JP2006152101A - Organic electroluminescent element material, organic electroluminescent element, displaying device and lighting device - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic EL (electroluminescent) element showing a high light-emitting efficiency and having a long light-emitting life, a light-emitting device and a displaying device. <P>SOLUTION: This organic electroluminescent element is characterized by containing at least 1 kind of an ortho metal complex of gold. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to an organic electroluminescence element material, 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 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, and injects electrons and holes into the light emitting layer and recombines them to generate excitons. 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 V to several tens V, and is self-luminous. Therefore, 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.

  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 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.

  As described above, when light emission from excited singlet is used, the generation ratio of singlet excitons and triplet excitons is 1: 3, and thus the generation probability of luminescent excited species is 25%. Since the efficiency is about 20%, the limit of the external extraction quantum efficiency (ηext) was set to 5%.

  However, since Princeton University reported on organic EL devices using phosphorescence emission from excited triplets (MA Baldo et al., Nature, 395, 151-154 (1998)), at room temperature. 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 excited triplets are used, the upper limit of internal quantum efficiency is 100%, so that in principle the luminous efficiency is four times that of excited singlets, and there is a possibility that almost the same performance as cold cathode tubes 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 have been studied for synthesis centering on heavy metal complexes such as iridium complexes.

  In addition, the aforementioned M.I. A. Baldo et al. , Nature, Vol. 403, No. 17, pages 750-753 (2000), studies have been made using tris (2-phenylpyridine) iridium as a dopant.

In addition, M.M. E. Thompson et al., In The 10th International Works on Inorganic and Organic Electroluminescence (EL'00, Hamamatsu), used L ₂ Ir (acac), for example (ppy) ₂ Ir (acac) as a dopant, 0 g, Tetsuo Tsutsui, etc., again, The 10th International Workshop on Inorganic and Organic Electroluminescence (EL'00, Hamamatsu) in, as a dopant tris (2-(p-tolyl) pyridine) iridium (Ir (ptpy) _3), Studies using tris (benzo [h] quinoline) iridium (Ir (bzq) ₃ ) and the like are being conducted (note that these metal complexes are generally called orthometalated iridium complexes).

  In addition, S. Lamansky et al. , J .; Am. Chem. Soc. , 123, 4304 (2001), etc., attempts have been made to form devices using various iridium complexes.

  In order to obtain high luminous efficiency, in the 10th International Works on Inorganic and Organic Electroluminescence (EL'00, Hamamatsu), Ikai et al. Uses a hole transporting compound as a host of a phosphorescent compound. In addition, M.M. E. Thompson et al. Use various electron transporting materials as a host of a phosphorescent compound, doped with a novel iridium complex.

  Orthometalated complexes in which the central metal is platinum instead of iridium are also attracting attention. With regard to this type of complex, there are many known examples in which a ligand is characterized (see, for example, Patent Documents 1 to 5 and Non-Patent Document 1).

  In any case, the light emission luminance and light emission efficiency of the light emitting device are greatly improved compared to conventional devices because the emitted light is derived from phosphorescence. There was a problem that it was lower than the conventional element. As described above, phosphorescent high-efficiency light-emitting materials are not capable of sufficiently achieving practical performance because it is difficult to shorten the emission wavelength and improve the light emission lifetime of the device.

  Regarding wavelength shortening, introduction of electron-withdrawing groups such as fluorine atoms, trifluoromethyl groups, and cyano groups into phenylpyridine as substituents, and introduction of picolinic acid and pyrazabole-based ligands as ligands (For example, refer to Patent Documents 6 to 10 and Non-Patent Documents 1 to 4.) With these ligands, the emission wavelength of the light-emitting material is shortened to achieve blue, and high efficiency. While the device can be achieved, the light emission lifetime of the device is greatly deteriorated, and thus improvement of the trade-off has been demanded.

Some examples have also been presented regarding light-emitting complexes in which the central metal is gold. (For example, refer to Patent Documents 6 and 11 to 14), there has been a demand for further improving the luminous efficiency and extending the luminous lifetime.
JP 2002-332291 A JP 2002-332292 A JP 2002-338588 A JP 2002-226495 A JP 2002-234894 A International Publication No. 02/15645 Pamphlet JP 2003-123982 A JP 2002-117978 A JP 2003-146996 A International Publication No. 04/016711 Pamphlet JP 2004-131463 A JP 2004-131464 A JP 2004-158297 A JP 2004-175799 A Inorganic Chemistry, Vol. 41, No. 12, pp. 3055-3066 (2002) Applied Physics Letters, Volume 79, 2082 (2001) Applied Physics Letters, 83, 3818 (2003) New Journal of Chemistry, 26, 1171 (2002)

  The present invention has been made in view of the above problems, and an object of the present invention is to provide an organic EL element, a lighting device, and a display device that have a light emission wavelength controlled, exhibit high light emission efficiency, and have a long light emission lifetime. That is.

  The above object of the present invention has been achieved by the following constitutions 1 to 51.

(Claim 1)
An organic electroluminescent element material comprising at least one gold orthometal complex selected from a partial structure group consisting of the following general formulas (1) to (6).

[Wherein, X ₁₀ represents a carbon atom or a nitrogen atom, and Q ₁₁ together with the carbon atom and X ₁₀ forms a 6-membered aromatic hydrocarbon ring or a 5-membered to 6-membered aromatic heterocycle. Represents an atomic group. X ₁₁ , X ₁₂ , X ₁₃ and X ₁₄ each represent C—R ₁₁ , N, N—R ₁₁ , O or S, and together with the nitrogen atom form a 5-membered aromatic heterocycle. R ₁₁ represents a hydrogen atom or a substituent. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]

[Wherein, X ₂₀ represents a carbon atom or a nitrogen atom, and Q ₁₂ represents an atom that forms a 6-membered aromatic hydrocarbon ring or a 5-membered to 6-membered aromatic heterocyclic ring together with the carbon atom and X _20. Represents a group. X ₂₁ , X ₂₂ , X ₂₃ and X ₂₄ each represent C—R ₂₁ or N, and together with the nitrogen atom form a 6-membered aromatic heterocycle. R ₂₁ represents a hydrogen atom or a substituent. However, at least one of X _{21 to} X ₂₄ represents N. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]

[Wherein, X ₃₀ represents a carbon atom or a nitrogen atom, and Q ₁₃ represents an atom that forms a 6-membered aromatic hydrocarbon ring or a 5-membered to 6-membered aromatic heterocyclic ring together with the carbon atom and X _30. Represents a group. R ₃₁ represents a substituent. n3 represents an integer of 0 to 3. However, when n3> 1, the plurality of R ₃₁ may be the same as or different from each other. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]

[Wherein, R ₄₁ and R ₄₂ each represent a substituent, and m4 and n4 each represent an integer of 0 to 3. Xa represents -N (Ra) ₂ , -O-Ra or -S-Ra. Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. When Xa is —N (Ra) ₂ , the two Ras may be the same or different. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]

[Wherein, X ₅₁ , X ₅₂ , X ₅₃ and X ₅₄ each represent a carbon atom or a nitrogen atom, and Q ₁₄ represents a carbon atom, a 6-membered aromatic hydrocarbon ring together with X ₅₁ and X ₅₃ , or 5 The atomic group which forms a 6-membered aromatic heterocyclic ring is represented. Q ₁₅ forms a 5-membered to 6-membered aromatic heterocyclic ring together with the carbon atom, X ₅₂ , X ₅₄ and nitrogen atom. X _b and X _c each represents a substituent. m5 and n5 each represents 0 or 1. However, m5 + n5 ≧ 1. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]

[Wherein, X ₆₁ , X ₆₂ , X ₆₃ , X ₆₄ each represents a carbon atom or a nitrogen atom, Q ₁₆ represents a carbon atom, a six-membered aromatic hydrocarbon ring together with X ₆₁ , X ₆₂ , or 5 The atomic group which forms a 6-membered aromatic heterocyclic ring is represented. Q ₁₇ forms a 5-membered or 6-membered aromatic heterocycle together with the carbon atom, X ₆₃ , X ₆₄ and nitrogen atom. X _c and X _d each represents a substituent. m6 and n6 each represents 0 or 1. However, m6 + n6 ≧ 1. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]
(Claim 2)
An organic electroluminescent device material comprising at least one trivalent gold orthometal complex selected from the group consisting of the following general formulas (A), (B) and (C).

Wherein, A _1, A ₂ each represent a carbon atom or a nitrogen atom, Q ₁ is an aromatic heterocyclic ring aromatic hydrocarbon ring 6 membered together with a carbon atom and A ₁ or 5-6 membered, Represents an atomic group forming Q ₂ represents an atomic group that forms a 5-membered to 6-membered aromatic heterocyclic ring together with the nitrogen atom and A ₂ . Q ₁ and Q ₂ constitute a ligand which is bonded to each other via A ₁ and A ₂ to form a trivalent gold orthometal complex, and X ₁ and X ₂ may be the same or different. Represents a monovalent anionic monodentate ligand. X ₃ and X ₄ each represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and together with L ₁ form a minus monovalent anionic bidentate ligand. X ₅ and X ₆ each represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and together with L ₂ form a negative divalent anionic bidentate ligand. Z ⁻ represents a monovalent anion. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]
(Claim 3)
An organic electroluminescence element material comprising a monovalent gold orthometal complex represented by the following general formula (D) or (E):

Wherein, A _1, A ₂ each represent a carbon atom or a nitrogen atom, Q ₁ is an aromatic heterocyclic ring aromatic hydrocarbon ring 6 membered together with a carbon atom and A ₁ or 5-6 membered, Represents an atomic group forming Q ₂ forms a 5- or 6-membered aromatic heterocycle with the nitrogen atom and A ₂ . Q ₁ and Q ₂ constitute a ligand that is bonded to each other via A ₁ and A ₂ to form a monovalent gold ortho metal complex. X ₇ represents an uncharged monodentate ligand, X ₈ represents a minus monovalent anionic monodentate ligand, and Y ⁺ represents a monovalent cation. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]
(Claim 4)
It contains at least one partial structure selected from a partial structure group consisting of the following general formulas 1-1 to 1-150 or a tautomer of the partial structure as a partial structure, and contains a gold orthometal complex. The organic electroluminescent element material according to any one of claims 1 to 3.

[Wherein, R ₁₃ and R ₁₄ each represent a substituent, and n11 and n12 each represent an integer of 0 to 2. X ₁₅ and X ₁₆ each represent> N—R ₁₅ , —O— or —S—. R ₁₅ represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X ₁₇ and X ₁₈ each represent> N—R ₁₆ , —O— or —S—. R ₁₆ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X _19a , X _19b and X _19c each represent CH or N, and any one or two of them are N. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]
(Claim 5)
Containing at least one kind of orthometal complex having at least one partial structure selected from the partial structure group consisting of the following general formulas 2-1 to 2-50 or a tautomer of the partial structure as a partial structure The organic electroluminescent element material according to any one of claims 1 to 3.

[Wherein, R ₂₂ and R ₂₃ each represent a substituent, and n21 and n22 each represents an integer selected from 0 to 2. X ₂₅ represents> N—R ₂₄ , —O— or —S—. R ₂₄ represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X ₂₆ represents> N—R ₂₅ , —O— or —S—. R ₂₅ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X ₂₇ , X ₂₈ , and X ₂₉ each represent CH or N, and any one or two are N. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). _{2 -, - C (= O} ) -, - C (= NR) -, - S (O) -, or, -SO ₂ - represents a. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]
(Claim 6)
Containing at least one partial structure selected from the partial structure group consisting of the following general formulas 3-1 to 3-10, or an orthometal complex characterized by having a tautomer of the partial structure as a partial structure The organic electroluminescent element material according to any one of claims 1 to 3.

[Wherein, R ₃₂ and R ₃₃ each represent a substituent, and n31 and n32 each represents an integer selected from 0 to 2. X ₃₁ represents> N—R ₂₄ , —O— or —S—. R ₂₄ represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X ₃₂ represents> N—R ₂₅ , —O— or —S—. R ₂₅ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X ₃₃ , X ₃₄ , and X ₃₅ each represent CH or N, and any one or two are N. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). _{2 -, - C (= O} ) -, - C (= NR) -, - S (O) -, or, -SO ₂ - represents a. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]
(Claim 7)
An ortho-metal complex having a partial structure represented by the following general formula (7) or (8) or a tautomer of the partial structure as a partial structure: Organic electroluminescent element material of any one of these.

[Wherein, R ₅₁ , R ₅₂ , R ₅₃ and R ₅₄ each represent a hydrogen atom or an electron-donating substituent, and at least one of them is an electron-donating substituent. R ₅₆ , R ₅₇ , R ₅₈ and R ₅₉ each represent a hydrogen atom or a substituent, and at least one of R ₅₆ and R ₅₈ is an electron-withdrawing substituent. R ₅₅ represents a substituent, n5 is an integer selected from 0-3. Xa represents -N (Ra) ₂ , -O-Ra or -S-Ra. Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. When Xa is —N (Ra) ₂ , the two Ras may be the same or different. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]
(Claim 8)
The organic material according to any one of claims 1 to 3, comprising an orthometal complex having a partial structure represented by the following general formula (9) or a tautomer of the partial structure as a partial structure. Electroluminescence element material.

[Wherein, X ₅₆ , X ₅₇ , X ₅₈ and X ₅₉ each represent a carbon atom or a nitrogen atom, and Q ₁₈ represents a carbon atom, X ₅₆ and X ₅₇ together with a 6-membered aromatic hydrocarbon ring, or 5 Q ₁₉ represents an atomic group that forms a 5-membered to 6-membered aromatic heterocyclic ring together with a carbon atom, X ₅₈ , X ₅₉ , and a nitrogen atom. To express. X _f and X _g represent a substituent having a van der Waals volume of 20 mm or more. m1 and n1 represent 0 or 1. However, m1 + n1 ≧ 1. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]
(Claim 9)
The ortho metal complex which has the partial structure represented by following General formula (10) or the tautomer of this partial structure as a partial structure is contained, The any one of Claims 1-3 characterized by the above-mentioned. Organic electroluminescence element material.

[In the formula, X ₆₆ , X ₆₇ , X ₆₈ and X ₆₉ each represent a carbon atom or a nitrogen atom, and Q ₂₀ represents a carbon atom, a six-membered aromatic hydrocarbon ring together with X ₆₆ and X ₆₇ , or 5 Q ₂₁ represents an atomic group that forms a 5- to 6-membered aromatic heterocyclic ring together with a carbon atom, X ₆₈ , X ₆₉ , and a nitrogen atom. To express. X _h and X _k represent a substituent having a van der Waals volume of 20 mm or more. m2 and n2 each represents 0 or 1. However, m2 + n2 ≧ 1.
X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). _{2 -, - C (= O} ) -, - C (= NR) -, - S (O) -, or, -SO ₂ - represents a. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]
(Claim 10)
2. An orthometal complex having at least one partial structure selected from the group consisting of the following general formulas (11) to (14) or a tautomer of the partial structure as a partial structure. The organic electroluminescent element material of any one of -3.

[Wherein, X ₇₁ , X ₇₂ , X ₇₃ and X ₇₄ each represent a carbon atom or a nitrogen atom, Q ₂₂ represents a carbon atom, a 6-membered aromatic hydrocarbon ring together with X ₇₁ and X ₇₂ , or a 5-membered Represents an atomic group that forms a 6-membered aromatic heterocyclic ring, and Q ₂₃ represents an atomic group that forms a 5-membered to 6-membered aromatic heterocyclic ring with a carbon atom, X ₇₃ , X ₇₄ , and a nitrogen atom. Q ₂₄ forms an aromatic hydrocarbon ring or an aromatic heterocyclic ring together with the carbon atom. Q ₂₅ forms an aromatic heterocycle with the nitrogen atom. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). _{2 -, - C (= O} ) -, - C (= NR) -, - S (O) -, or, -SO ₂ - represents a. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]
(Claim 11)
The organic electroluminescent element material according to claim 2, wherein X ₁ and X _{2 in} the general formula (A) are each an anion selected from the following group.

[Wherein, R ₆₁ represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R ₆₂ represents a substituent, n8 represents an integer of 0 to 3. ]
(Claim 12)
The minus monovalent bidentate ligand formed by X ₃ -L ₁ -X ₄ of the general formula (B) is selected from the following partial structures or partial structures represented by tautomers of the partial structures The organic electroluminescent element material according to claim 2, wherein

[Wherein R ₆₃ , R ₆₄ and R ₆₆ each represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R ₆₅ represents a substituent, n9 is an integer of 0 to 3, n10 represents an integer of 0 to 2. R ₆₇ represents R ₆₈ —CO— or R ₆₈ —SO ₂ —, and R ₆₈ represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. Q ₂₈ forms a 5- to 6-membered aromatic heterocycle with carbon and nitrogen. Q ₂₉ and Q ₃₀ each represents an atomic group that forms a 5-membered aromatic heterocycle with carbon and nitrogen. ]
(Claim 13)
From the partial structure which the minus bivalent bidentate ligand formed by X < ₅ > -L < ₂ > -X < ₆ > of the said general formula (C) represents with the partial structure quoted below or the tautomer of this partial structure. The organic electroluminescence device material according to claim 2, wherein the material is selected.

[Wherein R ₆₉ , R ₇₀ , R ₇₁ and R ₇₂ each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. nA represents 1 or 2. R ₇₃ and R ₇₄ each represent R ₇₈ —CO— or R ₇₈ —SO ₂ —, and R ₇₈ represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R ₇₅ , R ₇₆ and R ₇₇ each represents a substituent, and nB represents 0 or 1. nC and nD represent an integer selected from 0 to 2. X ₈₁ , X ₈₂ , X ₈₃ , X ₈₄ , X ₈₅ , and X ₈₆ are selected from C—R ₇₉ and N, and together with a carbon atom and a nitrogen atom, form a 5-membered heteroaromatic ring. R ₇₉ represents a hydrogen atom or a substituent. ]
(Claim 14)
Wherein X ₇ of the general formula (D) The organic electroluminescent device material according to any one of claims 1-3, characterized in that selected from uncharged ligands below.

[Wherein, R ₈₀ , R ₈₂ , R ₈₃ , R ₈₄ and R ₈₅ each represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R ₈₁ represents a substituent, and nE represents an integer of 0-2. ]
(Claim 15)
The organic electroluminescence element material according to any one of claims 1 to 3, wherein X _{8 in the} general formula (E) is selected from the following anion group.

[Wherein R ₈₆ represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R ₈₇ represents a substituent, and nF represents an integer selected from 0 to 3. ]
(Claim 16)
The organic electroluminescent element material containing the organic electroluminescent element material of any one of Claims 1-15.

(Claim 17)
An organic electroluminescent device comprising a light emitting layer as a constituent layer, wherein the light emitting layer contains the organic electroluminescent device material according to any one of claims 1 to 15.

(Claim 18)
An organic electroluminescence device comprising a hole blocking layer as a constituent layer, wherein the hole blocking layer contains the organic electroluminescence device material according to any one of claims 1 to 15.

(Claim 19)
The organic electroluminescent element according to any one of claims 16 to 18, comprising a compound represented by the following general formula (33) in a light emitting layer or a layer adjacent to the light emitting layer.

[Wherein, Z ₁ represents an aromatic heterocyclic ring which may have a substituent, Z ₂ represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring which may each have a substituent, Z ₃ represents a divalent linking group or a simple bond. R ₁₀₁ represents a hydrogen atom or a substituent. ]
(Claim 20)
20. The organic electroluminescence device according to claim 19, wherein Z _{1 of the} compound represented by the general formula (33) is a 6-membered ring.

(Claim 21)
21. The organic electroluminescence device according to claim 19, wherein Z _{2 of the} compound represented by the general formula (33) is a 6-membered ring.

(Claim 22)
The organic electroluminescence device according to any one of claims 19 to 21, wherein Z _{3 of the} compound represented by the general formula (33) is a bond.

(Claim 23)
23. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) has a molecular weight of 450 or more.

(Claim 24)
24. The organic electroluminescent element according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-1).

[Wherein, R _{501 to} R ₅₀₇ each independently represents a hydrogen atom or a substituent. ]
(Claim 25)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-2).

[Wherein, R _{511 to} R ₅₁₇ each independently represents a hydrogen atom or a substituent. ]
(Claim 26)
The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (33-3).

[Wherein, R _{521 to} R ₅₂₇ each independently represents a hydrogen atom or a substituent. ]
(Claim 27)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-4).

[Wherein, R _{531 to} R ₅₃₇ each independently represents a hydrogen atom or a substituent. ]
(Claim 28)
24. The organic electroluminescent element according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-5).

Wherein, R ₅₄₁ to R ₅₄₈ each independently represents a hydrogen atom or a substituent. ]
(Claim 29)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-6).

[Wherein, R _{551 to} R ₅₅₈ each independently represents a hydrogen atom or a substituent. ]
(Claim 30)
24. The organic electroluminescent element according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-7).

[Wherein, R _{561 to} R ₅₆₇ each independently represents a hydrogen atom or a substituent. ]
(Claim 31)
The compound represented by the general formula (33) is represented by the following general formula (33-8), The organic electroluminescence device according to any one of claims 19 to 23.

[Wherein, R _{571 to} R ₅₇₇ each independently represents a hydrogen atom or a substituent. ]
(Claim 32)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-9).

[Wherein, R _{581 to} R ₅₈₈ each represents a hydrogen atom or a substituent. ]
(Claim 33)
24. The organic electroluminescent element according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-10).

[Wherein, R _{591 to} R ₅₉₈ each represent a hydrogen atom or a substituent. ]
(Claim 34)
The compound represented by the general formula (33) has at least one group represented by any one of the following general formulas (34-1) to (34-8). Organic electroluminescent element of any one of these.

[In the formula, R _{502 to} R ₅₀₇ , R _{512 to} R ₅₁₇ , R _{522 to} R ₅₂₇ , R _{532 to} R ₅₃₇ , R _{542 to} R ₅₄₈ , R _{552 to} R ₅₅₈ , R _{562 to} R ₅₆₇ , R _{572 to} R ₅₇₇ each independently represents a hydrogen atom or a substituent, and the substituents may be the same or different. ]
(Claim 35)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (35).

[Wherein, R _{601 to} R ₆₀₆ each independently represents a hydrogen atom or a substituent, and at least one of R _{601 to} R ₆₀₆ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ]
(Claim 36)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (36).

[Wherein, R _{611 to} R ₆₂₀ each independently represents a hydrogen atom or a substituent, and at least one of R _{611 to} R ₆₂₀ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ]
(Claim 37)
The compound represented by the general formula (33) is represented by the following general formula (37), The organic electroluminescence device according to any one of claims 19 to 23.

[Wherein, R _{621 to} R ₆₂₃ each independently represents a hydrogen atom or a substituent, and at least one of R _{621 to} R ₆₂₃ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ]
(Claim 38)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (38).

[Wherein, R _{631 to} R ₆₄₅ each independently represent a hydrogen atom or a substituent, and at least one of R _{631 to} R ₆₄₅ is represented by the above general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ]
(Claim 39)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (39).

[Wherein, R _{651 to} R ₆₅₆ each independently represents a hydrogen atom or a substituent, and at least one of R _{651 to} R ₆₅₆ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. na represents an integer of 0 to 5, and nb represents an integer of 1 to 6, but the sum of na and nb is 6. ]
(Claim 40)
The compound represented by the general formula (33) is represented by the following general formula (40), The organic electroluminescence device according to any one of claims 19 to 23.

[Wherein, R _{661 to} R ₆₇₂ each independently represents a hydrogen atom or a substituent, and at least one of R _{661 to} R ₆₇₂ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ]
(Claim 41)
The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (41).

[Wherein, R _{681 to} R ₆₈₈ each independently represents a hydrogen atom or a substituent, and at least one of R _{681 to} R ₆₈₈ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ]
(Claim 42)
The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (42).

[Wherein, R _{691 to} R ₇₀₀ each independently represents a hydrogen atom or a substituent, and L ₁ represents a divalent linking group. At least one of R _{691 to} R ₇₀₀ represents at least one group selected from the groups represented by the general formulas (34-1) to (34-4). ]
(Claim 43)
The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (43).

[Wherein, R ₁ and R ₂ each independently represents a hydrogen atom or a substituent. n and m each represent an integer of 1 to 2, and k and l each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. ]
(Claim 44)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (44).

[Wherein, R ₁ and R ₂ each independently represents a hydrogen atom or a substituent. n and m each represent an integer of 1 to 2, and k and l each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. ]
(Claim 45)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (45).

[Wherein, R ₁ and R ₂ each independently represents a hydrogen atom or a substituent. n and m each represent an integer of 1 to 2, and k and l each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. ]
(Claim 46)
The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (46).

[Wherein, R ₁ and R ₂ each independently represents a hydrogen atom or a substituent. n and m each represent an integer of 1 to 2, and k and l each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. ]
(Claim 47)
The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (47).

[Wherein, R ₁ and R ₂ each independently represents a hydrogen atom or a substituent. n and m each represent an integer of 1 to 2, and k and l each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. Z ₁ , Z ₂ , Z ₃ and Z ₄ each represents a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom. ]
(Claim 48)
The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (48).

[Wherein, o and p each represent an integer of 1 to 3, and Ar ₁ and Ar ₂ each represent an arylene group or a divalent aromatic heterocyclic group. Z ₁ and Z ₂ each represent a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom, and L represents a divalent linking group. ]
(Claim 49)
24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (49).

[Wherein, o and p each represent an integer of 1 to 3, and Ar ₁ and Ar ₂ each represent a divalent arylene group or a divalent aromatic heterocyclic group. Z ₁ , Z ₂ , Z ₃ and Z ₄ each represents a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom, and L represents a divalent linking group. ]
(Claim 50)
A display device comprising the organic electroluminescent element according to claim 16.

(Claim 51)
An illuminating device comprising the organic electroluminescence element according to any one of claims 16 to 49.

  According to the present invention, it was possible to provide an organic EL element, a lighting device, and a display device that exhibit high luminous efficiency and have a long light emission lifetime.

  In the organic electroluminescence device (hereinafter also referred to as organic EL) material of the present invention, the external extraction quantum efficiency is high by designing the molecule so as to have the structure defined in any one of claims 1 to 15. In addition, an organic EL device having a high light emission lifetime could be obtained. In addition, using the organic EL element, a display device and a lighting device exhibiting high luminance and high luminous efficiency could be provided together.

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

  As a result of intensive studies on the problems of conventional orthometalated complexes having platinum complexes and gold complexes as central metals, the present inventors have found that heteroelement-containing bisaryl having a specific structure as a ligand of the gold complex. Organic EL devices fabricated using compounds and using a three-coordinate complex or a four-coordinate complex (gold orthometalated complex) having a planar structure exhibit higher luminous efficiency than conventional ones and have an emission lifetime. Has been found to be significantly improved.

《Gold ortho-metal complex》
Each of the gold orthometal complexes according to the organic EL element material of the present invention will be described.

  When the ortho metal complex of gold according to the present invention is used in the organic EL element of the present invention, any layer of the organic EL element (for the layer structure of the organic EL element of the present invention) However, it is preferably used for the light emitting layer and / or the hole blocking layer, and when contained in the light emitting layer, as a light emitting dopant in the light emitting layer. By using it, it is possible to improve the light emission luminance and light emission efficiency of the organic EL device of the present invention and to prolong the light emission life.

<< A gold ortho metal complex having a partial structure selected from the general formulas (1) to (6) >>
The gold orthometal complex having a partial structure selected from the general formulas (1) to (6) will be described.

<< Compound Represented by Formula (1) >>
In the general formula (1), examples of the 6-membered aromatic hydrocarbon ring formed by Q ₁₁ together with the carbon atom and X ₁₀ include a benzene ring.

In the general formula (1), Q ₁₁ is, as the aromatic heterocyclic 5- to 6-membered to form together with the carbon atoms and X _10, an oxazole ring, a thiophene ring, a furan ring, pyrrole ring, pyridine ring, pyridazine ring, Examples include a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, a pyrazole ring, and a triazole ring.

In the general formula (1), a 6-membered aromatic hydrocarbon ring formed by Q ₁₁ together with the carbon atom and X _{10 is} a 5-membered to 6-membered aromatic heterocyclic ring, which will be described later. ) May have a substituent represented by R ₁₁ , and the substituents on the aromatic hydrocarbon ring or aromatic heterocyclic ring form a ring structure to form a condensed ring structure. It is also possible.

In the general formula (1), X ₀ is —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R) ₂ —, or —C. When (= NR)-is represented, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group, and an aromatic heterocyclic group represented by R are each represented by the following general formula (1). , R ₁₁ and the same as the alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group and aromatic heterocyclic group of the substituent. Also, further, it may have a substituent group represented by R _11.

In the general formula (1), examples of the 5-membered aromatic heterocycle formed by X ₁₁ , X ₁₂ , X ₁₃ and X ₁₄ together with a nitrogen atom include an oxazole ring, an imidazole ring, a pyrazole ring and a thiazole ring. It is done.

In the general formula (1), when X ₁₁ , X ₁₂ , X ₁₃ and X ₁₄ each represent C—R ₁₁ or N—R ₁₁ , examples of the substituent represented by R ₁₁ 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, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (for example, cyclopentyl) Group, cyclohexyl group, etc.), alkenyl group (for example, vinyl group, allyl group, etc.), alkynyl group (for example, propargyl group, etc.), aryl group (also called aromatic hydrocarbon ring group, for example, phenyl group, tolyl group, Xylyl group, naphthyl group, biphenylyl group, anthryl group, phenanthryl group, etc.), heterocyclic group (for example, pyrrolidyl group, imidazolidyl group, morpholy Group, oxazolidyl group, etc.), aromatic heterocyclic 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, dibenzothienyl group, indolyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group (in which one of the carbon atoms constituting the carboline ring is replaced by a nitrogen atom) ), Quinoxalinyl group, pyridazinyl group, triazini Group, quinazolinyl group, phthalazinyl group, etc.), alkoxyl group (eg, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxyl group (eg, cyclopentyl) Oxy 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 (for example, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group (for example, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (for example, methyloxycarbonyl group, ethylo group) Xycarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (eg, phenyloxycarbonyl group, naphthyloxycarbonyl group, etc.), sulfamoyl group (eg, aminosulfonyl group, methyl) Aminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octylaminosulfonyl group, dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2-pyridylaminosulfonyl group, etc. ), Ureido groups (for example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octylureido group, dodecyl) Raid group, phenylureido group, naphthylureido group, 2-pyridylaminoureido group, etc.), acyl group (for example, acetyl group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group, cyclohexylcarbonyl group, octylcarbonyl group, 2-ethylhexyl) Carbonyl 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 groups (eg, methylcarbonylamino group, ethylcarbonylamino group, dimethylcarbonylamino group, propylcarbonylamino group, pen Rucarbonylamino group, cyclohexylcarbonylamino group, 2-ethylhexylcarbonylamino group, octylcarbonylamino group, dodecylcarbonylamino group, phenylcarbonylamino group, naphthylcarbonylamino group, etc.), carbamoyl group (for example, aminocarbonyl group, methylamino) Carbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexylaminocarbonyl group, octylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, dodecylaminocarbonyl group, phenylaminocarbonyl group, naphthylaminocarbonyl group, 2-pyridylaminocarbonyl group, etc.), sulfinyl groups (for example, methylsulfinyl group, ethylsulfinyl group, butylsulfinyl group) Nyl group, cyclohexylsulfinyl group, 2-ethylhexylsulfinyl group, dodecylsulfinyl group, phenylsulfinyl group, naphthylsulfinyl group, 2-pyridylsulfinyl group, etc.), alkylsulfonyl group or arylsulfonyl group (for example, methylsulfonyl group, ethylsulfonyl group) , Butylsulfonyl group, cyclohexylsulfonyl group, 2-ethylhexylsulfonyl group, dodecylsulfonyl group, phenylsulfonyl group, naphthylsulfonyl group, 2-pyridylsulfonyl group, etc.), amino group (for example, amino group, ethylamino group, dimethylamino group) Butylamino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, anilino group, naphthylamino group, 2-pyridylamino group, etc.), nitro group, shear Group, and the like.

The substituent represented by R ₁₁ may further have a substituent, and the aryl group (also referred to as an aromatic hydrocarbon group) may further include an aryl group (also referred to as an aromatic hydrocarbon group). The aromatic heterocyclic group or the like can be substituted to form a condensed ring structure.

<< Compound Represented by Formula (2) >>
In general formula (2), Q ₁₂ forms together with the carbon atom and X ₂₀ , a 6-membered aromatic hydrocarbon ring, a 5-membered to 6-membered aromatic heterocyclic ring, etc. are each represented by Q in general formula (1). Synonymous with ₁₁ .

In the general formula (2), X ₂₁ , X ₂₂ , X ₂₃ , and X ₂₄ are respectively synonymous with X ₁₁ , X ₁₂ , X ₁₃ , and X _{14 in} the general formula (1).

In the general formula (2), the group represented by X _0, in the general formula (1), it is synonymous with the groups represented by X _0.

In the general formula (2), the substituent represented by R ₂₁ has the same definition as the substituent represented by R ₁₁ in the general formula (1).

<< Compound Represented by Formula (3) >>
In the general formula (3), Q ₁₃ is formed together with the carbon atom and X ₃₀ , the 6-membered aromatic hydrocarbon ring, the 5-membered to 6-membered aromatic heterocyclic ring, etc. Synonymous with ₁₁ .

In the general formula (2), the group represented by X _0, in the general formula (1), it is synonymous with the groups represented by X _0.

In the general formula (3), the substituent represented by R ₃₁ has the same meaning as the substituent represented by R ₁₁ in the general formula (1).

<< Compound Represented by Formula (4) >>
In the general formula (4), the substituents represented by R ₄₁ and R ₄₂ are respectively synonymous with the substituent represented by R ₁₁ in the general formula (1).

In —N (Ra) ₂ , —O—Ra or —S—Ra represented by Xa in the general formula (4), examples of the alkyl group represented by Ra include a methyl group, an ethyl group, and a propyl group. Isopropyl group, (t) butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group and the like.

  Examples of the cycloalkyl group represented by Ra in the general formula (4) include a cyclopentyl group and a cyclohexyl group.

  As an alkenyl group represented by Ra of General formula (4), a vinyl group, an allyl group, etc. are mentioned, for example.

  Examples of the aryl group represented by Ra in the general formula (4) include a phenyl group, a tolyl group, a xylyl group, a naphthyl group, a biphenylyl group, an anthryl group, and a phenanthryl group.

  Examples of the heterocyclic group represented by Ra in the general formula (4) include a pyrrolidyl group, an imidazolidyl group, a morpholyl group, and an oxazolidyl group.

  Examples of the aromatic heterocyclic group represented by Ra in the general formula (4) include, 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, dibenzothienyl group, indolyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group (one of the carbon atoms constituting the carboline ring is a nitrogen atom ), Quinoxalinyl group, pyridazinyl group, Azinyl group, quinazolinyl group, and phthalazinyl group.

In the general formula (4), the group represented by X _0, in the general formula (1), it is synonymous with the groups represented by X _0.

<< Compound Represented by Formula (5) >>
In the general formula (5), Q ₁₄ forms together with the carbon atom, X ₅₁ , X ₅₃ , the 6-membered aromatic hydrocarbon ring, 5-membered to 6-membered aromatic heterocycle, etc. ) Q ₁₁ .

In the general formula (5), the 5-membered to 6-membered aromatic heterocycle formed by Q ₁₅ together with X ₅₂ , X ₅₄ and a nitrogen atom is an aromatic heterocycle formed by Q _{11 in the} general formula (1). It is synonymous with.

In General Formula (5), the substituents represented by X _b and X _c have the same meaning as R _{11 in} General Formula (1).

In the general formula (5), the group represented by X _0, in the general formula (1), it is synonymous with the groups represented by X _0.

<< Compound Represented by Formula (6) >>
In the general formula (6), Q ₁₆ forms together with the carbon atom, X ₆₁ , X ₆₃ , the 6-membered aromatic hydrocarbon ring, 5-membered to 6-membered aromatic heterocycle, etc. ) Q ₁₁ .

In the general formula (6), the 5-membered or 6-membered aromatic heterocycle formed by Q ₁₇ together with the carbon atom, X ₆₂ , X ₆₄ and nitrogen atom has the same meaning as Q _{11 in the} general formula (1). .

In the general formula (6), the substituents represented by X _c and X _d have the same meaning as the substituent represented by R ₁₁ in the general formula (1).

In the general formula (6), the group represented by X ₀ are the compounds of formula (1), is synonymous with the groups represented by X _0.

<< A trivalent gold orthometal complex selected from the general formulas (A), (B) and (C) >>
In the general formulas (A), (B), and (C), Q ₁ forms together with the carbon atom and A ₁ , a 6-membered aromatic hydrocarbon ring and a 5- to 6-membered aromatic heterocyclic ring are each the same meaning as Q ₁₁ in formula (1).

Formula (A), in (B), (C), Q ₂ is an aromatic heterocyclic 5- to 6-membered to form together with the nitrogen atom and A ₂ is a Q ₁₁ as defined in formula (1) is there.

In general formula (A), in (B), (C), the group represented by X _0, in the general formula (1), it is synonymous with the groups represented by X _0.

<< Orthometalated complex of trivalent gold represented by formula (A) >>
In the general formula (A), the minus monovalent anionic monodentate ligand represented by X ₁ or X ₂ is preferably the anion according to claim 11, wherein the anion is represented by R ₆₁ . An alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, an aromatic heterocyclic group and the like have the same meanings as Ra in the general formula (4). Further, the substituent represented by R ₆₂ are the compounds of formula (1), it is synonymous with the substituents represented by R _11. A conventionally known minus monovalent anionic monodentate ligand can also be used.

<< Orthometalated complex of trivalent gold represented by formula (B) >>
In the general formula (B), X ₃ and X ₄ each represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, but together with L ₁ , a negative monovalent formed by X ₃ -L ₁ -X ₄ As the anionic bidentate ligand, the minus monovalent bidentate ligand described in claim 12 is preferable. In the bidentate ligand, an alkyl represented by R ₆₃ , R ₆₄ , R ₆₆ is used. The group, cycloalkyl group, aryl group, heterocyclic group, aromatic heterocyclic group and the like have the same meaning as each group represented by Ra in the general formula (4). Further, the substituent represented by R ₆₅ are the compounds of formula (1), it is synonymous with the substituents represented by R _11.

In a preferred embodiment of the general formula (B), R ₆₇ represents R ₆₈ —CO— or R ₆₈ —SO ₂ —, and the alkyl group, cycloalkyl group, aryl group, heterocyclic group represented by R ₆₈ , An aromatic heterocyclic group etc. are synonymous with each group represented by Ra of General formula (4).

In a preferred embodiment of the general formula (B), Q ₂₈ is, carbon, aromatic heterocyclic 5- to 6-membered forming together with the nitrogen has the same meaning as Q ₁₁ in formula (1).

In a preferred embodiment of the general formula (B), a 5-membered aromatic heterocycle formed by Q ₂₉ and Q ₃₀ together with carbon and nitrogen has the same meaning as Q _{11 in the} general formula (1).

In the general formula (B), a conventionally known anionic bidentate ligand can also be used as the minus monovalent anionic bidentate ligand formed by X ₃ -L ₁ -X ₄ . .

In the general formula (B), Z ^- shows the preferred embodiment below.

In the formula, R ₈₈ represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group, and these are synonymous with each group represented by Ra in the general formula (4). .

R ₈₉ , R ₉₀ , R ₉₁ and R ₉₂ represent an aryl group or an aromatic heterocyclic group, and these are synonymous with each group represented by Ra in the general formula (4). .

<< Orthometalated complex of trivalent gold represented by formula (C) >>
In a preferred embodiment of the general formula (C), X ₅ and X ₆ are each a negative divalent formed by X ₅ -L ₂ -X ₆ together with L ₂ together with a carbon atom, nitrogen atom, oxygen atom or sulfur atom. As the bidentate ligand, the alkyl group, the cycloalkyl group, the aryl group, the heterocyclic group, and the aromatic group represented by R ₆₉ , R ₇₀ , R ₇₁ , and R ₇₂ described in claim 13, respectively, are represented. A heterocyclic group etc. are synonymous with each group represented by Ra of General formula (4).

In a preferred embodiment of the general formula (C), R ₇₃ and R ₇₄ each represent R ₇₈ —CO— or R ₇₈ —SO ₂ —, and the alkyl group, cycloalkyl group, aryl group represented by R ₇₈ , Heterocyclic group, aromatic heterocyclic group and the like have the same meaning as each group represented by Ra in formula (4).

In a preferred embodiment of the general formula (C), the substituents represented by R ₇₅ , R ₇₆ and R ₇₇ have the same meaning as the substituent represented by R ₁₁ in the general formula (1).

In a preferred embodiment of the general formula (C), X ₈₁ , X ₈₂ , X ₈₃ , X ₈₄ , X ₈₅ , X ₈₆ are selected from C—R ₇₉ or N and are formed with a carbon atom or a nitrogen atom. The ˜6-membered aromatic heterocycle has the same meaning as that represented by Q ₁₁ in the general formula (1). The substituent represented by R ₇₉ has the same meaning as the substituent represented by R ₁₁ in the general formula (1).

  In the present invention, a conventionally known anionic bidentate ligand can also be used.

<< Monovalent Gold Orthometal Complex Represented by Formula (D) or (E) >>
In general formulas (D) and (E), Q ₁ forms together with the carbon atom and A ₁ a 6-membered aromatic hydrocarbon ring, 5-membered to 6-membered aromatic heterocycle, etc. 1) it is synonymous with Q ₁₁ of.

In General Formulas (D) and (E), the 5-membered or 6-membered aromatic heterocycle formed by Q ₂ together with the nitrogen atom and A ₂ has the same meaning as Q _{11 in} General Formula (1).

In the general formulas (D) and (E), an uncharged monodentate ligand represented by X ₇ , a minus monovalent anionic monodentate ligand represented by X ₈ , etc. are each a conventionally known coordination. It can be appropriately selected from the children and used.

In a preferred embodiment of the uncharged monodentate ligand represented by X ₇ in the general formula (D), an alkyl group represented by R ₈₀ , R ₈₂ , R ₈₃ , R ₈₄ and R ₈₅ , An alkyl group, an aryl group, a heterocyclic group, an aromatic heterocyclic group, etc. are synonymous with each group represented by Ra of General formula (4).

In a preferred embodiment of the uncharged monodentate ligand represented by X ₇ in the general formula (D), the substituent represented by R ₈₁ is the substituent represented by R ₁₁ in the general formula (1). It is synonymous with.

In a preferred embodiment of the minus monovalent anionic monodentate ligand represented by X ₈ in the general formula (E), an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, an aromatic group represented by R ₈₆ The group heterocyclic group and the like are synonymous with each group represented by Ra in the general formula (4). Further, the substituent represented by R ₈₇ has the same meaning as the substituent represented by R ₁₁ in the general formula (1).

In the general formula (E), examples of the monovalent cation represented by Y ⁺ include those shown below.

In the formula, R ₉₃ and R ₉₄ represent an alkyl group, a cycloalkyl group, or a heterocyclic group, and have the same meaning as each group represented by Ra in the general formula (4). R ₉₅ represents a substituent, and the substituent is synonymous with the substituent represented by R ₁₁ in the general formula (1).

R ₉₆ , R ₉₇ , R ₉₈ and R ₉₉ represent an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, or an aromatic heterocyclic group, and these are represented by Ra in the general formula (4). It is synonymous with each group.

  According to the present invention, at least one gold orthometal complex selected from the partial structure group consisting of the general formulas (1) to (6), at least one gold of the above general formulas (A) to (C). The orthometalated complex, the monovalent gold orthometal complex represented by the general formula (D) or (E) is at least selected from the partial structure group consisting of the general formulas 1-1 to 1-150. It is preferable to have one partial structure or a tautomer of the partial structure as a partial structure.

<< At least one partial structure selected from the partial structure group consisting of general formulas 1-1 to 1-150 or tautomers of the partial structures >>
In General Formulas 1-1 to 1-150, the substituents represented by R ₁₃ and R ₁₄ are the same as the substituents represented by R ₁₁ in General Formula (1).

In X ₁₅ and X ₁₆ of the general formulas 1-1 to 1-150, the alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group, aromatic heterocyclic group and the like represented by R ₁₅ are each represented by And has the same meaning as each group represented by Ra in formula (4).

In X ₁₇ and X ₁₈ in the general formulas 1-1 to 1-150, the alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group, aromatic heterocyclic group and the like represented by R ₁₆ are each represented by And has the same meaning as each group represented by Ra in formula (4).

  At least one gold orthometal complex selected from the partial structure group consisting of the above general formulas (1) to (6), and monovalent gold represented by the above general formula (D) or (E) It is preferable that the ortho metal complex has a partial structure having at least one partial structure selected from the partial structure group consisting of the above general formulas 2-1 to 2-50, or a tautomer of the partial structure. One of them.

<< At least one partial structure selected from the partial structure group consisting of the general formulas 2-1 to 2-50 or tautomers of the partial structures >>
In General Formulas 2-1 to 2-50, the substituents represented by R ₂₂ and R _{23 have the same} meaning as the substituents represented by R ₁₁ in General Formula (1).

In X ₂₅ of the general formulas 2-1 to 2-50, the alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group, aromatic heterocyclic group and the like represented by R ₂₄ are each represented by the general formula. It is synonymous with Ra of (4).

In X ₂₆ of the general formulas 2-1 to 2-50, the alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group, aromatic heterocyclic group and the like represented by R ₂₅ are each represented by the general formula. It is synonymous with Ra of (4).

  At least one gold orthometal complex selected from the partial structure group consisting of the above general formulas (1) to (6), and monovalent gold represented by the above general formula (D) or (E) One of the preferred embodiments of the ortho metal complex of the present invention has as a partial structure at least one partial structure selected from the partial structure group consisting of the general formulas 3-1 to 3-9 or a tautomer of the partial structure. It can be given as one.

<< At least one partial structure selected from the partial structure group consisting of general formulas 3-1 to 3-9 or tautomers of the partial structures >>
In General Formulas 3-1 to 3-9, the substituents represented by R ₃₂ and R ₃₃ are the same as the substituents represented by R ₁₁ in General Formula (1).

In X ₃₁ of the general formulas 3-1 to 3-9, the alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group, aromatic heterocyclic group and the like represented by R ₂₄ are each represented by the general formula: It is synonymous with Ra of (4).

In X ₃₂ of the general formulas 3-1 to 3-9, the alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group, aromatic heterocyclic group and the like represented by R ₂₅ are each represented by the general formula. It is synonymous with Ra of (4).

  At least one gold orthometal complex selected from the partial structure group consisting of the above general formulas (1) to (6), and monovalent gold represented by the above general formula (D) or (E) One of the preferred embodiments of the ortho metal complex is that it has a partial structure represented by the above general formula (7) or (8) or a tautomer of the partial structure as a partial structure.

<< Partial structure represented by general formula (7) or (8) or tautomers of the partial structure >>
In the general formula (7) or (8), each of the electron donating substituents represented by R ₅₁ , R ₅₂ , R ₅₃ , and R ₅₄ represents a group having a σp value smaller than 0 by Hammett. Specific examples of the σp value of the substituent are described in, for example, Chemical Review, Vol. 91, pages 165 to 195 (1991).

In the general formula (7) or (8), examples of the substituent represented by R ₅₆ , R ₅₇ , R ₅₈ , and R ₅₉ include the substituent represented by R ₁₁ in the general formula (1). However, at least one of R ₅₆ and R ₅₈ is an electron-withdrawing substituent. Here, the electron-withdrawing substituent represents a group having a Hammett's σp value smaller than 0. Specific examples of the σp value of the substituent are described in, for example, Chemical Review, Vol. 91, pages 165 to 195 (1991).

In General Formula (7) or (8), the substituent represented by R ₅₅ has the same definition as the substituent represented by R ₁₁ in General Formula (1).

  In Xa of the general formula (7) or (8), an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group, an aromatic heterocyclic group and the like represented by Ra are each represented by the general formula (4). ) And Ra.

  At least one gold orthometal complex selected from the partial structure group consisting of the above general formulas (1) to (6), and monovalent gold represented by the above general formula (D) or (E) One of the preferred embodiments of the ortho metal complex is that it has a partial structure represented by the general formula (9) or a tautomer of the partial structure as a partial structure.

<< Partial structure represented by general formula (9) or tautomers of the partial structure >>
In general formula (9), Q ₁₈ forms together with the carbon atom and X ₅₆ , the 6-membered aromatic hydrocarbon ring, 5-membered to 6-membered aromatic heterocycle, etc. are each represented by Q in general formula (1). Synonymous with ₁₁ .

In the general formula (9), Q ₁₉ is, carbon atoms and X _57, to form together with the nitrogen atom, an aromatic heterocyclic 5- to 6-membered, 5-membered to defined by Q ₁₁ of the general formula (1) Synonymous with 6-membered aromatic heterocycle.

In the general formula (9), Q ₂₀ and Q ₂₁ are each independently formed with two carbon atoms, and the 6-membered aromatic hydrocarbon ring, aromatic heterocycle and the like are each represented by Q _{11 in the} general formula (1). It is synonymous with.

  At least one gold orthometal complex selected from the partial structure group consisting of the above general formulas (1) to (6), and monovalent gold represented by the above general formula (D) or (E) One of the preferred embodiments of the ortho metal complex is that it has a partial structure represented by the general formula (10) or a tautomer of the partial structure as a partial structure.

<< Partial structure represented by general formula (10) or tautomers of the partial structure >>
In the general formula (10), Q ₂₂ forms together with the carbon atom, X ₆₆ , X ₆₈ , a 6-membered aromatic hydrocarbon ring, a 5-membered to 6-membered aromatic heterocycle, etc., respectively. ) Q ₁₁ .

In the general formula (10), the 5-membered to 6-membered aromatic heterocycle formed by Q ₂₃ together with the carbon atom, X ₆₇ , X ₆₉ and nitrogen atom is 5 defined by Q ₁₁ in the general formula (1). It is synonymous with a 6-membered aromatic heterocycle.

In the general formula (10), the substituent having a van der Waals volume represented by X _f and X _g of 20 μm or more is a parameter determined by using molecular simulation software Cerius 2 manufactured by Accelrys Co., Ltd. A substituent is introduced, the molecular structure is optimized by MM calculation using the Driving Force Field, and the van der Waals (VDW) volume of the volume value obtained by using the Conon Surface is defined as a substituent having a volume of 20 or more. .

  For example, specific values are as shown in the following table, and appropriate values can be selected as appropriate. Incidentally, several examples of substituents of less than 20% are shown below.

Substituent Å ³
Methyl group 25.4
Ethyl group 42.6
Isopropyl group 59.5
tert-Butyl group 76.2
Phenyl group 74.9
Methoxy group 34.0
Amino group 22.2
Hydroxyl group 16.7
Chlorine atom 22.4
Bromine atom 26.5
Fluorine atom 13.3
Trifluoromethyl group 42.5
Also, at least one gold orthometal complex selected from the partial structure group consisting of the general formulas (1) to (6), or a monovalent group represented by the general formula (D) or (E). One preferred embodiment of the gold orthometal complex is that it has a partial structure represented by the general formulas (11) to (14) or a tautomer of the partial structure as a partial structure.

<< Partial structure represented by general formula (11)-(14) or tautomer of the partial structure >>
In the general formulas (11) to (14), Q ₂₄ is a 6-membered aromatic hydrocarbon ring formed together with a carbon atom, X ₇₁ , or X ₇₃ , a 5-membered to 6-membered aromatic heterocycle, etc. it is synonymous with Q ₁₁ of formula (1).

In the general formulas (11) to (14), the 5-membered to 6-membered aromatic heterocycle formed by Q ₂₅ together with the carbon atom, X ₇₂ , X ₇₄ and nitrogen atom is Q _{11 of the} general formula (1). It is synonymous with the 5-membered to 6-membered aromatic heterocyclic ring defined by

In the general formulas (11) to (14), the aromatic hydrocarbon ring formed by Q ₂₆ together with the carbon atom includes a benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, chrysene Ring, naphthacene ring, triphenylene ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen And a ring, a picene ring, a pyrene ring, a pyranthrene ring, and an anthraanthrene ring. Furthermore, the aromatic hydrocarbon ring may have a substituent represented by R ₁₁ in the general formula (1).

In the general formulas (11) to (14), the aromatic heterocycle formed by Q ₂₆ together with the carbon atom includes a furan ring, a thiophene ring, an oxazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring. , Benzimidazole ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, carbazole ring, carboline Ring, a diazacarbazole ring (which represents a ring in which one of the carbon atoms of the hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom), and the like. Furthermore, the aromatic heterocyclic ring may have a substituent represented by R ₁₁ in the general formula (1).

In the general formula (11) to (14), the aromatic heterocyclic ring Q ₂₇ forms together with the nitrogen atom, an oxazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a benzimidazole ring, oxa Diazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, carbazole ring, carboline ring, diazacarbazole ring (It represents 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 aromatic heterocyclic ring may have a substituent represented by R ₁₁ in the general formula (1).

  Hereinafter, although the specific example of the gold ortho metal complex which concerns on this invention is shown, this invention is not limited to these.

  Gold ortho metal complexes according to the present invention are described in, for example, Journal of Organicometric Chemistry, vol. 363, p419-424 (1989), Russian Journal of General Chemistry, vol. 71, no. 10, p 1660 to 1661 (2001), Journal of Organometallic Chemistry vol. 679, P194-201 (2003), etc., and by applying a method such as a reference document described in the above-mentioned document.

  The organic EL element material containing a gold orthometalated complex according to the present invention forms any of the constituent layers constituting the organic EL element (the constituent layers will be described in detail later), or It is contained in the constituent layer. Here, the organic EL element material of the present invention containing a gold orthometalated complex is preferably contained in the light emitting layer or the hole blocking layer among the constituent layers of the organic EL element.

<< Application of organic EL element material containing metal complex to organic EL element >>
When producing an organic EL element using a gold ortho metal complex, which is an organic EL element material of the present invention, a light emitting layer or a hole blocking layer in the constituent layers (details will be described later) of the organic EL element It is preferable to use for. Moreover, in a light emitting layer, it is preferably used as a light emitting dopant. In the light emitting layer, the gold orthometal complex according to the present invention can be preferably used as a phosphorescent compound described later.

  Here, the light emitting layer, which is a constituent layer of the organic EL element of the present invention, will be described first.

<Light emitting layer>
The light-emitting layer according to the present invention is a layer that contains at least a light-emitting host and a light-emitting dopant as a light-emitting material and emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer. The light emitting portion may be in the light emitting layer or at the interface between the light emitting layer and the adjacent layer.

(Ratio of luminescent host to luminescent dopant)
The mixing ratio with the light-emitting dopant for the light-emitting host in the light-emitting layer (by the way, the phosphorescent compound according to the present invention described later is a kind of light-emitting dopant) is preferably 0.1% by mass to 30% by mass. It is adjusting to the range of less than mass%.

(Luminescent dopant, phosphorescent compound)
In the present invention, a phosphorescent compound (also referred to as a phosphorescent compound) is preferably used as the light-emitting material, whereby high emission luminance and light emission efficiency can be obtained. A phosphorescent compound 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 0.01 or more at 25 ° C. It is. 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 quantum yield used in the present invention only needs to achieve the above phosphorescence quantum yield in any solvent.

  Moreover, as a phosphorescent compound, you may select from the well-known thing used for the light emitting layer of an organic EL element suitably, and you may use together with the gold ortho metalation complex which concerns on this invention.

Both the phosphorescence quantum yield of the phosphorescent compound and the phosphorescence quantum yield of the host compound should be measured by the method described on page 398 (1992 edition, Maruzen) of Spectroscopic II of the Fourth Edition Experimental Chemistry Course 7. However, the light-emitting dopant may be a mixture of a plurality of types of compounds, and the partner to be mixed may be a phosphorescent dopant or a fluorescent dopant having a different structure, other metal complexes or other structures. .

  Preferred embodiments of the phosphorescent compound (also simply referred to as phosphorescent dopant) according to the present invention include the following embodiments.

(A) When two or more different phosphorescent compounds are contained in the same light emitting layer (b) When two or more different phosphorescent compounds are contained in different light emitting layers (c) 3 When two types of different phosphorescent compounds are included in the same light emitting layer, and the remaining one is included in a light emitting layer different from the light emitting layer including the two types. The dopant (phosphorescent dopant, fluorescent dopant, etc.) that may be used in combination with the phosphorescent compound according to the present invention will be described.

  The light-emitting dopant is roughly classified into two types: a fluorescent dopant that emits fluorescence and a phosphorescent dopant that emits phosphorescence.

  Representative examples of the former (fluorescent dopant) 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.

  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 of the compounds that may be used in combination with the gold orthometal complex according to the present invention are shown below.

(Light emitting host)
There are two types of light emission of phosphorescent compounds in principle. One is the recombination of carriers on the host compound to which carriers are transported to generate an excited state of the host compound, and this energy is phosphorescent. Energy transfer type to obtain light emission from the phosphorescent compound by transferring to the compound, the other is the phosphorescent compound becomes a carrier trap, carrier recombination occurs on the phosphorescent compound, from the phosphorescent compound In any case, the excited state energy of the phosphorescent compound is preferably lower than the excited state energy of the host compound.

  The light-emitting host used in 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, a thiophene derivative, a furan derivative, an oligo Those having a basic skeleton such as an arylene compound, or a carboline derivative or diazacarbazole derivative (herein, a diazacarbazole derivative is a nitrogen atom in which at least one carbon atom of the hydrocarbon ring constituting the carboline ring of the carboline derivative is a nitrogen atom) And the like.) And the like.

  Of these, carboline derivatives, diazacarbazole derivatives, compounds represented by the above general formula (33), and the like are preferably used.

  Here, the host compound used in the present invention is 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.

<< Compound Represented by Formula (33) >>
The compound represented by the general formula (33) according to the present invention will be described.

  As a result of intensive studies, the inventors of the present invention have prepared the compound represented by the general formula (33) in a light emitting layer or a layer adjacent to the light emitting layer, and using a phosphorescent compound described later for the light emitting layer. It has been found that the organic EL device has high luminous efficiency and can have a long lifetime.

In the general formula (33), Z ₁ represents an aromatic heterocyclic ring which may have a substituent, and Z ₂ represents an aromatic heterocyclic ring which may have a substituent or an aromatic hydrocarbon ring. , Z ₃ represents a divalent linking group or a simple bond. R ₁₀₁ represents a hydrogen atom or a substituent.

In the general formula (33), the aromatic heterocycles represented by Z ₁ and Z ₂ are furan ring, thiophene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzimidazole ring, oxa Diazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, carbazole ring, carboline ring, carboline ring And a ring in which the carbon atom of the hydrocarbon ring is further substituted with a nitrogen atom. Furthermore, the aromatic heterocyclic ring may have a substituent represented by R ₁₀₁ described later.

In the general formula (33), examples of the aromatic hydrocarbon ring represented by Z ₂ include benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, chrysene ring, naphthacene ring, triphenylene. Ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, picene ring, pyrene Ring, pyranthrene ring, anthraanthrene ring and the like. Furthermore, the aromatic hydrocarbon ring may have a substituent represented by R ₁₀₁ described later.

In the general formula (33), the substituent represented by R ₁₀₁ includes 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 For example, 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.), cyclo An alkoxyl group (eg, cyclopentyloxy group, cyclohexyloxy group, etc.), an aryloxy group (eg, phenoxy group, naphthyloxy group, etc.), an 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.), alkoxycarbonyl group (eg, Tiloxycarbonyl 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 groups (for example, acetyl group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group, Rohexylcarbonyl 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, cyclohexyl) Carbonylamino group, 2-ethylhexylcarbonylamino group, octylcarbonylamino group, dodecylcarbonylamino group, phenylcarbonylamino group, naphthyl Tilcarbonylamino group, etc.), carbamoyl groups (for example, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexylaminocarbonyl group, octylaminocarbonyl group, 2-ethylhexylamino) Carbonyl 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, ethyl) Sulfinyl 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-pyri Ruamino group, etc.), halogen atoms (eg fluorine atom, chlorine atom, bromine atom etc.), fluorinated hydrocarbon groups (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.

  Preferred substituents are an alkyl group, a cycloalkyl group, a fluorinated hydrocarbon group, an aryl group, and an aromatic heterocyclic group.

  As the divalent linking group, in addition to hydrocarbon groups such as alkylene, alkenylene, alkynylene, and arylene, those containing a hetero atom may be used, and a thiophene-2,5-diyl group, pyrazine-2, It may be a divalent linking group derived from a compound having an aromatic heterocyclic ring (also called a heteroaromatic compound) such as a 3-diyl group, or may be a chalcogen atom such as oxygen or sulfur. . Further, it may be a group such as an alkylimino group, a dialkylsilanediyl group, or a diarylgermandiyl group that connects and connects heteroatoms.

  A mere bond is a bond that directly bonds the connecting substituents together.

In the present invention, Z _{1 in the} general formula (33) is preferably a 6-membered ring. Thereby, luminous efficiency can be made higher. Furthermore, the lifetime can be further increased.

In the present invention, Z _{2 in the} general formula (33) is preferably a 6-membered ring. Thereby, luminous efficiency can be made higher. Furthermore, the lifetime can be further increased.

Furthermore, it is preferable that Z ₁ and Z _{2 in} the general formula (33) are both 6-membered rings because the luminous efficiency can be further increased. Furthermore, it is preferable because the lifetime can be further increased.

  Preferred among the compounds represented by the general formula (33) are compounds represented by the general formulas (33-1) to (33-13).

In the general formula (33-1), R _{501 to} R ₅₀₇ each independently represent a hydrogen atom or a substituent.

  By using the compound represented by the general formula (33-1), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (33-2), R _{511 to} R ₅₁₇ each independently represent a hydrogen atom or a substituent.

  By using the compound represented by the general formula (33-2), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (33-3), R _{521 to} R ₅₂₇ each independently represent a hydrogen atom or a substituent.

  By using the compound represented by the general formula (33-3), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (33-4), R _{531 to} R ₅₃₇ each independently represent a hydrogen atom or a substituent.

  By using the compound represented by the general formula (33-4), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In formula (33-5), R ₅₄₁ ~R ₅₄₈ each independently represents a hydrogen atom or a substituent.

  By using the compound represented by the general formula (33-5), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (33-6), R _{551 to} R ₅₅₈ each independently represent a hydrogen atom or a substituent.

  By using the compound represented by the general formula (33-6), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (33-7), R _{561 to} R ₅₆₇ each independently represents a hydrogen atom or a substituent.

  By using the compound represented by the general formula (33-7), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (33-8), R _{571 to} R ₅₇₇ each independently represent a hydrogen atom or a substituent.

  By using the compound represented by the general formula (33-8), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (33-9), R _{581 to} R ₅₈₈ each represent a hydrogen atom or a substituent.

  By using the compound represented by the general formula (33-9), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (33-10), R _{591 to} R ₅₉₈ each represent a hydrogen atom or a substituent.

  By using the compound represented by the general formula (33-10), an organic EL device with higher luminous efficiency can be obtained. Furthermore, a long-life organic EL element can be obtained.

In addition, a preferable compound represented by the general formula (33) is a compound having at least one group represented by any one of the general formulas (34-1) to (34-8). In particular, it is more preferable to have 2 to 4 groups represented by any one of the general formulas (34-1) to (34-8) in the molecule. In this case, the structure represented by the general formula (33) includes a case where the portion excluding R ₁₀₁ is replaced by the general formulas (34-1) to (34-8).

  At this time, the compounds represented by the general formulas (35) to (49) are particularly preferable for obtaining the effects of the present invention.

In the general formula (35), R _{601 to} R ₆₀₆ represent a hydrogen atom or a substituent, and at least one of R _{601 to} R ₆₀₆ is represented by the general formulas (34-1) to (34-4). The group represented by either is represented.

  By using the compound represented by the general formula (35), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (4), R _{611 to} R ₆₂₀ represent a hydrogen atom or a substituent, and at least one of R _{611 to} R ₆₂₀ is represented by the general formulas (34-1) to (34-4). The group represented by either is represented.

  By using the compound represented by the general formula (36), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (37), R _{621 to} R ₆₂₃ represent a hydrogen atom or a substituent, and at least one of R _{611 to} R ₆₂₀ is represented by the general formulas (34-1) to (34-4). The group represented by either is represented.

  By using the compound represented by the general formula (37), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (38), R _{631 to} R ₆₄₅ represent a hydrogen atom or a substituent, and at least one of R _{631 to} R ₆₄₅ is represented by the general formulas (34-1) to (34-4). The group represented by either is represented.

  By using the compound represented by the said General formula (38), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as a longer life organic EL element.

In the general formula (39), R _{651 to} R ₆₅₆ represent a hydrogen atom or a substituent, and at least one of R _{651 to} R ₆₅₆ is represented by the general formulas (34-1) to (34-4). The group represented by either is represented. na represents an integer of 0 to 5, and nb represents an integer of 1 to 6, but the sum of na and nb is 6.

  By using the compound represented by the general formula (39), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the general formula (40), R _{661 to} R _{672 each} represents a hydrogen atom or a substituent, and at least one of R _{661 to} R ₆₇₂ is represented by the general formulas (34-1) to (34-4). The group represented by either is represented.

  By using the compound represented by the said General formula (40), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as a longer life organic EL element.

In the general formula (41), R _{681 to} R ₆₈₈ represent a hydrogen atom or a substituent, and at least one of R _{681 to} R ₆₈₈ is represented by the general formulas (34-1) to (34-4). The group represented by either is represented.

  By using the compound represented by the said General formula (41), it can be set as an organic electroluminescent element with higher luminous efficiency. Furthermore, it can be set as a longer life organic EL element.

In the general formula (42), R _{691 to} R ₇₀₀ represent a hydrogen atom or a substituent, and at least one of R _{691 to} R ₇₀₀ is represented by the general formulas (34-1) to (34-4). The group represented by either is represented.

In the general formula (42), the divalent linking group represented by L ₁ is an alkylene group (for example, ethylene group, trimethylene group, tetramethylene group, propylene group, ethylethylene group, pentamethylene group, hexamethylene group). Group, 2,2,4-trimethylhexamethylene group, heptamethylene group, octamethylene group, nonamethylene group, decamethylene group, undecamethylene group, dodecamethylene group, cyclohexylene group (for example, 1,6-cyclohexanediyl group, etc.) ), Cyclopentylene group (eg, 1,5-cyclopentanediyl group, etc.), alkenylene group (eg, vinylene group, propenylene group, etc.), alkynylene group (eg, ethynylene group, 3-pentynylene group, etc.), In addition to hydrocarbon groups such as arylene groups, groups containing heteroatoms (eg, —O , —S— and the like, a divalent group containing a chalcogen atom, —N (R) — group, wherein R represents a hydrogen atom or an alkyl group, and the alkyl group in the general formula (33), And the same as the alkyl group represented by R ₁₀₁ .

  In each of the alkylene group, alkenylene group, alkynylene group, and arylene group, at least one of carbon atoms constituting the divalent linking group is a chalcogen atom (oxygen, sulfur, etc.) or -N (R). -It may be substituted with a group or the like.

Furthermore, as the divalent linking group represented by L ₁ , for example, a group having a divalent heterocyclic group is used. For example, an oxazolediyl group, a pyrimidinediyl group, a pyridazinediyl group, a pyrandiyl group, a pyrrolindiyl group. Group, imidazoline diyl group, imidazolidine diyl group, pyrazolidine diyl group, pyrazoline diyl group, piperidine diyl group, piperazine diyl group, morpholine diyl group, quinuclidine diyl group and the like, and thiophene-2,5- A divalent linking group derived from a compound having an aromatic heterocyclic ring (also referred to as a heteroaromatic compound) such as a diyl group or a pyrazine-2,3-diyl group may be used.

  Further, it may be a group that meets and links heteroatoms such as an alkylimino group, a dialkylsilanediyl group, or a diarylgermandiyl group.

  By using the compound represented by the general formula (42), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it can be set as a longer life organic EL element.

In the compounds represented by the general formula (43) to the general formula (47), the substituents represented by R ₁ and R ₂ are the substituents represented by R ₁₀₁ in the general formula (33). At the same time as the group.

In the general formula (47), examples of the 6-membered aromatic heterocyclic ring each containing at least one nitrogen atom represented by Z ₁ , Z ₂ , Z ₃ and Z ₄ include a pyridine ring and a pyridazine ring. , Pyrimidine ring, pyrazine ring and the like.

In the general formula (48), examples of the 6-membered aromatic heterocycle each containing at least one nitrogen atom represented by Z ₁ and Z ₂ include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring. Etc.

In the general formula (48), the arylene groups represented by Ar ₁ and Ar ₂ are o-phenylene group, m-phenylene group, p-phenylene group, naphthalenediyl group, anthracenediyl group, naphthacenediyl group, and pyrenediyl group. Group, naphthylnaphthalenediyl group, biphenyldiyl group (for example, 3,3′-biphenyldiyl group, 3,6-biphenyldiyl group, etc.), terphenyldiyl group, quaterphenyldiyl group, kinkphenyldiyl group, sexi Examples thereof include a phenyldiyl group, a septiphenyldiyl group, an octylphenyldiyl group, a nobiphenyldiyl group, and a deciphenyldiyl group. The arylene group may further have a substituent described later.

In the general formula (48), the divalent aromatic heterocyclic groups represented by Ar ₁ and Ar ₂ are furan ring, thiophene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzo Imidazole ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, carbazole ring, carboline ring, And divalent groups derived from a ring in which the carbon atom of the hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom. Furthermore, the aromatic heterocyclic group may have a substituent represented by R ₁₀₁ .

In the general formula (48), the divalent linking group represented by L is the same as the divalent linking group represented by L ₁ in the general formula (42), but preferably an alkylene group. , —O—, —S— and the like, are divalent groups containing a chalcogen atom, most preferably an alkylene group.

In the general formula (49), in Ar _1, Ar _2, the arylene group represented by each, in the general formula (48), it is synonymous with the arylene group represented by each of Ar _1, Ar _2.

In the general formula (49), an aromatic heterocyclic group represented by each of Ar _1, Ar _2, in the general formula (48), the divalent aromatic heterocyclic ring represented by each of Ar _1, Ar ₂ Synonymous with group.

In the general formula (49), examples of the 6-membered aromatic heterocyclic ring each containing at least one nitrogen atom represented by Z ₁ , Z ₂ , Z ₃ and Z ₄ include a pyridine ring and a pyridazine ring. , Pyrimidine ring, pyrazine ring and the like.

In the general formula (49), the divalent linking group represented by L has the same meaning as the divalent linking group represented by L ₁ in the general formula (42), but is preferably an alkylene group. , —O—, —S— and the like, are divalent groups containing a chalcogen atom, most preferably an alkylene group.

  Although the specific example of a compound represented by General formula (33) based on this invention below is shown, this invention is not limited to these.

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

  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, it is preferable to use the organic EL element material of the present invention for the hole blocking layer, the electron blocking layer, etc., and particularly preferably for the hole blocking layer.

  When the organic EL element material of the present invention is contained in a hole blocking layer or an electron blocking layer, the metal complex according to any one of claims 1 to 17 is converted into a hole blocking layer or an electron. It may be contained in a state of 100% by mass as a layer constituent component such as a blocking layer, or may be mixed with other organic compounds (for example, a compound used for a constituent layer of the organic EL device of the present invention). .

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

  Examples of the hole blocking layer include those disclosed in JP-A-11-204258, JP-A-11-204359, and “Organic EL device and its forefront of industrialization (issued by NTS, Inc. on November 30, 1998)”. The hole blocking (hole block) layer described in page 237 and the like can be applied as the hole blocking layer according to the present invention. Moreover, the structure of the electron carrying layer mentioned later can be used as a hole-blocking layer concerning this invention as needed.

《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.

  In the present invention, it is preferable to use the compound represented by the general formula (33) for the adjacent layer adjacent to the light emitting layer, that is, the hole blocking layer and the electron blocking layer, and particularly for the hole blocking layer. It is preferable to use it.

《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 an optical transmission material or a well-known material used for a hole injection layer or a hole transport layer of an EL element. 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, 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-4-308 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 88 are linked in a starburst type (MTDATA).

  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 material preferably has a high Tg.

  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, 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 nm-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 multiple 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 from conventionally known compounds. .

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

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

  In addition, metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum. , Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and the like, and the central metal of these metal complexes is 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 the terminal 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 similarly to the hole injection layer and the hole transport layer, inorganic such as n-type-Si and n-type-SiC. 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, 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. The 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 The injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, and as described above, between the anode and the light emitting layer or the hole transport layer, and You may exist between a cathode, a light emitting layer, or an electron carrying layer.

  An injection layer is a layer provided between an electrode and an organic layer in order to lower drive voltage or improve light emission luminance. “Organic EL element and its forefront of industrialization (issued on November 30, 1998 by NTS Corporation) 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 or aluminum Metal buffer layer represented by lithium fluoride, alkali metal compound buffer layer represented by lithium fluoride, alkaline earth metal compound buffer layer represented by magnesium fluoride, oxide buffer layer represented by aluminum oxide, etc. It is done.

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

  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 nm-5000 nm. This 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 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 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, 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 1000 nm, preferably 50 nm 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 to the type of glass, plastic, etc., and is not particularly limited as long as it is transparent. Examples of substrates that are preferably used include glass, quartz, A light transmissive resin film can be mentioned. 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 triacetate. Examples thereof include films made of (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 the film should be a high barrier film having a water vapor transmission rate of 0.01 g / m ² · day · atm or less. preferable.

  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 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 organic EL elements having at least two 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 nm 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 described above, there are spin coating method, casting method, ink jet method, vapor deposition method, printing method and the like as a method for thinning the thin film containing the organic compound, but it is easy to obtain a uniform film and has pinholes. From the viewpoint of difficulty in formation, vacuum deposition or spin coating is 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 a range of 0.01 nm to 50 nm / second, a substrate temperature of −50 to 300 ° C., and a film thickness of 0.1 nm to 5 μm.

  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.

<Display device>
The display device of the present invention will be described.

  The display device of the present invention may be single color or multicolor, but here, the multicolor display device will be described. 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 a vapor deposition method, a casting method, a spin coating method, an ink jet method, a printing method, 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 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 by reversing the production 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 V to 40 V with the anode as + and the cathode as-polarity. 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, or 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.

  Light 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. For example, but not limited to.

《Lighting device》
The lighting device of the present invention will be described.

  The organic EL element of the present invention may be used as an organic EL element having a resonator structure. The use of the organic EL element having such a resonator structure is as a light source for an optical storage medium, an electrophotographic copying machine, and the like. Light sources, optical communication processor light sources, optical sensor light sources, and the like. 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 type for directly viewing a still image or a moving image. It may be used as a display 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 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 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.

  In the figure, 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 lattice shape and are connected to the pixels 3 at the 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 a color mixture. The combination of a plurality of emission colors may include three emission maximum wavelengths of three primary colors of blue, green, and blue, or two using a complementary color relationship such as blue and yellow, blue green and orange, etc. 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 organic EL element of the present invention is a liquid crystal display as a kind of lamp such as home lighting, 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 device backlights.

  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.

  Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited thereto.

  Here, the list of the compounds used in the examples (including those listed in the table, those not listed in the table, and simply listed in the evaluation) is shown.

Example 1
<< Production of Organic EL Element OLED1-1 >>
After patterning on a substrate (made by NH Techno Glass Co., Ltd .: 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. The sample was dried 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 evaporation apparatus, while α-NPD, CBP, Ir-12 (FIrpic), BCP, and Alq ₃ are placed in five tantalum resistance heating boats, It attached to the vacuum evaporation system (1st vacuum chamber).

  Furthermore, lithium fluoride was put into a resistance heating boat made of tantalum, and aluminum was put into a resistance heating boat made of tungsten, respectively, and attached to the second vacuum tank of the vacuum deposition 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 / second. The film was deposited to a thickness of 25 nm to provide a hole injection / transport layer.

  Further, the heating boat containing CBP and the boat containing Ir-12 are energized independently to adjust the deposition rate of CBP as a light emitting host and Ir-12 as a light emitting dopant to 100: 7. A light emitting layer was provided by vapor deposition so as to have a thickness of 30 nm.

Then, the heating boat containing BCP was energized and heated to provide a 10 nm thick hole blocking layer at a deposition rate of 0.1 nm / sec to 0.2 nm / sec. Further, the heating boat containing Alq ₃ was heated by energization to provide an electron transport layer having a film thickness of 40 nm at a deposition rate of 0.1 nm / second to 0.2 nm / second.

  Next, after the element formed up to the electron transport layer as described above is transferred to the second vacuum chamber in a vacuum state, a stainless steel rectangular perforated mask is disposed on the electron transport layer from the outside of the apparatus. Installed with remote control.

After reducing the pressure in the second vacuum chamber to 2 × 10 ⁻⁴ Pa, a cathode buffer layer having a film thickness of 0.5 nm was formed at a deposition rate of 0.01 nm / second to 0.02 nm / second by energizing a boat containing lithium fluoride. Then, a boat containing aluminum was energized to attach a cathode having a film thickness of 150 nm at a deposition rate of 1 nm / second to 2 nm / second, to fabricate an organic EL element OLED1-1.

<< Production of Organic EL Elements OLED1-2 to 1-20 >>
In preparation of said organic EL element OLED1-1, as described in Table 1, except having changed the light emission dopant, it carried out similarly and produced organic EL element OLED1-2-1-20.

  The following evaluation was performed about obtained organic EL element OLED1-1 to 1-20.

  In addition, the light emission dopant used for OLED1-5 to 1-20 of Table 1 is a compound selected from the specific example of said gold ortho metalation complex, The compound used for the light emission host is the general which concerns on this invention. It is a compound selected from the specific examples of the compound represented by Formula (33).

<< External quantum efficiency >>
The organic EL elements OLED1-1 to 1-20 are lit at room temperature (about 23 to 25 ° C.) under a constant current condition of ^2.5 mA / cm ² , and light 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 Minolta) was used for measurement of light emission luminance.

  The external extraction quantum efficiency was expressed as a relative value when the organic EL element OLED1-1 was set to 100.

<Luminescent life>
The organic EL elements OLED1-1 to 1-20 are continuously lit at a constant current of ^2.5 mA / cm ² at room temperature, and the time (τ _1/2 ) required to reach half the initial luminance is obtained. It was measured. Moreover, the light emission lifetime was represented by the relative value which set the organic EL element OLED1-1 to 100.

  The obtained results are shown in Table 1.

  From Table 1, it is clear that the organic EL device produced using the metal complex according to the present invention can achieve higher luminous efficiency and longer emission lifetime than the comparative organic EL device.

  Furthermore, by using a carboline derivative or a derivative having a ring structure in which at least one carbon atom of the hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom in the light emitting layer, the carboline derivative Alternatively, a derivative 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 further substituted with a nitrogen atom is used for the hole blocking layer. The improvement of the effect was seen.

Example 2
<Production of full-color display device>
(Production of blue light emitting element)
The organic EL element OLED1-11 of Example 1 was used as a blue light emitting element.

(Production of green light emitting element)
Ir-1 was used as a green light emitting element.

(Production of red light emitting element)
Ir-9 was used as a red light emitting element.

  Each of the red, green, and blue light emitting organic EL elements produced above was juxtaposed on the same substrate to produce an active matrix type full color display device having the form as shown in FIG. 1, and FIG. Only the schematic diagram of the display section A of the display device is shown. That is, a wiring portion including a plurality of scanning lines 5 and data lines 6 on the same substrate, and a plurality of juxtaposed pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) 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 ( Details are 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 manner, a full color display device was produced by appropriately juxtaposing the red, green, and blue pixels.

  It has been found that by driving the full-color display device, a clear full-color moving image display having high luminance, high durability, and clearness can be obtained.

Example 3
<Production of full-color display device>
A full color display device was produced in the same manner as in Example 7 except that the organic EL element OLED1-11 was changed to the organic EL element OLED1-12 in the production of the blue light emitting element of Example 2.

  It has been found that by driving the full-color display device, a clear full-color moving image display having high luminance, high durability, and clearness can be obtained.

Example 4
<Production of full-color display device>
A full-color display device was produced in the same manner as in Example 7 except that the organic EL element OLED1-11 was changed to the organic EL element OLED1-15 in the production of the blue light emitting element of Example 2.

  It has been found that by driving the full-color display device, a clear full-color moving image display having high luminance, high durability, and clearness can be obtained.

Example 5
<Production of full-color display device>
A full-color display device was produced in the same manner as in Example 7 except that the organic EL element OLED1-11 was changed to the organic EL element OLED1-16 in producing the blue light-emitting element of Example 2. It was found that by driving the full-color display device, a clear full-color moving image display having high luminance, high durability, and clearness can be obtained.

Example 6
<Production of element and white illumination 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, CBP The heating boat containing, the boat containing the example compound 34 which is an ortho metalated complex of gold, and the boat containing Ir-9 are energized independently, respectively, and CBP which is a light emitting host and a gold dopant which is a light emitting dopant. The vapor deposition rate was adjusted so that the example compound 34 which is an ortho metalation complex, and Ir-9 might be set to the deposition rate of 100: 5: 0.6, and it was set to the thickness of 30 nm, and the light emitting layer was provided.

Next, a hole blocking layer was provided by depositing BCP to a thickness of 10 nm. Furthermore, 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, lithium fluoride 0.5 nm as the cathode buffer layer and aluminum 150 nm as the cathode. Was deposited.

  The non-light-emitting surface of this organic EL element was covered with a glass case to obtain an illumination device as shown in FIGS. The illuminating device could be used as a thin illuminating device that emits white light with high luminous efficiency and long emission life. FIG. 5 shows a schematic diagram of the lighting device, and the organic EL element 101 is covered with a glass cover 102 (note that 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. Lower glove box (performed in an atmosphere of high purity nitrogen gas having 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.

  When the obtained illuminating device was energized, almost white light was obtained, and it was found that the illuminating device could be used.

Example 7
<Production of element and white illumination device>
A white lighting device was produced in the same manner as in Example 6 except that in the production of the element of Example 6, the exemplified compound 34 that was a gold orthometalated complex was changed to the exemplified compound 36 that was a gold orthometalated complex. .

  When the obtained illuminating device was energized, almost white light was obtained, and it was found that the illuminating device could be used.

Example 8
<Production of element and white illumination device>
A white lighting device was produced in the same manner as in Example 6 except that in the production of the element of Example 6, Exemplified Compound 34, which is a gold orthometalated complex, was changed to Illustrated Compound 41, which was a gold orthometalated complex. .

  When the obtained illuminating device was energized, almost white light was obtained, and it was found that the illuminating device could be used.

Example 9
<< Production of Organic EL Elements OLED2-1 to 2-13 >>
In the same manner as in Example 1, except that the luminescent dopant was changed to Ir-1 and the hole blocking material was changed as shown in Table 2, in the same manner as in Example 1, the organic EL elements OLED2-1 to 2-1 were used. 2-13 was produced.

  In addition, the compound used for the hole-blocking material used for OLED2-2 to 2-13 of Table 2 is at least 1 selected from the partial structure group which consists of following General formula (1)-(6) based on this invention. It is a compound selected from the specific examples of the gold ortho metal complex.

  The external extraction quantum efficiency and the light emission lifetime of each of the obtained devices were also measured in the same manner as described in Example 1.

  At this time, the value of OLED2-1 was set to 100, and the value of each organic EL element sample was represented by the relative value. The obtained results are shown in Table 2.

  From Table 2, it was found that the organic EL element using the organic EL element material of the present invention as the hole blocking material can obtain higher light emission efficiency and light emission lifetime than the comparative element. The emission color of the element of the present invention was all green.

It is the schematic diagram which showed an example of the display apparatus comprised from an organic EL element. It is a schematic diagram of a display part. 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 sectional drawing 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 107 Glass substrate with a transparent electrode 106 Organic EL layer 105 Cathode 102 Glass cover 108 Nitrogen gas 109 Water catcher

Claims (51)

An organic electroluminescent element material comprising at least one gold orthometal complex selected from a partial structure group consisting of the following general formulas (1) to (6).

[Wherein, X ₁₀ represents a carbon atom or a nitrogen atom, and Q ₁₁ together with the carbon atom and X ₁₀ forms a 6-membered aromatic hydrocarbon ring or a 5-membered to 6-membered aromatic heterocycle. Represents an atomic group. X ₁₁ , X ₁₂ , X ₁₃ and X ₁₄ each represent C—R ₁₁ , N, N—R ₁₁ , O or S, and together with the nitrogen atom form a 5-membered aromatic heterocycle. R ₁₁ represents a hydrogen atom or a substituent. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]

[Wherein, X ₂₀ represents a carbon atom or a nitrogen atom, and Q ₁₂ represents an atom that forms a 6-membered aromatic hydrocarbon ring or a 5-membered to 6-membered aromatic heterocyclic ring together with the carbon atom and X _20. Represents a group. X ₂₁ , X ₂₂ , X ₂₃ and X ₂₄ each represent C—R ₂₁ or N, and together with the nitrogen atom form a 6-membered aromatic heterocycle. R ₂₁ represents a hydrogen atom or a substituent. However, at least one of X _{21 to} X ₂₄ represents N. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]

[Wherein, X ₃₀ represents a carbon atom or a nitrogen atom, and Q ₁₃ represents an atom that forms a 6-membered aromatic hydrocarbon ring or a 5-membered to 6-membered aromatic heterocyclic ring together with the carbon atom and X _30. Represents a group. R ₃₁ represents a substituent. n3 represents an integer of 0 to 3. However, when n3> 1, the plurality of R ₃₁ may be the same as or different from each other. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]

[Wherein, R ₄₁ and R ₄₂ each represent a substituent, and m4 and n4 each represent an integer of 0 to 3. Xa represents -N (Ra) ₂ , -O-Ra or -S-Ra. Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. When Xa is —N (Ra) ₂ , the two Ras may be the same or different. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]

[Wherein, X ₅₁ , X ₅₂ , X ₅₃ and X ₅₄ each represent a carbon atom or a nitrogen atom, and Q ₁₄ represents a carbon atom, a 6-membered aromatic hydrocarbon ring together with X ₅₁ and X ₅₃ , or 5 The atomic group which forms a 6-membered aromatic heterocyclic ring is represented. Q ₁₅ forms a 5-membered to 6-membered aromatic heterocyclic ring together with the carbon atom, X ₅₂ , X ₅₄ and nitrogen atom. X _b and X _c each represents a substituent. m5 and n5 each represents 0 or 1. However, m5 + n5 ≧ 1. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ]

[Wherein, X ₆₁ , X ₆₂ , X ₆₃ , X ₆₄ each represents a carbon atom or a nitrogen atom, Q ₁₆ represents a carbon atom, a six-membered aromatic hydrocarbon ring together with X ₆₁ , X ₆₂ , or 5 The atomic group which forms a 6-membered aromatic heterocyclic ring is represented. Q ₁₇ forms a 5-membered or 6-membered aromatic heterocycle together with the carbon atom, X ₆₃ , X ₆₄ and nitrogen atom. X _c and X _d each represents a substituent. m6 and n6 each represents 0 or 1. However, m6 + n6 ≧ 1. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ] An organic electroluminescent device material comprising at least one trivalent gold orthometal complex selected from the group consisting of the following general formulas (A), (B) and (C).

Wherein, A _1, A ₂ each represent a carbon atom or a nitrogen atom, Q ₁ is an aromatic heterocyclic ring aromatic hydrocarbon ring 6 membered together with a carbon atom and A ₁ or 5-6 membered, Represents an atomic group forming Q ₂ represents an atomic group that forms a 5-membered to 6-membered aromatic heterocyclic ring together with the nitrogen atom and A ₂ . Q ₁ and Q ₂ constitute a ligand which is bonded to each other via A ₁ and A ₂ to form a trivalent gold orthometal complex, and X ₁ and X ₂ may be the same or different. Represents a monovalent anionic monodentate ligand. X ₃ and X ₄ each represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and together with L ₁ form a minus monovalent anionic bidentate ligand. X ₅ and X ₆ each represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and together with L ₂ form a negative divalent anionic bidentate ligand. Z ⁻ represents a monovalent anion. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ] An organic electroluminescence element material comprising a monovalent gold orthometal complex represented by the following general formula (D) or (E):

Wherein, A _1, A ₂ each represent a carbon atom or a nitrogen atom, Q ₁ is an aromatic heterocyclic ring aromatic hydrocarbon ring 6 membered together with a carbon atom and A ₁ or 5-6 membered, Represents an atomic group forming Q ₂ forms a 5- or 6-membered aromatic heterocycle with the nitrogen atom and A ₂ . Q ₁ and Q ₂ constitute a ligand that is bonded to each other via A ₁ and A ₂ to form a monovalent gold ortho metal complex. X ₇ represents an uncharged monodentate ligand, X ₈ represents a minus monovalent anionic monodentate ligand, and Y ⁺ represents a monovalent cation. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ] It contains at least one partial structure selected from a partial structure group consisting of the following general formulas 1-1 to 1-150 or a tautomer of the partial structure as a partial structure, and contains a gold orthometal complex. The organic electroluminescent element material according to any one of claims 1 to 3.

[Wherein, R ₁₃ and R ₁₄ each represent a substituent, and n11 and n12 each represent an integer of 0 to 2. X ₁₅ and X ₁₆ each represent> N—R ₁₅ , —O— or —S—. R ₁₅ represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X ₁₇ and X ₁₈ each represent> N—R ₁₆ , —O— or —S—. R ₁₆ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X _19a , X _19b and X _19c each represent CH or N, and any one or two of them are N. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ] Containing at least one kind of orthometal complex having at least one partial structure selected from the partial structure group consisting of the following general formulas 2-1 to 2-50 or a tautomer of the partial structure as a partial structure The organic electroluminescent element material according to any one of claims 1 to 3.

[Wherein, R ₂₂ and R ₂₃ each represent a substituent, and n21 and n22 each represents an integer selected from 0 to 2. X ₂₅ represents> N—R ₂₄ , —O— or —S—. R ₂₄ represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X ₂₆ represents> N—R ₂₅ , —O— or —S—. R ₂₅ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X ₂₇ , X ₂₈ , and X ₂₉ each represent CH or N, and any one or two are N. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). _{2 -, - C (= O} ) -, - C (= NR) -, - S (O) -, or, -SO ₂ - represents a. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ] Containing at least one partial structure selected from the partial structure group consisting of the following general formulas 3-1 to 3-10, or an orthometal complex characterized by having a tautomer of the partial structure as a partial structure The organic electroluminescent element material according to any one of claims 1 to 3.

[Wherein, R ₃₂ and R ₃₃ each represent a substituent, and n31 and n32 each represents an integer selected from 0 to 2. X ₃₁ represents> N—R ₂₄ , —O— or —S—. R ₂₄ represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X ₃₂ represents> N—R ₂₅ , —O— or —S—. R ₂₅ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X ₃₃ , X ₃₄ , and X ₃₅ each represent CH or N, and any one or two are N. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). _{2 -, - C (= O} ) -, - C (= NR) -, - S (O) -, or, -SO ₂ - represents a. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ] An ortho-metal complex having a partial structure represented by the following general formula (7) or (8) or a tautomer of the partial structure as a partial structure: Organic electroluminescent element material of any one of these.

[Wherein, R ₅₁ , R ₅₂ , R ₅₃ and R ₅₄ each represent a hydrogen atom or an electron-donating substituent, and at least one of them is an electron-donating substituent. R ₅₆ , R ₅₇ , R ₅₈ and R ₅₉ each represent a hydrogen atom or a substituent, and at least one of R ₅₆ and R ₅₈ is an electron-withdrawing substituent. R ₅₅ represents a substituent, n5 is an integer selected from 0-3. Xa represents -N (Ra) ₂ , -O-Ra or -S-Ra. Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. When Xa is —N (Ra) ₂ , the two Ras may be the same or different. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ] The organic material according to any one of claims 1 to 3, comprising an orthometal complex having a partial structure represented by the following general formula (9) or a tautomer of the partial structure as a partial structure. Electroluminescence element material.

[Wherein, X ₅₆ , X ₅₇ , X ₅₈ and X ₅₉ each represent a carbon atom or a nitrogen atom, and Q ₁₈ represents a carbon atom, X ₅₆ and X ₅₇ together with a 6-membered aromatic hydrocarbon ring, or 5 Q ₁₉ represents an atomic group that forms a 5-membered to 6-membered aromatic heterocyclic ring together with a carbon atom, X ₅₈ , X ₅₉ , and a nitrogen atom. To express. X _f and X _g represent a substituent having a van der Waals volume of 20 mm or more. m1 and n1 represent 0 or 1. However, m1 + n1 ≧ 1. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). ) ₂ —, —C (═O) —, —C (═NR) —, —S (O) —, or —SO ₂ —. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ] The ortho metal complex which has the partial structure represented by following General formula (10) or the tautomer of this partial structure as a partial structure is contained, The any one of Claims 1-3 characterized by the above-mentioned. Organic electroluminescence element material.

[In the formula, X ₆₆ , X ₆₇ , X ₆₈ and X ₆₉ each represent a carbon atom or a nitrogen atom, and Q ₂₀ represents a carbon atom, a six-membered aromatic hydrocarbon ring together with X ₆₆ and X ₆₇ , or 5 Q ₂₁ represents an atomic group that forms a 5- to 6-membered aromatic heterocyclic ring together with a carbon atom, X ₆₈ , X ₆₉ , and a nitrogen atom. To express. X _h and X _k represent a substituent having a van der Waals volume of 20 mm or more. m2 and n2 each represents 0 or 1. However, m2 + n2 ≧ 1.
X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). _{2 -, - C (= O} ) -, - C (= NR) -, - S (O) -, or, -SO ₂ - represents a. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ] 2. An orthometal complex having at least one partial structure selected from the group consisting of the following general formulas (11) to (14) or a tautomer of the partial structure as a partial structure. The organic electroluminescent element material of any one of -3.

[Wherein, X ₇₁ , X ₇₂ , X ₇₃ and X ₇₄ each represent a carbon atom or a nitrogen atom, Q ₂₂ represents a carbon atom, a 6-membered aromatic hydrocarbon ring together with X ₇₁ and X ₇₂ , or a 5-membered Represents an atomic group that forms a 6-membered aromatic heterocyclic ring, and Q ₂₃ represents an atomic group that forms a 5-membered to 6-membered aromatic heterocyclic ring with a carbon atom, X ₇₃ , X ₇₄ , and a nitrogen atom. Q ₂₄ forms an aromatic hydrocarbon ring or an aromatic heterocyclic ring together with the carbon atom. Q ₂₅ forms an aromatic heterocycle with the nitrogen atom. X ₀ is —O—, —S—, —CH ₂ —, —CH (R) —, —C (R) ₂ —, —N (R) —, —P (R) —, —Si (R). _{2 -, - C (= O} ) -, - C (= NR) -, - S (O) -, or, -SO ₂ - represents a. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ] The organic electroluminescent element material according to claim 2, wherein X ₁ and X _{2 in} the general formula (A) are each an anion selected from the following group.

[Wherein, R ₆₁ represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R ₆₂ represents a substituent, n8 represents an integer of 0 to 3. ] The minus monovalent bidentate ligand formed by X ₃ -L ₁ -X ₄ of the general formula (B) is selected from the following partial structures or partial structures represented by tautomers of the partial structures The organic electroluminescent element material according to claim 2, wherein

[Wherein R ₆₃ , R ₆₄ and R ₆₆ each represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R ₆₅ represents a substituent, n9 is an integer of 0 to 3, n10 represents an integer of 0 to 2. R ₆₇ represents R ₆₈ —CO— or R ₆₈ —SO ₂ —, and R ₆₈ represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. Q ₂₈ forms a 5- to 6-membered aromatic heterocycle with carbon and nitrogen. Q ₂₉ and Q ₃₀ each represents an atomic group that forms a 5-membered aromatic heterocycle with carbon and nitrogen. ] From the partial structure which the minus bivalent bidentate ligand formed by X < ₅ > -L < ₂ > -X < ₆ > of the said general formula (C) represents with the partial structure quoted below or the tautomer of this partial structure. The organic electroluminescence device material according to claim 2, wherein the material is selected.

[Wherein R ₆₉ , R ₇₀ , R ₇₁ and R ₇₂ each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. nA represents 1 or 2. R ₇₃ and R ₇₄ each represent R ₇₈ —CO— or R ₇₈ —SO ₂ —, and R ₇₈ represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R ₇₅ , R ₇₆ and R ₇₇ each represents a substituent, and nB represents 0 or 1. nC and nD represent an integer selected from 0 to 2. X ₈₁ , X ₈₂ , X ₈₃ , X ₈₄ , X ₈₅ , and X ₈₆ are selected from C—R ₇₉ and N, and together with a carbon atom and a nitrogen atom, form a 5-membered heteroaromatic ring. R ₇₉ represents a hydrogen atom or a substituent. ] Wherein X ₇ of the general formula (D) The organic electroluminescent device material according to any one of claims 1-3, characterized in that selected from uncharged ligands below.

[Wherein, R ₈₀ , R ₈₂ , R ₈₃ , R ₈₄ and R ₈₅ each represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R ₈₁ represents a substituent, and nE represents an integer of 0-2. ] The organic electroluminescence element material according to any one of claims 1 to 3, wherein X _{8 in the} general formula (E) is selected from the following anion group.

[Wherein R ₈₆ represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R ₈₇ represents a substituent, and nF represents an integer selected from 0 to 3. ] The organic electroluminescent element material containing the organic electroluminescent element material of any one of Claims 1-15. An organic electroluminescent device comprising a light emitting layer as a constituent layer, wherein the light emitting layer contains the organic electroluminescent device material according to any one of claims 1 to 15. An organic electroluminescence device comprising a hole blocking layer as a constituent layer, wherein the hole blocking layer contains the organic electroluminescence device material according to any one of claims 1 to 15. The organic electroluminescent element according to any one of claims 16 to 18, comprising a compound represented by the following general formula (33) in a light emitting layer or a layer adjacent to the light emitting layer.

[Wherein, Z ₁ represents an aromatic heterocyclic ring which may have a substituent, Z ₂ represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring which may each have a substituent, Z ₃ represents a divalent linking group or a simple bond. R ₁₀₁ represents a hydrogen atom or a substituent. ] 20. The organic electroluminescence device according to claim 19, wherein Z _{1 of the} compound represented by the general formula (33) is a 6-membered ring. 21. The organic electroluminescence device according to claim 19, wherein Z _{2 of the} compound represented by the general formula (33) is a 6-membered ring. The organic electroluminescence device according to any one of claims 19 to 21, wherein Z _{3 of the} compound represented by the general formula (33) is a bond. 23. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) has a molecular weight of 450 or more. 24. The organic electroluminescent element according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-1).

[Wherein, R _{501 to} R ₅₀₇ each independently represents a hydrogen atom or a substituent. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-2).

[Wherein, R _{511 to} R ₅₁₇ each independently represents a hydrogen atom or a substituent. ] The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (33-3).

[Wherein, R _{521 to} R ₅₂₇ each independently represents a hydrogen atom or a substituent. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-4).

[Wherein, R _{531 to} R ₅₃₇ each independently represents a hydrogen atom or a substituent. ] 24. The organic electroluminescent element according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-5).

Wherein, R ₅₄₁ to R ₅₄₈ each independently represents a hydrogen atom or a substituent. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-6).

[Wherein, R _{551 to} R ₅₅₈ each independently represents a hydrogen atom or a substituent. ] 24. The organic electroluminescent element according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-7).

[Wherein, R _{561 to} R ₅₆₇ each independently represents a hydrogen atom or a substituent. ] The compound represented by the general formula (33) is represented by the following general formula (33-8), The organic electroluminescence device according to any one of claims 19 to 23.

[Wherein, R _{571 to} R ₅₇₇ each independently represents a hydrogen atom or a substituent. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-9).

[Wherein, R _{581 to} R ₅₈₈ each represents a hydrogen atom or a substituent. ] 24. The organic electroluminescent element according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (33-10).

[Wherein, R _{591 to} R ₅₉₈ each represent a hydrogen atom or a substituent. ] The compound represented by the general formula (33) has at least one group represented by any one of the following general formulas (34-1) to (34-8). Organic electroluminescent element of any one of these.

[In the formula, R _{502 to} R ₅₀₇ , R _{512 to} R ₅₁₇ , R _{522 to} R ₅₂₇ , R _{532 to} R ₅₃₇ , R _{542 to} R ₅₄₈ , R _{552 to} R ₅₅₈ , R _{562 to} R ₅₆₇ , R _{572 to} R ₅₇₇ each independently represents a hydrogen atom or a substituent, and the substituents may be the same or different. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (35).

[Wherein, R _{601 to} R ₆₀₆ each independently represents a hydrogen atom or a substituent, and at least one of R _{601 to} R ₆₀₆ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (36).

[Wherein, R _{611 to} R ₆₂₀ each independently represents a hydrogen atom or a substituent, and at least one of R _{611 to} R ₆₂₀ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ] The compound represented by the general formula (33) is represented by the following general formula (37), The organic electroluminescence device according to any one of claims 19 to 23.

[Wherein, R _{621 to} R ₆₂₃ each independently represents a hydrogen atom or a substituent, and at least one of R _{621 to} R ₆₂₃ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (38).

[Wherein, R _{631 to} R ₆₄₅ each independently represent a hydrogen atom or a substituent, and at least one of R _{631 to} R ₆₄₅ is represented by the above general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (39).

[Wherein, R _{651 to} R ₆₅₆ each independently represents a hydrogen atom or a substituent, and at least one of R _{651 to} R ₆₅₆ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. na represents an integer of 0 to 5, and nb represents an integer of 1 to 6, but the sum of na and nb is 6. ] The compound represented by the general formula (33) is represented by the following general formula (40), The organic electroluminescence device according to any one of claims 19 to 23.

[Wherein, R _{661 to} R ₆₇₂ each independently represents a hydrogen atom or a substituent, and at least one of R _{661 to} R ₆₇₂ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ] The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (41).

[Wherein, R _{681 to} R ₆₈₈ each independently represents a hydrogen atom or a substituent, and at least one of R _{681 to} R ₆₈₈ is represented by the general formulas (34-1) to (34-4). Represents at least one group selected from the following groups. ] The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (42).

[Wherein, R _{691 to} R ₇₀₀ each independently represents a hydrogen atom or a substituent, and L ₁ represents a divalent linking group. At least one of R _{691 to} R ₇₀₀ represents at least one group selected from the groups represented by the general formulas (34-1) to (34-4). ] The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (43).

[Wherein, R ₁ and R ₂ each independently represents a hydrogen atom or a substituent. n and m each represent an integer of 1 to 2, and k and l each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (44).

[Wherein, R ₁ and R ₂ each independently represents a hydrogen atom or a substituent. n and m each represent an integer of 1 to 2, and k and l each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (45).

[Wherein, R ₁ and R ₂ each independently represents a hydrogen atom or a substituent. n and m each represent an integer of 1 to 2, and k and l each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. ] The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (46).

[Wherein, R ₁ and R ₂ each independently represents a hydrogen atom or a substituent. n and m each represent an integer of 1 to 2, and k and l each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. ] The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (47).

[Wherein, R ₁ and R ₂ each independently represents a hydrogen atom or a substituent. n and m each represent an integer of 1 to 2, and k and l each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. Z ₁ , Z ₂ , Z ₃ and Z ₄ each represents a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom. ] The organic electroluminescence device according to any one of claims 19 to 23, wherein the compound represented by the general formula (33) is represented by the following general formula (48).

[Wherein, o and p each represent an integer of 1 to 3, and Ar ₁ and Ar ₂ each represent an arylene group or a divalent aromatic heterocyclic group. Z ₁ and Z ₂ each represent a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom, and L represents a divalent linking group. ] 24. The organic electroluminescence device according to claim 19, wherein the compound represented by the general formula (33) is represented by the following general formula (49).

[Wherein, o and p each represent an integer of 1 to 3, and Ar ₁ and Ar ₂ each represent a divalent arylene group or a divalent aromatic heterocyclic group. Z ₁ , Z ₂ , Z ₃ and Z ₄ each represents a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom, and L represents a divalent linking group. ] 50. A display device comprising the organic electroluminescent element according to claim 16. An illuminating device comprising the organic electroluminescence element according to any one of claims 16 to 49.

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