TW200936569A - Nitrogen-containing heterocyclic derivative and organic electroluminescent device using the same - Google Patents

Abstract

Disclosed is a novel nitrogen-containing heterocyclic derivative having a specific structure, which is useful as a constituent of an organic EL device. Also disclosed is an organic electroluminescent device having one or more organic thin film layers including a light-emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers contains the nitrogen-containing heterocyclic derivative. The organic electroluminescent device has high emission luminance and high luminous efficiency even at a low voltage.

Description

[Technical Field] The present invention relates to a novel nitrogen-containing heterocyclic derivative, a material for an organic electroluminescence element (organic EL element) using the same, an organic eL element, and more particularly to A nitrogen-containing heterocyclic derivative which can be used as a constituent component of an organic EL element is used for at least one layer of an organic compound layer, whereby an organic EL element having high luminous efficiency even at a low voltage is used. [Prior Art] The use of an organic EL device having an organic substance as a solid-state light-emitting type large-area full-color display element is expected, and many developments are underway. In general, the organic EL element includes a light-emitting layer and a pair of counter-electrodes sandwiching the layer. The term "luminescence" refers to a phenomenon in which electrons are injected from the cathode side and a hole is injected from the anode side when an electric field is applied between the electrodes; further, the electrons are recombined with the holes in the light-emitting layer to generate an excited state in an excited state. When returning to the ground state, 'release energy in the form of light. Previous organic EL elements have higher driving voltages and lower luminance and luminous efficiency than inorganic light-emitting diodes. Moreover, the deterioration of characteristics is also remarkable and it has not been put into practical use. Recently, organic EL elements are slowly being improved, but further high luminance and high luminous efficiency at low voltage are required. As a person who solves such problems, for example, in the patent document, there is disclosed an element using a compound having a benzimidazole structure as a light-emitting material, wherein the element is described at a voltage of 9 V at 2 〇〇 cd/m 2 . The brightness is illuminated. Further, in Patent Document 2 and Patent Document 3, a compound having a benzimidazole ring and an anthracene skeleton is described. However, the required luminance and luminous efficiency are higher than those of organic EL elements having such compounds. [Patent Document 1] Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. (US Publication No. 2006/147747) [Summary of the Invention]

The present invention has been made to solve the above problems, and an object thereof is to provide a novel nitrogen-containing heterocyclic derivative which can be used as a constituent component of an organic EL device by using the nitrogen-containing heterocyclic derivative for an organic compound layer. At least one layer is used to realize an organic EL element having high luminance and luminous efficiency even at a low voltage. The inventors of the present invention have conducted intensive studies in order to achieve the above object, and as a result, have found that a new nitrogen-containing heterocyclic derivative having a (four) structure can be used for at least a layer of an organic compound layer of the organic element. The present invention is accomplished by lowering the voltage and increasing the efficiency of the organic material. That is, the present invention provides a nitrogen-containing heterocyclic derivative derived from the following organism (benzimidazole compound "(1)).

[In the above formula (1), R1, substituted or not R are each independently a hydrogen atom 137088.doc 200936569 substituted alkyl group having a carbon number of 1 to 50, substituted or unsubstituted ring carbon number is 3 to 50 ring-based, substituted or unsubstituted carbonic acid group having 1 to 5 Å, substituted or unsubstituted aryl group having 6 to 2 ring carbon number, substituted or Unsubstituted heteroaryl group having 5 to 20 ring atoms (excluding substituted or unsubstituted carbazolyl or azacarbazolyl), atom, cyano, nitro, R1 to R6 The adjacent two groups may also be bonded to each other to form a substituted or unsubstituted saturated or unsaturated linking group constituting the ring structure; further, at least one of R1 to R6 is represented by the following formula (2) One of the valent groups derived from the fused ring compound represented. [Chemical 2]

(2) (In the above formula (7), RBu is independently a hydrogen atom, a substituted or unsubstituted aryl group having a ring carbon number of 6 to 6 Å, and a substituted or unsubstituted ring atom number is 5 a heteroaryl group of ~6〇 (the t, substituted or unsubstituted taste = broad: ... except for the base), substituted or unsubstituted alkyl having a carbon number of 1 to 50, substituted by " The ring-forming carbon number of the ring is 3~50, the adjacent groups of the cyano group and the nitrate can also be replaced by each other or the structure of the structure is replaced or unsubstituted. The present invention provides an organic electroluminescence device having an organic thin film layer having a light-emitting layer-containing layer between a cathode and a cathode 137088.doc 200936569, and at least one layer of the organic thin film layer containing the nitrogen-containing heterocyclic derivative. The nitrogen-containing heterocyclic derivative of the present invention and the organic EL device using the same have high luminous efficiency even at low electric I, and high luminous efficiency which is excellent in electron transport property. [Embodiment] The heterocyclic derivative is represented by the following formula (1): [Chemical 3] φ

In the above formula (1), R1 to R6 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, and a substituted or unsubstituted ring carbon number of 3 to 50. The cycloalkyl, substituted or unsubstituted carbon number is a "alkyl, substituted or unsubstituted aryl group having 6 to 2 ring carbon atoms, which is substituted or unsubstituted. a heteroaryl group having 5 to 20 ring atoms (excluding a substituted or unsubstituted carbazolyl group or an azacarbazolyl group), a functional atom, a cyano group or a nitro group as a substituted or unsubstituted The alkyl group substituted with a carbon number is exemplified by: methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, isobutyl second butyl, n-pentyl, n-hexyl, N-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, anthracene, 2-dihydroxyethyl, 1,3·dihydroxyisopropyl, 2 3 dihydroxy tert-butyl, trihydroxy 137088.doc 200936569 propyl, amine methyl, hydrazine-aminoethyl, 2-aminoethyl, 2-diaminoisobutyl, 1,2- Diaminoethyl, hydrazine: diamino isopropyl, 2,3-diamine _ tert-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, it dicyanoethyl , ;!, 3_Dicyanoisopropyl, 2,3-dicyano-t-butyl, 1,2,3-tricyanopropyl, nitroguanidino, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1>2-di-diethyl, 1'3-dinitroisopropyl, 2,3-dinitro-t-butyl, m Trinitropropyl, etc. As a substituted or unsubstituted cycloalkyl group having a ring carbon number of 3 to 50, examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a 4-methyl group. Cyclohexyl, K adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. As a substituted or unsubstituted functional alkyl group having 1 to 50 carbon atoms, A group in which a halogen atom selected from a fluorine atom, a gas atom, a bromine atom and an iodine atom is substituted with a hydrogen atom having a carbon number of 1 to 5 Å, and is exemplified by a trifluoromethyl group, 2'2, 2·. Trifluoroethyl, pentafluoroethyl, chloromethyl, gas ethyl, 2·gas ethyl, 2-isobutyl, iota, 2-diethylethyl, 1,3_tris, isopropyl, 2,3_ one gas - Tertiary butyl, 1,2,3-trimethylpropyl, bromoindolyl, bromoethyl, 2_ desert ethyl, 2-bromoisobutyl, 1,2-dibromoethyl, i,3_two Bromoisopropyl, 2'3-dibromo-t-butyl, i,2,3-tribromopropyl, iodomethyl, oxime-iodoethyl, 2-hydroxyethyl, 2-iodoisobutyl 1,2,2-diiodoethyl, diiodoisopropyl, 2,3-diiodo-t-butyl, hi-triiodopropyl, etc. The substituted or unsubstituted ring carbon number is 6~ Examples of the aryl group of 2〇 include: stupid group, 1-naphthyl group, 2-naphthyl group, 1-fluorenyl group, 2-hydrazino group, 9-fluorenyl group, phenanthryl group, 2-phenanthryl group, and 3-phenanthryl group. 4_phenanthryl, 9-phenanthryl, ruthenium four stupid base, 2_ 137088.doc 200936569 !: phenyl, 9, tetraphenyl, fluorenyl, fluorenyl, 4_ extension-based, 3-linked Base, 4_biphenyl, couplet 3, 2, 2, 2, 2, 2, 2, 2, 2, 2, 2, 2, 2, 2, 4, 4, 4, 4, 4, 4, 4 Cross-linked triphenyl-3 sense: its ..., o-f-phenyl, m-tolyl, p-toluene, m-;; base " p-(2-stylpropyl) stupyl, "yl-naphthyl, di Γ :, -Methyl sulfhydryl, 4|-methylbiphenyl, :Gyrotriphenyl _4-yl, "poor"不 不 丞 对 对 对 对 对 、 、 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ The base '", phenanthryl, ketone, thiol, sylylene, as a substituted or unsubstituted ring atomic number of 5, a heteroaryl group, a substituted or unsubstituted sulfonyl group, a nitrogen taste Except for saliva), U 举: 丨 咁 咁 夂 夂 、, 2 · pyrrolyl, 3-pyrrolyl, pyridinyl, 2 — pyridyl: pyridyl, 4-pyridyl, fluorenyl , 2_mercapto, 3_吲Γ anal, 5-mercapto, 6-fluorenyl, 7-fluorenyl, 1-isoisoisoindolyl, fluorenyl, 4 ·Isoindolyl, 5-isoindole, —, isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 1 benzofuryl, 3' benzoate , 4-benzopyranyl, 5-benzofuran 3, South genus 6 · stupid and astringent base, 7 · stupid and 1 fluorenyl, 1-isobenzoxyl, difenyl, furan, 4 _Iso-p-furanyl, 5-iso-p-furanyl, 6-, and 2-furanyl, 7-iso-p-furanyl, quinalyl, 3-quinazolyl, 4-5-indolyl, 6-啥琳基, 7-喧琳基, 8-喧琳基, 1_, 琳基, 3-isoquinolinyl, 4·isoquinolyl, 5-isoquinolinyl, 6-isoquinolinyl, 7 -isoquinolyl, 8-isoquinolinyl, 2-quino Porphyrin, 5-quinoxalinyl-6. quinoxalinyl, 1-cyridinyl, 2-cylinidyl, 3-cylinidyl, 4_ 137088.doc -11 - 200936569 morphyl, 6-morphine Pyridyl, 7-cyridinyl, 8-cyridinyl, 9-cyridinyl, 10-cyridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl , 9-Acridine, 1,7-morpholin-2-yl, 1,7-morpholin-3-yl, 1,7-morpholin-4-yl, 1,7-morpholin-5-yl 1,7-morpholin-6-yl, 1,7-morpholin-8-yl, 1,7-morpholin-9-yl, 1,7-morpholin-10-yl, 1,8-morphine Benzan-2-yl, 1,8-morpholin-3-yl, * 1,8-morpholin-4-yl, 1,8-morpholin-5-yl, 1,8-morpholin-6-yl 1,8-morpholine-7-yl, 1,8-morpholin-9-yl, 1,8-morpholin-10-yl, 1,9-morpholin-2-yl, 1,9- Polinolin-3-yl, 1,9-morpholin-4-yl, 1,9-morpholin-5-yl, 1,9-morpholine--6-yl, 1,9-morpholin-7- , 1,9-morpholin-8-yl, 1,9-morpholin-10-yl, 1,10-morpholin-2-yl, 1,10-morpholin-3-yl, 1,10- Phenanthroline-4-yl, 1,10-° non-scared · _ 5 -yl, 2,9 - spurred · _ 1 -yl, 2,9 - stimuli · - 3 -yl, 2,9 - 徘-4 _ group, 2,9-morpholin-5-yl, 2,9-morpholin-6-yl, 2,9-morpholin-7-yl, 2, 9-morpholin-8-yl, 2,9-morpholin-10-yl, 2,8-morpholin-1-yl, 2,8-morpholin-3-yl, 2,8-morpholin-4 -yl,2,8-morpholin-5-yl, 2,8-morpholin-6-yl, 2,8-morpholin-7-yl, 2,8-morpholin-9-yl, 2,8 -morpholin-10-yl, 2,7-morpholin-1-yl, 2,7-morpholin-3-yl, 2,7-morpholin-4-yl, 2,7-morpholin-5- Base, 2,7- ❿ p-non-lin _ 6-yl, 2,7 -11-non-lin-8-yl, 2,7-morphine-9-yl, 2,7-carnitin-10-yl, 1 -»Non-cultivation base, well foundation, 1-° non-n plugging base, 2-° non-嗟p well base, 3- • morphine 0g arable base, 4-morphine cultivating base, 10-morphine p well base, 1-# well base, 2-_ well base, 3-morpho p well base, 4-morphine well base, 10-lin well base, 2-mercapto group, 4-ρ sulfhydryl group, 5-saki saliva Base, 2-p-position, sit-up, 5-position β-spinyl, 3-°-fusinyl, 2-tresyl, 3-π-septenyl, 2-methyl-bipir-1-yl , 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrole-5-yl, 3-mercaptopyrrol-1-yl, 3-methylpyrrol-2-yl , 3-methylpyrrol-4-yl, 3-methyl 137088.doc -12- 200936569 pyrrole·5·yl, 2-t-butylphosphonium·'yl, 2-methyl_1_吲哚Base, 4· propyl propyl) Strategy -! _-Yl, 4-methyl-3-yl flower +, 1 ° Primer ° 2_ third flower group, 2_ methyl indole -Μ

The group consisting of a fluorenyl group and the like is exemplified by a fluorenyl group, a fluorenyl group, and a butyl group. 7卞, the two atoms adjacent to the odor atom and the iodine atom R6 are bonded to each other to form a linking group which may constitute an unsaturated structure of the adjacent two groups constituting the ring structure. Or unsubstituted saturating or at least one of the cores 6' is preferably R1 derived from the fused ring compound represented by the following formula (7): [Chemical 4] ^

In the above formula (2), RU to Rl°a are each independently a hydrogen atom, a substituted or unsubstituted aryl group having a ring-bonding carbon number of 6 to 6 (), a substituted or unsubstituted ring atom. a heteroaryl group of 5 to 60 (except for a 'substituted or unsubstituted sorry group, aza(tetra) group)' substituted or unsubstituted carbon group having a carbon number of 1 to 50, substituted or The unsubstituted cyclocarbon group having a ring carbon number of 3 to 5 Q, a tooth atom, a cyano group or a nitro group.

The substituted or unsubstituted ring-forming carbon number represented by Rla~R1Ga is 6~6〇137088.doc -13- 200936569, and the substituted or unsubstituted ring-forming atomic number is 5~6〇 The heteroaryl group, the substituted or unsubstituted carbon number is an alkyl group, substituted or unsubstituted, and the ring carbon group having a ring carbon number of 3 to 50 is selected from R1 to R6. a group exemplified by the substituent shown. The adjacent two groups of RU to C may be bonded to each other to form a saturated or unsaturated linking group which constitutes a ring structure or an unsubstituted group. Further, they may be bonded to each other to form a linking group constituting the ring structure, and form a spiro structure together with the five-membered ring in the first structure formed by R9*» and ❹R bonding. The fused ring compound represented by the general formula (2) In the derived group (_fl), the bond may also be located on any carbon forming the anthracene skeleton. In this case, _FL is directly bonded to any atom of the benzoimidazole skeleton.

Any atom contained in Rla~R1Ga (except for hydrogen atom, self atom, gas group and nitro group). For example, when any of RU to Rl〇a is an aryl group, the bond may also be on any carbon of the aryl group. In this case, the skeletal frame is bonded to any atom of the benzimidazole skeleton via an aryl group. The nitrogen-containing heterocyclic derivative represented by the formula (1) is preferably represented by any one of the following formulas 0) to (5). [Chemical 5]

In the above formulae (3) to (5), R1 to R6 are the same as defined above, and FL is a group derived from the fused ring compound represented by the above formula (7). The oxime derived from the fused ring compound (10) is particularly preferably represented by the following formula (6).丨-((Structure) _Ar2 (6) Benzene =) two r, a single bond or an aryl group. Examples of the aryl group include an aryl group, and examples thereof include a phenyl group, i, and the like, and a chlorine atom or an aryl group. As. - (筅, 孩, naphthyl, 2, naphthyl, 1, 2 or 4-fluorenyl (寻~)) selected from the following divalent groups. [Chem. 6] ❹

Substituting: or unsubstituted ..... base..., as an arbitrary base, into a photo# alkyl group having a carbon number of 1 to 20, and a cycloalkane having a carbon number of 3 to 20 (carbazolyl, It is 6~) The aryl group of 20, the heteroaryl group having a carbon number of 3 to 20 is a ring of 3 to 20, and the number of rings is = (4) the filament group of 1 to 2G, the aromatic number of the carbon number & ～30 aryloxy group, carbon number 7~31 South atom, nitro group, cyano group, thio group and the like. "The compound represented by (1) (BI-FL below) can be synthesized by the following method 137088.doc 15 200936569: the corresponding halogen substituent of benzimidazole (BI-X below, including halogen substitution) The aryl substituent) is coupled with a corresponding boronic acid or boronic acid ester derivative (FL-B(OR) 2); or by a general Suzuki coupling reaction, Tetrahedron Lett., 38, 3447 (1997),

Tetrahedron Lett., 38, 3841 (1997) 'Tetrahedron Lett., 38, • 1197 (1997), etc., such as boric acid or boric acid ester derivatives of benzimidazole (BI-B(OR) below) 2) reacting with a corresponding halogen substituent (hereinafter, FL-X, containing a halogen-substituted aryl substituent); and depending on the conditions, etc., it can be easily selected and determined by a professional. . [Chemistry 7]

137088.doc •16· 200936569

Substituents and integers selected from R1 to R6 and Rla to R10a of the formula (7). (In the above formula, the 'X-type halogen atom' R, η and L are preferably used as the material for organic ELs in order to satisfy the nitrogen-containing heterocyclic derivative of the present invention of the formula (1), and particularly preferably used. The luminescent material, the electron injecting material, or the electron transporting material. The following table π is a specific example of the nitrogen-containing heterocyclic derivative represented by the general formula (1) of the present invention, but is not limited to the exemplified compounds.

137088.doc -17· 200936569 [化9] ❹ [化 10] °^o α^ο〇 ❿

137088.doc _ 18- 200936569 [化]

[化 12]

137088.doc •19· 200936569 [Chem. 13]

[Chem. 14] 137088.doc -20- 200936569 [Chem. 15]

[4b 16]

-21- 137088.doc 200936569 [Chem. 17]

[Chemical < 18]

Next, the organic EL device of the present invention will be described. The organic EL device of the present invention has one or more organic thin film layers containing a light-emitting layer between the cathode and the anode, and at least one layer of the organic thin film layer contains the nitrogen-containing heterocyclic derivative of the present invention. 137088.doc • 22-200936569 In a preferred aspect of the invention, the organic thin layer has an electron injecting layer or an electron transporting layer, and the electron injecting layer or the electron transporting layer contains the nitrogen-containing heterocyclic derivative of the present invention. . Further, the electron transporting layer preferably contains a nitrogen-containing heterocyclic derivative, and the electron injecting layer or the electron transporting layer further preferably contains a reducing dopant. In another preferred embodiment of the invention, the light-emitting layer contains the nitrogen-containing heterocyclic derivative of the present invention. Further, the light-emitting layer may further contain at least one of a phosphorescent dopant and a fluorescent dopant in addition to the nitrogen-containing heterocyclic derivative of the present invention. By containing the above dopant, it can function as a phosphorescent luminescence and a luminescent light-emitting layer. Representative examples of the organic EL element of the present invention include the following: (1) Anode/light-emitting layer/cathode (2) Anode/hole injection layer/light-emitting layer/cathode (3) Anode/light-emitting layer/electron injection layer/ Cathode (4) Anode/hole injection layer/light-emitting layer/electron injection layer/cathode (5) anode/organic semiconductor layer/light-emitting layer/cathode (6) anode/organic semiconductor layer/electron barrier layer/light-emitting layer/cathode ( 7) Anode/organic semiconductor layer/light-emitting layer/adhesion improving layer/cathode (8) anode/hole injection layer/hole transport layer/light-emitting layer/electron injection layer/cathode (9) anode/insulation layer/light-emitting layer/ Insulation/Cathode (1 〇) Anode/Inorganic Semiconductor Layer/Insulation Layer/Light Emitting Layer/Insulation Layer/Cathode (11) Anode/Organic Semiconductor Layer/Insulation Layer/Light Emitting Layer/Insulation Layer/Cathode (12) Anode/Insulation Layer / hole injection layer / hole transmission layer / luminescent layer / insulation 137088.doc -23- 200936569 layer / cathode: (13) anode / insulation layer / hole injection layer / hole transmission layer / luminescent layer / electronic 'master Incoming layer/cathode, etc. 'but not limited to these. Among these, it is generally preferred to use the constitution of (8). The nitrogen-containing heterocyclic derivative of the present invention can be used for any organic thin film layer of an organic EL element. It is preferably used in an emission band or an electron transmission band, and particularly preferably used for an electron injection layer, an electron transport layer, and a light emission. Floor.

The composition of (8) is shown in the figure. The organic EL element 1 includes a cathode and an anode 2, a hole injection layer 3, sandwiched therebetween, a hole transport layer 32, a light-emitting layer 33, and an electron injection layer 34. The hole injection layer 31, the hole transport layer 32, the light-emitting layer 33, and the electron injection layer 34 correspond to a plurality of organic thin film layers. At least one of the organic thin film layers 31 to 34 contains the nitrogen-containing heterocyclic derivative of the present invention. Hereinafter, each member of the organic EL element will be described. The organic EL element is usually fabricated on a substrate which supports the organic component element. It is preferred to use a smooth substrate. When light is taken out from the substrate, it is preferable that the substrate has light transmissivity, and the transmittance of light in a visible region having a wavelength of 4 Å to 700 nm is 50% or more. As the light-transmitting substrate, for example, a glass plate, a synthetic resin plate or the like is preferably used. Examples of the glass plate include soda lime glass, bismuth-containing glass, lead glass, aluminosilicate glass, borosilicate glass, bismuth boron bismuth glass, and quartz. Further, examples of the synthetic resin sheet include a polycarbonate resin, an acrylic resin, a polyethylene terephthalate resin, a polyether sulfide resin, and a polyfluorene resin. 137088.doc -24· 200936569 The anode has the effect of injecting a hole into the hole injection layer, the hole transmission layer or the light-emitting layer, and has a work function of 4.5 eV or more. Specific examples of the anode material include: indium tin oxide _), an indium oxide and an oxidized product (IZO), a mixture of ITO and cerium oxide (ITC 〇), a mixture of lz 〇 and an oxidized metal (IZCO). Indium oxide and oxidized mixture (ic), a mixture of zinc oxide and aluminum oxide (AZO), tin oxide (NESA), gold and silver, Ming, copper, and the like. The anode can be formed from the electrode materials by a steaming method or a method.

时 When the light from the luminescent layer is taken out from the anode, it is preferable to make the transmittance of illuminance greater than 10%. Further, the sheet resistance of the anode is preferably several hundred Ω / □ or less. The film thickness of the anode is also dependent on the material, and is usually 1 〇 nm to 1 μηη ', preferably 1 〇 2 〇〇 nm. The light emitting layer has the following functions. (1) Injection function: when an electric field is applied, a hole can be injected from the anode or the hole injection layer, and electrons can be injected from the cathode or the electron injection layer. (11) Transmission function. The injected electric charge is generated by the force of the electric field (electron) The function of moving with the hole (Hi) light-emitting function: the electron and the hole are recombined, whereby the function of light-emitting is used as a method of forming the light-emitting layer, and a known method such as steaming, spin coating, or LB method can be applied. The luminescent layer is particularly preferably a molecular deposition film. The so-called molecular deposition film refers to a film formed by depositing a material compound in a gas phase state, or a film formed by compounding a material in a liquid state or a liquid phase. The film is usually formed by agglomerating structure, high order. The difference in structure, or the difference in function due to this, is distinguished from the film formed by the method of (3) 137088.doc •25·200936569 (molecular accumulation film). Further, a binder such as a resin and a material compound are dissolved in a solvent to form a solution, and then thinned by a spin coating method or the like, whereby a light-emitting layer can also be formed. ❹ ❹ As a light-emitting material or a doping material which can be used for the light-emitting layer, for example, anthracene, naphthalene, phenanthrene, anthracene, fused tetraphenyl, hexabenzobenzene, anthracene, fluorescein, anthracene, anthracene, naphthoquinone ,methodone, fluorescein, naphthoquinone, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldehyde nitrogen, dibenzo-xine, double Styrene, t well, cyclopentadiene, ruthenium metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, stilbene, vinyl fluorene, diamine hydrazine An azole, a pyran, a thiopyran, a polydecyl sulfonyl group, a genus phthalocyanine, a saliva-integrated quinone ketone compound, a chitosan, a red (iv), and such derivatives or glory pigments, but the like. Heart 狖 As a specific example of the host material which can be used for the light-emitting layer, a compound represented by (i) to (ix) can be cited. An asymmetrical enthalpy represented by the following formula (1). [Chem. 19]

(I) (wherein, the Ar00 lanthanide is substituted or not ^^^. The substituted carbon number is a condensed scent group. Αγ〇〇2 Chuanzhi, Λ 'substituted or unsubstituted ring The crucible reaches an aromatic group of 6 to 50. χ001~* is a knife that is independently substituted or unsubstituted 137088.doc -26 - 200936569 shoulder; private carbon number 6~5G aromatic group, substituted or Unsubstituted ring-forming ring Z is 5 5G of aromatic heterocyclic group, substituted or unsubstituted carbon number I 50 thiol group, substituted or unsubstituted carbon number of 1~50 a substituted or unsubstituted aryl group having a carbon number of 7 to 50, substituted or unsubstituted, having an aryloxy group having a ring carbon number of (iv), substituted or unsubstituted =, ring rabbit number 6 to 5G of the arylthio group, substituted or unsubstituted carbon number is an alkoxycarbonyl group of a hydrazine, a carboxyl group, an atom, a cyano group, a nitro group, a hydroxy group, and a hydroxyl group, respectively, an integer of 0 to 4. An integer of ～3. In the case of the above, □ may be the same or different.) An asymmetric monoterpene derivative represented by the following formula (ii).

(wherein, A, and Ar_ are each independently substituted or unsubstituted, an aromatic ring group having a ring carbon number of 6 to 50, respectively, an integer of Η, wherein, " and A, and When the bonding position on the benzene ring of ΑΓ_ is a bilaterally symmetric type, Ar003 & am listens to MAr is not the same, and when m or n is an integer of 2 to 4, 111 and η are different integers. R~R is independently a hydrogenogen+, substituted or unsubstituted ring-and-carbon group having a ring carbon number of 6 to 50, and a substituted filament-like aromatic heterocyclic ring having 5 to 50 ring atoms. The substituted, unsubstituted or unsubstituted carbon group of uo, substituted or unsubstituted ring carbon number is 3 to other naphthenes 137088.doc -27- 200936569 base, substituted or unsubstituted The carbon number is alkoxy, substituted or unsubstituted aralkyl having 7 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 5 carbon atoms, a substituted or unsubstituted alkylene group, a carboxyl group, Atom, a cyano group, Danxiao Ji, by group.) Asymmetric pyrene derivatives represented by the following formula (iii) represented by the. [Chem. 21]

(wherein ArG()5 and Ar_ are each a substituted or unsubstituted aromatic group having a ring carbon number of 6 to 50. τ 001 τ 〇〇2 x

〜 knife is a substituted or unsubstituted phenyl, substituted or unsubstituted anthranyl, substituted or unsubstituted (tetra), or substituted or unsubstituted dibenzo thiophene Dibe_ilolylene. m is an integer of 〇~2, and 11 is an integer of 1 to 4 integers. s is an integer of 0 to 2, and t is 〇~4. An asymmetric anthracene derivative represented by the following formula (iv). 137088.doc •28- 200936569 [Chem. 22]

〇v) ❹ (wherein ArGQ1 and ArGG2 are independently substituted or unsubstituted fused aromatic ring groups having a ring number of 10 to 20 carbon atoms. And Ar is independently a hydrogen atom, or substituted or not The substituted ring-rings are 6 to 50 aromatic ring groups. R~R 2G are independently a hydrogen atom, a substituted or unsubstituted aromatic ring group having a ring carbon number of 6 to 50, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring carbon number of 3 〇5〇 of cycloalkyl, substituted or unsubstituted carbon number is 丨~ched alkoxy, substituted or unsubstituted aralkyl having 7 to 50 carbon atoms, substituted or unsubstituted An aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted carbon number of 2 to 5 Å An oxycarbonyl group, a substituted or unsubstituted alkylene group, a fluorenyl group, a tooth atom, a cyano group, a cis group or a thiol group. 'The neighboring parties A, 7, Ar_, R (n9 and 尺_ can be plural May form a saturated or unsaturated cyclic structure of the anthracene derivative represented by the following formula (V) represented by the. 137088.doc -29- 200936569 [of 23]

(wherein R to R each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted cyclohexane having a ring number of carbon φ of 3 5 Å; A substituted or unsubstituted aryl group having a carbon number of from 6 to 50, substituted or unsubstituted, having an alkoxy group having 1 to 5 carbon atoms, substituted or unsubstituted, or substituted by A An aryloxy group having 6 to 5 Å, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, substituted or not The substituted arylamino group having a ring carbon number of 6 to 5 Å or the substituted or unsubstituted heterocyclic group having a ring number of 5 to 5 Å 'a and b respectively represent an integer of 1 to 5 When the ratio is 2 or more, R or R〇22 may be identical to each other, or may be different from each other, and ' and 'R021 or R〇22 may be bonded to each other to form a ring, r〇 2>r〇24, R025 and RQ26, ruler 27 and R〇28, R()29 and r03() may be bonded to each other to form a ring. L represents a single bond, -0-, -S-, -N(R )-(R is substituted or unsubstituted • Alkyl group having a carbon number of 1 to 5 Å Or a substituted or unsubstituted aryl group having a ring carbon number of from 6 to 50, a substituted or unsubstituted alkyl group having a carbon number of from 1 to 50, or a substituted or unsubstituted ring. An extended aryl group having a carbon number of 6 to 50.) An anthracene derivative represented by the following formula (vi). 137088.doc -30· 200936569 [Chem. 24]

❻

The substituted carbon number is 丨~"alkyl, substituted or unsubstituted cycloalkyl having a ring number of 3 to 50, substituted or unsubstituted ring carbon number of 6~5〇 The substituted, unsubstituted or unsubstituted carbon number is an alkoxy group, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted carbon number of 1 An alkylamino group of ～50, a substituted or unsubstituted arylamino group having a ring carbon number of 6 to 50, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; c, d, e, and f represent integers of 1 to 5, respectively, and when they are 2 or more, R 〇 3 、, R 〇 32, R 〇 36, or γη may be identical to each other. 'Also different from each other, and between the rulers, between R, between RQ36 or between R037, they may be bonded to each other to form a ring, and R〇33 and V34, RG38 may be bonded to each other to form a ring. Represents a single bond, 〇_, -S_, -N (RHR is a substituted or unsubstituted alkyl group having a 丨~% alkyl group, or a substituted or unsubstituted ring carbon number of 6 to 5 〇 The aryl group, the substituted or unsubstituted alkyl group having a carbon number of 50, or the substituted or unsubstituted aryl group having a ring carbon number of 6 to 50. A snail derivative represented by the following formula (vii). 137088.doc -31- 200936569 [Chem. 25]

A compound represented by the following formula (viii), which is represented by the following formula (viii). m (wherein A0丨1~A. 13 κ 丨丨 && 丄 A is substituted or unsubstituted into ginseng

g. ,, . + Knife is independently a hydrogen atom, or a substituted or unsubstituted aryl group having a ring carbon number of 6 to 5 g.广~r(4) = = aryloxy group having a hydrogen atom, a carbon number of 仏6, a carbon number of 1 to 6 in the ring, and an aryloxy group having a carbon number of 6 to 18 in the ring. An aralkoxy group having a carbon number of 7 to 18, an arylamine group having a ring number of 6 to 16 carbon atoms, a nitrite, a cyano group, an ester group having a carbon number of 2 to 6, or a south atom; At least one of "~, 6 is a group having a condensed aromatic ring of 3 or more rings. A compound represented by the following formula (ix). 137088.doc -32- 200936569 [Chem. 27]

(4)

(wherein, 11051 and 1^052 represent a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 5 carbon atoms, a substituted or unsubstituted aryl group having a ring carbon number of 6 to 5 Å, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and a substituted or unsubstituted carbon number 1 to 50 of an amino group, a cyano group or a south atom. R051 and R052 which are bonded to different sulfhydryl groups may be identical to each other or different from each other; R051 and R052 which are bonded to the same fluorenyl group may be the same, Dimensions (6) and ... 54 represent a hydrogen atom, a substituted or unsubstituted carbon number of 丨 别 别, a substituted or unsubstituted aralkyl group having a carbon number of 7 to 50, substituted or Unsubstituted aryl group having 6 to 50 ring carbon atoms, or substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R 〇 bonded to different fluorenyl groups The R and R may be the same or different from each other; the R and R054 bonded to the same fluorenyl group may be the same or different. Ar011 and Ar012 indicate that the benzene ring is a total of 3 or more substituted or Unsubstituted condensed polycyclic aromatic group, or benzene ring and heterocyclic ring in total of 3 or more substituted or unsubstituted condensed polycyclic heterocyclic groups bonded by carbon and sulfhydryl groups, Aron and Ar012 η is an integer of 1 to 10. In the organic EL device of the present invention, a phosphorescent dopant may be contained in the light-emitting layer in addition to the light-emitting material of the present invention as needed. And/or rong 137088.doc -33- 200936569 optical dopants χ ' can also be laminated on the luminescent layer comprising the compound of the invention comprising a luminescent layer comprising the dopants. A triplet exciton luminescence compound. If it emits light from a triplet exciton, it is not particularly limited, and preferably contains at least one metal selected from the group consisting of Ir Ru, Pd, Pt, 〇s, and Re. The metal disorder is preferably a tetralin metal complex or an orthometalated metal disorder. The phosphorescent compound may be used singly or in combination of two or more. As the porphyrin metal complex, it is preferred. It is a porphyrin platinum complex.

There are various ligands for forming an ortho-metallated metal complex. Preferred examples of the ligand include a compound having a phenyl acridine skeleton, a bipyridyl skeleton or a phenanthroline skeleton; Pyridine derivative; 7,8-benzoquinoline derivative; 2-(2-thienyl)pyridine derivative; 2_〇•naphthyl)pyridine derivative; 2-phenylquinoline derivative and the like. These ligands may also have substituents as needed. In particular, those having a fluoride or a trifluoroindenyl group are preferably used as a blue dopant. Further, the auxiliary ligand may have a ligand other than the above ligand such as propionic acid or picric acid. Specific examples of the above metal complex include tris(2pyridylpyridine)fluorene, tris(2-phenylpyridine)fluorene, tris(2-phenylpyridinium)palladium, and bis(2·phenyl) Mouth than bite) turn, three (2-phenyl bite) hungry, three (2_phenyl 〇 than bite) 铢, 八ethyl Ming Wailin, octaphenyl 叶叶琳, 八乙把外琳, Although octaphenylene or the like is not limited thereto, an appropriate complex is selected in accordance with the desired luminescent color, element performance, and host compound to be used. The content of the material (4) as a dopant in the light-emitting layer is not particularly limited and may be appropriately selected as needed, and is, for example, 0.^70% by mass, preferably 137088.doc -34-200936569 mass/. . If the content of the phosphorescent compound is less than the mass. However, the light is weak, and the effect of the effect is not fully exerted. When the shape exceeds 70 masses, the concentration quenching phenomenon becomes remarkable, and the performance of the element is lowered.

乍 is a fluorescent dopant, preferably blended with the desired luminescent color, from an amine 1 compound, an aromatic compound, a tris- (8)-based (tetra) ing complex, etc. a derivative of a tetraphenylbutadiene derivative, a stilbene f-aromatic derivative, an oxadiazole derivative, or the like, and further a good stupid vinylamine compound, a styryldiamine compound, and an aryl amination. Oral, aryl diamine compound. Further, a condensed polycyclic aromatic compound which is not an amine compound is also preferred. These fluorescent dopants may be used singly or in combination of plural kinds. The stupid vinylamine compound and the styryldiamine compound are preferably represented by the following formula (A). [化 28] ❹

P (A) (wherein, Ar101 is a p-valent group derived from benzene, naphthalene, phenylidene, terphenyl, stilbene, and a stupid vinyl aryl group). Ar 02 and A 〆 03 are respectively carbon number. It is a 6 to 20-membered aromatic hydrocarbon group 'Ar1Q1, Ar1Q2 and Ar1. 3 may be substituted. Any one of Ar~Ar103 may be substituted by a styryl group. Further preferably, at least one of Ar1Q2 or Ar(1) is substituted with benzene. It is substituted by a vinyl group. p is an integer of 137088.doc -35- 200936569. The number is preferably an integer of 1 to 2. Here, as an aromatic hydrocarbon group having a carbon number of 6 to 20, Phenyl, naphthyl, ortho-amine benzyl, phenanthryl, and triphenyl are widely used as the arylamine compound and the aryldiamine compound, and are preferably represented by the formula (B). W ^ [Chem. 29]

T-type 肀, Ar111 is a q-valent-, 'π 恧 恧 经 疋 substituted 疋 aryl group with a carbon number of 6 to 40, or a substituted or unsubstituted ring atomic number of 5 to 4 〇 The base 'wy 3 is a substituted or unsubstituted aryl group having a ring carbon number of 6 to 40, or a substituted or unsubstituted heteroaryl group having a ring number of (10). q is an integer of 1 to 4, preferably an integer of 丨~2. ❹ As the above-mentioned aryl group and heteroaryl group, for example, a phenyl group, a naphthyl group, an ortho-amine phenanthryl group, an inverse group, a corolla group (c〇r〇n state, a biphenyl group, a terphenyl group) Base, (tetra)yl, (tetra)yl, fluorenyl, benzoxenyl, dimethyldiphenyl, diphenyl-o-amine benzyl, fluorenyl, carbazolyl, pyridyl, benzoxanthyl, Diterpenoid, divalent lysine, diphenylethylene, aryl, benzyl, fluorenyl, phenyl, 55, benzoxyl, phenyl-o-benzyl, diamyl Etc., the preferred county Zanzi 衩 is naphthyl, o-aminobenzyl, fluorenyl, fluorenyl. As a preferred substituent of the above aryl and heteroaryl, may be mentioned: carbon number I37088. Doc -36- 200936569 is an alkyl group of 1 to 6 (ethyl, methyl, isopropyl-n-propyl second butyl, tert-butyl, pentyl, hexyl, etc.), a ring having a carbon number of 3 to 6 Alkyl (cyclopentyl, cyclohexyl, etc.), alkoxy having a carbon number of 丨~6 (ethoxy, decyloxy, isopropoxy, n-propoxy, second butoxy, third butyl) Oxyl, pentyloxy, hexyloxy, etc.), ring with a carbon number of 3 to 6 An oxy group (cyclopentyloxy group, cyclohexyloxy group, etc.), an aryl group having a ring carbon number of 6 to 4 Å, a ring carbon number of 6 to 4 Å, an amine group substituted with an aryl group, and a aryl group An ester group having an aryl group having a carbon number of 6 to 40, an ester group having an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, a functional atom, etc. The light-emitting layer may optionally contain a hole transporting material and electron transport. The material and the polymer binder. The film thickness of the light-emitting layer is preferably 5 to 5 nm, more preferably 7 to 50 nm, and most preferably 1 to 5 nm. If less than 5 nm, it exists. It is difficult to form a light-emitting layer, and it is difficult to adjust the chromaticity. If it exceeds 5 〇 nm, there is a rise in the driving voltage. The hole injection layer and the hole transport layer help to inject holes into the light-emitting layer and transmit them to In the layer of the light-emitting region, the mobility of the hole is large, and the free energy is small, and Φ is usually less than 5·5 eV. As the material of the hole injection layer and the hole transport layer, it is preferable to have a smaller electric field strength. The hole is transported to the material of the light-emitting layer. Further, for example, when an electric field of 104 to 106 v/cm 2 is applied, the mobility of the hole is 丨0-4 cm 2 /V. The material of the hole injection layer and the hole transport layer is not particularly limited, and a charge transport material which is conventionally used as a hole in a light conductive material or a hole injection layer for an organic EL element may be selected. And any of the well-known electron-transfer layers. In the hole injection layer and the hole transport layer, for example, the following formula can be used: 137088.doc -37- 200936569

An aromatic amine derivative. [化30]

Generation (in the form of Central, "~, and Μ1 η3 are substituted or unsubstituted aryl groups with a carbon number of 6 to 50, or substituted or unsubstituted:: a 5- to 50-membered heteroaryl ' Α γ 2 〇 3 Α γ, which is substituted or substituted with -i to form an aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring atom number It is a heteroaryl group of 5 to 50. a~c and ρ~Γ are integers of 〇~3: AW and Ar-, Ar, Ar-, Ar, and Ar208 can be connected to each other respectively to form a residual or unsaturated Ring.)

Specific examples of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms include a phenyl group, a naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, and a 1-phenanthrene group. Base, 2·phenanthryl, 3—phenanthryl, 4 —phenanthryl, 9·phenanthryl, ruthenium+stupyl, 2—thick tetraphenyl, 9-fused tetraphenyl, 1-indenyl, 2-indole Base, 4-negative, 2-linked stylyl, 3-phenylbiphenyl, 4-biphenyl, bis-triphenyl, 2-tris-3-yl, conjugated triphenyl-2-yl, cross-linking Benzene-4-yl, m-triphenyl, m-triphenyl-2-yl, o-tolyl, m-tolyl, p-toluene to t-butylphenyl, p-(2-phenylpropyl)phenyl , 3-methyl-2-naphthalene, _methyl-1-naphthyl, 4-methyl-1-indenyl, 41-methylbiphenyl, 4"-t-butyl-p-terphenyl- 4-Based. 137088.d〇i -38 - 200936569 Specific examples of the substituted or unsubstituted extended aryl group having a ring carbon number of 6 to 5 Å include the removal of one hydrogen atom from the above aryl group. Specific examples of the substituted or unsubstituted heteroaryl group having a ring-shaped atomic number of 5 to 5 Å include: 口 比 比哈基, 2 "比嘻基, 吼略基", 2-pyridyl, 3-pyridyl, 4·pyridyl, fluorenyl, 2-hydrazino, 3, bromo, 4-bromo, 5-10, 6, c, 7_β 哚 哚 1_isoindolyl, 2-isoindolyl, 3_isoindolyl, 4_isoindole^yl 5_isoindolyl, 6-isoindolyl, 7-isoindole Sulfhydryl, 2-furyl, 3-funanyl, 2-benzofuranyl, 3-benzofuranyl, benzofuranyl, 5-phenylidene, 6-benzofuranyl, 7-benzo Furanyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl , quinolyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-fluorenyl, 1-isoquinolyl, 3- Isoquinolyl, 4-isoquinolyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxaline φ, 5_ Porphyrin, 6-quinoxalinyl, 1-oxazolyl, 2-oxazolyl, 3-zirthyl, 4-oxazolyl, 9-oxazolyl, 1-cyridinyl, 2_ Carribidinyl, 3_ carbyl, 4, aryl, 6-«# pyridine, 7-morphinyl, 8-cyridinyl, 9-undetermined , morphine, 1-° 丫 base, 2-» 丫 base, 3-〇丫 base, 4 _ acridinyl, 9-acridinyl, 1,7-morpholin-2-yl, anthracene , 7- phenanthroline _3• base, l57_ 祚琳_4~ base, 丨, 7·琳琳巧-基, 〗, 7-brown scare *-6-based, 1,7-啡*#-8- 1,7-Nylan-9-yl, 1,7-morphine-10-yl, 1,8-morphine_2-yl, ι,8-morphol-3-yl, 18-morphine _ 4_yl, 18-phenanthroline-5, guanidine, phenanthroline-6-yl 1,8-morphine-7-yl, 1,8-morphine-9-yl, 1,8-brown, you_ 〇_基,ι,9- 137088.doc -39- 200936569 morphine-2-yl, 1,9-morphin-3-yl, 1,9-11 non-lin-4-yl, 1,9-morphine Lin-5-yl, 1,9-morpholin-6-yl, 1,9-morpholin-7-yl, 1,9-morpholin-8-yl, 1,9-morpholin-10-yl, 1,10-morpholin-2-yl, 1,10-morpholin-3-yl, 1,10-morpholin-4-yl, 1,10-morpholin-5-yl, 2,9-morpholine -1-yl, 2,9-morpholin-3-yl, 2,9-morpholin-4-yl, 2,9-morpholin-5-yl, 2,9-morpholin-6-yl, 2 , 9-morpholine - • 7-yl, 2,9-morpholin-8-yl, 2,9-morpholin-10-yl, 2,8-morpholin-1-yl, 2,8-morpholine 3-yl, 2,8-morpholin-4-yl, 2,8-morpholin-5-yl, 2,8-morpholin-6-yl, 2,8-morpholin-7-yl, 2 , 8-morpholin-9-yl 2,8-morpholin-10-yl, © 2,7-morpholin-1-yl, 2,7-morpholin-3-yl, 2,7-morpholin-4-yl, 2,7-morph Porphyrin-5-yl, 2,7-morpholin-6-yl, 2,7-morpholin-8-yl, 2,7-morpholin-9-yl, 2,7-morphin-10-yl, 1-morphine, well base, 2-morphine, 1-徘喧p well base, 2-morphine stalk base, 3-° non-Serbian, 4-° non-° plugged well, 10-^ • Non-sighing p-base, l-lM cultivating base, 2-morphic No. 3 ρ well base, 3-morpho ρ well base, 4-morphine p well base, 10-morpho p well base, 2-噚Azolyl, 4-oxazolyl, 5-carbazolyl, 2-oxadiazolyl, 5-.1 dioxin, 3-Of-s-s-indenyl, 2-oxinyl, 3-0 Tertiary, 2 -fluorenyl 11 piro-1 -yl, 2-methyl-0-s--3-yl, 2-methyl 0-pyridin-4-yl, 2-methyl 0-pyrid-5-yl 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methyl. Bior-5-yl, 2-tert-butylindol-4-yl, 3-(2-phenylpropyl) 0 pirin-1 -yl, 2-methyl-1 -0 π π , 4-methyl-1 -0-introduced 0-methyl, 2-mercapto-3-indenyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indenyl, 4 - tert-butyl-1-indenyl, 2-tert-butyl-3-indenyl, 4-tert-butyl-3-indenyl. Specific examples of the substituted or unsubstituted heteroaryl group having 6 to 50 ring carbon atoms include those obtained by removing one hydrogen atom from the above heteroaryl group. 137088.doc -40- 200936569 Further, the hole injection layer and the hole transport layer may contain a compound. [化31]

~Arm is

A substituted aryl group having a ring carbon number of 〜5〇, or a substituted or not 5~50 hydrazine | T. ^ a substituted ring atom number is fluorenyl. L is even,,. The group is a single bond, or a substituted aryl group having a ring carbon number of 6 to 50 or a substituted or unsubstituted ring group having a ring number of 5 to 50. x is an integer of 〇~5. ), /r232 and A# can be interconnected to form a saturated or saturated ring. Here, as a substituted or unsubstituted aryl group and an aryl group having a ring carbon number of 6 to 5 Å, and a substituted or unsubstituted aryl group having 5 to 5 ring atoms and Specific examples of the heteroaryl group include the same as described above. Further, as a specific example of the material of the hole injection layer and the hole transport layer, three (four) biological H derivatives, cardiac derivatives, t2 alkyl alkane derivatives, pyrazoline derivatives, pyrazolium derivatives, Phenylenediamine Ho, Heteroamine Derivatives, Amine Substituted (4) Biology, No. = Bio, Styryl Group, Derivatives, Derivatives, Gland Derivatives, Styrene Derivatives, Jane A nitrogen derivative, an aniline copolymer, a conductive network molecular oligomer (especially a thiophene oligomer), and the like. 137088.doc -41 - 200936569 As the material for the hole injection layer and the hole transport layer, the above may be used, preferably a ruthenium compound, a fraternal tertiary amine compound, and a phenethylamine compound, especially good. An aromatic tertiary amine compound is used. Further, as the compound having two condensed aromatic rings in the molecule, for example, 4,4,-bis(indenyl-(1-naphthyl)-nonylphenylamino)biphenyl (hereinafter abbreviated as NPD) is preferably used. ), three triphenylamine units are linked into a star-shaped type of 4,4·,4"_three (Ν_(3_methylphenyl)-nonylphenylamino)triphenylamine (hereinafter abbreviated) For MTDATA) and so on. In addition to the above, a nitrogen-containing heterocyclic derivative represented by the following formula can also be used. [化32]

Wherein R to R each represent a substituted or unsubstituted alkyl group having a carbon number of from 1 to 50, a substituted or unsubstituted aryl group having a ring carbon number of from 6 to 50, substituted or not Any one of substituted aralkyl groups having 7 to 5 Å carbon atoms, substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms, R 2 〇 i and R 202, R 203 and R 2 4, R 2 5 and R2〇6, R2〇i and R2〇6, Han 2〇2 and Ruler 203, • or Ruler 2 (>4 and Ruler 2<)5 form a fused ring. Further, a compound of the following formula can also be used. 137088.doc -42- 200936569 [Chem. 33]

R 11 to R216 are a substituent, and preferably, the oxime is an electron attracting group such as a cyano group, a nitro group, a fluorenylcarbonyl group, a difluorodecyl group or a halogen. also? Inorganic compounds such as S1 and P-type SiC can also be used as materials for the hole injection layer and the hole transport layer. The hole injection layer and the hole transport layer can be formed by thinning the above compound by a known method such as a vacuum distillation method, a spin coating method, a cast film method or an LB method. The film thickness of the hole injection layer and the hole transmission layer is not particularly limited, and is usually 5 nm to 5 μηι. The hole injection layer and the hole transmission layer may be composed of one layer containing one or more of the above materials, or may be a plurality of hole injection layers and hole transport layer layers containing different compounds. The electron barrier layer is a layer that enhances luminous efficiency by encapsulating electrons injected from the cathode into the light-emitting layer. In the organic EL device of the present invention, an aromatic tertiary amine compound or the like is used for the compound used for the above hole transport layer. The organic semiconductor layer contributes to the injection of a hole or an electron layer into the light-emitting layer, and preferably has a conductivity of 10 - iQ S/cm or more. As a material of the above organic semiconductor layer, a conductive polymer containing a thiophene oligomer or an arylamine-containing condensate or the like, an electroconductive tree containing an arylamine dendrimer or the like can be used, 137088.doc-43· 200936569 Dendritic polymers, etc. "The electron injection layer and the electron transport layer (electron transport band) are useful for injecting electrons into the layer and transporting them to the layer of the light-emitting region, and the electron mobility is higher, and the electron affinity is larger, usually '25 eV or more. As the above-mentioned electron-m electron transport layer, it is preferable to transfer electrons to the light-emitting layer at a lower electric field strength, and for example, the mobility of the electric field 'Shaw' electrons of igMo6 v/em is at least 1 (r6em2/). v. Second is preferred. ❿ When the nitrogen-containing heterocyclic derivative of the present invention is used in the 9-electron enthalpy band, the nitrogen-containing heterocyclic derivative of the present invention may form an electron injecting layer or an electron transporting layer alone. The material to be mixed with the nitrogen-containing heterocyclic derivative of the present invention to form an electron-incorporated layer or an electron-transporting layer is not particularly limited as long as it has the above-mentioned preferable properties, and can be optionally used. Any of the well-known ones used in the electron-transporting material or the electron-transporting layer of the organic EL element, or the adhesion improving layer is included in the photoconductive material. In the electron injecting layer, in particular, a layer of a material which is preferably adhered to the cathode. In the organic EL device of the present invention, the above-mentioned compound of the present invention is preferably used as an electron injecting layer or an electron transporting layer. In the preferred embodiment of the organic EL device of the present invention, an element containing a reducing dopant is present in a region where electrons are transported or an interface region between a cathode and an organic layer. In the present invention, it is preferable to use the present invention. An organic EL device containing a reducing dopant in the compound of the invention. Here, the reducing dopant is defined as a substance capable of reducing an electron-transporting compound. Therefore, if it is a certain one, it is also required to be 137088.doc 200936569 Various kinds of materials can be used, and the genus, the earth-receiving metal, and the rare earth metal can be preferably used from the oxides of the gold-measuring compound, the earth-measuring metal, the oxide of the test, the oxide of the metal, or the rare earth metal. From the compound of the compound = genus, the organic complex of the rare earth metal, the organic complex of the rare earth metal, and the at least - (tetra) of the test. * The group of organic complexes is more specific. §, as a better ❹ 10 is a work function of 2_9_Τ; #, ^ reducing dopant, especially good enumeration: selected from Na (work function: 2_36 eV), K (work function: 2.28 eV), Rb ( Work function: 2.16 eV) and At least one metal of the group consisting of (force function 1.95 eV); or selected from the group consisting of Ca (work function: 2.9 eV), Sr (work function: 2 〇 25 ridge and _ (force function . 2.52 eV) At least one of the group of soil-measuring metals. Among these, 'better reducing dopants are selected from at least one alkali metal of the group consisting of K, Can and Cs', and preferably Rb and Cs, most Ok,

Cs. In particular, the alkali metal has a high reducing ability, and by adding a small amount to the electron injecting region, the luminance of the organic anal device can be improved and the life can be extended. Further, as a reducing dopant having a work function of 2 9 eV or less, a combination of two or more kinds of alkali metals is preferably particularly preferably a combination containing Cs, such as Cs and Na, yttrium and y, (^ In combination with the ruler 15 or (^ and ^^ and the ruler. By combining the inclusions, it is possible to effectively exhibit the reducing ability, and by adding to the electron injecting region, the luminance of the organic EL element can be improved and the life can be extended. In the present invention, an electron injecting layer composed of an insulator or a semiconductor may be further disposed between the cathode and the organic layer. At this time, the current leakage of the current 137088.doc -45-200936569 can be effectively prevented. As the above insulator, it is preferred to use at least one metal compound selected from the group consisting of a metal chalcogenide, a soil-measured metal chalcogenide, a metal-based compound, and a tooth of a soil-measuring metal. In the case where the electron injecting property can be further improved, it is preferable that the electron injecting layer is composed of the metal molybdenum or the like. Specifically, as the preferred alkali metal chalcogenide, for example, Li2 is exemplified. 〇, K2〇, Na2S And Na2Se and Na2〇' are preferred as the soil-importing metal chalcogenides, and examples thereof include Ca〇, Ba〇, Sr0, Be〇, BaS, and ACaSn as preferred alkali metal tooth compounds, and examples thereof include uf. And NaF, KF, LiC, (10), and (4), etc. Further, as the toothing compound of the preferred earth-receiving metal, for example, a halide other than the fluoride of CaF2, Catch, Call, Mail 2, and (4) may be mentioned. Further, examples of the semiconductor constituting the electron transport layer include: Ca, Sr, Yb, A, Ga, In, Li, Na, Cd, Mg, SiTa, and

The oxide, the nitride or the oxynitride of at least one element of Sb and Zn may be used alone or in combination of two or more. Further, the inorganic compound constituting the electron transport layer is preferably a microcrystalline or amorphous insulating film. When the electron transport layer is composed of the insulating thin films, a more homogeneous thin film is formed, so that pixel defects such as dark spots can be reduced. Further, examples of the inorganic substance include the above-mentioned metal chalcogenide, soil-measuring metal chalcogenide, metal tooth, and alkaline earth metal tooth. As the cathode, a metal having a small work function (4 ev or less), a conductive compound, and a mixture thereof may be used as the electrode material in order to introduce the electron injection layer, the electron transport layer, the light-emitting layer, and the electrons into the electron. 137088.doc -46- 200936569 Specific examples of electrode materials, 7 magnesium can be listed as: nano, nano, unloading alloy,

The electrode materials are formed into a film. , magnesium, lithium, indium, rare earth metals, etc. That is, when the light emitted from the light-emitting layer is taken out from the cathode by vapor deposition or sputtering, the transmittance of the cathode to the light emission is preferably more than 1%. Further, as the sheet resistance of the cathode, it is preferably several hundred Ω/cm or less, and the film thickness is usually from 10 nm to 1 μm, preferably from 5 Å to 2 Å. In the organic EL element, in order to apply an electric field to the ultrathin film, pixel defects caused by leakage or short-circuiting are likely to occur. This is preferable. It is preferable to insert an insulating film layer between the pair of electrodes. Examples of the material used for the insulating layer include alumina, lithium fluoride, lithium oxide, fluorination, oxidized planer, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, and titanium oxide. A mixture or laminate of such cerium oxide, cerium oxide, cerium nitride, boron nitride, molybdenum oxide, cerium oxide, vanadium oxide or the like may also be used. Forming an anode, a light-emitting layer, a hole injection layer as needed, a hole transport layer, and an electron as needed by the materials and formation methods exemplified above

An organic EL element can be produced by injecting a layer and an electron transport layer to form a cathode. Further, an organic EL device can be produced in the reverse order from the cathode to the anode. An example of production of an organic EL device having an anode/hole injection layer, a light-emitting layer, an electron injection layer, and a cathode in this order on a light-transmitting substrate is described below. First, a thin film comprising a % pole material is formed on a suitable light-transmissive substrate by a method such as vapor deposition or sputtering to make it 1 or less, preferably 137088.doc -47·200936569 10~2〇0 The thickness of the film in the range of nm is such that an anode is fabricated. Then, a hole injection layer is provided on the anode. The formation of the hole injection layer can be carried out by a vacuum deposition method, a spin coating method, a cast film method, an LB & method, etc., as described above, and it is easy to obtain a homogeneous film, and it is difficult to produce pinholes and the like. Preferably, it is formed by a vacuum evaporation method. When a hole injection layer is formed by a vacuum evaporation method, the vapor deposition conditions are different depending on the compound to be used (the material of the hole injection layer), the crystal structure of the target hole injection layer, or the recombination structure. Generally, it is preferable to appropriately select in the following range, that is, the evaporation source source temperature is 50 to 450 ° C. The degree of vacuum is 1 〇 - L 10 -3 τ 〇ΓΓ , and the vapor deposition rate i is 0.01 to 50 nm / Second, the substrate temperature is _5〇~3〇〇ΐ, and the film thickness is 5 nm~5 μηι 〇. Then, the formation of the light-emitting layer provided with the light-emitting layer on the hole injection layer can also be formed by the following method: In the organic light-emitting material, the organic light-emitting material is thinned by a vacuum evaporation method, a sputtering method, a spin coating method, a cast film method, or the like, and a homogeneous film is easily obtained, and pinholes and the like are hard to be produced. Preferably, it is formed by a vacuum evaporation method. In the case where the light-emitting layer is formed by a vacuum deposition method, the vapor deposition conditions vary depending on the compound to be used, and it is generally selected in the same range as the hole injection layer. Then, an electron injecting layer is provided on the light emitting layer. The same as the hole injection layer and the light layer, since it is necessary to obtain a homogeneous film, it is preferably formed by a vacuum deposition method. The evaporation conditions may be selected from the same range of conditions as the hole injection layer and the light-emitting layer. The nitrogen-containing heterocyclic derivative of the present invention differs depending on the layer of the light-emitting band or the hole transmission frequency of 137088.doc • 48-200936569, and is made of materials. Further, in the case where it is mixed with other materials, the organic EL element can be obtained by laminating the cathode with its = after. The cathode system is made of metal. In order to prevent the bottom layer of the film from being formed, vapor deposition or sputtering is used. However, in the case of the mineral method, the organic layer of the bottom layer is damaged, preferably by vacuum evaporation.

The organic EL device is preferably produced by working from the anode to the cathode. The method of forming each layer of the organic EL device of the present invention is not particularly limited. A conventionally known method of forming a vacuum vapor deposition method, a spin coating method, or the like can be used. The organic thin film layer containing the compound represented by the above formula (1), which is used in the organic EL device of the present invention, can be formed by a vacuum evaporation method or a molecular vapor deposition method (MBE method). Or a known method of a coating method such as a immersion plating method, a spin coating method, a cast film method, a bar coating method, or a roll coating method, which is dissolved in a solvent. The film thickness of each organic layer of the organic EL device of the present invention is not particularly limited. In general, if the film thickness is too thin, defects such as pinholes are likely to occur, and if it is too thick, a high voltage is required to be applied, and the efficiency is deteriorated. Therefore, it is usually preferably in the range of several nm to 1 μm. Further, when a DC voltage is applied to the organic EL element, when the anode is set to +, the cathode is set to the polarity of -, and a voltage of 5 to 40 V is applied, light emission can be observed. Further, even if a voltage is applied in the opposite polarity, the current does not flow, and no light is generated at all. Further, when the AC voltage is applied, I37088.doc •49-200936569, the luminescence of the first one is observed only when the anode is + and the cathode is -. The waveform of the applied alternating current can be any. EXAMPLES Hereinafter, the present invention will be described in detail using examples, but the present invention is not limited to the examples. Synthesis of Intermediate A1 [Chem. 34]

Intermediate A1 ❹ under a stream of argon in a 300 mL three-necked flask, adding 2__7• worm_9,9-dimethyl·9Η- 20 g (50 mmol), phenylboronic acid 6.6 g ( 54 mmol), tetrakis(triphenylphosphine)|bar (0)1.2 g (l.〇mmol), toluene 2〇〇mL, 1,2-dimethoxyethane 1〇〇mL, 2M sodium carbonate aqueous solution 8 〇 mL, and heated under reflux for 8 hours. After completion of the reaction, water was added, and the precipitated solid was washed with water and further washed with methanol. The obtained solid was recrystallized from toluene-hexane, and purified to obtain 12.0 g of a white powder. The yield was 69%. Synthesis of Intermediate A2 137088.doc -50- 200936569 [Chem. 35]

In the synthesis of the intermediate A1, 1-naphthaleneboronic acid was used instead of the phenylboronic acid, and the same operation was carried out except for the above, whereby the intermediate A2 was obtained. The yield was 55%. Synthesis Example 1 (Synthesis of Compound 1) [Chem. 36]

Add 1-(4-bromophenyl)-2-phenyl-1H-benzene to a 1 mL flask in a 1 mL flask under a stream of argon and sit 3.0 g (8.6 mmol) of dipyridinol. Benzate 2.2 g (8.7 mmol), [1,1,-bis(diphenylphosphino)ferrocene]dichloropalladium (Π) 0.21 g (〇.29 mmol), potassium acetate 2.5 g (25 mmol) , DMF 5 〇 ml 'heated with 80 for 3 hours. After confirming that the raw material bromide disappeared, it was cooled to room temperature. 'Addition of intermediate A1 3.0 g (8.6 mmol), [1,1'-bis(diphenyl scale) ferrocene] digas palladium (Π) 0·21 g (0.29 mmol), 2M sodium carbonate aqueous solution 21 137088.doc -51 - 200936569 mL, and stirred under heating at 80 ° C for 3 hours. After completion of the reaction, water was added, and the precipitated crystals were collected by filtration, washed with water and methanol, and dried under reduced pressure to give a crude product. Purification by column chromatography (silica gel, methylene chloride:hexane) afforded white crystals 2.8 g (yield: 61%). This material was identified as Compound 1 by FD-MS (Field Desorption Mass Spectrometry). Synthesis Example 2 (Synthesis of Compound 2) [Chem. 37]

Intermediate A1

Compound 2 In Synthesis Example 1, 1-(4-bromophenyl)·2·fluorenyl-1H-benzimidazole was used instead of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole. Except for this, the same operation was carried out, whereby Compound 2 was obtained. The yield was 5%. Synthesis Example 3 (Synthesis of Compound 3) [Chem. 38]

Intermediate A1

Compound 3 137088.doc -52- 200936569 In Synthesis Example 1, 5-bromo-1-methyl-2-phenyl-1H-benzimidazole was used in place of 1-(4-bromophenyl)_2-phenyl- Except for this, the same operation was carried out, whereby Compound 3 was obtained. The yield was 45%. Synthesis Example 4 (Synthesis of Compound 4) [Chem. 39]

In Synthesis Example 1, 2-(4-bromophenyl)-indole_methyl_1H_benzimidazole was used in place of 1-(4-bromophenyl)_2-phenyl_1H-benzimidazole, except The same operation was carried out, whereby Compound 4 was obtained. The yield was 40%. Synthesis Example 5 (Synthesis of Compound 5) [Chem. 40]

In the same manner as in the above, the compound 5 was obtained by the same operation as r 4 . Yield is %. Ding phase Synthesis Example 6 (synthesis of compound 6) 137088.doc -53- 200936569 [Chem. 41]

In Synthesis Example 1, the intermediate A1 was used instead of the intermediate A1, and the same operation was carried out, whereby Compound 6 was obtained. The yield was 60%. Synthesis Example 7 (Synthesis of Compound 7) [Chem. 42]

In Synthesis Example 1, except that 1-(4-bromophenyl group, 1st generation is called phenylene)·2·phenyl*benzoxanyl·1Η·benzo benzoate intermediate Ai was used. The phase replaces 7 with the intermediate Α2. The yield was 65%. And, by this, a compound was obtained. Synthesis Example 8 (Synthesis of Compound 8) [Chem. 43]

137088.doc • 54- 200936569 In the first example, the same operation was carried out except that the 2_filling_9,9,_spiro was used instead of the intermediate, thereby obtaining the compound 8. The yield was 70%. Synthesis Example 9 (Synthesis of Compound 9) [Chem. 44]

The same operation was carried out except that 2_bromo-99,_dimethyl_9Η·薙 was used instead of the intermediate Α1' in Synthesis Example 1, whereby Compound 9 was obtained. The yield is 60%. Example 1 (Production of an organic EL device using the compound of the present invention for an electron injecting layer) Glass substrate with a ITO transparent electrode (anode) of 25 mm x 75 mm x 1.1 mm thick in isopropyl alcohol (Geomatec) The company manufactures ultrasonic cleaning for 5 minutes and then UV cleaning for 30 minutes. The cleaned glass substrate with the transparent electrode wire is mounted on the substrate holder of the vacuum evaporation device, firstly forming a film thickness of 60 nm on the side of the side on which the transparent electrode line is formed by covering the transparent electrode N,N,-bis(N,N'_-styl-4-aminophenyl)_n,N-diphenyl-4,4'-diamino-fluorene, ι'_biphenyl film ( The following is abbreviated as "TPD232 film"). The TPD232 film functions as a hole injection layer. After forming the TPD232 film, a 4,4,-bis[Ν-(p-naphthyl)-fluorenyl-phenylamino]biphenyl film having a film thickness of 20 nm was formed on the ΤΡ〇232 film (to 137088.doc-55). - 200936569 is abbreviated as "NPD臈"). That! The film functions as a hole transport layer. Further, on the NPD film, the underlying ethylene derivative (DPVDPAN) of the underlying 7 α 1 and the present ethylene amine derivative (S1) are 40. ο - 4〇. The film thickness ratio of 2 is formed into a blue light-emitting layer at a film thickness of 4 〇 nm. [化45]

On the film, the compound (1) was formed into a film at a film thickness of 20 nm by vapor deposition to obtain an electron transport layer. Thereafter, LiF was formed into a film with a film thickness of i nm. The metal A1 was vapor-deposited on the LiF film at 150 nm to form a metal cathode, thereby forming an organic EL light-emitting element. [Example 2] In Example 1, an organic EL device was produced in the same manner except that the compound (3) was used instead of the compound (1). (Example 3) An organic EL device was produced in the same manner as in Example 1 except that the compound (4) was used instead of the compound (1). [Example 4] An organic EL device was produced in the same manner as in Example 1 except that the compound (7) was used instead of the compound (1). 137088.doc -56-200936569 Example 5 An organic EL device was produced in the same manner as in Example 1 except that the compound (8) was used instead of the compound (i). [Example 6] An organic EL device was produced in the same manner as in Example 1 except that the compound (9) was used instead of the compound 〇). Comparative Example 1 An organic EL device was produced in the same manner as in Example 1 except that the following compound A was used instead of the compound (1) described in International Publication No. WO 2004/080975 A1. [Chem. 46]

Comparative Example 2 An organic EL device was produced in the same manner as in Example 1 except that the following compound B was used in place of the compound (J) in the above-mentioned Japanese Patent Laid-Open Publication No. Hei No. 2-38141. 137088.doc -57· 200936569 [Chem. 47]

Comparative example 3

An organic EL device was produced in the same manner as in Example 1 except that Alq (aluminum complex of 8-hydroxyquinoline) was used instead of the compound (1). Evaluation of Organic EL Element The organic EL elements obtained in the above Examples 1 to 6 and Comparative Examples 1 to 3 were measured for light emission luminance, luminous efficiency, and chromaticity under the conditions of applying a DC voltage as described in Table 1 below. , observe the luminescent color. The results are shown in Table 1. [Table 1] Table 1 Compound voltage of electron injection layer (V) Current density (mA/cm) Luminance (cd/m2) Luminous efficiency (cd/A) Luminescent color Example 1 Compound (1) 5.1 10.0 758.1 7.58 Blue Example 2 Compound (3) 5.4 10.0 746.6 7.47 Blue Example 3 Compound (4) 4.9 10.0 792.0 7.92 Blue Example 4 Compound (7) 5.4 10.0 723.6 7.24 Blue Example 5 Compound (8) 5.1 10.0 750.0 7.50 Blue Example 6 Compound (9) 5.3 10.0 742.3 7.42 Blue Comparative Example 1 Compound A 6.1 10.0 622.9 6.23 Blue Comparative Example 2 Compound B 5.6 10.0 612.1 6.12 Blue Comparative Example 3 Alq 6.2 10.0 480.3 4.80 Blue 137088. Doc-58-200936569 The result of Table 1 shows that an element having a high luminance and a high electron-emitting rate can be produced by using the 4-membered heterocyclic-derived electron-injecting layer of the present invention. [Brief Description of the Drawings] Fig. 1 is a schematic cross-sectional view showing the organic electricity of the present invention. Better layer composition of the light-emitting element [Description of main component symbols]

1 Organic EL element 10 Cathode 20 Anode 31 Hole injection layer 32 Hole transport layer 33 Light-emitting layer 34 Electron injection layer

137088.doc -59-

Claims (1)

200936569 X. Patent application scope: A nitrogen-containing heterocyclic derivative [Chemical 1] organism, which is represented by the following general formula (1) In the formula (1), R1 to R6 are each independently an amino atom, a substituted or ring carbon number of 2 valences of 1 to 5 GU groups, substituted or unsubstituted, argon, rG ring alkyl, substituted Or unsubstituted carbon number / group, substituted or unsubstituted ring carbon number 6~20, substituted or unsubstituted heteroaryl group having 5~2G ring atoms, From the substituted or unsubstituted group, the nitrogen sulphate is substituted for 'atoms, cyano groups or nitro groups; the adjacent two groups of R 丨 R R6 may also be bonded to each other' to form a substituted or unconstituted ring structure. a substituent which is saturated or not bonded to 2; and at least i of 'r1 to r6 is a group derived from a fused ring compound represented by the following formula (7), [Chemical 2] (In the above formula (2), 'Ru~RlGa^_ is a substituted or unsubstituted ring having a carbon number of 6 to 6 G, substituted or not taken 137088.doc 200936569 =ΠΓ60 An aryl group (except for a hetero-W group substituted or unsubstituted), a substituted or unsubstituted alkyl group of 1 to 50, a ruthenium ruthenium + a ruthenium octacarbonate The number is 3 to 5 〇 = di-base, and 2 (four) 'forms a substituted or unsubstituted saturated or unsaturated linking group constituting the ring structure). The nitrogen-containing heterocyclic derivative of claim 1, wherein the compound represented by the above formula (1) is a compound represented by any one of the following formulas (3) to (5). ] In the above formulas (3) to (5), RI to R6 are the same as described above, and several are groups derived from the above-mentioned ring compound. A material:: or a nitrogen-containing heterocyclic derivative of 2, which is a gas-containing heterocyclic derivative of an organic electroluminescence device: a system, an organic electroluminescence element injection material or an electron transport material . 5. For the item 1 or 2, use a luminescent material. #晨衍生, which is an organic electroluminescent element 6. an organic electroluminescence noiy with a luminescence between the cathode and the anode 137088.doc 200936569 2 two layers from the upper organic thin film layer 'the above organic thin film I, 1 or 2 contains a mixture of impurities - a layer having an electron injecting layer or an electroless organic film layer 8. The transport layer contains the above gas-containing heterocyclic derivative, the electron injecting layer or the electron such as the organic electric material of the item 6 The organic electroluminescent device of the above-mentioned electron-injecting layer containing 9. SSI, wherein the electron-injecting layer further contains a reducing dopant. 10. The organic electroluminescent device according to claim 9, wherein the reducing dopant is selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal compound, an alkaline earth metal oxide, One or two of a group consisting of a tooth of an alkaline earth metal, an oxide of a rare earth metal, a compound of a rare earth metal, an organic compound of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal More than one species. 137088.doc