WO2006098120A1 - Organic electroluminescent device material and organic electroluminescent device - Google Patents

Organic electroluminescent device material and organic electroluminescent device Download PDF

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WO2006098120A1
WO2006098120A1 PCT/JP2006/303110 JP2006303110W WO2006098120A1 WO 2006098120 A1 WO2006098120 A1 WO 2006098120A1 JP 2006303110 W JP2006303110 W JP 2006303110W WO 2006098120 A1 WO2006098120 A1 WO 2006098120A1
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group
represents
ring
general formula
aromatic heterocyclic
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PCT/JP2006/303110
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French (fr)
Japanese (ja)
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Masato Nishizeki
Tomohiro Oshiyama
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Konica Minolta Holdings, Inc.
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Abstract

Disclosed is an organic EL device material exhibiting high luminous efficiency while having long emission life. Also disclosed are an organic EL device, an illuminating device, and a display. Specifically disclosed is an organic EL device material characterized by being composed of an orthometal complex represented by the following general formula (1). MLmL'n (1) (In the formula, M represents a group 8-10 metal element of the periodic table; L and L' respectively represent a bidentate ligand different from each other; m represents 1 or 2; and n represents 1 or 2. In this connection, m + n is 2 or 3 and equal to the electric charge of M. The partial structure ML is represented by the general formula (2) below, and the partial structure ML' is represented by the general formula (3) or (4) below.)

Description

Specification

Organic elect port luminescent device material, an organic-elect opening ELEMENT Technical Field

[0001] The present invention relates to an organic-elect opening luminescent device material, an organic-elect opening luminescent element, a display device and a lighting device.

BACKGROUND

[0002] emissive as an electronic display device, elect port luminescence Display I (hereinafter referred to as ELD) is. The components of the ELD, inorganic elect port Ruminessen scan element and an organic-elect opening element (hereinafter, referred to as organic EL element). Inorganic elect port element has been used as a flat light source, but in order to drive the element requires a high voltage of alternating current. The organic EL element has a sandwich a light emitting layer containing a light emitting compound at the cathode and the anode structure, by injecting electrons and holes into the light emitting layer, generates an exciton by recombination is, the excitons is an element that emits light by utilizing emission (fluorescence 'phosphorescence) of light at the time of deactivation, and can emit light in several V~ several tens V voltage of about, further, a self-luminous rich in viewing angle for certain space-saving because visibility is complete solid device with high device thin film type, it is the perspective et Interesting portability like.

While [0003] is the force, in the organic EL element for future practical use, and development of organic EL element that emits light efficiently high luminance with low power consumption is desired more.

[0004] In Patent No. 3,093,796, organic elect port luminescent device material (hereinafter, referred to as organic EL device material) As a stilbene derivative, a distyryl Rua Lee alkylene derivatives or tris styryl Rua Lee alkylene derivatives, phosphor traces the doped, improving luminous brightness, and achieve a long life of the organic EL element, Ru.

[0005] Furthermore, 8-hydroxyquinoline aluminum complex as Hosutoi 匕合 thereof, an organic EL device having an organic light-emitting layer doped with fluorescent body traces thereto (e.g., JP 63- 264692 discloses), 8 - hydroxyquinoline aluminum complex as a Hosutoi 匕合 thereof, an organic EL device having this organic light-emitting layer doped with Kinatari Don-based dyes (e.g., JP-a-3 255 190 JP), and the like.

[0006] As described above, when using the light-emitting excited singlet force generation ratio of singlet excitons and triplet excitons is 1: generation probability of an emitting exciton species is 3 25%, since the light extraction efficiency is about 20%, the limit of external extraction quantum efficiency (r? ext) had been 5%.

[0007] However, reports of the organic EL element using the phosphorescence also excited triplet force from Princeton (MA Baldo et al., Nature, 395 Certificates, 151- 154 pages (1998)) Since the force, at room temperature in and study of material that exhibits phosphorescence is becoming more active, Ru.

[0008] For example MA Baldo et al., Nature, 403 Certificates, No. 17, 750-753 pages (2000), also disclosed in U.S. Patent No. 6, 097, 147 Pat like.

[0009] With the excited triplet, since the upper limit of the internal quantum efficiency of 100% theoretically becomes luminous efficiency force doubled as compared with the singlet excited, almost the same performance is obtained al a CCFL It has attracted attention as a lighting applications because it is subject.

[0010] For example, S. Lamansky et al., J. Am. Chem. Soc., 123 Certificates, 4304 Page (2

In 001 years) and the like, many compounds are synthetic studied mainly heavy metal complexes such as iridium complexes.

[0011] Moreover, the aforementioned MA Baldo et al, nature, 403 Certificates, No. 17, at 750-753 pages (2000), as a dopant, tris. (2 Hue - Rubirijin) been studied using iridium ing.

[0012] Other, ME Tompson, etc., The 10th International Workshop on In organic and Organic Electroluminescence (EL '00, Hamamatsu) [frozen ヽ Te, de ~ ~ Nono cement as L Ir (acac), for example, (ppy) Ir ( the acac), also, Moon- Jae Youn. 0g, Te

twenty two

tsuo Tsutsui, etc. ί Well, and ί Mari, The 10th International Workshop on Inorga nic and Organic Electroluminescence (EL, 00, Hamamatsu) Te [frozen ヽ, as Dono cement, tris (2- (p- tolyl) pyridine) iridium ( Ir (ptpy)), tris (benzo [h] reluctant

3

Emissions) and examined using an iridium (Ir (bzq)) or the like, Ru (Note these metal complexes are generally

3

It is called ortho-metalated iridium complex, Ru. ).

[0013] In addition, the, S. Lamanskv et al., J. Am. Chem. Soc., 123 Certificates, 4304 pages (2001) Hitoshinio, also, attempts a device is produced using various iridium complexes It is is! / Ru ヽ.

[0014] In order to obtain a high luminous efficiency using, The 10th International Workshop on Inorganic and Organic Electroluminescence (EL '00, Hamamatsu) in, Ikai like a hole transport compound as a host of the phosphorescent I 匕合 product ing. In addition, ME T ompson, etc., various types of electron-transporting material as a host of a phosphorescent 匕合 products, these doped with a new iridium complex! /, Ru.

[0015] Orutometarui 匕錯 body to the central metal was platinum instead of iridium be attention, Ru. Regarding this type of complex, examples which gave characterized ligands are known a number (e.g., Patent Documents 1-5 and Non-Patent Reference 1.) 0

[0016] luminance and luminous efficiency of case where a light emitting element in any case, since the light that light emission derived from phosphorescent, but are intended to be significantly improved compared with the conventional organic EL device, Tsu the emission lifetime of the organic EL elements, Te than the conventional organic EL element low, and, cormorants problems there ivy. Thus, the light emitting material of phosphorescent high efficiency is a current status that not sufficiently achieve the performance improvement in emission life of the short-waved and the organic EL element of the luminescence wavelength can withstand the difficult practical .

[0017] With respect to shorter and shorter wavelengths, to date fluorine atom phenylalanine pyridine, Torifuruoromechi group, introducing an electron withdrawing group such as Shiano group as a substituent, picolinic acid and Birazaboru system coordinating as ligands it is known to introduce a child (e.g., JP. 6 to:. L0 and non-Patent documents 1 to 4 refer) is, these ligands to achieve blue turned into the emission wavelength of the luminescent material short while achieve elements of high efficiency and emission lifetime of the organic EL element to deteriorate significantly, its improvement has been required.

Patent Document 1: JP 2002- 332291 JP

Patent Document 2: JP 2002- 332292 JP

Patent Document 3: JP 2002- 338588 JP

Patent Document 4: JP 2002 - 226495 discloses

Patent Document 5: JP 2002- 234894 JP

Patent Document 6: WO02Zl5645 Patent Document 7: JP 2003- 123982 JP

Patent Document 8: JP 2002- 117978 JP

Patent Document 9: JP 2003 - 146996 discloses

Patent Document 10: WO04Z016711 Pat.

Non-Patent Document 1: Inorganic Chemistry, 41 Certificates, No. 12, 3055-3066 page (2 002 years)

Non-Patent Document 2: Aplied Physics Letters, 79 Certificates, 2082 page (2001) Non-Patent Document 3: Aplied Physics Letters, 83 Certificates, 3818 page (2003) Non-Patent Document 4: New Journal of Chemistry, 26 Certificates, 1171 page (2002) dISCLOSURE oF tHE iNVENTION

Problems that the Invention is to you'll solve

[0018] are those the 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, the organic EL device, a lighting device and a display device it is to provide.

Means for Solving the Problems

[0019] The above object of the present invention can be attained by the following configurations.

The preferred embodiment of the present invention and the present invention are shown below.

[0020] (1) Organic elect port luminescent device material which is a orthometal complex represented by the following general formula (1).

[0021] [Formula 1] general formula (1)

ML m L 'π

[0022] (wherein, Micromax represents 8-10 metal element in the periodic table. L, L 'represents a bidentate ligands different from each other, m is 1 or 2, n is 1 or 2. However, m + n is in agreement with the charge of M is 2 or 3.

Table in [0023] bidentate ligands L, L 'partial structure ML which is coordinated to the metal M is represented by the following general formula (2), the partial structure ML' the following general formula (3) or (4) It is. [0024] [Formula 2]

- general formula (3) - general formula (4)

M严, ..., X 3

's one Roh

[0025] X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X

11 11 11

It represents an atomic group forming a ring A is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X

12 represents a carbon atom or a nitrogen atom, Q

12 is a nitrogen atom and X

It represents an atomic group forming a 12 with a 5-6 membered aromatic heterocyclic ring B. X is 0, S, CH, CHR, CR, NR, P

1 2 2

It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl

twenty two

Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0026] X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X

21 21 21

It represents an atomic group forming a ring C is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X

22 represents a carbon atom or a nitrogen atom, Q to 6

22 is a nitrogen atom and X

It represents an atomic group forming a ring D is 22 with 5-membered aromatic heterocyclic. X is 0, S, CH, CHR, CR, NR, P

2 2 2

It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl

twenty two

Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0027] X, X represents a nitrogen atom or a phosphorus atom, X is coordinated to M through X, the X

31 32 3 31 32

It represents an atomic group forming a bidentate ligand. )

(2) organic-elect opening luminescent device material according to (1), wherein the ortho metal complex represented by the following general formula (5).

[0028] [Formula 3] general formula (5)

[0029] (wherein, M is. Ml representing a 8-10 metal element in the periodic table is 1 or 2, nl is 1 or 2. However, ml + nl is 2 or 3 There match the charge of M. X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X

11 11 11

It represents an atomic group forming a ring A is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X

12 represents a carbon atom or a nitrogen atom, Q

12 is a nitrogen atom and X

It represents an atomic group forming a 12 with a 5-6 membered aromatic heterocyclic ring B. X is 0, S, CH, CHR, CR, NR, P

1 2 2

It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl

twenty two

Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0030] X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X

21 21 21

It represents an atomic group forming a ring C is a family hydrocarbon ring or 5- to 6-membered aromatic heterocycle. X represents a carbon atom or a nitrogen atom, Q is an aromatic 5-6 membered together with the nitrogen atom and X

22 22 22

It represents an atomic group forming a ring D is a family heterocycle. X is 0, S, CH, CHR, CR, NR,

2 2 2

PR, SiR, C = 0, C = NR, represents SO or SO. R is an alkyl group, a cycloalkyl

twenty two

Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. However, ring

A and ring C, ring B and ring D does not become the same as at the same time. )

(3) In Formula (5), one least also among the aromatic heterocyclic ring B, or an aromatic heterocyclic ring D is a 6-membered ring, wherein, wherein the other is a 5-membered ring (2) organic electroluminescent Roh Remy network sense element material according to.

[0031] (4) organic-elect opening luminescent device material according to (1), wherein the ortho metal complex represented by the following general formula (6).

[0032] [Formula 4] - general formula (6)

[0033] (wherein, M is. M @ 2 representing a 8-10 metal element in the periodic table it is 1 or 2, n2 is 1 or 2. However, m @ 2 + n2 is 2 or 3 There match the charge of M. X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X

11 11 11

It represents an atomic group forming a ring A is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X

12 represents a carbon atom or a nitrogen atom, Q

12 is a nitrogen atom and X

It represents an atomic group forming a 12 with a 5-6 membered aromatic heterocyclic ring B. X is 0, S, CH, CHR, CR, NR, P

1 2 2

It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl

twenty two

It represents a group, Ariru group, a heterocyclic group or an aromatic heterocyclic group - group, Aruke. X, X is

31 32 represents a nitrogen atom or a phosphorus atom, X, X

3 X

31 32 via a represents an atomic group forming a bidentate ligand coordinated in the M. )

(5) In the general formula (6), organic elect port luminescent device material according to prior SL (4), wherein the aromatic heterocyclic ring B is a 6-membered ring.

[0034] (6) the following general formula (1 1) to above, wherein the ortho metal complex having a partial structure or partial structure a tautomer thereof represented by the (1 150) (1) - organic elect port luminescent device material according to ヽ not a Re mosquito one of (4).

[0035] [of 5] [9εοο]

Oi-- l

OlieOC / 900Zdf / I3d 8 0Ζϊ860 / 900ί OAV llC0C / 900Zdf / X3d 6 0ΖΪ860 / 900Ζ OAV ]

[6 ^>] [6C00]

V

Les

llC0 £ / 900Zdf / X3d 0Π860 / 900Ζ OAV

1] 2]

]

]

(Wherein, M represents a Group 8 to 10 metal elements in the periodic table. R, R each location

11 12

Represents substituent, nl l, nl2 represents an integer, each selected from 0 to 2. X, X are each> N

13 14

-R, represents -O- or -S-. R is an alkyl group, a cycloalkyl group, an alkenyl

13 13

Group, a Ariru group, a heterocyclic group or an aromatic heterocyclic group. X, X, X, X, respectively

15 16 17 18

> Represents NR, -O- or -S-. R is a hydrogen atom, an alkyl group, a cycloalkyl

16 16

It represents a group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. X, X, X each represent CH or N, any one or two N. X is 0, S, C b 19c 0

It represents H, CHR, CR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is

2 2 2 2

Kill group, a cycloalkyl group, Aruke - represents a group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. )

(7) the following general formula (2 1) to above, wherein the ortho metal complex having a partial structure or partial structure a tautomer thereof represented by (2 50) (1) - ( organic elect port luminescent device material according to the 5), not a Re mosquitoes (1).

[0046] [of 15]

[0047] [of 16]

[Ζΐ ^] [8W) 0]

OllCOC / 900Zdf / X3d 61 · 0ΖΪ860 / 900Ζ OAV -21 <R 2,> n2, x «" 22 (R 21) N2, 2- 23 (R 21> N2, X

,

Ν ''

(2) π:

]

]

(Wherein, M represents a Group 8 to 10 metal elements in the periodic table. R, R each location

Represents 21 22 substituent, n21, n22 is an integer selected from 0-2. X is,> N- R, - O-

23 represents the 23 or S. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru

twenty three

Group, a heterocyclic group or an aromatic heterocyclic group. X, X is,> NR, -O or

24 25 24

It represents the S. R is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, § Li

twenty four

Lumpur group, a heterocyclic group or an aromatic heterocyclic group. X, X, X are each CH or N

26 27 28

The stands, any one or two are N. X is 0, S, CH, CHR, CR, NR, PR,

0 2 2

SiR, represent a C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl group,

twenty two

An alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. )

(8) the following general formula (3-1) - above, wherein the ortho metal complex having a partial structure or a tautomer thereof represented by (3-10) as a partial structure (1) - ( organic elect port luminescent device material according to ヽ not a Re mosquito one of 5). [0052] [of 20]

[0053] (wherein, M represents a Group 8 to 10 metal elements in the periodic table. R, R each location

Represents 31 32 substituent, n31, n32 is an integer selected from 0-2. X is,> N- R, - O-

31 represents the 33 or S. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru

33

Group, a heterocyclic group or an aromatic heterocyclic group. X, X is,> NR, -O or

32 33 34

It represents the S. R is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, § Li

34

Lumpur group, a heterocyclic group or an aromatic heterocyclic group. X, X, X are each CH or N

34 35 36

The stands, any one or two are N. X is 0, S, CH, CHR, CR, NR, PR,

0 2 2

SiR, represent a C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl group,

twenty two

An alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. )

(9) above, wherein the ortho metal complex having a partial structure or a tautomer thereof represented by the following general formula (7) as a partial structure (1) to (5), (8), organic elect port luminescent device material according to item 1 Zureka. [0054] [of 21] the general formula "7)

[0055] (wherein, M represents a Group 8 to 10 metal element of the periodic table. X is or carbon atoms

41

The other represents a nitrogen atom, Q 6-membered

41 carbon atoms and X

Aromatic with 41 hydrocarbon ring or

It represents an atomic group forming a ring E is a 5- to 6-membered aromatic heterocycle. R represents a substituent, n

41

4 is an integer selected from 0-3. Xa is - N (Ra), - display the S- Ra - O-Ra or

2

It is. Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, the heterocyclic group or aromatic heterocyclic group. Xa is - N (Ra), the two Ra different even with the same

2

One is or may be. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S

4 2 2 2

It represents O or SO. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group

2

, A heterocyclic group or an aromatic heterocyclic group. )

(10) the following general formula (8) or organic Jer Tatoro described above, wherein the ortho metal complex (9) having a partial structure or partial structure a tautomer thereof represented by (9) luminescent element material.

[0056] [of 22]

[0057] (wherein, M represents a Group 8 to 10 metal elements in the periodic table. R, R, R, R each represents a hydrogen atom or an electron donating substituent, at least one is an electron donating substituent. R, R, R, R

56 57 58 59 each represents a hydrogen atom or a substituent, R, R

56 At least one 58 is an electron-withdrawing group. R, R represents a substituent, n51, n5

50 55

2 is an integer selected from 0-3. Xa is - N (Ra), - display the S- Ra - O-Ra or

2

It is. Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, the heterocyclic group or aromatic heterocyclic group. Xa is - N (Ra), the two Ra different even with the same

2

One is or may be. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S

5 2 2 2

It represents O or SO. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group

2

, A heterocyclic group or an aromatic heterocyclic group. )

(11) any one of said, characterized in that the partial structure or a tautomer thereof represented by the following general formula (10) is ortho metal complex having as a partial structure (1) - (10) organic elect port luminescent device material according to.

[0058] [of 23]

[0059] (wherein, M represents a Group 8 to 10 metal elements in the periodic table. X, X, X, X

61 62 63 64 each represent a carbon atom or a nitrogen atom, Q

61 carbon atoms and X, X

61 63 with Represents an atom group forming a ring F is a 6-membered aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocycle, Q is a nitrogen atom and X, aromatic 5-6 membered with X to form a ring G is heterocyclic

62 62 64

It represents a group of atoms that. X, X represents a substituent van der Waals volume is 20 A 3 or more bc

. m6, n6 represents 0 or 1. However, it is m6 + n6≥l. X is 0, S, CH, CHR,

6 2

It represents CR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a consequent

2 2 2

Mouth alkyl group, an alkenyl group, an Ariru group, a heterocyclic group or an aromatic heterocyclic group. ) (12) Organic E according to the following general formula (11) - (wherein, wherein the ortho metal complex having a partial structure or partial structure a tautomer thereof represented by 14) (10) Direct opening luminescent element material.

[Of 24]

Formula (13) - general formula (14)

7

(Wherein, M represents a Group 8 to 10 metal elements in the periodic table. X, X, X, X

71 72 73 74 each represent a carbon atom or a nitrogen atom, Q

71 carbon atoms, X, X

71 73 with represents an atomic group forming a ring H is Kaoru aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocyclic 6-membered, Q is a nitrogen atom, X, aromatic 5-6 membered with X atoms forming the ring K is a heterocyclic

72 72 74

Representing the group. Q

73 represents an atomic group forming an aromatic hydrocarbon ring or aromatic heterocyclic ring with the carbon atoms. Q

74 represents an atomic group forming an aromatic heterocyclic ring together with the nitrogen atom. X

7

0 represents S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, SO or SO.

2 2 2 2

R represents an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, a heterocyclic group, or Kaoru aromatic heterocyclic group. )

Bidentate formed by X- X - (13) X in the general formula (4) or the general formula (6)

31 3 32

The ligand is characterized by having the following general formula (4 1) to a partial structure represented by (4 31), or or a tautomer thereof as a partial structure (1), (4) - (12) organic elect port luminescent device material according to any one of.

[0062] [of 25]

4-1 4-2 4-3

, - - «¾ 2, Q'8'2 ,, - <¾ '2

[0063] [of 26] 4-20 4-21 4-22 4-23

[0064] (wherein, R represents R -CO- or R -SO-, R represents an alkyl group, a cycloalkyl

81 80 80 2 80

It represents a group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. R, R, R, R

82 83 86 87 represents the location substituent, n represents an integer of 0 to 3, n, n represents an integer of 0 to 2. R, R, R,

81 82 83 84 85 88

R is an alkyl group, a cycloalkyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group

89

A representative. Q represents an atomic group forming an aromatic heterocyclic 5-6 membered carbon, together with the nitrogen,

81

Q, Q represents an atomic group forming an aromatic heterocyclic ring of 5-membered carbon, together with the nitrogen. )

82 83

(14) above, wherein the a M force iridium or platinum (1) or to (13)

Organic elect port luminescent device material according to item 1.

[0065] (15) wherein (1) to (14)!, Organic elect port luminescent element characterized by containing the organic-elect opening luminescent element materials according to item 1 Zureka.

[0066] (16) a light-emitting layer as a constituent layer, wherein the light-emitting layer contains an organic-elect opening luminescent device material of the mounting serial to any force one of said (1) to (14) organic-elect Lono Remy network sense element.

[0067] (17) has a hole blocking layer as a constituent layer, that the hole blocking layer contains the organic elect port luminescent device material according to any force one of said (1) to (14) organic elect port luminescent element characterized.

[0068] (18) above, wherein by containing a compound represented by the following general formula (1 A) (15) ~

Organic elect port device as claimed in any forces one of (17).

[0069] [of 27]

- general formula (1A}

',' ---- z 3 - - -c, 1

[0070] (Table wherein, Z is an aromatic heterocyclic ring, Z is an aromatic heterocyclic ring or an aromatic hydrocarbon ring

1 2

And, Z represents a divalent linking group or a single bond. Table a hydrogen atom or a substituent R

3 101

It is. )

(19) above, wherein the Z of the compound represented by the general formula (1 A) is a 6-membered ring

1

Organic elect port device as described in (18).

[0071] (20) above, wherein the Z of the compound represented by the general formula (1A) is a 6-membered ring

2

Organic elect port device as described in (18) or (19).

[0072] (21) before the Z of the compound represented by the general formula (1A) is characterized in that a bond

3

Serial (18) to (20) of?, Organic elect port device as claimed in shift force (1).

[0073] (22) wherein the compound represented by the general formula (1A) is you characterized by a molecular weight of 450 or more (18) to (21), organic elect port luminescence according to the deviation force 1 wherein element.

[0074] (23) wherein the compound represented by the general formula (1A) is characterized by being represented by the following general formula (1 A- 1) of (18) to (22), Zureka first term organic elect port device as described in.

[0075] [of 28] general formula (1A- 1>

[0076] (wherein, R to R each independently represent a hydrogen atom or a substituent.)

501 507

(24) the said compound represented by the general formula (1A) is characterized by being represented by the following general formula (1 A- 2) of (18) to (22), according to item 1 Zureka organic-elect opening luminescence element.

[0077] [of 29]

- general formula (1A- 2>

[0078] (wherein, R to R each independently represent a hydrogen atom or a substituent.)

511 517

(25) the said compound represented by the general formula (1A) is characterized by being represented by the following general formula (1 A- 3) of (18) to (22), according to item 1 Zureka organic-elect opening luminescence element.

[0079] [Formula 30] Formula (1A - 3)

(Wherein, R to R each independently represent a hydrogen atom or a substituent.)

521 527

(26) wherein the compound represented by the general formula (1A) is characterized by being represented by the following general formula (1A - 4) (18) to (22), according to item 1 Zureka organic elect opening luminescence element.

[0081] [of 31] the general formula (1A_4>

[0082] (wherein, R to R each independently represent a hydrogen atom or a substituent.)

531 537

(27) the said compound represented by the general formula (1A) is characterized by being represented by the following general formula (1 A- 5) of (18) to (22), according to item 1 Zureka organic-elect opening luminescence element.

[0083] [of 32]

- general formula (1A- S)

[0084] (wherein, R to R each independently represent a hydrogen atom or a substituent.)

541 548

(28) the said compound represented by the general formula (1A) is characterized by being represented by the following general formula (1 A- 6) (18) to (22), according to item 1 Zureka organic-elect opening luminescence element.

[0085] [Formula 33] Formula ΠΑ- 6}

Table in [0086] (wherein, R to R each independently represent a hydrogen atom or a substituent.) (29) The compound represented by the general formula (1 A) is represented by the following general formula (1 A- 7) said it characterized in that the (18) to (22), an organic-elect opening device as described in item 1 Zureka.

[0087] [Formula 34] Formula "1A_7)

[0088] (wherein, R to R each independently represent a hydrogen atom or a substituent.)

561 567

(30) the said compound represented by the general formula (1A) is characterized by being represented by the following general formula (1 A- 8) of (18) to (22), according to item 1 Zureka organic-elect opening luminescence element.

[0089] [of 35]

- general formula <1A_8)

[0090] (wherein, R to R each independently represent a hydrogen atom or a substituent.)

571 577

(31) the said compound represented by the general formula (1A) is characterized by being represented by the following general formula (1 A- 9) of (18) to (22), according to item 1 Zureka organic-elect opening luminescence element.

[0091] [Formula 36] - general formula (1A-9)

[0092] (wherein, R represents a hydrogen atom or a substituent. A plurality of R may be different from one each Yogu be the same.)

(32) The compound represented by the general formula (1A) of the characterized by being represented by the following general formula (1 A- 10) (18) ~ (22), according to the deviation force 1 wherein organic-elect opening luminescence element.

[0093] [of 37]

- general formula (1A_10>

[0094] (wherein, R represents a hydrogen atom or a substituent. A plurality of R may be different from one each Yogu be the same.)

(33) wherein the compound represented by the general formula (1A) is characterized by having at least one group represented by any one of the following general formula (2A- 1) ~ (2A- 10) (18 ) organic elect port device as claimed in any one of - (22).

[0095] Formula 38] - general formula (2A- 1) - general formula (2A- 2>

(Wherein, R ~R, R ~R, R ~R, R ~R, R ~ R, R ~R, R

502 507 512 517 522 527 532 537 552

~R, R ~R, R ~R, the R to R each independently represent a hydrogen atom or a substituent table

567 572 577 582 588 592 598

And, the substituents may be each have Yogu be the same or different. )

(34) The organic elect port according to any one of the compounds represented by the general formula (1 A) is characterized by being represented by the following general formula (3A) (18) ~ (22) luminescence element. [0097] [of 39]

General formula (3A)

[0098] (wherein, R to R to R

601 606 force each independently represent a hydrogen atom or a substituent R

601 least one 606 represents at least one group selected group forces represented by the general formula (2 1) - (2-10). )

(35) wherein the compound represented by the general formula (1 A) is characterized by being represented by the following general formula (4A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

[0099] [of 40]

'General formula (4A)

[0100] (wherein, R to R are the force R to R representing each independently a hydrogen atom or a substituent low

One 611 620 611 620 Kutomo represents at least one group selected from the group represented by the general formula (2A- 1) ~ (2A- 10). )

(36) wherein the compound represented by the general formula (1A) is characterized by being represented by the following general formula (5A) of (18) to (22), an organic elect port according to item 1 Zureka luminescence element.

[0101] [Formula 41] Formula (5A)

N person N

π person who '

[0102] (wherein, represented by R to R are each least one of the force R to R independently represent a hydrogen atom or a substituent Formula (2A- 1) ~ (2A- 10) It represents at least one group selected from the group.)

(37) wherein the compound represented by the general formula (1 A) is characterized by being represented by the following general formula (6A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

Formula 42] Formula (6A)

[0104] (In the formula, R

631~R

645 force each independently represent a hydrogen atom or a substituent R

631~R

Least one 645 represents at least one group selected from the group represented by the general formula (2A- 1) ~ (2A- 10). )

(38) wherein the compound represented by the general formula (1 A) is characterized by being represented by the following general formula (7A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

[0105] [Formula 43] Formula (7A)

[0106] (wherein, R to R are the force R to R representing each independently a hydrogen atom or a substituent low

One 651 656 651 656 Kutomo represents at least one group selected group forces represented by the general formula (2 1) - (2-10). na represents an integer of 0 to 5, nb represents an integer of 1-6, the sum of na and nb is 6. )

(39) wherein the compound represented by the general formula (1 A) is characterized by being represented by the following general formula (8A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

[Of 44] the general formula <8AJ

[0108] (wherein, R to R are the force R to R representing each independently a hydrogen atom or a substituent low

One 661 672 661 672 Kutomo represents at least one group selected from the group represented by the general formula (2A- 1) ~ (2A- 10). )

(40) wherein the compound represented by the general formula (1 A) is characterized by being represented by the following general formula (9A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

[0109] [Formula 45] Formula (9A)

Kutomo one represents at least one group selected group forces represented by the general formula (2A- 1) ~ (2A- 10). ) (41) wherein the compound represented by the general formula (1A) is to feature to be represented by the following general formula (10A) of (18) to (22), according to item 1 Zureka organic elect opening luminescence element.

[0111] [Formula 46] Formula (10A>

[0112] (wherein, represents a R to R each independently represent a hydrogen atom or a substituent, L is a divalent linking group

691 700 1

A representative. At least one of R to R is represented by the general formula (2A- 1) ~ (2A- 10)

691 700

Motokakara represents at least one group selected. )

(42) wherein the compound represented by the general formula (1 A) is a feature to be represented by the following general formula (11 A) of (18) to (22), according to item 1 Zureka organic-elect opening luminescence element.

[0113] [Formula 47] general formula (11 A)

[0114] (wherein, R, R each independently represents a hydrogen atom or a substituent. N, m are each 1 to 2 integer

1 2

It represents the number, k, 1 each represents 3-4 integer. However, n + k = 5, and a l + m = 5. )

(43) wherein the compound represented by the general formula (1A) is to feature to be represented by the following general formula (12A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

[0115] [Formula 48] - general formula (12A)

[0116] (wherein, R, R each independently represents a hydrogen atom or a substituent. N, m are each 1 to 2 integer

1 2

It represents the number, k, 1 each represents 3-4 integer. However, n + k = 5, and a l + m = 5. )

(44) wherein the compound represented by the general formula (1A) is to feature to be represented by the following general formula (13A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

[0117] [Formula 49] Formula (13A)

[0118] (wherein, R, R each independently represents a hydrogen atom or a substituent. N, m are each 1 to 2 integer

1 2

It represents the number, k, 1 each represents 3-4 integer. However, n + k = 5, and a l + m = 5. )

(45) wherein the compound represented by the general formula (1A) is to feature to be represented by the following general formula (14A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

[0119] [Formula 50] - general formula (14A)

[0120] (wherein, R, R each independently represents a hydrogen atom or a substituent. N, m are each 1 to 2 integer

1 2

It represents the number, k, 1 each represents 3-4 integer. However, n + k = 5, and a l + m = 5. )

(46) wherein the compound represented by the general formula (1A) is to feature to be represented by the following general formula (15A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

[0121] [Formula 51]

- general formula 5A)

[0122] (wherein, R, R each independently represents a hydrogen atom or a substituent. N, m are each 1 to 2 integer

1 2

It represents the number, k, 1 each represents 3-4 integer. However, n + k = 5, and a l + m = 5. Z

1

, Z, Z, Z represents an aromatic heterocyclic ring containing at least one 6-membered each nitrogen atom. )

2 3 4

(47) wherein the compound represented by the general formula (1A) is to feature to be represented by the following general formula (16A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

[0123] [Formula 52] Formula (16A)

[0124] (wherein, o, p each represent an integer of 1 to 3, Ar, Ar are each Ariren group or a divalent Kaoru

1 2

It represents an aromatic heterocyclic group. Z, Z are each aromatic double 6-membered containing at least one nitrogen atom

1 2

Represents heterocycle, L represents a divalent linking group. )

(48) wherein the compound represented by the general formula (1A) is to feature to be represented by the following general formula (17A) of (18) to (22), an organic elect according to item 1 Zureka mouth luminescence element.

[0125] [Formula 53] Formula Pai7arufa)

[0126] (wherein, o, [rho each represent a integer of 1 to 3, Ar, Ar are each Ariren group or a divalent Kaoru

1 2

It represents an aromatic heterocyclic group. Z, Z, Z, Z is each a nitrogen atom containing at least one 6-membered Kaoru

1 2 3 4

Represents aromatic heterocycle, L represents a divalent linking group. )

(49) wherein (15) to (48) of!, The display device characterized by having an organic elect device as described in item 1 Zureka.

[0127] (50) wherein (15) to (48) lighting apparatus characterized by having an organic elect device as claimed in any one of. Effect of the invention

[0128] The present invention exhibit high luminous efficiency and a long organic EL device material emission lifetime organic EL element, it is possible to provide an illumination device and a display device.

BRIEF DESCRIPTION OF THE DRAWINGS

[0129] FIG. 1 is a schematic diagram showing an example of an organic EL element force is also composed of a display device.

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

3 is a schematic diagram of a pixel.

4 is a schematic drawing of a display employing a passive matrix method.

It is a schematic diagram of FIG. 5 the illumination device.

It is a cross-sectional view of FIG. 6 lighting device.

DESCRIPTION OF SYMBOLS

[0130] 1 display

3 pixels

5 scanning lines

6 data lines

7 power line

10 organic EL element

11 switching transistor

12 horse-ku, dynamic transistor

13 capacitor

A display unit

B control unit

101 organic EL device

102 glass cover

105 cathode

106 organic EL layer

107 transparent electrode-attached glass substrate

108 Nitrogen gas 109 Tomizuzai

BEST MODE FOR CARRYING OUT THE INVENTION

[0131] The present inventors have intensively studied was performed results for problems of the conventional ortho metal complex, combined plurality of sets of different ligand having a specific structure as a ligand an ortho metal complex spoon compound organic EL element manufactured using the show high luminous efficiency than conventional, and found that light emission lifetime is significantly improved. The organic EL device using the illumination device and a display device was produced showed similarly excellent characteristics.

[0132] Tsu the mechanism to obtain such an effect, elucidated to! / Is Te, Do, but by combining the different ligands number multiple, self-organization of organic EL device material comprising an emission center Alternatively excimer emission by self-assembly I spoon is suppressed, and estimated to achieve high luminous efficiency.

[0133] Hereinafter, details of each component according to the present invention will be sequentially described.

[0134] Te Contact ヽ the present invention, the organic EL device containing the organic EL device material, an organic EL element material forms a ヽ deviation of the organic layer constituting the organic EL device or an organic layer It represents an organic EL device contained in the. The layer structure of the organic EL device of the present invention, separately, will be described in detail.

[0135] The content layer of the metal complex according to the present invention (the organic EL device material), the light-emitting layer and / or hole blocking layer. When contained in the emission layer, by using as a light emitting dopant bets in the light-emitting layer, it is possible to achieve a long life of the luminescent lifetime of which is the object organic EL device of the present invention.

[0136] [metal complex]

Tsu the metal complex represented by the general formula according to the present invention, Te is described.

[0137] The organic EL device material of the preferred embodiment (1) of the present invention and the present invention is characterized in that the ortho metal complex represented by the general formula (1).

[0138] In the formula, M represents a Group 8 to 10 metal elements in the periodic table. L, 1 / represents a different bidentate ligands each other, m is 1 or 2, n is 1 or 2. However, m + n is in agreement with the charge of M is 2 or 3.

[0139] partial structure ML is represented by the general formula (2), the partial structure ML 'is the general formula (3) or formula (4).

[0140] X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X

11 11 11

It represents an atomic group forming a ring A is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X

12 represents a carbon atom or a nitrogen atom, Q is an aromatic 5-6 membered together with the nitrogen atom and X

12 12

It represents an atomic group forming a ring B is a heterocyclic ring. X is 0, S, CH, CHR, CR, NR, P

1 2 2

It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl

twenty two

Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0141] X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X

21 21 21

It represents an atomic group forming a ring C is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X

22 represents a carbon atom or a nitrogen atom, Q is an aromatic 5-6 membered together with the nitrogen atom and X

22 22

It represents an atomic group forming a ring D is a heterocyclic ring. X is 0, S, CH, CHR, CR, NR, P

2 2 2

It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl

twenty two

Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0142] X, X represents a nitrogen atom or a phosphorus atom, X is coordinated to M through X, the X

31 32 3 31 32

It represents an atomic group forming a bidentate ligand.

[0143] As the aromatic hydrocarbon ring of the 6-membered, it includes a benzene ring.

[0144] Examples of the aromatic heterocyclic ring of the 5-6 membered, Okisazoru ring, Chiofen ring, furan ring, pyrrole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, Toriazoru ring and the like.

[0145] aromatic hydrocarbon ring of these 6-membered, aromatic heterocyclic 5-6 membered, if an alkyl group (eg, methyl group, Echiru group, a propyl group, an isopropyl group, (t) butyl group, a pentyl group, hexyl group, Okuchiru group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), a cycloalkyl group (e.g., cyclohexyl group, etc. cyclopentyl group, cyclohexylene), Aruke - Le group (e.g., vinyl group, Ariru group), an alkynyl group (e.g., propargyl group), also referred Ariru groups (aromatic hydrocarbon ring group, for example, off group, tolyl group, xylyl group, naphthyl group, Bifuwe - Lil group, anthryl group, Fuenantoriru group), a Hajime Tamaki (for example, pyrrolidyl group, imidazolidyl group, morpholyl group, Okisazorijiru group), an aromatic double ring group (e.g., e.g., a pyridyl group, Rimijiniru group, a furyl group, a pyrrolyl group, imidazol group, a benzimidazolyl group, a pyrazolyl group, Pirajuru group, Toriazoriru group (e.g., 1, 2, 4-Toriazoru - 1-I group, 1, 2, 3 Toriazoru - 1 - I le group), Okisazori group, benzo O hexa benzotriazolyl group, a thiazolyl group, Isookisazoriru group, isothiazolyl group, Furaza - group, Choi - group, a quinolyl group, a benzofuryl group, dibenzofuryl group, Benzochi E - group, Jibenzoche - group, indolyl group, carbazolyl group, carbolinyl group, (indicating that one of the carbon atoms constituting the carboline ring is one Okikawa a nitrogen atom) di § Zakarubazoriru group, quinoxalinyl group, pyridazinyl group, triazinyl group, quinazolinyl group, Futarajuru group), an alkoxyl group (e.g., methoxy, ethoxy , Puropiruoki sheet group, Penchiruokishi group, to Kishiruokishi group, Okuchiruokishi group, Dodeshiruokishi group), cycloalkoxyl group (e.g., cyclopentyl Ruo alkoxy group, Kishiruokishi group cyclohexylene, etc.), Ariruokishi group (e.g., phenoxy group, Nafuchiruokishi group) , alkylthio O group (e.g., methylthio group, Echiruchio group, propylthio group, a pentylthio group, a cyclohexylthio group, Okuchiruchio group, dodecylthio group, etc.), cycloalkylthio groups (for example, cyclopentylthio group, cyclohexylthio group cyclohexylene, etc.), Ariruchio group (e.g., phenylene group, a heteroarylthio group, naphthylthio group, etc.), alkoxycarbonyl - Le group (e.g., Mechiruokishikaru ball - group, E chill O propoxycarbonyl - group, butyl O propoxycarbonyl - group, Okuchiruokishi carbo - group, Dodeshiruokishika Ball - Le group), § reel O propoxycarbonyl - Le group (for example, Hue - Ruokishikarubo - group, naphthyl O propoxycarbonyl - Le group), a sulfamoyl group (e.g., Aminosuruho - group, methylaminosulfonyl - group, dimethylaminosulfonyl - group, butylaminosulfonyl - group, a hexyl aminosulfonyl - group, cyclohexylene Kishiruaminosu sulfo - group, O-lipped Le aminosulfonyl - group, dodecyl aminosulfonyl - group, Hue - Ruami Nosuruho - group, naphthyl aminosulfonyl - group, 2-pyridyl aminosulfonyl - Le group), © raid group (e.g., methylureido group, Echiruureido group, pentyl roux laid group, Kishiruureido group cyclohexylene, Okuchiruureido group, dodecyl ureido group, Fueniruureido group, naphthyl Chiruureido group, 2-pyridyl-amino ureido group), Ashiru group (e.g. Asechiru group, E Chirukarubo - group, propyl carbo - group, Penchirukarubo - group, Okuchirukarupo - - group, cyclohexyl-carbonitrile cyclohexylene group, the 2-Echiru Kishirukarubo - group, dodecyl carboxymethyl - group, off We - Rukarubo - group, Nafuchirukarubo - group, Pirijirukarubo - Le group), Ashiruokishi group (e.g., Asechiruokishi group, Echirukarubo - Ruokishi group, blanking Chirukarubo - Ruokishi group, Okuchirukarupo - Ruokishi group, dodecyl carbonyl O alkoxy group Hue - Luke Lupo sulfonyl O carboxymethyl group), amide groups (e.g., methylcarbonyl § amino group, Echirukarubo - Ruamino group, dimethyl carbonate - Ruamino group, propyl carbo - Ruamino group

, Penchirukarubo - Ruamino group, Kishirukarubo cyclohexylene - Ruamino group, key Shirukarubo to 2 Echiru - Ruamino group, Okuchirukarubo - Ruamino group, dodecyl carboxymethyl - Ruamino group, Hue - Rukarupo - Ruamino group, Nafuchirukarubo - Ruamino group), For example the force Rubamoiru group (, Aminokarubo - group, methyl § amino carbo - group, dimethyl § amino carbo - group, flop port pills aminocarboxy - group, pentyl Rua amino carbo - Kishiruamino group, cyclohexylene carbo - group, O-lipped Rua amino carbo - group, hexyl § to 2 Echiru amino carbo - group, de de Shiruaminokarubo - group, Hue - Ruaminokarubo - group, naphthyl § amino carbo - group, 2- pyridyl § amino carbo - Le group), Surufieru group (e.g., Mechirusurufi - group, Echirusurufi - group, Buchirusurufi - group, cyclohexyl Surufi - group, the 2-Echiru Kishirusurufi - group, dodecyl sulfide - group, Hue - Rusurufi - group, naphthylsulfide El group, 2-pyridyl sulfide El group), an alkylsulfonyl - Rumotoma others Arirusuruho - Le group (e.g., Mechirusuruho - group, Echirusuruho - group, butyl Rusuruho - group, Kishirusuruho cyclohexylene - group, Kishirusuruho to 2 Echiru - group, de Deshirusuruho - group, Hue - Rusuruho - Le group, Nafuchirusuruho - group, 2-Pirijirusu sulfo - Le group), an amino group (e.g., amino group, Echiruamino group, Jimechiruamino group, Petit Ruamino group, cyclopentyl Rua amino group, Kishiruamino group into 2-Echiru, Dodeshiruamino group , § - Rinomoto, Nafuchiruamino group, 2-Pirijiruamino group), a nitro group, Yogu further have a substituent such as Shiano group Between the substituents on the aromatic hydrocarbon ring or aromatic heterocyclic ring to form a ring structure, it is also possible to adopt a condensed ring structure in which another aromatic hydrocarbon ring or aromatic heterocyclic ring with .

Represented by the above R, an alkyl group, a cycloalkyl group, Aruke - group, Ariru group, double heterocyclic group, an aromatic heterocyclic group, each of said 6-membered aromatic hydrocarbon ring, 5-6 membered alkyl group mentioned as the substituent for the aromatic heterocyclic ring, a cycloalkyl group, an alkenyl group, § Li Lumpur group, a heterocyclic group, the same meanings as aromatic heterocyclic group. [0147] The organic EL device material of the embodiment (2) is characterized in that the ortho metal complex represented by the general formula (5).

[0148] In the formula, M represents a Group 8 to 10 metal elements in the periodic table. ml is 1 or 2, nl is 1 or 2. However, ml + nl is consistent with charge of M is 2 or 3. X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X

11 11 11

It represents an atomic group forming a ring A is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X

12 represents a carbon atom or a nitrogen atom, Q. 5 to

12 is a nitrogen atom and X

It represents an atomic group forming a 12 with a 6-membered aromatic heterocyclic ring B. X is 0, S, CH, CHR, CR, NR, P

1 2 2

It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl

twenty two

Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0149] X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X

21 21 21

It represents an atomic group forming a ring C is a family hydrocarbon ring or 5- to 6-membered aromatic heterocycle. X

22 represents a carbon atom or a nitrogen atom, Q

22 is a nitrogen atom and X

22 together represent an atomic group forming a ring D is a 5-6 membered aromatic heterocyclic ring. X is 0, S, CH, CHR, CR, NR,

2 2 2

PR, SiR, C = 0, C = NR, represents SO or SO. R is an alkyl group, a cycloalkyl

twenty two

Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. However, ring

A and ring C, ring B and ring D does not become the same as at the same time.

[0150] The 6-membered aromatic hydrocarbon ring, a 5-6 membered aromatic heterocycle, R represents the same meaning as was mentioned base in the manner (1).

[0151] In the general formula (5), at least one of the aromatic heterocyclic ring B, or an aromatic heterocyclic ring D is a 6-membered ring, it is preferably the other is a 5-membered ring.

[0152] The organic EL device material of the embodiment (4) is characterized in that the ortho metal complex represented by the general formula (6).

[0153] In the formula, M represents a Group 8 to 10 metal elements in the periodic table. m2 is 1 or 2, n2 is 1 or 2. However, consistent with m @ 2 + n2 is 2 or 3 M charge

. X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X

11 11 11

It represents an atomic group forming a ring A is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X

12 represents a carbon atom or a nitrogen atom, Q represents an atomic group for forming a ring B is an aromatic heterocyclic 5-6 membered together with the nitrogen atom and X. X is 0, S, CH, CHR, CR, NR, P

1 2 2

It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl

twenty two

It represents a group, Ariru group, a heterocyclic group or an aromatic heterocyclic group - group, Aruke. X, X is

31 32 represents a nitrogen atom or a phosphorus atom, X is X, bidentate ligand which coordinates to M via the X

3 31 32

It represents an atomic group forming a.

[0154] The 6-membered aromatic hydrocarbon ring, a 5-6 membered aromatic heterocycle, R represents the same meaning as was mentioned base in the manner (1).

[0155] Te you, the general formula (6), preferred that the aromatic heterocyclic ring B is a 6-membered ring.

[0156] The organic EL device material of the embodiment (6), in ortho complex having the general formula (1 1) - (1-150) a partial structure or a tautomer thereof represented as a partial structure characterized in that there.

[0157] In the formula, M represents a Group 8 to 10 metal elements in the periodic table. R, R each location

Represents 11 12 substituent, nl l, nl2 represents an integer selected from each 0-2. X, X are each> N

13 14

R, represents an O or S. R is an alkyl group, a cycloalkyl group, an alkenyl

13 13

Group, a Ariru group, a heterocyclic group or an aromatic heterocyclic group. X, X, X, X, respectively

15 16 17 18

> N-R, represents a -O or -S-. R is a hydrogen atom, an alkyl group, a cycloalkyl

16 16

It represents a group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. X, X

19a 19

, X is each represents CH or N, any one or two are N. X is 0, S, C b 19c 0

It represents H, CHR, CR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is

2 2 2 2

Kill group, a cycloalkyl group, Aruke - represents a group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0158] wherein R, substituent represented by R include aromatic hydrocarbons 6 membered described in the embodiment (1)

11 12

Ring are the same as the substituents of the 5- to 6-membered aromatic heterocycle. The alkyl group, cycloalkyl group, alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group are the same as those described in the embodiment (1).

[0159] The organic EL device material of the embodiment (7), the general formula (2 1) to orthometalated complex having (2 50) parts component represented by the structure or a tautomer thereof as a partial structure and characterized in that. [0160] In the formula, M represents a Group 8 to 10 metal elements in the periodic table. R, R each location

Represents 21 22 substituent, n21, n22 is an integer selected from 0-2. X is,> N- R, - O-

23 represents the 23 or S. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru

twenty three

Group, a heterocyclic group or an aromatic heterocyclic group. X, X is,> NR, -O or

24 25 24

It represents the S. R is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, § Li

twenty four

Lumpur group, a heterocyclic group or an aromatic heterocyclic group. X, X, X are each CH or N

26 27 28

The stands, any one or two are N. X is 0, S, CH, CHR, CR, NR, PR,

0 2 2

SiR, represent a C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl group,

twenty two

An alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0161] wherein R, substituent represented by R include aromatic hydrocarbons 6 membered described in the embodiment (1)

21 22

Ring are the same as the substituents of the 5- to 6-membered aromatic heterocycle. The alkyl group, cycloalkyl group, alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group are the same as those described in the embodiment (1).

[0162] The organic EL device material of the aspect (8), the general formula (3-1) - orthometalated complex having a part partial structure or a tautomer thereof represented as a partial structure (3 10) and characterized in that.

[0163] where, M represents a Group 8 to 10 metal elements in the periodic table. R, R each location

Represents 31 32 substituent, n31, n32 is an integer selected from 0-2. X is,> N- R, - O-

31 represents the 33 or S. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru

33

Group, a heterocyclic group or an aromatic heterocyclic group. X, X is,> NR, -O or

32 33 34

It represents the S. R is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, § Li

twenty five

Lumpur group, a heterocyclic group or an aromatic heterocyclic group. X, X, X are each CH or N

34 35 36

The stands, any one or two are N. X is 0, S, CH, CHR, CR, NR, PR,

0 2 2

SiR, represent a C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl group,

twenty two

An alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0164] wherein R, substituent represented by R include aromatic hydrocarbons 6 membered described in the embodiment (1)

31 32

Ring are the same as the substituents of the 5- to 6-membered aromatic heterocycle. The alkyl group, cycloalkyl group, alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group are the same as those described in the embodiment (1).

[0165] The organic EL device material of the aspect (9), characterized in that ortho metal complex having a partial structure or a tautomer thereof represented by the general formula (7) as a partial structure.

[0166] In the formula, M represents a Group 8 to 10 metal elements in the periodic table. X is or carbon atom

41

Other represents a nitrogen atom, Q is an aromatic 6-membered together with a carbon atom and X a hydrocarbon ring or

41 41

It represents an atomic group forming a ring E is a 5- to 6-membered aromatic heterocycle. R represents a substituent, n

41

4 is an integer selected from 0-3. Xa is - N (Ra), - display the S- Ra - O-Ra or

2

It is. Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, the heterocyclic group or aromatic heterocyclic group. Xa is - N (Ra), the two Ra different even with the same

2

One is or may be. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S

4 2 2 2

It represents O or SO. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group

2

, A heterocyclic group or an aromatic heterocyclic group.

[0167] substituent group represented by R, the 6-membered described in the embodiments (1) an aromatic hydrocarbon ring, 5

41

It is synonymous with the substituent of the 6-membered aromatic heterocycle. The alkyl group, cycloalkyl group, alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group are the same as defined was mentioned base in the manner (1).

[0168] O Rutometaru complex having the general formula (7) a partial structure or a tautomer thereof represented as a partial structure, the general formula (8) or (9) represented by the partial structure or a tautomeric with it is preferably ortho metal complex having a sexual body as a partial structure.

[0169] In the formula, M represents a Group 8 to 10 metal elements in the periodic table. R, R, R, R

51 52 53 54 each represents a hydrogen atom or an electron donating substituent, at least one is an electron-donating substituent. R, R, R, R

56 57 58 59 each represents a hydrogen atom or a substituent, R, R

56 At least one 58 is an electron-withdrawing group. R, R represents a substituent, n51, n5

50 55

2 is an integer selected from 0-3. Xa is - N (Ra), - display the S- Ra - O-Ra or

2

It is. Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, the heterocyclic group or aromatic heterocyclic group. Xa is - N (Ra), the two Ra different even with the same

2

One is or may be. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S

5 2 2 2

It represents O or SO. R represents an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0170] The electron-donating substituent refers to a substituent that indicates the value of sigma [rho value of Hammett's negative described below, such substituents are electron binding atoms side as compared with the hydrogen atom having a given and hungry characteristics.

[0171] Specific examples of the substituent having an electron donating property, a hydroxyl group, an alkoxy group (e.g., methoxy), Asechiruokishi group, an amino group, Jimechiruamino group, Asechiruamino group, § alkyl group (e.g., methyl group, Echiru group, propyl group, and tert- butyl group), Ariru group (e.g., off group, mesityl group, etc.).

[0172] For example, as the fine mosquito over 0.20 or less electron donating group, cycloprothrin Building group (one 0.21), cyclohexyl group (- 0. 22), tert-butyl (- 0. 20), - CH Si (CH) (- 0.

2 3 3

21), amino group (one 0.66), hydroxyl § amino group (one 0. 34), -NHNH (- 0. 55),

2

-NHCONH (one 0.24), single NHCH (- 0. 84), one NHC H (- 0. 61), one NHC

2 3 2 5

ONHC H (. -0 26), -NHC H (- 0. 51), one NHC H (- 0. 40), one N = CH

2 5 4 9 6 5

CH (- 0. 55), one OH (- 0. 37), one OCH (- 0. 27), one OCH COOH (- 0. 3

6 5 3 2

3), -OC H (-0 24), -OC H (-. 0. 25), one OCH (CH) (- 0. 45), one OC

2 5 3 7 3 2

H (one 0.34), single OCH CH (- 0. 42), and the like.

5 11 2 6 5

[0173] Also, the Hammett sigma [rho value, for example, can be referred to below literature.

[0174] Roh, the sigma [rho value of Met refers to Hammett's substituent constant sigma [rho. The value of the Hammett's sigma [rho is the electronic effect force substituent constant determined Me was of substituents on the hydrolysis of Echiru benzoate by Ham Mett et al., "Structure-Activity Relationships of drugs" (Nankodo: 1979) , it can be cited rsubstitu ent Constants for Correlation Analysis m chemistry and biologyj the (C. Hansch and A. Leo, John Wiley & Sons, New York, 1979 years) serial mounting of groups, and the like.

[0175] As the electron-donating substituent, among the groups, and most preferably an alkyl group, alkoxy group, and an alkylamino group.

[0176] Examples of the substituent, an aromatic hydrocarbon ring 6 membered described in the embodiment (1) are the same as the substituents of the 5- to 6-membered aromatic heterocycle. The alkyl group, cycloalkyl group, Aruke - group, Ariru group, a heterocyclic group or an aromatic heterocyclic group are the same as those described in the embodiment (1).

[0177] The organic EL device material of the aspect (11), wherein the expressed or partial structure in the general formula (10) is ortho metal complex having a tautomer thereof as a partial structure.

[0178] In the formula, M represents a Group 8 to 10 metal elements in the periodic table. X, X, X, X

61 62 63 64 each represent a carbon atom or a nitrogen atom, Q

61 carbon atoms and X, X

Table atoms forming a ring F is 61 63 with 6-membered aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocyclic

OC

And, Q is to form a ring G is a nitrogen atom and X Bok ilO- L, 5~6 membered aromatic heterocyclic ring together with X

62 62 64

It represents a group of atoms that. Divination

X, X is the van der Waals volume of 20

h represents the k A 3 or more at which substituent

, M6, n6 is 0 or 1. However, it is m6 + n6≥l. X is 0, S, CH, CHR,

6 2

It represents CR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a consequent

2 2 2

Mouth alkyl group, an alkenyl group, an Ariru group, a heterocyclic group or an aromatic heterocyclic group.

[0179] The 6-membered aromatic hydrocarbon ring, aromatic heterocyclic 5-6 membered the same meanings as those described in the embodiment (1).

[0180] The van der Waals (VDW) volume of substituents, a substituent is introduced into the force benzene ring using a parameter obtained by using the Accelrys Inc. molecular simulation into four soft Cerius2, using Dreiding Force Field , to optimize the molecular structure MM calculation is defined as Volume value obtained using the Connoly Surface. It shows the fan de Norre Wa Roh less (VDW) volume of the specific substituents below.

Substituent A 3

Methyl 25.4

Echiru based on

Isopropylidene Norre based on

tert- Buchinore based on

Phenyl group

Methoxy group

Amino group 22.2

A hydroxyl group

Chlorine atom 22.4 bromine atom 26.5

Fluorine atom 13.3

Triflate Ruo b methyl 42.5

The alkyl group, cycloalkyl group, Aruke - group, Ariru group, a heterocyclic group or an aromatic heterocyclic group are the same as those described in the embodiment (1).

[0182] Formula O Rutometaru complex having a partial structure or a tautomer thereof represented by (10) as a partial structure, the general formula (11) partial structure represented by - (14) or a tautomeric it is preferably ortho metal complex having a sexual body as a partial structure.

[0183] In the formula, M represents a Group 8 to 10 metal elements in the periodic table. X, X, X, X

71 72 73 74 each represent a carbon atom or a nitrogen atom, Q is a carbon atom, X, X

71 71 73 with represents an atomic group forming a ring H is Kaoru aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocyclic 6-membered, Q is a nitrogen atom, X, aromatic 5-6 membered with X atoms forming the ring K is a group heterocyclic

23 72 74

Representing the group. Q

73 represents an atomic group forming an aromatic hydrocarbon ring or aromatic heterocyclic ring with the carbon atoms. Q

74 represents an atomic group forming an aromatic heterocyclic ring together with the nitrogen atom. X

7

0 represents S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, SO or SO.

2 2 2 2

R represents an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, a heterocyclic group, or Kaoru aromatic heterocyclic group.

[0184] The 6-membered aromatic hydrocarbon ring, aromatic heterocyclic 5-6 membered the same meanings as those described in the embodiment (1).

[0185] The alkyl group, cycloalkyl group, Aruke - group, Ariru group, a heterocyclic group or an aromatic heterocyclic group are the same as those described in the embodiment (1).

[0186] The organic EL device material of the aspect (13), the general formula (4) or general formula (6) X - X

31

Bidentate ligand formed by -X is represented by the above general formula (4 1) to (4 31)

3 32

Characterized in that the partial structure or or a tautomer thereof ortho metal complex having as a partial structure.

[0187] In the formula, R represents an R -CO- or R -SO-, R represents an alkyl group, a cycloalkyl

81 80 80 2 80

It represents a group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. R, R, R, R

82 83 86 87 represents the location substituent, n represents an integer of 0 to 3, n, n represents an integer of 0 to 2. R, R, R,

81 82 83 84 85 88 R is an alkyl group, a cycloalkyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group

89

A representative. Q represents an atomic group forming an aromatic heterocyclic 5-6 membered carbon, together with the nitrogen,

81

Q, Q represents an atomic group forming an aromatic heterocyclic ring of 5-membered carbon, together with the nitrogen.

82 83

[0188] Aromatic heterocycles of the 5-6 membered have the same meanings as those described in the embodiment (1).

[0189] The alkyl group, cycloalkyl group, Aruke - group, Ariru group, a heterocyclic group or an aromatic heterocyclic group are the same as those described in the embodiment (1).

[0190] The organic EL device material of the aspect (14), said all of the general formula, wherein the ortho metal complex of M force Irijiu beam or platinum.

[0191] The preferred ortho metal complex used in the present invention are shown below.

[0192] [of 54]

[0193] [of 55]

[0194] [of 56]

[0195] [of 57]

[0196] [of 58]

[0197] [of 59] [09 ^] [8610]

llC0C / 900Zdf / X3d 09 0ΖΪ860 / 900Ζ OAV

[0199] [of 61]

[0200] [of 62]

[0201] [of 63]

[0202] [of 64]

[0203] [of 65] [99 ^] 0]

[0205] [of 67]

[0206] [of 68]

[0209] [I spoon 71]

[0210] [of 72]

[0211] [of 73]

[0212] [of 74]

[0213] [of 75]

[0214] [of 76]

[0215] [of 77]

These I 匕合 may, for example, Organic Leter, voll3, No. 16, p2579~2581 (2

001), Inorganic Chemistry, vol30, No. 8, pl685~1687 (1991), J. Am. Chem. Soc., Voll23, p4304 (2001), Inorganic Chemistry, vol41, No. 1 2, pl3056~3066 (2002 ), New Jounal of Chemistry, vol26, pi 171 (20

02), cut with synthesized by further applying the method of references such as described in these documents.

[0217] In the present invention, the organic EL device material, to produce any of the constituting layers the organic EL element is contained in the (organic layer) constituting the organic EL element.

[0218] The organic EL element has a light-emitting layer as a constituent layer, light emitting layer is preferably a containing the organic EL device material. When contained in the emission layer, by using as a light emitting dopant in the emissive layer, leaving at you to achieve a long life of the luminescent lifetime of which is the object organic EL device of the present invention.

[0219] Further, the organic EL device has a hole blocking layer as a constituent layer, the hole blocking layer is the organic E

It is preferable, to contain L element material.

[0220] The organic EL device of the aspect (18) is characterized by containing a compound represented by the general formula (1A).

[0221] In the formula, Z is an aromatic heterocyclic ring, Z is an aromatic heterocyclic ring or an aromatic hydrocarbon ring

1 2

Represents, Z represents a divalent linking group or a single bond. R is a hydrogen atom or a substituent

3 101

Represent.

[0222] Te you, the general formula (1 A), Z is O may have a substituent group! Represents an aromatic heterocyclic ring, Z is

1 2 substituent an aromatic heterocyclic ring which may have, or an aromatic hydrocarbon ring, Z

3 represents a divalent linking group or a single bond. R

101 represents a hydrogen atom or a substituent.

[0223] Z, the aromatic heterocyclic ring represented by Z, a furan ring, Chiofen ring, a pyridine ring, pyridinium

1 2

Dajin ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a benzimidazole ring, Okisajia tetrazole ring, Toriazoru ring, an imidazole ring, a pyrazole ring, a thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, O benzoxazole ring, Kinokisari mentioned down ring, a quinazoline ring, a phthalazine ring, a force carbazole ring, a carboline ring, etc. Jiazakarubazo Le ring (indicating the ring one of the carbon atoms of a hydrocarbon ring constituting a carboline ring is further substitution at the nitrogen atom) is It is. R Furthermore the aromatic heterocyclic ring, which will be described later

Yo ヽ have a substituent represented by 101.

[0224] The aromatic hydrocarbon ring represented by Z, a benzene ring, Bifuwe - Le ring, a naphthalene ring

2

, Azuren ring, anthracene ring, Fuenantoren ring, pyrene ring, Tarisen ring, a naphthacene ring, bird whistle - Len ring, o- Terufue - Le ring, m- Terufue - Le ring, p- Terufue - Le ring, § Senafuten ring, coronene ring, fluorene ring, fluoranthrene ring, a naphthacene ring, penta Sen ring, perylene ring, a pentaphene ring, a picene ring, a pyrene ring, pyranthrene ring, Ansuraa Ntoren ring and the like. Further, the aromatic hydrocarbon ring is represented by R described later

Choi a 101 Ru substituents.

Examples of the substituent represented by R, an alkyl group (e.g., methyl group, Echiru group, propyl

101

Group, an isopropyl group, tert- butyl group, a pentyl group, a hexyl group, Okuchiru group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), a cycloalkyl group (e.g., cyclohexyl group, etc. cyclopentyl group, cyclohexylene) , Aruke - Le group (e.g., Bulle group, Ariru group), an alkynyl group (e.g., Echiniru group, propargyl group, etc.), Ariru group (e.g.

Hue - group, a naphthyl group, etc.), aromatic Hajime Tamaki (e.g., furyl group, Choi - group, pyridyl group, Piridaji - group, pyrimidine - group, Pirajuru group, triazinyl group, an imidazolyl group, pyrazolyl group, a thiazolyl group, Kinazori - group, a phthalazinyl group), a Hajime Tamaki (eg example, pyrrolidyl group, imidazolidyl group, morpholyl group, Okisazorijiru group), an alkoxy sill group (e.g., methoxy group, an ethoxy group, Puropiruokishi group, Penchiruokishi group, the key Shiruokishi group, Okuchiruokishi group, Dodeshiruokishi group), if e cycloalkoxyl group (e.g., cyclopentyl Ruo alkoxy group, Kishiruokishi group cyclohexylene, etc.), if Ariruokishi group (eg, phenoxy group, Nafuchiruokishi group) , an alkylthio group (e.g., methylthio group, E Chiruchio group, propylthio group, Bae Nchiruchio group, to cyclohexylthio group, Okuchiruchio group, dodecylthio group, etc.), cycloalkylthio groups (for example, cyclopentylthio group, cyclohexylthio group cyclohexylene, etc.), Ariruchio group (e.g., Hue - thio group, naphthylthio group, etc.), alkoxycarbonyl - Le group (e.g., methyl O propoxycarbonyl - group, E chill O propoxycarbonyl group, butyl O propoxycarbonyl - group, O-lipped Ruo propoxycarbonyl - group, Dodeshiruokishi carbo - Le group), Ariruokishi carbo - Le group (e.g., Hue - Ruokishikarubo - group, naphthyl O propoxycarbonyl - Le group), a sulfamoyl group (e.g., Aminosuruho - group, methylaminosulfonyl - group, dimethylaminosulfonyl - group, butylamino sulfo - group, a hexyl aminosulfonyl - group, hexyl aminosulfonyl cyclohexylene - group, Okuchiruaminosu sulfo - Group, dodecyl aminosulfonyl - group, Hue - Ruaminosuruho - group, naphthylamine Nosuruho - group, 2-pyridyl aminosulfonyl - Le group), Ashiru group (e.g., Asechiru group, Echirukarubo - group, propyl carbo - Le group , Penchirukarubo - group, cyclohexylene key Shirukarubo - group, Okuchirukarupo - group, Kishirukarubo to 2 Echiru - group, de de Shirukarubo - group, off - Rukarupo - group, Nafuchirukarubo - group, pyridyl carbo - Le group), Ashiruokishi group (e.g., Asechiruokishi group, E chill carbonyl O alkoxy group, Buchirukarubo - Ruokishi group, Okuchirukarubo - Ruokishi group, dodecyl carboxymethyl - Le Okishi group, Fuenirukarubo - Ruokishi group), an amido group (e.g. , Mechirukarubo - Ruami amino group, Echirukarubo - Ruamino group, dimethyl carbonate - Ruamino group, propyl carbo - Rua Amino group, Penchirukarubo - Ruamino group, cyclohexylene Kishirukarubo - Ruamino group, the 2-Echiru Kishirukarubo - Ruamino group, Okuchirukarubo - Ruamino group, dodecyl carboxymethyl - Ruamino group, off - Rukarupo - Ruamino group, Nafuchirukarubo - Ruamino group) force Rubamoiru group (e.g., Aminokarubo - group, methyl § amino carbo - group, dimethyl § amino carbo - group, propylamino carbo - group, pentyl Rua amino carbo - group, Kishiruamino force Lupo cyclohexane - Le group, O-lipped Rua amino carbo - group, hexyl § to 2 Echiru amino carbo - group, dodecyl § amino carbo - group, Hue - Ruaminokarubo - group, naphthyl § amino carbo - group, 2- Pirijirua amino group etc.), a ureido group (e.g., methylureido group, E Ji Ruureido group, pentyl roux raid group, cyclohexylene Kishiruure De group, Okuchiruureido group, de Deshiruureido group, full Niruureido group Nafuchiruureido group, 2-pyridyl-amino ureido group), Surufieru group (e.g., Mechirusurufi - group, Echirusurufi - group, Petit Rusurufi - group, cyclohexylene Kishirusuru Fier group, 2-Echiru hexyl sulfide El group, dodecyl sulfide El group, Fuwenirusurufi - group, Nafuchirusurufi - group, 2-Pirijirusurufi - Le group), an alkylsulfonyl - Le group (e.g., Mechirusuruho - group, E Chirusuruho - group, Buchirusuruho - group, Kishirusuruho cyclohexylene - group, Kishirusuruho to 2 Echiru - group, dodecyl sulfo - Le group), Arirusuruho - Le group (Hue - Le sulfo - Le group , Nafuchirusuruho - group, 2-Pirijirusuruho - Le group), amino group (eg, amino group, Echiru Amino group, Jimechiruamino group, Buchiruamino group, cyclopentyl Rua amino group, 2-Echiru to Kishiruamino group, Dodeshiruamino group, § - Rinomoto, Nafuchiruamino group, 2 Pirijiruamino group), a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom), fluorinated hydrocarbon radicals (e.g., Furuoromechiru group, triflate Ruo Russia methyl, Pentafuruo port Echiru group, penta full O Loftus et - le group), Shiano group, a nitro group, a hydroxyl group, mercapto group, silyl group (e.g., trimethylsilyl group, triisopropoxide building silyl group, bird whistle - Le silyl group, phenylene Rujechirushiriru group), and the like.

[0226] These substituents may be further substituted with the substituents described above. Further, these substituents to form a ring plurality of bonded together, even. Preferred as the substituent, an alkyl group, a cycloalkyl group, a fluorinated hydrocarbon group, Ariru group, an aromatic heterocyclic group.

[0227] Examples of the divalent linking group represented by Z, alkylene, Aruke -, alkylene, § Li

3

Other hydrocarbon groups such as one lens, Yogumata Chiofen 2 also comprise a hetero atom, 5 Jiiru group Ya pyrazine 2, 3 compound having an aromatic heterocycle such as Jiiru group (heteroaromatic it may be a divalent linking group derived from also referred) and the compound may be oxygen and chalcogen atoms such as sulfur. Further, alkylimino group, a hetero atom may be a group of linked gathered the like dialkylsilane Jiiru group Ya di § reel germane Jiiru group.

[0228] a single bond is a bond that binds to the substituent groups to each other directly linked.

[0229] In the present invention, it is preferable that the a Z force ½-membered ring of the general formula (1A). To this

1

Ri, can be increased more luminous efficiency. Furthermore it is possible to further long life. In the present invention, it is preferable that the Z force ½ membered ring. Thus, high more luminous efficiency

2

Can Kusuru. It is possible to even more further long life. In addition Z

1 and Z

With 2 together 6-membered ring, it is preferable because it is high as more luminous efficiency. It preferred because it is possible to even more further long life. In addition, z

3 is not preferable to be a bond. This makes it possible to increase the more luminous efficiency, it can be further longer life. Further compounds of the general formula (1A) may be molecular weight high luminous efficiency which is preferably tool is 450 or more, it is possible to longer life.

[0230] Preferred compounds represented by the general formula (1A), the general formula (1A- 1) ~ (: LA

Are each compounds represented by 10).

[0231] In the general formula (1A- 1), R ~R each independently represent a hydrogen atom or a substituent

501 507

A representative. Formula (1A - 1) By using the compound represented by may be a more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0232] In the general formula (1A- 2), R ~R each independently represent a hydrogen atom or a substituent

511 517

A representative. Formula (1A - 2) By using the compound represented by may be a more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0233] In the general formula (1A- 3), R ~R each independently represent a hydrogen atom or a substituent

521 527

A representative. Formula (1A - 3) By using the compound represented by may be a more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0234] In the general formula (1A- 4), R ~R each independently represent a hydrogen atom or a substituent

531 537

A representative. Formula (1A - 4) By using the compound represented by may be a more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0235] In the general formula (1A- 5), R ~R each independently represent a hydrogen atom or a substituent

541 548

A representative. Formula (1A - 5) By using the compound represented by may be a more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0236] In the general formula (1A- 6), R ~R each independently represent a hydrogen atom or a substituent

551 558

A representative. Formula (1A - 6) By using the compound represented by may be a more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0237] In the general formula (1A- 7), R ~R each independently represent a hydrogen atom or a substituent

561 567

A representative. Formula (1A - 7) By using the compound represented by may be a more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0238] In the general formula (1A- 8), R ~R each independently represent a hydrogen atom or a substituent

571 577

A representative. Formula (1A - 8) By using the compound represented by may be a more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0239] In the general formula (1A- 9), R represents a hydrogen atom or a substituent. Further, the plurality of R may each have Yogu be the same or different. By have use a compound represented by the general formula (1 A- 9), it can be more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0240] In the general formula (1A- 10), R represents a hydrogen atom or a substituent. Further, the plurality of R may each have Yogu be the same or different. By use of the general formula (1 A- 10) a compound represented by may be a more luminous efficient organic EL element. Further it can be an organic EL element having a long lifetime.

[0241] Also preferred compounds represented by the general formula (1A), the general formula (2A- 1) ~ (2A- 10) a compound having at least one group represented by any one of it is. In particular, the general formula in the molecule (2A- 1) of ~ (2A- 10), and more preferably has four from two groups represented by or misalignment. At this time, including when to replace the structure represented by the general formula (1A), the dividing R, was part Formula (2A- 1) ~ (2A- 10).

101

[0242] In this case, it is preferable for obtaining the effects of the present invention is particularly compounds represented by the general formula (3A) ~ (17A).

[0243] In the general formula (3A), R ~R each represents a hydrogen atom or a substituent, R ~

601 606 601

At least one of the general formula R (2A- 1) of ~ (2A- 10), the group represented by any deviation

606

A representative. By using a compound represented by the general formula (3A), it can be more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0244] In the general formula (4A), R ~R each represents a hydrogen atom or a substituent, R ~

611 620 611

At least one of the general formula R (2A- 1) of ~ (2A- 10), the group represented by any deviation

620

A representative. By using a compound represented by the general formula (4A), it can be more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0245] In the general formula (5A), R ~R each represents a hydrogen atom or a substituent, R ~

621 623 621

At least one of the general formula R (2A- 1) of ~ (2A- 10), the group represented by any deviation

623

A representative. By using a compound represented by the general formula (5A), it may be a more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0246] In the general formula (6A), R ~R each represents a hydrogen atom or a substituent, R ~

631 645 631

At least one of the general formula R (2A- 1) of ~ (2A- 10), the group represented by any deviation

645

A representative. By using a compound represented by the general formula (6A), it can be more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0247] In the general formula (7A), R ~R each represents a hydrogen atom or a substituent, R ~

651 656 651

At least one of the general formula R (2A- 1) of ~ (2A- 10), the group represented by any deviation

656

A representative. na represents an integer of 0 to 5, nb represents an integer of 1-6, the sum of na and nb is Ru 6 der. By using a compound represented by the general formula (7A), it can be a more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0248] In the general formula (8A), R ~R each represents a hydrogen atom or a substituent, R ~

661 672 661

At least one of the general formula R (2A- 1) of ~ (2A- 10), the group represented by any deviation

672

A representative. By using a compound represented by the general formula (8A), it can be more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0249] In the general formula (9A), R ~R the force R ~ represents a hydrogen atom or a substituent

681 688 681

At least one of the general formula R (2A- 1) of ~ (2A- 10), the group represented by any deviation

688

A representative. By using a compound represented by the general formula (9A), it can be more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0250] In the general formula (10A), the force R to R represents a hydrogen atom or a substituent R

691 700 691

At least one ~R's! / Formula (2A- 1) ~ (2A- 10), represented by either displacement

700

It represents a group.

[0251] Examples of the divalent linking group represented by L, an alkylene group (e.g., ethylene group, trimethylene

1

Down group, a tetramethylene group, a propylene group, Echiruechiren group, pentamethylene group, hexamethylene group, 2, 2, 4 Kisamechiren group to trimethyl, heptamethylene group, Otatamechiren group, nonamethylene group, decamethylene group, Undekamechiren group, dodecamethylene group, a cyclohexylene group (e.g., 1, 6 cycloheteroalkyl Kisanjiiru group), cyclopentylene groups (e.g., 1, 5 cyclopentane Jiiru group), etc.), Aruke - Len group (e.g., bi - Len group, Pro base - Ren group), alkyl - alkylene group (e.g., E Ji - Ren group, 3-pentylene - alkylene group), other hydrocarbon groups, such as § arylene group, a group containing a hetero atom (eg, O , a divalent group containing a chalcogen atom, such as one S, N (R) - group, wherein R represents a hydrogen atom or an alkyl group, the alkyl group, the general formula (1A) Contact, Te in R represented The alkyl group and

101

It includes synonymous a is), and the like. Further, the alkylene group, Aruke - Len group, an alkylene group, in each of Ariren group, one at least of the carbon atoms constituting the divalent linking group, chalcogen atom (oxygen, sulfur, etc.) and the N (R) - it may be substituted with group.

[0252] Examples of further divalent linking group represented by L, such as use a group having a divalent heterocyclic group Irare, for example, O benzoxazole Jiiru group, pyrimidine Jiiru group, pyridazine Jiiru group, Pi Ranjiiru group, Pirorinjiiru group, imidazo Rinjii group, imidazolidine Jiiru group, pyrazole Rijinjiiru group, Pirazorinjiiru group, piperidines Rijinjiiru group, piperidines Rajinjiiru group, moles Horinjiiru group, quinuclidine Jiiru group and the like, also Chiofen 2, 5 and Jiiru groups, such as pyrazine 2, 3 Jiiru group, or a divalent linking group derived from a compound having an aromatic heterocycle (also referred to as heteroaryl Kaoru aromatic compound). Further, alkylimino, it is a group of linked gathered heteroatoms such as dialkyl silanes Jiiru group Ya di § reel germane Jiiru group.

[0253] By using the compound the represented by the general formula (10A), it can be more luminous efficient organic EL element. It can be even more with the organic EL element having a long lifetime.

[0254] In each compound represented by the general formula (11A) ~ formula (15A), R, with R the

1 2 s The substituents represented same meanings as the substituents represented by R are in the general formula (1A)

101

It is.

[0255] In the general formula (15A), Z, Z, Z, represented by each of Z, fewer each nitrogen atom

1 2 3 4

The aromatic heterocyclic 6-membered containing one Kutomo, for example, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring and the like.

[0256] In the general formula (16A), Z, represented by each of Z, each nitrogen atom of at least

The aromatic heterocyclic ring 1 2 one containing 6-membered, for example, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring and the like.

[0257] Ar, as a Ariren group each represented by Ar, o Hue - Len group, m- Hue - Len group

1 2

, P Hue - Len group, naphthalene Jiiru group, anthracene Jiiru group, Nafutasenjiiru group, Pirenjiiru group, naphthyl naphthalene Jiiru group, Bifue - Rujiiru group (e.g., 3, 3 'Bifuwe - Rujiiru group, 3, 6-Bifuwe - Rujiiru group etc.), Terufue - Rujiiru group, quaterphenyl Terufue - Rujiiru group, Kinkufue - Rujiiru group, Sekishifue - Rujiiru group, Sepuchifu E - Rujiiru group, Okuchifue - Rujiiru group, Nobifue - Rujiiru group, Deshifue - Rujii group, and the like. Also, the Ariren group may further have a later-described substituent. Ar, 2-valent aromatic heterocyclic group represented by each Ar is a furan ring, Chiofen ring,

1 2

A pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a benzimidazole ring, Okisajiazoru ring, Toriazoru ring, an imidazole ring, a pyrazole ring, a thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, O benzoxazole ring , quinoxaline ring, quinazoline ring, phthalazine ring, the force carbazole ring, a carboline ring, such as a divalent group in which the carbon atoms of the hydrocarbon ring is further rings Hitoshiryoku derived is substituted with a nitrogen atom constituting the force Ruporin ring and the like. Further, the aromatic heterocyclic group, said R

Yo ヽ have a substituent represented by 101.

Examples of the divalent linking group represented by [0258] L, in the general formula (10A), 2 represented by L

1

Is the force preferably the same meaning as valence linking group is a divalent group containing an alkylene group, a chalcogen atom, such as an OS, and most preferably an alkylene group.

[0259] In the general formula (17A), Ar, Ariren group represented by each of Ar, the general

1 2

It is synonymous with Ariren groups each represented Ar, with Ar in formula (16A). Ar, each in Ar

1 2 1 2 s aromatic heterocyclic group represented, in the general formula (16A) Ar, is represented by each of Ar

1 2

It is synonymous with divalent aromatic heterocyclic group that.

[0260] Z, Z, Z, represented by each of Z, each aromatic containing at least one 6-membered nitrogen atom

1 2 3 4

Examples of the heterocyclic ring, for example, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and the levator up.

Examples of the divalent linking group represented by [0261] L, in the general formula (10A), 2 represented by L

1

Power is synonymous with valence linking group preferably a divalent group containing an alkylene group, a chalcogen atom such as OS-, and most preferably an alkylene group.

[0262] Hereinafter, specific examples of the compound represented by the general formula (1A) according to the present invention, the present invention is not limited thereto.

[0263] [of 78]

[0264] [Formula 79] Compound central skeleton A

0]

Compound central skeleton A

1]

[0267] [Formula 82] Compound central skeleton A

83]

[0269] [Formula 84] Compound central skeleton

5] compound central skeleton A

6] compound central skeleton

87] compound central skeleton A

88]

[0274] [of 89]

[0275] [of 90]

[0276] [of 91]

[26 ^] [ίίΖΟΙ

ll £ 0 £ / 900IJf / 13d! ■ 01 · 0Π860 / 900Ζ OAV

[0278] [of 93]

[0279] [of 94]

[0280] [of 95]

[0281] [of 96]

[0282] [of 97]

[0283] [of 98]

A- 105 A- 106

9] A- 114

00] A- 121

01]

[0287] [Formula 102] 112

[0288] [Chem.

[0289] [Formula 104]

[0290] [of 105]

A-147

106]

107]

[0293] [of 108]

A- 158 A- 159

109]

[0295] [of 110]

A -170

[0296] [of 111]

112]

[0298] are shown below, but representative synthesis examples of compounds according to the present invention, the present invention is not limited thereto.

[0299] (Synthesis of Exemplified Compound A- 73)

[0300] [of 113]

[0301] 4, 4 '- Jodobifue - Le 6. 87 g, beta-carboline 6. OOG New, the mixture was added into N- Jimechiruase Toamido 50 ml, mosquitoes copper powder 4. 5 g, potassium carbonate 7. 36 g卩E was heated under reflux for 15 hours. The aqueous black port Holm added After allowing to cool, the insoluble material was removed by filtration. The organic layer was separated and the aqueous was washed with saturated brine, and concentrated under reduced pressure, the resulting residue was dissolved in acetic acid, after activated carbon treatment, and recrystallized, Exemplified Compound A- 73 colorless crystal 4. obtain a 2g.

[0302] The structure of the exemplified compound A- 73 was confirmed Te cowpea in 1 H-NMR ^ vectors and mass spectrometry. Showing physical property data of Exemplified Compound A- 73, the spectral data below.

[0303] Colorless crystals, mp 200 ° C

MS (FAB) m / z: 487 (M + 1)

'H-NMR (400MHz, CDC1):. Δ / ppm 7. 3- 7. 5 (m, 2H), 7 5- 7. 6 (

3

m, 4H), 7. 7- 7. 8 (m, 4H), 7. 9- 8. 0 (m, 4H), 8. 06 (d, J = 5. 1Hz, 2H), 8. 24 ( d, J = 7. 8Hz, 2H), 8. 56 (d, J = 5. 1Hz, 2H), 8. 96 (s, 2H)

(Synthesis of Exemplified Compound A- 74)

[0304] [of 114]

[0305] Palladium acetate 0. 32 g, tri - a tert-butylphosphine 1. 17 g was dissolved in anhydrous toluene 10 ml, was added sodium borohydride 50mg, After stirring for 10 minutes at room temperature, [delta] - carboline 5. OOG, 4 , 4 'Jodobifue - Le 5. 87 g, was dispersed sodium tert-butoxy de 3. 42 g of anhydrous xylene 50 ml, under a nitrogen atmosphere for 10 hours 撹 拌 at reflux temperature. The resulting reaction mixture was separated and the organic layer was added cool after black port Holm and water, the organic layer, water, washed with brine, and concentrated under reduced pressure, the resulting residue tetrahydro was dissolved in furan, it was subjected to activated carbon treatment to obtain a colorless crystal 5. Og of exemplified compound A- 74 and recrystallized.

[0306] Structure of the exemplified compound A- 74 was confirmed Te cowpea in 1 H- NMR scan Bae spectrum and mass spectrometry scan Bae spectrum. Showing physical property data of the exemplified compound A- 74, the spectral data below.

[0307] MS (FAB) m / z: 487 (M + 1)

J H- NMR (400MHz, CDC1) :. Δ / ppm 7. 37 (dd, J = 4 7Hz, J = 8. 3Hz,

3

2H), 7. 4- 7. 5 (m, 2H), 7. 5- 7. 6 (m, 4H), 7. 7- 7. 8 (m, 4H), 7. 81 (dd, J = l. 2Hz, J = 8. 3Hz, 2H), 7. 9- 8. 0 (m, 4H), 8. 48 (d, J = 7. 8Hz, 2 H), 8. 65 (dd, J = l. 2Hz, J = 4. 6Hz, 2H)

(Synthesis of Exemplified Compound A- 60)

[0308] [of 115]

[0309] 4, 4 '- Jodobifue - Le 6. 87 g, y- carboline 6. OOG in N, mixture added in the N- Jimechiruase Toamido 50 ml, copper powder 4. 5 g, mosquitoes potassium carbonate 7. 36 g卩E was heated under reflux for 15 hours. The aqueous black port Holm added After allowing to cool, the insoluble material was removed by filtration. The organic layer was separated and the aqueous was washed with saturated brine, and concentrated under reduced pressure, and the obtained residue was subjected to silica gel chromatography photography one, was crystallized hexane in to dichloromethane Z cycloalkyl, Example Compound A - to give a 60 colorless crystals 4. 3 g.

Structure [0310] Exemplified Compound A- 60 has, IH- confirmed Te cowpea to NMR spectrum and mass spectrum. Showing physical property data of Exemplified Compound A- 60, the spectral data below.

[0311] MS (FAB) m / z: 487 (M + 1)

'H-NMR (400MHz, CDC1): δ / ppm 7. 4- 7. 4 (m, 4H), 7. 4- 7. 5 (

3

m, 4H), 7. 7- 7. 8 (m, 4H) 7. 9- 8. 0 (m, 4H), 8. 25 (d, J = 7. 8Hz, 2H), 8. 57 (d , J = 5. 6Hz, 2H), 9. 42 (s, 1H)

(Synthesis of Exemplified Compound A- 144)

[0312] [of 116]

[0313] Palladium acetate 0. 16g, tri - and tert- butylphosphine 0. 58 g was dissolved in anhydrous toluene 10 ml, was added sodium borohydride 25mg, After stirring for 10 minutes at room temperature, [delta] - carboline 2. OOG, . intermediate a3 20 g, sodium - a tert- Bed Bok Kishido 1. 37 g was dispersed in anhydrous xylene 50 ml, under a nitrogen atmosphere and stirred for 10 hours at reflux temperature. The organic layer was separated by adding cool after black port Holm and water, the organic layer was washed with water, and concentrated under reduced pressure was washed with saturated brine, exemplified resulting residue was acetic force recrystallized Compound A- colorless crystals 1. 5 g of 144.

Structure [0314] Exemplified Compound A- 144 may have been conducted under the confirmed iH-NMR spectrum and mass spectrum. Spectral data of the exemplified compound A- 144 is as follows.

[0315] MS (FAB) m / z: 647 (M + 1)

'H-NMR (400MHz, CDC1): δ / ppm 1. 80 (S, 12H), 7. 27 (S, 4H), 7

3

. 34 (dd, J = 4. 9Hz, J = 8. 3Hz, 2H), 7. 3- 7. 4 (m, 2H), 7. 4- 7. 5 (m, 1 2H), 7. 76 (dd, J = l. 3Hz, J = 8. 3Hz, 2H), 8. 45 (d, J = 7. 8Hz, 2H), 8. 6 3 (dd, J = l. 3Hz, J = 4. 9 Hz, 2H)

(Synthesis of Exemplified Compound A- 143)

[0316] [of 117]

[0317] 4, 4 '- dichloro port one 3, 3' -. Bibirijiru 0. 85 g, Jiamin bO 59 g added dibenzylidene acetone palladium 44 mg, Imidazoriumu salt 36 mg, sodium tert-butoxide 1. 09 g dimethoxy E Tan 5ml and, 24 hours heated and stirred at 80 ° C. The organic layer was separated by adding cool after black port Holm and water, the organic layer was washed with water, and concentrated under reduced pressure was washed with saturated brine, exemplified resulting residue acetate Echiruka recrystallized Compound A- colorless crystals 0. 3 g of 143.

Structure [0318] Exemplified Compound A- 143 may have been conducted under the confirmed iH-NMR spectrum and mass spectrum. It shows the spectral data of the exemplified compound A- 143 below.

[0319] MS (FAB) m / z: 639 (M + 1)

iH-NMR (400MHz, CDC1): δ / ppm 7. 46 (d, J = 5. 7Hz, 4H), 7. 6-

3

7. 7 (m, 4H), 7. 8- 7. 9 (m, 4H), 8. 67 (d, J = 5. 7Hz, 4H), 9. 51 (S, 4H) (Example Compound A- 145 synthesis of)

Synthesis of Exemplified Compound A- 143, 4, 4 'Jikuroro 3, 3' - hand of the pyridine ring of Bibirijiru was changed to benzene, 3- (2 black port phenylene Honoré) except using 4 black port pyridine in the same manner, it was synthesized exemplary compound A- 145.

Structure [0320] Exemplified Compound A- 145 may have been conducted under the confirmed iH-NMR spectrum and mass spectrum. It shows the spectral data of the exemplified compound A- 145 below.

[0321] MS (FAB) m / z: 637 (M + 1)

'H-NMR (400MHz, CDC1): 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. 3Hz, 2H), 8. 23 (d, J = 7. 8Hz, 2H), 8. 56 (d, J = 5. 3Hz, 2H), 8. 96 (S, 2H)

In addition to the synthesis example above, § The carbazole ring or its class chloroplasts ί of these compounds or, J. Chem. Soc., Perkin Trans. 1, 1505- 1510 (1999), Pol. J. Chem. , 54, 1585 (1980), (Tetrahedron

Lett. 41 (2000), can be synthesized according to the synthesis method described in 481- 484). And § The carbazole ring or its class green body that is synthesized, an aromatic ring, a heterocyclic ring, such as an alkyl group, the core, is introduced into the linking group, Ullmann coupling, coupling with Pd catalyst, Suzuki coupling, etc. It may be a known method.

[0322] Compounds according to the present invention is more preferably more preferably tool and a This is the preferred tool 450 or more is at a molecular weight force 00 or more and 600 or more, and particularly preferably a molecular weight of 800 or more. This improves the thermal stability increases the glass transition temperature, it can be a more longer life.

[0323] Next is a detailed description of the construction layers of the organic EL device of the present invention. In the present invention, while indicating preferred embodiments of the layer structure of the organic EL element hereinafter, the present invention is limited to Sarena ヽ. (I) anode Z-emitting layer Z electron transport layer Z cathode (ϋ) anode Z hole transport layer Z luminescent layer

Z electron transport layer Z cathode (m) anode Z hole transport layer Z emitting layer Z hole blocking layer Z electron transport layer Z cathode Gv) anode Z hole transport layer Z emitting layer Z hole blocking layer Z electron transport layer Z cathode buffer more Z cathode (V) anode Z anode buffer more Z hole transport layer Z emitting layer Z hole blocking layer Z electron transport layer Z cathode buffer more Z cathode

"anode"

The anode in the organic EL device, a large work function (4 eV or more) metals, alloys, is preferably used to electric conductive compound, or an electrode material mixture thereof. Specific examples of such electrode materials as this metal such as Au, Cul, indium tin O sulfoxide (ITO), SnO, include a conductive transparent material such as ZnO are. Further, IDIXO (In O- ZnO) or the like

2 2 3 Yo ヽ be used a material capable of producing a transparent conductive film in amorphous. By a method such as evaporation or spattering of the electrode material is an anode, a thin film is formed, if not desired shape Yogu or pattern accuracy by forming a pattern of requires less photolithography one method (100 mu to or higher than m), the pattern may be formed through a mask of a desired form at the time of depositing or spattering of the electrode material. When light is emitted through the anode, the sheet resistance of the transmittance as an anode was Sigma desirable to greater than 10% preferably several hundreds Omega Z b hereinafter. Further thickness also depends forces usually 10 to the material: LOOOnm, is preferably selected in the range of 10~2 OOnm.

[0324] "cathode"

On the other hand, as a cathode, a small work function (also referred to as an electron injecting metal) (4 eV or less) metal, alloy, and an electroconductive compound, or a mixture thereof is used as the electrode material. Specific examples of the electrode substance include sodium, sodium mono-potassium alloy, a magnetic Shiumu, lithium, magnesium Z copper mixtures, magnesium Z silver mixture, magnesium Z aluminum mixture, magnesium Z indium mixture, aluminum Z Sani匕 Aluminum - © beam (Al O) mixture, indium, lithium

2 3 Z aluminum mixture, and rare earth metals. Among them, a mixture of a point of an electron injection property and durability against Sani 匕等, a second metal values ​​of the electron injection metal and a work function than this is the large stable metal, such as magnesium Z silver mixture, magnesium Z aluminum mixture, Maguneshiu arm Z indium mixture, aluminum Z Sani匕 aluminum (Al O) mixture, lithium

2 3 Z aluminum mixture, and aluminum. Cathode by forming a thin film by a method such as evaporation or spattering of the electrode material can be manufactured. In addition, sheet resistance of several hundred Ω / mouth following is preferred tool thickness of the cathode is usually ΙΟηπ! ~ 5 mu m, preferably selected in the range of 50 to 200 nm. Incidentally, order to allow transmit emission is improved emission luminance advantageous if either one force transparent or translucent anode or the cathode of the organic EL element.

[0325] In addition, the metal on the cathode after forming a thickness of L~20nm, the conductive transparent material exemplified in the description of the anode by manufacturing thereon, making child a transparent or translucent cathode bets can be, both the anode and cathode by the application of this can be manufactured element having transparency.

[0326] Next, used as a constituent layer of the organic EL device of the present invention, injection layers, blocking layers, a description will be given of an electronic transportation layer or the like. [0327] "injection layer: electron injection layer, a hole injection layer"

Injection layer is provided if necessary, there is an electron injection layer and the hole injection layer, is present between the as an anode between the light-emitting layer or a hole transport layer, and a cathode and a light emitting layer or an electron transport layer Choi Te.

[0328] An injection layer, the drive voltage is lowered and the light-emitting layer provided between an electrode and an organic layer to improve luminance that, "Organic EL element and its Industrialization Front (Nov. 30, 1998 E j 'Tea - E, Inc. published) "2 Chapter 2 of" electrode material "(which is described in detail in pages 123 to 166), a hole injection layer (anode buffer more) and an electron injection layer (more cathode buffer) there is a door.

[0329] anode buffer more (hole injection layer), JP-9- 45479 discloses, 9 260 062 JP has also been described in detail in the 8-288069 discloses such, as a specific example, copper more phthalocyanine buffer typified off Taroshianin, more oxide buffer typified Sani匕 vanadium, amorphous carbon buffer further, Poria - phosphorus (Emerarudi down) and the polymer buffer using a conductive polymer such as Porichiofen more and the like and the like

[0330] cathode buffer more (electron injection layer), JP-A 6 325 871 discloses, the 9-17574, JP-are described also in detail in the 10-74586 discloses such, specifically stolons lithium Ya aluminum to further metal buffer typified, alkali metal compound buffer further represented by lithium fluoride, alkaline earth metal represented by magnesium fluoride group compound buffer further acids typified by acid arsenide aluminum I arsenide was buffer one layer, and the like. The buffer further (injection layer) depending on the extremely thin film is it is desirable tool material thickness is preferably in a range of 0. lnm~5 m.

[0331] "blocking layer: a hole blocking layer, an electron blocking layer"

Blocking layer and is provided if necessary in addition to the above you sharpen organic compound base layers constituting the thin film. For example, as described in JP-A 11 204 258 discloses, the 11 two hundred and four thousand three hundred and fifty-nine JP, and 237 pages, etc. "Organic EL element and its Industrialization Front (November 30, E j 'Tea Es Inc. issuance 1998)" and there is a hole-blocking (hole blocking) layer has.

[0332] In the broad sense the hole blocking layer is an electron transporting layer, the ability of transporting holes while having a function of transporting electrons but a very small hole blocking material, a hole while transporting electrons it is possible to improve the probability of recombination of electrons and holes by blocking.

[0333] hole blocking layer of the organic EL device of the present invention is provided adjacent to the light emitting layer.

[0334] In the present invention, the compounds according to the present invention described above as a hole blocking material of the hole blocking layer be free Yes preferable. Thus, it is possible to even higher luminous efficiency organic EL device. It is possible to even more further long life.

[0335] On the other hand, in a broad sense, the electron blocking layer is a hole transport layer, the ability to transport electrons while have a function of transporting holes is significantly less material strength, the electron while transporting holes it is possible to improve the probability of recombination of electrons and holes by thwart.

[0336] "the light-emitting layer"

Emitting layer according to the present invention, the electrode or the electron transport layer is a layer hole transport layer mosquitoes ゝ et injected come electrons and holes are recombined to emit light, the portion which emits light within the layer of the light-emitting layer even the interface between the adjacent layers also shall apply and the light-emitting layer,.

[0337] (Hosutoi 匕合 product)

The light-emitting layer of the organic EL device of the present invention, described below, Hosutoi 匕合 product and phosphorescent I 匕合 product (also referred to as a phosphorescent I 匕合 thereof) is It is preferred instrument the content is in the invention, it is preferable to use a compound according to the present invention described above as a host compound. Thus, it is possible to increase even more the luminous efficiency. Further, as Hosutoi 匕合 was good also contain the engagement Ru than a compound of compound of the present invention ヽ.

[0338] Here, you the present invention, the Hosutoi 匕合 thereof Te, phosphorescence quantum yield of the phosphorescent in Atsushi Muro (25 ° C) among the compounds contained in the light emitting layer, 0.01 compounds below and Ru are defined.

[0339] may be used in further combination plural kinds of known Hosutoi 匕合 thereof. By using a plurality of host compounds, it is possible to adjust the movement of the charge, can you to higher efficiency of the organic EL element. In addition, by use of a plurality of phosphorescent 匕合 product, it is possible to mix different emission, thereby it is possible to obtain an arbitrary emission color. Type of phosphorescent compound, is capable of white light emission by adjusting the de Ichipu amount, it can be illuminated, even application to the backlight

[0340] These known host compounds, while having a hole transport ability, electron transport ability, and prevents the longer wavelength of emission, compounds preferred is yet high Tg (glass transition temperature).

[0341] Specific examples of known Hosutoi 匕合, compounds are exemplified up that is described in the following references.

[0342] JP 2001- 257076, JP-the 2002- 308855, JP-the 2001- 313179, JP-the 2002- 319491, JP-the 2001- 357977, JP-the 2002- 334786, JP-the 2002- 8860 JP, the 2002- 334787, JP-the 2002- 15871, JP-the 2002- 334788, JP-the 2002- 43056, JP-the 2002- 334789, JP-the 2002- 75645, JP same 2002- No. 338579 publication, the 2002- 10544 5 discloses, the 2002- 343568, JP-the 2002- 141173, JP-same 2002- 352 957 discloses, the 2002- 203683, JP-the 2002- 363227, JP-the 2002- 2 31453 JP, the 2003- 3165 JP, the 2002- 234888, JP-the 2003- 2 7048 JP, the 2002- 255934, JP-the 2002- 260861, JP-the 2002- 280183, JP-same 2002- 299,060 JP, same 2002- 302516, JP same 2002 - 305083 JP, same 2002- 305084, JP same 2002- 308837 Patent Publication.

[0343] The light emitting layer may have contains a Hosutoi 匕合 having a further fluorescent maximum wavelength as Hosutoi 匕合 thereof. In this case, energy transfer from other host compound and a phosphorescent compound to a fluorescent compound, an electroluminescent as an organic EL element emitting the other Hosutoi 匕合 product force having a fluorescence maximum wavelength is also obtained. Good Mashiino as Hosutoi 匕合 having a fluorescence maximum wavelength is a high fluorescent quantum yield in a solution state. Here, the fluorescence quantum yield 1 0% or more, particularly 30% or more is preferable. The host compound having a specific fluorescence maximum wavelength, coumarin dyes, pyran based dyes, Shianin dyes, Kurokoniumu dyes, disk Ariumu dyes, O Kiso Benz anthracene dyes, Furuoresein based dyes, rhodamine based dyes, pyrylium system dye, a perylene dye, stilbene dyes, Porichiofen-colored arsenide. Fluorescence quantum yield, the fourth edition 362 pp Bunko II Jikken Kagaku Koza 7 (1992) published by Maruzen may be measured by the method described in.

[0344] (phosphorescent compound)

Materials used in the light-emitting layer (hereinafter, referred to as light emitting material) Examples of the at the same time containing the above host compound, preferably contains a phosphorescent I 匕合 thereof. Thus, the more the luminous efficiency higher!, May be an organic EL element.

[0345] phosphorescent I 匕合 product according to the present invention, Ri compound der the emission of triplet force also is observed, a compound of phosphorescence at room temperature (25 ° C), phosphorescence quantum yield rate is a 0.01 or more compounds in 25 ° C. Phosphorescent quantum yield is preferably 0.1 or more. The phosphorescent quantum yield, Bunko II, page 398 in 4th Ed. 7 (1992) published by Maruzen may be measured by the method described in. Although phosphorescence quantum yield in a solution kills measured using a variety of solvents, phosphorescent I 匕合 product used in the present invention, the upper Symbol phosphorescence quantum yield is achieved using any of the appropriate solvent it may be Re.

[0346] emission of phosphorescent I 匕合 was obtained in two types in principle, the excited state of the one in which recombination of a carrier occurs on the host Suti 匕合 product carriers are transported Hosutoi 匕合 product There was generated, energy transfer type refers to the energy and obtaining light emission of the phosphorescent I 匕合 product force by moving the phosphorescent I 匕合 thereof and one phosphorescent 匕合 product carrier trap next, the light emission recombination occurs phosphorescent I 匕合 product strength of the carrier in phosphorescent compound Butsujo is key Yariatorappu type being obtained, in any case, the energy of the excited state of the phosphorescent compound it is a condition lower than the energy of the excited state of Hosutoi 匕合 thereof.

[0347] phosphorescent I 匕合 product can be used by appropriately selection from known to be used in the light emitting layer of the organic EL element.

[0348] As a phosphorescent I 匕合 product to be 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, Osumi © beam compound, or a platinum compound (a platinum complex compound), a rare earth complex, among others the most preferred, is given to iridium compounds.

[0349] Hereinafter, specific examples of the phosphorescent compounds, the present invention is not limited thereto. These compounds are, for example, Inorg. Chem. 40 Certificates can be synthesized by the method described in 1704-1711.

[0350] [of 118] lr-2

[0351] [of 119]

lr-11 ir-12

120]

[0353] [of 121]

Pd-1 Pd-2 Pd-3

[0354] [of 122]

[0356] [of 124]

[0357] In the present invention, selecting a center metal, a ligand, ligand substituents such in principle the Nag particular limitation is imposed as a phosphorescence emission maximum wavelength of the phosphorescent 匕合 product Although the emission wavelength obtained by may be varied, preferably have a maximum wavelength of phosphorescence phosphorescence emission wavelength within 3 80~480Nm phosphorescent I 匕合 product! /,. Such an organic EL element of blue phosphorescent emission in the organic EL element of white phosphorescent, leaves in the Rukoto enhanced more luminous efficiency.

[0358] Color of light emitted by the organic EL element or a compound according to the present invention of the present invention, "Shinpen color science Nono Handbook" (Color Science Association of Japan, ed., University of Tokyo Press, 1985) of the 108 pages of Figure 4.16 smell Te, spectroradiometer CS - is determined by the color when the results of measurement with - (manufactured by force Minolta sensing Inc. co) fitted to C IE chromaticity coordinates 1000.

[0359] The light-emitting layer above compounds, for example, vacuum deposition, spin coating, casting, LB method, can be formed by a film by a known thin film I 匕法 such I ink jet method. The film thickness of the light-emitting layer is not particularly limited, but is usually 5ηπ! ~ 5 mu m, preferably selected in the range of 5 to 200 nm. The light-emitting layer even to these phosphorescent compound or the host compound may be a single layer structure is also the force of one or more or of plural layers comprising the same composition or different compositions, .

[0360] "hole transport layer"

The hole-transporting layer becomes the hole transport material force having the function of transporting holes, a hole injection layer in a broad sense, an electron blocking layer are included in the hole transport layer. The hole transport layer may be a single layer or plural layers.

[0361] As the hole transporting material, a hole injection or transport, electron barrier property! / A shall which have a Zureka, organic, may be any of inorganic substance. For example, Toriazoru derivatives, Okisajiazoru derivatives, imidazole derivatives, polyarylalkane derivatives, Vila gelsolin derivatives and pyrazolone derivatives, off - Renjiamin derivatives, Ariruamin induction body, Amino-substituted chalcone derivatives, Okisazoru derivatives, styryl anthracene derivatives, Furuorenon derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, Aniri emission type copolymer, or a conductive polymer oligomer, especially Chio Fen oligomer is exemplified et be.

[0362] Power Borufuirini 匕合 product can be used those described above as the hole transporting material, an aromatic tertiary Amin compounds and styrylamine compounds, the use of aromatic tertiary Amini spoon compounds particularly preferably,.

[0363] Representative examples of aromatic tertiary Amini 匕合 product and Suchiriruamini 匕合 thereof, N, N, N ', N' - tetraphenyl one 4, 4 '- Jiaminofue - le; N, N' - Jifue - Le one N, N '- bis (3-Mechirufue - Le) one [1, 1' - Bifue - le] one 4, 4 '- Jiamin (TPD); 2, 2-bis (4-di-one p Toriruaminofue - Le) propane; 1,1-bis (4-di-one p tri Ruaminofue - Le) cyclohexane; N, N, N ', N' - tetramethyl one p-tolyl one 4, 4 '- Jiaminobifue - le; 1, 1 bis (4-di-one p Toriruaminofue - Le) 4 Hue - hexane Rushiku port; bis (4 - Jimechiruamino 2 Mechirufue - Le) phenylmethane, bis (4 - di -p Toriruaminofue - Le) Hue - Rumetan; N, N ' - Jifue - Le one N, N '- di (4-Metokishifue - Le) 4, 4' over diamino Biff enyl; N, N, N ', N' - Tetorafue - le -4, 4 'Jiaminojifue - ethers; 4, 4 'bis (Jifue - Ruamino) Kuo one drift E - le; N, N, N-tri (p-tolyl) Amin; 4- (di - p Toriruamino) - 4' - [4- (di - p Toriruamino) styryl] stilbene; 4-N, N Jifue - Ruamino - (2 Jifue - ruby ​​- Le) benzene; 3-methoxy one 4 '- N, N-diphenyl-amino stilbene; N Hue - carbazole, more having U.S. Patent No. 5, 061, 569 Pat intramolecular two fused aromatic rings disclosed in, for example, 4, 4 'bis [N-(1 over naphthyl) N Hue - Ruamino ] Bifuwe - Le (NPD), bird whistle are placing serial in JP-a-4 308 688 - 4 Rua Min unit is connected to three starburst, 4 ', a "- tris [^ -? (3 - Mechirufue - Le) N Hue - Ruamino] bird whistle - Ruamin (MTD ATA) and the like.

[0364] Furthermore, it these materials are introduced in a polymer chain, or may be used a polymer having the material as the polymer main chain. Further, p-type - Si, p-type - inorganic compounds such as SiC can be used hole injection material, a hole transport material.

[0365] The hole transport layer is the hole transport material, for example, vacuum deposition, spin coating, cast method, a printing method including inkjet method, by a known method LB method, reducing the thickness I spoon it can be more formed. There is no particular limitation on the thickness of the hole transporting layer is usually about 5nm~5 μ m, preferably from 5 to 200 nm. The hole transport layer may have a single layer structure is also one or more forces of the material.

[0366] "electron transport layer"

The electron transport layer made material force has a function of transporting electrons, an electron injection layer in a broad sense, a hole blocking layer are included in an electron transport layer. Electron-transporting layer leaves in this transgression providing a single layer or plural layers.

[0367] Conventionally, an electron-transporting layer of a single layer, and if a plurality of layers as an electron transporting material for the electron transport layer in contact next to the cathode side of the light-emitting layer (also serving as a hole blocking material), Yin it can be used to select an arbitrary one from known compounds the electrons injected from the electrode as Yogu the material have a function of transmitting the light emitting layer, for example, - DOO port substituted fluorene derivatives, Jifuwe - Rukinon derivatives, Chio pyran dioxide derivatives, force carbodiimide, deflection distyrylpyrazine derivatives, anthraquinodimethane and anthrone-induced body, Okisajiazoru derivatives. Moreover, Te contact, in the Okisajiazoru derivative, thiadiazole derivative conductor which is formed by substituting the oxygen atom of Okisajiazoru ring sulfur atom, also quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group are usable as the electron transporting material. Furthermore these materials are introduced in a polymer chain, or these materials can also be used polymeric materials whose main chain of the polymer.

[0368] The metal complexes of 8-hydroxyquinoline derivatives, such as tris (8-hydroxyquinoline) aluminum - © beam (Alq), tris (5, 7-dichloro-one 8-quinolinol) aluminum, tris (5, 7-jib Romo one 8-hydroxyquinoline) aluminum, tris (2-methyl 8 - quinolinol) aluminum - © beam, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Zn q), etc., and the central metal of these metal complexes but in, Mg, Cu, Ca, Sn, even Ga or Pb, can be used as the electron transporting material. Other, even those Metarufu Lee or metal phthalocyanine, or their ends are substituted with an alkyl group Ya sulfonic acid group or the like, can be preferably used as the electron transporting material. Also, distyryl Vila derivative exemplified as a material for emitting light layer, be employed as the electron transporting material, a hole injection layer, as a hole transport layer, n-type - Si, n-type - SiC, etc. can also inorganic semiconductors used as the electron transporting material.

[0369] The electron transport layer and the electron transporting material, for example, vacuum deposition, spin coating, cast method, a printing method including inkjet method, by a known method LB method, and more to a thin film spoon it can be formed. There is no particular limitation on the thickness of the electron transporting layer is usually about 5nm~5 μ m, preferably from 5 to 200 nm. Be electron-transporting layer was one or the said material a single layer structure also forces two or more kinds.

[0370] "substrate"

The organic EL device of the present invention is preferably formed on the substrate.

[0371] substrates can be used in the organic EL device of the present invention (hereinafter, the substrate, the substrate refers to both the support and the like) as a glass, was particularly limited Coati of the type of plastic, intended transparent not particularly limited as long, but as preferred substrates for use, for example, may be mentioned glass, quartz, light-transmissive 榭脂 film. Particularly preferred substrate is a 榭脂 film capable of providing flexibility to the organic EL element.

[0372] The 榭脂 film, e.g., polyethylene terephthalate (PET), polyethylene Na phthalate (PEN), polyether sulfone (PES), polyetherimide, polyether ether ketone, Porifue - Rensurufuido, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP) Hitoshiryoku also films. On the surface of the 榭脂 film, inorganic, the film or hybrid coating both the organic matter is formed, even if,.

[0373] external extraction efficiency of light emission at room temperature of the organic EL device of the present invention this and the force transducer Mashiku 1% or more, more preferably 5% or more. Here, a number of electrons X 100 that was run on external extraction quantum efficiency (%) = number of photons Z organic EL device emitting organic EL device the outside.

[0374] Further, even in combination with hue improving filter Chief of the color filter first class, it may also be used in combination a color conversion filter for converting the multi-color emission color from an organic EL device using the phosphor ヽ. In the case of using a color conversion filter, lambda max of light emission of the organic EL element is preferably 480nm hereinafter.

[0375] "method for manufacturing the organic EL device"

As an example of a method for manufacturing an organic EL device of the present invention will be described with the anode / hole injection layer / hole transport layer Z emitting layer Z electron transport layer Z electron injection layer Z preparation method of the organic EL element composed of the cathode.

[0376] First suitable substrate desired electrode material on, for example, anode material force becomes thin film 1 mu m or less, more formed preferably to have a thickness of 10 to 200 nm, vapor deposition, sputtering or some other method It is to produce an anode. Next, a hole injection layer is an organic EL element material on the hole transporting layer, light emitting layer, electron transporting layer, an electron injection layer to form an organic compound thin film of the hole blocking layer.

[0377] As a method of a thin film I spoon of the organic compound thin film, a vapor deposition method as described above, a wet process

(Spin coating, casting, inkjet method, a printing method), a uniform film can viewpoint of hardly generated resulting et been Ya immediately and pinholes, a vacuum vapor deposition method, a spin coating method, an inkjet method , printing method is particularly preferred. But it may also be further applied to different film-forming method for each layer. When employing the vapor deposition film, the depositing conditions thereof are varied according to kinds of materials used, generally boat temperature 50 to 450 ° C, vacuum degree of 10- 6 to 10-2 Pa, deposition rate 0.01 ~50nmZ seconds, substrate temperature - 50 to 300. C, thickness 0. lnm~5 μ m, preferably Shi desired be appropriately selected in the range of 5~2 OOnm! / ,.

[0378] After formation of these layers, a thin film becomes cathode material forces thereon, as preferably less 1 mu m make a layer thickness in the range of 5 0Nm~200nm, for example, by a method such as vapor deposition or sputtering to form the desired organic EL device can be obtained by providing the cathode. Preparation of the organic EL element, but may be subjected to film formation method different extraction halfway preferably made from a single consistently positive hole injection layer by vacuuming up the cathode. At that time, the required to be carried out under dry 燥不 active gas atmosphere.

[0379] multicolor display apparatus of the present invention is a shadow mask is provided only at the light-emitting layer formation, since the other layers are common and not required putter Jung such shadow mask deposition method, a casting method, a spin coating law, an inkjet method, the film can be formed by a printing method or the like. Emitting layer only putter - When performing ranging, but are not limited to the method, preferably an evaporation method, an inkjet method, printing method. In the case of using a vapor deposition method, putter Jung using a shadow mask it is preferred.

[0380] Further, reversing the preparation order, a cathode, an electron injection layer, an electron transport layer, light emitting layer, a hole transport layer, a hole injection layer, it is also possible to prepare the order of the anode. Such multi-color display device obtained by, in the case of applying the direct-current voltage, the anode +, is applied voltage of approximately 2~40V the cathode as one polarity, light emission occurs. The alternating current voltage may be applied. Name your, the waveform of the alternating current to be applied may be arbitrary.

[0381] Display device of the present invention can be used as a display device, a display, or various light emission sources. The display device or the display, blue, red, by using 3 kinds of organic EL element of green light emission, it is possible to display full color.

[0382] Display devices, as the display television, Roh Sokon, thermopile devices, AV equipment, character broadcast display and an information display used in a car. In particular it may be both an active matrix method in a simple matrix (passive matrix) method driving dynamic method when also used as a display device for Yogu video for playback by using as a display device for reproducing still images and moving images.

[0383] Lighting device of the present invention is lighting for home, car lighting, backlight of a watch or a liquid crystal, a panel advertisement, traffic lights, optical storage media source, the electrophotographic copying machine the light source, an optical communication processor light source, a light source of the sensor or the like can be mentioned but not limited thereto.

[0384] Further, it may be an organic EL element having a resonator structure into the organic EL element of the present invention. The purpose of such an organic EL element having a resonator structure, a light source of an optical storage medium, an electrophotographic copying machine of the light source for an optical communication device of the light source, the power source or the like of the optical sensor and the like limited to not. Further, by the laser oscillation, Choi and used in the above applications.

[0385] The organic EL device of the present invention, visibility may be used as one type of lamp, such as a illuminating lamp or a light source for exposure, and the type of project Chillon apparatus for projecting an image, still images and moving images directly it may be used as the type of the display device (display) for. Drive system when used as a display device for reproducing a moving image may be both an active matrix method in a simple matrix (passive matrix) method. Or, by using the onset Ming organic EL element 3 or more having different emission colors, it is possible to produce a full color display device. Or, one color emission colors, for example, white light emission, and the BGR by have use a color filter, it is possible to full color. Furthermore the luminescent color of the organic EL, it is possible to full color is converted into another color with the color conversion filter, in which case, lambda max of the organic EL emission is preferably 480nm or less.

[0386] The organic EL element force will also be described below with reference to the drawings an example of a display device constituted.

[0387] FIG. 1 is a schematic diagram showing an example of an organic EL device power composed display device. For displaying image information due to light emission from the organic EL element, for example, it is a schematic view of a display such as a mobile phone.

[0388] Display 1, the display unit A having a plurality of pixels, based on the image information! /, Te becomes controller B Hitoshiryoku performing image scanning of the display portion A.

[0389] The control unit B is connected to the display unit A electrically, transmits a scanning signal and an image data signal on the basis of the images information from outside the plurality of pixels, image elements of each scanning line by the scanning signal There displays the image information on the display unit a performs image scanning which emits light according to image data signals.

[0390] FIG. 2 is a schematic drawing of a display section A.

[0391] Display unit A on the substrate having a wiring portion including a plurality of scanning lines 5 and the data lines 6, and a plurality of picture element 3 and the like. Given below a description of the main members of the display portion A. In Figure 2, the emitted light of the picture element 3, illustrates a case taken out in the direction of an arrow, Ru. [0392] wiring of the scanning lines 5 and plural data lines 6 each made of a conductive material, scanning lines 5 and the data lines 6 being crossed with each other at a right angle, and connected with the pixels 3 at the crossed points It is (not shown in detail).

[0393] pixels 3, when the scanning signal is applied from the scanning lines 5, receive the data signal from the data lines 6, and emit light corresponding to received image data. Pixel color emitting red region, pixels in the green region, the pixels of the blue region, as appropriate, side by side on the same substrate, it is possible full color one appears.

[0394] Next, an emission process of pixels will be explained.

[0395] FIG. 3 is a schematic diagram of a pixel.

[0396] pixels, the organic EL element 10, a switching transistor 11, driving transistor 12, and a capacitor 13, and the like. As the organic EL element 10 to a plurality of pixels, red, green, an organic EL element of blue light - emitting, these full-color display can line Ukoto by juxtaposing on the same substrate.

[0397] In FIG. 3, the image data signal is applied the control unit B force even through the data line 6 to the drain of the switching transistor 11. When the scanning signal to the gate of Suitchin grayed transistor 11 is applied via the control unit B power scanning line 5, the switching transistor 11 is switched on, the image data signal applied to the drain and the capacitor 13 drive transients It is transmitted to the gate of the static 12.

[0398] The transmission of the image data signals, while being charging according to the potential of the capacitor 13 is image data signals, the driving transistor 12 is switched on. The drive transistor 12 is connected drain to the power supply line 7, the source is connected to the electrode of the organic EL element 10, the organic EL from the power supply line 7 in response to the potential of the image data signal applied to the gate Ichito current is supplied to the element 10.

[0399] progressive scanning signal by the scanning of the control unit B is to the next scanning line 5, the driving of the switching transistors 11 are turned off. However, since the drive of the switching transistor 11 is capacitor 13 is also turned off to hold the charged potential of image data signal, driving of the driving transistor 12 is kept turned on, the application of the next scanning signal line emission of the organic EL element 1 0 is continued until cracking. When the next scanning signal by sequential scanning is applied, the driving transistor 12 organic EL element 10 emits light in response to the potential of the next image data signal synchronized with the scanning signal.

[0400] That is, light emission of the organic EL element 10, the organic EL element 10 of each of the plurality of pixels, provided with a switching transistor 11 and driving transistor 12 which is an active element, multiple pixels 3 each organic EL perform the light emission of the element 10, Ru. Call such a light emitting method and § active matrix method, Ru.

[0401] Here, light emission of the organic EL element 10, by also emitting a plurality gradations according to image signal data having plural gradation potentials, and a predetermined amount of light emission by the binary image data signal on, even old off! /,.

[0402] The holding of the electric potential of the capacitor 13, it is maintained continuously until the next application of the scanning signal, and, be discharged immediately before the next scanning signal is applied Yo,.

[0403] Contact with the present invention, Te is not limited to the active matrix method as described above, it may be the light emission driving a passive matrix scheme for emitting the organic EL element in accordance with the data signal only when the scan signal is scanned.

[0404] FIG. 4 is a schematic drawing of a display employing a passive matrix method. 4, a plurality of image data lines 6 and the scanning line 5 of several are provided on opposite sides of the pixel 3 in a lattice pattern.

[0405] sequentially when the scanning signal of the scanning line 5 by the scanning is applied, to connect to the applied scanning lines 5, Ru pixels 3 emit light in response to image data signals. Roh Tsu Shiv matrix no active elements picture element 3 in a manner, which reduces manufacturing cost.

[0406] Organic EL materials according to the present invention, also as a lighting device, can be applied to an organic EL device which emits light of substantially white. At the same time it emits light a plurality of emission colors by a plurality of light emitting material to obtain white light by mixing colors. As a combination of the plurality of emission colors, blue, green, may be one which contains three light-emitting maximum wavelength of the blue of the three primary colors, blue and yellow, blue green and the like two utilizing complementary colors orange emission maximum wavelength may be one containing.

[0407] Also, the combination of the luminescent materials to obtain a plurality of emission colors, a material (light emitting dopant) for emitting a plurality of phosphorescent or fluorescent, a combination plurality, a light-emitting material that emits fluorescence or phosphorescence although a combination of a dye material which emits light from the light emitting material as the excitation light, is shifted even by! / ヽ, in the white organic elect port Rumine' sensing element according to the present invention, a plurality combining scheme emissive dopant preferable.

[0408] The layer structure of the organic-elect opening device as to obtain a plurality of emission colors, the multiple light-emitting dopant, a method for more present in one light-emitting layer, have a plurality of light emitting layers, the light emitting method for each occurrence emission wavelength different dopants in the layer, and the like method of forming a micro-pixel emitting a different wavelength in a matrix.

[0409] In the white organic elect port luminescent element according to the present invention, during film made necessary putter with a metal mask or an ink-jet printing method - may be subjected to ring. Also, the ring, - also, and, the elements all layers putter to okay to ring, and patterning the electrode and the light-emitting layer - case, only the electrode pattern for packaging - putter.

[0410] particularly limited nag for example as a light emitting material used for a light-emitting layer, if put that Bruno backlight to the liquid crystal display device, CF (color filter) to match the wavelength range corresponding to the characteristics, according to the present invention ! if whitened combination optionally selected from platinum complexes, also known light emitting material.

[0411] Thus, light-emitting organic EL device of the present invention that white light emission, the display device, in addition to Dace play, various light emitting sources, a lighting device, home lighting, interior lighting, also as an exposure light source one type of lamp, also Bruno backlight of a liquid crystal display device, used in useful to a display device.

[0412] Other, backlight such as a watch, billboards, traffic lights, light sources, such as an optical storage medium, an electronic photograph copiers source for an optical communication device of the light source, a light source such as a light sensor, more 必 the display device general household appliances such as a principal include a wide range of applications.

Example

[0413] Example 1

"Fabrication of organic EL element 1-1"

Substrate and ITO was 150nm deposited on glass as an anode (NH Techno Glass: NA- 45) after the putter Jung, ultrasound transparent substrate having the ITO transparent electrode in iso- propyl alcohol and cLEANING, dried with dry nitrogen gas, to UV-ozone cleaning for 5 minutes rows ivy o [0414] the transparent supporting substrate was fixed on a substrate holder of a vacuum deposition apparatus available on the market, whereas, five tantalum resistance the 卩熱 boat, a-NPD, CBP, Ir 12, BCP, and Alq are

3 put, was attached to a vacuum vapor deposition apparatus (a first vacuum chamber).

[0415] [of 125]

CBP

[0416] Further, lithium fluoride tantalum resistance heating boat, placed respectively aluminum to tungsten resistive heating baud bets, attached to a second vacuum chamber of a vacuum deposition apparatus.

[0417] First, after the vacuum of the first vacuum chamber to 4 X 10- 4 Pa, and heated by supplying an electric current to the baud preparative containing the a-NPD, deposition rate 0. 1~0. 2nmZ seconds in deposition to a film thickness 25nm thick transparent supporting substrate, a hole injecting Z transporting layer.

[0418] In addition, the deposition rate of CBP of containing said heating boat and Ir 12 of entering the boat independently conductible to are CBP and the light emitting dopant which is a light-emitting host Ir- 12 100: 7 that Do to adjusted deposition to a layer thickness of 30nm as, which a light-emitting layer.

[0419] Next, and heated by supplying an electric current to the boat containing BCP, form a hole blocking layer of deposition rate from 0.1 to 0. Thickness 10nm with 2n mZ seconds. Moreover, the heating boat carrying Alq

3

Energized by heating, an electron transporting layer having a thickness of 40nm at a deposition rate of 0. 1~0. 2nmZ seconds

[0420] Next, after transferring film to an element in the second vacuum chamber while the vacuum to the electron transport layer as, as stainless steel rectangular perforated mask is placed on the electron transport layer installed from the outside of the apparatus remote control to.

[0421] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, evaporation Chakusokudo 0. 01-0. 02nmZ sec more cathode buffer layer thickness 0. 5 nm by supplying an electric current to the boat lithium fluoride-containing the provided, then § Lumi - by energizing the NyuTsuta boat © beam at a deposition rate. 1 to 2NmZ seconds with a cathode having a film thickness 150 nm, to manufacture an organic EL element 1-1.

[0422] "Preparation of Organic EL element 1 2-1 20"

Preparation In the preparation of the organic EL element 1 1, the light emitting dopant as described in Table 1, light emission host, except that the hole blocking material in the same manner, the organic EL device 1 2~1- 20 did.

[0423] The obtained organic EL device 1 1 to 1 20 Nitsu, Te was evaluated as follows.

[0424] "external extraction quantum efficiency"

The organic EL element 1 1 to 1 20 room temperature (about 23~25 ° C), 2. performs lighting by under constant current conditions 5mAZcm 2, measuring the lighting start immediately after the emission luminance (L) [cdZm 2] by, to calculate the external extraction quantum efficiency (r?). Here, measurement of the emission intensity was used CS- 1000 (manufactured by Minolta).

[0425] In addition, the external extraction quantum efficiency was represented by a relative value when the organic EL element 1 1 and 100.

[0426] "emission lifetime"

At room temperature the organic EL element 1-1 1 20, 2. performs continuous lighting by constant current conditions 5MAZcm 2, was measured the time required to becomes half of the initial luminance (tau Zeta). Or

1 2

Was, emission lifetime is expressed by a relative value when the organic EL element 1-1 and 100.

Table 1 shows the [0427] results obtained.

[0428] [Table 1] Organic EL device hole blocking external extraction

Emitting host emitting dopant Remarks Mo. material quantum efficiency (tau

1 - 1 CBP lr-12 BCP 100 easy Comparative Example

1 one 2 CBP lr-11 BCP 102 103 Comparative Example

1 -3 CBP 2 BC P 126 198 the invention

1 - 4 CBP 3 BC P 124 205 the invention

1 one 5 CBP 14 BCP 125 193 the invention

1 one 6 CBP 30 BCP 123 195 the invention

1 one 7 CP 47 BCP 124 203 the invention

1 - 8 CBP 50 BCP 125 198 the invention

1 one 9 ACZ 1 43 BCP 133 217 the invention

1 one 10 ACZ 1 44 BCP 136 221 the invention

1 -11 ACZ 2 49 BCP 134 232 the invention

1 -12 ACZ 2 53 BC P 135 235 the invention

1 one CBP 57 ACZ 1 142 246 the invention

1 -14 CBP 63 ACZ 2 141 248 the invention

1 -15 CBP 87 BCP 120 191 the invention

1 -16 CBP 89 BCP 121 185 the invention

1 one] 7 ACZ 1 103 BCP! 31 209 the present invention

1 one 18 ACZ 2 116 BCP 133 210 the invention

1 one 19 CBP 118 ACZ 1 HO 234 invention

1 one 20 CBP 120 ACZ 2 141 231 the present invention of 126]

ACZ1

From Table 1, the organic EL element manufactured using the metal complexes according to the present invention, compared with the organic EL device of Comparative, Ru apparent der to be able to achieve longer life of the high luminous efficiency and emission lifetime.

[0431] By combining a carboline derivative or derivative conductor having a cyclic structure in which at least one carbon atom of a hydrocarbon ring constituting a carboline ring of the carboline derivatives are further substituted at the nitrogen atom in the light-emitting layer, by using a derivative having a cyclic structure in which at least one carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives or the carboline induced body is further substituted with a nitrogen atom to the hole blocking layer, and La It was observed improvement in the effect according to the present invention.

[0432] Example 2

"Preparation of a full-color display device"

(Preparation of blue light emitting element)

Use an organic EL device 1 6 of Example 1 as a blue light emitting element it was.

[0433] (Preparation of green light emitting element)

In the organic EL device 1 6 of Example 1 was use, the green light emitting element Ir- 1 as a green-emitting dopants.

[0434] (Preparation of red light-emitting element)

Contact to the organic EL device 1 6 of Example 1, Te, and a red light emitting device using Ir 9 as a red emitting dopant.

[0435] prepared in the above, each red, green, and juxtaposing blue light emitting organic EL element on the same substrate, to produce an active matrix type full color display apparatus having a configuration as described in Figure 1, in Figure 2 showed only schematic drawing of a display section a of the display device manufactured. That is, on the same substrate, a wiring section containing plural scanning lines 5 and plural data lines 6, a plurality of pixels 3 juxtaposed (the color of light emission pixels in the red area, the pixels of the green region, blue region of the pixel, etc.) has become the wiring portion of the run 查線 5 and plural data lines 6 from the respective conductive material, the lines 5 and the lines 6 being crossed with each other at a right angle, and connected with the pixels 3 at the crossed points (not shown in detail). Wherein the plurality of pixels 3, the organic EL elements corresponding to the respective emission colors are driven by an active matrix scheme, each switch ing transistor and the driving transistor is provided an active element, the scanning signal from the scanning line 5 is applied When receiving the image data signal from the data lines 6, and emit light corresponding to the received image data. Each red In this way, green, by appropriately, to juxtapose the pixels of the blue, to produce a full-color display device.

[0436] By driving the full color display device has a luminance higher ingredients high durability, and a component force that sharp full-color video display can be obtained ivy.

[0437] Example 3

"Preparation of a full-color display device"

Per cent in the production of blue light-emitting device of Example 2 Te, and except that the organic EL element 1 6 to the organic EL element 1 8 in the same manner as in Example 2 to produce a full color display device.

[0438] By driving the full color display device has a luminance higher ingredients high durability, and a component force that sharp full-color video display can be obtained ivy.

[0439] Example 4

"Preparation of a full-color display device"

Per cent in the production of blue light-emitting device of Example 2 Te, and except that the organic EL element 1 6 to the organic EL element 1 1 3 in the same manner as in Example 2 to produce a full color display device.

[0440] By driving the full color display device has a luminance higher ingredients high durability, and a component force that sharp full-color video display can be obtained ivy.

[0441] Example 5

"Preparation of a full-color display device"

Per cent in the production of blue light-emitting device of Example 2 Te, and except that the organic EL element 1 6 to the organic EL element 1 1 4 in the same manner as in Example 2 to produce a full color display device.

[0442] By driving the full color display device has a luminance higher ingredients high durability, and a component force that sharp full-color video display can be obtained ivy.

[0443] Example 6

"Preparation of white light emitting element and a white illumination device"

Implementing the transparent electrode substrate of the electrode of Example 1 was putter Jung to 20 mm X 20 mm, and a film thereon of alpha-NPD in the same manner as the actual Example 1 as a hole injecting / transporting layer with a thickness of 25 nm, further, and compound 44 of the present invention which is the heating boat and CBP with emission dopant which is a light-emitting host energized compound 44 of containing boat and Ir 9 of entering a port was the boat independently of the present invention containing the CBP Ir- deposition rate of 9 100: 5: adjusted to 0.6 was deposited to a thickness of the film thickness 30η m, provided with a luminescent layer.

[0444] Tsu, in, form a hole blocking layer and lOnm film forming of BCP. In addition, a film of Alq in 40nm

3

And an electron transporting layer.

[0445] Next, in the same manner as in Example 1, was placed a substantially square perforated mask having the same shape as the stainless steel of the transparent electrode on the electron injection layer, lithium fluoride 0. 5 nm, and a cathode as a single layer cathode buffer aluminum 150nm was deposited film forming as.

[0446] The non-light emitting surface of the organic EL device was ,, illumination device covered with a glass case. Lighting device could be used and child as a thin lighting device that emits long white light emission efficiency of high emission life. Figure 5 is a schematic view of the lighting device, FIG. 6 is a sectional view of the lighting device. Cover the organic EL element 101 in the glass cover 102. 105 106 organic EL layer at the cathode, 107 is a glass substrate with a transparent electrode. Note the glass cover 102 is filled nitrogen gas 108, Tomizuzai 109 is provided.

[0447] Example 7

"Preparation of white light emitting element and a white illumination device"

In the preparation of the white light emitting device of Example 6, except for changing the compound 44 of the present invention 47 to produce a white illumination device in the same manner as in Example 6.

[0448] almost white light obtained was energized the illumination device, can be used as a lighting device component force ivy.

[0449] Example 8

"Preparation of white light emitting element and a white illumination device"

In the preparation of the white light emitting device of Example 6, except for changing the compound 44 of the present invention 49 to produce a white illumination device in the same manner as in Example 6.

[0450] almost white light obtained was energized the illumination device, can be used as a lighting device component force ivy.

[0451] Example 9

"Preparation of white light emitting element and a white illumination device according to a coating method"

Using a DC power source to 25mm X 25mm X O. 5mm glass support substrate of, to form an anode of indium Suzusani 匕物 (ITO, indium Ζ tin = 95Zeta5 molar ratio) Te in the sputtering method (Thickness 200 nm). The surface resistance of the anode was 10 Omega b. A polyethylene Bulle carbazolenevinylene Lumpur (hole transporting binder polymer) / compound 44 (blue luminescent ortho-metalated complex) of the present invention Ζ tris (2-Hue - Rubirijin) iridium complex (green luminescent ortho metalated complex : Ir- 1) Z bis (2-Benzochiofen [b] - 2-Irupirijin) § cetyl § Seto inert iridium complex (red luminescent Orutometarui 匕錯 body: Ir- 9) / 2- (4 Bifue - Lil) 5- ( 4 t Buchirufue - Le) 1, 3, 4-O hexa di § tetrazole (electron transporting material) = 200Z2Z 5/2/50 dissolved dichloroethane solution (mass ratio) was applied by a spin one data one of 100Ita m to obtain a light-emitting layer. The mask pattern Jung on the organic compound layer was placed (emission area mask to be 5 mm X 5mm), aluminum 150nm deposited as fluoride lithium © arm 0. 5 nm, and a cathode as a single layer cathode buffer in the deposition apparatus It provided with a cathode with. The anode was fabricated light-emitting element, respectively from the negative electrode out of aluminum leads. The element was placed in Gros blanking box purged with nitrogen gas, a glass sealing vessel in UV-curable adhesives (Nagase Ciba, XNR5493) to produce a lighting device sealed using.

[0452] almost white light obtained was energized the illumination device, can be used as a lighting device component force ivy.

[0453] Example 10

"Preparation of white light emitting element and a white illumination device according to a coating method"

In the preparation of the white light emitting device of Example 9, except for changing the compound 44 of the present invention 53 to produce a white illumination device in the same manner as in Example 9.

[0454] almost white light obtained was energized the illumination device, can be used as a lighting device component force ivy.

[0455] Example 11

"Preparation of white light emitting element and a white illumination device according to a coating method"

In the preparation of the white light emitting device of Example 9, except that the compound 44 of the present invention was changed to 118 to produce a white illumination device in the same manner as in Example 9.

[0456] almost white light obtained was energized the illumination device, can be used as a lighting device component force ivy.

[0457] Example 12 "Preparation of white light emitting element and a white illumination device according to a coating method"

Using a DC power source to 25mm X 25mm X O. 5mm glass support substrate of, to form an anode of indium Suzusani 匕物 (ITO, indium Ζ tin = 95Zeta5 molar ratio) Te in the sputtering method (Thickness 200 nm). The surface resistance of the anode was 10 Omega b. A polyethylene Bulle carbazolenevinylene Lumpur (hole transporting binder polymer) ZACZ1 (hole transport control material) Z Compound 57 (blue emitting Orutometarui 匕錯 body) of the present invention Z tris (2 Hue - Rubirijin) iridium complex ( green luminescent ortho metalated complex: Ir 1) Z bis (2 Benzochiofen [b] - 2-Iru pyridine) Asechiruasetona preparative iridium complex (red luminescent Orutometarui 匕錯 body: Ir- 9) 72- (4 Bife - Lil) over 5- (4 1; Buchirufe - Le) -1, 3, 4 Okisajiazo Le (electron transporting material) = 150/50/2/5/2/50 dichloroethane solvent solution obtained by dissolving (by weight) a spin - data - in applying, to obtain a light-emitting layer of LOOnm. The path data Jung the mask on the organic compound layer was placed (emission area mask to be 5 mm X 5 mm), and depositing aluminum 150nm as lithium fluoride 0. 5 nm, and a cathode as a single layer cathode buffer in the deposition apparatus It provided with a cathode. Anode, creating the light emission element out each of aluminum lead from the cathode. The the element put in a glove box purged with nitrogen gas, an ultraviolet curing adhesive with a glass sealing container (Nagase Ciba, XNR5493) to produce a lighting device sealed using.

[0458] almost white light obtained was energized the illumination device, can be used as a lighting device component force ivy.

[0459] Example 13

"Preparation of white light emitting element and a white illumination device"

In the preparation of the white light emitting device of Example 12, to prepare a white illumination device except that the compound 57 of the present invention was changed to 61 in the same manner as in Example 12.

[0460] almost white light obtained was energized the illumination device, can be used as a lighting device component force ivy.

[0461] Example 14

"Preparation of white light emitting element and a white illumination device"

In the preparation of the white light emitting device of Example 12, except that the change in the hole transport control material ACZ1 ACZ2 in the same manner as in Example 12 to prepare a white illumination device.

[0462] almost white light obtained was energized the illumination device, can be used as a lighting device component force ivy.

[0463] Example 15

"Preparation of Organic EL elements 2 1~2- 13"

In the organic EL element 1-1 of Example 1, to change the light emitting dopant Ir 1, the Seiana阻 stop material as described in Table 2, in the same manner except for changing, in the same manner as in Example 1 organic EL element 2 - the ;! ~ 2-13 were produced.

[0464] External extraction quantum efficiency of the resulting respective elements was carried out in the same manner as described in Example 1 to measure the light emission life.

[0465] At this time, both the 100 values ​​of the organic EL device 2-1, showing the value of each organic EL element sample by a relative value. The results obtained are shown in Table 2.

[0466] [Table 2]

From Table 2, the organic EL element using an organic EL device material in the hole blocking material of the present invention is compared with the organic EL device of the comparison, it was found that high luminous efficiency and emission life can be obtained. The emission color of the organic EL device of the present invention were all green.

Claims

Organic elect port luminescent device material which is a orthometal complex represented by the range following formula according (1).
[Formula 1] general formula (1)
(Wherein, M represents a Group 8 to 10 metal elements in the periodic table. L, V represents a different bidentate ligands each other, m is 1 or 2, n is 1 or 2 . However, m + n is in agreement with the charge of M is 2 or 3.
Bidentate ligand L, U is the partial structure ML coordinated to the metal M is represented by the following general formula (2), the partial structure ML 'is represented by the following general formula (3) or (4).
[Formula 2]
- general formula (2) - general formula (31 general formula (4)
X
11 represents a carbon atom or a nitrogen atom, 6 Q
11 carbon atoms and X
It represents a 11 and atomic group forming a ring A is a co-membered aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocycle. X
12 represents a carbon atom or a nitrogen atom, Q
12 is a nitrogen atom and X
It represents an atomic group forming a 12 with a 5-6 membered aromatic heterocyclic ring B. X is 0, S, CH, CHR, CR, NR, P
1 2 2
It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl
twenty two
Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.
X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X
21 21 21
It represents an atomic group forming a ring C is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X
22 represents a carbon atom or a nitrogen atom, Q
22 is a nitrogen atom and X
22 together represent an atomic group forming a ring D is a 5-6 membered aromatic heterocyclic ring. X is 0, S, CH, CHR, CR, NR, P
2 2 2
It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl
twenty two
Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.
X, X represents a nitrogen atom or a phosphorus atom, X is coordinated to M through X, the X
31 32 3 31 32
It represents an atomic group forming a bidentate ligand. )
Organic elect port luminescent device material according to claim 1, wherein the ortho metal complex represented by the following general formula (5).
[Formula 3] the general formula)
(Wherein, M is. Ml representing a 8-10 metal elements of the periodic table is 1 or 2, nl is 1 or 2. However, ml + nl is 2 or 3 M consistent with charge. X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X
11 11 11
It represents an atomic group forming a ring A is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X
12 represents a carbon atom or a nitrogen atom, Q
12 is a nitrogen atom and X
It represents an atomic group forming a 12 with a 5-6 membered aromatic heterocyclic ring B. X is 0, S, CH, CHR, CR, NR, P
1 2 2
It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl
twenty two
Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group.
X
21 represents a carbon atom or a nitrogen atom, Q
21 carbon atoms and X
21 together represent an atomic group forming a ring C is a 6-membered aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocycle. X represents a carbon atom or a nitrogen atom, Q ~6
22 22 nitrogen atoms and X
It represents an atomic group forming a ring D is 22 with 5-membered aromatic heterocyclic. X is 0, represents S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl
twenty two
Group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. However, ring
A and ring C, ring B and ring D does not become the same as at the same time. )
Organic elect port luminescent device material according to claim 1, wherein the ortho metal complex represented by the following general formula (6).
[Formula 4] General formula (6)
(Wherein, M is. M @ 2 representing a 8-10 metal element in the periodic table is 1 or 2, n2 is 1 or 2. However, m @ 2 + n2 is 2 or 3 M consistent with charge. X represents a carbon atom or a nitrogen atom, Q is an aromatic 6-membered together with carbon atoms and X
11 11 11
It represents an atomic group forming a ring A is a hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X
12 represents a carbon atom or a nitrogen atom, Q
12 is a nitrogen atom and X
It represents an atomic group forming a 12 with a 5-6 membered aromatic heterocyclic ring B. X is 0, S, CH, CHR, CR, NR, P
1 2 2
It represents R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl
twenty two
It represents a group, Ariru group, a heterocyclic group or an aromatic heterocyclic group - group, Aruke. X, X is
31 32 represents a nitrogen atom or a phosphorus atom, XX
3 X,
31 32 via a represents an atomic group forming a bidentate ligand coordinated in the M. )
[4] Te you, the general formula (6), organic elect port luminescent device material according to claim 3, wherein the aromatic heterocyclic ring B is a 6-membered ring.
[5] one of the following general formula (7) partial structure represented by or claims first through fourth term, which is a orthometal complexes that have a tautomer thereof as a partial structure 1 organic elect port luminescent device material of the mounting serial to term. [Chem 5] General formula (7)
(Wherein, M represents a Group 8 to 10 metal element of the periodic table. X is or carbon atoms
41
The other represents a nitrogen atom, Q
41 carbon atoms and X
41 with 6-membered aromatic hydrocarbon ring or
It represents an atomic group forming a ring E is a 5- to 6-membered aromatic heterocycle. R represents a substituent, n
41
4 is an integer selected from 0-3. Xa is - N (Ra), - display the S- Ra - O-Ra or
2
It is. Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, the heterocyclic group or aromatic heterocyclic group. Xa is - N (Ra), the two Ra different even with the same
2
One is or may be. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S
4 2 2 2
It represents O or SO. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group
2
, A heterocyclic group or an aromatic heterocyclic group. )
Following general formula (8) or (9) a partial structure or an organic electroluminescence according to claim 5, wherein the ortho metal complex having as a partial structure a tautomer thereof represented Noreminessensu element material.
[Formula 6]
(Wherein, M represents a Group 8 to 10 metal elements in the periodic table. R, R, R, R
51 52 53 54 each represents a hydrogen atom or an electron donating substituent, at least one is an electron-donating substituent. R, R, R, R
56 57 58 59 each represents a hydrogen atom or a substituent, R, R
56 At least one 58 is an electron-withdrawing group. R, R
50 55 represents a substituent, n51, n5
2 is an integer selected from 0-3. Xa is - N (Ra), - display the S- Ra - O-Ra or
2
It is. Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, the heterocyclic group or aromatic heterocyclic group. Xa is - N (Ra), the two Ra different even with the same
2
One is or may be. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S
5 2 2 2
It represents O or SO. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group
2
, A heterocyclic group or an aromatic heterocyclic group. )
Serial following formula partial structure or a tautomer thereof represented by (10) in any one of claims the first to sixth paragraph, characterized in that the ortho-metal complexes that Yusuke as a partial structure organic elect port luminescent device material placement.
[Formula 7] General formula (10) Q 6
Ϊ) ΙΪΙ6 Ichizu 6 ^ 3 F _!
:
X 6 M
\
(A c) n6 -¾4 G:
- -. Qi (wherein, M represents a Group 8 to 10 metal elements in the periodic table X, X, X, X
61 62 63 64 each represent a carbon atom or a nitrogen atom, Q
61 carbon atoms and X, X
61 63 with Represents an atom group forming a ring F is a 6-membered aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocycle, Q is a nitrogen atom and X, aromatic 5-6 membered with X to form a ring G is heterocyclic
62 62 64
It represents a group of atoms that. X, X represents a substituent van der Waals volume is 20 A 3 or more bc
. m6, n6 represents 0 or 1. However, it is m6 + n6≥l. X is 0, S, CH, CHR,
6 2
It represents CR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a consequent
2 2 2
Mouth alkyl group, an alkenyl group, an Ariru group, a heterocyclic group or an aromatic heterocyclic group. )
[8] The organic elect port luminescent device material according to any force one of claims the first to seventh paragraphs, characterized in that the M power iridium or platinum.
[9] Claims organic elect port luminescent element characterized by containing the organic-elect opening luminescent element materials according to any one of first to eighth paragraph.
[10] a light-emitting layer as a constituent layer, organic elect Lono, characterized in that the light-emitting layer contains an organic-elect opening luminescent device material of the mounting serial to any one of the first to eighth, wherein the scope of the claims Reminessensu element n
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Cited By (183)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1647554A2 (en) * 2003-07-22 2006-04-19 Idemitsu Kosan Co., Ltd. Metal complex compound and organic electroluminescent device using same
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US9773986B2 (en) 2009-11-19 2017-09-26 The University Of Southern California Copper(I)-carbene complexes and organic electroluminescent devices
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US10074806B2 (en) 2014-04-15 2018-09-11 Universal Display Corporation Organic electroluminescent materials and devices

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001123982A (en) * 1999-10-25 2001-05-08 Hitachi Ltd Horizontal shaft pump device
JP2002117978A (en) * 2000-07-17 2002-04-19 Fuji Photo Film Co Ltd Luminescent element and iridium complex
JP2002226495A (en) * 2000-11-29 2002-08-14 Canon Inc Metal coordination compound, light emitting element and display device
JP2002234894A (en) * 2000-11-29 2002-08-23 Canon Inc Metal coordination compound, light emission element and display device
JP2002332291A (en) * 2001-03-08 2002-11-22 Canon Inc Metal coordination compound, electroluminescent device, and display unit
JP2002332992A (en) * 2001-05-11 2002-11-22 Toyota Central Res & Dev Lab Inc Impeller of centrifugal compressor
JP2002338588A (en) * 2001-03-14 2002-11-27 Canon Inc Metal coordinated compound, electroluminescent element and display device
JP2003146996A (en) * 2000-09-26 2003-05-21 Canon Inc Light emission element, display and metal coordination compound for the light emission element
WO2004016711A1 (en) * 2002-08-16 2004-02-26 The University Of Southern California Organic light emitting materials and devices

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4460743B2 (en) * 2000-09-29 2010-05-12 富士フイルム株式会社 Method for producing an iridium complex or a tautomer thereof
JP4154145B2 (en) * 2000-12-01 2008-09-24 キヤノン株式会社 Metal coordination compounds, the light emitting device and a display device
JP2002359079A (en) * 2001-05-31 2002-12-13 Canon Inc Light emitting element and display device
JP2003342284A (en) * 2002-05-30 2003-12-03 Canon Inc Metal coordination compound, light-generating element and display device
EP1683804B1 (en) * 2003-11-04 2013-07-31 Takasago International Corporation Platinum complex and luminescent element
US8178214B2 (en) * 2004-02-26 2012-05-15 Konica Minolta Holdings, Inc. Material for organic electroluminescence element, organic electroluminescence element, display device and illumination device

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001123982A (en) * 1999-10-25 2001-05-08 Hitachi Ltd Horizontal shaft pump device
JP2002117978A (en) * 2000-07-17 2002-04-19 Fuji Photo Film Co Ltd Luminescent element and iridium complex
JP2003146996A (en) * 2000-09-26 2003-05-21 Canon Inc Light emission element, display and metal coordination compound for the light emission element
JP2002226495A (en) * 2000-11-29 2002-08-14 Canon Inc Metal coordination compound, light emitting element and display device
JP2002234894A (en) * 2000-11-29 2002-08-23 Canon Inc Metal coordination compound, light emission element and display device
JP2002332291A (en) * 2001-03-08 2002-11-22 Canon Inc Metal coordination compound, electroluminescent device, and display unit
JP2002338588A (en) * 2001-03-14 2002-11-27 Canon Inc Metal coordinated compound, electroluminescent element and display device
JP2002332992A (en) * 2001-05-11 2002-11-22 Toyota Central Res & Dev Lab Inc Impeller of centrifugal compressor
WO2004016711A1 (en) * 2002-08-16 2004-02-26 The University Of Southern California Organic light emitting materials and devices

Cited By (242)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1647554A2 (en) * 2003-07-22 2006-04-19 Idemitsu Kosan Co., Ltd. Metal complex compound and organic electroluminescent device using same
EP1647554A4 (en) * 2003-07-22 2008-02-20 Idemitsu Kosan Co Metal complex compound and organic electroluminescent device using same
US8178874B2 (en) 2003-07-22 2012-05-15 Idemitsu Kosan Co., Ltd. Metal complex compound and organic electroluminescent device using same
US7667228B2 (en) 2003-07-22 2010-02-23 Idemitsu Kosan Co., Ltd. Metal complex compound and organic electroluminescent device using same
US8106390B2 (en) 2003-07-22 2012-01-31 Idemitsu Kosan Co., Ltd. Metal complex compound and organic electroluminescent device using same
US9871219B2 (en) 2005-04-13 2018-01-16 Universal Display Corporation Organic light emitting devices
US9647227B2 (en) 2005-04-13 2017-05-09 Universal Display Corporation Organic light emitting devices
US9735377B2 (en) 2005-05-06 2017-08-15 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
US8889864B2 (en) 2006-02-10 2014-11-18 Universal Display Corporation Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
US9281483B2 (en) 2006-02-10 2016-03-08 Universal Display Corporation Organic electroluminescent materials and devices
US9893306B2 (en) 2006-02-10 2018-02-13 Universal Display Corporation Organic electroluminescent materials and devices
US9548462B2 (en) 2006-02-10 2017-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US9065063B2 (en) 2006-02-10 2015-06-23 Universal Display Corporation Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
JP2008160098A (en) * 2006-11-30 2008-07-10 Semiconductor Energy Lab Co Ltd Light emitting element, light emitting device, and electronic equipment
US9899612B2 (en) 2006-12-08 2018-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US8866377B2 (en) 2006-12-28 2014-10-21 Universal Display Corporation Long lifetime phosphorescent organic light emitting device (OLED) structures
US8592585B2 (en) 2006-12-29 2013-11-26 National Tsing Hua University Phosphorescent iridium complex with non-conjugated cyclometalated ligands, synthetic method of preparing the same and phosphorescent organic light emitting diode thereof
US8030490B2 (en) * 2006-12-29 2011-10-04 National Tsing Hua University Phosphorescent iridium complex with non-conjugated cyclometalated ligands, synthetic method of preparing the same and phosphorescent organic light emitting diode thereof
US8410269B2 (en) 2006-12-29 2013-04-02 National Tsing Hua University Phosphorescent iridium complex with non-conjugated cyclometalated ligands, synthetic method of preparing the same and phosphorescent organic light emitting diode thereof
JP2010516040A (en) * 2007-01-16 2010-05-13 エルジー・ケム・リミテッド Electrolyte and a secondary battery using the same comprising the eutectic mixture
US9190621B2 (en) 2007-03-08 2015-11-17 Universal Display Corporation Materials for organic light emitting diode
US9142786B2 (en) 2007-03-08 2015-09-22 Universal Display Corporation Phosphorescent materials
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US9853227B2 (en) 2007-03-08 2017-12-26 Universal Display Corporation Organic electroluminescent materials and devices
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US9123903B2 (en) 2007-12-28 2015-09-01 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8586204B2 (en) 2007-12-28 2013-11-19 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
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WO2010007107A1 (en) 2008-07-18 2010-01-21 Siemens Aktiengesellschaft Phosphorescent metal complex compound, method for the preparation thereof and radiating component
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US8557400B2 (en) 2009-04-28 2013-10-15 Universal Display Corporation Iridium complex with methyl-D3 substitution
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US9673406B2 (en) 2009-05-20 2017-06-06 Universal Display Corporation Metal complexes with boron-nitrogen heterocycle containing ligands
DE102009031683A1 (en) 2009-07-03 2011-03-24 Siemens Aktiengesellschaft Phophoreszente metal complex compound, processes for preparing it and radiation-emitting component
US9773986B2 (en) 2009-11-19 2017-09-26 The University Of Southern California Copper(I)-carbene complexes and organic electroluminescent devices
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DE102010005634A1 (en) 2010-01-25 2011-07-28 Siemens Aktiengesellschaft, 80333 Novel use of the guanidinium cation and light emitting device
US9169434B2 (en) 2010-01-25 2015-10-27 Osram Ag Phosphorescent metal complex, process for production and light-emitting component
DE102010005632A1 (en) 2010-01-25 2011-07-28 Siemens Aktiengesellschaft, 80333 Phosphorescent metal complex compound, method for producing and light-emitting component
WO2011088918A1 (en) 2010-01-25 2011-07-28 Siemens Aktiengesellschaft Use of a guanidinium cation in a light-emitting component
US9375392B2 (en) 2010-01-25 2016-06-28 Osram Ag Use of the guanidinium cation and light-emitting component
US9156870B2 (en) 2010-02-25 2015-10-13 Universal Display Corporation Phosphorescent emitters
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US8963132B2 (en) 2010-03-25 2015-02-24 Universal Display Corporation Solution processable doped triarylamine hole injection materials
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