comprising the illumination device according to 14 and a liquid crystal element as display means.

  According to the present invention, an organic EL element material with high luminous efficiency, an organic EL element using the organic EL element material, a lighting device, and a display device can be provided. Furthermore, it was possible to provide an organic EL element material having a long life, an organic EL element using the organic EL element material, an illumination device, and a display device.

  In the organic electroluminescence element of the present invention (hereinafter referred to as an organic EL element), by using at least one organic EL element material defined in any one of the above 1 to 7, the above 8 to 13 is used. It was possible to obtain an organic EL element having a high external extraction efficiency and a long driving life as defined in any one of the above. Moreover, the display apparatus and illumination apparatus which comprise the organic EL element of this invention were able to be provided collectively.

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

  The material for an organic EL device of the present invention is characterized by being a compound represented by any one of the general formulas (1) to (5), and each will be described below.

<< Compound Represented by Formula (1) >>
In the general formula (1), examples of the substituent represented by R ₁ include an alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group). Group, tridecyl 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.) Etc.), aryl groups (eg phenyl group, naphthyl group etc.), aromatic heterocyclic groups (eg furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, pyrazolyl group) , Thiazolyl group, quinazolinyl group, phthalazinyl group, etc.), heterocyclic group (eg , Pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.), alkoxyl group (for example, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxyl 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) Group, dodecylthio group, etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group (eg, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (eg, methyl) Ruoxycarbonyl group, ethyloxycarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (eg, phenyloxycarbonyl group, naphthyloxycarbonyl group, etc.), sulfamoyl group (eg, 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, pentylcarbonyl group, cyclo Xylcarbonyl 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, pentylcarbonylamino group, cyclohexylcarbonyl) Amino group, 2-ethylhexylcarbonylamino group, octylcarbonylamino group, dodecylcarbonylamino group, phenylcarbonylamino group, naphthy Carbonylamino 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, methylsulfinyl group, ethyls) Rufinyl 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 (phenylsulfonyl group, naphthylsulfonyl group, 2-pyridylsulfonyl group etc.), amino group (for example, amino group, ethyl group) Amino group, dimethylamino group, butylamino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, anilino group, naphthylamino group, 2-pyridyl Mino group etc.), halogen atom (eg fluorine atom, chlorine atom, bromine atom etc.), fluorinated hydrocarbon group (eg fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group etc.), And 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. In addition, a plurality of these substituents may be bonded to each other to form a ring.

In the general formula (1), each benzene ring represented by Z1 and Z2 may have a substituent represented by R ₁ in the general formula (1).

In the general formula (1), examples of the condensed aromatic hydrocarbon rings represented by Z1 and Z2 include naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, chrysene ring, naphthacene ring, triphenylene ring, Examples include an acenaphthene ring, a coronene ring, a fluorene ring, a fluoranthrene ring, a naphthacene ring, a pentacene ring, a perylene ring, a pentaphen ring, a picene ring, a pyrene ring, a pyranthrene ring, and an anthraanthrene ring. Furthermore, the condensed aromatic hydrocarbon ring may have a substituent represented by R ₁ in the general formula (1).

In the general formula (1), examples of the monocyclic aromatic heterocycle represented by Z1 and Z2 include a furan ring, a thiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an oxadiazole ring, A triazole ring, an imidazole ring, a pyrazole ring, a thiazole ring, etc. are mentioned. Furthermore, the monocyclic aromatic heterocycle may have a substituent represented by R ₁ in the general formula (1).

In the general formula (1), examples of the condensed aromatic heterocycle formed by the atomic groups represented by Z1 and Z2 include a benzimidazole ring, an indole ring, a benzimidazole ring, a benzothiazole ring, a benzoxazole ring, Quinoxaline ring, quinazoline ring, phthalazine ring, carbazole ring, carboline ring, diazacarbazole ring (showing a ring in which one of the carbon atoms of the hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom) . Furthermore, the condensed aromatic heterocyclic ring may have a substituent represented by R ₁ in the general formula (1).

  In general formula (1), as the ring formed by the atomic group represented by Z2, a naphthalene ring and a quinoline ring are preferably used.

<< Compound Represented by Formula (2) >>
In the general formula (2), each of the substituents represented by R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ has the same meaning as the substituent represented by R ₁ in the general formula (1).

  In the general formula (2), a benzene ring, a condensed aromatic hydrocarbon ring, a monocyclic aromatic heterocycle, and a condensed aromatic heterocycle formed by atomic groups represented by Z1 and Z2 are represented by the general formula (1). Are the same as a benzene ring, a condensed aromatic hydrocarbon ring, a monocyclic aromatic heterocyclic ring, and a condensed aromatic heterocyclic ring each formed by an atomic group represented by each of Z1 and Z2.

  In general formula (2), as the ring formed by the atomic group represented by Z2, a naphthalene ring and a quinoline ring are preferably used.

<< Compound Represented by Formula (3) >>
In general formula (3), each of the substituents represented by R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ is R ₁ in general formula (1). It is synonymous with the substituent represented.

  In the general formula (3), the condensed aromatic hydrocarbon ring and the condensed aromatic heterocyclic ring represented by Z2 are respectively the condensed aromatic hydrocarbon ring and the condensed aromatic ring each represented by Z1 and Z2 in the general formula (1). Synonymous with aromatic heterocycle.

<< Compound Represented by Formula (4) >>
In the general formula (4), R ₂ , R ₃ , R ₄ , R ₅ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , each of the substituents represented by the general formula (1) It is synonymous with the substituent represented by R < ₁ >.

  In the general formula (4), a benzene ring, a condensed aromatic hydrocarbon ring, a monocyclic aromatic heterocycle, and a condensed aromatic heterocycle formed by the atomic group represented by Z2 are each represented by the general formula (1). , Z1, and Z2, each having the same meaning as a benzene ring, a condensed aromatic hydrocarbon ring, a monocyclic aromatic heterocyclic ring, and a condensed aromatic heterocyclic ring.

<< Compound Represented by Formula (5) >>
In the general formula (5), each of the substituents represented by R ₂ , R ₃ , R ₄ , R ₅ , R ₇ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ in the general formula (1) It is synonymous with the substituent represented by R < ₁ >.

  In General Formula (5), a benzene ring, a condensed aromatic hydrocarbon ring, a monocyclic aromatic heterocycle, and a condensed aromatic heterocycle formed by the atomic group represented by Z2 are each represented by General Formula (1). , Z1, and Z2, each having the same meaning as a benzene ring, a condensed aromatic hydrocarbon ring, a monocyclic aromatic heterocyclic ring, and a condensed aromatic heterocyclic ring.

  Specific examples of the compounds represented by the general formulas (1) to (5) according to the present invention are shown below, but the present invention is not limited thereto.

  The compounds represented by the general formulas (1) to (5) according to the present invention can be synthesized or obtained with reference to conventionally known documents. Here, although an example of the synthesis example of the compound respectively represented by general formula (1)-(5) which concerns on this invention is shown, this invention is not limited to these.

  << Synthesis Example: Synthesis of Exemplary Compound A-1 >>

  0.16 g of palladium acetate and 0.58 g of tri-tert-butylphosphine were dissolved in 10 ml of anhydrous toluene, 25 mg of sodium borohydride was added and stirred at room temperature for 10 minutes, and then 2.60 g of intermediate a, 2. 41 g of intermediate b and 1.49 g of sodium tert-butoxide were dispersed in 50 ml of anhydrous xylene and stirred at reflux temperature for 10 hours under a nitrogen atmosphere. After allowing to cool, chloroform and water were added to separate the organic layer, the organic layer was washed with water and saturated brine, concentrated under reduced pressure, and the resulting residue was separated and purified by silica gel chromatography, 1.4 g of colorless crystals of exemplary compound A-1 were obtained.

The structure of Example Compound A-1 was confirmed by ¹ H-NMR spectrum and mass spectrometry spectrum. The spectral data of Example Compound A-1 are as follows.

MS (FAB) m / z: 587 (M + ¹ )
¹ H-NMR (400 MHz, CDCl ₃ )
δ / ppm: 7.35 (m, 2H), 7.53 (t, 1H), 7.6 (dd), 7.65 (d, 1H), 7.72 (d, 2H), 7.85 (D, 1H), 8.08 (m, 3H), 8.55 (d, 1H), 8.72 (dd, 1H)
The compounds represented by the general formulas (1) to (5) according to the present invention include organic EL element materials (backlight, flat panel display, illumination light source, display element, electrophotographic light source, recording light source, exposure light source). Used in applications such as reading light sources, signs, signboards, interiors, optical communication devices, etc., but other uses include materials for organic semiconductor lasers (recording light sources, exposure light sources, reading light source optical communication devices, electrophotography) Light source, etc.), electrophotographic photoreceptor material, organic TFT element material (organic memory element, organic arithmetic element, organic switching element), organic wavelength conversion element material, photoelectric conversion element material (solar cell, photosensor, etc.) ) And so on.

  Next, the constituent layers of the organic EL device of the present invention will be described in detail.

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 / light emitting layer / electron transport layer / cathode (ii) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (iii) Anode / hole transport layer / light emitting layer / hole blocking layer / electron Transport layer / cathode (iv) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode (v) anode / anode buffer layer / hole transport layer / light emitting layer / hole Blocking layer / electron transport layer / cathode buffer layer / cathode << Anode >>
As the anode in the organic EL element, an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO ₂ and ZnO. Alternatively, an amorphous material such as IDIXO (In ₂ O ₃ —ZnO) capable of forming a transparent conductive film may be used. For the anode, a thin film may be formed by depositing these electrode materials by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when the pattern accuracy is not required (100 μm or more) Degree), a pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. When light emission is extracted from the anode, it is desirable that the transmittance is 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 nm to 1000 nm, preferably 10 nm to 200 nm.

"cathode"
On the other hand, as the cathode, a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like. Among these, a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value than this, such as a magnesium / silver mixture, magnesium, from the viewpoint of electron injectability and durability against oxidation, etc. / Aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al ₂ O ₃ ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred. 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 nm to 5 μm, preferably 50 to 200 nm. In order to transmit the emitted light, if either the anode or the cathode of the organic EL element is transparent or translucent, the light emission luminance is improved, which is convenient.

  Moreover, after producing the said metal with a film thickness of 1-20 nm on a cathode, a transparent or semi-transparent cathode can be produced by producing the electroconductive transparent material quoted by description of the anode on it, By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.

  Next, an injection layer, a blocking layer, an electron transport layer and the like used as the constituent layers of the organic EL element of the present invention will be described.

<< Injection layer: electron injection layer, hole injection layer >>
The injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. You may let them.

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

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

  The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc. Metal buffer layer typified by lithium, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer layer typified by aluminum oxide, etc. . The buffer layer (injection layer) is desirably a very thin film, and although it depends on the material, the film thickness is preferably in the range of 0.1 nm to 5 μm.

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

  The hole blocking layer is an electron transport layer in a broad sense, and is made of a hole blocking 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.

  The hole blocking layer of the organic EL device of the present invention is provided adjacent to the light emitting layer.

  In this invention, it is preferable to contain the compound which concerns on this invention mentioned above as a hole blocking material of a hole blocking layer. Thereby, it can be set as an organic EL element with much higher luminous efficiency. Furthermore, the lifetime can be further increased.

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

<Light emitting layer>
The light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is in the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.

(Host compound)
The light emitting layer of the organic EL device of the present invention preferably contains a host compound and a phosphorescent compound (also referred to as a phosphorescent compound) shown below. It is preferable to use the compound according to the present invention. Thereby, the luminous efficiency can be further increased. Moreover, you may contain compounds other than the compound which concerns on said this invention as a host compound.

  Here, in the present invention, the host compound is defined as a compound having a phosphorescence quantum yield of phosphorescence emission of less than 0.01 at room temperature (25 ° C.) among compounds contained in the light emitting layer.

  Furthermore, a plurality of known host compounds may be used in combination. 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. Further, by using a plurality of types of phosphorescent compounds, it is possible to mix different light emission, thereby obtaining an arbitrary emission color. White light emission is possible by adjusting the kind of phosphorescent compound and the amount of doping, and can also be applied to illumination and backlight.

  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.

  Specific examples of known host compounds include compounds described in the following documents.

  JP-A-2001-257076, 2002-308855, 2001-313179, 2002-319491, 2001-357777, 2002-334786, 2002-8860, 2002-334787, 2002-15871, 2002-334788, 2002-43056, 2002-334789, 2002-75645, 2002-338579, 2002-105445 gazette, 2002-343568 gazette, 2002-141173 gazette, 2002-352957 gazette, 2002-203683 gazette, 2002-363227 gazette, 2002-231453 gazette, No. 003-3165, No. 2002-234888, No. 2003-27048, No. 2002-255934, No. 2002-286061, No. 2002-280183, No. 2002-299060, No. 2002. -302516, 2002-305083, 2002-305084, 2002-308837, and the like.

  Moreover, the light emitting layer may contain the host compound which has a fluorescence maximum wavelength further as a host compound. In this case, the energy transfer from the other host compound and the phosphorescent compound to the fluorescent compound allows the electroluminescence as the organic EL device to be emitted from the other host compound having the 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. Specific host compounds having a maximum fluorescence wavelength include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, and pyrylium dyes. Perylene dyes, stilbene dyes, polythiophene dyes, and the like. The fluorescence quantum yield can be measured by the method described in 362 (1992, Maruzen) of Spectroscopic II of the Fourth Edition Experimental Chemistry Course 7.

(Phosphorescent compound (phosphorescent compound))
As a material used for the light emitting layer (hereinafter referred to as a light emitting material), it is preferable to contain a phosphorescent compound simultaneously with the host compound. Thereby, it can be set as an organic EL element with higher luminous efficiency.

  The phosphorescent compound according to the present invention is a compound in which light emission from an excited triplet is observed, is a compound that emits phosphorescence at room temperature (25 ° C.), and has a phosphorescence quantum yield of 0 at 25 ° C. .01 or more compounds. The phosphorescence quantum yield is preferably 0.1 or more.

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

  There are two types of emission of phosphorescent compounds in principle. One is the recombination of carriers on the host compound to which carriers are transported, generating an excited state of the host compound, and this energy is phosphorescent. An energy transfer type in which light emission from the phosphorescent compound is obtained by transferring to the phosphorescent compound. The other is that the phosphorescent compound becomes a carrier trap, and carrier recombination occurs on the phosphorescent compound. Although it is a carrier trap type in which light emission from a phosphorescent compound can be obtained, in any case, the excited state energy of the phosphorescent compound is lower than the excited state energy of the host compound. is there.

  The phosphorescent compound can be appropriately selected from known compounds used for the light emitting layer of the organic EL device.

  The phosphorescent compound used in the present invention is preferably a complex compound containing a group 8-10 metal in the periodic table of elements, and more preferably an iridium compound, an osmium compound, or a platinum compound ( Platinum complex compounds) and rare earth complexes, most preferably iridium compounds.

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

  In the present invention, the phosphorescent maximum wavelength of the phosphorescent compound is not particularly limited, and in principle, by selecting a central metal, a ligand, a ligand substituent, and the like. Although the emission wavelength obtained can be changed, it is preferable that the phosphorescence emission wavelength of the phosphorescent compound has a maximum phosphorescence emission wavelength of 380 nm to 480 nm. With such a blue phosphorescent organic EL element and a white phosphorescent organic EL element, the luminous efficiency can be further increased.

  The light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with the total CS-1000 (manufactured by Minolta) is applied to the CIE chromaticity coordinates.

  The light emitting layer can be formed by forming the above compound by a known thinning method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or an ink jet method. Although the film thickness as a light emitting layer does not have a restriction | limiting in particular, Usually, 5 nm-5 micrometers, Preferably it is chosen in the range of 5 nm-200 nm. This light emitting layer may have a single layer structure in which these phosphorescent compounds or host compounds are composed of one kind or two or more kinds, or a laminated structure composed of a plurality of layers having the same composition or different compositions. Also good.

《Hole transport layer》
The hole transport layer is made of a hole transport 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 has any 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, stilbenes Derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, particularly thiophene oligomers, and the like can be given.

  As the hole transport material, those described above can be used, 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 two more described in US Pat. No. 5,061,569 Having a condensed aromatic ring of, 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.

  The 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, a printing method including an ink jet method, or an LB method. it can. Although there is no restriction | limiting in particular about the film thickness of a positive hole transport layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5 nm-200 nm. This 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 as a single layer or a plurality of layers.

  Conventionally, in the case of a single electron transport layer and a plurality of layers, an electron transport material (also serving as a hole blocking material) used for an electron transport layer adjacent to the light emitting layer on the cathode side is injected from the cathode. As long as it has a function of transferring electrons to the light-emitting layer, any material can be selected and used from among conventionally known compounds. For example, nitro-substituted fluorene derivatives, diphenylquinone derivatives Thiopyrandioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives and the like. Furthermore, in the above oxadiazole derivative, a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.

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

  In addition, metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum, Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc., and the central metals of these metal complexes are In, Mg, Cu , Ca, Sn, Ga, or Pb can also be used as an electron transport material. In addition, metal-free or metal phthalocyanine, or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material. In addition, the distyrylpyrazine derivative exemplified as the material of the light emitting layer can also be used as an electron transport material, and similarly to the hole injection layer and the hole transport layer, inorganic such as n-type-Si and n-type-SiC can be used. A semiconductor can also be used as an electron transport material.

  The 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, a printing method including 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, 5 nm-about 5 micrometers, Preferably it is 5 nm-200 nm. The electron transport layer may have a single layer structure composed of one or more of the above materials.

<Substrate>
The organic EL device of the present invention is preferably formed on a substrate.

  The substrate (hereinafter also referred to as a substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention is not particularly limited in the type of glass, plastic, etc. Although there is no restriction | limiting in particular, As a board | substrate used preferably, glass, quartz, and a transparent resin film can be mentioned, for example. 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. On the surface of the resin film, an inorganic film, an organic film, or a hybrid film of both may be formed.

  The external extraction efficiency at room temperature for light emission of the organic electroluminescence device of the present invention is preferably 1% or more, more preferably 5% 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.

  In addition, a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor. In the case of using a color conversion filter, the λmax of light emission of the organic EL element is preferably 480 nm or less.

<< 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 / electron transport layer / electron injection 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 nm to 200 nm, thereby producing an anode. To do. Next, an organic compound thin film of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a hole blocking layer, which are organic EL element materials, is formed thereon.

As a method for thinning the organic compound thin film, there are a vapor deposition method and a wet process (spin coating method, casting method, ink jet method, printing method) as described above, but it is easy to obtain a uniform film and a pinhole. From the point of being difficult to form, a vacuum deposition method, a spin coating method, an ink jet method, and a printing method are particularly preferable. Further, different film forming methods may be applied for each layer. When a vapor deposition method is employed for film formation, the vapor deposition conditions vary depending on the type of compound used, but generally a boat heating temperature of 50 ° C. to 450 ° C., a vacuum degree of 10 ⁻⁶ Pa to 10 ⁻² Pa, and a vapor deposition rate of 0 It is desirable to select appropriately within the range of 0.01 nm / second to 50 nm / second, substrate temperature −50 ° C. to 300 ° C., film thickness 0.1 nm to 5 μm, preferably 5 nm to 200 nm.

  After forming these layers, 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 nm to 200 nm, and a cathode is provided. Thus, a desired organic EL element can be obtained. The organic EL element is preferably produced from the hole injection layer to the cathode consistently by a single evacuation, but may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.

  The multicolor display device of the present invention is provided with a shadow mask only when the light emitting layer is formed, and the other layers are common, so that patterning of the shadow mask or the like is not necessary. A film can be formed by a method or a printing method.

  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.

  In addition, it is also possible to reverse the production order and produce the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection 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. An alternating voltage may be applied. The alternating current waveform to be applied may be arbitrary.

  The display device of the present invention can be used as a display device, a display, and various light emission sources. In a display device or a 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.

  The lighting device of the present invention includes home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light sensors Although a light source etc. are mentioned, it is not limited to this.

  In addition, the organic EL element of the present invention may be used as an organic EL element having a resonator structure.

  Examples of the purpose of use of the organic EL element having such a resonator structure include a light source of an optical storage medium, a light source of an electrophotographic copying machine, a light source of an optical communication processing machine, and a light source of an optical sensor. It is not limited. Moreover, you may use for the said use by making a laser oscillation.

<Display device>
The organic EL element of the present invention may be used as one 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). When used as a display device for reproducing moving images, the driving method 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 three or more organic EL elements of the present invention having different emission colors. Alternatively, it is possible to make one color emission color, for example, white emission, into BGR by using a color filter to achieve full color. Furthermore, it is possible to convert the emission color of the organic EL to another color by using a color conversion filter, and in this case, λmax of the organic EL emission is preferably 480 nm or less.

  An example of a display device composed of organic EL elements will be described below with reference to the drawings.

  FIG. 1 is a schematic diagram illustrating an example of a display device including 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 the plurality of pixels based on image information from the outside. The pixels for each scanning line are converted into image data signals by the scanning signal. In response to this, light is sequentially emitted and image scanning is performed to display image information 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. FIG. 2 shows a case where the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).

  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 grid pattern and are connected to the pixels 3 at orthogonal positions (details are shown in FIG. Not shown).

  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 that emit light 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 power supply line 7 connects to the organic EL element 10 according to the potential of the image data signal applied to the gate. Current is supplied.

  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 according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.

  That is, the organic EL element 10 emits light by the switching transistor 11 and the drive transistor 12 that are active elements for the organic EL element 10 of each of the plurality of pixels, and the light emission of the organic EL element 10 of each of the plurality of pixels 3. It is carried out. 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 on / off of a predetermined light emission amount by a binary image data signal. But you can.

  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 view 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.

  The organic EL material according to the present invention can also 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. As a combination of a plurality of luminescent colors, those containing three luminescence maximum wavelengths of three primary colors of blue, green, and blue may be used. The thing containing the light emission maximum wavelength may be used.

  In addition, a combination of light emitting materials for obtaining a plurality of emission colors includes a combination of a plurality of phosphorescent or fluorescent materials (light emitting dopants), a light emitting material that emits fluorescent or phosphorescent light, and the light emission. Any combination of a dye material that emits light from the material as excitation light may be used, but in the white organic electroluminescence device according to the present invention, a method of combining a plurality of light-emitting dopants is preferable.

  As a layer structure of an organic electroluminescence device for obtaining a plurality of emission colors, a method of having a plurality of emission dopants in one emission layer, a plurality of emission layers, and an emission wavelength in each emission layer And a method of forming minute pixels emitting light having different wavelengths in a matrix.

  In the white organic electroluminescence device according to the present invention, patterning may be performed by a metal mask, an ink jet printing method, or the like at the time of film formation, if necessary. When patterning, only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire element layer may be patterned.

  The light emitting material used for the light emitting layer is not particularly limited. For example, in the case of a backlight in a liquid crystal display element, the platinum complex according to the present invention is known so as to be suitable for the wavelength range corresponding to the CF (color filter) characteristics. Any one of the light emitting materials may be selected and combined to be whitened.

  As described above, the light-emitting organic EL element of the present invention that emits white light is used as a kind of lamp such as a home lighting, an interior lighting, and an exposure light source as various light emitting sources and lighting devices in addition to the display device and the display. Further, it is also useful for display devices such as backlights for liquid crystal display devices.

  Others such as backlights for watches, billboard advertisements, traffic lights, 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, the embodiment of this invention is not limited to these.

  The structural formulas of the compounds used in the examples are as follows.

Example 1
<< Production of Organic EL Element 1-1 >>
Transparent support provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass) made of ITO (indium tin oxide) with a thickness of 100 nm on a glass substrate of 100 mm × 100 mm × 1.1 mm as an anode The substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes. This transparent support substrate is fixed to a substrate holder of a commercially available vacuum vapor deposition apparatus. Meanwhile, 200 mg of α-NPD is put into a molybdenum resistance heating boat, and 200 mg of compound A-12 as a host compound is put into another molybdenum resistance heating boat. 200 mg of bathocuproin (BCP) is put into another resistance heating boat made of molybdenum, 100 mg of Ir-12 is put into another resistance heating boat made of molybdenum, and 200 mg of Alq ₃ is put into another resistance heating boat made of molybdenum. Installed on.

Next, after the pressure in the vacuum chamber was reduced to 4 × 10 ⁻⁴ Pa, the heating boat containing α-NPD was energized and heated, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second. The hole transport layer was provided. Further, the heating boat containing the compounds A-12 and Ir-12 was energized and heated, and co-deposited on the hole transport layer at a deposition rate of 0.2 nm / second and 0.012 nm / second, respectively. A light emitting layer having a thickness of 40 nm was provided. In addition, the substrate temperature at the time of vapor deposition was room temperature. Furthermore, the heating boat containing BCP was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide a 10 nm thick hole blocking layer. Further, the heating boat containing Alq ₃ is further energized and heated, and deposited on the hole blocking layer at a deposition rate of 0.1 nm / second to further provide an electron transport layer having a thickness of 40 nm. It was. In addition, the substrate temperature at the time of vapor deposition was room temperature.

  Then, 0.5 nm of lithium fluoride and 110 nm of aluminum were vapor-deposited, the cathode was formed, and the organic EL element 1-1 was produced.

  Further, the organic EL element was transferred to a glove box under nitrogen atmosphere (a glove box substituted with high-purity nitrogen gas with a purity of 99.999% or more) without being exposed to the atmosphere, and the interior as shown in FIG. The organic EL element 1-1 was produced with the sealing structure replaced with 1.

  In addition, barium oxide 105 which is a water trapping agent is a glass-sealed can 104 made of high-purity barium oxide powder manufactured by Aldrich with a fluororesin-based semipermeable membrane (Microtex S-NTF8031Q made by Nitto Denko) with an adhesive. The material pasted on was prepared and used in advance. An ultraviolet curable adhesive 107 was used for bonding the sealing can and the organic EL element, and both were bonded to each other by irradiation with an ultraviolet lamp to produce a sealing element.

  In FIG. 5, 101 is a glass substrate provided with a transparent electrode, 102 is an organic EL layer composed of the hole injection / transport layer, light emitting layer, hole blocking layer, electron transport layer, and the like, and 103 is a cathode.

<< Production of Organic EL Elements 1-2 to 1-13 >>
Further, in the production of the organic EL element 1-1, the organic EL elements 1-2 to 1 were similarly performed except that the compound 1 used as the host compound of the light emitting layer was replaced with the compound shown in Table 1 to obtain a host compound. -13 was produced. The structure of the compound used above is shown below.

<< Evaluation of Organic EL Elements 1-1 to 1-13 >>
The organic EL elements 1-1 to 1-13 were evaluated as follows.

《External extraction quantum efficiency》
About the produced organic EL element, the external extraction quantum efficiency (%) when a ^2.5 mA / cm ² constant current was applied in a dry nitrogen gas atmosphere at 23 ° C. was measured. For the measurement, a spectral radiance meter CS-1000 (manufactured by Minolta) was used in the same manner.

  The measurement results of the external extraction quantum efficiency in Table 1 are expressed as relative values when the measured value of the organic EL element 1-13 is 100.

"lifespan"
When driving at a constant current of ^2.5 mA / cm ² , the time required for the luminance to drop to half of the luminance immediately after the start of light emission (initial luminance) is measured, and the lifetime is determined as the half-life time (τ 0.5). It was used as an index. For the measurement, a spectral radiance meter CS-1000 (manufactured by Minolta) was used. Moreover, the measurement result of the lifetime of Table 1 was represented by the relative value when the organic EL element 1-13 was set to 100.

  The obtained results are shown in Table 1.

  From Table 1, it is clear that the organic EL device of the present invention has an improved external quantum efficiency and a longer life than the comparative device.

Example 2
<< Preparation of Organic EL Element 2-1 >>
Transparent support provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass) made of ITO (indium tin oxide) with a thickness of 100 nm on a glass substrate of 100 mm × 100 mm × 1.1 mm as an anode The substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes. This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus. Meanwhile, 200 mg of α-NPD is put into a molybdenum resistance heating boat, 200 mg of CBP is put into another resistance heating boat made of molybdenum, and another resistance made of molybdenum. 200 mg of compound A-1 as a hole blocking material is put in a heating boat, 100 mg of Ir-1 is put in another resistance heating boat made of molybdenum, and 200 mg of Alq ₃ is put in another resistance heating boat made of molybdenum. Installed.

Next, after the pressure in the vacuum chamber was reduced to 4 × 10 ⁻⁴ Pa, the heating boat containing α-NPD was energized and heated, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second. The hole transport layer was provided. Further, the heating boat containing CBP and Ir-1 was energized and heated, and co-deposited on the hole transport layer at a deposition rate of 0.2 nm / second and 0.012 nm / second, respectively, to obtain a film thickness of 30 nm. The light emitting layer was provided. In addition, the substrate temperature at the time of vapor deposition was room temperature. Further, the heating boat containing the compound A-1 was energized and heated, and was deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide a 10 nm thick hole blocking layer. Further, the heating boat containing Alq ₃ is further energized and heated, and deposited on the hole blocking layer at a deposition rate of 0.1 nm / second to further provide an electron transport layer having a thickness of 40 nm. It was. In addition, the substrate temperature at the time of vapor deposition was room temperature.

  Subsequently, 0.5 nm of lithium fluoride and 110 nm of aluminum were vapor-deposited to form a cathode, and an organic EL element 2-1 was produced.

<< Production of Organic EL Elements 2-2 to 2-15 >>
In the production of the organic EL element 2-1, the compound A-1 used as the hole blocking material was replaced with the compound shown in Table 2 in the same manner as the organic EL element 2-1, 2-2 to 2-15. Was made.

<Evaluation of organic EL elements 2-1 to 2-15>
The external extraction quantum efficiency of the organic EL elements 2-1 to 2-15 was evaluated in the same manner as in Example 1. Furthermore, the lifetime was evaluated according to the measurement method shown below.

(lifespan)
When driving at a constant current of ^2.5 mA / cm ² , the time required for the luminance to drop to half of the luminance immediately after the start of light emission (initial luminance) is measured, and the lifetime is determined as the half-life time (τ 0.5). It was used as an index. For the measurement, a spectral radiance meter CS-1000 (manufactured by Minolta) was used.

  The measurement results of external extraction quantum efficiency and lifetime in Table 2 are expressed as relative values when the organic EL element 2-15 is set to 100.

  From Table 2, it is clear that the organic EL element of the present invention has improved external extraction quantum efficiency and a longer life than the comparative element.

Example 3
The organic EL element 1-3 of the present invention produced in Example 1, the organic EL element 2-4 of the present invention produced in Example 2, and the phosphorescent compound of the organic EL element 1-3 of the present invention A red light-emitting organic EL element produced in the same manner except that it was replaced with Ir-9 (also referred to as Btp ₂ Ir (acac)) was juxtaposed on the same substrate to produce an active matrix type full-color display device shown in FIG. FIG. 2 shows only a schematic diagram of the display portion A of the produced full-color display device. That is, a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of juxtaposed pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) on the same substrate. Each of the scanning lines 5 and the plurality of data lines 6 in the wiring portion is 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 (details). Is 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. Then, an image data signal is received from the data line 6 and light is emitted according to the received image data. In this way, full-color display is possible by appropriately juxtaposing the red, green, and blue pixels.

  By driving the full-color display device, a clear full-color moving image display with high external extraction quantum efficiency and good durability was obtained.

Example 4
<Production of 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 50 nm thereon as in Example 1, and further according to the present invention. The heating boat containing the compound A-27, which is the organic EL element material, the boat containing Ir-12, and the boat containing Ir-9 (also referred to as Btp ₂ Ir (acac)) were energized independently. The film thickness was adjusted to 100: 5: 0.6 by adjusting the deposition rate of Compound A-3 as a luminescent host and Ir-12 and Ir-9 as luminescent dopants (also referred to as Btp ₂ Ir (acac)) to a film thickness of 30 nm. The light emitting layer was provided by vapor deposition so as to have a thickness of 1 mm.

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

  Next, the vacuum chamber is opened, and a square perforated mask having the same shape as the stainless steel transparent electrode is placed on the electron transport layer, and 0.5 nm of lithium fluoride is deposited as the cathode buffer layer and 110 nm of aluminum is deposited as the cathode. A film was formed.

  The non-light-emitting surface of the obtained organic EL element W was covered with a glass case to obtain an illumination device (planar lamp) shown in FIGS. 6 (a) and 6 (b).

  When this flat lamp was energized, almost white light was obtained, and it was found that the flat lamp can be used as a thin illuminating device that emits white light with high luminous efficiency and long emission life. It has been found that even when the light emitting host is replaced with another compound of the present invention, white light emission can be obtained.

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 an equivalent circuit diagram of the drive circuit which comprises a pixel. It is a schematic diagram of the display apparatus by a passive matrix system. It is a schematic diagram of the sealing structure of the organic EL element 1-1. It is a schematic diagram of the illuminating device which comprises an organic EL element.

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 101 Glass substrate with a transparent electrode 102 Organic EL layer 103 Cathode 104 Glass sealing can 105 Barium oxide (water trapping agent)
106 Nitrogen gas 107 UV curable adhesive

Claims (15)

A material for an organic electroluminescence device, which is a compound represented by the following general formula (1).

[Wherein R ₁ represents a group represented by the following general formula (6), (7) or (8), and Z1 represents an atomic group forming a pyridine ring to which an aromatic hydrocarbon ring may be condensed. the stands, Z2 represents an atomic group forming an aromatic hydrocarbon ring or may pyridine ring optionally aromatic hydrocarbon ring condensed. Provided that at least one of the ring formed by each Z1 and Z2 are fused aromatic hydrocarbon ring or fused aromatic heterocyclic ring. When R ₁ is a group represented by the following general formula (7), the general formula (1) has an axis of symmetry. ]

[Wherein, R ₁₈ and R ₁₉ each represent a group represented by the following general formula (9). ]

[In formula, L represents the coupling group comprised from 1-5 groups chosen from the phenylene group, the methylene group, or the cyclohexylene group which may have an alkyl group or an aromatic hydrocarbon group as a substituent.
R ₂₀ , R ₂₁ , R ₂₃ and R ₂₄ each represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group. R ₂₂ represents a group represented by the following general formula (9). ]

[Wherein, R ₂₅ and R ₂₆ each represent a group represented by the following general formula (9). ]

[In formula, Z1 and Z2 are synonymous with Z1 and Z2 in the said General formula (1). ] Z1 represents an atomic group forming a pyridine ring to which a benzene ring may be condensed, and Z2 represents an atomic group forming a pyridine ring to which a benzene ring, a naphthalene ring or a benzene ring may be condensed. The material for an organic electroluminescence element according to claim 1. A material for an organic electroluminescence device, which is a compound represented by the following general formula (2).

[Wherein R ₂ , R ₃ , R ₅ and R ₆ each represent a hydrogen atom or a substituent, R ₄ represents a group represented by the following general formula (7), and Z 1 represents an aromatic hydrocarbon ring represents an atomic group forming a good pyridine ring condensed, Z2 represents an atomic group forming an aromatic hydrocarbon ring or aromatic optionally pyridine ring hydrocarbon rings are condensed. Provided that at least one of the ring formed by each Z1 and Z2 is a fused aromatic hydrocarbon ring or fused aromatic heterocyclic ring. The general formula (2) has an axis of symmetry. ]

[In formula, L represents the coupling group comprised from 1-4 groups chosen from the phenylene group, the methylene group, or the cyclohexylene group which may have an alkyl group or an aromatic hydrocarbon group as a substituent.
R ₂₀ , R ₂₁ , R ₂₃ and R ₂₄ each represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group. R ₂₂ represents a group represented by the following general formula (9). ]

[In formula, Z1 and Z2 are synonymous with Z1 and Z2 in the said General formula (2), respectively. ] A material for an organic electroluminescence device, which is a compound represented by the following general formula (3).

[Wherein R ₂ , R ₃ , R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each represents a hydrogen atom or a substituent, and R ₄ represents a group represented by the following general formula (7) the stands, Z2 represents an atomic group forming an aromatic hydrocarbon ring or may pyridine ring optionally aromatic hydrocarbon ring condensed. However, when Z2 is not condensed, R ₇ and R ₈ are bonded to form a ring. The general formula (3) has an axis of symmetry. ]

[In formula, L represents the coupling group comprised from 1-4 groups chosen from the phenylene group, the methylene group, or the cyclohexylene group which may have an alkyl group or an aromatic hydrocarbon group as a substituent.
R ₂₀ , R ₂₁ , R ₂₃ and R ₂₄ each represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group. R ₂₂ represents a group represented by the following general formula (9). ]

[In the formula, Z1 represents an atomic group forming a pyridine ring to which an aromatic hydrocarbon ring may be condensed, and Z2 has the same meaning as Z2 in the general formula (3). ] A material for an organic electroluminescence device, which is a compound represented by the following general formula (4).

[Wherein R ₂ , R ₃ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ and R ₁₃ each represents a hydrogen atom or a substituent, and R ₄ represents the following general formula (7 represents a group represented by), Z2 represents an atomic group forming an aromatic hydrocarbon ring or may pyridine ring optionally aromatic hydrocarbon ring condensed. The general formula (4) has an axis of symmetry. ]

[In formula, L represents the coupling group comprised from 1-4 groups chosen from the phenylene group, the methylene group, or the cyclohexylene group which may have an alkyl group or an aromatic hydrocarbon group as a substituent.
R ₂₀ , R ₂₁ , R ₂₃ and R ₂₄ each represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group. R ₂₂ represents a group represented by the following general formula (9). ]

[In formula, Z1 represents the atomic group which forms the pyridine ring which an aromatic hydrocarbon ring may be condensed, and Z2 is synonymous with Z2 in the said General formula (4). ] A material for an organic electroluminescence device, which is a compound represented by the following general formula (5).

[Wherein R ₂ , R ₃ , R ₅ , R ₆ , R ₇ , R ₁₄ , R ₁₅ , R ₁₆ and R ₁₇ each represent a hydrogen atom or a substituent, and R ₄ represents the following general formula ( represents a group represented by 7), Z2 represents an atomic group forming a good pyridine ring condensed aromatic hydrocarbon ring or aromatic hydrocarbon ring,. The general formula (5) has an axis of symmetry. ]

[In formula, L represents the coupling group comprised from 1-4 groups chosen from the phenylene group, the methylene group, or the cyclohexylene group which may have an alkyl group or an aromatic hydrocarbon group as a substituent.
R ₂₀ , R ₂₁ , R ₂₃ and R ₂₄ each represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group. R ₂₂ represents a group represented by the following general formula (9). ]

[In formula, Z1 represents the atomic group which forms the pyridine ring which an aromatic hydrocarbon ring may be condensed, and Z2 is synonymous with Z2 in the said General formula (5). ] The organic electroluminescent element using the organic electroluminescent element material of any one of Claims 1-6. The organic electroluminescence device according to claim 7, comprising a light emitting layer containing a phosphorescent compound as a constituent layer. The organic electroluminescent element according to any one of claims 1 to 6, wherein the light emitting layer contains the material for an organic electroluminescent element according to any one of claims 1 to 6. The organic electroluminescence device according to claim 7, comprising a hole blocking layer containing the material for an organic electroluminescence device according to claim 1 as a constituent layer. The organic electroluminescence element according to any one of claims 7 to 10, which emits blue light. The organic electroluminescence device according to claim 7, which emits white light. A display device comprising the organic electroluminescence element according to claim 7. An illuminating device comprising the organic electroluminescence element according to any one of claims 7 to 12. 15. A display device comprising: the lighting device according to claim 14; and a liquid crystal element as display means.

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