WO2006103874A1 - Organic electroluminescent device material, organic electroluminescent device, display and illuminating device - Google Patents

Organic electroluminescent device material, organic electroluminescent device, display and illuminating device Download PDF

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WO2006103874A1
WO2006103874A1 PCT/JP2006/304234 JP2006304234W WO2006103874A1 WO 2006103874 A1 WO2006103874 A1 WO 2006103874A1 JP 2006304234 W JP2006304234 W JP 2006304234W WO 2006103874 A1 WO2006103874 A1 WO 2006103874A1
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group
represents
substituent
general formula
partial structure
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PCT/JP2006/304234
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Masato Nishizeki
Tomohiro Oshiyama
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Konica Minolta Holdings, Inc.
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    • HELECTRICITY
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    • H01L51/0077Coordination compounds, e.g. porphyrin
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    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H01L51/5012Electroluminescent [EL] layer
    • H01L51/5016Triplet emission

Abstract

Disclosed is an organic electroluminescent device material exhibiting high luminous efficiency while having long emission life. Also disclosed are an organic electroluminescent device using such an organic electroluminescent device material, and an illuminating device and display employing such an organic electroluminescent device. The organic electroluminescent device material is characterized by containing an orthometal complex having a partial structure represented by the following general formula (Z).

Description

Specification

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

The display device and a lighting device

Technical field

[0001] The present invention relates to novel organic elect port luminescent device material, an organic-elect opening Ruminesse Nsu device, 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 structure in which between a cathode and an anode of the light-emitting layer containing a compound which emits the electrons and holes to note entering into the light emitting layer, to produce an exciton by recombination , 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~ tens V extent of voltage, further self-luminous rich in viewing angle for certain space-saving because visibility is complete solid element Kogu thin film, have also been noted in view force of portability or the like.

While [0003] is the force, in the organic EL element for future practical use, it has been desired to develop an organic EL element that emits light more efficiently a high luminance with low power consumption.

[0004] In Patent No. 3,093,796, a stilbene derivative, a distyryl Rua Lee alkylene derivatives or tris styryl Rua Lee alkylene derivatives phosphor traces were doped, enhancement of emission luminance, and achieving a long lifetime of the device. The 8-hydroxyquinoline aluminum complex as a host compound, element having an organic light-emitting layer doped with a slight amount of a fluorescent substance (e.g., JP 63- 264692 discloses), 8-hydroxyquinoline aluminum complex Hosutoi 匕合as things, elements having the same organic light-emitting layer doped with a quinacridone type dye (e.g., JP-3- 255190 JP), and the like. [0005] When using the light emission from excited singlet Thus, generation ratio of singlet excitons and triplet excitons of 1: generation probability of an emitting exciton species is 3 is 25%, light the limitation of external extraction quantum efficiency for extraction efficiency of about 20% (7? ext) were 5%.

[0006] However, reports of the organic EL element, employing phosphorescence excited triplet force from Princeton (MA Baldo et al., Nature, 395 Certificates, pp 151-154 (1998)) force has been Ever since , it has become active research of material that exhibits phosphorescence at room temperature. For example, MA Baldo et al., Nature, 403 Certificates, No. 17, pp. 750-753 (2000), also disclosed in U.S. Patent No. 6, 0 97, 147 Pat like.

[0007] Since the upper limit of the internal quantum efficiency by using the excited triplet is 100% theoretically becomes luminous efficiency force doubled as compared with the singlet excited, that almost the same performance is obtained with the cold cathode tube it is also considered for lighting applications because of the potential. For example, S. Lamansky et al., J. Am. Chem. Soc., 123 Certificates, in such page 4304 (2001), a number of I spoon compound is synthesized and studied about the heavy metal complexes such as iridium complexes ing.

[0008] Moreover, the aforementioned MA Baldo et al, Nature, 403 Certificates, No. 17, at pp. 750-753 (200 0 years), tris dopant. (2 Hue - Rubirijin) consider using iridium It is.

[0009] Other, ME Tompson, etc. The 10th International

Workshop on Inorganic and urganic Electroluminescence (EL '00, Hamamatsu) in, as a dopant L Ir (acac), for example, the (ppy) Ir (acac), The Moo

twenty two

n-Jae Youn. Og ゝ Tetsuo Tsutsui, etc., still The 10th International W orkshop on Inorganic and Organic Electroluminescence (EL '00, Hamamatsu) in, as a dopant, tris (2- (p- tolyl) pyridine) iridium (Ir ( ptpy)),

3 tris (benzo [h] quinoline) iridium (Ir (bzq)) are use was investigated Gyotsu the like (Naoko

3

These metal complexes are generally referred to as ortho-metalated iridium complex, Ru. ).

[0010] Also the S. Lamansky et al., J. Am. Chem. Soc., 123 Certificates, pp 4304 (2001) Hitoshinio, even, is an attempt to devices by using a variety of iridium complexes , Ru.

[0011] In order to obtain a high luminous efficiency, The 10th International Workshop on I norganic and Organic Electroluminescence (EL '00, Hamamatsu) I or at the Ikai etc. [or hole transporting compound as the host of the phosphorescent compound It is used. Further, ME To mpson such various electron-transporting material as a host of a phosphorescent I 匕合 was doped with a new I Rijiumu complexes thereto, Ru.

[0012] The ortho-metal complex the central metal was platinum instead of iridium be attention, Ru. For this type of complex, examples which gave characterized ligands are known a number (e.g., Patent Documents 1 to 5 and Non-Patent Document 1 see.) 0

[0013] luminance and luminous efficiency in the case of even a light emitting element for V ヽ deviation, although intended to be significantly improved compared to conventional devices since the light that light emission derived from phosphorescence, element Tsu the emission lifetime, Te and lower than conventional devices, there is cormorants problems. Thus phosphorus luminescent material light of high efficiency is possible to sufficiently achieve the performance improvement in emission life of the short-waved and elements of the emission wavelength can withstand for difficulty instrument real, Do, of at present.

[0014] 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, for emitting lifetime considerably degradation of the device, improvement in the tradeoff is sought, it was.

[0015] As the ligand of the ortho complex, coordinated part content in the metal is a heterocyclic 5-membered containing one non-nitrogen atom such as Chiofen ring or furan ring as such Choi two Rubirijin Reika with ligand ^, there are several, they Nio, are presented Te, Ru structure, the deviation also attached to the 2-position and 3-position of the heterocyclic 5-membered containing one non-nitrogen atom any emission wavelength of complexes using the ligands only Nag one with a hand was only emission examples of long wavelength such as a yellow to red (e.g., Patent Document 2, 11-16; see.).

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: WO 02Z015645 pamphlet

Patent Document 7: JP 2003- 123982 JP

Patent Document 8: JP 2002- 117978 JP

Patent Document 9: JP 2003 - 146996 discloses

Patent Document 10: International Publication No. 04Z016711 pamphlet

Patent Document 11: JP 2002- 175884 JP

Patent Document 12: JP 2001- 181617 JP

Patent Document 13: JP 2001- 247959 JP

Patent Document 14: JP 2003- 73355 JP

Patent Document 15: JP 2003- 81989 JP

Patent Document 16: JP 2003 - 272861 discloses

Non-Patent Document 1: Inorganic Chemistry, 41 Certificates, No. 12, pp. 3055-3066 (2002)

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

Problems that the Invention is to you'll solve

[0016] The present invention has been made in view of the above problems, high luminous efficiency shows, and a long organic elect port luminescent device material emission lifetime, the organic elect port DEVICE USING THE SAME , further to provide a lighting device and a display device using the organic-elect opening eLEMENT.

Means for Solving the Problems

[0017] The above object of the present invention has been achieved by the following constitution.

[0018] 1. Organic elect port luminescent device material which is characterized by containing an ortho metal complex having a partial structure represented by the following general formula (Z).

[0019] [Formula 1] general formula (Z)

[0020] wherein, X represents a 0, S, SO, or SO, X is a divalent group or a single bond. R is location

Representing a 2 1 a substituent. R represents a hydrogen atom or a substituent. L is Kaoru b of the 5- to 7-membered together with the nitrogen atom

To form an aromatic heterocyclic ring. M is to display the groups 8 to 10 of the metal element in the periodic table. ]

2. partial structure represented by the general formula (Z) is an organic elect port luminescent device material according to above, wherein the partial structure der Rukoto represented by the following general formula (1).

[0021] [Formula 2]

- general formula (1)

[0022] wherein, X represents a 0, S, SO, or SO, R represents a substituent. R is a hydrogen atom or

It represents a 10 2 1 2 substituent. Represents X, X, X, X are each C, C- R, N, N- R, O or S,

11 12 13 14 11 11

And form a heteroaromatic ring 5-membered together with the nitrogen atom. R is a hydrogen atom or a substituent

11

A representative. M represents a Group 8 to Group 10 metal element in the periodic table. ]

3. partial structure represented by the general formula (Z) is an organic elect port luminescent device material according to above, wherein the partial structure der Rukoto represented by the following general formula (2).

[0023] [Formula 3] - general formula (2)

[0024] wherein, X represents a 0, S, SO, or SO, R represents a substituent. R is a hydrogen atom or

It represents a 20 2 3 4 substituents. X, X, X, X each represents C-R or N, and the carbon atoms, nitrogen

21 22 23 24 21

To form a 6-membered aromatic heterocyclic ring with the atom. R represents a hydrogen atom or a substituent

twenty one

. M represents a Group 8 to Group 10 metal element in the periodic table. ]

4. partial structure represented by the general formula (Z) is an organic elect port luminescent device material according to above, wherein the partial structure der Rukoto represented by the following general formula (3).

[0025] [Formula 4]

- general formula (3>

[0026] wherein, X represents a 0, S, SO, or SO, R represents a substituent. R is a hydrogen atom or

It represents a 30 2 5 6 substituents. Represents X, X, X, X are each C, C- R, N, N- R, O or S,

31 32 33 34 31 31

And form a heteroaromatic ring 5-membered together with the nitrogen atom. R is a hydrogen atom or a substituent

31

A representative. X is 0, S, CH, CHR, C (R), NR, PR, Si (R), C = 0, C = NR, SO,

0 2 2 2

Representing the SO. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, a heterocyclic

2

It represents a group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table. ]

5. partial structure represented by the general formula (Z) is an organic elect port luminescent device material according to above, wherein the partial structure der Rukoto represented by the following general formula (4).

[Chem 5] General formula (4)

[0028] wherein, X represents a 0, S, SO, or SO, R represents a substituent. R is a hydrogen atom or

It represents the 40 2 7 8 substituents. X, X, X, X

41 42 43 44 are each C-R

It represents 41 or N, and form a heteroaromatic ring of 6-membered carbon atoms, together with nitrogen atom. R represents a hydrogen atom or a substituent

41

. X is 0, S, CH, CHR, C (R), NR ゝ PR, Si (R), C = 0, C = NR, SO, and SO

0 2 2 2 2 represents. R is an alkyl group, a cycloalkyl group, Aruke - represents a group, Ariru group, the heterocyclic group or aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table. ]

6. partial structure represented by the general formula (2) An organic elect port luminescent device material according to the 3, which is a partial structure represented by the following general formula (5).

[0029] [Formula 6] General

[0030] [wherein, R represents a substituent, R represents a hydrogen atom or a substituent. One also less of R and R is an electron-donating substituent or an electron-withdrawing group. X is

51 o, s, it represents the so or SO. R represents a substituent, n51 is an integer selected from 0-3. Xa is

2 50

-N (Ra), -O-Ra or - represents an S-Ra. Ra represents an alkyl group, a cycloalkyl group,

2

An alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. If Xa Gar N of (Ra), 2 two Ra may be different even in the same. M is in the periodic table

2

It represents a Group 8 to Group 10 metal element. ]

7. partial structure represented by the general formula (4) An organic elect port luminescent device material according to the 5, which is a partial structure represented by the following general formula (6).

[0031] [I spoon 7] the general formula (6)

[0032] [wherein, R represents a substituent, R represents a hydrogen atom or a substituent. When the least of R and R

56 57 56 57 also one is an electron-donating substituent or an electron-withdrawing group. X is

52 o, s, it represents the so or SO. R represents a substituent, n52 is an integer selected from 0-3. Xa is

2 55

-N (Ra), -O-Ra or - represents an S-Ra. Ra represents an alkyl group, a cycloalkyl group,

2

An alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. If Xa Gar N of (Ra), 2 two Ra may be different even in the same. X is 0, S, CH, CHR,

2 0 2

C (R), represents NR, PR, Si (R), C = 0, C = NR, SO, and 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.

M represents a Group 8 to Group 10 metal element in the periodic table. ]

8. The partial structure represented by the general formula (1) is represented by the following general formula (7A) or the general formula organic elect port luminescent element in the 2, which is a partial structure represented by (8A) material.

[0033] [Formula 8] formula (7A) formula (8Α>

[0034] [represents wherein, X, X, X, X is each a carbon atom or a nitrogen atom, Q is a carbon atom, X

61 62 63 64 1

Represents an atomic group forming an aromatic heterocyclic ring of 5 members together X, Q are carbon atoms, X, X

61 62 2 63 64

Represents an atomic group forming an aromatic heterocyclic ring of 5 members together with the nitrogen atom. X, X is 0, S, S

1 2

It represents O or SO. R represents a substituent, R represents a hydrogen atom or a substituent. R,

2 15 26 16

R, R, R represents a substituent van der Waals volume is 20 A 3 or more. n61, n6

17 25 27

2, n63 is 0 or 1. However, it is n61 + n62≥l. M represents a Group 8 to Group 10 metal element in the periodic table. ]

9. Formula partial structure represented by (2) the following general formula (7B) or the general formula organic elect port luminescent element in the 3, which is a partial structure represented by (8B) material.

[0035] [Chem 9] Formula (7B) Formula I8beta)

[Represents wherein, X, X, X, X is each a carbon atom or a nitrogen atom, Q is a carbon atom, X

61 62 63 64 1

Represents an atomic group forming an aromatic heterocyclic 6-membered together X, Q are carbon atoms, X, X

61 62 2 63 64

Represents an atomic group forming an aromatic heterocyclic 6-membered together with the nitrogen atom. X, X is 0, S, S

1 2

It represents O or SO. R represents a substituent, R represents a hydrogen atom or a substituent. R, R, R, R represents a substituent van der Waals volume is 20 A 3 or more. n61, n6

17 25 27

2, n63 is 0 or 1. However, it is n61 + n62≥l. M represents a Group 8 to Group 10 metal element in the periodic table. ]

10. partial structure represented by the general formula (3) is an organic elect port Rumine' according to the 4, which is a partial structure represented by the following general formula (9A) or the general formula (10A) sense element material.

[0037] [of 10]

[0038] [represents wherein, X, X, X, X is each a carbon atom or a nitrogen atom, Q is a carbon atom, X

71 72 73 74 3

Represents an atomic group forming an aromatic heterocyclic ring of 5 members together X, Q are carbon atoms, X, X

71 72 4 73 74

Represents an atomic group forming an aromatic heterocyclic ring of 5 members together with the nitrogen atom. X, X is 0, S, S

3 4

It represents O or SO. R represents a substituent, R represents a hydrogen atom or a substituent. R,

2 35 46 36

R, R, R represents a substituent van der Waals volume is 20 A 3 or more. n71, n7

37 45 47

2, n73 is 0 or 1. However, it is n71 + n72≥l. X is 0, S, CH, CHR, C

0 2

(R), represents NR, PR, Si (R), C = 0, C = NR, SO, and SO. R is an alkyl group, a cycloalkyl

2 2 2

Alkyl group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table. ]

11. partial structure represented by the general formula (4) is an organic elect port Rumine' according to the 5, which is a partial structure represented by the following general formula (9B) or the general formula (10B) sense element material.

[0039] [Chem. 11] General

[0040] [represents wherein, X, X, X, X is each a carbon atom or a nitrogen atom, Q is a carbon atom, X

71 72 73 74 3

Represents an atomic group forming an aromatic heterocyclic 6-membered together X, Q are carbon atoms, X, X

71 72 4 73 74

Represents an atomic group forming an aromatic heterocyclic 6-membered together with the nitrogen atom. X, X is 0, S, S

3 4

It represents O or SO. R represents a substituent, R represents a hydrogen atom or a substituent. R,

2 35 46 36

R, R, R represents a substituent van der Waals volume is 20 A 3 or more. n71, n7

37 45 47

2, n73 is 0 or 1. However, it is n71 + n72≥l. X is 0, S, CH, CHR, C

0 2

(R), NR, PR, Si (R), C = 0, C = NR, SO, and SO table. R is an alkyl group, a cycloalkyl

2 2 2

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

M represents a Group 8 to Group 10 metal element in the periodic table. ]

12. The M in the general formula (Z) is an organic elect port luminescent device material according to prior SL 1, characterized in that iridium or platinum.

[0041] 13. The organic elect port luminescent device material according to 1, organic-elect opening luminescent element characterized by containing at least one layer of constituent layers.

[0042] 14. a light-emitting layer as a constituent layer, organic elect port ELEMENT light emitting layer, characterized in that it contains an organic-elect opening Rumine' sensing device material according to the 1.

[0043] 15. Viewing apparatus characterized by having an organic-elect opening device as described in the 13.

[0044] 16. lighting apparatus characterized by having an organic-elect opening device as described in the 13.

Effect of the invention

[0045] The present invention exhibit high luminous efficiency and a long organic elect port Ruminesse Nsu device material emission lifetime, the organic elect port luminescent device using the same, even illumination device and using organic electronics Toro ELEMENT It was able to provide a display device. BRIEF DESCRIPTION OF THE DRAWINGS

[0046] FIG. 1 is a schematic diagram showing an example of an organic EL device power composed display device.

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

FIG. 3 is an equivalent circuit diagram of a driving circuit constituting the 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

[0047] 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

102 glass cover

105 cathode

106 organic EL layer

107 transparent electrode-attached glass substrate

108 nitrogen gas

109 Tomizuzai

DETAILED DESCRIPTION OF THE EMBODIMENTS [0048] The present inventors have result of intensive studies, terrorism coordinating moiety to the metal as a ligand an ortho metal complex 5-membered non-nitrogen atom containing one emission lifetime with Chi lifting light emission of a short wavelength such as blue to blue-green in the case of using the 3-position and 4-position a ligand having a partial structure that has a bond of the ring, exhibit high luminous efficiency It found that is greatly improved. Note that you the present invention, are described Te, Ru partial structure also includes partial structure of a tautomer thereof

[0049] Hereinafter, details of each component according to the present invention will be sequentially described.

[0050] Organic elect port luminescent device material Nio of the present invention, Te is characterized by containing an ortho metal complex having a partial structure table by the general formula (Z).

[0051] Formula according to claim 1, wherein in (Z), X is 0, S, SO or SO

2 represents, X represents a divalent group or a single bond. R represents a substituent. R is a hydrogen atom or

1 ab

It represents a substituent. L forms an aromatic heterocyclic 5- to 7-membered together with the nitrogen atom. M represents a Group 8 to Group 10 metal element in the periodic table. The M, is preferably iridium or platinum.

[0052] Further, in the organic-elect opening luminescent device material of the present invention, the general formula (Z

) Partial structure represented by is preferably at least one moiety structure selected from the general formulas (1) to (4).

[0053] The content layer in the general formula (1) organic-elect opening luminescent device material of at least one ortho metal complex is selected ~ from partial structure group consisting of (4) according to the present invention, the light emitting layer or a positive If the hole blocking layer contains the preferred tool also light emitting layer by using as a light emitting dopant 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.

[0054] Hereinafter, the general formula of the present invention (1) to (4) partial structure represented details of ortho metal complex having the at explained.

[0055] "ortho metal complex having a partial structure represented by the general formula (1)"

In the general formula (1) as claimed in claim 2, X is 0, S, SO or SO

Represents 10 2, R represents a substituent. R represents a hydrogen atom or a substituent. X, X, X, X

1 2 11 12 13 14 each represent C, C-R, N, N-R, O or S, and form a heteroaromatic ring 5-membered together with the nitrogen atom. R represents a hydrogen atom or a substituent. M is put to the Periodic Table of the Elements

11

That represents the Group 8 to Group 10 of the metal element.

[0056] R, examples of the substituent represented by R include an alkyl group (e.g., methyl group, Echiru group,

1 11

Isopropyl, hydroxy E methyl group, a methoxymethyl group, triflate Ruo Russia methyl, t Buchi group, a pentyl group, Okuchiru group, Bruno - group, decyl group), cycloalkyl group (e.g., cyclopentyl, cyclohexylene hexyl group, etc.), Ararukiru group (e.g., benzyl, 2-off Enechiru group), Ariru group (e.g., Hue - Le group, p- black port phenyl group, a mesityl group, a tolyl group, a xylyl group, Bifuwe - Lil group, a naphthyl group, an anthryl group, Fuenantoriru group), a Hajime Tamaki (e.g., a pyrrolidyl group, an imidazolyl group, a morpholyl group, Okisazorijiru group), an aromatic Hajime Tamaki (e.g., furyl group, thienyl group, a pyridyl group, pyridazinyl group, pyrimidinyl group, Birajiniru group, triazinyl group, an imidazolyl group, a pyrazolyl group, thiazol group, Kinazori Group, carbazolyl group, Karubori - group, a di § The carbazolyl group (di § Zakarubazoriru group, those optionally one of the carbon atoms constituting the carboline ring of the carbolinyl group is substituted by a nitrogen atom shown.) Futarajuru group), an alkoxy group (e.g., ethoxy group, isopropoxy group, butoxy group), Ariruokishi group (e.g., full enoxy group, Nafuchiruokishi group), Shiano group, a hydroxyl group, an alkenyl group (e.g., Bulle group), styryl group, a halogen atom (e.g., chlorine atom, bromine atom, iodine atom, fluorine atom, etc.) and the like, and more preferably an alkyl group, a cycloalkyl group, Ariru group, double heterocyclic group, an aromatic it is a family heterocyclic group. These groups may be further substituted.

[0057] X, X, X, X each represent C, C- R, N, N- R, O or S, and nitrogen atom

11 12 13 14 11 11

Forms a heteroaromatic ring 5-membered together, Specific examples of the aromatic heterocyclic mosquito ゝ mowing 5-, imidazole ring, pyrazole ring, isothiazole ring, isoxazole ring, Okisazo Lumpur ring, thiazole ring, Toriazoru ring and the like.

[0058] In the present invention, the partial structure represented by the general formula according to the present invention (1) is selected following one general formula (1) -1 to (1) partial structure group forces represented by -15 also it is preferably at least one partial structure.

[0059] [of 12]

[0060] the general formula (1) 1 (: at 0-15, R, R represents each represents a substituent, R represents water

It represents a 12 14 13 atom or a substituent. nl is an integer, each selected from 0 to 2. X is 0, S,

15

Represents SO or SO, X are each> N-R, - represents a S - O or. R is

2 16 15 15 Kill group, a cycloalkyl group, Aruke - represents a group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table.

[0061] R, R, examples of the substituent represented by R, the same as the substituents R, R represents in the general formula (1)

12 14 13 1 11

It includes the like. Specific groups R are the same ones as R in the general formula (3) described later

15

And the like.

[0062] Further, in the present invention, it partial structure represented by the general formula according to the present invention (1) is a partial structure represented by the general formula (7A) or the general formula (8A) preferred,.

[0063] Formula (7A) or the general formula (8A), X, X, X, X are each a carbon sheet

61 62 63 64

Or represents a nitrogen atom, Q is form an aromatic heterocyclic ring of 5-membered carbon atoms, X, with X

1 61 62

Represents an atomic group for, Q is a carbon atom, X, X, an aromatic heterocyclic ring of 5- together with the nitrogen atom

2 63 64

It represents a formation to atomic group. X, X represents 0, S, SO or SO. R represents a substituent

1 2 2 15

, R represents a hydrogen atom or a substituent. R, R, R, R is the van der Waals volume

26 16 17 25 27

It represents a substituent is force S20A 3 or more. n61, n62, n63 represents 0 or 1. However, it is n61 + n62≥ 1. M represents a Group 8 to Group 10 metal element in the periodic table.

[0064] R, examples of the substituent represented by R, R in the general formula (1), also the same as the substituent represented by R

15 26 1 11

And the like of it. Q is original to form an aromatic heterocyclic ring of 5-membered carbon atoms, X, with X

1 61 62

It represents an element group, wherein the 5-membered Okisazoru ring aromatic heterocyclic, Chiofu down ring, a furan ring, a pyrrole ring, an imidazole ring, a pyrazole ring, Toriazoru ring and the like. The Q forms a heteroaromatic 5-membered ring together with the carbon atoms, X, X, a nitrogen atom Hara

2 63 64

Represents an element group, the aromatic heterocyclic 5-membered, Okisazoru ring, pyrrole ring, imidazole ring, pyrazole ring, Toriazoru ring and the like.

[0065] R, R, R , R each represents a substituent van der Waals volume is 20 A 3 or higher,

16 17 25 27

The van der Waals (VDW) volume of substituents include, but using parameters use is determined Te a Accelrys Inc. molecular simulation Nsofuto Cerius 2, by introducing a substituent on the benzene ring, with a Dreiding Force Field, to optimize the molecular structure MM calculation is defined as Volume value obtained using the Co nnoly Surface. It shows a van Ruwanoresu (VDW) volume specific substituents shown below.

[0066] substituent A 3

Mechinore based on 25.4

Echiru based on 42.6

Isopropylidene Norre based on 59.5

tert- Buchinore based on 76.2

Hue - Le based on 74.9

Methoxy 34.0 amino 22.2

A hydroxyl group 16.7

Chlorine atom 22.4

Bromine atom 26.5

Fluorine atom 13.3

Triflate Ruo b methyl 42.5

Thus R, R, R, as the R, for example, methyl, Echiru group, an isopropyl group

16 17 25 27

, Tert- butyl group, phenyl group, methoxy group, an amino group, a chlorine atom, a bromine atom, triflic Oromechiru group and the like.

[0067] "ortho metal complex having a partial structure represented by the general formula (2)"

In the general formula (2) as claimed in claim 3, X is 0, S, SO or SO

It represents 20 2, R

3 represents a substituent. R

4 represents a hydrogen atom or a substituent. X, X, X, X

21 22 23 24 each represent a CR or N, and aromatic heterocyclic 6-membered carbon atoms, together with the nitrogen atom

twenty one

To form. R

21 represents a hydrogen atom or a substituent. M is a group 8 of the periodic table

~ Represents a Group 10 metal element.

[0068] R, examples of the substituent group represented R, R is, R in the general formula (1), similar to the substituent represented by R

3 4 21 1 11

Include those of. X, X, X, X each represents C-R or N, and the carbon atom

21 22 23 24 21

, It will form an aromatic heterocyclic 6-membered together with the nitrogen atom, specifically as an aromatic heterocyclic force mowing 6-membered pyridine ring, a pyrimidine ring, pyridazine ring, pyrazine ring and the like.

[0069] In the present invention, the partial structure represented by the general formula (2) according to the present invention is the following one general formula (2) - 1 (2) - partial structure group forces represented by 6 also selected it is preferably at least one partial structure.

[0070] [of 13]

[0071] the general formula (2) - In. 1 to (2) -6, R, R represents each represents a substituent, R represents a hydrogen

22 represents a 24 23 atom or a substituent. n2 is an integer selected from 0-2. X is 0, S, SO or

twenty five

The other represents the SO. M represents a Group 8 to Group 10 metal element in the periodic table.

2

[0072] R, R, examples of the substituent represented by R, the same as the substituents R, R represents in the general formula (1)

22 24 23 1 11

It includes the like.

[0073] Further, the partial structure represented by the general formula (2), it is preferable that the a partial structure represented by the general formula (5).

[0074] Formula according to claim 6 in (5), R represents a substituent, R represents

It represents a 51 52 each hydrogen atom or a substituent. R

51 and R

At least one of the 52 is an electron donating substituent or an electron-withdrawing group. X represents 0, S, SO or SO. R is a substituted

It represents 51 2 50 group, n51 is an integer selected from 0-3. Xa is -N (Ra), - O-Ra or

2

Representing the S- Ra. Ra represents an alkyl group, a cycloalkyl group, Aruke - represents a group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. Xa is - N (Ra), 2 two Ra is the same

2

Different even if, even if,. M represents a Group 8 to Group 10 metal element in the periodic table.

[0075] R, R, examples of the substituent represented by R, the same as the substituents R, R represents in the general formula (1)

51 52 50 1 11

It includes the like. Specific groups of Ra are the same as R in the general formula (3) described later can be mentioned up. At least one electron donating substituent or an electron withdrawing location of R and R

51 52

Is a substituent force where the electron donating substituent is a Hammett's substituent constant sigma [rho be a negative value indicates the to groups, specifically hydroxy group, an alkoxy group (e.g., methoxy), § Shi Ruokishi group (e.g., Asechiruokishi group, Benzoiruokishi group), an amino group, Jimechirua amino group, Asechiruamino group, an alkyl group (e.g., methyl group, propyl group) include, Ariru group (e.g., phenyl group, a mesityl group) and the like It is. On the other hand, electron-withdrawing substituents to radicals indicating values ​​substituent constant sigma [rho positive Ha Met, specifically Shiano group, alkoxycarbonyl Kishikarubo - group, § reel O propoxycarbonyl - Le group force Rubamoiru group, an imino group, substituted imino group Ν atom, Chiokarubo - group, a sulfamoyl group, an alkylsulfonyl - group, Arirusuruho - group, a nitro group, a halogen atom, per full O b alkyl group, Pafuru O b alkane group, a sulfonamido group, Ashiru group, a formyl group, a phosphoryl group, carboxy group (or a salt thereof), a sulfo group (or a salt thereof), a heterocyclic group, an alkenyl group, Al Kiniru group, Ashiruokishi group, Ashiruchio group, sulfo - a Ruokishi group or Ariru group substituted by these electron-withdrawing group. The heterocyclic group herein, a heterocyclic group, saturated or unsaturated, such as a pyridyl group, quinolyl group, quinoxalinyl group, Piraji two group, benzotriazoles § benzotriazolyl group, an imidazolyl group, benzimidazolyl group, Hidantoin 1 I group, succinimido group, phthalimido group and the like as an example.

[0076] Further, preferred that said in formula partial structure represented by the partial structure force said general formula represented by (2) (7Β) or the general formula (8Β),.

[0077] In Formula (7.beta.) Or the general formula (8Β), X, Χ, Χ, Χ each carbon atom

61 62 63 64

Or represents a nitrogen atom, Q is form an aromatic heterocyclic 6-membered carbon atoms, X, with X

1 61 62

Represents an atomic group for, Q is a carbon atom, X, X, an aromatic heterocyclic 6-membered together with the nitrogen atom

2 63 64

It represents a formation to atomic group. X, X represents 0, S, SO or SO. R represents a substituent,

1 2 2 15

R represents a hydrogen atom or a substituent. R, R, R, R is the van der Waals volume

26 16 17 25 27

It represents a substituent is 20 A 3 or more. n61, n62, representing a 1163 [or 0 or [or 1. However, it is n61 + n 62≥1. M represents a Group 8 to Group 10 metal element in the periodic table.

[0078] R, examples of the substituent represented by R, R in the general formula (1), also the same as the substituent represented by R

15 26 1 11

And the like of it. Q is original to form an aromatic heterocyclic 6-membered carbon atoms, X, with X

1 61 62

It represents an element group, the aromatic heterocyclic ring where the six-membered, pyridine ring, pyridazine ring, Pirimi Jin ring, pyrazine ring, triazine ring and the like. The Q is a carbon atom, X, X, represents an atomic group forming an aromatic heterocyclic ring of 5 members together with the nitrogen atom, it is a 6-membered aromatic heterocyclic ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, pyrazine ring, a triazine ring, and the like et be.

[0079] R, R, R , R represents a substituent van der Waals volume is 20 A 3 or higher, before

16 17 25 27

It includes the same groups as serial general formula (7A) or the general formula (8A).

[0080] "ortho metal complex having a partial structure represented by the general formula (3)"

In the general formula (3) according to claim 4, X is 0, S, SO or SO

Represents 30 2, R represents a substituent. R represents a hydrogen atom or a substituent. X, X, X, X

5 6 31 32 33 34 each C, C-R, N, N-R, represents O or S, and aromatic 5-membered together with the nitrogen atom

31 31

To form a family heterocycle. R represents a hydrogen atom or a substituent. X is 0, S, CH, CHR

31 0 2

Represents C (R), NR, PR, Si (R), C = 0, C = NR, SO, and SO. R is an alkyl group, shea

2 2 2

Black alkyl group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table.

[0081] R, examples of the substituent group represented R, R is, R in the general formula (1), similar to the substituent represented by R

5 6 31 1 11

Include those of. X, X, X, X are each C, C- R, N, N- R, O or S

31 32 33 34 31 11

Represents, although and form a heteroaromatic ring 5-membered together with the nitrogen atom, Specific examples of the aromatic heterocyclic ring such 5-membered, those cited by the general formula (1).

[0082] R is an alkyl group (e.g., methyl group, Echiru group, an isopropyl group, a hydroxy E methyl group, a methoxymethyl group, triflate Ruo Russia methyl, t-butyl group, a pentyl group, Okuchiru group, Bruno - group, decyl group), cycloalkyl group (e.g., cyclopentyl, alkoxy Le group cyclohexylene, etc.), an alkenyl group (e.g., vinyl group, etc.), Ariru group (e.g., full sulfonyl group, p Kurorofuwe - group, mesityl group, tolyl group, xylyl group, Bifuwe - Lil group, a naphthyl group, an anthryl group, full Nantoriru group), a Hajime Tamaki (e.g., a pyrrolidyl group, an imidazolyl group, a morpholyl group, Okisazorijiru group), an aromatic Hajime Tamaki (e.g. , furyl group, Choi - group, a pyridyl group, pyridazinyl group, pyrimidinyl group, Pirajuru group, triazinyl group, Imida Zoriru group, a pyrazolyl group Thiazolyl group, a quinazolinyl group, carbazolyl group, carbolinyl group, a di § The carbazolyl group (di § The carbazolyl group, said Karubori - one nitrogen to an arbitrary carbon atom constituting the Karubori down ring Le group indicating those substituted with atoms.), represents the full Tarajiniru group).

[0083] Further, the partial structure represented by the general formula (3) is represented by the following general formula (3) - 1 (3) - partial structure group forces Table 15 in at least one partial structure selected there it is preferable.

[0084] [of 14]

[0085] Te Oi to the over general formula (3) -1~ (3) -15, 1, R each represents a substituent, R represents water

It represents a 32 34 33 atom or a substituent. n3 is an integer, each selected from 0 to 2. X is 0, S,

35

Represents SO or SO, X are each> N-R, - represents S- a - O-or. R is

2 36 35 35 Kill group, a cycloalkyl group, Aruke - represents a group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. X is 0, S, CH, CHR, C (R), NR, PR, Si (R), C = 0, C = NR,

SO, representing the SO. R is an alkyl group, a cycloalkyl group, Aruke - represents a group, Ariru group, double heterocyclic group or aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table.

[0086] R, R, examples of the substituent represented by R, the same as the substituents R, R represents in the general formula (1)

32 34 33 1 11

It includes the like. R, like the elevation and R of a specific group of R is the formula (3)

35

It is below.

[0087] Moreover, the general formula (3) a partial structure force said general formula represented (9A) or the general formula (10

Preferred that a partial structure represented by A),.

[0088] In Formula (9A) or the general formula (10A), X, X, X, X are each carbon intensity

71 72 73 74

Represents child or nitrogen atom, Q is form an aromatic heterocyclic ring of 5- carbon atoms, X, with X

3 71 72

Represents an atomic group for forming, Q is a carbon atom, X, X, heteroaromatic 5- together with the nitrogen atom

4 73 74

It represents an atomic group forming a ring. X, X represents 0, S, SO or SO. R is a substituent

3 4 2 35

Represents, R represents a hydrogen atom or a substituent. R, R, R, R van der Waals

46 36 37 45 47

Volume represents a substituent at 20A 3 or more. n71, n72, n73 represents 0 or 1. However, it is n71 + n72≥l. X is 0, S, CH, CHR, C (R), NR, PR, Si (R), C = 0,

0 2 2 2

C = NR, SO, represents the SO. R is an alkyl group, a cycloalkyl group, Aruke - group, § Li

2

Lumpur group, a heterocyclic group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table.

[0089] R, examples of the substituent represented by R, R in the general formula (1), also the same as the substituent represented by R

35 46 1 11

And the like of it. 5-membered aromatic heterocycle, for van der Waals volume, are similar to those of the one general formula (7A) or the general formula (8A). Specific groups for R include those similar to the R of the one general formula (3).

[0090] "ortho metal complex having a partial structure represented by the general formula (4)"

In the general formula according to claim 5 (4), X is 0, S, SO or SO

Represents 40 2, R represents a substituent. R represents a hydrogen atom or a substituent. X, X, X, X

7 8 41 42 43 44 each represent a CR or N, and aromatic heterocyclic 6-membered carbon atoms, together with the nitrogen atom

41

To form. R represents a hydrogen atom or a substituent. X is 0, S, CH, CHR, C (R),

41 0 2 2

NR, PR ゝ Si (R), C = 0, C = NR ゝ SO, represents the SO. R is an alkyl group, a cycloalkyl

twenty two

It represents Kill group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table.

[0091] R, examples of the substituent group represented R, R is, R in the general formula (1), similar to the substituent represented by R

7 8 41 1 11

Include those of. X, X, X, X each represents C-R or N, and the carbon atom

41 42 43 44 41

, It will form an aromatic heterocyclic 6-membered together with the nitrogen atom, specifically as an aromatic heterocyclic force mowing 6-membered, those cited by the general formula (2). Specific groups for R include those similar to the R in the general formula (3).

[0092] Further, the partial structure represented by the general formula (4), it is preferable that the a partial structure represented by the general formula (6).

[0093] In the general formula (6), R represents a substituent, R represents a hydrogen atom or a substituent table

56 57

It is. In at least one electron donating substituent or an electron-withdrawing substituents R and R

56 57

is there. X represents 0, S, SO or SO. R represents a substituent, n52 is selected from 0-3

52 2 55

It represents an integer. Xa is - N (Ra), -O-Ra or - represents an S-Ra. Ra is an alkyl

2

It represents group, a Ariru group, a heterocyclic group or an aromatic heterocyclic group - group, a cycloalkyl group, Aruke. Xa is - N (Ra), 2 two Ra may be different even in the same. X

2 0 0 represents S, CH, CHR, C (R), NR, PR, Si (R), C = 0, C = NR, SO, and SO

2 2 2 2

. R is an alkyl group, a cycloalkyl group, Aruke - represents a group, Ariru group, a heterocyclic group, or Kaoru aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table

[0094] R, R, examples of the substituent represented by R, the same as the substituents R, R represents in the general formula (1)

56 57 55 1 11

It includes the like. Specific groups of Ra has exemplified et is the same as R in the general formula (3). R is the same as those of the above general formula (3) R. At least one of R and R

56 52

While an electron donating substituent or an electron-withdrawing group, which the general formula (

5) are similar to those mentioned.

[0095] Further, the partial structure represented by the general formula (4) is represented by the following general formula (4) - 1 (4) -6 Tona Ru partial structure group force is also at least one partial structure selected it is preferable.

[0096] [Formula 15] (4) Single 1 (4) -2 (4 Bok 3 (4) - 4

(

[0097] In the general formula (4) (4) 6, R, R each represents a substituent, R represents a hydrogen atom

42 44 43

Or a substituted group. n4 is an integer selected from 0-2. X is 0, S, SO or S

45

Representing the O. X is 0, S, CH, CHR, C (R), NR, PR, Si (R), C = 0, C = NR, S

2 0 2 2 2

0, representing the SO. R is an alkyl group, a cycloalkyl group, Aruke - group, Ariru group, double

2

It represents a heterocyclic group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table.

[0098] R, R, examples of the substituent represented by R, the same as the substituents R, R represents in the general formula (1)

42 44 43 1 11

It includes the like. Specific groups R is Ru include the same above general formula (3) R.

[0099] Moreover, the general formula (4) a partial structure force said general formula represented (9B) or the general formula (10

Is preferred, it is a partial structure represented by B).

[0100] In Formula (9B) or the general formula (10B), X, X, X, X are each carbon intensity

71 72 73 74

Represents child or nitrogen atom, Q is form an aromatic heterocyclic ring of six-membered carbon atoms, X, with X

3 71 72

It represents a group of atoms formed, Q

4 carbon atoms, X, X

73 74, represents an atomic group forming an aromatic heterocyclic 6-membered together with the nitrogen atom. X, X 0 O be. R

3 4, S, S, or SO

2 Table 35 represents a substituent, R represents a hydrogen atom or a substituent. R, R, R, R van der Waals

46 36 37 45 47

Volume represents a substituent at 20A 3 or more. n71, n72, n73 represents 0 or 1. However, it is n71 + n72≥l. X is 0, S, CH, CHR, C (R), NR, PR, Si (R), C = 0,

0 2 2 2

C = NR, SO, represents the SO. R is an alkyl group, a cycloalkyl group, Aruke - represents a group, § Li Lumpur group, a heterocyclic group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table.

[0101] R, examples of the substituent represented by R, R in the general formula (1), also the same as the substituent represented by R

35 46 1 11

And the like of it. 6-membered aromatic heterocycle, for van der Waals volume, are similar to those of the one general formula (7B) or the general formula (8B). Specific groups for R include those similar to the R of the one general formula (3).

[0102] As preferred ヽ ones orthometal complexes according to the present invention, with parts partial structures have a ligand represented by the general formula (Z), negative monovalent § - one of the monodentate ligand, minus monovalent bidentate ligand, uncharged monodentate ligands, bidentate ligands uncharged. in particular, minus monovalent § - No combination with on of monodentate ligands It is preferred, and Mochiiruko the monodentate ligands of charge. Minus monovalent § - to use in combination with the on-resistance of monodentate ligands better good, as the monodentate ligand uncharged include uncharged monodentate ligands described below.

[0103] (minus monovalent § - one of the monodentate ligands)

In the present invention, § is selected from the group A shown in ortho metal complex force below - preferably to have an on-resistance of the monodentate ligand.

[0104] [of 16]

Br

~ S - ei C≡C- 6 i

J c≡c (Rs2) n8

[0105] In the above A gun, R represents an alkyl group, a cycloalkyl group, Ariru group, a heterocyclic TamakiHajimema

61

Other represents an aromatic heterocyclic group. R represents a substituent, tables an integer selected from n8 is 0 3

62

It is.

[0106] Specific groups R, the general formula (3), et al, are the same as those of the R excluding alkenyl groups

61

It is. The substituent represented by R, also the same as the substituents RR in formula (1) represents

62 1 11

And the like of it.

[0107] (minus monovalent bidentate ligand)

In the present invention, preferably has a partial structure mosquitoes ゝ et minus monovalent bidentate ligand selected listed ortho metal complex forces below.

[0108] [Formula 17]

[8ΐ ^] [6010]

^ Fei 0 £ / 900Zdf / E :) d LZ 1 ^ 8 £ 0I / 900Z OAV, '',

, - <¾ ·

'

'- s

To N

, Ο R

Roh R M

Down one

O

[0110] In the above bidentate ligand represents R, R, respectively R is an alkyl group, a cycloalkyl group, an Ariru group, a heterocyclic group or an aromatic heterocyclic group. R represents a substituent, the n9

Represents an integer of 0 to 3, NLO is an integer of 0 to 2. R represents R -CO- or R -SO, R represents an alkyl group, a cycloalkyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. Q forms a heteroaromatic ring 5-6 membered carbon, together with the nitrogen. Q forms a heteroaromatic ring 5-membered carbon, together with the nitrogen.

[0111] The above negative monovalent § - in the on resistance of the bidentate ligand, R, R, R represents an alkyl group, a cycloalkyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. R is

Represents a 65 substituent, n9 is an integer of 0 to 3, NLO is an integer of 0 to 2. R is R -CO

67 68 or an R -SO-, R is an alkyl group, a cycloalkyl group, Ariru group, a heterocyclic

68 2 68

It represents a cyclic group or an aromatic heterocyclic group. Q is an aromatic heterocyclic 5-6 membered carbon, together with the nitrogen

Five

To form. Q forms a heteroaromatic ring 5-membered carbon, together with the nitrogen.

6

[0112] R, R, R, specifically group R is also the same as R excluding alkenyl groups of the general formula (3)

63 64 66 68

And the like of it. The substituent represented by R, R in the general formula (1), the substituents represented by R

65 1 11

It is the same as those for. Q has the same meaning as in the general formula (8). Pyrrole as Q

5 2 6

Ring, a triazine ring, an imidazole ring, a pyrazole ring, Toriazoru ring and the like.

[0113] (uncharged bidentate ligand)

In the present invention, it preferred to have uncharged bidentate ligand selected partial structure mosquito ゝ et listed ortho metal complex forces below.

[0114] [Formula 19]

20] 1]

[0117] In the bidentate ligand of each of the above uncharged, R, R, R, R, R, R, R, R, R

71 72 79 81 82 86 87 88 8 RRRR is an alkyl group, a cycloalkyl group, Ariru group, a heterocyclic group, or

9 95 96 97 98

It represents an aromatic heterocyclic group. R, R, R, R, R, R, R, R, R, R, R, R

73 74 76 77 78 83 84 90 92 93 99 A1 represents a substituent, RRRRRR represents a hydrogen atom or a substituent. nil is

75 80 85 91 94 AO

0 2 represents an integer, nl2 represents an integer of 0 3. nl3 represents an integer of 0 to 4. NL4 n 15 represents an integer of 0 3, NL6 represents 0 2 integer. nl7 represents an integer of 0 2, nl 8 is an integer of 0 3. nl9 represents an integer of 0 to 4. n20 n22 will table an integer of 0 2, n21 is an integer of 0 4. n23 represents an integer of 0 2, to display the 0 4 integer n24. QQQQ members of the

10 11 12 13 represents an atomic group for forming a 5 6 aromatic heterocyclic carbon with nitrogen.

[0118] In each uncharged bidentate ligand of the, RRRRRRRRR

71 Specific groups of 72 79 81 82 86 87 88 8 RRRR, the general formula (3) Aruke - similar to the R except Le group

9 95 96 97 98

Thing, and the like. R, R, R, R, R, R, R, R, R, R, R, R, R, R

73 The 74 76 77 78 83 84 86 90 92 93 99 A1 75 substituent RRRRR represented, the location where RR represents the general formula (1)

80 85 91 94

Those similar to the substituent can be mentioned. QQQQ has the same meaning as Q of the general formula (8).

[0119] Power mowing use in combination with the uncharged bidentate ligand is preferably minus monovalent § - The ON include the following

[0120] [of 22]

CI Br

0 0

One // - // one

oc sc sc

\ \ \

0 0

One t - + - +

0-S "R A8 0- SR A8

τ

ο

o ο

-Cow

0-ΒΓ - * - 0

+ One

0 ο

1 one

-BF -B -R

!

^ B2

[0121] In the formula, R represents an alkyl group, a cycloalkyl group, Ariru group, a heterocyclic group, or an aromatic double

A8

It represents a heterocyclic group. RR

A9, R

B0, Bl, R

B2 represents a Ariru group or an aromatic heterocyclic group.

[0122] Specific groups R are are the same as those described R excluding alkenyl groups of the general formula (3)

A8

That. R, R, R, specifically group R is Ariru group of the general formula (3), an aromatic heterocyclic group

A9 B0 Bl B2

It is listed in.

[0123] (no electricity monodentate ligand)

Te is your ヽ the present invention, the ligand uncharged ortho metal complex is B Gunkakara selected below, preferably have a Zureka.

[0124] [of 23] B group:

N≡C-- ft2 -N≡C-0- A2 - N≡C- S- R A - - N

-N -N (R M) N " " r- (f¾A4) n25

[0125] In the above B-gun, R, R, R, R, R represents an alkyl group, a cycloalkyl group, § Li

A2 A3 A5 A6 A7

Lumpur group, a heterocyclic group or an aromatic heterocyclic group. R represents a substituent, the n25 0 to 2

A4

It represents an integer selected from. R, R, R, R, specifically groups R, the formula (3)

A2 A3 A5 A6 A7

Aruke - those similar to the R except Le group. The substituent represented by R, the one

A4

R in general formula (1), those similar to the substituents represented by R.

1 11

[0126] Hereinafter, a preferred ortho metal complex used in the present invention.

[0127] [of 24] [S2 ^] [82 TO]

[92 ^] [62 TO]

]

[0132] [of 29]

[Οε ^] [εειο]

[0134] [of 31]

[0135] [of 32] [εε ^] [9ε TO]

[0137] [of 34]

These I 匕合 may, for example, Organic Leter, vol. 13, No. 16, p2579~2581 (2001), Inorganic Chemistry, vol. 30, No. 8, pl685~1687 (1991), J. A m . Chem. Soc., vol. 123, p4304 (2001), Inorganic Chemistry, vol. 41, No. 12, pl3056~3066 (2002), New Jounal of Chemistry, vol. 26, pl l 71 (2002), further It can be synthesized by applying the method of such references cited in these documents.

[0139] "applied to the organic EL element of the organic EL element material"

In the present invention, the organic EL device containing the organic EL device material, an organic EL in which the organic EL element material is contained in or forming the ヽ deviation of the organic layer constituting the organic EL element, or an organic layer It represents the element.

[0140] When applying the organic EL device material in an organic EL device of the present invention, characterized by comprising at least one layer of the layers constituting the organic EL elements, also has a light-emitting layer as a constituent layer, light emitting layer characterized in that it contains an organic-elect opening luminescent device material of the present invention to. Also has a hole blocking layer as a constituent layer preferably contains an organic elect port Rumine' sensing element material of the present invention to the hole blocking layer. Further, preferably contain at least greater carbazole Lumpur derivative of structure layers ヽ.

[0141] using an organic EL device material of the present invention, the case of manufacturing an organic EL element, in the constituting layers of the organic EL element (the details will be described later), good be used for the light-emitting layer or a hole blocking layer better not. Further, the light-emitting layer as described above, preferably used as a light emitting dopant.

[0142] (light-emitting host and the light-emitting dopant)

The mixing ratio of the light-emitting dopant to the emission host is Hosutoi 匕合 product is the main component in the light-emitting layer is that preferably adjusted to a range of 0.1 less than 30 wt% by mass.

[0143] However, the light emitting dopant opponent having different structures Yogu mixing be used by mixing plural kinds of compounds, also a phosphorescent dopant and a fluorescent dopant having other metal complexes or other structures good.

[0144] Herein, an optionally dopants in combination with a platinum complex used as a light emitting dopant (phosphorescent dopant, a fluorescent dopant, etc.). Emitting dopant, roughly, there are two types of phosphorescent dopants that emit fluorescent dopant and phosphorescent which emits fluorescence.

Representative examples of [0145] The former (fluorescent dopant), coumarin dyes, pyran based dyes, ShiRyoni emissions based dyes, Kurokoniumu dyes, Sukuariumu dyes, O Kiso Benz anthracene dyes, Furuoresein dyes, rhodamine system dye, pyrylium dyes, perylene dyes, styryl Reuben dyes, Porichiofen based dyes or rare earth complex based fluorescent material or the like, can be mentioned. [0146] As a typical example of the latter (phosphorescent dopant) is preferably 8 genus periodic table of the elements, 9 genus, complex compound containing 10 metals of, more preferably iridium compounds, O scan a Miumu compound is among the most favored U, the iridium compounds.

[0147] Specifically, a compound described in the following patent publications.

[0148] WO OOZ70655 Panfuretsu K JP 2002- 280178, JP 2001

- 181 616, JP 2002- 280179, JP 2001- 181617, JP 2002- 280180, JP 2001- 247859, JP 2002- 299060, JP 2001- 313178 , JP 2002- 302671, JP 2001- 345183, JP 2002- 324679, JP-WO 02,15645 No. pamphlet red, JP 2002- 332291, JP 2002- 50484 , JP 2002- 33 2292, JP 2002- 83684, JP-Kohyo 2002- 540572, JP 20 02 117 978, JP 2002- 338588, JP 2002- 170684 , JP-2002- 352960 JP, WO 01/93642 pamphlet, JP-2002

- 50483, JP 2002- 100476, JP 2002- 173674, JP-open 2002- 359082, JP 2002- 175884, JP 2002- 363552, JP 2002- 184582 , JP 2003- 7469 JP, Kohyo 2002- 525 808, JP 2003 7471 and JP-T-2002- 525833, JP 2003

- 31366, JP 2002- 226495, JP 2002- 234894, JP-open 2002- 235076, JP 2002- 241751, JP 2001- 319779, JP 2001- 319780 , JP 2002- 62824, JP 2002- 10 0474, JP 2002- 203679, JP 2002- 343572, JP-2 002- 203 678 JP like.

[0149] combination with the above ortho-metal complex is preferable according to the present invention! / The ヽ metal complex are shown below.

[0150] [of 35] lr-1 lr-2

36]

(Light-emitting host)

Emitting host (simply both host!, U) and means that the most often compounds the mixing ratio in the light emitting layer composed of two or more compounds (mass), "do in the case of other compounds one punt compound (also simply referred to as dopant) "called. For example, the light emitting layer I 匕合 compound A, composed of two of compound B, the mixing ratio is A: B = 10: If 90 Compound A is a dopant compound, the compound B is Hosutoi 匕合 product it is. Further emission layer I 匕合 A, Compound B, and three force structure of compound C, a mixture ratio of eight ^: Ji = 5: 10: 85 Deare words, Compound A, Compound B dopant compound There, the compound C is Hosutoi 匕合 thereof.

[0153] The luminescent host used in the present invention, the phosphorescent 0 0 bands phosphorescence 0 0 Ba preferred device emitting dopant compounds also have the same short wavelengths than command emitting dopant to be used in combination There when using a compound containing a blue emission component is 480nm or less, it is preferable as the light emitting host phosphorescent 0 0 band at 450nm or less.

[0154] as a light emitting host according to the present invention is not particularly limited in structure, typically Cal Bazoru derivatives, triaryl § amine derivatives, aromatic borane derivatives, nitrogen-containing heterocyclic of compounds, Chiofen derivatives, furan derivatives, have a basic skeleton such Origoariren compounds, and wherein 0 0 band power 50nm following compounds may be mentioned as preferred compounds. The light emitting host according to the present invention is also a low-molecular compound, but low molecular weight compound having a polymerizable group such as Yogu vinyl group and an epoxy group in polymerized compound having a repeating unit (an evaporation polymerizing emission host) ,,.

[0155] The light-emitting host, a hole transporting ability and an electron transporting ability, and prevents the longer wavelength of emission, noted and having a high Tg (glass transition temperature) is preferred.

[0156] Specific examples of the light emitting host, compounds described in the following references are preferred.

For example, JP 2001- 257076, JP 2002- 308855, JP 2001- 313179, JP 2002- 319491, JP 2001- 357977, JP-open 2002- 334786, JP- JP 2002- 8860, JP 2002- 334787 Patent Gazette, JP 2002- 15871, JP 2002- 334788, JP 2002- 4305 6, JP 2002- 33 9 No. , JP 2002- 75645, JP 2002- 338579, JP 2002- 105445, JP 2002- 343568, JP-open 2002- 141173, JP 2002- 352957, JP open 2002- 203683, JP 2002- 363227, JP 2002- 231453, JP 2003- 3 165, JP 2002- 234888, JP 2003- 27048, JP 200 2 255 934, JP 2002- 260861, JP 2002- 280183, JP 2002- 299060, JP 2002- 302516, JP 2002- 305083 JP JP 2002- 305084, JP-A No. 2002- 308837 Publication.

[0157] Next, there will be described a configuration of a typical organic EL device. [0158] "layers constituting the organic EL device"

Structure layer Nitsu of the organic EL device of the present invention, Te is described.

[0159] Preferred examples of the layer structure of the organic EL device of the present invention are shown below, but the invention is not limited to these.

[0160] (i) an anode Z-emitting layer Z electron transport layer Z cathode

(Ii) an anode Z hole transport layer Z emitting layer Z electron transport layer Z cathode

(Iii) anode Z hole transport layer Z emitting layer Z hole blocking layer Z electron transport layer Z cathode

(Iv) 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

"Light-emitting layer"

Contact to the present invention, Te is an organic EL device material of the present invention is preferably a This used Te you, the light-emitting layer, but the known luminescent host and emitting dopant as well the addition to these 併Choi and use.

[0161] Here, (improvement of emission luminance, the life of the emission lifetime) effects according to the present invention from the viewpoint of on further improvement and contains a compound emitting layer is represented by the following general formula (A) it is good or,. These compounds Contact to the light-emitting layer, is preferably used as the light emitting host Te.

[0162] [of 37]

- general formula (A)

^ 101 i \ IZ 2

,? -z 3 - - -c

In [0163] the above general formula (A), Z forms an aromatic heterocyclic ring which may have a substituent original

1

It represents element group, z is an aromatic heterocyclic ring which may have a substituent, or an aromatic hydrocarbon ring

2

Represents a forming atoms group, Z represents a divalent linking group or a single bond. R is hydrogen

3 101 atoms, or represents a substituent. [0164] Z, the aromatic heterocyclic ring represented atomic group power of Z is a furan ring, Chiofen ring, pyridinium

1 2

Jin 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, etc. Jiaza force carbazole ring (indicating the ring one of the carbon atoms of a hydrocarbon ring constituting a carboline ring is further substituted with a nitrogen atom) is and the like. Further, the aromatic heterocyclic ring may have a substituent represented by R described later.

101

[0165] The aromatic hydrocarbon ring represented by a group of atoms Z, a benzene ring, Bifue - Le ring,

2

Naphthalene ring, 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- Tel Hue - Le ring, Asenafuten ring , a coronene ring, a fluorene ring, fluoranthrene ring, naphthacene ring, a pentacene ring, a perylene ring, a pentaphene ring, a picene ring, a pyrene ring, pyranthrene ring, anthracite entrée down ring, and the like. Furthermore the aromatic hydrocarbon ring may have a substituent represented by R described later.

101

[0166] 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 (e.g., Hue - Rusuruho - Le group, Nafuchirusuruho - group, 2-Pirijirusuruho - Le group), amino group (e.g., amino group Echiruamino group, Jimechiruamino group, Puchiruamino group, Shikuropen Chiruamino group, 2-Echiru to Kishiruamino group, Dodeshiruamino group, § - Rinomoto, Nafuchirua amino group, 2-Pirijiruamino group), a halogen atom (e.g., fluorine atom, chlorine atom, a bromine atom), fluorinated hydrocarbon radicals (e.g., Furuoromechiru group, triflate Ruo Russia methyl, pen Tafuruoroechiru group, pentafluorophenyl - Le group), Shiano group, a nitro group, a hydroxyl group, a mercapto group, a silyl group ( For example, a trimethylsilyl group, triisopropoxide building silyl group, tri Hue - Rushiriru group, off - Rujechirushiriru group).

[0167] These substituents are further substituted with the substituents described above!, Even if I! /,. 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.

[0168] Examples of the divalent linking group include an alkylene, Aruke -, alkylene, other hydrocarbon groups such as Ariren, Yogumata Chiofen 2 also comprise heteroatoms, 5-di-I le radical Ya pyrazine 2, 3 Jiiru compound having an aromatic heterocyclic ring such as a group may be a divalent linking group derived from (also referred to as a hetero Kaoru aromatic compound), a force Rukogen atoms such as oxygen or sulfur, it may be. Further, alkylimino group, a hetero atom may be a group of linked gathered the like dialkylsilane Jiiru group Ya di § reel germane Jiiru group.

[0169] a single bond is a bond that binds to the substituent groups to each other directly linked.

[0170] In the present invention, the ring Z forms in the general formula (A) is preferably be a 6-membered ring

1

There. Thus, it is possible to increase more luminous efficiency. Furthermore it is possible to further long life. In the present invention, it is preferred ring Z forms is a 6-membered ring. This ensures that it is possible to increase more luminous efficiency. As possible out it is further longer life even more. Further With both 6-membered ring and Z and Z, it can be as high as more luminous efficiency

1 2

Since preferred. It preferred because it is possible to further longer life even more.

[0171] Hereinafter, specific examples of the compound represented by formula (A) according to the present invention, the present invention is not limited thereto.

[0172] Formula 38] Compound central skeleton A

[0173] [Formula 39] Compound central skeleton

40]

Compound central skeleton

41]

Compound

42] Compound central skeleton A

43]

[0178] [Formula 44] Compound central skeleton

45] compound central skeleton

46] compound central skeleton A

47] compound central skeleton A

48]

[0183] [of 49]

50]

51]

[0186] [of 52]

[0187] [of 53]

[F ^ [8810]

^ Fei 0 £ / 900Zdf / E :) d 01 1 ^ 8 £ 0I / 900Z OAV

[0189] [of 55]

[0190] [of 56]

[0191] [of 57]

[0192] [of 58]

[0193] [of 59]

[0194] [Formula 60] A- 121

61]

[0196] [of 62]

79

3874

[0197] [of 6

[0198] [of 64]

[0199] [of 65]

A- 147

66]

[0201] [of 67]

[89 ^] [2020]

^ Fei 0 £ / 900Zdf / E :) d turbocharger 8 1 ^ 8 £ 0I / 900Z OAV A- 158 A- 159

69]

[0204] [of 70]

A 170

[0205] [of 71] A one 171 A- 172

72]

Emitting layer according to the present invention, the above-mentioned compound, for example, vacuum deposition, spin coating, key Yasuto method, can be formed by a film by a known thin film I 匕法 such LB method. Thickness is not particularly limited as a light emitting layer, but usually selected in the range of 5nm~5 m. The light emission layer'll be a single layer structure also force the luminescent materials one or two or more! /, Then, Oh Rui be laminated structure comprising a plurality of layers of the same or different compositions! /ヽ. [0208] Further, the light-emitting layer as described in JP 57- 51781, JP-after the solution was 溶力 the light emitting material in a solvent together with a binder such as 榭脂, this it can be formed by thin film I spoon by a spin coating method. While such for the thickness of the light-emitting layer thus formed specifically limited, it can be appropriately selected depending on the Nag situation, usually in the range of 5 nm to 5 mu m.

[0209] "blocking layer: electron blocking layer, a hole blocking layer"

Blocking layer according to the present invention (e.g., an electron blocking layer, hole blocking layer) will be described. The preferred thickness of the blocking layer according to the present onset Akira 3: a LOOnm, more preferably Ru te at 5 to 30 nm o

[0210] (hole blocking layer)

In a broad sense, the hole blocking layer has the function of the electron transporting layer, the ability to transport holes while have a function of transporting electrons is significantly less material strength, deter hole while transporting electrons recombination probability of electrons and holes by can be improved.

[0211] In the present invention, the adjacent layer adjacent to the light-emitting layer, for example, a hole blocking layer, the electron blocking layer or the like, can be preferably used for an organic EL device material of the present invention to the hole blocking layer.

[0212] As the hole blocking layer, for example, JP-A 11 204 258 discloses, 11 204 359 JP Gazette, and "Organic EL Elements and Industrialization Front thereof (Nov. 30, 1998 E j 'tea' es Inc. issue) hole blocking according to page 237, etc. "(the hole blocking) layer and the like are applicable as the hole blocking layer according to the present invention. It can also be used as a hole blocking layer as required configuration of an electron transport layer described later, according to the present invention.

[0213] the hole blocking layer according to the present invention preferably contains the compound represented by the general formula (1). Further, the hole blocking layer according to the present invention, arbitrary preferred that contain boron derivative.

[0214] (electron blocking layer)

On the other hand, has the functions of hole transport layer in a broad sense, the electron blocking layer, while having the ability to transport holes ability to transport electrons are significantly less material strength, while transporting holes electrostatic it is possible to improve the probability of recombination of electrons and holes by inhibiting the child. Furthermore, it can be used as the electron blocking layer optionally the structure of a positive hole transport layer described later. [0215] In the present invention, the adjacent layer adjacent to the light-emitting layer, i.e. a hole blocking layer, the electron blocking layer, it is preferable instrument especially hole blocking using organic EL device material of the present invention described above it is preferable to use the layer.

[0216] "hole transport layer"

Comprise a material having a function of transporting holes from the hole transport layer, 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.

[0217] particularly limited nag conventionally as a hole transporting material, in Hikarishirubeden material, are conventionally used as a hole charge injection transporting materials, hole injection layer shall or EL elements, use the hole transport layer any from known those can be selected and used.

[0218] The hole transporting material is a hole injection or transport, electron barrier property! /, Are those having Zureka, organic, may be any of inorganic substance. For example, Toriazoru derivatives, O key Sajiazoru derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, off two Renjiamin derivatives, Ariruamin derivatives, amino-substituted chalcone derivatives, Okisazoru derivatives, styryl anthracene derivatives, Furuore non derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, Anirin based copolymer polymer, and an electroconductive oligomer, include especially Chio Fen oligomer.

[0219] 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,.

[0220] Representative examples of aromatic tertiary Amini 匕合 product and Suchiriruamini 匕合 thereof, N, N, N ', N' - Tetorafue - Le 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 - p Toriruaminofue - Le) propane; 1, 1-bis (4-di - p Torirua Minofue - Le) cyclohexane; N, N, N ', N' - tetramethyl one p-tolyl one 4, 4 '- diamine Nobifue - Le ; 1, 1-bis (4-di-one p Toriruaminofue - Le) 4 Hue - Rushikuro to key San; bis (4 - Jimechiruamino 2 Mechirufue - Le) phenylmethane, bis (4-di one p- Toriruaminofue - Le) Hue - Rumetan; N , N '- Jifue - Lou N, N' - di (4-methoxy Hue - Le) 4, 4 '- Jiaminobifue - le; N, N, N', N '- Tetorafue - Lou 4, 4' Jiaminojifu - ethers; 4, 4 '- bis (Jifue - Ruamino) Kuodorifue - le; N, N, N-tri (p-tolyl) Amin; 4- (di - p Toriruamino) - 4' - [4- (di - p DOO Riruamino) styryl] stilbene; 4-N, N Jifue - Ruamino - (2 Jifue - ruby ​​- Honoré) benzene; 3-methoxy ^ -N, N Ziff Eni Honoré aminostyryl Honoré benzene; N- phenylene carbazole, more having U.S. Patent No. 5, 061, 569 Pat two fused aromatic rings in the molecule described in, for example, 4, 4 'bis [N-(1-naphthyl) -N- Hue - Ruamino ] Bifue - Le (NPD), is described in JP-a-4 308 688 bird whistle - Rua Min unit is connected to three starburst 4, ', a "- tri scan [^ -? (3 - Mechirufue - Le) -N- Hue - Ruamino] bird whistle - Ruamin (MTDATA) and the like.

[0221] Furthermore it is also possible to use these materials are introduced in a polymer chain or 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. In the present invention, the hole transport material of the hole transport layer preferably has a fluorescence maximum wavelength below 415 nm, and still more preferably phosphorescent 0 0 band is 450nm or less. In addition, the hole transport material it is preferably a high Tg! / ,.

[0222] The hole transport layer, the hole transport material, for example, vacuum deposition, spin coating, casting method, an ink jet method, by a known method LB method, be formed by a thin film can. No particular limitation is imposed on the thickness of the hole transporting layer, but usually about 5 to 500 onm. The hole transport layer may have a single layer structure made of one or two or more of the above materials.

[0223] "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 at the Rukoto provided a single-layer or multiple layers.

[0224] 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), lower the serial of the materials are known. Further, the electron transport layer have a function of transporting electrons injected from the cathode to the emission layer Yogu as the material can be selected and used arbitrary from the compounds known in the art .

[0225] Examples of materials used for the electron-transporting layer (hereinafter, referred to as an electron transport material), - DOO port substituted fluorene derivatives, Jifuwe - Rukinon derivatives, Chio pyran dioxide derivatives, heterocyclic rings such as Na lid Ren perylene tetracarboxylic anhydride, a carbodiimide, Fureoreniri Denmetan derivatives, anthraquinodimethane and anthrone derivatives, and the like Okisajiazoru induction body. Further in the above Okisajiazoru derivatives, thiadiazole derivatives oxygen atom is replaced with a sulfur atom of Okisajiazo one Le ring, also quinoxaline derivative having knowledge obtained by! Ru quinoxaline as an electron withdrawing group are usable as the electron transporting material.

[0226] Furthermore it is also possible to use these materials are introduced in a polymer chain or a polymer having the material as the polymer main chain.

[0227] 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), and the like, and the central metal of these metal complexes There can be used in, Mg, Cu, Ca, Sn, as the metal complex is also an electron transporting material instead placed Ga or Pb. Other, even those Metarufuri mono- or metal phthalocyanine, or their ends are substituted with etc. alkyl group Ya sulfonic acid group, it 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. it can be an inorganic semiconductor is used as the electron transporting material.

[0228] The electron transporting layer is the electron transport material, for example, vacuum deposition, spin coating, key Yasuto method, an inkjet method, by a known method LB method, you to formed by a thin film it can. There is no particular limitation on the thickness of the electron transport layer, is usually about 5 to 5000 nm. The electron transport layer may have a single layer structure made of one or two or more of the above materials.

[0229] Next, used as a constituent layer of the organic EL device of the present invention, the injection layer is described

[0230] "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.

[0231] 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 industrial I匕 forefront (November 30, 1998 E j 2 Chapter 2 of 'tea' E, Inc. published) "" are described in detail in the electrode material "(page 123 to 166), a hole injection layer (anode buffer more) and an electron injection layer (cathode buffer there is and more).

[0232] 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

[0233] cathode buffer more (electron injection layer), JP-A 6 325 871 discloses, 9 17574 JP, are described also in detail in the 10-74586 discloses such, specifically stolons lithium more metal buffer typified Ya aluminum, Sani alkali metal compound buffer further represented by lithium fluoride, alkaline earth metal represented by magnesium fluoride group compound buffer further, typified by acid arsenide aluminum one layer such as a non-material buffers and the like.

[0234] The buffer further (injection layer) depends on a very thin layer in which it is desirable tool material but the thickness thereof is 0. 1: range of LOOnm is preferred.

[0235] The injection layer materials described above, for example, vacuum deposition, spin coating, casting, ink jet method, by a known method LB method, can be formed by thin film I spoon. No particular limitation is imposed on the thickness of the injection layer, but usually is about 5 to 5000 nm. Injection layer This may be a single layer structure is also one or two or more forces of the material.

[0236] "anode"

The anode of the organic EL device of the present invention, a large work function (4 eV or more) metals, an alloy, is preferably used a conductive compound and a mixture thereof as an electrode material. Specific examples of such an electrode material, metals such as Au, Cul, indium tin O Kishido (ITO), SnO, include a conductive transparent material such as ZnO are. Further, IDIXO (In O

2 2 3

It also used a material capable of producing a transparent conductive film -ZnO) spruce amorphous! ヽ. Anode to form a thin film by a method such as vapor deposition or sputtering of the electrode material, if not desired shape Yogu or pattern accuracy by forming a pattern with less required by photolithography (100 degrees or more m ), a 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, it has been sigma desirable to the transmittance greater than 10%, sheet resistance of the anode is preferably not less than several hundred ΩΖ port. Further thickness force usually 10 depending on the material: L000nm, is preferably selected in the range of 10 to 200 nm.

[0237] "cathode"

On the other hand, as a cathode according to the present invention, work (referred to as an electron injecting metal) function small (4 eV or less) metal, alloy, also the are using the electroconductive compound, or a mixture thereof as an electrode material. Specific examples of the electrode substance include sodium, monosodium force Liu arm alloy, magnesium, lithium, magnesium Z copper mixtures, magnesium Z silver mixture, a magnesium / aluminum mixture, magnesium Z indium mixture, aluminum Z Sani匕 aluminum (Al O) mixture, indium, a lithium Z aluminum mixture, dilute

twenty three

Earth metal, and the like. Among them, a mixture of a point of an electron injection property and durability against oxidation or the like, the second metals value 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, magnesium Z indium mixture, aluminum Z Sani匕 aluminum (Al O) mixed

2 3 thereof, lithium Z aluminum mixture, and aluminum. Cathode can be prepared by the method of vapor deposition or sputtering of these electrodes material to form a thin film. The sheet resistance several hundred Omega / mouth less preferably fixture thickness normally 10 as a cathode: L000nm, is preferably selected in the range of 50 to 200 nm. Herein, to transmit emission, either the anode or the cathode of the organic EL element, emission luminance is advantageous improved if transparent or translucent.

[0238] "substrate (substrate, the substrate, support or the like both! U)"

As the substrate according to the organic EL device of the present invention, the glass is not particularly limited as long particularly limited Nag also be of transparent type of plastic, is a preferred substrate for use, for example, glass, quartz, it may be mentioned optically transparent 榭脂 film. Particularly good or, substrates, Ru 榭脂 film Der capable of providing flexibility to the organic EL element.

[0239] 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 tri-acetate (TAC), and cellulose acetate propionate (CAP) Hitoshiryoku made film.

[0240] The surface of榭脂film, an inorganic or organic coating or a high Roh rear film High Priestess head coating Yogu water vapor permeability be formed is 0. 01gZm 2 'dayatm following both there it is preferable ヽ.

[0241] In the organic EL device of the present invention, the external extraction quantum efficiency of emission of the room temperature, more preferably preferably not less than 1% instrument is 2% or more. Here, the external extraction amount child Efficiency (%) = number of electrons X 100 that was run on the photon number Z organic EL device emitting organic EL device the outside.

[0242] Furthermore, it is possible to use a hue improving filter Chief of the color filter first class.

[0243] When used in lighting applications, it may be used in combination roughened films (anti-glare film or the like) in order to reduce the unevenness of light emission.

[0244] becomes organic EL element mosquito ゝ et having at least two different emission maximum wavelength is used as a multi-color display device, illustrating a preferred example of manufacturing an organic EL element.

[0245] "method for manufacturing the organic EL device"

As an example of a method for manufacturing an organic EL device of the present invention, an anode / hole injection layer / hole transport layer Z emitting layer Z HBL Z producing method of the electron-transporting layer Z cathode buffer more organic EL element consisting of Z cathode It will be described.

[0246] First a desired electrode material on a suitable substrate, for example, a thin film for an anode material force 1 mu m or less, preferably Iotaomikuron'itapai! To a film thickness of ~ 200 nm, it is formed by way of vapor deposition or sputtering or the like, to prepare an anode. Next, a hole injection layer, which is a device material on the hole transport layer, light emitting layer, a hole blocking layer, thereby made form a thin film containing an organic compound such as an electron-transporting layer.

[0247] As a method of a thin film I spoon of thin film containing the organic compound, a spin coating method as described above, a casting method, an ink jet method, evaporation method, a printing method, a uniform film can be obtained Ya immediately and from the viewpoint of the pinhole is formed with difficulty, vacuum deposition or spin coating is particularly preferred. Further it may apply different film method per layer. When employing the vapor deposition film, the deposition conditions may vary due to kinds of materials used, generally boat temperature 50 to 450 ° C, vacuum degree of 10- 6 ~: LO- 2 Pa, deposition rate 0 . 01~50NmZ sec, a substrate temperature of - 50 to 300 ° C, it is desirable to select appropriate thickness in the range of 0. lnm~5 μ m.

[0248] 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.

[0249] "display device"

Described display device of the present invention.

[0250] Display device of the present invention may be a multi-colored in a single color, here, describes a multicolor display device. For multicolor display device provided with a shadow mask only at the time of the light emitting layer formation, vapor fusing method, a casting method on one surface, a spin coating method, an inkjet method, the film can be formed by a printing method or the like.

[0251] Although there is no limitation to the method when performing patterning only the light-emitting layer is preferably a vapor deposition method, an inkjet method, a printing method. In the case of using the evaporation method, the putter was used shadow mask - ring are preferred. Further, reversing the preparation order, a cathode, an electron transport layer, a hole blocking layer, an emission layer, a hole transport layer, it is also possible to prepare the order of the anode.

[0252] When a DC voltage is applied to such multi-color display device obtained in the anode to +, cathode - polarity voltage of approximately 2~40V the emission can be observed applied as the. Also, quite occur it! / ヽ luminescent not current flows even if a voltage is applied in reverse polarity. Furthermore, when an AC voltage is applied, the anode +, cathode - emits light only in a state. The waveform of the applied alternating current Yo optionally.

[0253] multicolor display device display devices, displays, Ru can be used as various light emission sources. The display device or the display, blue, red, by are use three kinds of organic EL elements of green light emission, it is possible to display full color.

[0254] 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.

[0255] home lighting as a light emission source, interior lighting, backlight of a watch or a liquid crystal, a panel advertisement, traffic lights, light sources of optical storage medium, an electrophotographic copying machine of a light source, an optical communication processor source, the light sensor light source and the like but not limited thereto.

[0256] "lighting device"

It illustrates lighting device of the present invention.

[0257] The intended use of the organic EL element having a resonator structure such as Yoguko be used in an organic EL element as the organic EL element having a resonator structure of the present invention, the optical storage medium source, an electrophotographic copying machine of the light source for an optical communication device of the light source, the power source for a photo-sensor, but are not limited thereto. Also by the laser oscillation, it may be used for the above applications.

[0258] Further, the organic EL device of the present invention one may use as a lamp such as a lighting lamp or a light source for exposure, the type of and project Chillon apparatus for projecting an image, still images and moving images it may be used as a display device of a type in which direct visualization (display). , Either in an active matrix method in a simple matrix (passive matrix) method driving method when used as a display device for video playback. Or an organic EL device of the present invention having different emission colors by using two or more, it is possible you to produce a full-color display device.

Will be described with reference [0259] An example of the organic EL device power composed display device of the present invention with reference to the accompanying drawings

[0260] FIG. 1 is a schematic view showing an example of an organic EL element mosquito ゝ et configured 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.

[0261] Display 1, also the control unit B Hitoshiryoku which performs image scanning in the display section A based on the display section A, the image information having a plurality of pixels.

[0262] The control unit B is electrically connected to the display section A, transmits a scanning signal and an image data signal based on image information from the outside to each of the plurality of pixels, image elements of each scanning line image by a scanning signal displaying the image information on the display unit a performs image scanning which emits light corresponding to the data signal.

[0263] FIG. 2 is a schematic drawing of a display section A.

[0264] 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.

[0265] 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).

[0266] pixel 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.

[0267] Next, an emission process of pixels will be explained.

[0268] FIG. 3 is a schematic diagram of a pixel.

[0269] pixel comprises an organic EL element 10, a switching transistor 11, the driving transistor 12, 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 emission, full color display can be performed by side by side on the same substrate.

[0270] 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.

[0271] 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.

[0272] 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.

[0273] That is, the light emitting a plurality of pixels each organic EL element 10 of the organic EL element 10, provided with a switching transistor 11 and driving transistor 12 which is an active element, a plurality of pixels 3 each organic EL element 10 emitting a go of, Ru. Call such a light emitting method and § click Restorative matrix method, Ru.

[0274] 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! /,.

[0275] The retention of the potential of the capacitor 13, be held to continue till the next application of the scanning signal! , And then be discharged immediately before the next scanning signal is applied!,.

[0276] 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.

[0277] FIG. 4 is a schematic view of a display device according to the notch inclusive matrix system. 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.

[0278] 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. No active elements picture element 3 in notch Shiv matrix system, which reduces manufacturing cost.

[0279] The organic EL device material of the present invention, also, as a lighting device can be applied to the organic EL element which emits light of substantially white. Obtain white light by color mixing simultaneously emit light a plurality of emission colors by a plurality of light-emitting materials. As a combination of the plurality of emission colors, using blue, green, may be one which contains three light-emitting maximum wavelength of the blue of the three primary colors, blue and yellow, the complementary color relationship such as blue-green and orange color 2 one of or one containing the light-emitting maximum wavelength.

[0280] 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 It may be either although the light combining the dye material which emits light as an excitation light from the light emitting material, in the white organic EL device according to the present invention, combining a plurality of light-emitting dopant system is preferred.

[0281] The layer structure of the organic EL element to obtain a plurality of emission colors, a plurality of light emitting dopant, a method for more present in one light emitting layer, a plurality of light-emitting layers, in each light-emitting layer method for each occurrence of light emission wavelengths of different dopants, and a method of forming a micro-pixel emitting a different wavelength in a matrix.

[0282] In the white organic EL device according to the present invention, the putter a metal mask Ya I inkjet printing method or the like at the time of film formation needed - be subjected to ring. If you putter Jung, to only electrodes okay to putter Jung, to the electrode and the light emitting layer okay to putter Jung okay to putter Jung elements all layers. [0283] used for the light-emitting layer Nag particular limitation is imposed on the luminescent material, e.g., if the put that Bruno backlight to the liquid crystal display device, CF (color filter) to match the wavelength range corresponding to the characteristic, known light emitting materials it may be white by combining selected ones of Churyoku any.

[0284] Thus, the white light-emitting organic EL device is the display device, in addition to the display, the seed light emission source, a lighting device, home lighting, interior lighting, and as one of the lamps, such as the exposure light source, backlight of a liquid crystal display device, used in useful to a display device.

[0285] 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, the light sensor light source or the like, and further requires a display device etc. general household appliances to include a wide range of applications.

Example

[0286] The present invention will be described by way of examples, but the present invention is not limited thereto.

[0287] Example 1

"Fabrication of organic EL element"

Preparation of the organic EL element OLED1- 1]

Substrate and ITO was 150nm deposited on glass as an anode (NH Techno Glass: NA- 45) after the putter Jung, ultrasonic cleaning the transparent substrate having the ITO transparent electrode in iso propyl alcohol净, dried with dry nitrogen gas, a UV ozone cleaning ivy line 5 minutes. This transparent support substrate was fixed on a substrate holder of a vacuum deposition apparatus available on the market, whereas, five tantalum resistance 卩熱 boat, a- NPD, CBP, Ir- 12, BCP, and Alq it

3 Each placed, attached to a vacuum vapor deposition apparatus (a first vacuum chamber).

[0288] Further, lithium fluoride tantalum resistance heating boat, placed respectively aluminum to tungsten resistance heating boats were attached to the second vacuum chamber of a vacuum deposition apparatus.

[0289] 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.

Adjusted to 7: [0290] Further deposition rate is Ir- 12 in CBP with emission dopant which is a light-emitting host energized the boat containing the heating boat and Ir 12 containing the CBP independently 100 and deposition to a layer thickness of 30 nm, which a light-emitting layer.

[0291] then heated by supplying an electric current to the heating boat containing BCP, form a hole blocking layer of deposition rate from 0.1 to 0. Thick lOnm in 2n mZ seconds. Further passing said heated boat containing Alq

3

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

[0292] Next, after transferring film to an element in the second vacuum chamber while the vacuum to the electron transport layer as, on the electron transport layer, so that the stainless steel rectangular perforated mask is placed was installed by remote control from instrumentation 置外 part in.

[0293] 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 device OLED1- 1.

[0294] [of 73]

[0295] Preparation of the organic EL element OLED1- 2~1 20]

In the preparation of the organic EL element OLED1- 1, the light emitting dopant as described in Table 1, except for changing the light emitting host, a hole blocking material, an organic EL device was prepared OLED1- 2~ 1- 20 in a similar manner .

[0296] "Evaluation of Organic EL element"

The obtained organic EL device OLED1- 1~1 20 Nitsu, Te was evaluated as follows.

[0297] (Measurement of external extraction quantum efficiency)

The organic EL device OLED1- 1~1- 20, the room temperature (about 23~25 ° C), 2. performs lighting by constant current conditions 5mAZcm 2, lighting start immediately after the emission luminance (L) [cdZm 2] It was calculated external extraction quantum efficiency (r?) by measuring. The measurement of emission luminance, CS - 1000 - a (co Minolta Sensing, Inc.) was used. The external extraction quantum efficiency represented a organic EL element OLED1- 1 as a relative value is 100.

[0298] (Measurement of emission lifetime)

The organic EL device OLED1- 1~1 20, at room temperature, 2. performs continuous lighting by constant current conditions 5MAZcm 2, the time required to becomes half of the initial luminance (tau

1/2) was measured. The emission lifetime is expressed by a relative value when the organic EL element OLED 1-1 and 100.

The results obtained by the [0299] above, are shown in Table 1.

[0300] [Table 1]

The organic EL light emitting external extraction emission lifetime

Hole blocking material Remarks element No. phosphorylase Bok dopant quantum efficiency <, Te)

OLEDI- 1 CBP lr-12 BCP 100 100 comparisons

OLEDI -2 CBP lr-11 BCP 102 103 comparisons

OLEDI -3 CBP 2 BCP 122 198 the invention

OLEDI - - CBP 6 BCP 128 203 the invention

OLEDt-5 CBP 10 BCP 126 190 the invention

OLEDI -6 CBP 11 BCP 124 197 the invention

OLEOI-7 CBP 20 BCP 120 206 the invention

0 Mr EDt -8 CBP 30 BCP 128 195 the invention

OLEDI -9 ACZ1 41 BCP 136 220 the invention

OLEDI -10 ACZ1 48 BCP 133 218 the invention

OLEDI -11 ACZ2 39 BCP 131 230 the invention

OLEDI -12 ACZ2 53 BCP 136 233 the invention

OLEDI -13 CBP 33 ACZ1 140 244 the present invention

OLEDI-, 4 CBP 38 ACZ2 139 250 the invention

OLEDI- 15 CBP 86 BCP 118 187 the invention

OLEDI- 16 CBP 93 BCP 117 183 the present invention

OLED! -17 ACZ1 82 BCP 130 210 the present invention

OLEDI- 18 ACZ2 83 BCP 132 213 the present invention

0LE0t ~ 19 CBP 87 ACZ1 139 231 the present invention

OLEDI one 20 CBP 90 ACZ2 137 228 the invention

[0301] As is apparent from the results set forth in Table 1, the organic EL element manufactured using the ortho metal complex according to the present invention, compared to the comparative organic EL element, the life of the high luminous efficiency and emission lifetime it is clear that that can be achieved.

[0302] Furthermore at least one of the carbon atoms of the hydrocarbon ring constituting a carboline ring of carboline derivatives or the carboline derivatives, be used together derivative that having a ring structure that is further substituted with a nitrogen atom to the light-emitting layer Accordingly, also at least one carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives or the carboline derivative conductor, the use of derivatives having a ring structure which is substituted with more nitrogen atom in the hole blocking layer Accordingly, it could be confirmed that the improvement of the effects described can be obtained with the present invention.

[0303] Example 2

"Preparation of a full-color display device"

(Preparation of blue light emitting element)

Using the organic EL element OLED1- 4 according as a blue light-emitting element in Example 1.

[0304] In the preparation of the organic EL element OLED1- 4 according to (green light emitting Preparation of elements) Example 1, in place of the Ir- 12, except for using Ir-1 as a green light-emitting dopant in the same manner, to produce a green light emitting element

[0305] (Preparation of red light-emitting element)

In the preparation of the organic EL element OLED1- 4 described in Example 1, in place of the Ir- 12, except for using Ir- 9 as red light-emitting dopant in the same manner to produce a red light emitting element

[0306] Red prepared above, green, juxtaposing the organic EL element of blue emission on the same substrate, papermaking create an active matrix type full-color display device having a form as described in Figure 1, Figure 2 It showed only schematic drawing of a display section a of the display device manufactured in. That is, a plurality of pixels 3 (the color of light emission pixels in the red area, the pixels of the green region, pixels etc. blue region) juxtaposed with wiring section containing plural scanning lines 5 and plural data lines 6 on the same substrate and 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 organic EL elements corresponding to the respective emission colors, respectively sweep rate Tsu quenching transistor and the drive transistor is driven in an active matrix scheme provided an active element, the scanning signal is applied from the scanning lines 5 is the the receive image data signals 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.

[0307] By driving the full color display device, light emission luminance has a high ingredients high durability, it was possible to confirm that 且 one sharp full-color video display can be obtained.

[0308] Example 3

"Preparation of a full-color display device"

In the preparation of a full-color display device according to Example 2, in place of the organic EL element OLED1- 4 is a blue light-emitting element, except for using the organic EL element OLED1- 6, full-color display device in the same manner as in Example 2 It was produced. By driving the full color display device, light emission luminance has a high ingredients high durability, and sharp full-color moving image display has been found to obtain Rukoto. [0309] Example 4

"Preparation of a full-color display device"

In the preparation of a full-color display device according to Example 2, in place of the organic EL element OLED1- 4 is a blue light-emitting element, except for using the organic EL element OLED1- 13, full-color display device in the same manner as in Example 2 It was produced. By a child driving the full color display device, light emission luminance has a high ingredients high durability, and sharp full-color video display was found that the obtained al.

[0310] Example 5

"Preparation of a full-color display device"

In the preparation of a full-color display device according to Example 2, in place of the organic EL element OLED1- 4 is a blue light-emitting element, except for using the organic EL element OLED1- 14, full-color display device in the same manner as in Example 2 It was produced. By a child driving the full color display device, light emission luminance has a high ingredients high durability, and sharp full-color video display was found that the obtained al.

[0311] Example 6

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

Implementing the transparent electrode substrate of the electrode according to Example 1 and putter Jung to 20 mm X 20 mm, and a film of a- NPD as a hole injection / transport layer in the same manner as in Example 1 thereon at a thickness of 25 nm, further It energized CBP of containing said heating boat and the present compound 20 of containing boat and the incoming ivy boat Ir 9 each independently exemplified compound 20 and Ir- of the invention that are CBP and the light emitting dopant which is a light-emitting host deposition rate of 9 100: 5: adjusted to 0.6, was deposited to a thickness of a film thickness 30 nm, which a light-emitting layer.

[0312] Next, in, form a hole blocking layer and lOnm film forming of BCP. In addition to film the Alq in 40nm

3

An electron transporting layer.

[0313] Next, a square perforated mask having substantially the same shape as the stainless steel of the transparent electrode was placed on the electron injection layer in the same manner as in Example 1, as lithium fluoride 0. 5 nm, and a cathode as a single layer cathode buffer aluminum 150nm was deposited film forming.

[0314] The device was fabricated flat lamp is provided with a sealing can in a similar manner and similar structure as in Example 1. It shows a schematic view of a planar lamp 5, 6. The schematic diagram in Figure 5 shows a cross-sectional view in FIG. Almost white light obtained was energized to this plane lamp, it was able to be used as a lighting device.

[0315] 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, Example Compound 20 of the present invention, except for changing the exemplified compound 30 was produced white illumination device in the same manner as in Example 6. This nearly was energized plane lamp white light was obtained, it was not Kotogawa be used as a lighting device.

[0316] 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, Example Compound 20 of the present invention, except for changing the exemplified compound 39 was produced white illumination device in the same manner as in Example 6. This nearly was energized plane lamp white light was obtained, it was not Kotogawa be used as a lighting device.

[0317] 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) / Exemplified Compound 6 (blue luminescent Orutome barrel complex) of the present invention / tris (2-Hue - Norepirijin) iridium complex (green luminescent orthometalated complex: I r 1) Z bis (2-Benzochiofen [b] - 2-Ino rate pyridine) § Se Chino rare Setona Toys Rijiumu complex (red luminescent orthometal complexes: Ir- 9) Z2- (4- Bifue - Lil) - 5-(4 t Buchirufue - Le) 1, 3, 4-O hexa di § tetrazole (electron transporting material) = 200Z2Z5 / 2/50 dichloroethane solution of the mass ratio a spin - data - in applying, emission of lOOnm It was to give a layer.

[0318] The putter Jung the mask on the organic compound layer was placed (emission area mask to be 5 mm X 5 mm), 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 with. To produce a light-emitting element out a © beam leads - anode, respectively § Rumi from the cathode. The element was placed in grayed port blanking box purged with nitrogen gas, an ultraviolet curing adhesive with a glass sealing container (Nagase Ciba, XNR5493) to prepare a planar lamp sealed with. This was energized plane ramp substantially white light is obtained around, I can be used as a lighting device ChikaraTsuta.

[0319] 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, Example Compound 6 of the present invention, except for changing the exemplified compound 11 was produced white illumination device in the same manner as in Example 9. This was energized plane lamp is substantially white light is obtained, we see that that can be used as an illumination device ivy o

[0320] 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, Example Compound 6 of the present invention, except for changing the exemplified compound 52 was produced white illumination device in the same manner as in Example 9. This was energized plane lamp is substantially white light is obtained, we see that that can be used as an illumination device ivy o

[0321] 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) / Exemplary Compound 41 (blue luminescent orthometalated complex) of the present invention Z tris (2 Hue - Rubirijin) iridium complex ( green luminescent orthometal complexes: Ir- 1) Z bis (2 - Benzochiofen [b] - 2-I le Ichipi lysine) Asechiruasetona - DOO iridium complex (red luminescent orthometal complexes: Ir- 9) / 2 - ( 4 Bifue - Lil) - 5-(4-t-Buchirufue - Le) - 1, 3, 4 Okisajiazo - dichloroethane was dissolved Le (electron transporting material) = 150/50/2/5/2/50 mass ratio the solution scan Binko - data - in applying, to obtain a light-emitting layer of LOOnm.

[0322] On the organic compound layer was placed a mask (mask emission area ing and 5 mm X 5 mm) was Notayungu, aluminum 150nm as lithium fluoride 0. 5 nm, and a cathode as a single layer cathode buffer in the deposition apparatus provided with a cathode was deposited. To produce a light-emitting element out a © beam leads - anode, respectively § Rumi from the cathode. The element was placed in grayed port blanking box purged with nitrogen gas, an ultraviolet curing adhesive with a glass sealing container (Nagase Ciba, XNR5493) to prepare a planar lamp sealed with. This was energized plane ramp substantially white light is obtained around, it can be confirmed that it can be used as a lighting device.

[0323] 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, Example Compound 41 of the present invention, except for changing the instantiated compound 39, to produce a white illumination device in the same manner as in Example 12. Almost white light obtained was energized to this plane lamp, it was able to be used as a lighting device.

[0324] 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 hole transport control material ACZ1 Change in ACZ2 was prepared white illumination device in the same manner as in Example 12. Almost white light obtained was energized to this plane lamp, it can be used as a lighting device ChikaraTsuta.

[0325] Example 15

"Preparation of Organic EL element OLED2- 1~2- 13"

In the preparation of the organic EL element OLED1- 1 described in Example 1, to change the light emitting dopant Ir 1, a hole blocking material in the same manner except for changing as described in Table 2, the organic EL element OLED2- 1~2- 13 were produced. External taken out quantum efficiency of the organic EL device obtained were each conducted in the same manner as described in Example 1 to measure the light emission life. At this time, both the value of the organic EL element OLED2- 1 as 100, representing the value of each organic EL element relative value. The results obtained are shown in Table 2.

[0326] [Table 2] Organic EL external extraction emission Pride goes

Hole blocking material Remarks

Device No. quantum efficiency (gamma

0LED2-) BCP 100 100 comparisons

0LED2-2 2 116 250 the invention

0LED2-3 6 115 25! The present invention

0LED2-4 15 117 255 the present invention

0LED2-5 21 116 254 the present invention

0LED2-6 31 115 253 the invention

0LED2-7 40 117 252 the present invention

0LED2-8 52 115 251 the invention

OLE02-9 64 118 253 the present invention

0 67 113 247 the present invention

74 116 250 the present invention

0LED2-12 84 115 248 the present invention

From 0LED2-13 96 117 246 present invention Table 2, the organic EL element using an organic EL device material in the hole blocking material of the present invention, compared to a ratio 較素Ko, found that high luminous efficiency and emission life can be obtained It was. The emission color of the organic EL device of the present invention were all green.

Claims

Organic elect port luminescent element material to feature in that it contains an ortho metal complex having a partial structure represented by the range following formula according (Z).
[Formula 1]
The general formula (Z)
Wherein, X represents a 0, S, SO, or SO, X is a divalent group or a single bond. R is location
Representing a 2 1 a substituent. R
b represents a hydrogen atom or a substituent. L forms a Fang aromatic heterocyclic 5- to 7-membered together with the nitrogen atom. M is to display the groups 8 to 10 of the metal element in the periodic table. ]
Partial structure represented by the general formula (Z) is an organic elect port luminescent device material according to the range first of claims, wherein the partial structure der Rukoto represented by the following general formula (1)
[Formula 2]
The general formula ( "
Wherein, X represents a 0, S, SO, or SO, R represents a substituent. R is a hydrogen atom or
10 2 1 2
It represents a substituent. Represents X, X, X, X are each C, C- R, N, N- R, O or S,
11 12 13 14 11 11 and form a heteroaromatic ring 5-membered together with the nitrogen atom. R represents a hydrogen atom or a substituent. M represents a Group 8 to Group 10 metal element in the periodic table. ] Partial structure represented by the above general formula (Z) is an organic elect port luminescent device material according to the range first of claims, wherein the partial structure der Rukoto represented by the following general formula (2)
[Formula 3] Formula (2)
Wherein, X represents a 0, S, SO, or SO, R represents a substituent. R is a hydrogen atom or
20 2 3 4
It represents a substituent. X, X, X, X each represents C-R or N, and the carbon atoms, nitrogen
21 22 23 24 21
To form a 6-membered aromatic heterocyclic ring with the atom. R represents a hydrogen atom or a substituent
twenty one
. M represents a Group 8 to Group 10 metal element in the periodic table. ]
Partial structure represented by the general formula (Z) is an organic elect port luminescent device material according to the range first of claims, wherein the partial structure der Rukoto represented by the following general formula (3)
[Formula 4]
- general formula (3>
Wherein, X represents a 0, S, SO, or SO, R represents a substituent. R is a hydrogen atom or
It represents a 30 2 5 6 substituents. Represents X, X, X, X are each C, C- R, N, N- R, O or S,
31 32 33 34 31 31
And form a heteroaromatic ring 5-membered together with the nitrogen atom. R is a hydrogen atom or a substituent
31
A representative. X is 0, S, CH, CHR, C (R), NR, PR, Si (R), C = 0, C = NR, SO,
0 2 2 2
Representing the SO. R is an alkyl group, a cycloalkyl group, an alkenyl group, Ariru group, a heterocyclic
2
It represents a group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table. ]
Partial structure represented by the general formula (Z) is an organic elect port luminescent device material according to the range first of claims, wherein the partial structure der Rukoto represented by the following general formula (4)
[Of 5]
The general formula (4)
Wherein, X represents a 0, S, SO, or SO, R represents a substituent. R is a hydrogen atom or
It represents the 40 2 7 8 substituents. X, X, X, X each represents C-R or N, and the carbon atoms, nitrogen
41 42 43 44 41
To form a 6-membered aromatic heterocyclic ring with the atom. R represents a hydrogen atom or a substituent
41
. X is 0, S, CH, CHR, C (R), NR ゝ PR, Si (R), C = 0, C = NR, SO, and SO
0 2 2 2 2 represents. R is an alkyl group, a cycloalkyl group, Aruke - represents a group, Ariru group, the heterocyclic group or aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table. ]
[6] partial structure represented by the general formula (2) An organic elect port luminescence to in paragraph 3 of claims, wherein the partial structure der Rukoto represented by the following general formula (5) element material [of 6]
Common
[Wherein, R represents a substituent, R represents a hydrogen atom or a substituent. When the least of R and R
51 52 51 52 one of which is electron-donating substituent or an electron-withdrawing group. X is o, s,
51 represents the so or SO. R represents a substituent, n51 is an integer selected from 0-3. Xa is
2 50
-N (Ra), -O-Ra or - represents an S-Ra. Ra represents an alkyl group, a cycloalkyl group,
2
An alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. If Xa Gar N of (Ra), 2 two Ra may be different even in the same. M is in the periodic table
2
It represents a Group 8 to Group 10 metal element. ]
Partial structure represented by the general formula (4) An organic elect port luminescent device material according to claim 5, wherein according to said partial structure der Rukoto represented by the following general formula (6)
[Formula 7] General formula (6)
[Wherein, R represents a substituent, R represents a hydrogen atom or a substituent. When the least of R and R
56 57 56 57 also one is an electron-donating substituent or an electron-withdrawing group. X is
52 o, s, it represents the so or SO. R represents a substituent, n52 is an integer selected from 0-3. Xa is
2 55
-N (Ra), -O-Ra or - represents an S-Ra. Ra represents an alkyl group, a cycloalkyl group,
2
An alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. If Xa Gar N of (Ra), 2 two Ra may be different even in the same. X is 0, S, CH, CHR,
2 0 2
C (R), represents NR, PR, Si (R), C = 0, C = NR, SO, and 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.
M represents a Group 8 to Group 10 metal element in the periodic table. ]
Partial structure represented by the general formula (1) is represented by the following general formula (7A) or the general formula organic elect port in claim 2, characterized in that in (8A) is a partial structure table Ruminesse Nsu element material.
[Of 8]
- general formula (7A) - general formula (8A)
[In the formula, X, X, X, X
61 62 63 64 each represent a carbon atom or a nitrogen atom, Q
1 carbon atom, X
Represents an atomic group forming an aromatic heterocyclic ring of 5 members together X, Q are carbon atoms, X, X
61 62 2 63 64
Represents an atomic group forming an aromatic heterocyclic ring of 5 members together with the nitrogen atom. X, X is 0, S, S
1 2
It represents O or SO. R represents a substituent, R represents a hydrogen atom or a substituent. R,
2 15 26 16
R, R, R van der Waals volume of 20
17 represents a substituent is 25 27 A 3 or more. n61, n6
2, n63 is 0 or 1. However, it is n61 + n62≥l. M represents a Group 8 to Group 10 metal element in the periodic table. ]
[9] Organic partial structure represented by the general formula (2) is in the range 3 preceding claims, characterized in that a partial structure table by the following general formula (7B) or the general formula (8B) elect opening Ruminesse Nsu element material.
[Formula 9] Formula (8B)
[Represents wherein, X, X, X, X is each a carbon atom or a nitrogen atom, Q is a carbon atom, X
63
Represents an atomic group forming an aromatic heterocyclic 6-membered together X, Q are carbon atoms, X, X
2
Represents an atomic group forming an aromatic heterocyclic 6-membered together with the nitrogen atom. X, X is 0, S, S
2
It represents O or SO. R represents a substituent, R represents a hydrogen atom or a substituent. R,
2 15 26 16
R, R, R represents a substituent van der Waals volume is 20 A 3 or more. n61, n6
17 25 27
2, n63 is 0 or 1. However, it is n61 + n62≥l. M represents a Group 8 to Group 10 metal element in the periodic table. ]
Partial structure represented by the general formula (3) is an organic elect according to claim 4, characterized in that a partial structure represented by the following general formula (9A) or the general formula (10A) mouth luminescent element material.
[Of 10] General
[Represents wherein, X, X, X, X is each a carbon atom or a nitrogen atom, Q is a carbon atom, X
71 72 73 74 3
Represents an atomic group forming an aromatic heterocyclic ring of 5 members together X, Q are carbon atoms, X, X
71 72 4 73 74
Represents an atomic group forming an aromatic heterocyclic ring of 5 members together with the nitrogen atom. X, X is 0, S, S
3 4
It represents O or SO. R represents a substituent, R represents a hydrogen atom or a substituent. R, R, R, R represents a substituent van der Waals volume is at 20A 3 or more. n71, n7
37 45 47
2, n73 is 0 or 1. However, it is n71 + n72≥l. X is 0, S, CH, CHR, C
0 2
(R), represents NR, PR, Si (R), C = 0, C = NR, SO, and SO. R is an alkyl group, a cycloalkyl
2 2 2
Alkyl group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table. ]
Partial structure represented by the general formula (4) is an organic elect according to claim 5, characterized in that a partial structure represented by the following general formula (9B) or the general formula (10B) mouth luminescent element material.
[Of 11] General
[Represents wherein, X, X, X, X is each a carbon atom or a nitrogen atom, Q is a carbon atom, X
71 72 73 74 3
Represents an atomic group forming an aromatic heterocyclic 6-membered together X, Q are carbon atoms, X, X
71 72 4 73 74
Represents an atomic group forming an aromatic heterocyclic 6-membered together with the nitrogen atom. X, X is 0, S, S
3 4
It represents O or SO. R represents a substituent, R represents a hydrogen atom or a substituent. R,
2 35 46 36
R, R, R represents a substituent van der Waals volume is 20 A 3 or more. n71, n7
37 45 47
2, n73 is 0 or 1. However, it is n71 + n72≥l. X is 0, S, CH, CHR, C
0 2
(R), represents NR, PR, Si (R), C = 0, C = NR, SO, and SO. R is an alkyl group, a cycloalkyl
2 2 2
Alkyl group, an alkenyl group, Ariru group, a heterocyclic group or an aromatic heterocyclic group. M represents a Group 8 to Group 10 metal element in the periodic table. ]
[12] The M in the general formula (Z) is an organic elect port luminescent device material according to claim 1, characterized in that iridium or platinum.
[13] The organic-elect opening luminescent device material according to claim 1, organic-elect opening luminescent element characterized by containing the first layer even without less of constituent layers.
[14] a light-emitting layer as a constituent layer, organic elect port luminescent element of the light-emitting layer, characterized in that it contains an organic-elect opening luminescent device material according to claim 1.
[15] display device characterized by having an organic-elect opening device as described in Claim 13.
[16] an illumination apparatus characterized by having an organic-elect opening device as described in Claim 13.
PCT/JP2006/304234 2005-03-29 2006-03-06 Organic electroluminescent device material, organic electroluminescent device, display and illuminating device WO2006103874A1 (en)

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