WO2008044723A1 - 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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WO2008044723A1
WO2008044723A1 PCT/JP2007/069822 JP2007069822W WO2008044723A1 WO 2008044723 A1 WO2008044723 A1 WO 2008044723A1 JP 2007069822 W JP2007069822 W JP 2007069822W WO 2008044723 A1 WO2008044723 A1 WO 2008044723A1
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Motoaki Sugino
Masato Nishizeki
Tomohiro Oshiyama
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Konica Minolta Holdings, Inc.
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    • H01L51/5012Electroluminescent [EL] layer

Abstract

Disclosed is an organic EL device using an organic EL device material having controlled emission wavelength, high luminous efficiency and long emission life. Also disclosed are a display and an illuminating device. Specifically disclosed is an organic EL device material represented by the following general formula (1a). [In the formula (1a), A represents a cyclic group; B represents a cyclic group; and A is a group represented by the general formula (1b) below, or alternatively the compound represented by the general formula (1a) has a group represented by the general formula (1b) below asa substituent: (In the formula (1b) wherein X represents O, S or N-R2 (wherein R2 represents an alkyl group, an aryl group or a heteroaryl group); Z1, Z2, Z3 and Z4 represent N or -CR4= (wherein R4 represents a hydrogen atom or a substituent), and one of them is N); X1 and X2 represent C, N or O; L1 represents an atomic group forming a bidentate ligand together with X1 and X2; m1 represents 1, 2 or 3, m2 represents 0, 1 or 2 and m1 + m2 is 2 or 3; and M1 represents a group 8-10 metal of the periodic table.]

Description

Specification

Organic elect port luminescent device material, an organic-elect opening DEVICE, DISPLAY DEVICE AND ILLUMINATING 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, an organic EL element! /, U) can be mentioned. Inorganic elect port luminescent element in order to drive the force light emitting device has been used as a planar light source requires a high AC voltage. The organic EL element has a structure in which between a cathode and an anode of the light-emitting layer containing a compound which emits the electrons and holes to note entering into the light emitting layer, to produce an exciton by recombination , the excitons is an element that emits light by utilizing emission (fluorescence 'phosphorescence) of light at the time of deactivation, and can emit light in several V~ tens V extent of voltage, further self-luminous rich in viewing angle for certain space-saving because visibility is complete solid element Kogu thin film, has attracted attention in view of portability or the like.

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

[0004] In Japanese Patent No. 3093796 publication, stilbene derivatives, distyryl Rua Lee alkylene derivatives or is doped with a slight amount of a fluorescent compound tris styryl Rua Lee alkylene derivatives, improvement of emission luminance, to achieve a long life of the element there. The host 8-hydroxyquinoline aluminum complex as a host compound, this element having an organic light-emitting layer doped with a slight amount of a fluorescent substance (e.g., JP 63- 264692 discloses), 8-hydroxyquinoline aluminum Yes No complex as compounds, elements having the same organic light-emitting layer doped with a quinacridone type dye (e.g., JP-3- 255190 JP), and the like. [0005] 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%

[0006] where reporting of the organic EL element which utilizes phosphorescence than the force Princeton from excited triplet (MA Baldo et al, Nature, 395, pp. 151 to;. 154 (1998)) force is S Since that time, have come to be active is the study of material that exhibits phosphorescence at room temperature.

[0007] For example, MA Baldo et al., Nature, 403 Volume, No. 17, pp. 750-753 (2000

), Also disclosed in U.S. Patent No. 6, 097, 147 Pat like.

[0008] With the excited triplet, theoretically luminous efficiency is 4 times of the case of the excited singlet for the upper limit of the internal quantum efficiency is 100%, almost the same performance is obtained with the cold cathode tube it is also considered for lighting applications because of the potential that.

[0009] For example, S. Lamansky et al., J. Am. Chem. Soc., 123 volumes, in 4304 (2001) and the like, synthetic test many compounds mainly heavy metal complexes such as iridium complexes 討It is.

[0010] Moreover, the aforementioned MA Baldo et al., Nature, 403, pp. 17 No. in the page 750-753 (200 0 years), tris (2-phenylene Rubirijin) consider using iridium as a dopant It is.

[0011] Other, ME Tompson, etc., The 10th International Workshop on In organic and Organic Electroluminescence (EL '00, Hamamatsu) ί Nobi Rere Te, L Ir (acac) as Dono down Bok, for example, (ppy) Ir ( the acac), also Moon- Jae Youn. 0g, T etsuo Tsutsui, etc., still the 10th International Workshop on Inorga nic and Organic Electroluminescence (EL, 00, Hamamatsu) Te ί Nobi Rere, tris (2- (as Dono cement ρ- tolyl) pyridine) iridium (Ir (ptpy)), tris (benzo [h] quinoline

) Iridium (Ir (bzq) conducted a study using), and the like! /, Ru (It should be noted that these metal complexes are generally referred to as a ortho-metalated iridium complex! /, Ru.).

[0012] In addition, the S. Lamansky et al., J. Am. Chem. Soc., 123, pp. 4304 (20 2001) and also in Patent Document 14 or the like, an attempt to devices by using a variety of iridium complexes It has been made.

[0013] In order to obtain a high luminous efficiency, The 10th International Workshop on I norganic and Organic Electroluminescence (EL '00, Hamamatsu) in, Ikai, etc. uses a hole transporting compound as the host of the phosphorescent compound . Further, ME To mpson such as hosts for phosphorescent compounds various electron transporting materials, Ru les, doped with a new I Rijiumu complex thereto.

[0014] The ortho-metalated complex having a central metal was platinum instead of iridium have also been noted. Regarding this type of complex, examples which gave characterized ligands are many known /, Ru! (E.g., Patent Documents;! ~ 5 and Non-Patent Document 1 see.).

[0015] V, although luminance and luminous efficiency when the case of deviation form a light emitting element is intended to be significantly improved compared to conventional devices since the light that light emission derived from phosphorescence, element the emission lifetime is a problem that less than conventional elements point. Thus, material of high efficiency phosphorescent property, the performance improvement of the light emission life of the short-waved and elements of the emission wavelength can withstand the difficulty instrument practical use can be sufficiently achieved! /, It! /, The is in the present circumstances.

[0016] Also with respect to the shorter and shorter wavelengths, to date fluorine atom phenylalanine pyridine, Torifuruoro methyl group, introducing an electron withdrawing group such as Shiano group as a substituent, the Piccoli phosphate Ya Birazaboru system as a ligand it is known to introduce a ligand (e.g., Patent documents 6 to; 10 and non-Patent Document;!. ~ 4 see) is, these ligands with emission wavelength shorter of luminescent materials the blue to achieve, while the elements of high efficiency can be achieved, for light emission lifetime of the device to be significantly degraded, improvement of the trade-off has been required.

[0017] metal complex having a phenylene Rubirazoru substituted with phenylene Le group is known as a ligand (e.g., Patent Documents 11, 12 references.). However, there remains room for improvement from the viewpoint of luminous efficiency without here the force yet sufficient seen improvements in light emission of the element life in substitution pattern of the phenyl group to Hue two Rupira tetrazole disclosed. On the other hand, a ligand having a steric hindrance of the location substituent is obtained findings that good improvement of the emission luminance, is also seen examples applied to phenylene Honoré pyrazole mother nucleus (e.g., Patent Documents 13 references.).

[0018] The phenylene imidazoles in the basic skeleton as a ligand, there remains room for improvement not seen significant improvements to the force S, the emission lifetime of example the introduction of various substituents is disclosed (e.g., Patent documents 15, 16 references.).

Further, carbazole as a ligand, dibenzofuran, example of using a compound having a heterocyclic skeleton of tricyclic condensed ring of 6 5 6 type such as dibenzo Chio Fen is disclosed (for example, Patent Document 1, 11 , 17, 18 references.) is the emission lifetime, in terms of both the luminous efficiency is not sufficient, and further improvement has been desired.

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: International Publication No. WO 02/15645 path

Patent Document 7:: JP 2003- 123982 JP

Patent Document 8:: JP 2002- 117978 JP

Patent Document 9: JP 2003- 146996 JP

Patent Document 10: International Publication No. 04/016711 pamphlet

Patent Document 11: International Publication No. 04/085450 pamphlet

Patent Document 12: JP 2005- 53912 JP

Patent Document 13: JP 2003- 109758 JP

Patent Document 14: JP 2001- 247859 JP

Patent Document 15: International Publication No. 05/007767 pamphlet

Patent Document 16: JP 2005- 68110 JP

Patent Document 17: JP 2005- 23070 JP

Patent Document 18: JP 2005- 23071 JP

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

Non-Patent Document 2: Aplied Physics Letters, Vol. 79, pp. 2082 (2001) Non-Patent Document 3: Aplied Physics Letters, No. 83, pp. 3818 (2003) Non-Patent Document 4: New Journal of Chemistry, 26 winding, 1171, pp. (2002) dISCLOSURE oF tHE iNVENTION

Problems that the Invention is to you'll solve

[0020] are those the invention has been made in view of the problems of the object of the present invention, the emission wavelength is controlled, showed high luminous efficiency, and organic EL with long organic EL device material emission lifetime element is to provide an illuminating device and a display device.

Means for Solving the Problems

[0021] The above problems could be solved by the following constitution.

[0022] 1. Organic elect port Rumi Nessensu element material which is a metal complex represented by the following general formula (la).

[0023] [Formula 1]

[0024] [In the general formula (la), C and N are a covalent or coordinate bond to the metal atom M

1

. A is a cyclic group bonded to the metal atom M via a carbon atom, B is via a nitrogen atom

1

Te represents a cyclic group bonded to a metal atom M.

1

[0025] Further, in the general formula (la), or a cyclic group represented by A is a group represented by the following general formula (lb), or the following general formula on a metal complex represented by the general formula (la) having (lb) Deara it is the group as a substituent.

[0026] [Formula 2]. General formula

[0027] In the general formula (lb), X represents 〇, S, N- R 2 (R 2 is an alkyl group,. Representing the Ariru group or to Teroari Ichiru group) a.

[0028] Z, Z, Z, a nitrogen atom or CR = (R is a hydrogen atom or a substituent Z is independently Table

1 2 3 4 4 4

It is. ) Represents, one of Z, Z, Z, Z is a nitrogen atom. X -L -X the distribution of 2 seats

1 2 3 4 1 1 2

Represents ligand, X, X each independently represents a carbon atom, a nitrogen atom or an oxygen atom. L is

1 2 1

X, represents an atomic group to form a bidentate ligand with X. Table integer of 1, 2 or 3 ml may

1 2

And, m2 is 0, 1 or force ml + m @ 2 represents an integer of 2 is 2 or 3. Ru Ah with a metal atom M is a group 8-10 metal in the periodic table. ]

1

2. Organic elect port luminescent device material according to the 1, wherein the general formula (la) is characterized by being represented by the following general formula (1).

[0029] [Formula 3] Formula (1)

[Wherein, R represents an alkyl group, Ariru group, Heteroariru group. Y, Y is a nitrogen atom

1 1 2

Or CR = (R is a hydrogen atom or a substituent group). X, L, X, ml, m2, M is

3 3 1 1 2 1 wherein X in the general formula (la), L, X, is synonymous with ml, m2, M. ] 3. The organic elect port luminescent device material according to the 2 general formula (1) is characterized by being represented by the following general formula (2).

[0031] [Formula 4] General formula (2)

[0032] [XLX wherein, XLX ml m2 MRYY the above general formula in (1)

1 1 2 1 1 1 2 1 1 synonymous with 2 ml m2 MRYY. The X Ζ Ζ Ζ Ζ you in the general formula (lb)

1 1 1 2 1 2 3 4

Kick is synonymous with each XZZZZ. ]

1 2 3 4

4. Formula (1) or the general formula (2), YY gar CR = CR = (RR

1 2 4 5 4 5 represents a hydrogen atom or a substituent. Organic elect port luminescent device material according to the 2 or 3, characterized in that) it is.

[0033] 5. the general formula (1) or the general formula (2), it R is a methyl group, Ariru group

1

Organic elect port luminescent device material according to any one of the 2 4, characterized in

[0034] In 6. Formula (1) or general formula (2), Ari having a substituent R 2, 6-position

1

Organic elect port Rumine' sensing device material according to any one of the 2 5, characterized in that the Le group.

[0035] 7. Formula (1) or the general formula (2), and wherein M is Ir or Pt

1

Any force of the 2 6, organic elect port luminescent device material according to item 1.

[0036] 8. Formula (1) or the general formula (2), any force of the 2-7, wherein m2 is 0, organic elect port luminescent device material according to item 1.

[0037] 9. Any force of the 1-8, organic elect port luminescent element characterized by containing the light-emitting layer of organic-elect opening luminescent device material according to item 1.

[0038] 10. Viewing apparatus characterized by having an organic-elect opening device as described in the 9.

[0039] 11. lighting apparatus characterized by having an organic-elect opening device as described in the 9.

Effect of the invention

[0040] The present invention, useful organic EL element material for the organic EL element is obtained, the emission wavelength is controlled by using the organic EL element material, it shows high luminous efficiency and long emission life the organic EL element, it is possible to provide a lighting device and a display device.

BRIEF DESCRIPTION OF THE DRAWINGS

[0041] 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.

3 is a schematic diagram of a pixel.

4 is a schematic view of a passive matrix full-color displays.

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

It is a schematic diagram of FIG. 6 lighting device.

DESCRIPTION OF SYMBOLS

[0042] 1 display

3 pixels

5 scanning lines

6 data lines

7 power line

10 organic EL element

12 drive transistor

13 capacitor A display unit

B control unit

102 glass cover

105 cathode

106 organic EL layer

107 transparent electrode-attached glass substrate

108 nitrogen gas

109 Tomizuzai

BEST MODE FOR CARRYING OUT THE INVENTION

[0043] Hereinafter, details of each component according to the present invention will be sequentially described.

[0044] For the metal complex is an organic EL device material of the present invention will be described.

[0045] First, the metal complex represented by the general formula (la) will be described.

[0046] In the general formula (la), C, N forms a covalent or coordinate bonds with the metal atom M.

1

[0047] A is a cyclic group bonded to the metal atom M via a carbon atom.

1

[0048] The cyclic group represented by A, preferably a 5-membered or 6-membered ring, more preferably below following general formula A - is a ring structure represented by ;! ~ A- 53.

[0049] (* are shows where to form a bond with a metal atom M! /, Ru).

1

[0050] [of 5]

Blasphemy []]

*

[0052] The general formula A - in ;! ~ A- 53, RA

1, RA

2, RA

3, RA independently represents a hydrogen atom or a substituent 4

A representative.

[0053] Alkyl groups as examples of the substituent (e.g., methyl group, Echiru group, a propyl group, isopropoxy port propyl group, tert-butyl group, a pentyl group, a hexyl group, Okuchiru group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), a cycloalkyl group (e.g., cyclopentyl pentyl group, cyclohexyl group, etc.), an alkenyl group (e.g., Bulle group, Ariru group), § Rukieru group (e.g., Echuru group, propargyl group or the like ), an aromatic hydrocarbon Hajime Tamaki (an aromatic carbocyclic group, also referred to as Ariru group, e.g., phenyl group, p black port Hue group, mesityl group, a tolyl group, a xylyl group, a naphthyl group, an anthryl group, Azureniru group, Asenafute two Honoré group, Furuoreniru group, Fuenantoriru group, Indeyuru group, pyrenyl group, Bifueyurinore group), an aromatic Hajime Tamaki (eg If, pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, imidazolyl group, benzimidazolyl group, a pyrazolyl group, Pirajuru group, Toriazoriru group (eg seismic ίί, 1, 2, 4 Bokuri zone 'single Honoré 1 Inore group, 1, 2, 3 Bokuri zone 'single Honoré 1 Inore group), Okisazoriru group, benzo O hexa benzotriazolyl group, a thiazolyl group, Isookisazoriru group, Isochia group, furazanyl group, thienyl group, quinolyl group, a benzofuryl group, dibenzofuryl group, those Benzoche group, dibenzo Choi group, an indolyl group, Kanoreno Zorinore group, Karuborini group, one carbon atom constituting the carboline ring di § the carbazolyl group (wherein carbolinyl group is replaced by a nitrogen atom shown), a quinoxalinyl group, a pyridazinyl group, a triazinyl group, a quinazolinyl group, Futarajuru group , A Hajime Tamaki (e.g., a pyrrolidyl group, Imidazorijinore group, morpholyl group, Okisazorijinore group), an alkoxy group (e.g., main butoxy group, an ethoxy group, Puropiruokishi group, Penchiruokishi group, to Kishiruokishi group, O Kuchiruokishi group, Dodeshiruokishi group ) cycloalkoxy group (e.g., cyclopentyl Okishi group, Kishinoreokishi group cyclohexylene, etc.), Arinoreokishi group (e.g., phenoxy group, Na Fuchiruokishi group), an alkylthio group (e.g., methylthio group, Echiruchio group, propyl thio group, pentylthio group , to cyclohexylthio group, Okuchiruchio group, dodecylthio group, etc.), cycloalkylthio groups (for example, cyclopentylthio group, cyclohexylthio group cyclohexylene, etc.), Ariruchio group (e.g., phenylene group, a heteroarylthio group, naphthylthio group, etc.), alkoxy Carbonylation Norre group (e.g., methylcarbamoyl Honoré oxy Kano repo two Honoré group, E Chino Les oxy Kano repo two Honoré group, Buchinoreoki aryloxycarbonyl group, O-lipped Ruo alkoxycarbonyl group, dodecyl O alkoxycarbonyl group), Ariruokishi carbonyl group (e.g., phenylalanine O alkoxycarbonyl group, Nafuchiruoki aryloxycarbonyl group), a sulfamoyl group (e.g., aminosulfonyl group, methylamino sul Honiru group, dimethylamino sulfonyl group, butyl aminosulfonyl group, to Kishiruaminosu Norehoniru group, a cycloalkyl hexyl aminosulfonyl group, O-lipped Le aminosulfonyl group, dodecyl aminosulfonyl group, phenylpropyl aminosulfonyl group, naphthyl aminosulfonyl group, 2-pyridyl aminosulfonyl group), Ashiru group (e.g., Asechiru group, Echirukarubo two group, flop Pills carbonyl group, pentyl group, hexyl group cycloheteroalkyl, O lipped ylcarbonyl group, 2-Echiru hexyl group, dodecyl group, phenylpropyl group, naphthyl group, pyridyl group, etc.), Ashiru Okishi group ( For example, Asechiruokishi group, E chill carbonyl O alkoxy group, Buchirukarubo two Ruokishi group, O-lipped Luca Lupo sulfonyl O alkoxy group, dodecyl Cal Poni Ruo carboxymethyl group, phenylene Honoré carbonyl O carboxymethyl group), amide groups (e.g., methylcarbonyl § amino group , Echirukarubo Ninoreamino group, dimethyl Cal Poni Rua amino group, propyl carbonyl § amino group, Penchiruka Honoré Boni Honoré amino group, cyclohexyl carbonyl cyclohexylene § amino group, 2-Echiru to Kishirukarubo two Ruamino group, O-lipped Luca Lupo sulfonyl § amino group, de Circa Lupo sulfonyl § amino group, Fuenirukaru Boniruamino group, naphthyl carbonyl § amino group), the force Rubamoiru group (e.g., Aminoka Ruponiru group, methyl § amino group, dimethyl § amino carbonyl group, propylamino group, pentylene Rua amino group , hexyl § amino carbonyl group to cycloalkyl, O-lipped Rua amino carbonyl group, 2-Echiru hexyl § amino carbonyl group, Dodeshiruamino force Noreboniru group, phenylpropyl § amino carbonyl group, naphthyl § amino group, 2-pyridyl § iminocarbonyl group), a ureido group (e.g., methylureido group, Echiruureido group, Bae Nchiruureido group, Kishiruureido group cyclohexylene, Okuchiruureido group, dodecyl ureido group, Fueniruureido group Nafuchiruureido group, 2-pyridyl-amino urethane De group), Surufini Honoré group (e.g., methyl sulfide El group, E chill sulfide El group, butyl sulfide El group, hexyl sulfinyl group cycloheteroalkyl, hexyl sulfone to 2-Echiru sulfinyl group, Dodeshirusuru Fier group, Hue Nils sulfide El group , naphthylsulfide El group, 2-Pirijirusurufi sulfonyl group), an alkylsulfonyl group (e.g., methylsulfonyl group, Echirusuruhoniru group, butylsulfonyl group, Kishirusuruhoniru group cyclohexylene, Kishirusuruho two Honoré group to 2- Echiru, dodecylsulfonyl group, etc.), § reel sulfonyl group or hetero aryl sul Honiru group (e.g., phenylalanine sulfonyl group, naphthylsulfonyl group, 2-Pirijirusuru Honiru group), an amino group (e.g., amino group, Echiruamino group, Jimechinoreamino group , butylamino group , Cyclopentyl Rua amino group, 2-Echiru to Kishiruamino group, Dodeshiruamino group, § two Reno group, Nafuchiruamino group, 2-Pirijiruamino group), a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, etc.), fluorinated hydrocarbons hydrogen group (e.g., Furuoromechiru group, tri Furuoromechiru group, penta full O Roe butyl group, pentafluorophenyl group, etc.), Shiano group, nitro group, hydroxy group, a mercapto group, a silyl group (e.g., trimethylsilyl group, Torii Sopurobirushiriru group, triphenyl silyl group, phenylene Rujechirushiriru group etc.) and the like et be.

[0054] Further, A - in ;! ~ A- 53, RA, RA, RA, and two of RA bound to each other

1 2 3 4

It may form a ring.

[0055] naphthalene as a ring formed by Two binding of RA~RA, Tetorari

14

Include emissions, anthracene, Fuenantoren, quinoline, isoquinoline, Indonore, benzofuran, Baie Nzochi old Fen, Indazonore, benzimidazolyl over Honoré, benzothiadiazolyl zone Honoré, Benzuoki Sasol, Karubazonore, dibenzofuran, dibenzothiophene Chio Fen, the ring structure of benzotriazole It is.

[0056] ring structure represented by the general formula One preferred form of A (lb) can also be mentioned.

[0057] Next One the cyclic group represented by B! /, Te be described.

[0058] B is a cyclic group bonded to the metal atom M via the nitrogen atom.

1

[0059] The cyclic group represented by B, and preferably 5-membered or 6-membered ring, a ring structure and more preferably represented by the following general formula B- 1~B- 27.

[0060] (* are shows where to form a bond with a metal atom M! /, Ru).

1

[0061] [Formula 7]

[0062] B via a nitrogen atom, represent a cyclic group bonded to a metal atom M.

1

[0063] In the Formula B- 1~B- 27, RB, RB, RB, RB is independently a hydrogen atom or a substituent

1 2 3 4

A representative.

[0064] RB, RB, RB, as examples of the substituent represented by RB is, the RA, RA ,: RA ,: RA

1 2 3 4 1 2 3 can be exemplified 4 in the same as the examples of the substituent represented.

[0065] The RB, RB, RB, although two may be bonded to each other to form a ring of the RB. Although as examples of the ring formed by Two binding of RB~ RB are two of RA to RA

4 1 4 may be force s the same as those of the ring formed by bonding.

[0066] Metal complexes of general formula (la) is at substitutable positions of the metal complex of A is represented by the force represented by the general formula (lb) ,, one general formula (la) ring structure represented by the general formula (lb) are those that are substituted.

During [0067] Formula (lb), X is 〇, S, represents a N -R. R represents an alkyl group, Ariru group, a Heteroa aryl group.

[0068] alkyl group, Ariru group represented by R, examples of Heteroariru groups include RA ,: RA, RA, the alkyl group represented by RA, Ariru group, those similar to Heteroariru group

3 4

Leave in Rukoto force S.

[0069] Z, Z, Z, Z independently a nitrogen atom or CR = is the (R is a hydrogen atom or a substituent)

1 2 3 4 3 3

Represents, one of Z, Z, Z, Z is a nitrogen atom.

1 2 3 4

[0070] the same as examples of the substituent RA, RA, RA, represented by RA Examples of the substituent represented by R

3 1 2 3 4

Leave by force s include Oh the like.

[0071] In the general formula (la), X- L-X represents a bidentate ligand, X, X are each carbon independently

1 1 2 1 2

Atom, a nitrogen atom or an oxygen atom.

[0072] L represents an atomic group for forming a ligand bidentate X, with X. 2 represented by X- L -X

1 1 Specific examples of ligands of 2 1 1 bidentate, substituted or unsubstituted phenylene Rubirijin, phenylene Rupira Zonore, phenylene Ruimidazo one Honoré, phenylalanine tri § zone Honoré, phenylene Rutetorazonore, Pirazabo Lumpur , § cetyl acetone, etc. picolinic acid. ml represents 1, 2 or 3 integer, m2 is 0, 1 or force ml + m @ 2 represents an integer of 2 is 2 or 3. Among them, preferred case m2 is 0.

[0073] As the metal represented by M used in the formation of the metal complex is of the general formula (la), the original

1

(Also referred to simply as a transition metal) transition metal element group 8-10 element periodic table even in the force used, iridium, platinum and the like as a preferable transition metal elements.

[0074] (ligand)

Metal complexes according to the present invention, for example, the general formula (la) if it is Explaining ml> m @ 2, the partial structure shown in brackets with ml, or the main distribution a partial structure represented by the tautomer thereof called ligand, it referred to as a subsidiary ligand moiety shown in brackets, or a partial structure represented by the tautomer having m @ 2. In the present invention, as represented by the general formula (la), the metal complex is composed of power by a combination of primary ligand or a tautomer thereof and a subsidiary ligand or its tautomer ,, for m @ 2 = 0, i.e., all of the ligands of the metal complex may be consists only partial structure represented by the primary ligand or a tautomer thereof.

[0075] Furthermore used conventionally known metal complex formation, has the art as so-called ligand known ligands (coordination compounds Tomore, U) as a ligand as needed! / , I even! /,.

[0076] Effect from preferably obtained in view of the described invention, the type of the ligand in the complex, more preferably preferably be comprised of preferably rather 1-2 type instrument is one .

[0077] As the ligand used in the conventional known metal complexes, there are various known ligands, for example, the "Photochemistry and Photophysics of Coordination Compou nds" Springer- Verlag Inc. H. Yersin al 1987 issuing, "organometallic chemistry primary base and applications one" Mohanabosha ligand according to Akio Yamamoto 1982, etc. (e.g., halogen ligands (preferably chlorine ligand), hetero nitrogen-containing ring ligands (e.g., Bibirijiru, full Enanto port phosphate, etc.), Do diketone ligand and the like).

[0078] As a preferred embodiment of the present invention, the metal complex represented by the general formula (la) is the formula

And the like that has a structure represented by (1).

During [0079] Formula (1), R represents an alkyl group, Ariru group, Heteroariru group. Y, Y is nitrogen

1 1 2 atom or CR = (R is a hydrogen atom or a substituent group). A, X, L, X, ml,

3 3 1 1 2 m2, M is A in the general formula (la), X, L, X, ml, m2, M and either synonymous,

1 1 1 2 1 or has the general formula (1) in the on metal complexes general formula represented a group represented by (lb) as a substituent.

[0080] As a preferred embodiment of the present invention, the metal complex represented by the general formula (1) is the formula (

Mentioned to be a structure represented by 2).

[0081] In the general formula (2), 2,2,2,2, and,, ml, m @ 2, M is X in the general formula (1),

1 2 3 4 1 1 2 1

Z, is synonymous with Z, Z, Z, X, L, X, ml, m2, M.

1 2 3 4 1 1 2 1

[0082] In the general formula (1) or general formula (2), Y, Y gar CR =, it is not more preferable is -CR =.

[0083] Formula (1) or the general formula (2), R mosquitoes ethyl group, more preferably be in Ariru group member R

1 1 force S even more preferably 2, is preferably a Ariru group having a substituent at the 6-position.

[0084] Hereinafter, the general formula of the present invention (la), (1) and Specific examples of the metal complex represented by (2), the present invention is not limited thereto.

[0085] [of 8]

[0086] [Formula 9]

[0087] [of 10]

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[0089] [of 12]

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009 ββ 2- j

[STS6

[0199] [of 122]

Four]

[0202] [of 125]

[0203] Hereinafter, synthesis examples of representative compounds.

[0204] "Synthesis of Exemplified Compound 2- 425"

[0205] [of 126]

[0206] <Synthesis of the complex A>

15. 2 g of intermediate 1 to 2-ethoxyethanol 200ml are dissolved in water 75 ml, nitrogen atmosphere under addition of iridium chloride 4. 7 g, it was heated to reflux for 3 hours. The reaction mixture was allowed to cool, and the precipitated solid was collected by filtration, washed with methanol, and dried complex A to give 12. lg.

[0207] The 8 · 4g complex A <Synthesis of Complex B> was dissolved in 2-ethoxyethanol 150 ml, § cetyl acetone 7 ml, sodium carbonate 7. Og mixture was subjected 3 hours heating under reflux under a nitrogen atmosphere. The reaction mixture was allowed to cool, poured into water 300 ml, and the precipitated solid was collected by filtration, washed with water to obtain a complex B. Further refining is not performed, which was used in the next step.

[0208] <Synthesis of Exemplified Compound 2 425>

The synthesized complexes B as described above was dissolved in ethylene glycol 200 ml, Intermediate 1 4. 2 g was added, and stirred for 4 hours while heating at 0.99 ° C under a nitrogen atmosphere. The reaction solution was allowed to cool, water 200ml added and the precipitated solid was collected by filtration and washed with methanol. Furthermore it was dissolved in a small amount of methylene chloride, and purified by silica gel column chromatography to obtain Exemplified Compound 2 425 of interest 7. 7 g.

[0209] "applied to the organic EL element of the organic EL element material"

When fabricating the organic EL device of the present invention using an organic EL device material of the present invention, among the constituent layers of the organic EL element (the details will be described later), an organic EL device of the present invention to a light-emitting layer or an electron blocking layer it is preferable to use a material. Further, preferably used as the light emitting dough dopant as described above in the light-emitting layer.

[0210] (light-emitting host and the light-emitting dopant)

The mixing ratio of the light-emitting dopant to the emission host is a host compound which is a main component of the light-emitting layer is preferably from 0.1 mass; is to regulate the range of less than to 30%!.

[0211] However, the light emitting dopant opponent having different structures Yogu mixing be used by mixing plural kinds of compounds, also a phosphorescent dopant and a fluorescent dopant having other metal complexes or other structures good.

[0212] Herein, an optionally dopants in combination with the metal complex to be used as the light emitting dopant (phosphorescent dopant, a fluorescent dopant, etc.). Emitting dopant roughly, two kinds there phosphorescent dopant which emits fluorescent dopant and phosphorescent which emits fluorescence

[0213] 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 based dyes or rare earth complex based fluorescent material or the like, can be mentioned.

[0214] As a typical example of the latter (phosphorescent dopant), preferably Group 8 in the periodic table, Group 9, a complex compound containing a 1 0 group transition metal elements, more preferably an iridium compound , osmium compound, is among the most preferred are iridium compound.

[0215] Specifically, a compound described in the following patent publications.

[0216] WO 00/70655 pamphlet, JP 2002- 280178, JP 2001 -18 dish 6, JP 2002- 280179, JP 2001- 18 plates 7, 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 pamphlet column K JP 2002- 332291, JP 2002- 50484, JP 2002- 33 2292, JP 2002- 83684, JP-Kohyo 2002 - 540 572, 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.

[0217] The following illustrates a portion of a specific example.

[0218] [Formula 127] Pt ~ 1 Pt ~ 2

28]

[0221] (light-emitting host)

The host compound used in the present invention, phosphorescence quantum yield of the phosphorescence emission at room temperature (2 5 ° C) among the compounds contained in the light emitting layer refers to compounds of less than 0.01.

It not particularly limited in structure as the light emitting host employed in [0222] the present invention, typically the force carbazole derivatives, triaryl § amine derivatives, aromatic borane derivatives, nitrogen-containing heterocyclic compounds, Chiofen derivative , furan derivatives, those having a basic bone skeleton of such Origoariren compound, or carboline derivatives Ya ring structure in which at least one of carbon atoms of the hydrocarbon ring to configure a carboline ring of the carboline derivative is substituted by a nitrogen atom derivative having the granulation and the like. Among them, the force carbazole derivatives, least one even carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives Ya the carboline derivatives is replaced with a nitrogen atom! /, Ru derivatives having a cyclic structure is preferably used.

[0223] Hereinafter, specific examples force present invention is not limited thereto. These compounds also preferably used as a hole-blocking material.

[0224] [of 130]

[0225] [of 131] H10

32]

[0227] [Formula 133] 隨 H24

In the light-emitting layer according to [0228] the present invention may be used in plural kinds in combination known host compound as a host compound. By using a plurality of host compounds, it is possible to control the transfer of charges can be highly efficient organic EL element. These known host of compounds having a positive hole transporting ability and an electron transporting ability, and prevents the longer wavelength of emission, noted and high Tg preferred compounds are (glass transition temperature)! / ,.

[0229] The light emitting host used in the present invention is also a low molecular weight compound, low-molecular compound having a polymerizable group such as Yogu Bulle group or epoxy group with a high molecular compound having a repeating unit (deposition polymerizable light-emitting host) Demore, Les,. [0230] The light-emitting host, a hole transporting ability and an electron transporting ability, and prevents the longer wavelength of emission, noted and high Tg preferred compounds are (glass transition temperature)! /,.

[0231] Specific examples of the light emitting host, compounds described in the following references are preferred.

For example, JP 2001- 257076, JP 2002- 308855, JP 2001- 313179, JP 2002- 319491, JP 2001- 357977, JP-open 2002- 334786, JP- JP 2002- 8860, JP 2002- 334787 Patent Gazette, JP 2002- 15871, JP 2002- 334788, JP 2002- 4305 6, JP 2002- 334789, JP- JP 2002- 75645, JP 2002- 338579, JP 2002- 105445, JP 2002- 343568, JP-open 2002- 141173, JP 2002- 352957, JP 2002- 203683, JP 2002- 363227, JP 2002- 231453, JP 2003- 3 165, JP 2002- 234888, JP 2003- 27048, JP 200 2-two hundred fifty-five thousand nine hundred thirty-four, JP 2002- 260861, JP 2002- 280183, JP 2002- 299060, JP 2002- 302516, JP 2002- 305083 JP , JP 2002- 305084, JP 2002- 308837 Patent Publication.

[0232] The light emitting layer may contain a host compound further having a fluorescence maximum wavelength as a host compound. In this case, energy transfer from other host compound and a phosphorescent compound to a fluorescent compound, an electroluminescent as an organic EL element is also obtained emission from other host compound having a fluorescence maximum wavelength. Ino preferred as a host compound having a fluorescence maximum wavelength is a high fluorescent quantum yield in a solution state. Here, the fluorescence quantum yield of 10% or more, particularly 30% or more is preferable. Is a host compound having a specific fluorescence maximum wavelength, coumarin dyes, pyran based dyes, Shianin dyes, Kurokoniumu dyes, Sukuari © beam based dyes, O Kiso Benz anthracene dyes, Furuoresein dyes, rhodamine dyes , pyrylium based dyes, perylene dyes, stilbene dyes, Porichiofen based dyes, and the like. Fluorescence quantum yield, the fourth edition 362 pp Bunko II Jikken Kagaku Koza 7 (1 992 2011 Edition, Maruzen) can be measured by the method described in.

[0233] Next, there will be described a configuration of a typical organic EL device.

[0234] "layers constituting the organic EL device" for the layers constituting the organic EL device of the present invention will be described.

[0235] Preferred examples of the layer structure of the organic EL device of the present invention are shown below, but the invention is not limited to these.

[0236] (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 transporting layer / negative electrode

(Iv) anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transporting layer / negative electrode

(V) anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transporting layer / negative electrode buffer layer / 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 layer / 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.

[0237] In the present invention, a hole blocking layer, an organic EL device material of the present invention that force S preferably have use in electron blocking layer or the like, particularly preferably be used for the hole blocking layer.

[0238] The hole blocking layer and the organic EL device material of the present invention, when to be contained in the electron blocking layer, any force of Claims paragraph 1 - paragraph 7, the organic EL of the present invention described in item 1 the device material, may be contained in a state of 100% by mass as a layer constituent, such as a hole blocking layer or an electron blocking layer, it may be mixed with other organic compounds.

[0239] The thickness of the blocking layer according to the present invention is preferably from 3 to 100 nm, more preferably 5 to 30 nm.

[0240] "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.

[0241] As the hole blocking layer, for example, JP-A 11 204 258 discloses, 11 204 359 JP Gazette, and "Organic EL Elements and Industrialization Front thereof (Nov. 30, 1998 E j 'tea' es Inc. issue) hole blocking according to page 237, etc. "(the hole blocking) layer and the like are applicable as the hole blocking layer according to the present invention. It can also be used as a hole blocking layer as required configuration of an electron transport layer described later, according to the present invention.

[0242] The organic EL device of the present invention has a hole blocking layer as a constituent layer, at least one carbon atom of a hydrocarbon ring the hole blocking layer constituting a carboline ring of the force Ruporin derivative or the carboline derivatives One Although it is preferred to have contains a derivative having a cyclic structure being replaced with a nitrogen atom.

[0243] "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.

In [0244] The present invention, there use adjacent layer adjacent to the light-emitting layer, i.e. a hole blocking layer, the above-mentioned organic EL element preferably be a material instrument particularly electron blocking layer of the present invention to electron blocking layer it is preferable.

[0245] "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. Hole transport layer leaves in this and force S provided as a single layer or plural layers.

[0246] As the hole transporting material, particularly limited Nag conventional, and those which are conventionally used as the charge injection transport material of the hole in Hikarishirubeden material, a hole injection layer of the organic EL device, used in a hole transporting layer It forces those known in the art to be can be used to select an arbitrary one.

[0247] The hole transporting material is a hole injection or transport, which has any of the electron barrier property

, Organic matter, may be any of inorganic materials. For example, Toriazoru derivatives, Okisajia tetrazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylene Renjiamin derivatives, Ariruamin derivatives, Amino-substituted chalcone derivatives, Okisazoru derivatives, styryl anthracene derivatives, Furuorenon derivative conductor, hydrazone derivatives, stilbene derivatives, silazane derivatives, Anirin copolymer, also conductive polymer oligomer and especially Chio Fen oligomer.

[0248] Power porphyrin compounds which can be used those described above as the hole transporting material, an aromatic tertiary Amin compounds and styrylamine compounds, it is particularly preferable to use an aromatic tertiary Amin of compounds.

[0249] Aromatic Representative examples of the tertiary Amin compounds and Suchiriruamin compound, N, N, N ', N' - tetramethyl Hue Nino array 4, A 'Jiaminofue two Honoré; N, N' - Jifueninore N, N , - bis (3 Mechirufue sulfonyl) one [1, 1 '- Bifue sulfonyl] one 4, 4' - Jiamin (TPD); 2, 2 - bis (4-di-one p-tolyl § Minofu enyl) propane; 1, 1,1-bis (4-di-one p Torirua Minofue two Honoré) cyclohexane; N, N, N ', N' - tetramethyl one p Torinore one 4, A '- diamine Nobifueniru; 1, 1- bis (4-di one p-tolyl § Minofu enyl) key Sun to 4 Fuenirushikuro; bis (4 - Jimechiruamino one 2 Mechirufue two Honoré) phenylmethane, bis (4-di one p- Toriruaminofue two Honoré) phenylmethane; N, N '- Jifue two Norre one N, N '- di (4-methoxy phenylene Honoré) one 4, 4' - Jiaminobifue two Honoré; N, N, N ', N' - Tetorafue two Norre one 4, 4 'over-diamino diphenyl ether Honoré; 4, A' bis (Jifueniruamino) quad riff enyl; N, N, N-tri (p- tolyl) Amin ; 4- (di -p- Toriruamino) over one [4- (di -p preparative Riruamino) styryl] stilbene; 4-N, N-diphenyl-amino chromatography (2 Jifue two ruby ​​two Honoré) benzene; 3-methoxy-4 ' N, N-diphenyl-amino stilbene; N-phenylene carbazole, even those with the US Patent No. 5, 061, 569 Pat intramolecular two fused aromatic rings disclosed in, for example, 4 , 4 'bis [N-(1-naphthyl) N Fueniruamino] biphenyl (NPD), triphenyl § Minh units that are described in JP-a-4 308 688 is coupled to three starburst 4, 4', 4 '- tris [N- (3- methylphenyl) N Fuenirua Roh] triphenyl § Min (MTDATA) and the like.

[0250] Furthermore it is also possible to use these materials are introduced in a polymer chain or a polymer having the material as the polymer main chain. Further, it is possible to p-type Si, inorganic compounds such as p-type SiC using a hole injection material, a hole transport material.

[0251] The hole transport layer is 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. No particular limitation is imposed on the thickness of the hole transporting layer, but usually about 5 to 5000 nm. The hole transport layer may have a single layer structure made of one or two or more of the above materials.

[0252] "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 leaves at Rukoto force S is provided a single-layer or multiple layers.

[0253] Conventionally, an electron-transporting layer of a single layer, and if a plurality of layers as an electron transporting material for the electron transport layer in contact next to the cathode side of the light-emitting layer (also serving as a hole blocking material), lower the serial of the materials are known.

[0254] Further, the electron transporting layer be used optionally selected from conventionally known compounds the electrons injected from the cathode as Yogu the material if which have a function of transmitting the light emitting layer leave with a force S.

[0255] 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, Karupojiimido, substituted with Fureoreniride Nmetan derivatives, anthraquinodimethane and anthrone derivatives, Okisajiazoru derivative, carboline derivative or at least one nitrogen atom of the carbon atoms of a hydrocarbon ring constituting a carboline ring of the carboline derivatives, derivatives having to have cyclic structures. Further in the above Okisajiazoru derivatives, may be used an oxygen atom Okisajiazoru ring thiadiazole derivative substituted by a sulfur atom, a quinoxaline derivative also electron-transporting material having a known! /, Ru quinoxaline ring as electron-withdrawing group.

[0256] Furthermore it is also possible to use these materials are introduced in a polymer chain or a polymer having the material as the polymer main chain.

[0257] The metal complexes of 8-hydroxyquinoline derivatives, such as tris (8-hydroxyquinoline) Arumiyuu beam (Alq), tris (5, 7-dichloro-one 8-quinolinol) aluminum, tris (5, 7-jib port mode 8-hydroxyquinoline) aluminum, tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc., and the central metal of these metal complexes is an in, Mg, Cu, Ca, Sn, location-out Ga or Pb may also be used as the electron transporting material. Other, it can be preferably used as the electron transport material also those metal-free or metal phthalocyanine, or their termini, which is substituted by an alkyl group Ya sulfonic acid group. Further, distyryl Vila derivative exemplified as a material for the light emitting layer may preferably be used as the electron transporting material, a hole injection layer, a hole transport layer as well as n-type Si, also an inorganic semiconductor such as n-type SiC it can be used as the electron transporting material.

[0258] The electron transport layer is the electron transport material, for example, vacuum deposition, spin coating, 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 made of one or two or more of the above materials.

[0259] Next, a description will be given injecting layer used as a constituent layer of the organic EL device of the present invention.

[0260] "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, is present between the as an anode between the light-emitting layer or a hole transport layer, and a cathode and a light emitting layer or an electron transport layer it may be.

[0261] An injection layer is a layer which is arranged between an electrode and an organic layer to decrease an operating voltage and emission brightness enhancement, "Organic EL element and its Industrialization Front (November 30, 1998 E j 'tee' E, Inc. published) "2 Chapter 2 of" electrode material "(which is described in detail in pages 123 to 166), a hole injection layer (anode buffer more) and an electron injection layer (more cathode buffer) there is.

[0262] anode buffer more (hole injection layer) Hei 9- 45479 discloses, 9 260 062 JP Gazette describes a also detailed in the 8-288069 discloses such, as a specific example, copper more phthalocyanine buffer typified lid port Shianin, more oxides buffer typified by vanadium oxide, amorphous carbon buffer further, Poria diphosphate (Emerarudin) and Porichiofen conductive polymer polymer buffer one layer using such the like and the like.

[0263] cathode buffer more (electron injection layer) Hei 6- 325871 discloses, 9 17574 JP Gazette describes a also detailed in the 10-74586 discloses such, specifically Sutoronchi © more metal buffer typified beam Ya aluminum, § alkali metal compound buffer further represented by lithium fluoride, alkaline earth typified by magnesium fluoride metal compound buffer further, oxide buffer typified by aluminum oxide one layer or the like can be mentioned, et al are.

[0264] The buffer further (injection layer) is very depending on the thin film and it is desirable tool material thickness thereof 0;.! In the range of ~ LOOnm preferred.

[0265] The injection layer materials described above, for example, vacuum deposition, spin coating, casting, ink jet method, by a known method LB method, can be formed by thinning. No particular limitation is imposed on the thickness of the injection layer, but usually is about 5 to 5000 nm. Injection layer This may be a single layer structure comprised of one or more kinds of the above materials.

[0266] "anode"

The anode of the organic EL device of the present invention, a large work function (4 eV or more) metals, an alloy, is preferably used a conductive compound and a mixture thereof as an electrode material. Specific examples of such an electrode material, metals such as Au, Cul, indium tin O Kishido (ITO), SnO, include a conductive transparent material such as ZnO are. Further, IDIXO - may be a material capable of producing a transparent conductive film (In O ZnO) spruce amorphous. Anode to form a thin film by a method such as vapor deposition or sputtering of the electrode material, if not desired shape Yogu or pattern accuracy by forming a pattern with less required by photolithography (100 degrees or more m ), a pattern may be formed through a mask of a desired form at the time of depositing or spattering of the electrode material. When light is emitted through the anode, the sheet resistance of the transmittance as an anode was Sigma desirable to greater than 10% preferably less several hundred Omega / mouth. Further, although the layer thickness depends on the material normally. 10 to; 1000 nm, it is preferably selected in the range of 10 to 200 nm. [0267] "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 earth metals. 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, lithium / aluminum mixture, and aluminum. Cathode by vapor deposition, sputtering or some other method of these electrodes material, may this a force S which prepared by forming a thin film. The sheet resistance is preferably several hundred Omega / mouth following instrument thickness of the cathode is usually. 10 to; 1000 nm, is preferably selected in the range of 50 to 200 nm. Herein, to transmit emission, either the anode or the cathode of the organic EL element, emission luminance is advantageous improved if transparent or translucent.

[0268] "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, the glass is not particularly limited as long particularly limited Nag also be of transparent type of plastic, is a preferred substrate for use, for example, glass, quartz, it may be mentioned transparent resin film. Particularly good preferable substrate is resin film Der capable of providing flexibility to the organic EL device

[0269] As the resin film, for example, polyethylene terephthalate (PET), polyethylene Na phthalate (PEN), polyether sulfone (PES), polyetherimide, Porietenore ether ketone, Porifue two Rensurufuido, polyarylate, polyimide, polycarbonate (PC ), cellulose triacetate (TAC), a film and the like made of cellulose acetate propionate (CAP) and the like. [0270] the surface of the resin film, Yogu water vapor permeability even hybrid coating of inorganic or organic coating or both has not been formed is 0. 01g / (m 2 '24h'MPa ) following high it is preferably a barrier film.

[0271] external extraction efficiency of light emission at room temperature of the organic EL device of the present invention is preferably from preferably has a This 1% or more member is 2% or more. Here, the external extraction quantum efficiency (%) = number of electrons XI 00 was flowed in the number of photons / organic EL device emitting organic EL device the outside.

[0272] Furthermore, it is possible to use a hue improving filter Chief of the color filter first class.

[0273] 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.).

[0274] When used as a multicolor display apparatus is comprised of an organic EL device that have a least two different emission maximum wavelength, illustrating a preferred example of manufacturing an organic EL element.

[0275] "method for manufacturing the organic EL device"

As an example of a method for manufacturing an organic EL device of the present invention, an anode / hole injection layer / hole transport layer / luminescent layer / hole blocking layer / manufacturing method of the electron-transporting layer / cathode buffer layer / cathode force becomes organic EL device Nitsu! /, Te will be explained.

[0276] First suitable substrate desired electrode material on, for example, a thin film made of an anode substance, 1 mu m or less, preferably are shorted with a method such as vapor deposition or sputtering to have a thickness of 10~200nm It is formed, to prepare an anode. Next, a hole injection layer, which is a device material on the hole transporting layer, light emitting layer, a hole blocking layer to form a thin film containing an organic compound such as an electron transport layer

[0277] As a method for thinning the thin film containing the organic compound, a spin coating method, a casting method, an ink jet method, evaporation method, a printing method, a homogeneous film is obtained Ya immediately and pinholes from the viewpoint of production difficult, etc., vacuum deposition or spin coating is not particularly preferred. Further it may apply different film method per layer. When employing the vapor deposition film, the deposition conditions of that varies depending on the kinds of materials used, generally boat temperature 50 to 450 ° C, vacuum degree of 10- 6~10- 2Pa, deposition rate 0. 0;! ~ 50nm / sec, a substrate temperature over 5 0 to 300 ° C, it is desirable to select appropriate thickness in the range of 0. 1 to 5 m.

[0278] After formation of these layers, a thin film made of a cathode material is formed thereon to a film thickness of preferably in the range from 50 to 200 nm or less 1 mu m, for example, it is formed by a method such as vapor deposition or sputtering , the desired organic EL device can be obtained by providing the cathode. The production of organic EL device may be subjected once of preferred to prepare from a consistently positive hole injection layer by vacuum to the cathode bur, a film method differs removed prematurely. At that time, the required to be carried out under a dry inert gas atmosphere.

[0279] "display device"

Described display device of the present invention. Display device of the present invention having the above organic EL element.

[0280] Display device of the present invention may be a multi-colored in a single color, here, describes a multicolor display device. For multicolor display device provided with a shadow mask only at the time of the light emitting layer formation, vapor fusing method, a casting method on one surface, a spin coating method, an inkjet method, the film can be formed by a printing method or the like.

[0281] When performing putter Jung only the light emitting layer is not limited to this method, it is preferably an evaporation method, an inkjet method, a printing method. In the case of using an evaporation method is Shi preferred putter Jung using a shadow mask.

[0282] 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.

[0283] When a DC voltage is applied to such multi-color display device obtained in the anode to +, cathode can be observed emission and applying a voltage of about 2~40V as one polarity. Also, no at all emission without current flows even if a voltage is applied in reverse polarity. Furthermore, when an AC voltage is applied, the anode +, cathode - emits light only in a state. It should be noted that the waveform of the AC to be applied by any! /,.

[0284] multicolor display device display devices, displays, Ru can be used as various light emission sources. The display device or the display, blue, red, three organic EL elements V use of green light emission, it is possible to display a full-color by Rukoto.

[0285] Display devices, as a display, a television, a personal computer, a thermopile devices, AV equipment, character broadcast display and an information display used in a car. May be used as a display device, in particular for reproducing still images and moving images, Dochi any active matrix method in a simple matrix (passive matrix) method driving the dynamic system when used as a display device for video playback Radea good.

[0286] 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 it! / ... limited thereto

[0287] "lighting device"

It illustrates lighting device of the present invention. Lighting apparatus of the present invention having the above organic EL element.

[0288] The intended use of the organic EL element having a resonator structure such as Yoguko be used in an organic EL element as the organic EL element having a resonator structure of the present invention, the optical storage medium source, an electrophotographic copying machine of the light source for an optical communication device of the light source, 1S source for a photo-sensor, but are not limited thereto. It may also be used in the applications by the laser oscillation.

[0289] Further, 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 directly visually recognize the still images and moving images it may be used as the type of the display device (display) for. Drive system when used as a display device for reproducing a moving image, a simple matrix may either be an active matrix method even (passive matrix) method. Or, this onset Ming organic EL elements having different emission colors by using two or more, it is possible to produce a full color display device.

[0290] 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

[0291] 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.

[0292] Display 1 and a display unit A, the control unit B or the like for images scanned in the display portion A on the basis of the image information having a plurality of pixels.

[0293] The control unit B is electrically connected to the display section A, transmits a scanning signal and an image data signal based on image information from the outside to each of the plurality of pixels, the image data pixels of each scan line by the scan signal sequentially emit light in accordance with signals by performing the image scanning in the display section a image information

Ik small ^ Ru.

[0294] FIG. 2 is a schematic drawing of a display section A.

[0295] Display unit A on the substrate, the wiring portion and a plurality of pixels including a plurality of scanning lines 5 and the data lines 6

And a 3, and the like. Given below a description of the main members of the display portion A.

In [0296] Figure shows a case where light emission of the pixels 3 is taken out in the direction of an arrow.

[0297] consists of each conductive material scanning lines 5 and plural data lines 6 of the wiring section, 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).

[0298] pixel 3 when the scanning signal is applied from the scanning lines 5, receive the data signal from the data lines 6, and emit light corresponding to received image data. Pixel color emitting red region, pixels in the green region, side by side on suitable same substrate pixel of blue region, full-color display is possible.

[0299] Next, an emission process of pixels will be explained.

[0300] FIG. 3 is a schematic diagram of a pixel.

[0301] pixel comprises an organic EL element 10, a switching transistor 11, the driving transistor 12, a capacitor 13, and the like. As the organic EL element 10 to a plurality of pixels, red, green, an organic EL element of blue emission, leaving at this and force S perform full-color display by side by side on the same substrate.

[0302] 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 the scanning signal 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 transients It is transmitted to the gate of the static 12.

[0303] 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.

[0304] progressive scanning signal by the scanning of the control unit B is to the next scanning line 5, the driving of the switching transistors 11 are turned off. However, since the drive of the switching transistor 11 is capacitor 13 is also turned off to hold the charged potential of image data signal, driving of the driving transistor 12 is kept turned on, the application of the next scanning signal line emission of the organic EL element 1 0 is continued until cracking. When the next scanning signal by sequential scanning is applied, the driving transistor 12 organic EL element 10 emits light in response to the potential of the next image data signal synchronized with the scanning signal.

[0305] That is, light emission of the organic EL element 10, the organic EL element 10 of each of the plurality of pixels, provided with a switching transistor 11 and driving transistor 12 which is an active element, multiple pixels 3 each organic EL doing light emitting element 10. Such a light-emitting method is called § active matrix method.

[0306] Here, I also emitting a plurality of gradation emission of the organic EL element 10 by the multi-value image data signals having plural gradation potentials! /, Then, the binary image data signal by a predetermined emission amount on, or off. Further, the holding potential of the capacitor 13 it may also be continuously maintained till the next application of the scanning signal les, then, also by! /,. It is discharged immediately before the next scanning signal is applied

[0307] Contact with the present invention! /, Te 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 according to the data signal only when the scan signal is scanned .

[0308] FIG. 4 is a schematic drawing of a display employing a passive matrix method. 4, a plurality of scanning lines 5 and the data lines 6 are provided on opposite sides of the pixel 3 in a lattice pattern.

[0309] sequentially when the scanning signal of the scanning line 5 by the scanning is applied, Les connected to the applied scanning lines 5, Ru pixels 3 emit light in response to image data signals.

[0310] Roh Tsu Shiv reduced active element pixels 3 free ingredients manufacturing costs by matrix method is Hakare

[0311] The organic EL material of the present invention as a lighting device, can be applied to an organic EL element which emits light of substantially white. Obtaining white light emission Ri by the color mixture by simultaneously emitting a plurality of emission colors by a plurality of light-emitting materials. As a combination of the plurality of emission colors, using blue, green, may be one which contains three light-emitting maximum wavelength of the blue of the three primary colors, blue and yellow, the complement color relationship such as blue-green and orange 2 one of or one containing the light-emitting maximum wavelength.

[0312] The combination of the luminescent material for obtaining a plurality of emission colors, a combination a plurality of materials that emit light in a plurality of phosphorescent or fluorescent, and luminescent material that emits light by fluorescence or phosphorescence, from the light-emitting material the light may be combined Mononoi deviation of the dye material emitting the excitation light, but in the white organic EL device according to the present invention, it is a light-emitting dopant only several combinations mixed. Only the formation such as the light emitting layer or hole transporting layer or the electron transport layer is provided a mask pattern Jung, such as a mask, so simply equal simple arrangement separately applying the mask Yogu other layers are common is not necessary, evaporation method, a casting method, a spin coating method, can be formed an ink jet method, a printing method, or the like for example, an electrode film is also improved productivity. According to this method, unlike the white organic EL device arranged in parallel a plurality of colors of light emitting elements in an array, the element itself is a light emitting white.

[0313] As particularly limited luminescent material used for a light-emitting layer Nag example, if the backlight that put the liquid crystal display device, CF (color filter) to match the wavelength range corresponding to the characteristics, according to the present invention metal complexes, also by when whitened combination optionally selected from the known light emitting material! /,.

[0314] one like this way, the white light-emitting organic EL device according to the present invention, the display device, in addition to the Display I, or various light emission sources, a lighting device, home lighting, interior lighting, also exposure light source as the lamp, also backlight of a liquid crystal display device, used in useful to a display device.

[0315] 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

[0316] The present invention will be described by way of examples, but the present invention is not limited thereto.

[0317] Example 1 "Preparation of Organic EL element 1 1"

Substrate and ITO was 150nm deposited on glass as an anode (NH Techno Glass: NA- 45) after the putter Jung, 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. The transparent supporting substrate was fixed to a substrate holder of a vacuum deposition apparatus available on the market, whereas five tantalum resistance heating boat α- NPD, H4, Ir 12, BCP, which enter respectively the Alq, vacuum vapor deposition apparatus (a first It was attached to a vacuum chamber).

[0318] 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.

[0319] 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.;! ~ 0. 2nm / It was deposited to a thickness of the film thickness 20nm transparent supporting substrate, in seconds, a hole injecting / transporting layer.

[0320] In addition, by energizing H4 of containing said heating boat and Ir 12 of entering the boat independently, the deposition rate of a certain Ir- 12 in H4 and the light emitting dopant which is a light-emitting host 100: to be the 6 adjusted to, deposition to a layer thickness of 30 nm, which a light-emitting layer.

[0321] then heated by supplying an electric current to the heating boat containing BCP, deposition rate 0.1; form a hole blocking layer having a thickness of lOnm at ~ 0. 2n m / sec!. Further the heating boat containing Alq was heated to conductible, deposition rate 0.1; an electron transporting layer having a thickness of 20nm at ~ 0.1 2 nm / sec!.

[0322] Next, after transferring elements were deposited to the electron transporting layer to the second vacuum chamber under vacuum, and the outside of the apparatus as stainless steel rectangular perforated mask is placed on the electron transportation layer It was installed in remotely from control.

[0323] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, evaporation Chakusokudo 0. 01-0 by energizing the boat lithium fluoride containing. 02nm / sec to a film thickness 0. 5 nm cathode buffer further the provided and then energized boat charged with § Noreminiumu, with a cathode having a thickness 150nm at a deposition rate of L~2nm / sec, to produce an organic EL element 1-1.

[0324] [of 134] BCP & - ΡΌ

[0325] "organic EL element 1-2 to;! - 37 production of"

In the preparation of the organic EL device 1-1, the light emitting host as described in Table 1, in the same manner except for changing the light-emitting dopant and a hole blocking material, to produce an organic EL device 1 one 2 ;! one ☆ .

[0326] [Table 1]

Emission hole blocking external extraction

Yes Paternoster ε the element ^ - light-emitting Doban Bok 凳允 life light-emitting color «Remarks O, strike« fee quantum efficiency *

1 - Λ H - 4 Ir-lE 100 100 'light blue Comparative Example - 2 H - 4 Comparative Compound 1 8 CP 102: 9S Green Comparative Example

1 -3 H - 4 Comparative Compound 2 BCP 105 93 Teal compare «

1 - AH-4 Comparative Compound 3: BCP 99 blue 緣 compare «

1 - H- 4 Example Compound · 1 - 1 BC P 134 332 Green present invention

1 6 H- 4 illustrate: Compound 1 - 4 BC M6 407 Red present invention

1 - 7 H 4 Exemplified Compound 1. - 6 BC P:? 13 4SS present invention

1-BH- 4 instantiated food 1 -44 BC P 156 411 Net blue present invention:

1 -9 H- exemplified compound 2-69 BCP 149 400 m present invention

1 ~ WH- 4-valent compound 2 -76 BC f 168 689 JunTakara the onset Akira

. 1 -11 H- 4 倒示 of Go compound 2 389 BCP 153 Si7 Kenao present invention ί -12 H - 4 Example Compound 2 '-.? 42S BCP 174 77 Jun elbow invention

\ H - exemplified compound · -? · »■ 559 · BCP 166 702 Net blue present invention -14 H -. 4 example 示化 含物 2 -619 ac ITS 765« blue present invention

1 - H - 4 Example Compound '1 - 1 H - 5 t 9 442 recording the present invention

1 -16 H- 4 Example Compound 1 -4; H - 5 177 4'0 red invention

1 ™ 17 ■ - H - - - 4 - - - Example Compound〗 ~ 8 H - 5 178 503 Net plaster: the onset

1 -18 H - 4 Example Compound 1 · -44 H - 5 5§6 543 Blue present invention:

1 -1 H ~ instantiated base material '2 69 H- ■ 5 158 678 the invention

1 ™ 20 H - 4 Example Compound 2 7δ H - 5 180 747 the invention

1 -21 H- 4. 埦示 compound 2-389 H- 5! 77 720 the present invention

1 -22 H '- 4 illustrate: of base compound · 2 --425 H one S 165 769赫present invention 1 -23 H- 4 Exemplified Compound' 2-559 H - 5 171 677 Hitoshi present transliteration

1 - H- 4 Example Compound 2 -619 ■ H- 5 168 621 * invention

\ 25. H- 6 倒示 Compound 1 -44 BCP 159 490 Blue present 穽明 -26 H - 6 Example Compound · 2-42 SO P 170 799 Net blue present invention

\ -11 H ~ 6 Example Compound 2 -6.19 BC P 567 638 as the present invention

\ - "Z & H- 6 Exemplified Compound 1-44 H - 5 178 531 noodles invention

1 -23 H ~ 6 instantiated 含物: 2.-389 H - 5 161 499 Pure Blue present invention

) -30 H - 6 Example Compound · 2. -4Ζ5 H - 5 ϊ81 758 Ao present invention ... H- 6 Example Compound '2 -6Τ9; H - 5 169 731 ate invention

1 -32 H - 30 1 [Display: Compound 1 -44 I BC Ρ rn 519 invention

1 -33 H -30 ■ Kadaiki 2 -425 BCP 178 800 賨 the present invention

1 -34 H - 3D example shows Compound 2- 6 IS BC P 169 707 the invention

1 one H - 30 剁示 compound〗 - 44 H- 5 165 468 the invention

1 -36 H - 30 Example: Display:!? Compound 2- 5 H - 5 81 90 pure blue present invention

1 ™ 37 H - 30 shows compounds one 6Ί9 JH - 5 167 6S0 present invention 135 Comparative Compound 1

Of the public when the Garden No. 04 / No. 08S4SO 22: page - compound of corresponding to the general formula

[0328] From Table 1, the organic EL element manufactured using the metal complexes according to the present invention, compared with the organic EL device of Comparative Example, pure blue to blue-green short wavelength light emitting high while having a luminous efficiency and emission lifetime it is clear that the life of the can be achieved. In addition, compared with the organic EL device of Comparative Example, it can be seen that blue purity useful as Kogu blue light emitting device.

[0329] Further, by using the preferred embodiment in the metal complexes of the present invention, it is possible to further improve the life of the light emitting element. [0330] Example 2

"Preparation of Organic EL element 2 1"

Using a DC power source to 25mm X 25mm X O. 5mm glass support substrate of, to form an anode of indium tin oxide (ITO, indium / tin = 95/5 molar ratio) Te in the sputtering method (Thickness 200 nm). The surface resistance of the anode was 10 Omega / mouth. A polyethylene Bulle carbazolenevinylene Lumpur (hole transporting binder polymer) / Ir 13 (blue luminescent ortho-metalated complex) / 2 i (4 Bifue two Lil) over 5-(4 t butylphenyl) 1, 3, 4 - Okisajiazo Le (electron transporting material) = 200/2/50 dichloroethane solution of mass ratio was applied with a spin one data one to obtain a light-emitting layer of LOOnm. Butter over the organic compound layer - set up Jung was mask (mask light-emitting area of ​​5 mm X 5 mm), aluminum 150nm was deposited as lithium fluoride 0. 5 nm, and a cathode as more cathode buffer in the deposition apparatus setting the cathode Te digits was produced an organic EL element 2 1 blue emission.

[0331] "Preparation of Organic EL elements 2 2~2- 14"

In the preparation of the organic EL element 2-1, except for changing the light-emitting dopant, as described in Table 2 in the same manner, to produce an organic EL element 2 2~2- 14.

[0332] "Evaluation of Organic EL element"

The resulting organic EL element 2 - In assessing ;! ~ 2-14, a non-emission surface of each organic EL element after fabricated covered with a glass case, the glass substrate having a thickness of 300 m and the sealing substrate using Te, as a sealing material around, epoxy photocuring adhesive (manufactured by Toagosei Co., Ltd. rat task track LC0629B) was applied, which was in close contact with the transparent supporting substrate superimposed on the cathode, a glass substrate by irradiating UV light from cured, sealed, 5, was evaluated by forming the lighting device shown in FIG.

[0333] Then, luminescence was measured luminance and luminous efficiency in the following manner.

[0334] (light emission luminance, luminous efficiency)

Toyo Tekuyuka made source - Sumeja - using Unit 2400, a DC voltage is applied to the organic EL element to emit light, and light emission luminance upon application of a DC voltage of 10V and (cd / m 2) 2. 5m A / luminous efficiency when through a current of cm 2 a (lm / W) were measured. The results obtained are shown in Table 2. The organic EL element 2-1 was represented by a relative value to 100. [0335] [Table 2]

[0336] From Table 2, the organic EL element manufactured using the metal complexes according to the present invention, it is clear that compared, can be achieved a high luminous efficiency and high luminance in an organic EL device in Comparative Example

Example 3

"Preparation of a full-color display device"

(Preparation of blue light emitting element)

Use Les organic EL element 1 12 of Example 1 as a blue light emitting element it was.

[0337] (Preparation of green light emitting element)

Contact! /, In the organic EL device 1 1 of Example 1 Te, except for changing the Ir- 12 to Ir- 1 in the same manner, to prepare a green light-emitting device, was used as a green light-emitting element.

[0338] (Preparation of red light-emitting element)

Contact! /, In the organic EL device 1 1 of Example 1 Te, except for changing the Ir- 12 to Ir- 9 in the same manner, to produce a red light emitting element, was used as red light emitting element.

[0339] Red prepared above, green, juxtaposing a blue emitting organic EL device on the same substrate to fabricate an active matrix type full color display apparatus having a configuration as described in Figure 1. FIG. 2 shows only schematic drawing of a display section A of the display device manufactured. That is, a plurality of pixels 3 (the color of light emission pixels in the red area, the pixels of the green region, pixels etc. blue region) juxtaposed with wiring section containing plural scanning lines 5 and plural data lines 6 on the same board on a has become the wiring portion of the scanning lines 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). Wherein the plurality of pixels 3, the organic EL elements corresponding to the respective emission colors are switches driven active elements receives the image data signal when the scanning signal is applied from the scanning lines 5 from the data line 6, the received It emits light in accordance with image data. Thus red, green, by appropriately juxtaposing blue pixels, to produce a full color display device.

[0340] The by full-color display device to be driven, the luminance has a high ingredients high durability, and sharp full-color moving image display could be obtained.

[0341] Example 4

"Preparation 1 of a white light emitting device and a white lighting device"

Implementing the transparent electrode substrate of the electrode of Example 1 was putter Jung to 20 mm X 20 mm, it is deposited thereon to alpha-NPD in the same manner as the actual Example 1 as a hole injecting / transporting layer with a thickness of 25 nm, further H 4 of the aforesaid heating boat example compound 2-425 containing containing boat and Ir 9 of containing and the boat is energized independently, is HI and the light emitting dopant which is a light-emitting host exemplified compound 2-425 and Ir- deposition rate of 9 100: 5: adjusted to 0.6, was deposited to a thickness of the film thickness 30Ita m, provided with a luminescent layer.

[0342] Then, a hole blocking layer was 10nm deposited BCP. Further, it provided is formed of Alq with 40nm electron-transporting layer.

[0343] Next, a square perforated mask having substantially the same shape as the stainless steel of the transparent electrode was placed on the electron injection layer in the same manner as in Example 1, as lithium fluoride 0. 5 nm, and a cathode as a single layer cathode buffer the aluminum 150nm was deposited film formation.

[0344] The device is provided with a sealing can in a similar manner and similar structure as in Example 1, FIG. 5, to prepare a flat lamp shown in FIG. Almost white light obtained was energized to this plane lamp was found to be used as a lighting device. It was found that light emission of the similarly be replaced by exemplified other compound white is obtained.

[0345] Example 5 "Preparation 2 of white light emitting element and a white illumination device"

After one line of the putter Jung to lOOmmX lOOmm X l. 1mm ITO on a glass substrate as an anode (indium tin O Kishido) substrate was lOOnm film forming the (Nyuita Techno Glass ΝΑ- 45), provided the ITO transparent electrode the transparent supporting substrate was ultra sound waves washed with isopropyl alcohol, dried with dry nitrogen gas and subjected to UV-ozone cleaning for 5 minutes.

[0346] This transparent support substrate, poly (3, 4-ethylenedioxythiophene O carboxymethyl Chio phen) polystyrene sulfonates (PEDOT / PSS ,: Bayer Co., Baytron P A1 4083) solution diluted to 70% with pure water after film formation by spin coating at 3000 rpm, 30 seconds, then dried 1 hour at 200 ° C, provided the first hole transport layer having a thickness of 30 nm.

[0347] The aforesaid substrate was transferred under nitrogen atmosphere, was formed on the first hole transport layer, 1000 rpm a solution of Compound A of 50mg of toluene 10 ml, 30 seconds under the conditions of, by spin coating . Irradiated with 180 seconds by ultraviolet light, after photopolymerization, crosslinking was 1 hour vacuum drying and the second hole transport layer at 60 ° C.

[0348] Next, Compound B (60mg), Ir-14 (3. Omg), 2- 637 (3. Omg) the use of a solution in toluene 6 ml, under the conditions of 1000 rpm, 30 seconds, a spin coating method It was formed by. Irradiated with 15 seconds by ultraviolet light, to perform the photopolymerization, crosslinking, further subjected to 1 hour heating in a vacuum 0.99 ° C, and a light emitting layer.

[0349] In addition, compound C a (20 mg) using a solution in toluene 6 ml, under the conditions of 1000 rpm, 30 seconds, a film was formed by spin coating. Irradiated with 15 seconds by ultraviolet light, to perform the photopolymerization 'bridge, further subjected to 1 hour heating at 80 ° C in vacuo to a hole blocking layer.

[0350] [of 136]

[0351] Subsequently, the substrate was fixed to a substrate holder of a vacuum deposition apparatus, the Alq placed 200mg to molybdenum resistance pressurized heating boat was attached to a vacuum deposition apparatus. After pressure in the vacuum tank was reduced by 4 X 10- 4 Pa or, and heated by supplying an electric current to the boat charged with Alq, it is deposited on the electron transport layer at a deposition rate of 0. lnm / sec, further film an electron transporting layer having a thickness 40 nm.

[0352] Note that the substrate temperature during the deposition was room temperature.

[0353] Subsequently, to form a cathode by depositing lithium fluoride 0. 5 nm and aluminum 11 onm

, To produce a white light-emitting organic EL device.

[0354] almost white light obtained was energized to the device, it has been found that can be used as a lighting device.

Claims

The scope of the claims
Organic elect port Rumine' sensing element material which is a metal complex represented by the following general formula (la).
[Formula 1]
: General formula a)
[In the general formula (la), C and N are a covalent or coordinate bond to the metal atom M
1
. A is a cyclic group bonded to the metal atom M via a carbon atom, B is via a nitrogen atom
1
Te represents a cyclic group bonded to a metal atom M.
1
Further, in the general formula (la), cyclic group represented by the following general formula represented by A Ah with a group represented by (lb) Luke, or the following general on the metal complex represented by the general formula (la) having as a substituent a group represented by the formula (lb).
«Formula f1W In the general formula (lb), X is 〇, S, represents a NR (R represents an alkyl group, Ariru group or to Teroari Ichiru group,.).
Table Z, Z, Z, a nitrogen atom or CR = (R is a hydrogen atom or a substituent Z is independently
1 2 3 4 4 4
It is. ) Represents, one of Z, Z, Z, Z is a nitrogen atom. X -L -X the distribution of 2 seats
1 2 3 4 1 1 2
Represents ligand, X, X each independently represents a carbon atom, a nitrogen atom or an oxygen atom. L represents a group of atoms which form a bidentate ligand with XX. Table integer of 1 2 or 3 ml may
1 2
And, m2 is the force ml + m @ 2 represents an integer of 0 1 or 2 is 2 or 3. Ru Ah with a metal atom M is a group 8-10 metal in the periodic table. ]
1
[2] the general formula (la) is organic elect port luminescent device material according to claim 1, characterized by being represented by the following general formula (1).
[Formula 3] Formula (1)
[Wherein, R represents an alkyl group, Ariru group, Heteroariru group. YY is nitrogen atom
1 1 2
Or CR = (R is a hydrogen atom or a substituent group). AXLX ml m2 M
3 3 1 1 2 1 are as defined AXLX ml m2 M in the general formula (la) force, or one
1 1 2 1
Formula on a metal complex represented by general formula (1) a group represented by (lb) that Yusuke as a substituent. ]
[3] the general formula (1) is an organic elect port luminescent device material according to claim second preceding claims, characterized by being represented by the following general formula (2).
[Formula 4]
The general formula (2)
Wherein, XLX ml m2 MRYY is XLX in formula (1)
1 1 2 1 1 1 2 1 1 synonymous with 2 ml m2 MRYY. The X Ζ Ζ Ζ Ζ you in the general formula (lb)
1 1 1 2 1 2 3 4
Kick is synonymous with each XZZZZ. ]
1 2 3 4
Formula (1) or the general formula (2), YY gar CR = CR = (RR water
It represents a 1 2 4 5 4 5 atom or a substituent. Organic elect port luminescent device material according to paragraph 2 or claim 3, characterized in that) it is.
In Formula (1) or general formula (2), R force S methyl group, that is Ariru group Laid
1
Organic elect port Ruminesse Nsu device material according to any one of claims second to fourth terms of the symptoms.
In the general formula (1) or general formula (2), Ariru group having a substituent R 2, 6-position
1
Any force, organic electronics Toro EL device material according to one of claims second term to fifth paragraphs, characterized in that it.
Formula (1) or the general formula (2), 請 wherein M is Ir or Pt
1
Any force determined in the range the second term to the sixth term, organic elect port luminescent element materials described in (1).
In the general formula (1) or general formula (2), m @ 2 is an organic elect port luminescent device material according to any one of claims range 囲第 binomial - paragraph 7 which is a zero. Any force of Claims paragraph 1 - paragraph 8, organic elect port luminescent element characterized by containing the light-emitting layer of organic-elect opening luminescent device material according to item 1. [10] Display device you characterized by having an organic-elect opening device as according to claim 9.
[11] Lighting device you characterized by having an organic-elect opening device as described in Claim 9.
PCT/JP2007/069822 2006-10-13 2007-10-11 Organic electroluminescent device material, organic electroluminescent device, display and illuminating device WO2008044723A1 (en)

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