WO2005123873A1 - 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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WO2005123873A1
WO2005123873A1 PCT/JP2005/010552 JP2005010552W WO2005123873A1 WO 2005123873 A1 WO2005123873 A1 WO 2005123873A1 JP 2005010552 W JP2005010552 W JP 2005010552W WO 2005123873 A1 WO2005123873 A1 WO 2005123873A1
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general formula
represents
organic
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layer
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Japanese (ja)
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Tomohiro Oshiyama
Masato Nishizeki
Eisaku Katoh
Hiroshi Kita
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Konica Minolta Holdings, Inc.
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Publication of WO2005123873A1 publication Critical patent/WO2005123873A1/en

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    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0084Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H01L51/0085Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising Iridium
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0084Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H01L51/0087Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05BELECTRIC HEATING; ELECTRIC LIGHTING NOT OTHERWISE PROVIDED FOR
    • H05B33/00Electroluminescent light sources
    • H05B33/12Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18Metal complexes
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/005Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene
    • H01L51/0059Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H01L51/006Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
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    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/005Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene
    • H01L51/0062Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene aromatic compounds comprising a hetero atom, e.g.: N,P,S
    • H01L51/0071Polycyclic condensed heteroaromatic hydrocarbons
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    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/005Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene
    • H01L51/0062Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene aromatic compounds comprising a hetero atom, e.g.: N,P,S
    • H01L51/0071Polycyclic condensed heteroaromatic hydrocarbons
    • H01L51/0072Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ringsystem, e.g. phenanthroline, carbazole
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
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    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0079Metal complexes comprising a IIIB-metal (B, Al, Ga, In or TI), e.g. Tris (8-hydroxyquinoline) gallium (Gaq3)
    • H01L51/008Metal complexes comprising a IIIB-metal (B, Al, Ga, In or TI), e.g. Tris (8-hydroxyquinoline) gallium (Gaq3) comprising boron
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
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    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0079Metal complexes comprising a IIIB-metal (B, Al, Ga, In or TI), e.g. Tris (8-hydroxyquinoline) gallium (Gaq3)
    • H01L51/0081Metal complexes comprising a IIIB-metal (B, Al, Ga, In or TI), e.g. Tris (8-hydroxyquinoline) gallium (Gaq3) comprising aluminium, e.g. Alq3
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    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0084Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H01L51/0088Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising osmium
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/009Polynuclear complexes, i.e. complexes having two or more metal centers
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    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/5012Electroluminescent [EL] layer

Abstract

Disclosed is an organic electroluminescent device material which is characterized by being composed of a metal complex having a substance represented by the general formula (1) below or a tautomer thereof as a partial structure. (1) [In the formula, Z11 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring; R11, R12 and R13 respectively represent a hydrogen atom or a substituent; and M11 represents a group 8-10 metal of the periodic table.]

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 an organic-elect opening luminescent device material, an organic-elect opening luminescent element, a display device and a lighting device.

BACKGROUND

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

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

[0004] In Patent No. 3,093,796, 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 .

[0005] Furthermore, 8-hydroxyquinoline aluminum complex as Hosutoi 匕合 was element having an organic light-emitting layer to which was doped with fluorescent bodies of trace (e.g., JP 63- 264692 discloses), 8-hydroxy quinoline aluminum complex as Hosutoi 匕合 was element having an organic light-emitting layer doped with a quinacridone type dye thereto (e.g., JP-3- 255190 JP), and the like.

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

[0007] where reporting of the organic EL element using the phosphorescence from the force Princeton University than excited triplet (MA Baldo et al., Nature, 395 Certificates, 151 _ 154 pages (1998)) force since its S, research on materials exhibiting phosphorescence at room temperature have come to be active.

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

[0009] With the excited triplet, the upper limit of the internal quantum efficiency is 100. / O. Therefore, theoretically becomes luminous efficiency force S4 times as compared with the case of the excited singlet, almost the same performance as a cold cathode tube are also considered for lighting applications because of the potential is obtained, et al .

[0010] For example, S. Lamansky et al., J. Am. Chem. Soc., 123 Certificates, in 4304 page (2 001 years) or the like, especially in the heavy metal complexes such as iridium complexes many compounds synthesis It has been studied.

[0011] Moreover, the aforementioned MA Baldo et al., Nature, 403 Certificates, No. 17, in the 750-753 pages (2000), as a dopant, consideration is using tris (2-phenylene Rubirijin) iridium ing.

[0012] Other, ME Tompson, etc., The 10th International Workshop on In organic and Organic Electroluminescence (EL '00, Hamamatsu) Te (Nobi Rere, L Ir (acac) as Dono down Bok, for example, (ppy) Ir ( the acac), also, Moon-Jae

Youn. 0g, Tetsuo Tsutsui, etc., still, The 10th International Works hop on Inorganic and Organic Electroluminescence (EL '00, Hamamatsu) to have you in, as a dopant, tris (2- (p- tolyl) pyridine) iridium (Ir ( Ptpy)), tris (called benzo [h] quinoline) iridium (Ir (bzq)) in which (Note these metal complexes examined with such generally ortho-metalated iridium complex.).

[0013] In addition, the, S. Lamansky et al., J. Am. Chem. Soc., 123 Certificates, 4304 also in the page (2001), etc., have been an attempt to devices by using a variety of iridium complexes that.

[0014] In order to obtain a high luminous efficiency, The 10th International Workshop on Inorganic and Organic Electroluminescence (EL '00, Hamamatsu) in, Ikai, etc. uses a hole-transporting compound as a host of a phosphorescent compound. Further, ME T ompson etc., various electron transporting material as a host of a phosphorescent compound, Ru les, doped with a new iridium complex thereto.

[0015] Onoretometarui 匕錯 body a central metal was platinum in place of iridium has attracted attention. Regarding this type of complex, examples which gave characterized ligands are known a number (e.g., Patent Documents: 1-5 and Non-Patent Reference 1.).

[0016] luminance and luminous efficiency when any case where a light emitting element, since the light that light emission derived from phosphorescent, are intended to be significantly improved compared with the conventional device, but the device the light emission life there is a problem that is lower than the conventional element point. Thus, the light emitting material of phosphorescent high efficiency is a performance improvement of the light emission life of the short-waved and elements of the emission wavelength can withstand the difficult practical use can be sufficiently achieved, a record, the is at present .

[0017] As for the shorter and shorter wavelengths, to date fluorine atom phenylalanine pyridine, Torifuruo Romechiru group, be introduced as a substituent an electron withdrawing group such as Shiano group, pico phosphoric acid or Birazaboru system as a ligand it is known to introduce a ligand (e.g., Patent Document 6: 13 and non-Patent Document:. ~ 4 see) is, these ligands with shorter and shorter emission wavelength of the luminescent material achieve blue, while the elements of high efficiency can be achieved, the emission lifetime of the device tends also seen to degradation, improvement in the trade-off has been required.

Patent Document 1: JP 2002- 332291 JP

Patent Document 2: JP 2002- 332292 JP

Patent Document 3: JP 2002- 338588 JP

Patent Document 4: JP 2002- 226495 JP

Patent Document 5: JP 2002- 234894 JP

Patent Document 6: WO 02/15645 pamphlet

Patent Document 7: JP 2003- 123982 JP Patent Document 8: JP 2002- 117978 JP

Patent Document 9: JP 2003- 146996 JP

Patent Document 10:

Patent Document 11: International Publication No. 05/007767 pamphlet

Patent Document 12: International Publication No. 04/101707 pamphlet

Patent Document 13: JP 2005- 053912 JP

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

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

[0018] An object of the present invention, the emission wavelength is controlled, showed high luminous efficiency and a long organic EL device emission lifetime is to provide an illuminating device and a display device.

[0019] To achieve the above object, the one aspect of the present invention is represented by the following general formula (1) or a metal complex having a tautomer of the general formula (1) as a partial structure in organic elect port eLEMENT material characterized. The general formula (1)

[0020] wherein, Z11 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. R, R, R each represents a hydrogen atom or a substituent. M is the Periodic Table of the Elements

11 12 13 11

It represents a group 8-10 metal in. ]

BRIEF DESCRIPTION OF THE DRAWINGS

[0021] FIG. 1 is a schematic diagram showing an example of a display containing an organic EL 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.

5 is a schematic view of a sealing structure of the organic EL element OLED1- 1.

6 is a schematic view of a formed by including an organic EL element lighting device.

BEST MODE FOR CARRYING OUT THE INVENTION

[0022] The above-mentioned object of the present invention, the configuration of the following:! Was achieved by to 28.

(1) the following general formula (1) or, metallic complexes with tautomers general formula (1) as a partial structure represented by the following general formula (2) or, tautomers formula (2) metal complexes that have a as a partial structure represented by the following general formula (3) or a metal complex having a tautomer of the general formula (3) as a partial structure represented by the following general formula (4) or, said formula (4 a metal complex having tautomers and as a partial structure) of the following general formula (5) or, said formula (5) a metal complex having tautomers as part structure or, the following general formula ( 6) or, organic elect port Ruminesse Nsu element material which is a metal complex having the general formula tautomers of (6) as a partial structure.

[0023] [Formula 1] general formula (1)

[0024] wherein, Z11 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. R, R, R each represents a hydrogen atom or a substituent. M is the Periodic Table of the Elements

11 12 13 11

It represents a group 8-10 metal in. ]

[0025] [Chemical formula 2] Formula (2)

[0026] wherein, Z21 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. R, R, R each represents a hydrogen atom or a substituent. M is the Periodic Table of the Elements

21 22 23 21

It represents a group 8-10 metal in. ]

[0027] [Formula 3] Formula (3)

[0028] wherein, Z31 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X, chi, chi is each may have a substituent group carbon atom or a nitrogen atom

31 32 33

Represents, but at least two are nitrogen atoms, or N (R) (where, R represents Hydrogen atom

3 3

It represents a substituent. ) Represents the. C represents a carbon atom. M is a Group 8 in the periodic table

31 31

Representing the 10 metals. The bond between C and N, the bond between the N and X, between X and X

31 33 32 33 bond, the bond between X and X, bond each single bond or a double bond between C and X

31 32 31 31

A representative. ]

[0029] [Formula 4] General formula (4)

Λ ^ -ι- X 4 2

Ιί 'λ

C 43,, ^ C 41: ' statement

'Z41, Roh'

[0030] wherein, Z41 represents an atomic group necessary for forming an aromatic heterocyclic ring. X, X is a substituted

It represents a good carbon atom or a nitrogen atom which may have a 41 42 group, at least one of which ChissoHara child or - N (R) - (wherein, R represents a hydrogen atom or a substituent.) a representative. M is

4 4 41

Represents a group 8-10 metal in the periodic table. C, C, C is each carbon atom

41 42 43

Represent. M represents a group 8-10 metal in the periodic table. The bond between C and C

41 41 42

, The bond between C and X bond between X and X, the bond between X and C, between C and C

Coupling between the 41 42 41 42 41 43 42 43 represents a single bond or a double bond. ]

[0031] [Chemical Formula 5 Formula (5)

[0032] wherein, Z51 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X represents an oxygen atom or a sulfur atom. R, R is a hydrogen atom or location

It represents a 51 51 52 substituent. M represents a group 8-10 metal in the periodic table. ]

51

[0033] [Chemical Formula 6] Formula (6)

Chi 62 Ichizu 63 wherein, Z61 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X chi chi may each may have a substituent group carbon atom or a nitrogen atom

61 62 63

It represents but represents at least one nitrogen atom. Μ is a group 8-10 of the periodic table

61

Representing the metal. ]

(2) the general formula (1) or, organic elect port luminescent element material according to the which is a metallic complex having a tautomer of the general formula (1) as a partial structure (1) fee.

(3) the general formula (1) or, that Z11 in metallic complex having a tautomer of the general formula (1) as a partial structure represents an atomic group necessary for forming an aromatic heterocyclic ring organic elect port luminescent device material according to (2) to feature.

(4) the general formula (2) or, organic elect port luminescent element member according to (1), wherein the tautomers of a metallic complex having as a partial structure of the general formula (2) fee.

(5) the general formula (3) or, said formula (3) Organic elect port luminescent element member according to (1), which is a metallic complex having tautomers as partial structure of fee.

(6) the general formula (3) or, in the metallic complex having a tautomer of the general formula (3) as a partial structure, X represents a carbon atoms which may have a substituent, X chi is nitrogen atom

31 32 33

Or N (R) (where, R represents. A hydrogen atom or a substituent) and being representative of the

3 3

Organic elect port luminescent device material according to (5) to be.

(7) In the above-described general formula (4) or, said formula (4) organic-elect opening luminescent element member according to (1), which is a metallic complex having tautomers as partial structure of fee.

(8) the general formula (5) or, organic elect port luminescent element material according to the which is a metallic complex having a tautomer of the general formula (5) as a partial structure (1) fee.

(9) Organic according to the general formula (5) or, X in metallic complex having a tautomer of the general formula (5) as a partial structure, wherein, characterized in that a sulfur atom (8) Jer

51

Data Toro luminescent element material.

(10) the general formula (6) or, organic elect port luminescent device material according to (1), characterized in that the tautomers general formula (6) is a metal complex having as a partial structure.

(11) the general formula (6) or, in the metal complex having a tautomer of the general formula (6) as a partial structure, X, at least one of the χ before, characterized in that represents a nitrogen atom

61 63

Organic elect port luminescent device material according to the serial (10).

(12) In the general formula (1), to being a M force S, iridium or platinum

11

Organic elect port luminescent device material according to (2) that.

(13) Organic-elect opening luminescent device material according to (12) which Z11 in the general formula (1) is characterized in that it represents an atomic group necessary to form an aromatic heterocyclic ring.

(14) In the general formula (2), to being a M force S, iridium or platinum

twenty one

Organic elect port luminescent device material according to (4) that.

(15) In the general formula (3), to being a M force S, iridium or platinum

31

Organic elect port luminescent device material according to (5) that.

In (16) above general formula (3), X represents a carbon atoms which may have a substituent, X,

31 32

X is a nitrogen atom or - N (R) - (wherein, R represents a hydrogen atom or a substituent.) Table a

33 3 3

Organic elect port luminescent device material according to (15), characterized in Succoth.

(17) In the general formula (4), to being a M force iridium or platinum

41

Organic elect port luminescent device material according to (7) that.

(18) In the general formula (5), to being a M force iridium or platinum

51

Organic elect port luminescent device material according to (8) that. (19) X force in the general formula (5) S, wherein, characterized in that a sulfur atom (18)

51

Organic elect port luminescent device material according to.

(20) In the general formula (6), to being a M force S, iridium or platinum

61

Organic elect port luminescent device material according to (10) that.

In (21) the general formula (6), X, to represent at least one nitrogen atom of X

61 63

Organic elect port luminescent device material according to (20), characterized.

(22) wherein (1) to organic elect port luminescent element characterized by containing the organic-elect opening luminescent element materials according to any one of (21).

(23) a light-emitting layer as a constituting layer, the the light emitting layer, characterized in that it contains an organic-elect opening luminescent device material of the mounting serial any to one of the above (1) to (21) (22 organic elect port device as described in).

(24) has a hole blocking layer as a constituent layer, wherein the hole-blocking layer containing an organic-elect opening luminescent device material according to any force one of said (1) to (21) organic elect port device as described before Symbol (22) or (23).

(25) a light-emitting layer as a constituent layer, light emitting layer, a ring structure in which at least one carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives or the Karubori down derivative is substituted by a nitrogen atom organic elect port device as claimed in any force one of said (22) to (24), characterized in that it contains a derivative having.

(26) has a hole blocking layer as a constituent layer, the hole blocking layer is at least one carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives or the carboline derivative is substituted by a nitrogen atom organic elect port device as claimed in any force 4, wherein said you characterized by containing derivatives having a ring structure (22) to (25).

(27) wherein (22) any force to (26), a display device characterized by having an organic-elect opening device as described in (1).

(28) wherein (22) any force to (26), the lighting apparatus characterized by having an organic-elect opening device as described in (1).

In the organic EL device material of the present invention, the configuration as defined any one of the above items (1) to (21), and succeeded in the molecular design of useful organic EL element material for the organic EL device . Further, by using the organic EL device material exhibits a high luminous efficiency and a long organic EL device emission lifetime, it is possible to provide a lighting device and a display device.

[0036] The present inventors have, as a result of extensive studies on the above problems, commonly are used phenylene Rubirijin (6-membered ring and 6-membered ring carbon as ligand of the metal complex - carbon linked by bonds which, shall) of the mother nucleus, the general formula (1) to (each "aromatic hydrocarbon ring, as represented by 6), or an aromatic heterocyclic ring (preferably a 6-membered ring) "and" aromatic heterocyclic ring (preferably a 5-membered ring) ", but carbon one-carbon bond, or, as linked by a carbon one nitrogen bond, an organic EL device material of the metal complex having a specific partial structure the organic EL device comprising a, a problem point of the organic EL element manufactured using metal complexes for blue traditional, the organic EL device material which has been controlled emission wavelength shorter side only in particular by an electron withdrawing group light-emitting life has been found to be greatly improved.

[0037] Further, by the emission wavelength of the substituents themselves be introduced as a substituent a long wave ones, the molecular design for imparting a function of controlling the emission wavelength of the metallic complex long wave region, the onset Ming in accordance of the general formula (1) to (6) or, selecting the appropriate partial structure by a basic skeleton of each of tautomers general formula (1) to (6) to a starting point it is possible.

[0038] Hereinafter, details of each component according to the present invention will be sequentially described.

[0039] "metal complexes"

It described metal complexes according to the organic EL device material of the present invention.

[0040] According to the present invention, the content layer of the metal complex having each tautomeric as a partial structure of the general formula (1) to (6) or the general formula (1) to (6), the light-emitting layer and / or a hole blocking layer was sigma preferred, when contained in the luminescent layer, use record as a light emitting dopant in the emissive layer, by Rukoto, external extraction efficiency up quantum efficiency of the organic EL device of the present invention ( it can be achieved a long life of the high bright cathodic) or emission lifetime.

[0041] "Formula (1) or tautomers general formula (1)"

In tautomer of the general formula (1) or the general formula (1), the aromatic carbon hydrocarbon ring represented by Z11, benzene ring, biphenyl ring, a naphthalene ring, Azuren ring, anthracene down ring, Fuenantoren ring, pyrene ring, Tarisen ring, a naphthacene ring, bird whistle two alkylene ring, o- Te Rufue cycloalkenyl ring, m- Terufueniru ring, p- Terufueniru ring, Asenafuten ring, a coronene ring, a fluorene ring, fluoranthrene ring, a naphthacene ring , pentacene ring, a perylene ring, a pair Ntafen ring, picene ring, a pyrene ring, pyranthrene ring, Ru Anse La entree down ring, and the like.

[0042] Among these preferably used are benzene rings. Further, the aromatic hydrocarbon ring will be described later, R in the general formula (1), R, a substituent represented by R

11 12 13

Ayoi.

[0043] In tautomer of the general formula (1) or the general formula (1), the aromatic double ring represented by Z11, furan ring, Chiofen ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, Piraji down ring, a triazine ring, a benzimidazole ring, Okisajiazoru ring, Toriazoru ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, Baie Nzochiazoru ring, benzo O benzoxazole ring, a quinoxaline ring, quinazoline ring, phthalazine ring, the force carbazole ring, a carboline ring, ring and the like in which at least one carbon atom of a hydrocarbon ring constituting a carboline ring is further substituted at the nitrogen atom.

[0044] Among them preferred it is a pyridine ring. Further, the aromatic heterocyclic ring, described below, prior to following general formula (1) R, R, may have each represented substituents at R.

11 12 13

[0045] In the tautomer of formula (1) or the general formula (1), it is preferred ring represented by R11 is an aromatic heterocyclic ring. 5-membered heterocycles as are contained as a partial structure of the general formula (1) of the present invention, if it is contained in the molecule, (corresponding to Z11 in the present invention) aromatic ring connected thereto , it is an aromatic heterocyclic ring, and improve the stability of the molecule, the emission wavelength becomes shorter wavelength.

[0046] In the tautomer of formula (1) or the general formula (1) R, R, it is represented by each of R

11 12 13

Examples of the substituent that, for example, an alkyl group (e.g., methyl group, Echiru group, isopropylidene Honoré group, hydroxy E butyl group, Metokishimechinore group, triflate Ruo Russia methyl, t_ butyl), a cycloalkyl group (e.g. , cyclopentyl group, cyclohexyl group, etc.), if Ararukiru group (eg, Benjinore group, 2-phenethyl group, etc.), an aromatic hydrocarbon group (e.g., phenyl group, p- Kurorofuweniru group, mesityl group, a tolyl group, a xylyl group, Bifuwe two drill group, a naphthyl group, an anthryl group, Fuenantoriru group), an aromatic Hajime Tamaki (e.g., furyl group, thienyl group, Pirijinore group, pyridazinyl group, pyrimidinyl group, Pirajuru group, triazinyl group, Imida Zoriru group , a pyrazolyl group, a thiazolyl group, a quinazolinyl group, carbazolyl group, carbolinyl group, Jiaza (The di- § The carbazolyl group, those one at any of the carbon atoms constituting the Karubori down ring of the carbolinyl group is substituted by a nitrogen atom.) Rubazoriru group, full Tarajiniru group), an alkoxyl group (e.g., ethoxy group, isopropoxy group, butoxy group), Ariruokishi group (e.g., phenoxy group, Nafuchiruokishi group), Shiano group, water 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. These groups may be further substitution.

[0047] Among them, in the present invention, the R, R, of the groups represented by R is at least one, of the

11 12 13

It is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group.

[0048] In the tautomer of formula (1) or the general formula (1), M, contact the Periodic Table of the Elements

11

(Also a metal atom, which may be a ion) takes 8 to Group 10 metal force among them preferably use Les representing the, what is is platinum (Pt) and iridium (Ir). Further, in the metal complex having the general formula (1) or the general formula 互辺 isomer of (1) as a partial structure, M is Yogu I be a metal

11

Good record, even on.

[0049] In the present invention, in which is represented in tautomeric forms and the M in the general formula (1) or the general formula (1)

11

Heart metal (also referred to as a complex-forming) coordinate bond is formed between the (which may be a well-ion of a metal) has been metallic complex is formed.

[0050] "formula (2) or a tautomer of said formula (2)"

In tautomer of the general formula (2) or the general formula (2), aromatic coal hydrocarbon ring represented by Z21, in the tautomer of formula (1) or the general formula (1) is synonymous with an aromatic hydrocarbon ring you express by Z11.

[0051] In the tautomer of formula (2) or the general formula (2), an aromatic double ring represented by Z21, the tautomeric formula (1) or the general formula (1) in the body, it is synonymous with Kaoru aromatic heterocyclic ring represented by Z11.

[0052] In the tautomer of formula (2) or the general formula (2), R, R, each R, represented respectively

21 22 23

Substituents is, R in tautomer of the general formula (1) or the general formula (1), R, R

11 12 13 is synonymous with the substituent represented by each by. [0053] In tautomer of the general formula (2) or the general formula (2), represented by M, the periodic

twenty one

8 to Group 10 metal in the table (or the ion), in a tautomer of the general formula (1) or the general formula (1) is represented by M, group 8-10 of the periodic table and metal

11

It is synonymous.

[0054] "Formula (3) or the general formula (3) tautomers"

In tautomer of the general formula (3) or the general formula (3), aromatic coal hydrocarbon ring represented by Z31, in the tautomer of formula (1) or the general formula (1) is synonymous with an aromatic hydrocarbon ring you express by Z11.

[0055] In the tautomer of formula (3) or the general formula (3), an aromatic double ring represented by Z31, the tautomeric formula (1) or the general formula (1) in the body, it is synonymous with Kaoru aromatic heterocyclic ring represented by Z11.

[0056] In the general formula (3) or tautomers general formula (3), represented each X, X, in X

31 32 33

Substituents represented by R in Reru N (R), the tautomeric formula (1) or the general formula (1)

3 3

In sexual body R, R, is synonymous with the substituent represented by each of R.

11 12 13

[0057] In the tautomer of formula (3) or the general formula (3), represented by M, the periodic

31

8 to Group 10 metal in the table (or the ion), in a tautomer of the general formula (1) or the general formula (1) is represented by M, group 8-10 of the periodic table and metal

11

It is synonymous.

[0058] In the tautomer of formula (3) or the general formula (3), X is also substituted

31

A have carbon atoms, X, X is a nitrogen atom or N (R) (where, R represents or a hydrogen atom

32 33 3 3

The other represents a substituent. ) It is preferred that. Thus, the emission wavelength becomes shorter wavelength

, Also improves the ease of synthesis.

[0059] "Formula (4) or the general formula (4) tautomers"

In tautomer of the general formula (4) or the general formula (4), an aromatic double ring represented by Z41, in the tautomer of formula (1) or the general formula (1), it is synonymous with Kaoru aromatic heterocyclic ring represented by Z11.

[0060] In the tautomer of formula (4) or the general formula (4), X, represented by each of X -

41 42

Substituents represented by N (R) _ of R is formula (1) or Oite R to tautomers general formula (1), R, in same as the substituents each represented by a R is there.

11 12 13

[0061] In the tautomer of formula (4) or the general formula (4), represented by M, the periodic

41

8 to Group 10 metal in the table (or the ion), in a tautomer of the general formula (1) or the general formula (1) is represented by M, group 8-10 of the periodic table and metal

11

It is synonymous.

[0062] "Formula (5) or the general formula (5) tautomers"

In tautomer of the general formula (5) or the general formula (5), aromatic coal hydrocarbon ring represented by Z51, in the tautomer of formula (1) or the general formula (1) is synonymous with an aromatic hydrocarbon ring you express by Z11.

[0063] In the tautomer of formula (5) or the general formula (5), an aromatic double ring represented by Z51, the tautomeric formula (1) or the general formula (1) in the body, it is synonymous with Kaoru aromatic heterocyclic ring represented by Z11.

[0064] location general formula (5) or the general formula tautomer of (5), that R, represented by each of R

51 52

Substituent are each at tautomer of the general formula (1) or the general formula (1) R, R, with R

11 12 13 is synonymous with the substituent represented.

[0065] In the tautomer of formula (5) or the general formula (5), represented by M, the periodic

51

8 to Group 10 metal in the table (or the ion), in a tautomer of the general formula (1) or the general formula (1) is represented by M, group 8-10 of the periodic table and metal

11

It is synonymous.

[0066] In the tautomer of formula (5) or the general formula (5), it X is sulfur atom

51

It is preferred. Generally, Okisazoru derivatives, unstable der Rukoto susceptible to intramolecular ring-opening are known. In the general formula of the present invention (5), of which there it is greatly improved, it is thiazole derivative molecules are more stable.

[0067] "Formula (6) or a tautomer of the general formula (6)"

In tautomer of the general formula (6) or the general formula (6), aromatic coal hydrocarbon ring represented by Z61, in the tautomer of formula (1) or the general formula (1) is synonymous with an aromatic hydrocarbon ring you express by Z11.

[0068] In the tautomer of formula (6) or the general formula (6), an aromatic double ring represented by Z61, the tautomeric formula (1) or the general formula (1) in the body, it is synonymous with Kaoru aromatic heterocyclic ring represented by Z11.

[0069] In the tautomer of formula (6) or the general formula (6), represented by M, the periodic

61

8 to Group 10 metal in the table (or the ion), in a tautomer of the general formula (1) or the general formula (1) is represented by M, group 8-10 of the periodic table and metal

11

It is synonymous.

[0070] In the tautomer of formula (6) or the general formula (6), X, at least one of X

61 63

It is preferable that the nitrogen atom. Thus, the emission wavelength becomes shorter wavelength, also improves the ease of synthesis.

[0071] Hereinafter, according to the present invention, a specific example of a metal complex having a respective tautomeric material elements of the general formula (1) to (6) or the general formula (1) to (6) as a partial structure but the invention is not restricted to these.

[0072] [Formula 7]

[0073] [of 8]

[Emperor 7ΐ dimensions

u0076o

[0077] [Chem. 11] Zl ^ [8Z00]

[0079] [of 13]

[0080] [of 14]

a0081 l

soo

[0083] [Formula 17]

[8ΐ ^>] [800]

Metal complexes according to the organic EL device material of the present invention, for example 〇 Rganic Le Journal, vol3, No. 16, p2579~2581 ( 2001), Inorganic Chemistry, Chapter 30 Certificates, No. 8 16 85: 1687 pages (1991 year)]. Am. Chem. Soc., 123 Certificates, 4304 pages (2001), Inorganic Chemistry, Chapter 40 Certificates, No. 7, 1704-1711 page (2001), I norganic Chemistry, 41 Certificates, No. 12, 3055-3066 page (2002), New Journal of Chemistry., 26 Certificates, 1171 pages (2002), further, by applying a method such references cited in these statements 献中It can be synthesized.

[0086] "applied to the organic EL element of the organic EL device material comprising a metal complex"

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), the light emitting layer or a hole blocking layer is preferably used for the LES, . Further, the light emitting layer, is preferably used as a light emitting dopant.

[0087] (light-emitting host and the light-emitting dopant)

The mixing ratio of the light-emitting dopant to the emission host a phosphothioate Η 匕合 product is the main component of the light-emitting layer is preferably Ru der to adjust the range of 0.1 less than 1% by mass to 30% by mass.

[0088] However, the light emitting dopant opponent having different structures of mixing good tool be used by mixing plural kinds of compounds, also a phosphorescent dopant and a fluorescent dopant having other metal complexes or other structures good.

[0089] Herein, an may be used in combination with the metal complex to be used as the light emitting dopant dopant (phosphorescent dopant, a fluorescent dopant, etc.).

[0090] emitting dopant is roughly, there are two types of phosphorescent dopants that emit fluorescent dopant and phosphorescent which emits fluorescence.

[0091] A typical example of the former (fluorescent dopant), coumarin dyes, pyran based dyes, Shiani emissions based dyes, Kurokoniumu dyes, Sukuariumu dyes, O Kiso Benz anthracene dyes, Furuoresein dyes, rhodamine dyes , pyrylium dyes, perylene dyes, styryl Reuben dyes, Porichiofen dyes, or rare earth complex based fluorescent material, and the like.

[0092] 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 a Sumiumu compound is among the most preferred are iridium compound.

[0093] Specifically, a compound described in the following patent publications. [0094] WO 00/70655 pamphlet, 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 Patent brochures, Japanese Patent 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.

[0095] A part of the specific examples below.

[0096] [Formula 19]

[0097] [of 20]

[0098] [of 21]

(Light-emitting host)

The emission host (also referred to simply as a host), most multi-les mixing ratio in the light emitting layer composed of two or more compounds (mass), it means that the I 匕合 was in the other compound Rre, Te is referred to as "de one Pantoi 匕合 product (simply, also referred to as a dopant)". For example, the light-emitting layer 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 phosphate H 匕合 product . Further, the light-emitting layer Compound A, Compound B, is composed of three compounds C, the mixture ratio of eight: 8: 〇 = 5: 10: 85 Deare words, Compound A, Compound B dopant Lee 匕合are those, compound C is Hosutoi 匕合 thereof.

[0100] The luminescent host used in the present invention is not particularly limited in structure, typically force carbazole derivatives, triaryl § amine derivatives, aromatic borane derivatives, nitrogen-containing heterocyclic compounds, Chiofen derivatives, furan derivatives, those having a basic bone skeleton of such Origoariren compound, or in carboline derivatives and Jiaza force carbazole derivatives (wherein the di § the carbazole derivative, hydrocarbon ring constituting a carboline ring of carboline derivatives at least one record carbon atoms is replaced by nitrogen atoms, it represents a shall.), and the like.

[0101] Among them carboline derivatives, Jiaza force carbazole derivatives are preferably used.

[0102] Hereinafter, carboline derivatives, specific examples force present invention such Jiaza force carbazole derivative is not limited thereto. These compounds it may also be used as a hole blocking material les.

[0103]

[0104] [of 22]

The light emitting host used in 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 the high molecular compound having a repeating unit (an evaporation polymerizing emission host) Les, Les,. [0106] The light-emitting host, a hole transporting ability and an electron transporting ability, and prevents the longer wavelength of emission, Shi having a high Tg (glass transition temperature) is favored.

[0107] Specific examples of the light emitting host, compounds described in the following references are preferred.

For example, JP 2001- 257076, JP-the 2002- 308855, JP-same 2001- 313 179 discloses, the 2002- 319491, JP-the 2001- 357977, JP-the 2002- 3 34786, JP-same 2002- 8860 JP, the 2002- 334787, JP-the 2002- 1 5871 JP, the 2002- 334788, JP-the 2002- 43056, JP-the 2002- 3 34789, JP same 2002- 75645, JP-same 2002 - 338 579, JP same 2002- 105445, JP-the 2002- 343568, JP-the 2002- 141173, JP-the 2002 - 352957 discloses, the 2002- 203683, JP-the 2002- 363227, JP-same 20

02- two hundred and thirty-one thousand four hundred and fifty-three JP, the 2003- 3165 JP, the 2002- 234888, JP-same 20

03- 27048, JP same 2002- 255934, JP-the 2002- 260861, JP-the 2 002- 280 183 discloses, the 2002- 299060, JP-the 2002- 302516, JP-the 2002- 305083, JP-same 2002- 305084, JP Publication Nos. 2002- 308837.

[0108] Next, there will be described a configuration of a typical organic EL device.

[0109] "layers constituting the organic EL device"

It described layers constituting the organic EL device of the present invention.

[0110] The present force Preferred specific examples of the layer structure of the organic EL elements in the following of the Invention The present invention is not limited to these. (I) anode / hole transport layer / luminescent layer / hole blocking layer / electron transport layer / cathode (ii) anode / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode (iii) anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode (iv) anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode ( V) anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer more / cathode (vi) anode / anode buffer more / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode (vii) anode / anode buffer more / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer even / cathode "blocking layer (electron blocking layer, hole blocking layer)"

Blocking layer according to the present invention (e.g., an electron blocking layer, hole blocking layer) will be described.

[0111] In the present invention, a hole blocking layer, the electron blocking layer or the like, a is the preferred tool particularly preferable to use an organic EL device material of the present invention is to use the hole blocking layer.

[0112] The hole blocking layer and the organic EL device material of the present invention, when to be contained in the electron blocking layer, claim 1: 17 is described in any force 4 of the hole a metal complex according to the present invention it may be contained in the blocking layer Ya electron blocking layer such as a layer constituent components as 100 mass% state, other organic compounds (e.g., Yore the layers constituting the organic EL device of the present invention, are compounds) etc. and it may be mixed.

[0113] The thickness of the blocking layer according to the present invention is preferably 3 nm to:! A OOnm, more preferably from 5 nm to 30 nm.

[0114] "hole blocking layer"

In a broad sense, the hole blocking layer has the function of the electron transporting layer, while have a function of transporting electrons made very small material capable of transporting holes, deter hole while transporting electrons recombination probability of electrons and holes by can be improved.

[0115] 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. If necessary the structure of an electron transport layer described later can be used as a hole blocking layer according to the present invention.

[0116] "electron blocking layer"

On the other hand, has the functions of hole transport layer in a broad sense, the electron blocking layer, the ability to transport electrons while having a function of transporting holes but a very small material 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.

[0117] In the present invention, the adjacent layer adjacent to the light-emitting layer, i.e., a hole blocking layer, the electron deter layer, above the preferred instrument, especially a hole using the organic EL device material of the present invention it is preferable to use the blocking layer. [0118] "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 this the force s provided as a single layer or plural layers.

[0119] As the hole transporting material, particularly limited Nag Conventionally, in Hikarishirubeden materials, hole injection layer or EL elements which are conventionally used as a hole charge injection transporting materials, used in the hole transporting layer any Churyoku known those can be selected and used.

[0120] The hole transporting material, a hole injection or transport, and also to have one of the electron barrier property, organic matter, it may also be any of inorganic les. For example Toriazoru derivatives, O key Sajiazoru derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, full We two range § amine derivatives, Ariruamin derivatives, amino-substituted chalcone derivatives, Okisazoru derivatives, styryl anthracene derivatives, Furuore non derivative , hydrazone derivatives, stilbene derivatives, silazane derivatives, Anirin based copolymer polymer, and an electroconductive oligomer, include especially Chio Fen oligomer.

[0121] As the hole transporting material, the force porphyrin compounds which can be used those described above, aromatic tertiary Amin compounds and Suchiriruamin compounds, it is particularly preferable to use an aromatic tertiary Amin of compounds.

[0122] Representative examples of aromatic tertiary Amin compounds and Suchiriruamin compound, N, N, N ', N, one tetraphenyl one 4, 4' - Jiaminofueniru; N, New '- Jifue sulfonyl one N, New , velvetleaf scan (3 Mechirufue sulfonyl) one [1, 1, one Bifue sulfonyl] one 4, 4, one Jiamin (TPD); 2, 2-bi scan (4-di one ρ- tolyl § Minofu enyl ) propane; 1,1-bis (4-di one ρ- Toriruaminofu Eniru) cyclohexane; New, New, New ', New, one tetra one ρ- tolyl one 4, 4' - Jiaminobifue alkenyl; 1, 1- bis (4-di one ρ- tolyl § Minofu enyl) hexane one 4- Fuenirushikuro; bi scan (4- Jimechiruamino one 2 - methylphenyl) phenylmethane, bis (4-di one ρ- Torinorea Minofueniru) phenylmethane; New, New, one diphenyl one N, N '- di (4-methoxyphenyl) -4, 4' - Jiaminobi Enyl; New, New, New ', New, one tetraphenyl - 4, 4' - Jiaminojifu phenyl ether; 4, 4, _ bis (Jifueniruamino) quad riff enyl; Ν, Ν, Ν- tri ([rho - tolyl) Amin; 4_ (di - .rho. Toriruamino) _4, - [4 - (di - .rho. Toriruamino) Suchirinore] stilbene; 4-N, N-Jifueniruamino one (2 Jifue two ruby ​​two Honoré) benzene; 3 main Tokishi 4 ' -N, N-diphenyl-amino stilbene; N- phenylene carbazole, is Raniwa, in U.S. Patent No. 5, 061, 569 Pat intramolecular two fused aromatic rings disclosed in a thing, for example 4, 4 '_ bis [^^ _ (1 _ naphthyl) _ ^ _ Fuweniruamino] Bifuweniru (NPD), triflumizole We sulfonyl § Min unit described in JP-a-4 308 688 3 One starburst to the consolidated 4, 4 ', 4' '_ tris [1 ^ _ (3 _ Mechirufe sulfonyl) -N- Fuweniruamino] triphenyl § Min (MTDATA) and the like.

[0123] In addition these materials are introduced in a polymer chain, or these materials can also be used polymeric materials whose main chain of the polymer.

[0124] Further, p-type one Si, inorganic compounds such as p-type one SiC hole injection material, can be force S used as a hole transporting material. The hole transporting material is preferably a high Tg.

[0125] The hole transport layer, the hole transport material, for example, vacuum deposition, spin coating, key Yasuto method, an inkjet method, by a known method LB method, formed by thinning this and the force can be S. Thickness particularly limited release for the hole transport layer, but is usually about 5nm~50 OOnm. The hole transport layer may be one or a layered structure composed of two or more kinds of the above materials.

[0126] "electron transport layer"

Made of a material having a function of transporting electrons from the electron transporting layer, an electron injection layer in a broad sense, a hole blocking layer are included in an electron transport layer. Electron-transporting layer may be force S kicking set a single layer or multiple layers.

[0127] Conventionally, an electron-transporting layer of a single layer, and if a plurality of layers as Yore electron transport layer in contact next to the cathode side of the light-emitting layer is an electron transporting material (which functions also as a hole blocking material) , known material under Symbol is.

[0128] Furthermore, use of the electron transport layer, have a function of transporting electrons injected from the cathode to the emission layer Yogu as the material is optionally selected Churyoku conventionally known compound Les, it is Rukoto.

[0129] Materials used in the electron-transporting layer (hereinafter, referred to as an electron transporting material) Examples of nits port substituted fluorene derivatives, Jifuwe two Rukinon derivatives, Chio pyran dioxide derivatives, heterocyclic tetracarboxylic such Na lid Ren perylene carboxylic acid anhydrides, force Norepojiimido, 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 Lumpur ring, also quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group, Rukoto force S used as the electron transporting material.

[0130] In addition these materials are introduced in a polymer chain, or these materials can also be used polymeric materials whose main chain of the polymer.

[0131] The metal complexes of 8 _ quinolinol derivatives, such as tris (8-quinolinol) Arumiyuu beam (Alq), tris (5, 7-dichloro-one 8-quinolinol) aluminum, tris (5, 7-jib port mode _ 8_ quinolinol) aluminum, tris (2-methyl-_8 _ quinolinol) aluminum, tris (5-methyl-_ 8 _ quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and the central metal of these metal complexes an in, Mg, Cu, Ca, Sn, metal complexes replaced-out location to the Ga or Pb may also be used as the electron transporting material. Other, Metanorefuri mono- or metal phthalocyanine, or others that their termini are substituted with etc. alkyl group Ya sulfonic acid group, 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.

[0132] The electron-transporting layer, the electron transport material, such as a vacuum deposition method, a spin coating method, key Yasuto method, an inkjet method, by a known method LB method, Rukoto force be formed by thinning It can be S. 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 comprised of one or more kinds of the above materials.

[0133] Next, used as a constituent layer of the organic EL device of the present invention, the injection layer is described

[0134] "injection layer": the electron injection layer, a hole injection layer

Injection layer is provided if necessary, there is an electron injection layer and the hole injection layer, between the anode and the light emitting layer or the hole transport layer as described above, and, presence between the cathode and the light-emitting layer or an electron transport layer it may be Zaisa.

[0135] An injection layer, the drive voltage is lowered and the light-emitting layer provided between an electrode and an organic layer to improve luminance that, "Organic EL element and its Industrialization Front (Nov. 30, 1998 E j 'Tea '2 Chapter 2 of E, Inc. published) "" are an electrode material "(described in detail in pages 123 to 166), a hole injection layer (anode buffer more) and an electron injection layer (more cathode buffer) there is a door.

[0136] anode buffer more (hole injection layer), JP-9- 45479 discloses, 9 one 260 062 JP has also been described in detail in the 8-288069 discloses such, as a specific example, more phthalocyanine buffer typified Dofu Taroshianin, more oxide buffer typified by vanadium oxide, amorphous carbon buffer further, Poria diphosphate (Emerarudi down) and a conductive polymer a polymer buffer one layer or the like using such Porichiofen include the

[0137] 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, strike more metal buffer typified by mouth Nchiumu Ya aluminum, alkali metal compound buffer more Ru are as lithium fluoride, alkaline earth metals compound buffer further represented by magnesium fluoride, an oxide represented by aluminum oxide one layer such as a buffer and the like.

[0138] The buffer further (injection layer) It is the thickness of the well by the force its desirability tool material is preferably in the range of 0. Lnm~100nm very thin.

[0139] This injection layer, the above materials, for example, vacuum deposition, spin coating, casting, ink jet method, by a known method LB method, can be formed by thin film I spoon. Especially for the film thickness of the injection layer is restricted away, but usually is about 5 to 5000 nm. Injection layer This may be a single layer structure comprised of one or more kinds of the above materials.

[0140] "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. Metals such as Au Specific examples of such an electrode material, Cul, indium tin O key Sid (ITO), SnO, include a conductive transparent material such ΖηΟ is. Further, IDIXO (In O -

2 2 3

Zn 〇) may be used spruce amorphous in can prepare a transparent conductive film material. Anode, by a method such as the electrode material to vapor deposition or sputtering, a thin film is formed, if not desired shape Yogu or pattern accuracy by forming a pattern of requires less photolithography one method (100 μ to or higher than m), the pattern may be formed through a mask vapor deposition or sputtering Nozomu Tokoro shape when the electrode material. The case 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 Omega / mouth. Further thickness force usually depends on the material 10 nm to: 1000 nm, it is preferably selected in the range of 10 nm to 200 nm.

[0141] "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 / copper mixture, a magnesium / silver mixture, a magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al O) mixture, indium, a lithium / aluminum mixture, dilute

twenty three

Earth metal, and the like. Among these, from the viewpoint of electron injection property and durability against oxidation or the like, a mixture of the second metals value of the electron injection metal and a work function than this is the large stable metal, such as magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al O) mixture

twenty three

, Lithium / aluminum mixture, and aluminum. Cathode, by vapor deposition, sputtering or some other method of these electrodes material, by forming a thin film, it Rukoto force s to produce. The sheet resistance several hundred Omega Zeta port less preferably fixture thickness usually 10nm~1000nm as a cathode, is preferably selected in the range of 50 nm to 200 nm. Herein, to transmit emission, either one force S of the anode or the cathode of the organic EL element, emission luminance is advantageous improved if transparent or translucent.

[0142] "substrate (substrate, the substrate, also referred to as a support, or the like)"

As the substrate according to the organic EL device of the present invention, glass, of the type of plastic it was particularly limited Coati is not particularly limited as long as the transparent, is the preferred substrate used for example, glass, quartz , mention may be made of a light transmissive resin film. In particular it preferred substrate is a resin film capable of providing flexibility to the organic EL element.

[0143] As the resin film, such as polyethylene terephthalate (PET), polyethylene naphthenate tallates (PEN), polyether sulfone (PES), polyetherimide, Porieterue Teruketon, Porifue two Rensurufuido, polyarylate, polyimide, polycarbonate (PC), cellulose tri-acetate (TAC), a film and the like made of cellulose acetate propionate (CAP) and the like.

[0144] the surface of the resin film, an inorganic material or coating or High Priestess Tsu Yogu water vapor permeability even de coating is formed 0. 01g / m 2 'day' atm following high barrier for both the organic Rere Shi preferred to be a film.

[0145] external extraction efficiency of light emission at room temperature of the organic-elect opening device of the present invention is preferably from preferably not less than 1% instrument is 2% or more. Here, the quantum efficiency (%) Shi out outside up = number of electrons X 100 that was run on the number of photons / organic EL device emitting organic EL device the outside.

[0146] Furthermore, it is possible to use a hue improving filter Chief of the color filter first class.

[0147] When used in lighting applications, it can be used in combination roughened films in order to reduce the emission unevenness (antiglare Huy Roh REM, etc.).

[0148] consists of an organic EL element 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.

[0149] "method for manufacturing the organic EL device"

As an example of a manufacturing method of an organic EL device of the present invention, the anode Z hole injection layer Z hole transport layer

/ Light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / preparation method of the organic EL element composed of the cathode will be described.

[0150] First, a suitable substrate, a desired electrode material, for example, a thin film made of an anode substance, 1 mu m or less, preferably to a film thickness of 10 nm to 200 nm, by way of vapor deposition or sputtering It is formed, 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.

[0151] As a method for thinning the 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. If you use the film adopts the deposition, the deposition conditions vary due to kinds of materials used, generally baud preparative heating temperature 50 ° C~450 ° C, vacuum degree of 10- 6 Pa~10- 2 Pa, deposition rate 0. 01nm~50nm / sec, a substrate temperature of - 50 ° C~300 ° C, it is desirable to choose an appropriate thickness in the range of 0. lnm~5 zm.

[0152] After formation of these layers, a thin film made of a cathode material is formed thereon, as preferably less 1 mu m make a layer thickness in the range of 5 0Nm~200nm, for example more vapor deposition, sputtering or some other method It is formed, by providing the cathode, desired organic EL device can be obtained. Preparation of the organic EL element, but may be subjected to film formation method different extraction halfway preferably made consistent only one vacuuming from the hole injecting layer to the cathode. At that time, the required to be carried out under a dry inert gas atmosphere.

[0153] "display device"

Described display device of the present invention.

The display device of [0154] the present invention may be a multi-colored in a single color, it will be described here multicolor display device. For multi-color display device, a shadow mask only at the time of forming the light emitting layer is provided, a vapor deposition method, a casting method, a spin coating method, an inkjet method, a film by a printing method or the like can be formed

[0155] When patterning is performed only the light-emitting layer, limited to the method is not preferably evaporation

, An inkjet method, a printing method. Les, Shi use les were putter Jung like a shadow mask in case of using an evaporation method.

[0156] 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.

[0157] Such multi-color display device obtained by, in the case of applying the direct-current voltage, the anode +

The cathode - the application of a voltage of about 2~40V as polarity, light emission occurs. Also, no at all emission without current flows even if a voltage is applied in reverse polarity. Furthermore, in the case of applying an AC voltage, the anode is +, emits light only when the cathode becomes one state. Name your, the waveform of the alternating current to be applied may be arbitrary.

[0158] multi-color display device, a display device, a display, as possible out be used as various light emission sources. The display device or the display, blue, red, by using three kinds of organic EL elements of green light emission, it is possible to display full color.

[0159] Display devices, as the display televisions, personal computers, 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.

[0160] 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.

[0161] "lighting device"

It illustrates lighting device of the present invention.

[0162] a light source of the optical storage medium as the intended use of the organic EL element having a resonator structure such as Yoguko be an organic EL element having a resonator structure into the organic EL element of the present invention, an electronic photocopier light source, an optical communication processor sources, power sources for a photo-sensor, and the like, such limitation les. Further, by the laser oscillation, it may be used for the above applications.

[0163 In addition, the organic EL device of the present invention may be used as a type of lamps, such as illumination lamp or a light source for exposure, the type of and project Chillon apparatus for projecting an image, still images and moving images According, it is used as a display device of a type in which direct visualization (display). According, either in an active matrix method in a simple matrix (passive matrix) method driving method when used as a display device for video playback. Alternatively, the 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. [0164] Hereinafter, will be explained based on an example of a display device having an organic EL device of the present invention with reference to the accompanying drawings

[0165] FIG. 1 is a schematic diagram showing an example of a display containing an organic EL 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.

[0166] Display 1, and a display unit A, the control unit B for performing an image Hashi查 of display section A based on image information having a plurality of pixels.

[0167] The control unit B is connected to the display unit A electrically, transmits a scanning signal and an image data signal on the basis of the images information from outside the plurality of pixels, image elements of each scanning line by the scanning signal There displays the image information on the display unit a performs image scanning which emits light according to image data signals.

[0168] FIG. 2 is a schematic drawing of a display section A.

[0169] 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.

[0170] In figure, light from pixels 3 is shows a case to be taken in the direction of an arrow.

[0171] wiring of the scanning lines 5 and plural data lines 6 each made of a conductive material, the lines 5 and the lines 6 perpendicular to the grid pattern, and connected with the pixels 3 at the crossed points ( details are not shown the figure).

[0172] pixels 3, when the scanning signal is applied from the scanning lines 5, receive the data signal from the data lines 6, and emit light corresponding to received image data. Pixel color emitting red region, pixels in the green region, the pixels of the blue region, as appropriate, side by side on the same substrate, it is possible full color one appears.

[0173] Next, an emission process of pixels will be explained.

[0174] FIG. 3 is a schematic diagram of a pixel.

[0175] pixels, the organic EL element 10, a switching transistor 11, driving transistor 12, and a capacitor 13, and the like. As the organic EL element 10 to a plurality of pixels, red, green, full color display can line Ukoto by juxtaposing organic EL element of blue light - emitting a use record ,, these on the same substrate.

[0176] In FIG. 3, the image data signal is applied through the data lines 6 from the control section B to drain of the switching transistor 11. When 查信 No. run to the gate of Suitchin grayed transistor 11 through the scanning lines 5 are applied from the control unit B, the switching transistor 11 is switched on, the image data signal applied to the drain and the capacitor 13 drive It is transmitted to the gate of transistors 12.

[0177] 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.

[0178] 查信 No. run by sequential Hashi查 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.

[0179] That is, light emission of the organic EL element 10, and against the organic EL element 10 of each of the plurality of pixels, provided with a switching transistor 11 and driving transistor 12 which is an active element, a plurality of pixels 3 each organic EL doing light emitting element 10. Les call such a light-emitting method and an active matrix system, Ru.

[0180] Here, light emission of the organic EL element 10 may be emission with plural gradations according to image signal data having plural gradation potentials, given by binary image data signal emission amount of on, it may be off.

[0181] The holding of the electric potential of the capacitor 13, Moyore be continuously maintained until the next application of run No. 查信, and, Yo Le be discharged immediately before the next run No. 查信 is applied ,.

[0182] In the present invention is not limited to the active matrix method as described above, it may be light emission driving a passive matrix type light emission of organic EL element run No. 查信 is according to data signal only when Hashi查.

[0183] FIG. 4 is a schematic drawing of a display employing a passive matrix method. Figure 4 me Te, a plurality of image data lines 6 and the scanning line 5 of multiple is provided opposite to a grid pattern across the pixel 3.

[0184] sequentially when run No. 查信 scanning line 5 is applied by Hashi查, pixel 3 connecting to the applied scanning line 5 emits according to the image data signals. Reducing the picture element 3 is an active element of the no-tool manufacturing cost passive matrix method can be achieved.

[0185] Organic EL materials according to the present invention, also, as a lighting device, can be applied to an organic EL device which emits light of substantially white. 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 three primary colors of blue, blue and yellow, the complementary color relationship such as blue-green and orange 2 one of the emission maximum wavelength may be one containing.

[0186] 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 , Mononore combining the dye material that emits light in the light emitting material strength as the excitation light, according in displacement, but, in the white organic elect port Rumine' sensing element according to the present invention, a plurality combining scheme emissive dopant preferable.

[0187] The layer structure of the organic-elect opening device as to obtain a plurality of emission colors, the multiple light-emitting dopant, a method for more present in one light-emitting layer, have a plurality of light emitting layers, the light emitting method for each occurrence emission wavelength different dopants in the layer, and the like method of forming a micro-pixel emitting a different wavelength in a matrix.

[0188] In the white organic elect port luminescent element according to the present invention may be subjected to putter Jung a metal mask or an ink-jet printing method during film formation needed

. , Le, Re be putter Jung Les, Le, and, the elements all layers be to good, the electrode and the light emitting layer and putter Jung case, only the electrode pattern Jung to putter Jung.

[0189] If the backlight in the Nag example, a liquid crystal display device particularly limited as the light emitting material used for a light-emitting layer, by fit to the wavelength range corresponding to the CF (color filter) characteristics urchin, platinum complexes according to the present invention, or it may be whitened combination optionally selected from the known light emitting material.

[0190] Thus, white light-emitting organic EL device of the present invention, the display device, Karoete on the display, or various light emission sources, a lighting device, home lighting, interior lighting, also a kind such as the exposure light source as a lamp, a backlight of a liquid crystal display device, used in useful to a display device.

[0191] 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

[0192] The present invention will be described by way of examples, but the present invention is not limited thereto. Also shown Yore, Ru compounds below in the Examples.

[0193] [of 23]

[0194] [of 24]

α -NPD CBP

[0195] Example 1

"Fabrication of organic EL element OLEDl _ 1"

Substrate and ITO was 150nm deposited on glass as an anode (NH Techno Glass: NA- 45) after the putter Jung, ultrasonic cleaning transparent substrate having the ITO transparent electrode in iso propyl alcohol , 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 heating boat, shed _NPD, CBP, Ir_ 12, BCP, and Alq were placed, respectively it, a vacuum vapor deposition apparatus ( attached to the first vacuum chamber).

[0196] 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.

[0197] 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 alpha NPD, deposition rate 0. lnm / sec ~ 0. 2 nm / a transparent support substrate at a second deposition to a thickness of layer thickness 25 nm, a hole injecting / transporting layer.

[0198] In addition, the deposition rate of CBP of containing said heating boat and Ir 12 of entering the boat independently conductible to are CBP and the light emitting dopant which is a light-emitting host Ir- 12 100: 7 that Do to adjusted deposition to a layer thickness of 30nm as, which a light-emitting layer.

[0199] Next, and heated by supplying an electric current to the boat containing BCP, form a hole blocking layer having a thickness of lOnm at a deposition rate of 0. lm / sec ~ 0. 2 nm / sec. Furthermore, the heating board carrying Alq

3

Heated by energizing the over bets, an electron transporting layer having a thickness of 40nm at a deposition rate of 0. lnm / sec ~ 0. 2 nm / sec.

[0200] Next, after transferring film to an element in the second vacuum chamber while the vacuum to the electron transport layer as, as stainless steel rectangular perforated mask is placed on the electron transport layer installed from the outside of the apparatus remote control to.

[0201] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, a cathode buffer steam Chakusokudo 0. OlnmZ sec ~ 0. 02nmZ seconds at a film thickness of 0. 5 nm by supplying an electric current to the boat lithium fluoride-containing further a provided, then with a cathode having a film thickness 150nm in by energizing the boat containing aluminum deposition rate lnm / sec ~ 2NmZ seconds. Further reducing the organic EL device to a nitrogen atmosphere under a glove box without contacting the atmosphere (Gros was replaced with a purity 99.999% or more of the high purity nitrogen gas Bubokkusu), nitrogen inside as shown in FIG. 5 in in the substituted sealing structure was fabricated organic EL device OLED1- 1.

[0202] Incidentally, barium oxide 105 is water-trapping agent, manufactured by Aldrich of high purity barium oxide Powder, glass with a fluorine resin-based semipermeable membrane of the pressure-sensitive adhesive (manufactured by Micro Tex S- NTF8031Q Nitto Denko) using previously prepared that stuck to the sealing can 104. The adhesion of the sealing can and the organic EL element using an ultraviolet curing adhesive 107 to produce a bonded both sealing elements by irradiating an ultraviolet lamp.

[0203] glass substrates 101 provided with the transparent electrode 5, 102 the hole injection / transport layer, light emitting layer, a hole blocking layer, an organic EL layer formed of an electron transporting layer or the like, 103 indicates a cathode.

[0204] "Preparation of Organic EL element OLED1- 2~ :! one 24"

In the preparation of the organic EL element OLED1- 1, as described in Table 1, the light emitting host, the light-emitting dopant and a hole blocking material, except for changing each in the same manner, the organic EL element OLED 1-. 2 to : to produce a 1-24.

[0205] The resulting organic EL element 〇_LED1 _:! The evaluation as described below was performed on-1-24.

[0206] "external extraction quantum efficiency"

The organic EL element OLED1- 1~: 1- 24 at room temperature (about 23 ° C~25 ° C), 2. performs lighting by constant current condition of 5 mA / cm 2, lighting start immediately after emission luminance (U [cd / m 2] by measuring, to calculate the external extraction quantum efficiency (77). here, the measurement of the emission intensity was used CS 1000 (manufactured by Minolta).

[0207] In addition, the external extraction quantum efficiency was represented by a relative value when the organic EL element OLED1- 1 and 100.

[0208] "emission lifetime"

The organic EL element OLED1-:! At room temperature the ~ 1 24, 2. performed by that continuous lighting to a constant current under the conditions of 5 mA / cm 2, measured the time required to becomes half of the initial luminance (tau /)

1 was 2. Further, emission lifetime were table as a relative value when setting the organic EL element OLED1- 1 and 100.

Table 1 shows the [0209] results obtained.

[0210] [Table 1]

[0211] From Table 1, the organic EL element manufactured using the metal complexes according to the present invention compared to the comparative organic EL element, a high emission efficiency, it is clear that the lifetime of the emission lifetime can be achieved.

[0212] In addition, the combined use of derivatives which have a cyclic structure in which at least one carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives or the carboline derivatives are further substituted at the nitrogen atom in the light-emitting layer, further, Ri by the the use of derivatives having a cyclic structure in which at least one hydrocarbon carbon atoms of the ring constituting the carboline ring of carboline derivatives or the Karubori emission derivatives are further substituted at the nitrogen atom in the hole blocking layer It was observed improvement in the effect described with the present invention.

[0213] Example 2

"Fabrication of organic EL element 〇_LED2 _ 1"

Substrate and ITO was 150nm deposited on glass as an anode (NH Techno Glass: NA- 45) after the putter Jung, ultrasonic cleaning transparent substrate having the ITO transparent electrode in iso propyl alcohol , dried with dry nitrogen gas, a UV ozone cleaning ivy line 5 minutes.

[0214] The transparent supporting substrate was fixed on a substrate holder of a vacuum deposition apparatus available on the market, whereas, five tantalum resistance heating boat, put a-NPD, CBP, Ir-12, BCP, and Alq respectively, mounted in a vacuum deposition apparatus (a first vacuum chamber).

[0215] Further, lithium fluoride tantalum resistance heating boat, placed respectively aluminum to tungsten resistive heating baud bets, attached to a second vacuum chamber of a vacuum deposition apparatus.

[0216] 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 alpha NPD, deposition rate 0. lnm / sec ~ 0. 2 nm / a transparent support substrate at a second deposition to a thickness of layer thickness 30 nm, a hole injecting / transporting layer.

[0217] In addition, the deposition rate of CBP of containing said heating boat and Ir 12 of entering the boat independently conductible to are CBP and the light emitting dopant which is a light-emitting host Ir- 12 100: 7 that Do to adjusted deposition to a layer thickness of 30nm as, which a light-emitting layer.

[0218] Next, and heated by supplying an electric current to the boat containing BCP, deposition rate 0. InmZ sec

To 0. Form a hole blocking layer having a thickness of 10nm at 2nmZ seconds. Further, heating by energizing the heating boat charged with Alq, an electron transporting layer having a thickness of 30nm at a deposition rate of 0. lnm / sec ~ 0. 2nmZ seconds.

[0219] Next, after transferring film to an element in the second vacuum chamber while the vacuum to the electron transport layer as, as stainless steel rectangular perforated mask is placed on the electron transport layer installed from the outside of the apparatus remote control to.

[0220] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, at a steam Chakusokudo 0. Olnm / sec ~ 0. 02nm / sec thickness 0. 5 nm of energizing the boat lithium fluoride-containing the cathode buffer one layer provided, then with a cathode having a thickness 150nm at a deposition rate of L~2nm / sec by energizing the boat containing aluminum. Further reducing the organic EL device to a glove box under a nitrogen atmosphere without contacting the atmosphere (glove box task was replaced with a purity 99.999% or more of the high purity nitrogen gas), nitrogen inside as shown in FIG. 5 in in the substituted sealing structure, to produce an organic EL element OLED1- 1. Incidentally, barium oxide 105 is water-trapping agent, a high-purity barium oxide powder Anoredoritsuchi Co., with adhesive fluororesin-based semipermeable membrane (micro-Tex

Was used previously prepare those stuck to a glass sealing can 104 by S -NTF8031Q by Nitto Denko). The adhesion of the sealing can and the organic EL element using an ultraviolet curing adhesive 107 to produce a bonded both sealing elements by irradiating an ultraviolet lamp. FIG glass substrate 10 1 provided with the transparent electrode at 5, 102 the hole injection / transport layer, light emitting layer, Seiana阻 stop layer, an organic EL layer formed of an electron transporting layer or the like, 103 indicates a cathode.

[0221] "Preparation of the organic EL element OLED2- 2~2- 19"

In the preparation of the organic EL element OLED2- 1, as described in Table 1, the light emitting host, the light-emitting dopant and a hole blocking material, except for changing each in the same manner, the organic EL element OLED2- 2~ 2 - 19 were prepared.

[0222] The obtained organic EL device OLED2-:! KoTsuta About 2-19, external extraction quantum efficiency Nitsu les, Te evaluated in the same manner as in Example 1.

[0223] "emission lifetime"

The organic EL element OLED2 - room temperature the :! ~ 2- 19, 2. 5mA / cm 2 of performed by that continuous lighting to a constant current conditions, the time required to become 90% of the initial luminance (tau / ) to measure the

It was 1 9. The external extraction quantum efficiency, a relative value when the organic EL element OLED2- 1 and 100, the emission lifetime is expressed by a relative value when the organic EL element OLED2- 1 and 100.

Table 2 shows the [0224] results obtained.

[0225] [Table 2] external extraction emission lifetime element No. emission host emitting de one dopant hole blocking material Remarks quantum efficiency (tau 1 9)

0LED2-1 CBP lr-12 BCP 100 100 comparisons

0LED2-2 CBP lr-13 BCP 104 106 comparisons

0LED2-3 CBP Comparison 1 BCP 100 95 comparisons

0LED2-4 CBP 2-1 BCP 122 185 the invention

0LED2-5 CBP 2-3 BCP 129 198 the present invention

0LED2-6 CBP 2-4 BCP 122 177 the present invention

0LED2-7 CBP 2-5 BCP 124 170 the invention

0LED2-8 CBP 2-7 BCP 123 183 the present invention

0LED2-9 CBP 2-10 BCP 117 171 the present invention

0LED2-10 CBP 2-11 BCP 128 188 the invention

0LED2- 11 CBP 2-9 BCP 130 212 the invention

0LED2- 12 ACZ1 2-3 BCP 133 224 the invention

0LED2- 13 ACZ2 2-3 BCP 132 223 the invention

0LED2- 14 CBP 2-3 ACZ1 131 225 the invention

0LED2-15 CBP 2-3 ACZ2 130 220 the present invention

0LED2- 16 ACZ1 2-11 BCP 131 218 the invention

0LED2-17 ACZ2 2-11 BCP 131 212 the invention

0LE02-18 CBP 2-11 ACZ1 130 220 the present invention

0LED2-19 CBP 2-11 ACZ2 130 219 the present invention

[0226] From Table 2, the organic EL element manufactured using the metal complexes according to the present invention compared to the comparative organic EL element, a high emission efficiency, it is clear that the lifetime of the emission lifetime can be achieved.

[0227] In addition, the combined use of derivatives which have a cyclic structure in which at least one carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives or the carboline derivatives are further substituted at the nitrogen atom in the light-emitting layer, further, Ri by the the use of derivatives having a cyclic structure in which at least one hydrocarbon carbon atoms of the ring constituting the carboline ring of carboline derivatives or the Karubori emission derivatives are further substituted at the nitrogen atom in the hole blocking layer It was observed improvement in the effect described with the present invention.

[0228] Example 3

"Organic EL element OLED3 - 1 of Preparation"

Substrate was 150nm deposited ΙΤΟ on glass as an anode (Nyuita Techno Glass: ΝΑ- 45) after the putter Jung, ultrasound transparent substrate having the ITO transparent electrode in iso- propyl alcohol washed, dried with dry nitrogen gas, into one row 5 minutes to UV ozone cleaning. [0229] The transparent supporting substrate was fixed on a substrate holder of a vacuum deposition apparatus available on the market, whereas, five tantalum resistance heating boat, m-MTDATXA, Hl, Ir-12, BCP, and Alq each placed It was attached to a vacuum vapor deposition apparatus (a first vacuum chamber).

[0230] Further, lithium fluoride tantalum resistance heating boat, placed respectively aluminum to tungsten resistive heating baud bets, attached to a second vacuum chamber of a vacuum deposition apparatus.

[0231] First, after the vacuum of the first vacuum chamber to 4 X 10- 4 Pa, and heated by supplying an electric current to the boat containing M_MTDATXA, transparent at a deposition rate of 0. InmZ sec ~ 0. 2 nm / sec It was deposited to a thickness of the film thickness 40nm to support base plate, a hole injecting Z transporting layer.

[0232] Furthermore, by conductible Ir_ and the heating boat charged with HI 12 of entering the boat independently is HI and the light emitting dopant which is a light-emitting host Ir- 12 deposition rate of 100: 7 that Do to adjusted deposition to a layer thickness of 30nm as, which a light-emitting layer.

[0233] Next, and heated by supplying an electric current to the boat containing BCP, deposition rate 0.1: form a hole blocking layer having a thickness of 10nm at ~ 0. 2n m / sec. Further, heating by energizing the heating boat charged with Alq, an electron transporting layer having a thickness of 20nm at a deposition rate of 0. lnm / sec ~ 0. 2 nm / sec.

[0234] Next, after transferring film to an element in the second vacuum chamber while the vacuum to the electron transport layer as, as stainless steel rectangular perforated mask is placed on the electron transport layer installed from the outside of the apparatus remote control to.

[0235] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, at a steam Chakusokudo 0. Olnm / sec ~ 0. 02nm / sec thickness 0. 5 nm of energizing the boat lithium fluoride-containing the cathode buffer one layer provided, then put by energizing the boat containing aluminum at a deposition rate of lnm / sec ~ 2 nm / sec cathode thickness 150 nm. Further reducing the organic EL device to a nitrogen atmosphere under a glove box without contacting the atmosphere (Gros was replaced with a purity 99.999% or more of the high purity nitrogen gas Bubokkusu), nitrogen inside as shown in FIG. 5 in in the substituted sealing structure was fabricated organic EL device OLED3- 1. Incidentally, barium oxide 105 is water-trapping agent, a high-purity barium oxide powder Aldo rich Inc., glass sealing by a fluororesin semipermeable membrane of the pressure-sensitive adhesive (Miku port tex S -NTF8031Q by Nitto Denko) It was used to prepare those affixed to the can 104 in advance. The adhesion of the sealing can and the organic EL device using the ultraviolet ray curable adhesive 1 07, to produce a bonded both sealing elements by irradiating an ultraviolet lamp. Glass substrate Oite 101 having a transparent electrode 5, 102 the hole injection / transport layer, light emitting layer, a hole blocking layer, an organic EL layer formed of an electron transporting layer or the like, 103 indicates a cathode.

[0236] "Preparation of the organic EL element OLED3 _ 2~3 _ 23"

In the preparation of the organic EL element OLED3- 1, as described in Table 3, the light emitting host

The light-emitting dopant and a hole blocking material, except for changing each in the same manner, the organic EL element OLED3 - to prepare a 2-3 _ 23.

[0237] The resulting organic £ and device Rei_1 ^^) 3 _ 1-3 _ 23 Ni'ite was evaluated in external extraction quantum efficiency Nitsu les, similarly to Example 1 Te method.

[0238] "voltage rise"

The organic EL element OLED3 - :! ~ 3- 23 to 25 ° C, 2. performs continuous lighting by constant current condition of 5 mA / cm 2, the driving voltage when it is half of the initial luminance, initial degree the rise from the driving voltage were measured.

[0239] The external extraction quantum efficiency, voltage increase is expressed as a relative value when the organic EL element OLED3- 1 and 100.

Table 3 shows the [0240] results obtained.

[0241] [Table 3]

Out external birds

Device No. emission host emitting dopant hole blocking material voltage rise Remarks

Star "rate

oooooooooo 0LED3-1 H1 I r-12 BCP 100 100 comparisons

0LED3-2 H1 I r-13 BCP 102 98 comparisons

0LED3-3 H1 Comparison 1 BCP 101 105 comparisons

0LED3-4 H1 3-1 BCP 1 19 87 invention

0LED3-5 H1 3-7 BCP 1 14 90 invention

0LED3-6 H1 3-9 BCP 127 82 invention

0LED3-7 H1 3-11 BCP 122 85 invention

0LED3-8 H1 3-19 BCP 120 88 invention

0LED3-9 H1 3-25 BCP 1 17 90 invention

0LED3-10 H1 3-29 BCP 126 85 invention

H1 3-27 BCP 128 81 invention

ACZ1 3-29 BCP 131 78 present invention

ACZ2 3-29 BCP 131 79 present invention

H1 3-29 ACZ1 132 77 invention

H1 3-29 ACZ2 130 78 invention

ACZ1 3-27 BCP 130 76 present invention

ACZ2 3-27 BCP 130 76 present invention

H1 3-27 ACZ1 131 75 invention

H1 3-27 ACZ2 131 75 invention

ACZ1 3-1 BCP 129 78 present invention

ACZ2 3-7 BCP 125 77 present invention

H1 3-19 ACZ3 127 80 invention

H1 3-25 ACZ3 130 80 invention

[0242] From Table 3, the organic EL element manufactured using the metal complexes according to the present invention compared to the comparative organic EL element, a high emission efficiency, it is clear that the low voltage rise can be achieved.

[0243] In addition, the combined use of derivatives which have a cyclic structure in which at least one carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives or the carboline derivatives are further substituted at the nitrogen atom in the light-emitting layer, further, Ri by the the use of derivatives having a cyclic structure in which at least one hydrocarbon carbon atoms of the ring constituting the carboline ring of carboline derivatives or the Karubori emission derivatives are further substituted at the nitrogen atom in the hole blocking layer It was observed improvement in the effect described with the present invention.

[0244] Example 4

"Organic EL device OLED 4 - 1 Preparation"

In the creation of light-emitting layer in Example 3, the light emitting host is HI and the deposition rate of a certain Ir- 12 in light emitting dopant 100: 7, 100: organic EL device in the same manner as in Example 3 except that the 4 It created the OLED4- 1.

[0245] In the preparation of the "organic EL element OLED4- 2~4 19 Preparation of" the organic EL device OLED4-1, as described in Table 4, the light emitting host, the light-emitting dopant and a hole blocking material, each change except that the in the same manner, to prepare an organic EL element OLED4- 2~4 11.

[0246] The obtained organic EL device OLED 4 - For :! ~ 4 19, the following evaluations were carried out.

[0247] "external extraction quantum efficiency"

The organic EL element OLED4 - :! ~ 4_ 19 ~25 ° at RT (about 23 performs lighting by constant current conditions of 2. 5 mA / cm 2, lighting start immediately after emission luminance (U [cd / m 2] by measuring and calculating the external extraction quantum efficiency () the measurement of emission luminance, CS -.. 1000 (manufactured by Minolta) the external extraction quantum efficiency, the organic EL element OLED 4- 1 was represented by a relative value when the 100.

[0248] "emission lifetime"

Organic £ and device Rei_1 ^: 04_ 1~4_ 19 at room temperature for 2. performed by that continuous lighting to a constant current under the conditions of 5 mA / cm 2, the time required to becomes half of the initial luminance (tau /) to measure the

1 was 2. The light-emitting lifetime, the organic EL element OLED4- 1 as 100, was expressed by a relative value.

Table 4 shows the [0249] results obtained.

[0250] [Table 4]

External extraction emission ¾ =

Device No. emission phosphorylase emitting de - Pan Bok hole blocking material Remarks quantum efficiency

0LED4-1 HI lr-12 BCP 100 100 comparisons

0LED4-2 HI lr-13 BCP 101 104 comparisons

0LE04-3 HI Comparison 1 BCP 100 85 comparisons

0LED4-4 HI 4-1 BCP 129 199 the invention

0LED4-5 HI 4-5 BCP 123 190 the invention

0LED4-6 HI 4-7 BCP 135 221 the present invention

0LED4-7 H1 4-9 BCP 132 216 the invention

0LED4-8 H1 4-20 BCP 130 200 the invention Ma

0LE04-9 HI 4-21 BCP 134 220 the present invention

0LED4-10 H1 4-23 in in BCP 125 197 the invention

0LED4-11 H1 BCP 133 215 the invention

0LED4-12 ACZI BCP 136 230 the invention

0LE04-13 ACZ2 4-1 BCP 135 232 the invention

0LED4-14 H1 4-1 ACZ1 133 233 the invention

0LED4-15 H1 4-1 ACZ2 132 234 the invention

0LED4-16 ACZI 4-1 BCP 135 245 the present invention

0LED4-17 ACZ2 4-25 BCP 135 240 the present invention

0LED4-18 H1 ACZ1 136 241 the present invention

0LED4-19 H1 ACZ2 135 239 the present invention

[0251] From Table 4, the organic EL element manufactured using the metal complexes according to the present invention compared to the comparative organic EL element, a high emission efficiency, it is clear that the lifetime of the emission lifetime can be achieved. Further, by combining the derivative with a cyclic structure in which at least one carbon atom of the hydrocarbon ring constituting a carboline ring of carboline derivatives or the carboline derivatives are further substituted at the nitrogen atom in the light emitting layer, carboline by using a derivative having a cyclic structure in which at least one derivative or a carbon atom of a hydrocarbon ring constituting a carboline ring of the carboline derivative conductor is further substituted with a nitrogen atom to the hole blocking layer, with the present invention improvement of the effect of the described was observed.

[0252] Example 5

"Fabrication of organic EL element OLED5- 1"

Substrate was 150nm deposited ΙΤΟ on glass as an anode (Nyuita Techno Glass: ΝΑ- 45) after patterning, ultrasonic cleaning transparent substrate having the ITO transparent electrode in iso- propyl alcohol , dried with dry nitrogen gas, into one row 5 minutes to UV ozone cleaning. [0253] The transparent supporting substrate was fixed on a substrate holder of a vacuum deposition apparatus available on the market, whereas, five tantalum resistance heating boat, m-MTDATXA, Hl, Ir-12, BCP, and Alq each

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

[0254] 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.

[0255] First, after the vacuum of the first vacuum chamber to 4 X 10- 4 Pa, and heated by supplying an electric current to the boat containing M_MTDATXA, transparent at a deposition rate of 0. InmZ sec ~ 0. 2 nm / sec It was deposited to a thickness of the film thickness 30nm to support base plate, a hole injecting Z transporting layer.

[0256] Furthermore, by conductible Ir_ and the heating boat charged with HI 12 of entering the boat independently is HI and the light emitting dopant which is a light-emitting host Ir- 12 deposition rate of 100: 7 that Do to adjusted deposition to a layer thickness of 30nm as, which a light-emitting layer.

[0257] Next, and heated by supplying an electric current to the boat containing BCP, deposition rate 0. InmZ sec

To 0. Form a hole blocking layer having a thickness of 10nm at 2 nm / sec. In addition, the heating carrying Alq

3

Heated by energizing the boat, an electron transporting layer having a thickness of 30nm at a deposition rate of 0. lnm / sec ~ 0. 2 nm / sec.

[0258] Next, after transferring film to an element in the second vacuum chamber while the vacuum to the electron transport layer as, as stainless steel rectangular perforated mask is placed on the electron transport layer installed from the outside of the apparatus remote control to.

[0259] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, at a steam Chakusokudo 0. Olnm / sec ~ 0. 02nm / sec thickness 0. 5 nm of energizing the boat lithium fluoride-containing the cathode buffer one layer provided, then put by energizing the boat containing aluminum at a deposition rate of lnm / sec ~ 2 nm / sec cathode thickness 150 nm. Further reducing the organic EL device to a nitrogen atmosphere under a glove box without contacting the atmosphere (Gros was replaced with a purity 99.999% or more of the high purity nitrogen gas Bubokkusu), nitrogen inside as shown in FIG. 5 in in the substituted sealing structure was prepared organic EL element OLED1 _ 1.

[0260] Incidentally, barium oxide 105 is water-trapping agent, a high-purity barium oxide powder manufactured by Aldrich, glass with a fluorine resin-based semipermeable membrane of the pressure-sensitive adhesive (micro Tex S- NTF8031Q day Tokyo Electric Ltd. E) using previously prepared that stuck to the sealing can 104. Sealing can and using a UV curing adhesive 107 for bonding the organic EL device, and the UV lamp to prepare a bonded sealing element both in the child irradiation. FIG glass substrate 101 provided with the transparent electrode at 5, 102 the hole injection / transport layer, light emitting layer, a hole blocking layer, an organic EL layer formed of an electron transporting layer or the like, 103 indicates a cathode.

[0261] "Preparation of the organic EL element OLED5 _ 2~5 _ 25"

In the preparation of the organic EL element OLED5- 1, as described in Table 5, the light emitting host

The light-emitting dopant and a hole blocking material, except for changing each in the same manner, the organic EL element OLED 5 - to produce a 2-5 _ 25.

[0262] The resulting organic £ and device Rei_1 ^^) 5 _ 5 _ 25 Ni'ite was evaluated in external extraction quantum efficiency Nitsu les, similarly to Example 1 Te method.

[0263] "emission lifetime"

The organic EL element OLED 5 - room temperature the :! ~ 5- 25, 2. 5mA / cm 2 of performed by that continuous lighting to a constant current conditions, the time required to become 90% of the initial luminance (tau / ) to measure the

It was 1 9. The external extraction quantum efficiency, a relative value when the organic EL element OLED5- 1 and 100, emission lifetime was expressed by a relative value when the organic EL element OLED5- 1 and 100.

Table 5 shows the [0264] results obtained.

[0265] [Table 5]

External extraction Hatsusaki Lolo

Device No. emission host emitting dopant hole blocking material Remarks

ooooo quantum efficiency 1/9)

■ mmmmm 5-1 H1 lr -12 BCP 100 100 comparisons

0LED5-2 H1 lr -13 BCP 102 103 comparisons

o H1 Comparison 1 BCP 101 99 comparisons

0LED5-4 H1 5-1 BCP 120 140 the invention

0LED5-5 H1 5-2 BCP 120 150 the invention

0LED5-6 H1 5-3 BCP 121 167 the invention

0LED5-7 H1 5-4 BCP 120 175 the invention

H1 5-9 BCP 122 141 the invention

0LED5-9 H1 5-12 BCP 118 170 the invention

H1 5 -13 BCP 121 140 the invention

0LED5 -11 H1 5-14 BCP 122 138 the invention

0LED5 -12 H1 5-15 BCP 120 160 the invention

0LED5 -13 H1 5-16 BCP 121 172 the invention

ACZ1 5 -9 BCP 124 190 the present invention

ACZ2 5 -9 BCP 125 192 the invention

H1 5-9 ACZ1 124 190 the invention

0LED5 -17 H1 5-9 ACZ2 124 191 the invention

0LED5 -18 ACZ1 5-4 BCP 123 191 the invention

0LED5 -19 ACZ2 5-4 BCP 124 193 the invention

0LED5 -20 H1 5-4 ACZ1 124 195 the invention

H1 5-4 ACZ2 124 199 the invention

H1 5 -2 ACZ1 122 188 the invention

H1 5 -10 ACZ1 124 188 the invention

0LED5 -24 H1 5-14 ACZ1 123 186 the invention

0LED5 -25 H1 5-16 ACZ1 122 197 the invention

[0266] From Table 5, the organic EL element manufactured using the metal complexes according to the present invention compared to the comparative organic EL element, a high emission efficiency, it is clear that the lifetime of the emission lifetime can be achieved. Further, by combining the derivative with a cyclic structure in which at least one carbon atom of the hydrocarbon ring constituting a carboline ring of carboline derivatives or the carboline derivatives are further substituted at the nitrogen atom in the light emitting layer, carboline by using a derivative having a cyclic structure in which at least one derivative or a carbon atom of a hydrocarbon ring constituting a carboline ring of the carboline derivative conductor is further substituted with a nitrogen atom to the hole blocking layer, with the present invention improvement of the effect of the described was observed.

[0267] Example 6

"Fabrication of organic EL element OLED6- 1"

In the preparation of the organic EL element 3-1 of Example 3, when the light emitting layer formation, the light emitting host is HI and the deposition rate of a certain Ir- 12 in light emitting dopant 100: 7, 100: same except for changing the 5 an organic EL device was prepared OLED6- 1 to to. [0268] "Preparation of Organic EL element OLED6- 2 6- 20"

In the preparation of the organic EL element OLED6- 1, as described in Table 6, the light emitting host, the light-emitting dopant and a hole blocking material, except for changing each in the same manner, the organic EL element OLED6 _ 2 6 _ to prepare a 20. Rre the obtained organic EL device OLED6 _ 1 6 _ 20 Te, was evaluated in external extraction quantum efficiency Nirre, similarly to Example 1 Te method.

[0269] "voltage rise"

The organic EL element OLED6- :! 6- 20 performs continuous lighting by constant current conditions of 25 ° C 2. 5mA / cm 2 , the driving voltage when it is half of the initial luminance, initial degree driven electrostatic It was measured rise from the pressure.

[0270] The external extraction quantum efficiency, voltage increase is expressed as a relative value when the organic EL element OLED6- 1 and 100.

[0271] [Table 6]

From the 0272] Table 6, the organic EL element manufactured using the metal complexes according to the present invention compared to the comparative organic EL element, a high emission efficiency, it is clear that the low voltage rise can be achieved. Furthermore, by combining an inductive element having a ring structure at least one hydrocarbon carbon atoms of the ring constituting the carboline ring of carboline derivatives or the carboline derivatives are further substituted at the nitrogen atom in the light emitting layer, carboline by using a derivative having a cyclic structure in which at least one derivative or a carbon atom of a hydrocarbon ring constituting a carboline ring of the carboline derivatives are further substituted at the nitrogen atom in the hole blocking layer, further according to the present invention improvement of the effect was observed.

[0273] Example 7

"Preparation of a full-color display device"

(Preparation of blue light emitting element)

The organic EL element OLED1- 7 of Example 1 was used as a blue light emitting element.

[0274] (Preparation of green light emitting element)

The Ir_ l was used as the green light emitting element.

[0275] (Preparation of red light-emitting element)

The Ir_ 9 was used as a red light emitting element.

[0276] prepared in the above, each red, green, and juxtaposing blue light emitting organic EL element on the same substrate, to produce an active matrix type full color display apparatus having a configuration as described in Figure 1, in Figure 2 showed only schematic drawing of a display section a of the display device manufactured. That is, on the same substrate, a wiring section containing plural scanning lines 5 and plural data lines 6, a plurality of pixels 3 juxtaposed (the color of light emission pixels in the red area, the pixels of the green region, blue region of the pixel, etc.) has become the wiring portion of the run 查線 5 and plural data lines 6 from the respective conductive material, the lines 5 and the lines 6 being crossed with each other at a right angle, and connected with the pixels 3 at the crossed points (not shown in detail). Wherein the plurality of pixels 3, the organic EL elements corresponding to the respective emission colors, and each switch ing transistor and the driving transistor is an active device is driven by an active matrix scheme provided, it is 查信 No. run from the scanning line 5 Once applied, it receives the image data signal from the data lines 6, and emit light corresponding to the received image data. Each red In this way, green, by appropriately, to juxtapose the pixels of the blue, to produce a full-color display device.

[0277] By driving the full color display device, the luminance has a high ingredients high durability, and, it was found that sharp full-color video display can be obtained.

[0278] Example 8

In the preparation of the blue light-emitting element of Example 7 "Preparation of full-color display device", an organic EL element OLED1- 7, it was except for changing the organic EL element OLED2- 7 in the same manner to produce a full color display device.

[0279] By driving the full color display device, the luminance has a high ingredients high durability, and, it was found that sharp full-color video display can be obtained.

[0280] Example 9

"Preparation of a full-color display device"

In the preparation of the blue light-emitting element of Example 7, the organic EL element OLED1- 7, the organic EL element OLED3- 4

It was changed to similarly was produced a full-color display device.

[0281] By driving the full color display device, the luminance has a high ingredients high durability, and, it was found that sharp full-color video display can be obtained.

[0282] Example 10

"Preparation of a full-color display device"

In the preparation of the blue light-emitting element of Example 7, the organic EL element OLED1- 7, it was except that the organic EL element OLED4- 4 in the same manner to produce a full color display device.

[0283] By driving the full color display device, the luminance has a high ingredients high durability, and, it was found that sharp full-color video display can be obtained.

[0284] Example 11

"Preparation of a full-color display device"

In the preparation of the blue light-emitting element of Example 7, the organic EL element OLED1- 7, it was except that the organic EL element OLED5- 4 in the same manner to produce a full color display device.

[0285] By driving the full color display device, the luminance has a high ingredients high durability, and, it was found that sharp full-color video display can be obtained.

[0286] Example 12

"Preparation of a full-color display device"

In the preparation of the blue light-emitting element of Example 7, the organic EL element OLED1- 7, it was except that the organic EL element OLED6- 5 in the same manner to produce a full color display device.

[0287] By driving the full color display device, the luminance has a high ingredients high durability, and, it was found that sharp full-color video display can be obtained.

[0288] Example 13

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

Example 1 of the transparent electrode substrate of the electrode patterns and Jung to 20 mm X 20 mm, and a film of an NPD in the 25nm thick shed as a hole injection / transport layer in the same manner as the actual Example 1 thereon, further, the heating boat and the present invention compound 1 _ 5 of containing boat and Ir_ 9 of the incoming ivy boat energized independently are CBP and the light emitting dopant which is a light-emitting host compound of the present invention 1 _ 5 and Ir_ containing the CBP 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.

[0289] Then, a hole blocking layer was 10nm film forming of BCP. Furthermore, providing the film with an electron transport layer of Alq with 40 nm.

[0290] Next, in the same manner as in Example 1, was placed a substantially square perforated mask having the same shape as the stainless steel of the transparent electrode on the electron injection layer, lithium fluoride 0. 5 nm, and a cathode as a single layer cathode buffer aluminum 150nm was deposited film forming as.

[0291] was prepared flat lamp is equipped with the element sealing can similar method and similar structure as in Example 1. It shows a schematic view of a planar lamp in FIG. The plan schematic in FIG. 6 (b) in FIGS. 6 (a) shows a schematic cross-sectional view.

[0292] almost white light obtained was energized to this plane lamp, Rukoto force pictmap Ca can be used as a lighting device ゝ ivy.

[0293] Example 14

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

In the preparation of the white light emitting device of Example 13, the compounds of the present invention 1-5 except that the 2-7 was prepared white illumination device in the same manner as in Example 13.

[0294] almost white light obtained was energized to this plane lamp was found Rukoto be used as a lighting device.

[0295] Example 15

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

Ore in the production of white light emitting device of Example 13, Te, the present compound 1 one 5 was changed to 3-2 was produced white illumination device in the same manner as in Example 13.

[0296] almost white light obtained was energized to this plane lamp, Rukoto force pictmap Ca can be used as a lighting device ゝ ivy.

[0297] Example 16

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

In the preparation of the white light emitting device of Example 13, to prepare a white illumination device except that the compound 1-5 to 4-4 in the same manner as in Example 13.

[0298] almost white light obtained was energized to this plane lamp was found Rukoto be used as a lighting device.

[0299] Example 17

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

Ore in the production of white light emitting device of Example 13 Te,, Compound 1 _ 5 5 - was prepared a white illumination device in the same manner as in Example 13 except that the 1.

[0300] almost white light obtained was energized to this plane lamp, Rukoto force pictmap Ca can be used as a lighting device ゝ ivy.

[0301] Example 18

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

Ore in the production of white light emitting device of Example 13 Te, to produce a white illumination device except for changing Compound 1 5 6 5 in the same manner as in Example 13.

[0302] almost white light obtained was energized to this plane lamp, Rukoto force pictmap Ca can be used as a lighting device ゝ ivy.

[0303] Example 19

"Fabrication of organic EL element OLED7 _ 1 ~ 7- 13"

In Example 1, by changing the light-emitting dopant in Ir_ l, except that the hole blocking material was changed as shown in Table 7 in the same manner, the organic EL element OLED 7 - were prepared :! ~ 7-13.

[0304] External extraction quantum efficiency of each element obtained, measurement of the emission life was conducted in the same manner as described in Example 1.

[0305] As this time, 100 both OLED7- 1 values ​​were expressed the value of each organic EL element sample by a relative value. The results obtained are shown in Table 7.

[0306] [Table 7]

From the 0307] Table 7, the organic EL element of the organic EL device material of the present invention was used for the hole blocking material is compared to the ratio 較素Ko, a high luminous efficiency, it was found that the emission life can be obtained. It should be noted, calling the device of the present invention

All light color was green.

Industrial Applicability

[0308] The present invention, useful organic EL element material for the organic EL element obtained by using an organic EL element material, the emission wavelength is controlled, it showed high luminous efficiency, and, the light emission life it is possible to provide a long organic EL device, a lighting device and a display device.

Claims

The scope of the claims
Following general formula (1) or, the metal complex having tautomers as partial structure of the general formula (1), the following general formula (2) or, the general formula (2) tautomeric the partial structure of metallic complex having as a general formula (3) or a metal complex that have a tautomer of the general formula (3) as a partial structure represented by the following general formula (4) or, said formula (4) metal complex having a tautomeric as a partial structure represented by the following general formula (5) or, said formula (5) a metal complex having tautomers and as a partial structure or, the following general formula (6) or the organic elect port luminescent device material which is a metal complex having the general formula tautomers of (6) as a partial structure.
[Formula 1] general formula (1)
Wherein, Z11 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. R, R, R each represents a hydrogen atom or a substituent. M is the Periodic Table of the Elements
11 represents the 12 13 Group 8 in the 11 -10 metals. ]
[Formula 2] formula (2)
Wherein, Z21 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. R, R, R each represents a hydrogen atom or a substituent. M represents a group 8-10 metal in the periodic table. ]
[Formula 3] Formula (3)
Wherein, Z31 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X, chi, chi is each may have a substituent group carbon atom or a nitrogen atom
31 32 33
It represents, but at least two are nitrogen atom or a N (R) - (wherein, R represents Hydrogen atom
3 3
It represents a substituent. ) Represents the. C represents a carbon atom. M is a Group 8 in the periodic table
31 31
Representing the 10 metals. The bond between C and N, the bond between the N and X, between X and X
31 33 32 33 bond, the bond between X and X, bond each single bond or a double bond between C and X
31 32 31 31
A representative. ]
[Formula 4] General formula (4)
I! '. \
-43 ^ 41: '
,, Z4,1 Roh '
Wherein, Z41 represents an atomic group necessary for forming an aromatic heterocyclic ring. X, X is a substituted
Represents a good carbon atom or a nitrogen atom which may have a 41 42 group, at least one of which ChissoHara child or N (R) (where, R represents. A hydrogen atom or a substituent group) . M is
4 4 41
Represents a group 8-10 metal in the periodic table. C, C, C is each carbon atom
41 42 43
Represent. M represents a group 8-10 metal in the periodic table. The bond between C and C
41 41 42
, The bond between C and X bond between X and X, the bond between X and C, the bond between C and C represents a single bond or a double bond. ]
[Chem 5] General formula (5)
Wherein, Z51 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X represents an oxygen atom or a sulfur atom. R, R is a hydrogen atom or location
It represents a 51 51 52 substituent. M represents a group 8-10 metal in the periodic table. ]
51
[Formula 6]
The general formula (6)
61,
Figure 61
Wherein, Z61 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X, chi, chi is each may have a substituent group carbon atom or a nitrogen atom
61 62 63
It represents but represents at least one nitrogen atom. Μ is a group 8-10 of the periodic table
61
Representing the metal. ]
[2] the above general formula (1) or, organic elect port luminescence according to claim 1, characterized in that a metal complex having a tautomer of the general formula (1) as a partial structure element material.
[3] the above general formula (1) or, that Z11 in the metal complex having a tautomer of the general formula (1) as a partial structure represents an atomic group necessary for forming an aromatic heterocyclic ring organic elect port luminescent device material according to claim 2, characterized. [4] the above general formula (2) or, organic elect port luminescence according to claim 1, characterized in that a metal complex having a tautomer of the general formula (2) as a partial structure element material.
[5] the above general formula (3) or, organic elect port luminescence according to claim 1, characterized in that a metal complex having a tautomer of the general formula (3) as a partial structure element material.
[6] the above general formula (3) or, in the metal complex having a tautomer of the general formula (3) as a partial structure, X represents a carbon atoms which may have a substituent, X, X nitrogen atom or
31 32 33
_N (R) _ (wherein, R represents. A hydrogen atom or a substituent), characterized in that the representative of the
3 3
Organic elect port luminescent device material according to claim 5.
[7] the above general formula (4) or, organic elect port luminescence according to claim 1, characterized in that a metal complex having a tautomer of the general formula (4) as a partial structure element material.
[8] the above general formula (5) or, organic elect port luminescence according to claim 1, characterized in that a metal complex having a tautomer of the general formula (5) as a partial structure element material.
[9] the above general formula (5) or, according to a range Section 8 claims, characterized in that represents X, a sulfur atom in the metal complex having a tautomer of the general formula (5) as a partial structure organic
51
Elect opening luminescent element material.
[10] the above general formula (6) or, organic elect port luminescence according to claim 1, characterized in that a metal complex having a tautomer of the general formula (6) as a partial structure element material.
[11] the general formula (6) or, claimed in the metal complex having tautomers as partial structure of the general formula (6), X, at least one of X is characterized by a nitrogen atom range of
61 63
Organic elect port luminescent device material according to paragraph 10.
[12] In Formula (1), wherein which is a M force S, iridium or platinum
11
Organic elect port luminescent device material according to the range the second term.
[13] The organic-elect opening luminescent device material according to claim 12, characterized in that represents an atomic group necessary to Z11 in the general formula (1) forms an aromatic heterocyclic ring [14] in the general formula (2), wherein which is a M 1 iridium or platinum
twenty one
Organic elect port luminescent device material according to item 4 range.
[15] In the general formula (3), wherein which is a Μ force iridium or platinum
31
Organic elect port luminescent device material according to paragraph 5 range.
[16] the above general formula (3), X represents a carbon atoms which may have a substituent, X, is Χ nitrogen
31 32 33 atom or - N (R) - (wherein, R represents a hydrogen atom or a substituent.) To represent
3 3
Organic elect port luminescent device material according to the range Section 15 claims characterized.
[17] In the general formula (4), wherein which is a M force iridium or platinum
41
Organic elect port luminescent device material according to paragraph 7 range.
[18] In Formula (5), wherein which is a M force iridium or platinum
51
Organic elect port luminescent device material according to the range Section 8.
[19] claims, characterized in that represents X, a sulfur atom in the general formula (5) 18
51
Organic elect port luminescent device material according to item.
[20] In Formula (6), wherein which is a M 1 iridium or platinum
61
Organic elect port luminescent device material according to the range Section 10.
[21] In the above general formula (6), X, to characterized in that represent at least one nitrogen atom Χ
61 63
Organic elect port luminescent device material according to paragraph 20 claims that.
[22] The organic-elect opening luminescent element characterized by containing the organic-elect opening luminescent device material according to claim 1.
[23] 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 Noreminessensu device material according to claim 1.
[24] have a hole blocking layer as a constituent layer, organic elect port Rumine' sensing element characterized in that the hole blocking layer contains the organic elect port luminescent device material according to claim 1.
[25] a light-emitting layer as a constituent layer, light emitting layer, a ring structure in which at least one carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives or the carboline induced body is replaced by a nitrogen atom organic elect port device as described in paragraph 22 claims, characterized in that it contains a derivative having.
[26] it has a hole blocking layer as a constituent layer, the hole blocking layer, and at least one carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives or the local borinic derivative is replaced by a nitrogen atom organic elect port device as described in paragraph 22 claims, characterized in that it contains a derivative having a have ring structure.
[27] display device characterized by having an organic-elect opening device as described in the scope paragraph 22 claims.
[28] an illumination apparatus characterized by having an organic-elect opening device as described in paragraph 22 claims.
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