JP5125502B2 - Organic electroluminescence element material, organic electroluminescence element - Google Patents

Organic electroluminescence element material, organic electroluminescence element Download PDF

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JP5125502B2
JP5125502B2 JP2007508045A JP2007508045A JP5125502B2 JP 5125502 B2 JP5125502 B2 JP 5125502B2 JP 2007508045 A JP2007508045 A JP 2007508045A JP 2007508045 A JP2007508045 A JP 2007508045A JP 5125502 B2 JP5125502 B2 JP 5125502B2
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JPWO2006098120A1 (en
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雅人 西関
智寛 押山
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コニカミノルタホールディングス株式会社
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Description

The present invention relates organic electroluminescence device material, an organic electroluminescence element.

  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, as an organic electroluminescence element material (hereinafter, referred to as an organic EL element material), a small amount of phosphor is doped into a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative to improve emission luminance. The life of the organic EL element is extended.

  In addition, an organic EL device having an organic light emitting layer doped with a trace amount of a phosphor as an 8-hydroxyquinoline aluminum complex as a host compound (for example, JP-A 63-264692), an 8-hydroxyquinoline aluminum complex As a host compound, an organic EL element having an organic light emitting layer doped with a quinacridone dye (for example, Japanese Patent Laid-Open No. 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 the conventional organic EL device because the emitted light is derived from phosphorescence. There was a problem that the light emission lifetime was lower than that of conventional organic EL elements. As described above, the phosphorescent high-efficiency light-emitting material is not capable of sufficiently achieving practical performance because it is difficult to shorten the emission wavelength and improve the light emission lifetime of the organic EL element.

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 life of the organic EL device is greatly deteriorated, and thus improvement has been demanded.
JP 2002-332291 A JP 2002-332292 A JP 2002-338588 A JP 2002-226495 A JP 2002-234894 A WO02 / 15645 specification JP 2003-123982 A JP 2002-117978 A JP 2003-146996 A WO04 / 016711 Specification 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 problems of the object of the present invention exhibit high luminous efficiency and a long organic EL device material emission lifetime is to provide an organic EL element.

The above object of the present invention is achieved by the following configurations.
The present invention and preferred embodiments of the present invention are shown below.

(1) the following general formula (5) or organic electroluminescence element material you wherein the ortho metal complex represented by (6).

(In the formula, M represents iridium, platinum, palladium, or osmium . M1 is 1 or 2, and n1 is 1 or 2. However, m1 + n1 is 2 or 3, which corresponds to the charge of M. X 11 represents a carbon atom or a nitrogen atom, Q 11 is .X 12 that represents an atomic group for forming a ring a is an aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocyclic 6-membered together with carbon atoms and X 11 represents a carbon atom or a nitrogen atom, Q 12 is .X 1 representing an atom group forming a ring B is an aromatic heterocyclic 5-6 membered together with the nitrogen atom and X 12 is O, S, CH 2, CHR , CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO 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 Represents.

X 21 represents a carbon atom or a nitrogen atom, and Q 21 represents an atomic group that together with the carbon atom and X 21 forms a ring C that is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. . X 22 represents a carbon atom or a nitrogen atom, and Q 22 represents an atomic group that forms a ring D that is a 5- to 6-membered aromatic heterocyclic ring together with the nitrogen atom and X 22 . X 2 represents O, S, CH 2, CHR , CR 2, NR, PR, SiR 2, C = O, C = NR, SO 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. However, ring A and ring C, ring B and ring D are not the same at the same time . )

(In the formula, M represents iridium, platinum, palladium, or osmium . M2 is 1 or 2, and n2 is 1 or 2. However, m2 + n2 is 2 or 3, which corresponds to the charge of M. X 11 represents a carbon atom or a nitrogen atom, Q 11 is .X 12 that represents an atomic group for forming a ring a is an aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocyclic 6-membered together with carbon atoms and X 11 represents a carbon atom or a nitrogen atom, Q 12 is .X 1 representing an atom group forming a ring B is an aromatic heterocyclic 5-6 membered together with the nitrogen atom and X 12 is O, S, CH 2, CHR , CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO 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 .X 31 representing a, X 32 is a nitrogen atom or a phosphorus source The expressed by X 3 is X 31 -X 3 -X 32, the following general formula (4-10), (4-11), (4-18), (4-20), (4-21) or ( 4-22) represents a group of atoms forming a bidentate ligand having the partial structure represented by 4-22) or a tautomer thereof as a partial structure.
(Wherein R 82 , R 86 and R 87 represent a hydrogen atom or a substituent, n 81 represents an integer of 0 to 3, and n 83 represents an integer of 0 to 2. R 84 , R 85 , R 88 and R 89 represent an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group, R 88 and R 89 may be an aryloxy group, Q 81 is 5 together with carbon and nitrogen. It represents an atomic group forming an aromatic heterocyclic ring 6-membered, Q 82 represents an atomic group forming an aromatic heterocyclic ring of 5-membered carbon, together with the nitrogen.)
(2) In the general formula (5), at least one of the aromatic heterocycle B or the aromatic heterocycle D is a 6-membered ring and the other is a 5-membered ring. The organic electroluminescent element material as described.
(3) The organic electroluminescent element material as described in (1) above, wherein in the general formula (6), the aromatic heterocyclic ring B is a 6-membered ring.

(4) The orthometal complex having a partial structure represented by the following general formulas (1-1) to (1-150) or a tautomer thereof as a partial structure : The organic electroluminescent element material as described in 2) .

(In the formula, M represents iridium, platinum, palladium or osmium . R 11 and R 12 each represents a substituent, and n 11 and n 12 each represents an integer selected from 0 to 2. X 13 and X 14 each represent > N—R 13 , —O— or —S—, wherein R 13 represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group, X 15 , X 16 , X 17 and X 18 each represent> N—R 16 , —O— or —S—, wherein 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 represents CH or N, and any one or two of them are N. X 0 is O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO or SO 2 , where R is an alkyl And represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.)
(5) The orthometal complex having a partial structure represented by the following general formulas (2-1) to (2-50) or a tautomer thereof as a partial structure: 3) The organic electroluminescence device material according to any one of 3).

(In the formula, M represents iridium, platinum, palladium, or osmium . R 21 and R 22 each represents a substituent, and n 21 and n 22 each represents an integer selected from 0 to 2. X 23 represents> N—R. 23 represents —O— or —S—, R 23 represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group, and X 24 and X 25 are> N —R 24 , —O— or —S—, wherein R 24 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 26 , X 27 , X 28 each represents CH or N, and any one or two are N. X 0 is O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═ NR, SO or SO 2 R represents an alkyl group, a cycloalkyl group, an alkeni And represents an aryl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.)
(6) The ortho metal complex having a partial structure represented by the following general formulas (3-1) to (3-10) or a tautomer thereof as a partial structure: The organic electroluminescent element material according to any one of 3).

(Wherein, M is iridium, platinum, .R 31 representing a palladium or osmium, R 32 each substituent may be the table to. A plurality of R 32 may form a ring. N31, n32 from 0-2 X 31 represents> N—R 33 , —O— or —S—, wherein R 33 represents an alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic ring. .X 32, X 33 representing a group,> N-R 34, represents -O- or -S-. X 32 is> may be SO 2. R 34 is a hydrogen atom, an alkyl group, a cycloalkyl A group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group, wherein X 34 , X 35 and X 36 each represents CH or N, and any one or two of them are N. X 0 is O, S, CH 2, CHR , CR 2, NR, PR, SiR 2, C = O, C = N , .R representing the SO or SO 2 represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.)
(7) An ortho metal complex having a partial structure represented by the following general formula (7) or a tautomer thereof as a partial structure, any of the above (1) to (3) and (6) 2. The organic electroluminescent element material according to item 1.

(In the formula, M represents iridium, platinum, palladium or osmium . X 41 represents a carbon atom or a nitrogen atom, and Q 41 represents a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic hydrocarbon ring together with the carbon atom and X 41 Represents an atomic group forming ring E, which is an aromatic heterocyclic ring, R 41 represents a substituent, n4 represents an integer selected from 0 to 3. Xa represents —N (Ra) 2 , —O—Ra or —R— represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group, and when Xa is —N (Ra) 2 , the two Ras are the same. X 4 represents O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO or SO 2 , where R is alkyl Group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group Represents an aromatic heterocyclic group.)
(8) The organic electroluminescence as described in (7) above, which is an orthometal complex having a partial structure represented by the following general formula (8) or (9) or a tautomer thereof as a partial structure Element material.

(In the formula, M represents iridium, platinum, palladium, or osmium . R 51 , R 52 , R 53 , and R 54 each represents a hydrogen atom or an electron-donating substituent, and at least one of them represents an electron-donating group. is a substituent .R 56, R 57, R 58 , R 59 each represent a hydrogen atom or a substituent, .R 50 at least one of R 56, R 58 is an electron-withdrawing group, R 55 Represents a substituent, and n51 and n52 represent an integer selected from 0 to 3. Xa represents —N (Ra) 2 , —O—Ra or —S—Ra, where Ra represents an alkyl group, a cycloalkyl group, alkenyl group, an aryl group, if .Xa representing a heterocyclic group or an aromatic heterocyclic group of -N (Ra) 2, 2 two Ra good be different even in the same .X 5 is O, S , CH 2, CHR, CR 2 , NR, PR, SiR 2, C = O, C = N , .R representing the SO or SO 2 represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.)
(9) The orthometal complex having a partial structure represented by the following general formula (10) or a tautomer thereof as a partial structure, according to any one of the above (1) to (8) The organic electroluminescent element material as described.

(In the formula, M represents iridium, platinum, palladium or osmium . X 61 , X 62 , X 63 and X 64 each represents a carbon atom or a nitrogen atom, and Q 61 represents a carbon atom and X 61 and X 63 together. It represents an aromatic hydrocarbon ring or an atomic group forming a ring F is a 5-6 membered aromatic heterocyclic 6-membered, Q 62 is an aromatic heterocyclic 5-6 membered together with the nitrogen atom and X 62, X 64 .X represents an atomic group forming a ring G is a ring b, X c represents a substituent van der Waals volume is 20 Å 3 or more .M6, the n6 represents 0 or 1. However, m6 + n6 ≧ 1 X 6 represents O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO or SO 2 , R represents an alkyl group, a cycloalkyl group, an alkenyl group Represents an aryl group, a heterocyclic group or an aromatic heterocyclic group.)
(10) The organic electroluminescence as described in (8) above, which is an orthometal complex having a partial structure represented by the following general formulas (11) to (14) or a tautomer thereof as a partial structure Element material.

(In the formula, M represents iridium, platinum, palladium or osmium . X 71 , X 72 , X 73 and X 74 each represents a carbon atom or a nitrogen atom, and Q 71 represents a carbon atom, together with X 71 and X 73. represents an atomic group for forming a 6-membered a aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocyclic ring H, Q 72 is a nitrogen atom, X 72, aromatic 5-6 membered with X 74 complex .Q 73 which represents a group of atoms forming a ring K is a ring forming an aromatic heterocyclic ring together .Q 74 nitrogen atom represent an atomic group forming an aromatic hydrocarbon ring or aromatic heterocyclic ring with the carbon atoms X 7 represents O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO or SO 2 , R represents an alkyl group or a cycloalkyl group Represents an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.)
(11) In the present invention, the bidentate ligand formed by X 31 —X 3 —X 32 in the general formula (6) is represented by the following general formulas (4-10), (4-11). ), (4-18), (4-20), characterized by having as a partial structure or partial structure a tautomer thereof represented by the (4-21) or (4-22).

(Wherein R 81 represents R 80 —CO— or R 80 —SO 2 —, and R 80 represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R 82 , R 83 , R 86 and R 87 represent a hydrogen atom or a substituent, n 81 represents an integer of 0 to 3, and n 82 and n 83 represent an integer of 0 to 2. R 84 , R 85 and R 88 , R 89 represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group, R 88 and R 89 may be an aryloxy group, and Q 81 is 5 to 5 together with carbon and nitrogen . represents an atomic group for forming a 6-membered aromatic heterocyclic ring, Q 82, Q 83 represents an atomic group forming an aromatic heterocyclic ring of 5-membered carbon, together with the nitrogen.)
(12) The organic electroluminescent element material according to any one of (1) to (11), wherein M is iridium or platinum.

(13) An organic electroluminescent element comprising the organic electroluminescent element material according to any one of (1) to (12) .

(14) An organic electroluminescent device comprising a light emitting layer as a constituent layer, and the light emitting layer containing the organic electroluminescent device material according to any one of (1) to (12) .

(15) An organic material having a hole blocking layer as a constituent layer, wherein the hole blocking layer contains the organic electroluminescence element material according to any one of (1) to (12). Electroluminescence element.

(16) The organic electroluminescence device as described in any one of (13) to (15) above, which comprises a compound represented by the following general formula (1A).

(In the formula, Z 1 represents an aromatic heterocyclic ring, Z 2 represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring, Z 3 represents a divalent linking group or a simple bond. R 101 represents a hydrogen atom. Or represents a substituent.)
(17) The organic electroluminescence device according to (16) , wherein Z 1 of the compound represented by the general formula (1A) is a 6-membered ring.

(18) The organic electroluminescence device as described in (16) or (17) above, wherein Z 2 of the compound represented by the general formula (1A) is a 6-membered ring.

(19) The organic electroluminescence device according to any one of (16) to (18) , wherein Z 3 of the compound represented by the general formula (1A) is a bond.

(20) The organic electroluminescence device according to any one of (16) to (19) , wherein the compound represented by the general formula (1A) has a molecular weight of 450 or more.

(21) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) has a molecular weight of 450 or more.

(In the formula, R 501 to R 507 each independently represent a hydrogen atom or a substituent.)
(22) The organic electro of any one of the above (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (1A-2) Luminescence element.

(Wherein R511 to R517 each independently represents a hydrogen atom or a substituent)
(23) The organic electro of any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (1A-3) Luminescence element.

(Wherein R 521 to R 527 each independently represents a hydrogen atom or a substituent)
(24) The organic electro of any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (1A-4) Luminescence element.

(In the formula, R 531 to R 537 each independently represents a hydrogen atom or a substituent.)
(25) The organic electro of any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (1A-5) Luminescence element.

(Wherein, represents a hydrogen atom or a substituent each independently R 541 to R 548 in.)
(26) The organic electro of any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (1A-6): Luminescence element.

(Wherein R 551 to R 558 each independently represents a hydrogen atom or a substituent)
(27) The organic electro of any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (1A-7) Luminescence element.

(In the formula, R 561 to R 567 each independently represents a hydrogen atom or a substituent.)
(28) The organic electro of any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (1A-8): Luminescence element.

(Wherein R 571 to R 577 each independently represents a hydrogen atom or a substituent)
(29) The organic electro of any one of the above (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (1A-9) Luminescence element.

(In the formula, R represents a hydrogen atom or a substituent. The plurality of R may be the same or different.)
(30) The organic electro of any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (1A-10) Luminescence element.

(In the formula, R represents a hydrogen atom or a substituent. The plurality of R may be the same or different.)
(31) The compound represented by the general formula (1A) has at least one group represented by any one of the following general formulas (2A-1) to (2A-10) (16) The organic electroluminescent element of any one of ()-(20) .

(Wherein, R 502 ~R 507, R 512 ~R 517, R 522 ~R 527, R 532 ~R 537, R 542 ~R 548, R 552 ~R 558, R 562 ~R 567, R 572 ~R 577 , R 582 to R 588 and R 592 to R 598 each independently represent a hydrogen atom or a substituent, and the substituents may be the same or different.
(32) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (3A) .

(Wherein R 601 to R 606 each independently represents a hydrogen atom or a substituent, but at least one of R 601 to R 606 is represented by the general formulas (2-1) to (2-10)). Represents at least one group selected from the group)
(33) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (4A) .

(Wherein R 611 to R 620 each independently represents a hydrogen atom or a substituent, but at least one of R 611 to R 620 is represented by the general formulas (2A-1) to (2A-10)). Represents at least one group selected from the group)
(34) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (5A) .

(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 (2A-1) to (2A-10)). Represents at least one group selected from the group)
(35) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (6A) .

(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 general formulas (2A-1) to (2A-10)). Represents at least one group selected from the group)
(36) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (7A) .

(Wherein R 651 to R 656 each independently represent a hydrogen atom or a substituent, but at least one of R 651 to R 656 is represented by the general formulas (2-1) to (2-10)) And at least one group selected from the group, na represents an integer of 0 to 5, nb represents an integer of 1 to 6, and the sum of na and nb is 6.)
(37) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (8A) .

(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 (2A-1) to (2A-10)) Represents at least one group selected from the group)
(38) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (9A) .

(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 (2A-1) to (2A-10)). Represents at least one group selected from the group)
(39) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (10A) .

(Wherein R 691 to R 700 each independently represents a hydrogen atom or a substituent, L 1 represents a divalent linking group. At least one of R 691 to R 700 represents the above general formula (2A-1 ) Represents at least one group selected from the groups represented by (2A-10).
(40) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (11A) .

(In the formula, R 1 and R 2 each independently represents a hydrogen atom or a substituent. N and m each represents an integer of 1 to 2, and k and l each represents an integer of 3 to 4, provided that n + k. = 5 and l + m = 5.)
(41) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (12A) .

(In the formula, R 1 and R 2 each independently represents a hydrogen atom or a substituent. N and m each represents an integer of 1 to 2, and k and l each represents an integer of 3 to 4, provided that n + k. = 5 and l + m = 5.)
(42) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (13A) .

(In the formula, R 1 and R 2 each independently represents a hydrogen atom or a substituent. N and m each represents an integer of 1 to 2, and k and l each represents an integer of 3 to 4, provided that n + k. = 5 and l + m = 5.)
(43) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (14A) .

(In the formula, R 1 and R 2 each independently represents a hydrogen atom or a substituent. N and m each represents an integer of 1 to 2, and k and l each represents an integer of 3 to 4, provided that n + k. = 5 and l + m = 5.)
(44) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (15A) .

(In the formula, R 1 and R 2 each independently represents a hydrogen atom or a substituent. N and m each represents an integer of 1 to 2, and k and l each represents an integer of 3 to 4, provided that 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.
(45) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (16A) .

(Wherein, o and p each represent an integer of 1 to 3, Ar 1 and Ar 2 each represent an arylene group or a divalent aromatic heterocyclic group. Z 1 and Z 2 each represent at least one nitrogen atom. A 6-membered aromatic heterocyclic ring containing 1 and L represents a divalent linking group.)
(46) The organic electroluminescence device according to any one of (16) to (20) , wherein the compound represented by the general formula (1A) is represented by the following general formula (17A) .

(In the formula, o and p each represent an integer of 1 to 3, Ar 1 and Ar 2 each represent an arylene group or a divalent aromatic heterocyclic group. Z 1 , Z 2 , Z 3 and Z 4 are each nitrogen atom represent an aromatic heterocyclic ring containing at least one 6-membered, L represents a divalent linking group.)

The present invention show high luminous efficiency and a long organic EL device material emission lifetime, it is possible to provide an organic EL element.

It is the schematic diagram which showed an example of the display apparatus comprised from an organic EL element. 4 is a schematic diagram of a display unit A. FIG. It is a schematic diagram of a pixel. It is a schematic diagram of the display apparatus by a passive matrix system. 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 101 Organic EL element 102 Glass cover 105 Cathode 106 Organic EL layer 107 Glass substrate with a transparent electrode 108 Nitrogen gas 109 Water catching agent

  As a result of intensive investigations on the problems of conventional ortho metal complexes, the present inventors have produced a compound using a combination of a plurality of different ligands having a specific structure as a ligand of the ortho metal complex. It has been found that the organic EL element exhibits higher luminous efficiency than before and has a significantly improved luminous lifetime. The illumination device and the display device manufactured using this organic EL element similarly showed excellent characteristics.

  Although the mechanism by which such an effect is obtained has not been elucidated, by combining a plurality of different ligands, excimer emission due to self-organization or self-assembly of the organic EL element material serving as the emission center is suppressed, Estimated to achieve high luminous efficiency.

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

  In the present invention, the organic EL element containing the organic EL element material means that an organic EL element material forms any organic layer constituting the organic EL element or an organic EL element contained in the organic layer. Represent. The layer structure of the organic EL device of the present invention will be described separately in detail.

  As the content layer of the metal complex (organic EL element material) according to the present invention, a light emitting layer and / or a hole blocking layer are preferable. When it contains in a light emitting layer, the lifetime improvement of the light emission lifetime of the organic EL element which is the objective of this invention can be achieved by using as a light emitting dopant in a light emitting layer.

[Metal complex]
The metal complex represented by the general formula according to the present invention will be described.

The organic EL device material of the present invention and the preferred embodiment (1) of the present invention is an ortho metal complex represented by the general formula (5) or (6) .

In general formula (5), M represents iridium, platinum, palladium, or osmium . m1 is 1 or 2, and n1 is 1 or 2. However, m1 + n1 is 2 or 3, which matches the charge of M. X 11 represents a carbon atom or a nitrogen atom, and Q 11 represents an atomic group that forms, together with the carbon atom and X 11 , a ring A that is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X 12 represents a carbon atom or a nitrogen atom, and Q 12 represents an atomic group that forms a ring B that is a 5- or 6-membered aromatic heterocyclic ring together with the nitrogen atom and X 12 . X 1 represents O, S, CH 2, CHR , CR 2, NR, PR, SiR 2, C = O, C = NR, SO 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.

X 11 represents a carbon atom or a nitrogen atom, and Q 11 represents an atomic group that forms, together with the carbon atom and X 11 , a ring A that is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X 12 represents a carbon atom or a nitrogen atom, and Q 12 represents an atomic group that forms a ring B that is a 5- or 6-membered aromatic heterocyclic ring together with the nitrogen atom and X 12 . X 1 represents O, S, CH 2, CHR , CR 2, NR, PR, SiR 2, C = O, C = NR, SO 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.

X 21 represents a carbon atom or a nitrogen atom, and Q 21 represents an atomic group that forms a ring C that is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring together with the carbon atom and X 21 . X 22 represents a carbon atom or a nitrogen atom, and Q 22 represents an atomic group that forms a ring D that is a 5- to 6-membered aromatic heterocyclic ring together with the nitrogen atom and X 22 . X 2 represents O, S, CH 2, CHR , CR 2, NR, PR, SiR 2, C = O, C = NR, SO 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. However, ring A and ring C, ring B and ring D are not the same at the same time.

  Examples of the 6-membered aromatic hydrocarbon ring include a benzene ring.

  Examples of the 5- to 6-membered aromatic heterocycle include an oxazole ring, a thiophene ring, a furan ring, a pyrrole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, a pyrazole ring, and a triazole ring. Can be mentioned.

  These 6-membered aromatic hydrocarbon rings and 5- to 6-membered aromatic heterocycles are alkyl groups (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 (eg, cyclopentyl group, cyclohexyl group etc.), alkenyl group (eg, vinyl group, allyl group etc.), alkynyl group (eg, 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 (eg pyrrolidyl group) Imidazolidyl group, morpholyl group, oxazolidyl group, etc.), aromatic heterocyclic group (for example, pyridyl, for example) , Pyrimidinyl group, furyl group, pyrrolyl group, imidazolyl group, benzimidazolyl group, pyrazolyl group, pyrazinyl group, triazolyl group (for example, 1,2,4-triazol-1-yl group, 1,2,3-triazole-1- 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, A carbazolyl group, a carbolinyl group, a diazacarbazolyl group (in which one of carbon atoms constituting a carboline ring is replaced by a nitrogen atom), a quinoxalinyl group, a pyridazinyl group, a triazinyl group, a quinazolinyl group, a phthalazinyl group, An alkoxyl group (eg, Xy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxyl group (for example, cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group (for example, Phenoxy group, naphthyloxy group, etc.), alkylthio group (eg, methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group) Etc.), arylthio group (eg, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (eg, methyloxycarbonyl 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.), ureido group (for example, methylureido group, ethyl) Ureido group, pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenylureido group, naphthylureido group, 2-pyridylami Ureido group, etc.), acyl group (for example, acetyl group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group, cyclohexylcarbonyl group, octylcarbonyl group, 2-ethylhexylcarbonyl group, dodecylcarbonyl group, phenylcarbonyl group, naphthylcarbonyl group) , Pyridylcarbonyl group etc.), acyloxy group (eg acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecylcarbonyloxy group, phenylcarbonyloxy group etc.), amide group (eg methylcarbonyl) Amino group, ethylcarbonylamino group, dimethylcarbonylamino group, propylcarbonylamino group, pentylcarbonylamino group, cyclohexylcarbonylamino group, 2-ethyl Xylcarbonylamino group, octylcarbonylamino group, dodecylcarbonylamino group, phenylcarbonylamino group, naphthylcarbonylamino group, etc.), carbamoyl group (for example, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group) Pentylaminocarbonyl group, cyclohexylaminocarbonyl group, octylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, dodecylaminocarbonyl group, phenylaminocarbonyl group, naphthylaminocarbonyl group, 2-pyridylaminocarbonyl group, etc.), sulfinyl group (for example, , Methylsulfinyl group, ethylsulfinyl group, butylsulfinyl group, cyclohexylsulfinyl group, 2-ethylhexylsulfinyl group 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- May have a substituent such as an ethylhexylamino group, dodecylamino group, anilino group, naphthylamino group, 2-pyridylamino group), nitro group, cyano group, etc. And between the substituents on the heterocyclic ring to form a ring structure, it is also possible to adopt a condensed ring structure in which another aromatic hydrocarbon ring or an aromatic heterocycle with.

  The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group and aromatic heterocyclic group represented by R are the 6-membered aromatic hydrocarbon ring and 5- to 6-membered aromatic group, respectively. It is synonymous with the alkyl group, the cycloalkyl group, the alkenyl group, the aryl group, the heterocyclic group, and the aromatic heterocyclic group described as the substituent for the heterocyclic ring.

  In the general formula (5), it is preferable that at least one of the aromatic heterocycle B or the aromatic heterocycle D is a 6-membered ring and the other is a 5-membered ring.

In general formula (6), M represents iridium, platinum, palladium, or osmium . m2 is 1 or 2, and n2 is 1 or 2. However, m2 + n2 is 2 or 3, which matches the charge of M. X 11 represents a carbon atom or a nitrogen atom, and Q 11 represents an atomic group that forms, together with the carbon atom and X 11 , a ring A that is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X 12 represents a carbon atom or a nitrogen atom, and Q 12 represents an atomic group that forms a ring B that is a 5- or 6-membered aromatic heterocyclic ring together with the nitrogen atom and X 12 . X 1 represents O, S, CH 2, CHR , CR 2, NR, PR, SiR 2, C = O, C = NR, SO 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. X 31 and X 32 represent a nitrogen atom or a phosphorus atom, and X 3 is represented by the formulas (4-10), (4-11), (4-18), (4) according to X 31 -X 3 -X 32. -20) represents an atomic group forming a bidentate ligand having the partial structure represented by (4-21) or (4-22) or a tautomer thereof as a partial structure.

The 6-membered aromatic hydrocarbon ring, 5- to 6-membered aromatic heterocycle, and R have the same meanings as described in the general formula (5) .

  In the general formula (6), the aromatic heterocyclic ring B is preferably a 6-membered ring.

The organic EL device material of the aspect (4) is an ortho metal complex having a partial structure represented by the general formulas (1-1) to (1-150) or a tautomer thereof as a partial structure. Features.

In the formula, M represents iridium, platinum, palladium, or osmium . R 11 and R 12 each represent a substituent, and n 11 and n 12 each represents an integer selected from 0 to 2. X 13 and X 14 each represent> N—R 13 , —O— or —S—. R 13 represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X 15 , X 16 , 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 represents O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO 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 substituents represented by R 11 and R 12 have the same meanings as the substituents for the 6-membered aromatic hydrocarbon ring and the 5- to 6-membered aromatic heterocyclic ring described in the embodiment (1). The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).

The organic EL device material of the aspect (5) is an ortho metal complex having a partial structure represented by the general formulas (2-1) to (2-50) or a tautomer thereof as a partial structure. Features.

In the formula, M represents iridium, platinum, palladium, or osmium . R 21 and R 22 each represent a substituent, and n 21 and n 22 each represent an integer selected from 0 to 2. X 23 represents> N—R 23 , —O— or —S—. R 23 represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X 24 and X 25 each represent> N—R 24 , —O— or —S—. R 24 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 26 , X 27 and X 28 each represent CH or N, and any one or two of them are N. X 0 represents O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO 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 substituents represented by R 21 and R 22 have the same meanings as the substituents for the 6-membered aromatic hydrocarbon ring and the 5- to 6-membered aromatic heterocyclic ring described in the embodiment (1). The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).

The organic EL device material of the aspect (6) is an ortho metal complex having a partial structure represented by the general formulas (3-1) to (3-10) or a tautomer thereof as a partial structure. Features.

In the formula, M represents iridium, platinum, palladium, or osmium . R 31, R 32 each to display the substituent. A plurality of R 32 may form a ring. n31 and n32 represent an integer selected from 0 to 2. X 31 represents> N—R 33 , —O— or —S—. R 33 represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X 32 and X 33 represent> N—R 34 , —O— or —S—. X 32 may be> SO 2 . R 34 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 34 , X 35 and X 36 each represent CH or N, and any one or two of them are N. X 0 represents O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO 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 substituents represented by R 31 and R 32 have the same meanings as the substituents for the 6-membered aromatic hydrocarbon ring and 5- to 6-membered aromatic heterocyclic ring described in the embodiment (1). The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).

The organic EL device material of the aspect (7) is an ortho metal complex having a partial structure represented by the general formula (7) or a tautomer thereof as a partial structure.

In the formula, M represents iridium, platinum, palladium, or osmium . X 41 represents a carbon atom or a nitrogen atom, and Q 41 represents an atomic group that forms a ring E that is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring together with the carbon atom and X 41 . R 41 represents a substituent, and n4 represents an integer selected from 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 4 represents O, S, CH 2, CHR , CR 2, NR, PR, SiR 2, C = O, C = NR, SO 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 substituent represented by R 41 has the same meaning as the substituent of the 6-membered aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocycle described in the above embodiment (1). The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).

  An ortho metal complex having a partial structure represented by the general formula (7) or a tautomer thereof as a partial structure is obtained by converting the partial structure represented by the general formula (8) or (9) or a tautomer thereof. An ortho metal complex having a partial structure is preferable.

In the formula, M represents iridium, platinum, palladium, or osmium . R 51 , R 52 , R 53 and R 54 each represent a hydrogen atom or an electron-donating substituent, and at least one 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 50 and R 55 represent a substituent, and n51 and n52 represent an integer selected from 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 5 represents O, S, CH 2, CHR , CR 2, NR, PR, SiR 2, C = O, C = NR, SO 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 electron-donating substituent is a substituent having a negative Hammett σp value as described below, and such a substituent is more likely to give an electron to the bonding atom side than a hydrogen atom. Have

  Specific examples of the substituent exhibiting an electron donating property include a hydroxyl group, an alkoxy group (for example, methoxy group), an acetyloxy group, an amino group, a dimethylamino group, an acetylamino group, and an alkyl group (for example, methyl group, ethyl group). Group, propyl group, tert-butyl group and the like) and aryl group (for example, phenyl group, mesityl group and the like).

For example, as an electron donating group having σp of −0.20 or less, cyclopropyl group (−0.21), cyclohexyl group (−0.22), tert-butyl group (−0.20), —CH 2 Si (CH 3 ) 3 (−0.21), amino group (−0.66), hydroxylamino group (−0.34), —NHNH 2 (−0.55), —NHCONH 2 (−0. 24), —NHCH 3 (−0.84), —NHC 2 H 5 (−0.61), —NHCONHC 2 H 5 (−0.26), —NHC 4 H 9 (−0.51), − NHC 6 H 5 (−0.40), —N═CHC 6 H 5 (−0.55), —OH (−0.37), —OCH 3 (−0.27), —OCH 2 COOH (— 0.33), - OC 2 H 5 (-0.24), - OC 3 H 7 (-0.25), - OCH (CH 3) 2 (-0. 5), - OC 5 H 11 (-0.34), - OCH 2 C 6 H 5 (-0.42) , and the like.

  For Hammett's σp value, for example, the following documents can be referred to.

  Hammett's σp value refers to Hammett's substituent constant σp. Hammett's σp value is a substituent constant determined by Hammett et al. From the electronic effect of the substituent on the hydrolysis of ethyl benzoate. “Structure-activity relationship of drugs” (Nanedo: 1979), “Substituent” The groups described in “Constants for Correlation Analysis in chemistry and biology” (C. Hansch and A. Leo, John Wiley & Sons, New York, 1979) and the like can be cited.

  As the electron-donating substituent, among the above groups, an alkyl group, an alkoxy group, and an alkylamino group are most preferable.

  As said substituent, it is synonymous with the substituent of the 6-membered aromatic-hydrocarbon ring described in the said aspect (1), and a 5-6-membered aromatic heterocyclic ring. The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).

The organic EL device material of the aspect (9) is an ortho metal complex having a partial structure represented by the general formula (10) or a tautomer thereof as a partial structure.

In the formula, M represents iridium, platinum, palladium, or osmium . X 61 , X 62 , X 63 and X 64 each represent a carbon atom or a nitrogen atom, and Q 61 represents a carbon atom and X 61 and X 63 together with a 6-membered aromatic hydrocarbon ring or 5 to 6-membered aromatic. Q 62 represents an atomic group that forms a ring G that is a 5- or 6-membered aromatic heterocyclic ring together with a nitrogen atom and X 62 and X 64 . X h and X k represent a substituent having a van der Waals volume of 20 3 or more, and m6 and n6 represent 0 or 1. However, m6 + n6 ≧ 1. X 6 represents O, S, CH 2, CHR , CR 2, NR, PR, SiR 2, C = O, C = NR, SO 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 6-membered aromatic hydrocarbon ring and the 5- to 6-membered aromatic heterocyclic ring have the same meanings as described in the embodiment (1).

  The van der Waals (VDW) volume of the substituent is a parameter obtained using the molecular simulation software Cerius 2 manufactured by Accelrys, Inc., but by introducing a substituent into the benzene ring and using the Driving Force Field, The molecular structure is optimized and defined as a Volume value obtained using the Connoy Surface. Specific van der Waals (VDW) volumes of substituents 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
The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).

  The ortho metal complex having the partial structure represented by the general formula (10) or a tautomer thereof as the partial structure is obtained by converting the partial structure represented by the general formulas (11) to (14) or the tautomer thereof. An ortho metal complex having a partial structure is preferable.

In the formula, M represents iridium, platinum, palladium, or osmium . X 71 , X 72 , X 73 and X 74 each represent a carbon atom or a nitrogen atom, and Q 71 is a carbon atom, X 71 and X 73 together with a 6-membered aromatic hydrocarbon ring or a 5 to 6-membered aromatic Q 23 represents an atomic group that forms a ring K that is a 5- to 6-membered aromatic heterocyclic ring together with a nitrogen atom, X 72 , and X 74 . Q 73 represents an atomic group that forms an aromatic hydrocarbon ring or an aromatic heterocyclic ring with a carbon atom. Q 74 represents an atomic group that forms an aromatic heterocycle with a nitrogen atom. X 7 represents O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO 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 6-membered aromatic hydrocarbon ring and the 5- to 6-membered aromatic heterocyclic ring have the same meanings as described in the embodiment (1).

  The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).

In the organic EL device material of the aspect (11), the bidentate ligand formed by X 31 —X 3 —X 32 of the general formula (6) is the general formula (4-10), (4- 11) an ortho metal complex having a partial structure represented by (4-18), (4-20), (4-21) or (4-22) or a tautomer thereof as a partial structure. Features.

In the formula , R 82 , R 83 , R 86 and R 87 represent a hydrogen atom or a substituent, n 81 represents an integer of 0 to 3, and n 82 and n 83 represent an integer of 0 to 2. R 84 , R 85 , R 88 and R 89 represent an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R 88 and R 89 may be an aryloxy group. Q 81 represents an atomic group that forms a 5- to 6-membered aromatic heterocyclic ring with carbon and nitrogen, and Q 82 and Q 83 represent an atomic group that forms a 5-membered aromatic heterocyclic ring with carbon and nitrogen.

  The 5- to 6-membered aromatic heterocyclic ring has the same meaning as described in the embodiment (1).

  The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).

The organic EL element material of the aspect (12) is an ortho metal complex in which M is iridium or platinum in all the general formulas.

The ortho metal complex preferably used in the present invention and the ortho metal complex used as a reference are shown below.

  These compounds are disclosed in, for example, Organic Letter, vol13, No. 16, p2579-2581 (2001), Inorganic Chemistry, vol. 8, p 1685-1687 (1991), J. MoI. Am. Chem. Soc. , Vol123, p4304 (2001), Inorganic Chemistry, vol41, No. 12, p13056-3066 (2002), New Journal of Chemistry, vol26, p1171 (2002), and further, by applying methods such as references described in these documents.

  In the present invention, the organic EL element material is contained in any of the constituent layers (organic layers) constituting the organic EL element to produce an organic EL element.

  It is preferable that the organic EL element has a light emitting layer as a constituent layer, and the light emitting layer contains the organic EL element material. When it contains in a light emitting layer, the lifetime improvement of the light emission lifetime of the organic EL element which is the objective of this invention can be achieved by using as a light emitting dopant in a light emitting layer.

  Further, it is preferable that the organic EL element has a hole blocking layer as a constituent layer, and the hole blocking layer contains the organic EL element material.

The organic EL device of the aspect (16) contains a compound represented by the general formula (1A).

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

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

Examples of aromatic heterocycles represented by Z 1 and Z 2 include furan ring, thiophene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, 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, diazacarbazole ring (hydrocarbons constituting carboline ring) A ring in which one of the carbon atoms of the ring is further substituted with a nitrogen atom). Further, the aromatic heterocyclic ring may have a substituent represented by R 101 described later.

Examples of the aromatic hydrocarbon ring represented by Z 2 include 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 ring, picene ring, pyrene ring, pyranthrene ring, anthraanthrene A ring etc. are mentioned. Further, the aromatic hydrocarbon ring may have a substituent represented by R 101 described later.

Examples of the substituent represented by R 101 include an alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, 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.), aryl group (eg , Phenyl group, naphthyl group, etc.), aromatic heterocyclic group (for example, furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, quinazolinyl group, Phthalazinyl group, etc.), heterocyclic group (eg, pyrrolidyl group, imi Dazolidyl group, morpholyl group, oxazolidyl group, etc.), alkoxyl group (for example, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxyl group (for example, Cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group (eg, phenoxy group, naphthyloxy group, etc.), alkylthio group (eg, methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group) Etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group (eg, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (eg, methyloxycarbonyl group, etc.) Ethyloxycarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (eg, phenyloxycarbonyl group, naphthyloxycarbonyl group, etc.), sulfamoyl group (eg, aminosulfonyl group, Methylaminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octylaminosulfonyl group, dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2-pyridylaminosulfonyl group Etc.), acyl group (for example, acetyl group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group, cyclohexylcarbonyl group) Octylcarbonyl group, 2-ethylhexylcarbonyl group, dodecylcarbonyl group, phenylcarbonyl group, naphthylcarbonyl group, pyridylcarbonyl group, etc.), acyloxy group (for example, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group) Group, dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.), amide group (for example, methylcarbonylamino group, ethylcarbonylamino group, dimethylcarbonylamino group, propylcarbonylamino group, pentylcarbonylamino group, cyclohexylcarbonylamino group, 2 -Ethylhexylcarbonylamino group, octylcarbonylamino group, dodecylcarbonylamino group, phenylcarbonylamino group, naphthylcarbonylamino group, etc. ), Carbamoyl group (for example, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexylaminocarbonyl group, octylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, dodecylamino) Carbonyl 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, ethylsulfinyl group, butyl) Rufinyl 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, ethylamino group, dimethyl) Amino group, butylamino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, anilino group, naphthylamino group, 2-pyridylamino group, etc.), halogen Atom (for example, fluorine atom, chlorine atom, bromine atom, etc.), fluorinated hydrocarbon group (for example, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyano group, nitro group, Examples thereof include a hydroxyl group, a mercapto group, and a silyl group (for example, a trimethylsilyl group, a triisopropylsilyl group, a triphenylsilyl group, a phenyldiethylsilyl group, and the like).

  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.

Examples of the divalent linking group represented by Z 3 may include hydrocarbon groups such as alkylene, alkenylene, alkynylene, and arylene, and those containing a hetero atom, and also include a thiophene-2,5-diyl group, It may be a divalent linking group derived from a compound having an aromatic heterocycle such as a pyrazine-2,3-diyl group (also referred to as a heteroaromatic compound) or a chalcogen atom such as oxygen or sulfur. May be. Moreover, the group which connects and connects hetero atoms, such as an alkylimino group, a dialkylsilane diyl group, and a diaryl germane diyl group, may be sufficient.

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

In the present invention, Z 1 in the general formula (1A) is preferably a 6-membered ring. Thereby, luminous efficiency can be made higher. Further, the life can be extended. In the present invention, Z 2 is preferably a 6-membered ring. Thereby, luminous efficiency can be made higher. Further, the lifetime can be further increased. Furthermore, it is preferable to make both Z 1 and Z 2 a 6-membered ring because the luminous efficiency can be further increased. Further, it is preferable because the lifetime can be further increased. Z 3 is preferably a bond. Thereby, the luminous efficiency can be further increased and the life can be further extended. Further, the compound represented by the general formula (1A) preferably has a molecular weight of 450 or more, whereby the luminous efficiency can be increased and the life can be extended.

  Preferred among the compounds represented by the general formula (1A) are compounds represented by the general formulas (1A-1) to (1A-10).

In the general formula (1A-1), R 501 to R 507 each independently represent a hydrogen atom or a substituent. By using the compound represented by general formula (1A-1), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (1A-2), R 511 to R 517 each independently represent a hydrogen atom or a substituent. By using the compound represented by General formula (1A-2), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (1A-3), R 521 to R 527 each independently represent a hydrogen atom or a substituent. By using the compound represented by General formula (1A-3), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (1A-4), R 531 to R 537 each independently represents a hydrogen atom or a substituent. By using the compound represented by General formula (1A-4), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (1A-5), represents a hydrogen atom or a substituent each independently R 541 to R 548 is. By using the compound represented by General formula (1A-5), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (1A-6), R 551 to R 558 each independently represent a hydrogen atom or a substituent. By using the compound represented by General formula (1A-6), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (1A-7), R 561 to R 567 each independently represent a hydrogen atom or a substituent. By using the compound represented by General formula (1A-7), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (1A-8), R 571 to R 577 each independently represent a hydrogen atom or a substituent. By using the compound represented by General formula (1A-8), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

  In the general formula (1A-9), R represents a hydrogen atom or a substituent. The plurality of R may be the same or different. By using the compound represented by General formula (1A-9), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

  In the general formula (1A-10), R represents a hydrogen atom or a substituent. The plurality of R may be the same or different. By using the compound represented by General formula (1A-10), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as a long-life organic EL element.

Moreover, the compound represented by the general formula (1A) is preferably a compound having at least one group represented by any one of the general formulas (2A-1) to (2A-10). In particular, it is more preferable to have 2 to 4 groups represented by any one of the general formulas (2A-1) to (2A-10) in the molecule. In this case, the structure represented by the general formula (1A) includes a case where a portion excluding R 101 is replaced by the general formulas (2A-1) to (2A-10).

  At this time, the compounds represented by the general formulas (3A) to (17A) are particularly preferable for obtaining the effects of the present invention.

In the general formula (3A), R 601 to R 606 represent a hydrogen atom or a substituent, and at least one of R 601 to R 606 is any one of the general formulas (2A-1) to (2A-10). Represents a group represented by By using the compound represented by general formula (3A), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (4A), R 611 to R 620 represent a hydrogen atom or a substituent, and at least one of R 611 to R 620 is any one of the general formulas (2A-1) to (2A-10). Represents a group represented by By using the compound represented by General formula (4A), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (5A), R 621 to R 623 represent a hydrogen atom or a substituent, and at least one of R 621 to R 623 is any one of the general formulas (2A-1) to (2A-10). Represents a group represented by By using the compound represented by general formula (5A), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (6A), R 631 to R 645 represent a hydrogen atom or a substituent, and at least one of R 631 to R 645 is any one of the general formulas (2A-1) to (2A-10). Represents a group represented by By using the compound represented by General formula (6A), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (7A), R 651 to R 656 represent a hydrogen atom or a substituent, and at least one of R 651 to R 656 is any one of the general formulas (2A-1) to (2A-10). Represents a group represented by 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 General formula (7A), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (8A), although R 661 to R 672 represents a hydrogen atom or a substituent, at least one of the general formula R 661 ~R 672 (2A-1 ) either ~ (2A-10) Represents a group represented by By using the compound represented by General formula (8A), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (9A), R 681 to R 688 represent a hydrogen atom or a substituent, and at least one of R 681 to R 688 is any one of the general formulas (2A-1) to (2A-10). Represents a group represented by By using the compound represented by General formula (9A), it can be set as an organic EL element with higher luminous efficiency. Furthermore, it can be set as an organic EL element of longer life.

In the general formula (10A), R 691 to R 700 represent a hydrogen atom or a substituent, and at least one of R 691 to R 700 is any one of the general formulas (2A-1) to (2A-10). Represents a group represented by

Examples of the divalent linking group represented by L 1 include an alkylene group (for example, ethylene group, trimethylene group, tetramethylene group, propylene group, ethylethylene group, pentamethylene group, hexamethylene 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 (for example, , 1,5-cyclopentanediyl group etc.), alkenylene group (eg vinylene group, propenylene group etc.), alkynylene group (eg ethynylene group, 3-pentynylene group etc.), arylene group etc. In addition, a group containing a hetero atom (for example, containing a chalcogen atom such as —O— or —S—) Valent group, -N (R) - group, wherein R represents a hydrogen atom or an alkyl group, the alkyl group has the same meaning as the alkyl group represented by R 101 in the general formula (1A)), etc. Is mentioned. 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.

Further, 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 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-diyl group Alternatively, it may be a divalent linking group derived from a compound having an aromatic heterocyclic ring (also referred to as a heteroaromatic compound) such as a pyrazine-2,3-diyl group. 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 (10A), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be set as an organic EL element of longer life.

In the compounds represented by the general formula (11A) to the general formula (15A), the substituents represented by R 1 and R 2 are the substituents represented by R 101 in the general formula (1A). It is synonymous with.

In the general formula (15A), examples of the 6-membered aromatic heterocycle 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 (16A), 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.

Examples of the arylene groups represented by Ar 1 and Ar 2 include o-phenylene group, m-phenylene group, p-phenylene group, naphthalenediyl group, anthracenediyl group, naphthacenediyl group, pyrenediyl group, naphthylnaphthalenediyl group, and biphenyl. Diyl group (for example, 3,3′-biphenyldiyl group, 3,6-biphenyldiyl group, etc.), terphenyldiyl group, quaterphenyldiyl group, kinkphenyldiyl group, sexiphenyldiyl group, septiphenyldiyl Group, octylphenyldiyl group, nobiphenyldiyl group, deciphenyldiyl group and the like. The arylene group may further have a substituent described later. The divalent aromatic heterocyclic group represented by each of Ar 1 and Ar 2 is a furan ring, a thiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a benzimidazole ring, an 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, hydrocarbon ring constituting carboline ring And a divalent group derived from a ring in which the carbon atom is further substituted with a nitrogen atom. Furthermore, the aromatic heterocyclic group may have a substituent represented by R 101 .

The divalent linking group represented by L is the same as the divalent linking group represented by L 1 in the general formula (10A), but is preferably an alkylene group, -O-, -S-. A divalent group containing a chalcogen atom such as an alkylene group, most preferably an alkylene group.

In formula (17A), the arylene group represented by each of Ar 1, Ar 2 has the same meaning as the arylene group each represented by Ar 1, Ar 2 in the general formula (16A). Aromatic heterocyclic group each represented by Ar 1, Ar 2 have the same meanings as divalent aromatic heterocyclic group represented by each in the general formula (16A) in Ar 1, Ar 2.

Examples of 6-membered aromatic heterocycles each containing at least one nitrogen atom represented by Z 1 , Z 2 , Z 3 , and Z 4 include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring. Can be mentioned.

The divalent linking group represented by L is the same as the divalent linking group represented by L 1 in the general formula (10A), but is preferably an alkylene group, -O-, -S-. A divalent group containing a chalcogen atom such as an alkylene group, most preferably an alkylene group.

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

  Although the typical synthesis example of the compound based on this invention is shown below, this invention is not limited to these.

  (Synthesis of Exemplified Compound A-73)

  To a mixed solution obtained by adding 6.87 g of 4,4′-diiodobiphenyl and 6.00 g of β-carboline in 50 ml of N, N-dimethylacetamide, 4.5 g of copper powder and 7.36 g of potassium carbonate were added for 15 hours. Heated to reflux. After allowing to cool, water chloroform was added, and insolubles were removed by filtration. The organic layer was separated, washed with water and saturated brine, and concentrated under reduced pressure. The resulting residue was dissolved in acetic acid, treated with activated carbon, and recrystallized to give colorless crystals 4 of Exemplified Compound A-73. 0.2 g was obtained.

The structure of exemplary compound A-73 was confirmed by 1 H-NMR spectrum and mass spectrometry spectrum. The physical property data and spectrum data of Exemplified Compound A-73 are shown below.

Colorless crystals, melting point 200 ° C
MS (FAB) m / z: 487 (M + 1)
1 H-NMR (400 MHz, CDCl 3 ): δ / ppm 7.3-7.5 (m, 2H), 7.5-7.6 (m, 4H), 7.7-7.8 (m, 4H), 7.9-8.0 (m, 4H), 8.06 (d, J = 5.1 Hz, 2H), 8.24 (d, J = 7.8 Hz, 2H), 8.56 ( d, J = 5.1 Hz, 2H), 8.96 (s, 2H)
(Synthesis of Exemplified Compound A-74)

  0.32 g of palladium acetate and 1.17 g of tri-tert-butylphosphine were dissolved in 10 ml of anhydrous toluene, 50 mg of sodium borohydride was added, and the mixture was stirred at room temperature for 10 minutes, then δ-carboline 5.00 g, 4, 4 5.87 g of '-diiodobiphenyl and 3.42 g of sodium tert-butoxide were dispersed in 50 ml of anhydrous xylene and stirred at reflux temperature for 10 hours under a nitrogen atmosphere. The resulting reaction mixture was allowed to cool, chloroform and water were added to separate the organic layer, the organic layer was washed with water and saturated brine, and then concentrated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran. After the activated carbon treatment, 5.0 g of colorless crystals of Exemplified Compound A-74 was obtained by recrystallization.

The structure of exemplary compound A-74 was confirmed by 1 H-NMR spectrum and mass spectrometry spectrum. The physical property data and spectral data of Exemplified Compound A-74 are shown below.

MS (FAB) m / z: 487 (M + 1)
1 H-NMR (400 MHz, CDCl 3 ): δ / ppm 7.37 (dd, J = 4.7 Hz, J = 8.3 Hz, 2H), 7.4-7.5 (m, 2H), 7. 5-7.6 (m, 4H), 7.7-7.8 (m, 4H), 7.81 (dd, J = 1.2 Hz, J = 8.3 Hz, 2H), 7.9-8 0.0 (m, 4H), 8.48 (d, J = 7.8 Hz, 2H), 8.65 (dd, J = 1.2 Hz, J = 4.6 Hz, 2H)
(Synthesis of Exemplary Compound A-60)

  To a mixed solution in which 6.87 g of 4,4′-diiodobiphenyl and 6.00 g of γ-carboline were added to 50 ml of N, N-dimethylacetamide, 4.5 g of copper powder and 7.36 g of potassium carbonate were added for 15 hours. Heated to reflux. After allowing to cool, water chloroform was added, and insolubles were removed by filtration. The organic layer was separated, washed with water and saturated brine, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, crystallized in dichloromethane / cyclohexane, and exemplified Compound A-60. 4.3 g of colorless crystals were obtained.

The structure of exemplary compound A-60 was confirmed by 1 H-NMR spectrum and mass spectrometry spectrum. The physical property data and spectral data of Exemplified Compound A-60 are shown below.

MS (FAB) m / z: 487 (M + 1)
1 H-NMR (400 MHz, CDCl 3 ): δ / ppm 7.4-7.4 (m, 4H), 7.4-7.5 (m, 4H), 7.7-7.8 (m, 4H) 7.9-8.0 (m, 4H), 8.25 (d, J = 7.8 Hz, 2H), 8.57 (d, J = 5.6 Hz, 2H), 9.42 (s) , 1H)
(Synthesis of Exemplary Compound A-144)

  0.16 g of palladium acetate and 0.58 g of tri-tert-butylphosphine are dissolved in 10 ml of anhydrous toluene, 25 mg of sodium borohydride is added and stirred for 10 minutes at room temperature, then 2.00 g of δ-carboline, intermediate a3 20 g and 1.37 g of sodium tert-butoxide were dispersed in 50 ml of anhydrous xylene and stirred at reflux temperature for 10 hours under a nitrogen atmosphere. After allowing to cool, chloroform and water were added to separate the organic layer, and the organic layer was washed with water and saturated brine and then concentrated under reduced pressure. The resulting residue was recrystallized from acetic acid to give Example Compound A-144. 1.5 g of colorless crystals were obtained.

The structure of Example Compound A-144 was confirmed by 1 H-NMR spectrum and mass spectrometry spectrum. The spectral data of Example Compound A-144 are as follows.

MS (FAB) m / z: 647 (M + 1)
1 H-NMR (400 MHz, CDCl 3 ): δ / ppm 1.80 (S, 12H), 7.27 (S, 4H), 7.34 (dd, J = 4.9 Hz, J = 8.3 Hz, 2H), 7.3-7.4 (m, 2H), 7.4-7.5 (m, 12H), 7.76 (dd, J = 1.3 Hz, J = 8.3 Hz, 2H), 8.45 (d, J = 7.8 Hz, 2H), 8.63 (dd, J = 1.3 Hz, J = 4.9 Hz, 2H)
(Synthesis of Exemplary Compound A-143)

  Add 4,5'-dichloro-3,3'-bipyridyl 0.85 g, diamine b 0.59 g, dibenzylideneacetone palladium 44 mg, imidazolium salt 36 mg, sodium tert-butoxide 1.09 g to 5 ml dimethoxyethane, 80 The mixture was stirred at 24 ° C. for 24 hours. After allowing to cool, chloroform and water are added to separate the organic layer, and the organic layer is washed with water and saturated brine and then concentrated under reduced pressure. The resulting residue is recrystallized from ethyl acetate and exemplified Compound A-143. 0.3 g of colorless crystals were obtained.

The structure of Example Compound A-143 was confirmed by 1 H-NMR spectrum and mass spectrometry spectrum. The spectrum data of exemplary compound A-143 are shown below.

MS (FAB) m / z: 639 (M + 1)
1 H-NMR (400 MHz, CDCl 3 ): δ / ppm 7.46 (d, J = 5.7 Hz, 4H), 7.6-7.7 (m, 4H), 7.8-7.9 ( m, 4H), 8.67 (d, J = 5.7 Hz, 4H), 9.51 (S, 4H)
(Synthesis of Exemplary Compound A-145)
In the synthesis of Exemplary Compound A-143, except that one pyridine ring of 4,4′-dichloro-3,3′-bipyridyl was changed to benzene, except that 3- (2-chlorophenyl) -4-chloropyridine was used. Similarly, exemplary compound A-145 was synthesized.

The structure of exemplary compound A-145 was confirmed by 1 H-NMR spectrum and mass spectrometry spectrum. The spectrum data of exemplary compound A-145 are shown below.

MS (FAB) m / z: 637 (M + 1)
1 H-NMR (400 MHz, CDCl 3 ): δ / ppm 7.3-7.4 (m, 2H), 7.6-7.7 (m, 4H), 7.7-7.8 (m, 4H) 7.8-7.9 (m, 4H), 8.06 (d, J = 5.3 Hz, 2H), 8.23 (d, J = 7.8 Hz, 2H), 8.56 (d , J = 5.3 Hz, 2H), 8.96 (S, 2H)
In addition to the above synthesis examples, the azacarbazole rings and chloroplasts of these compounds are described in J. Org. Chem. Soc. Perkin Trans. 1, 1505-1510 (1999), Pol. J. et al. Chem. , 54, 1585 (1980), (Tetrahedron
Lett. 41 (2000), 481-484). Introduction of synthesized azacarbazole ring or its chloroplast and aromatic ring, heterocyclic ring, alkyl group, etc. into the core or linking group is known as Ullman coupling, coupling using Pd catalyst, Suzuki coupling, etc. This method can be used.

  The compound according to the present invention preferably has a molecular weight of 400 or more, more preferably 450 or more, still more preferably 600 or more, and particularly preferably a molecular weight of 800 or more. As a result, the glass transition temperature is raised, the thermal stability is improved, and the life can be further extended.

Next, the constituent layers of the organic EL device of the present invention will be described in detail. In this invention, although the preferable specific example of the layer structure of an organic EL element is shown below, this invention is not limited to these. (I) Anode / light emitting layer / electron transport layer / cathode (ii) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (iii) Anode / hole transport layer / light emitting layer / hole blocking layer / electron Transport layer / cathode (iv) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode (v) anode / anode buffer layer / hole transport layer / light emitting layer / hole Blocking layer / electron transport layer / cathode buffer layer / cathode << Anode >>
As the anode in the organic EL element, an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 and ZnO. Alternatively, an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used. For the anode, these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method. ), A pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. When light emission is extracted from the anode, it is desirable that the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred Ω / □ or less. Further, although the film thickness depends on the material, it is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.

"cathode"
On the other hand, as the cathode, a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like. Among these, from the point of durability against electron injection and oxidation, etc., a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this, for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually selected in the range of 10 nm to 5 μm, preferably 50 to 200 nm. In order to transmit the emitted light, if either one of the anode or the cathode of the organic EL element is transparent or translucent, the emission luminance is advantageously improved.

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

  Next, an injection layer, a blocking layer, an electron transport layer, and the like used as 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, it exists between the anode and the light emitting layer or the hole transport layer and between the cathode and the light emitting layer or the electron transport layer. May be.

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

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

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

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

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

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

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

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

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

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

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

  Further, a plurality of known host compounds may be used in combination. By using a plurality of types of host compounds, it is possible to adjust the movement of charges, and the organic EL element can be made highly efficient. In addition, by using a plurality of phosphorescent compounds, it is possible to mix different light emission, thereby obtaining an arbitrary emission color. White light emission is possible by adjusting the kind of phosphorescent compound and the amount of doping, and can also be applied to illumination and backlight.

  As these known host compounds, compounds having a hole transporting ability and an electron transporting ability, preventing the emission of longer wavelengths, and having a high Tg (glass transition temperature) are preferable.

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

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

  Moreover, the light emitting layer may contain the host compound which has a fluorescence maximum wavelength further as a host compound. In this case, the energy transfer from the other host compound and the phosphorescent compound to the fluorescent compound allows electroluminescence as an organic EL element to be emitted from the other host compound having a fluorescence maximum wavelength. A host compound having a fluorescence maximum wavelength is preferably a compound having a high fluorescence quantum yield in a solution state. Here, the fluorescence quantum yield is preferably 10% or more, particularly preferably 30% or more. Specific host compounds having a maximum fluorescence wavelength include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, and pyrylium dyes. Perylene dyes, stilbene dyes, polythiophene dyes, and the like. The fluorescence quantum yield can be measured by the method described in 362 (1992, Maruzen) of Spectroscopic II of the Fourth Edition Experimental Chemistry Course 7.

(Phosphorescent compound)
The material used for the light emitting layer (hereinafter referred to as the light emitting material) preferably contains a phosphorescent compound at the same time as the host compound. Thereby, it can be set as an organic EL element with higher luminous efficiency.

  The phosphorescent compound according to the present invention is a compound in which light emission from an excited triplet is observed, is a compound that emits phosphorescence at room temperature (25 ° C.), and has a phosphorescence quantum yield of 0.2 at 25 ° C. 01 or more compounds. The phosphorescence quantum yield is preferably 0.1 or more. The phosphorescence quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of Experimental Chemistry Course 4 of the 4th edition. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence quantum yield used in the present invention only needs to achieve the above phosphorescence quantum yield in any solvent.

  There are two types of light emission of the phosphorescent compound in principle. One is the recombination of the carrier on the host compound to which the carrier is transported to generate an excited state of the host compound, and this energy is transferred to the phosphorescent compound. The energy transfer type is to obtain light emission from the phosphorescent compound by moving to the other, and the other is that the phosphorescent compound becomes a carrier trap, and carrier recombination occurs on the phosphorescent compound, and the phosphorescent compound emits light. Although it is a carrier trap type in which light emission is obtained, in any case, it is a condition that the excited state energy of the phosphorescent compound is lower than the excited state energy of the host compound.

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

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

  Although the specific example of a phosphorescent compound is shown below, this invention is not limited to these. These compounds are described, for example, in Inorg. Chem. 40, 1704-1711, and the like.

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

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

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

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

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

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

  Representative examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl; N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminophenyl) phenylmethane; N, N'-diphenyl-N, N ' − (4-methoxyphenyl) -4,4'-diaminobiphenyl; N, N, N ', N'-tetraphenyl-4,4'-diaminodiphenyl ether; 4,4'-bis (diphenylamino) quadriphenyl; N, N, N-tri (p-tolyl) amine; 4- (di-p-tolylamino) -4 '-[4- (di-p-tolylamino) styryl] stilbene; 4-N, N-diphenylamino- (2-diphenylvinyl) benzene; 3-methoxy-4'-N, N-diphenylaminostilbenzene; N-phenylcarbazole, as well as two of those described in US Pat. No. 5,061,569 Having a condensed aromatic ring in the molecule, for example, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), JP-A-4-308 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) and the like.

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

  The hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can. Although there is no restriction | limiting in particular about the film thickness of a positive hole transport layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5-200 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 as a single layer or a plurality of layers.

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

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

  The electron transport layer can be formed by thinning the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. Although there is no restriction | limiting in particular about the film thickness of an electron carrying layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5-200 nm. The electron transport layer may have a single layer structure composed of one or more of the above materials.

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

  The substrate (hereinafter also referred to as a substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention is not particularly limited in the type of glass, plastic, etc. Although there is no restriction | limiting in particular, As a board | substrate used preferably, glass, quartz, and a transparent resin film can be mentioned, for example. A particularly preferable substrate is a resin film that can give flexibility to the organic EL element.

  Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), and cellulose. Examples include films made of triacetate (TAC), cellulose acetate propionate (CAP), and the like. On the surface of the resin film, an inorganic film, an organic film, or a hybrid film of both may be formed.

  The external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 5% or more. Here, the external extraction quantum efficiency (%) = the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element × 100.

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

<< Method for producing organic EL element >>
As an example of the method for producing the organic EL device of the present invention, a method for producing an organic EL device comprising an anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode will be described.

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

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

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

  The multicolor display device of the present invention is provided with a shadow mask only at the time of forming a light emitting layer, and the other layers are common, so patterning such as a shadow mask is unnecessary, and a vapor deposition method, a casting method, a spin coating method, an ink jet method on one side. A film can be formed by 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.

  In addition, it is also possible to reverse the production order and produce the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode in this order. When a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode. An alternating voltage may be applied. The alternating current waveform to be applied may be arbitrary.

  The display device of the present invention can be used as a display device, a display, and various light emission sources. In a display device or 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 the display include a television, a personal computer, a mobile device, an AV device, a character broadcast display, and an information display in a car. In particular, it may be used as a display device for reproducing still images and moving images, and the driving method when used as a display device for reproducing moving images may be either a simple matrix (passive matrix) method or an active matrix method.

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

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

  The organic EL element of the present invention may be used as one kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a device (display). When used as a display device for reproducing moving images, the driving method may be either a simple matrix (passive matrix) method or an active matrix method. Alternatively, a full-color display device can be manufactured by using three or more organic EL elements of the present invention having different emission colors. Alternatively, it is possible to make a single color emission color, for example, white emission, into BGR using a color filter to achieve full color. Further, it is possible to convert the emission color of the organic EL to another color by using a color conversion filter, and in this case, λmax of the organic EL emission is preferably 480 nm or less.

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

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

  The display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.

  The control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of the plurality of pixels based on image information from the outside. The pixels for each scanning line are converted into image data signals by the scanning signal. In response to this, light is sequentially emitted and image scanning is performed to display image information on the display unit A.

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

  The display unit A includes a wiring unit including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3 and the like on a substrate. The main members of the display unit A will be described below. FIG. 2 shows a case where the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).

  The scanning lines 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at orthogonal positions (details are shown in FIG. Not shown).

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

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

  FIG. 3 is a schematic diagram of a pixel.

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

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

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

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

  That is, the light emission of the organic EL element 10 is performed by providing the switching transistor 11 and the drive transistor 12 which are active elements with respect to the organic EL element 10 of each of the plurality of pixels. 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 diagram of a passive matrix display device. In FIG. 4, a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.

  When the scanning signal of the scanning line 5 is applied by sequential scanning, the pixels 3 connected to the applied scanning line 5 emit light according to the image data signal. In the passive matrix system, the pixel 3 has no active element, and the manufacturing cost can be reduced.

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

  In addition, 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 electroluminescent 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 electroluminescent element 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.

  There is no restriction | limiting in particular as a luminescent material used for a light emitting layer, For example, if it is a backlight in a liquid crystal display element, the platinum complex which concerns on this invention so that it may correspond to the wavelength range corresponding to CF (color filter) characteristic, Any one of known luminescent materials may be selected and combined to whiten.

  As described above, the light-emitting organic EL device of the present invention that emits white light is used 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. Further, it is also useful for display devices such as backlights for liquid crystal display devices.

  In addition, 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.

Example 1
<< Production of Organic EL Element 1-1 >>
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. Then, it 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 deposition apparatus, while α-NPD, CBP, Ir-12, BCP, and Alq 3 are placed in five tantalum resistance heating boats, respectively, and vacuum deposition is performed. It attached to the apparatus (1st vacuum chamber).

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

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

Subsequently, the heating boat containing BCP was energized and heated to provide a hole blocking layer having a thickness of 10 nm at a deposition rate of 0.1 to 0.2 nm / second. 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 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 depressurizing the second vacuum tank to 2 × 10 −4 Pa, a cathode buffer layer having a film thickness of 0.5 nm was provided at a deposition rate of 0.01 to 0.02 nm / second by energizing a boat containing lithium fluoride. Next, a boat containing aluminum was energized, a cathode having a film thickness of 150 nm was attached at a deposition rate of 1 to 2 nm / second, and an organic EL device 1-1 was produced.

<< Production of Organic EL Elements 1-2 to 1-20 >>
In preparation of said organic EL element 1-1, except having changed the light emission dopant, the light emission host, and the hole blocking material as shown in Table 1, it produced similarly, and produced the organic EL elements 1-2 to 1-20. did.

  The obtained organic EL elements 1-1 to 1-20 were evaluated as follows.

<< External quantum efficiency >>
The organic EL elements 1-1 to 1-20 are turned on 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 1-1 was set to 100.

<Luminescent life>
At room temperature the organic EL element 1-1 to 1-20, the continuous lighting by constant current condition of 2.5 mA / cm 2, the time required to becomes half of the initial luminance (τ 1/2) It was measured. Moreover, the light emission lifetime was represented by the relative value when the organic EL element 1-1 was set 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 lifetime than the comparative organic EL device.

  A carboline derivative or a derivative having a ring structure in which at least one carbon atom of a hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom is used in combination in the light-emitting layer. By using 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 in the hole blocking layer, the effects described in the present invention can be further improved. An improvement was seen.

Example 2
<Production of full-color display device>
(Production of blue light emitting element)
The organic EL element 1-6 of Example 1 was used as a blue light emitting element.

(Production of green light emitting element)
In the organic EL element 1-6 of Example 1, Ir-1 was used as a green light emitting dopant to obtain a green light emitting element.

(Production of red light emitting element)
In the organic EL element 1-6 of Example 1, Ir-9 was used as a red light emitting dopant to obtain 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 way, a full color display device was produced by appropriately juxtaposing the red, green, and blue pixels.

  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 3
<Production of full-color display device>
A full-color display device was produced in the same manner as in Example 2 except that the organic EL element 1-6 was changed to the organic EL element 1-8 in the production of 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 4
<Production of full-color display device>
A full-color display device was produced in the same manner as in Example 2 except that the organic EL element 1-6 was changed to the organic EL element 1-13 in the production of 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 5
<Production of full-color display device>
A full-color display device was produced in the same manner as in Example 2 except that the organic EL element 1-6 was changed to the organic EL element 1-14 in the production of 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
<< Preparation of white light emitting element and white lighting device >>
The electrode of the transparent electrode substrate of Example 1 was patterned to 20 mm × 20 mm, and α-NPD was formed as a hole injection / transport layer with a thickness of 25 nm thereon as in Example 1, and further, CBP The heated boat, the boat containing the compound 44 of the present invention, and the boat containing Ir-9 were energized independently, respectively. The vapor deposition rate was adjusted to 100: 5: 0.6, vapor deposition was performed to a thickness of 30 nm, and a light emitting layer was provided.

Next, 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 a lighting device. 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 is a schematic view of the lighting device, and FIG. 6 is a cross-sectional view of the lighting device. The organic EL element 101 was covered with a glass cover 102. 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.

Example 7
<< Preparation of white light emitting element and white lighting device >>
A white lighting device was produced in the same manner as in Example 6 except that the compound 44 of the present invention was changed to 47 in the production of the white light emitting device of Example 6.

  When this lighting device was energized, almost white light was obtained, and it was found that the lighting device can be used.

Example 8
<< Preparation of white light emitting element and white lighting device >>
A white lighting device was produced in the same manner as in Example 6 except that the compound 44 of the present invention was changed to 49 in the production of the white light emitting device of Example 6.

  When this lighting device was energized, almost white light was obtained, and it was found that the lighting device can be used.

Example 9
<< Preparation of white light emitting element and white illumination device by coating method >>
An anode of indium tin oxide (ITO, indium / tin = 95/5 molar ratio) was formed on a glass support substrate of 25 mm × 25 mm × 0.5 mm by a sputtering method using a direct current power (thickness: 200 nm). The surface resistance of this anode was 10Ω / □. Polyvinylcarbazole (hole transporting binder polymer) / compound 44 of the present invention (blue light-emitting orthometalated complex) / tris (2-phenylpyridine) iridium complex (green light-emitting orthometalated complex: Ir -1) / bis (2-benzothiophene [b] -2-yl-pyridine) acetylacetona-toiridium complex (red luminescent orthometalated complex: Ir-9) / 2- (4-biphenylyl) -5 -(4-t-Butylphenyl) -1,3,4-oxadiazol (electron transport material) = 200/2/5/2/50 (mass ratio) dissolved dichloroethane solution was applied with a spin coater As a result, a 100 nm light emitting layer was obtained. A patterned mask (a mask with a light emitting area of 5 mm × 5 mm) is placed on the organic compound layer, and 0.5 nm of lithium fluoride is deposited as a cathode buffer layer and 150 nm of aluminum is deposited as a cathode in a deposition apparatus. A cathode was provided. Aluminum lead wires were respectively emitted from the anode and the cathode to produce a light emitting device. The device was placed in a glove box substituted with nitrogen gas, and sealed with a glass sealing container using an ultraviolet curable adhesive (XNR5493 manufactured by Nagase Ciba) to produce a lighting device.

  When this lighting device was energized, almost white light was obtained, and it was found that the lighting device can be used.

Example 10
<< Preparation of white light emitting element and white illumination device by coating method >>
A white lighting device was produced in the same manner as in Example 9 except that the compound 44 of the present invention was changed to 53 in the production of the white light emitting device of Example 9.

  When this lighting device was energized, almost white light was obtained, and it was found that the lighting device can be used.

Example 11
<< Preparation of white light emitting element and white illumination device by coating method >>
A white lighting device was produced in the same manner as in Example 9 except that the compound 44 of the present invention was changed to 118 in the production of the white light emitting device of Example 9.

  When this lighting device was energized, almost white light was obtained, and it was found that the lighting device can be used.

Example 12
<< Preparation of white light emitting element and white illumination device by coating method >>
An anode of indium tin oxide (ITO, indium / tin = 95/5 molar ratio) was formed on a glass support substrate of 25 mm × 25 mm × 0.5 mm by a sputtering method using a direct current power (thickness: 200 nm). The surface resistance of this anode was 10Ω / □. Polyvinylcarbazole (hole transportable binder polymer) / ACZ1 (hole transport control material) / compound 57 (blue light emitting orthometalated complex) / tris (2-phenylpyridine) iridium complex ( Green light emitting orthometalated complex: Ir-1) / bis (2-benzothiophene [b] -2-yl-pyridine) acetylacetona-toiridium complex (red light emitting orthometalated complex: Ir-9) / 2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazol (electron transport material) = 150/50/2/5/2/50 (mass ratio) The dissolved dichloroethane solution was applied with a spin coater to obtain a 100 nm light emitting layer. A patterned mask (a mask with a light emitting area of 5 mm × 5 mm) is placed on the organic compound layer, and 0.5 nm of lithium fluoride is deposited as a cathode buffer layer and 150 nm of aluminum is deposited as a cathode in a deposition apparatus. A cathode was provided. Aluminum lead wires were emitted from the anode and cathode, respectively, to produce a light emitting device. The device was placed in a glove box substituted with nitrogen gas, and sealed with a glass sealing container using an ultraviolet curable adhesive (XNR5493 manufactured by Nagase Ciba) to produce a lighting device.

  When this lighting device was energized, almost white light was obtained, and it was found that the lighting device can be used.

Example 13
<< Preparation of white light emitting element and white lighting device >>
A white lighting device was produced in the same manner as in Example 12 except that the compound 57 of the present invention was changed to 61 in the production of the white light emitting device of Example 12.

  When this lighting device was energized, almost white light was obtained, and it was found that the lighting device can be used.

Example 14
<< Preparation of white light emitting element and white lighting device >>
A white lighting device was produced in the same manner as in Example 12 except that the hole transport control material ACZ1 was changed to ACZ2 in the production of the white light emitting device of Example 12.

  When this lighting device was energized, almost white light was obtained, and it was found that the lighting device can be used.

Example 15
<< Production of Organic EL Elements 2-1 to 2-13 >>
In the same manner as in Example 1 except that the light emitting dopant was changed to Ir-1 and the hole blocking material was changed as shown in Table 2 in the organic EL element 1-1 of Example 1. Organic EL elements 2-1 to 2-13 were produced.

  Measurement of the external extraction quantum efficiency and emission lifetime of each of the obtained devices was performed in the same manner as described in Example 1.

  At this time, the value of the organic EL element 2-1 was set to 100, and the value of each organic EL element sample was expressed as a 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 organic EL element. The emission color of the organic EL element of the present invention was all green.

Claims (5)

  1. An organic electroluminescent element material, which is an ortho metal complex represented by the following general formula (5) or (6).
    (In the formula, M represents iridium, platinum, palladium, or osmium . M1 is 1 or 2, and n1 is 1 or 2. However, m1 + n1 is 2 or 3, which corresponds to the charge of M. X 11 represents a carbon atom or a nitrogen atom, Q 11 is .X 12 that represents an atomic group for forming a ring a is an aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocyclic 6-membered together with carbon atoms and X 11 represents a carbon atom or a nitrogen atom, Q 12 is .X 1 representing an atom group forming a ring B is an aromatic heterocyclic 5-6 membered together with the nitrogen atom and X 12 is O, S, CH 2, CHR , CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO 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 Represents.
    X 21 represents a carbon atom or a nitrogen atom, and Q 21 represents an atomic group forming a ring C which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocycle together with the carbon atom and X 21 . X 22 represents a carbon atom or a nitrogen atom, and Q 22 represents an atomic group that forms a ring D that is a 5- or 6-membered aromatic heterocyclic ring together with the nitrogen atom and X 22 . X 2 represents O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO 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. However, ring A and ring C, ring B and ring D are not the same at the same time. )
    (In the formula, M represents iridium, platinum, palladium, or osmium . M2 is 1 or 2, and n2 is 1 or 2. However, m2 + n2 is 2 or 3, which corresponds to the charge of M. X 11 represents a carbon atom or a nitrogen atom, Q 11 is .X 12 that represents an atomic group for forming a ring a is an aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocyclic 6-membered together with carbon atoms and X 11 represents a carbon atom or a nitrogen atom, Q 12 is .X 1 representing an atom group forming a ring B is an aromatic heterocyclic 5-6 membered together with the nitrogen atom and X 12 is O, S, CH 2, CHR , CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO 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 X 31 , X 32 represents a nitrogen atom or a phosphorus atom, and X 3 is represented by the following formulas (4-10), (4-11), (4-18), (4-20) according to X 31 -X 3 -X 32 , (It represents an atomic group forming a bidentate ligand having the partial structure represented by (4-21) or (4-22) or a tautomer thereof as a partial structure.)
    (Wherein R 82 , R 86 and R 87 represent a hydrogen atom or a substituent, n 81 represents an integer of 0 to 3, and n 83 represents an integer of 0 to 2. R 84 , R 85 , R 88 and R 89 represent an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group, R 88 and R 89 may be an aryloxy group, Q 81 is 5 together with carbon and nitrogen. It represents an atomic group forming an aromatic heterocyclic ring 6-membered, Q 82 represents an atomic group forming an aromatic heterocyclic ring of 5-membered carbon, together with the nitrogen.)
  2. The organic electroluminescent element material according to claim 1, which is an ortho metal complex having a partial structure represented by the following general formula (10) or a tautomer thereof as a partial structure.
    (In the formula, M represents iridium, platinum, palladium or osmium . X 61 , X 62 , X 63 and X 64 each represents a carbon atom or a nitrogen atom, and Q 61 represents a carbon atom and X 61 and X 63 together. It represents an aromatic hydrocarbon ring or an atomic group forming a ring F is a 5-6 membered aromatic heterocyclic 6-membered, Q 62 is an aromatic heterocyclic 5-6 membered together with the nitrogen atom and X 62, X 64 .X b, X c table to a substituent van der Waals volume is 20 Å 3 or more .m6 representing an atom group forming a ring G is a ring, the n6 represents 0 or 1. However, m6 + n6 ≧ 1 X 6 represents O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C═O, C═NR, SO or SO 2. R represents an alkyl group, a cycloalkyl group, an alkenyl Group, aryl group, heterocycle Or an aromatic heterocyclic group.)
  3. The following general formulas (1-19), (1-76), (1-82), (1-86), (1-112), (1-121), (1-124), (1-127) , (1-130), (2-29), (2-38), (2-41), (2-43), (2-44), (3-2), (3-6), ( The organic electroluminescent device material according to claim 1, which is an orthometal complex having a partial structure represented by 3-8) or (3-9) or a tautomer thereof as a partial structure.
    (In the formula, M represents iridium, platinum, palladium or osmium. R 11 , R 12 , R 21 , R 22 , R 31 And R 32 Each represents a substituent. Multiple R 32 May form a ring. n11, n12, n21, n22, n31 and n32 each represents an integer selected from 0 to 2. X 14 > N-R 13 , -O- or -S-. R 13 Represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X 15 , X 16 , X 17 , X 24 And X 32 Are each> N-R 16 ,> N-R 24 ,> N-R 34 , -O- or -S-. X 32 Is> SO 2 It may be. R 16 , R 24 And R 34 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 0 Is O, S, CH 2 , CHR, CR 2 , NR, PR, SiR 2 , C = O, C = NR, SO or SO 2 Represents. R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. )
  4. M is iridium or platinum, The organic electroluminescent element material as described in any one of Claims 1-3 characterized by the above-mentioned.
  5.   An organic electroluminescent element comprising the organic electroluminescent element material according to any one of claims 1 to 4.
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