TW200910664A - Organic electroluminescent element and material therefor - Google Patents

Abstract

This invention provides a phosphorous organic electroluminescent element capable of realizing an emission peak by electroluminescence in a deep blue color region below the wavelength of 440 nm which is essential for completing a full color display. The organic electroluminescent element of this invention has a light emitting layer or a plurality of thin layers of an organic compound containing a light emitting layer in between a pair of electrodes, and is characterized in having a phosphorous electroluminescent emission peak at a wave length of 440 nm or below, more particularly having a maximum peak of phosphorous electroluminescent emission in a deep blue color region at the wavelength of 440 nm or below, and the color of the emitted light is of a value of y ordinate of less than 0.180 according to the color chart of CIE.

Description

200910664 IX. Invention Description: [Technical Fields of the Invention] Two kinds of organic electroluminescent elements (electric field illuminators:,,,,,,,,,,,,,,,,,,,,,,,,,,,, Luminous element ^^峰^ = Organic electroluminescence of the present invention == Kissable is only a useful element for completing a full-color display. [Prior Art] In recent years, the use of organic electroluminescent elements (organicectect〇iuminescent heart (10), although Pay attention to its application to the display device for high-performance flat color display, but the luminescent material is mainly used to use the fluorescent material that emits light from the excited single element of the luminescent molecule, and expands the use of triple weight in order to obtain higher materials. An excimer-emitting phosphorescent material. However, in a spheroidal organic electroluminescent device, it is necessary to produce a bi-peak element having electroluminescence in the deep blue region below 44 Gnm which is important for a full-color display. It is also necessary to make a giant peak of phosphorescence in the deep blue field below 440 nm, and the luminescent color is on the color of the International Illumination Commission. It is considered that it is very difficult to use a component with a value of less than 0.180 (see, for example, Non-Patent Document 1) Non-Patent Document 1: A Summary of the Speech of the "2006 Organic EL Seminar", 苐7 ((Social) Southern Molecular Society SUMMARY OF THE INVENTION [Problems to be Solved by the Invention] The subject of the present invention is to manufacture a disc-light organic electroluminescent device 320302 5 200910664 in order to complete an important deep blue field below the 44-inch surface of a full-color display. An element that can illuminate the illuminating peak of electroluminescence, and is in the deep blue field below the wavelength = the maximum illuminating peak of the luminescence, and the color of the luminescent color in the CIE (International Commission on Illumination) is not up to Element of 0.180. (Means for Solving the Problem) The object of the present invention can be solved by an organic electroluminescence device, in which an organic light-emitting layer or an organic layer of a plurality of organic material layers including a light-emitting layer is formed between electrodes. A light-emitting element having a characteristic of a phosphorescent electroluminescence having a wavelength of 44 or less. The second item of the present invention relates to an organic electroluminescence element. An organic electroluminescence device characterized by a thin layer of two organic compounds including a hairpin or a light-emitting layer between the electrodes and having a light-emitting wave having a wavelength of 44 Q nm or less. Further, the present invention The second item, the different you _ # + ,, is a deep blue two-f electro-luminous element below 44 〇nm, and the illuminating color is in the International Commission on Illumination (Xi Xi Gu Da 0.180.) The y coordinate value is not the third item of the present invention, and is related to an organic _ containing a compound or a plurality of bismuth compounds in the luminescent layer, and the fourth item of the present invention is related to a general formula of a money compound in an organic material. (1) The wrong compound represented by 'the 320302 6 200910664

GeR4R5R6 (In the above formula, L is 0 to 2, and k is an integer of 0 to 3. R1 or R6 may be the same or different and are alkyl, cycloalkyl, alkenyl, aralkyl, aryl, heterocyclic Or an alkoxy group or an aryloxy group. Further, any hydrogen atom of these groups may be a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aromatic group, an aralkyl group, an alkoxy group, an aryloxy group, an alkylthio group, The arylthio group or the organodecyl group is substituted. Further, R1 or R6 may be bonded to each other to form a ring, and the bond group which is bonded to form a ring may be a single bond, an ether bond, a thioether bond, a stretching group, or an oxygen-expanding group ( Oxylalkylene), or thioalkylene. X is alkyl, cycloalkyl, alkenyl, aryl, aralkyl, alkoxy, aryloxy, alkylthio, arylthio or substituted The amine group of the present invention relates to an organic electroluminescence device, wherein the oxime compound is a erroneous compound represented by the general formula (1a).

(K, X, and R1 and R6 in the above formula are synonymous with the above.) The sixth aspect of the present invention is an organic electroluminescence device, wherein the oxime compound is an oxime compound represented by the following formula (2): 320302 200910664

(In the above formula, 1 is the number of kings of 〇 to 2, the integer of m疋i to 3,] 1 is an integer of 2 to 3, and k is synonymous with the above. θ #土# 戮Α is the same as or a different aryl or heterocyclic aryl group, and any hydrogen atom of this meili ^ ^ diyl group can be used as an atom, a group, a sulfhydryl group, a aryl group, an aromatic group, an aryl group, an aromatic group. Substituted by a dairy group, a thiol group, an arylthio group, or an organic material group. Further, Ar may be substituted by a homo-and a wrong atom, and the adjacent arsenic of Ar may be via a single bond. , ether bond, bond: two: I, or sulfur extended alkyl group to combine. X, R is fluorenyl, ^ group, unloading group, cycloalkyl, alkoxy or aryloxy. X is the same as the above ) caused "pieces -

同 Synonymous with the foregoing. An organic electroluminescence device, wherein (in the above formula, k, m, n, X, Ar, and R_, the eighth item of the present invention is related to a 320302 200910664

Indole compound represented by general formula (2b)

(In the above formula, k, X, and Ar are synonymous with the above.) The group of (4) from the following materials (lG), the compound of the material, at least one compound of the group T:

The ninth item is an organic electroluminescence device, and the first aspect of the invention relates to a case where the luminescent layer contains a plurality of quinone compounds. Electromechanical luminescent element, its 200910664 井井屌:;^弟的弟11 item is an organic electroluminescent element, which has a single type or a plurality of substituents represented by the formula Y-

-AuL (3) (In the above formula, L is a nitrogen-containing heterocyclic carbon-mixed aromatic group, aralkyl Y is a pit group, a nucleus group, a clothing group. One or a Y carbon atom is also: (4) The original +, burnt base, er, dilute base, aromatic earth side, meta-alkoxy group, aryloxy group, di-burning aryl group are replaced. Also, γ 夕石山店工 L # Α 况 基 或 或 或 或 或 或 或A plurality of hydrogen atoms on the diatomic atom may be substituted by a dialkyl group, an alkoxy group, an aryloxy group or a dialkylamine green group, and the groups of the phases are bonded to each other to form a ring. Item 12 relates to an organic electroluminescence device which is a two-hole transport layer, and the hole transport layer is a compound containing one or more substituents represented by the following formula to constitute a different compound.

"4) (In the above formula, 'Z is a mono- or complex filament, a thiol, an aromatic, an aromatic or a heterocyclic group. One or a plurality of hydrogen atoms on the carbon atom of X, Z, also y Atom, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, methoxy, aryloxy, hexaamino, carbohydrase, carboaryl or organolithium 320302 10 200910664 alkyl Substituted.) (Effects of the Invention) According to the first, third, and fourth aspects of the present invention, it is possible to use an organic electroluminescence device and a component of the organic electroluminescence device. The material, the organic electroluminescent element is at a wavelength of 44 〇 nm or less. (IV) The organic electroluminescence element of the invention of the photoluminescence peak, for example, is a useful element for achieving the completion of a full-color display. Piece ^, Ming 2nd, 6th 'can realize the organic electroluminescent element' which is important in completing the full-color display at the wavelength of (5) below == domain scaly photoluminescence, the maximum luminescence peak, and its The illuminating color is in the CIE (International Commission for Lighting) 矣耷糸. The female 曰 曰 曰 录 录 y 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 180 Or an organic electroluminescent first 7C piece having a number of luminescent layers and having a # n ^ θ organic σ 溥 layer is characterized by a light peak. Ϋηιη below the phosphorescent electroluminescence of the organic electroluminescent device represented by the wrong compound: the bismuth compound is - (1)

[GeR1R2R3 j A (υ

GeR4RsRe (wherein L 疋 0 to 2, preferably, or 2, and k is an integer of 320302 11 200910664 of Q to 3. R or R may be the same or different 'as a burning group, a ring-based group, an alkenyl group , an aralkyl group, an aryl group, a heterocyclic aryl group, an alkoxy group or an aryloxy group. Further, any hydrogen atom of these groups may also be a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aromatic group or a cycloalkyl group. Substituted by an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group or an organodecyl group. Further, R or R6 may be bonded to each other to form a ring, and the bond group which is bonded to the oxime may be a single bond. An ether bond, a thioether bond, an alkylene group, an oxygen-extension group, or a sulfur-extension group. X is an alkyl group, an alkenyl group, an aromatic group, a cycloalkyl group, an alkoxy group, an aryloxy group, or an alkane group. A thio group, an arylthio group or a substituted amine group.) Preferred is an anthracene compound represented by the general formula (la):

(In the above formula, k, X, and Ri and even R< 锗 compounds represented by the general formula (lb): and even R6 are synonymous with the above.) More preferably,

And Ar2 may be the same or (in the above formula, k and X are an aromatic or heterocyclic aryl group which is different from the above-mentioned synonymous 320302 12 200910664. Further, any hydrogen atom of the aromatic group may also be abbreviated atom, alkyl group, Substituted by a cycloalkyl group, an alkenyl group, an aryl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group. Further, Ar and Ar may be bonded to each other to form a ring, which is combined into The bonding group of the ring may be an ether group, a thioether group, an alkylene group, an oxygen-extension group, or a sulfur-extension group.) Further, these onium compounds may be used singly or in combination of two or more kinds. In the above general formula (1), L is preferably 〇 to 2, 丨 or 2 is preferable, and k is an integer of 〇 to 3, but when 1 is 1, it is a compound of the general formula (1&). R1 or R6 may be the same or different and may be an alkyl group, a cycloalkyl group, a county, an aromatic group, an aromatic group, a heterocyclic aryl group, a (tetra) group or an aryloxy group. '一----~ six from the number of turns 1 to 12 is better', for example: methyl, ethyl, propyl, butyl, pentyl, shovel, carbon number, octyl, oxime The radicals, thiol groups, and some substituents also include isomers thereof. _Alkyl, dodecyl and the like. Further, the cycloalkyl group is preferably a cycloalkyl group having 5 to 8 carbon atoms, and examples thereof include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. The aforementioned dilute group is preferably a carbon number of 2 to 20, particularly a dilute group of 2 to 12, and examples thereof include an ethyl group, a propenyl group, a butenyl group, a pentane (tetra), a hexyl group, a gypsum, a xinxian, and a guanidine. Jobs, dereliction of duty, ten-county and twelve rare bases. Further, these substituents also include isomers thereof. The above-mentioned aryl group is preferably an arylene group of from 7 to 2 G, and examples thereof include 320302 13 200910664 such as a benzyl group, a naphthyl group, an anthracenyl group and a biphenyl fluorenyl group. The above aromatic group is preferably an aromatic group having 6 to 12 carbon atoms, and examples thereof include a phenyl group, a tolyl group (and an isomer thereof), a diphenylmethyl group (and an isomer thereof), and a naphthyl group (and the same) The structure), and the dinonylnaphthyl group (and its isomers) and the like. The above heterocyclic group is preferably a carbon number of 4 to 10, and may be a thiol group, a phenylthio group, a ratio of 7 groups, a 11 m α group, or a ruthenium group. Than π-based, sulfhydryl, sputum-based, cylinyl, iso-decyl, hydrazine. Take quinazolyl, quinoxalyl, etc. The alkoxy group is preferably an alkoxy group having 1 to 10 carbon atoms, and examples thereof include a decyloxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, and a heptyloxy group. Octyloxy, decyloxy, decyloxy and the like. Further, these substituents also include isomers thereof. The aryloxy group is preferably an aryloxy group having 6 to 14 carbon atoms, and examples thereof include a phenoxy group, a nonylphenoxy group, a diphenoxy group, a naphthyloxy group, and a dimethylnaphthyloxy group. Further, these substituents also include isomers thereof. Further, R1 or R6 represented by the general formula (1) may have any hydrogen atom which may be derived from a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aromatic group, a cycloalkyl group, an alkoxy group, an aryloxy group or an alkylthio group. Substituted by an arylthio group or an organodecyl group. The halogen atom may, for example, be a fluorine atom, a chlorine atom, a desert atom or an iodine atom. The alkyl group, the ring-based group, the dilute group, the aryl group, the cycloalkyl group, the alkoxy group and the aryloxy group are synonymous with the groups exemplified in R1 to R6. The sulfur-burning group is preferably a sulfur-burning group having 1 to 6 carbon atoms, such as an anthracenethio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group or a hexylthio group. Again, these 14 320302 200910664 substituents also contain isomers thereof. The above arylthio group is preferably an arylthio group having 6 to 14 carbon atoms, and an alkyl group, a T phenylthio group, a xylylthio group and a naphthylthio group. Also included are their isomers. The above-mentioned organic money base is preferably an organic group having a carbon number of 3 to 18, such as an alkyl group, a dimethylethyl (tetra) group, a triethyl group, a dipropyl (tetra) group, a tributyl (tetra) group, Phenyl dimethyl fluorenyl and the extract - methyl sylvestre base and the like. Further, these substituents also include isomers thereof. In the community, R1 and R6 can be combined into a ring, which combines into a ring, , and . ^ can be a single bond (the state in which RI or r6 is directly bonded), an ether bond (8) or even a state in which R is directly bonded via oxygen), a sulfur sequence (a state in which r1 or V is directly bonded via sulfur), a light base, and an oxygen extension Base, or sulfur stretched wire. The above-mentioned stretching group is preferably a stretching group having a charcoal number of 1 to 4, and examples thereof include a methylene group, an ethyl group, a propyl group and a butyl group. "Others are based on the oxygen number i to 5 oxygen extension base, can be = methyl, oxygen extended propyl, oxygen butyl, oxygen extended Wuya. methyl, oxyhexazone , a methylene methyl group, a dioxet propyl group, a dioxet butyl group, a dioxypentamethylene group f dioxomethylene group, and the like. Also, these substituents also contain isomers thereof. The sulphur-extension base is preferably a sulphur-extension group having a carbon number of i. to 5, and may be exemplified by methylene, thiopropyl, thio-butyl, thiopentamethylene, or hexa-": Thiomethylidene, dithio-propyl, dithio-butyl, dithiopenta-methyl, dithiohexamethylene. Further, these substituents also contain isomers thereof. , alkenyl, arylalkyl, alkoxy, cubic, thiol' arylthio or substituted amine, and alkyl, ring 320302 15 200910664 alkyl, alkenyl, aryl, ring The alkyl group, the alkoxy group and the aryloxy group are synonymous with the groups exemplified for R1 to R6. The above alkylthio group is preferably an alkylthio group having 1 to 6 carbon atoms, and examples thereof include a methylthio group and an ethylthio group. Further, propylthio, butylthio, pentylthio and hexylthio. Further, these substituents also contain isomers thereof. The carbon number of the above arylthio group is preferably an arylthio group of 6 to 14, such as benzene. a thio group, a tolylthio group, a xylylthio group, a naphthylthio group, etc. Further, these substituents also include an isomer thereof. The above-mentioned amine group having a substituent is preferably a substituted amino group having 1 to 14 carbon atoms. For example, amidino group Ethylamino, propylamino, butylamino, dimethylamino, diethylamino, dipropylamino, anilino, anthranilyl, xylylamino, naphthylamino, benzoguanamine, phenethylamino And a diphenylamino group, a dinonylanilino group, a bis(nonylanilinium) group, etc. Further, these substituents also include an isomer thereof. When R1 or R6 is an aromatic group or a heterocyclic group, it becomes the above general formula ( The compound of lb), wherein Ar1 and Ar2 in the general formula (lb) may be the same or different aryl or heterocyclic group, and any hydrogen atom of the aryl group may be a halogen atom, an alkyl group or a ring. Substituted by an alkyl group, an alkenyl group, an aryl group, an arylalkyl group, an alkoxy group, an aryloxy group, an alkylthio group or an arylthio group.

Ar1 and Ar2 may be bonded to each other by a ring, and the bond group bonded to the ring may be an ether group, a thioether group, an alkylene group, an oxygen alkyl group, or a sulfur alkyl group. These are synonymous with those of R1 and R6. Specific examples of the ruthenium compound of the present invention include, for example, the general formula (lc) to '(lg): 16 320302 200910664

The hydrazine compound shown can be suitably used to contain a plurality of species. In the case of the luminescent compound, the ruthenium compound of the present invention is desired in the luminescent layer, and the starting material is placed in the "sub-group" = the ruthenium halide compound is used as the oral substance (for example, refer to Non-Patent Document 2)." Non-Patent Document 2: Japanese Chemistry Journal, vol. 84, ΐ 963, milk second, the ideal organic electroluminescent device of the present invention, which forms a light-emitting layer or a plurality of layers of organicized persons including a light-emitting layer between one and two electrodes, An electroluminescent device characterized by being in the range of 44 〇 nm or less, the field has a large luminescence peak of electroluminescence, and the y-coordinate value of the luminescent color in the CM Ming (CIE) color system is less than 〇. 丨 8 Hey. The element has a single compound or a substituent in the light-emitting layer to constitute a compound of the general formula (2): 320302 17 200910664:

(In the above formula, 1 is an integer of 0 to 2, m is an integer of 1 to 3, n is an integer of J to 3, and k is an integer of 〇 to 3. Ar is an aromatic group or a heterocyclic group, which may be The same or different, any of the hydrogen atoms may also be halogen atoms, alkyl groups, cycloalkyl groups, alkenyl groups, aromatic groups, aralkyl groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, Substituted with an amine group or an organic sulfonium group. Also, 'different Ar can be substituted by the same argon atom, but the total number of different ar groups is equal to m. The adjacent Ar can also be via a single bond, An ether bond, a thioether bond, an alkylene group, an oxygen alkyl group, or a sulfur alkyl group. Further, R is an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an alkoxy group or an aryloxy group. X is an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an arylalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group.) 'When the above Ar is an aromatic group, The carbon number is preferably from 6 to 14, and examples thereof include a phenyl group, a naphthyl group, a phenanthryl group and a ketone group. When Ar is a heterocyclic group, it is preferably a carbon number of 4 to 1 Å, and examples thereof include a ?anyl group, a phenylthio group, a pyrrolyl group, an imidazolyl group, an oxazolyl group, a pyridyl group, a thiol group "(tetra) group, Any hydrogen atom of a sulfonyl group or a heterocyclic group of a ruthenium group or a heterocyclic group may also be derived from a ruthenium atom, 320302 18 200910664 alkyl, cycloalkyl, alkenyl, aryl, aralkyl Substituted by a group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, a substituted amino group or an organic decyl group, and the adjacent Ar may be directly bonded by an ether bond or a thioether bond, or via The alkyl group, the oxygen alkyl group or the sulfur alkyl group is bonded. a halogen atom, the above-mentioned alkyl group, the above-mentioned cyclic group, the above-mentioned rare group, the above aromatic group, the above-mentioned aryl group, the above-mentioned alkoxy group, the above aryloxy group, the above-mentioned sulfur-burning group, the above-mentioned arylthio group, and the above-mentioned substituent The amine group, the above organic sulfonium group, the aforementioned alkylene group, the oxygen-extension group, and the sulfur-extension group are synonymous with the above. The above-mentioned alkyl group, cycloalkyl group, dilute group, aryl group, aryl group, alkoxy group, aryloxy group, alkylthio group and arylthio group, and an alkyl group or an alkylene group which is bonded to an adjacent Ar And a sulfur alkyl group, and the hydrogen atom bonded to the carbon atom may be further substituted by a halogen atom, an alkyl group, an alkenyl group, an aromatic group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group or a nitro group. Substituting a cyano group or a diamined amine group. These substituents may be the same as those defined by Ar described above. The above R is an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an alkoxy group or an aryloxy group. These may be the same as the substituents defined by Ar described above. The above X is synonymous with the foregoing. The ruthenium compound represented by the formulas (1) and (2) contained in the organic electroluminescence device of the present invention can be, for example, according to Non-Patent Document 1, and the formula (6), (7) or (8) The organometallic compound represented by the reaction is synthesized by reacting with an organic phosphonium chloride (formula (5)) (for example, refer to Non-Patent Document 2). (Ar ten Ge~(-GI)4_j (1) 19 320302 200910664 (In the above formula, j is 0 to 3 Ar - Μ (In the above formula, Ar is the same as the aforementioned chlorine, bromine or iodine.) R — Μ integer 'Ar Synonymous with the above.) (6) 义' Μ is Li or MgY. Here Y is (7) (In the above formula, 'R is synonymous with bromine or A or MgY. Here, ¥ is chlorine, <fe) 匕Wherein X is synonymous with the above, and 丨 is 2 to 3 3 Μ is U or MgY. Here, 丫 is synonymous with the foregoing.) The compound having a positive number of 2 is exemplified by, for example, the above-mentioned compound called electroluminescent element. - seed-to-electrode machine: a thin layer of organic compounds in a layer of light-emitting layer; ^electrically characterized by a dark blue field below 440 nm 3 = an illuminating peak of electroluminescence, ideally below 44 Gnm The depth of the color _ color domain has a phosphorescent photoluminescence pole 廿 丄 丄 & & & 照明 照明 照明 照明 照明 照明 照明 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从 从The value is less than G.18G, which is more reasonable. 疋 The luminescent layer contains one or more kinds of wrong compounds... ^ Again, the organic electroluminescent ride of the present invention, the type is in - two = luminescent layer or contains hair The plurality of layers of the organic compound thin laminate element 'm layer including the above formula (1) or (2) is characterized by two or a plurality of different substituents. The organic compound layer is a light-emitting layer. The electron injection layer or the 320302 20 20〇9l〇664 feed layer, the compound represented by the above formula (1) and the compound or a plurality of ruthenium compounds, or the above-mentioned formula into the layer or the hole transport layer, may also contain In the electron injection outside the luminescent layer, the luminescent layer of the T compound of the above formula (1) or the main __ _ organic compound layer is added, and the organic electric cup of the present invention is 2 to 2 98% by mass is preferred. The doping material and hole injection can be formed by using a luminescent material, a hole injecting layer, a luminescent layer, a ==into material, and a constituent layer. At this time, ^ can also be respectively 2 The layer above the layer is called the hole injection reed, and the child is injected into the layer, and the injection layer from the electrode injection hole to the luminescent layer receives the hole and the electricity s is called the hole transport layer. Similarly, Electron injection two layers of electrons injected into the electrodes are called electron injection layers, and are injected by electrons. The layer that forks electrons and transports electrons to the light-emitting layer is called an electron wheel. The layers are selected according to various factors such as the energy level of the material, the heat of the material, the adhesion to the organic compound layer or the metal electrode. σ is used in the material of the light-emitting layer together with the ruthenium compound represented by the above general formula (1) or (2), and needs to be added in order to obtain light-emitting luminescence, and phosphorescence electroluminescence is below 440 nm. In the case of the above-mentioned examples, a group of ligands represented by a well-known document (see, for example, Patent Document 1, Non-Patent Document 3) And 4). Patent Document 1: International Publication W02006-8〇515 Booklet Non-Patent Document 3: "2006 Organic EL Seminar" Speech Summary, Page 7 (Social Polymer Society) 320302 21 200910664 Non-Patent Document 4: Inorganic Further, among them, a compound group represented by the following formula described in Patent Document 1 can be suitably used. Y-^==^=- — AuL (3) (In the above formula, L is a nitrogen-containing heterocyclic carbene ligand. γ is an alkyl group, a cycloalkyl group, an aromatic group, an arylalkyl group, or a heterocyclic group. Further, one or a plurality of argon atoms on the Y carbon atom may be halogen atoms, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, alkoxy groups, aryloxy groups, dioxane groups. Substituted by an amine group, a carbon alkyl group or a carbon aryl group. Further, a plurality of hydrogen atoms on the carbon atom of Y are alkyl, alkenyl 'aryl, aralkyl, alkoxy, aryloxy, dioxane In the case where the amino group, the carbon alkyl group or the carbon aryl group is substituted, the adjacent groups may be bonded to each other to form a ring.) Further, the luminescent material may be added with a luminescent material or a main matrix material, and various carbazoles may be used. Carbazole derivatives, condensed polycyclic aromatics (anthraquinone, naphthalene, phenanthrene, pyrene, tetracene, pentacene, coronene, chrysene) ), fluorescein, perylene, rubrene and its derivatives, phthaloperylene, naphthaloperylen e), perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin Coumarine), oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pypyazine, cyclopentadiene, Molecular ligand, 22 320302 200910664 Aminoquinoline metal ligand, benzylquinoline metal ligand, quinolylacetylene metal ligand, quinoxalylacetylene Metal ligand, quinazolylacetylene metal ligand, imine, stilbene, vinylanthracene, diaminocarbazole, pyrane, bowl π-pyran (thiopyrane), polymethine, merocyanine, oxinoid compound, quinacridone, red fluorescein, stilbene Derivatives and fireflies Light pigments, etc. Among the known hole injecting materials which can be used in the organic electroluminescent device of the present invention, the more effective hole injecting material is aromatic tertiary amine derivatives or phthalcyanin derivatives. ). The above-mentioned aryl tertiary amine derivative may, for example, be triphenylamine, trimethylamine, decylphenyldiphenylamine, anthracene, fluorene, or diphenyl-N,N'-(3-methylphenyl)-1, fluorene- Biphenyl 'yl-4,4,-diamine (hereinafter abbreviated as TPD), hydrazine, hydrazine, hydrazine, hydrazine, -(4-methylphenyl)-1, fluorene-phenyl-4,4,- Diamine, hydrazine, hydrazine, hydrazine, hydrazine, -(4-methylphenyl)-1,1'-biphenyl-4,4,diamine, anthracene, fluorene,-diphenyl-fluorene, Ν'- Dinaphthyl-1,1'-biphenyl-4,4'-diamine, anthracene, Ν'-(methylphenyl)-indole, Ν'-(4-n-butylphenyl)-phenanthrene An oligomer or polymer having the aryl-9,10-diamine, 1,1-bis[4-(di-4-indolylphenyl)phenyl]cyclohexane, etc. or having these aromatic triamine backbones Things, but not limited to these. The aforementioned phthalocyanine (Pc) derivative may, for example, be H2Pc, CuPc, CoPc,

NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, CIGaPc, CllnPc, CISnPc, Cl2SiPc, (HO)AlPc, (HO)GaPc, VOPc, TiOPc, 23 320302 200910664

The phthalocyanine derivative or the naphthalocyanine derivative of MoOPc, GaPc-O-GaPc or the like is not limited thereto. The specific form of triphenylene derivatives can be expressed by the following formula.

(In the above formula, Z is a single or plural alkyl group, a cycloalkyl group, an aryl group, an arylalkyl group or a heterocyclic group. Further, one or a plurality of hydrogen atoms on the carbon atom of Z may also be derived from an i atom, Substituted by alkyl, cycloalkyl, alkenyl, aryl, aralkyl, alkoxy, aryloxy, dialkylamino, anthracenyl, carboaryl or organocycloalkyl. Examples thereof are the same as those defined above as Ar.) Among the organic electroluminescent elements of the present invention, a more effective known electron injecting material is a metal complex compound or a nitrogen-containing five-membered ring derivative. The metal complex compound may, for example, be lithium quinolate, bis(8-carboxylic acid) zinc, bis(8-carboxylic acid) copper, or bis(8-fluorenyl) manganese. Aluminum tris(8-hydroxyquinolinate) (hereinafter slightly Alq3), aluminum tris(2-indolyl-8-hydroxyquinolinate), tris(8-fluorene-sulphuric acid) gallium, bis(10-benzyl group) [h] 啥 酸 acid) bismuth, bis (10-benzyl [h] quinolinate) zinc, bis (2-methyl-8-quinolinic acid) chlorogallium, bis (2-mercapto-8-) Quinolinic acid (o-cresol) gallium, bis(2-methyl-8-quinolinic acid) (1-naphthoic acid) aluminum and bis(2-methyl-8-quinolinic acid) (2-naphthalene) Acid, gallium, etc., but not limited to these. 24 320302 200910664 The aforementioned nitrogen-containing five-membered ring derivative is preferably, for example, a oxazolidine, a thiazole or a triazole derivative. Specific examples include: 2,5_bis (1_phenylindole, 3,4 anthraquinone, dimethylpopop (here P0P0P is a kiwi) benzene.), 2,5_double 2, 5 (1), 1,3,4-σ oxadiaz〇ie, 2_(4,_tris-butylphenyl)5-(4"-biphenyl fluorene, 3,4·11 oxadiazole, 2,5-bis(1_naphthyl ρ, κ oxadiazole, 1,4 bis[2-(5-phenyloxadiazolyl)]benzene, 14-double [2_(5-phenyl broad-oxadiazolyl)-4·tertiary-butylbenzene], 2_(4,_tris-butylphenylbiphenyl)-1,3,4-thiadiazole , 2,5_bis(1_naphthyl)_1,3,4-thiadiazole, 1,4_bis[2-(5-phenylthiadiazolyl)]benzene, 2_(4,-third-order- Butylphenyl)_5_(4,,_biphenyl)-1,3,4-triazole, 3-(4-diphenyl)-4-phenylene-5-tertiary-butylphenyl_1, 2,4-triazole, 2,5-bis(]-naphthyl)-1,3,4-triazole and l,4-bis[2-(5-phenyltrisyl)]benzene, etc. In the organic electroluminescence device of the present invention, an inorganic compound layer may be provided between the light-emitting layer and the electrode in order to improve charge injection properties. (The inorganic compound layer may be UF, U2, or Ba). SK), foot 2 and SrF2, etc. Fluoride and oxide of an alkali metal or alkaline earth metal. The conductive material used in the anode of the organic electroluminescence device of the present invention is preferably a work function having a work function of 4 eV or more, such as carbon atom, aluminum, or the like. , iron surface, nickel, crane, silver, gold, platinum, and alloys thereof, ιτ〇 (in addition to 5 to 10% tin oxide in the indium) substrate, tin oxide and indium oxide used in the NESA substrate As the oxidized metal, polythiophene (P〇iyth10Phene) and polyorgano-organic organic conductive resin can also be used. For a conductive material used for a cathode, a work function of less than 4 eV is 25 320302 200910664. The alloys of town, word, tin, wrong, titanium, Ji, manganese and so on. Here is the combination of ^ = marriage and V, etc. The ratio of alloy is controlled by steam (four) "degree of vacuum", etc., no special In addition, the anode money is extremely necessary if necessary. There are two phases. (IV) The organic electroluminescent device of the present invention is at least one side of the component light-emitting wavelength is ideal for the financial field, and Yu Qianming is Ideal. The transparent electrode is electrically conductive as described above. The material is obtained by a method of setting a vaporized material which can ensure a predetermined light transmittance. The light transmittance of the electrode of the light-emitting surface is preferably 1% or more. The substrate is mechanically and heat-resistant. For example, a glass substrate or a transparent wax film may be used, and the transparent resin film may be, for example, polyethylene, ethylene, or vinyl acetate. WK mouth 'ethylene> Ethyl alcohol copolymer, polythene, polystyrene, polymethyl propyl phthalate, polyvinyl chloride, polyethylene glycol, polyvinyl condensate (polyvinyl Bmyrai), nylon, polyether ketone (PEEK), polysulfonium, polyether oxime, tetrafluoroethylene-perfluoroalkyl ethylene bond copolymer, gas Ethylene, Si Nong ethylene_Ethylene co-polymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, polyvinylidene fluoride resin (PVDF), polyester, polycarbonate Ester, urethane resin, p〇lyimide, polyether amide, and the like. In the organic electroluminescence device of the present invention, in order to improve the stability to temperature, humidity, 26 320302, 200910,664, environment, etc., for example, the entire protective element such as silicone rubber or resin may be used. The surface of the crucible is provided with a protective layer, and the organic electroluminescence element is used for vapor deposition, sputtering, plasma or ion plating (4), for example, a vacuum cloth, dip coating or flow coating, etc. The membrane method, or the rotary coating method, is particularly limited, but the film thickness is . The film thickness does not range from lOnm to 〇.2Am. "111 is preferable, and more preferably, in the case of the above wet film formation, the compound is dissolved or dispersed in, for example, ethanol, and the solvent (di〇X_) represented by the above formula (1) is used. Modulation film; four-wind bite reading or two-drying dry film forming method by vacuum evaporation, set at a vacuum degree of 2χ1 (Γ3 using the real work 瘵 plating in the steaming container (_) in the lower ^ plate temperature At room temperature, it will be placed, and the indicated aroma = 1), () a) or (2) or (2a) can be evaporated to prepare a film. This day: 4, the compound is heated to 'this material You can use a suitable thermocouple to contact the two or two controls: the temperature of the steam source, the 'wire thermometer, etc.. Also, to, x, or non-contact infrared film thickness meter. '', to control the amount of evaporation 'A vapor deposition film thickness gauge suitable for vapor deposition can be used, and the film thickness can be determined by the weight of the film (4) applied to the surface of the vibrator provided with the vapor deposition source. Real time can be used to measure the host material: ^(ΐ)^(2) the compound and the luminescent material, or J /, hot forging, you can use the eight different types of evaporation sources, and can be independently controlled by 320302 27 200910664. The pinholes are organic thin to improve the temperament and prevent the film. Insulating resin for dilute acid, polythene, etc., such as polystyrene, polycarbonate, polypropylene, polypropylene diamine, polyurethane, polysulfone, polymethacrylic acid f or cellulose Or the photoconductivity (4) of the copolymerization of H##salmon, etc., the polymole or the absorbent or the plasticity of the tree material #m, or the oxidation preventing agent, the ultraviolet television light element, for example, can be used for hanging a wall The backlight of the panel display, the light source of the measuring instrument, etc., refer to the invention, but the scope of the present invention is not limited to U, and the chromaticity coordinates are obtained according to JIS specification Z8701. The current efficiency of the light emission of the target element is obtained by the following formula 1. (Equation 1) Current efficiency = (luminous luminance per unit area) / (current density per unit area) 1 (disc optical ligand (Au(IPr)) (4F_pE)[(4-fluorophenylethyl) is diisopropylphenyl)-salt-2_subunit] gold]( Ligand i) Manufacture of organic electroluminescent device containing organic light-emitting layer as a body) Proud = Glass with tin oxide of EHC (slightly 1το) film: Ba Ming electrode substrate, vacuum The steaming unit (ULVAC JAPAN CO.) on the substrate was vapor-deposited with a film thickness of 40 nm under the vacuum of 2xl〇-3pa 320302 28 200910664 (l, i_double [4-( a hole transport layer 3 formed of bis-4_tolylamino)phenyl]cyclohexane (hereinafter abbreviated as TPAC), having a film thickness of 30 nm in 2-methyl-1,4·bis(triphenylsulfonyl) Benzene (1〇% by mass) and ruthenium, 3_bis(triphenylphosphonyl)benzene (9〇% by mass), a host material containing 5% by mass of a phosphorescent ligand (Au(IPr)(4F_pE) a light-emitting layer 4 of [(4-fluorophenylethynyl)[1,3-bis(2,6-diisopropylphenyl)imidazolylene]gold] (gold ligand 1), having a thickness of 30 nm a layer 5 consisting of 3_(4_biphenylheptylphenyl-5-tributylphenyl-H4-triazole, thickness 〇. The melon is made of lithium fluoride (hereinafter abbreviated as LiF) Electron transport layer 6, aluminum (A1) having a thickness of 10 nm as electrode 7, and The organic electroluminescent device of FIG. 1). The vacuum ruthenium plating is carried out by charging a raw material placed in a crucible placed on a substrate, and heating the hanging crucible together with the raw material. The ITO electrode 2 described in the month 'J is used as the positive electrode, and the A1 electrode 7 is energized as the negative electrode. When the voltage between the electrodes is gradually increased, the element starts to be clearly visible in the vicinity of about +7 V, and the element is clearly visible to the naked eye. 23V has 472ed/m: luminescence. The current efficiency associated with the illumination of this component is 丄57 at +23V. Example 2 (4) Photoligand (1) (Refer to (N, N, _diphenyl)-oxazolidin-2-ylidene) Silver (Coordination 2: Non-Patent Document 1) (manufacturing of organic electroluminescent elements contained in the organic light-emitting layer as a guest) A glass with an ITO film as a transparent electrode substrate, using a genuine steaming unit (Japan Vacuum Technology Co., Ltd., ULVACJAPANC) ^ The vacuum degree below the base w2xlG_3pa' sequential vacuum evaporation film and the hole transport layer 3 formed by TPAC, the film thickness of 320302 29 200910664 in 2·methyl-1,4-bis(triphenylsulfonyl) Benzene (10% by mass) and 1.3_bis(triphenylphosphonyl)benzene (90% by mass) of the host material, containing 5 〇 mass% of the phosphorescent ligand (ir(dpbic) 3) [ Light-emitting layer 4 of tris(N,N'-diphenylbenzylimidazolyl)anthracene] (ligand 2) 4 hole layer 5 made of TAZ with a film thickness of 30 nm, film thickness 〇5 nm An electron transport layer 6 made of lithium fluoride (hereinafter abbreviated as uf) and aluminum (A1) having a thickness of 1 〇〇 nm are used as the electrode 7 to form an electroluminescence element (Fig. 1). Put on the opposite substrate The raw material is placed in the hazard, and the hazard is heated together with the raw material. The above-mentioned ITO electrode 2 is used as a positive electrode, and the A1 electrode 7 is energized as a negative electrode, and the voltage between the electrodes is gradually increased, at about +9 In the vicinity of v, the element began to emit light with a clearly visible degree to the naked eye, and had a light emission of 466 cd/m2 at +27 V. The current efficiency with respect to the light emission of this element was i.47 cd/A at +21 V. Example 3 (2-methyl- Synthesis of 1,4-bis(triphenylsulfonyl)benzene)... Mixing I 2,5-di-molybdenum 203 /zl (1.5 mmol) in tetrahydrofuran in a 25 ml repair tube (Schuienk ratio (iv)) The solution of the i2mi was cooled to -78 with dry ice (solid carbon dioxide) and ethanol. 〇, a solution of pentane in butyl lithium (f = 1.48) was added dropwise 5. lml (7.5 mmol). After the solution was stirred at 78 ° C for 1 hour, triphenyl carbazine hydrate (3.3 mmol) was added. After stirring at -78 t; for 1 Torr, the reaction was carried out in an ice bath. After the reaction was completed, a suspension of 4 μm of water and 80 ml of dichloromethane was added to the reaction solution, and the obtained filtrate was washed with water 2 〇ηη1 χ2 times, ethanol 20 ml×2 times. After being purified, it was dried under reduced pressure to give a white solid of <RTI ID=0.0>&&&&&&&&&&&&&&&&&&&&&&&&&& 7.25(m,33H)' 2.11(s,3H) EI-MS(m/e) : 698(M+) CI-MS(m/z) : 698(MH+)

Elemental analysis observed C: 74.72 Η : 5.22 Theoretical value C : 74.00 Η : 5.20 Melting point: 305 ° C Decomposition temperature: 367 ° C Example 4 (2,5-dimercapto-1,4-bis(triphenyl) Synthesis of benzene) f 'In a 25 ml Schulenk tube, 1,4-dibromo-2,5-dimethylbenzene 396 mg (1.5 mmol) was mixed under argon, tetrahydro σ A solution of 12 ml of methane was cooled to a temperature of 78 ° C with dry ice (solid carbon dioxide)-ethanol, and a solution of tributyl pentoxide (f = 1.48) of 5.1 ml (7.5 mmol) was added dropwise. After the dropwise addition, the temperature of the reaction solution was maintained at 78 ° C for 1 hour, and then 1.12 g (3.3 mmol) of triphenylphosphonium chloride was added. After stirring at -78 ° C for 10 minutes, the reaction was carried out in an ice bath at 0 ° C for 2 hours. After the completion of the reaction, a suspension of 40 ml of water and 40 ml of methylene chloride was added to the reaction solution. The obtained mash was washed with water 20 ml×2 times, ethanol 20 ml×2 times, and then dried under reduced pressure to give a white solid of <RTI ID=0.0>> ). W-NMROOOMHz, CDC13) 5 : 7.57-7.13 (m, 32H), 2.03 (s, 6H) EI-MS (m/e): 712 (M+) CI-MS (m/z): 712 (MH+) Analytical observation C : 74.50 Η : 5.26 Theoretical value C : 74.22 Η : 5.38

Melting point: 337 ° C 31 320302 200910664

Decomposition temperature: 367 ° C. Example 5 (Synthesis of 2,5-dimethyl-1,4-bis(triphenylphosphonium)benzene). Under argon atmosphere in a 25 ml Schulenk tube Mix 1,4-dibromo-2,5-dimercaptobenzene 350 mg (1.2 mmol), tetrahydrofuran 8.5 ml of a colorless transparent solution, and cool to dryness (solid carbon dioxide)-ethanol to a temperature of 78 ° C, drip A tertiary butyl clock solution (f = 1.7) 3.5 ml (6.0 mmol). After the dropwise addition, the temperature of the reaction solution was maintained at 78 ° C for 1 hour, and then 896 mg (2.6 mmol) of triphenylphosphonium chloride was added. After stirring at -78 ° C for 10 minutes, it was stirred under ice bath for 2 hours. After the completion of the reaction, 40 ml of water and 80 ml of dichlorohydrazine were added to the reaction solution to separate the layers, and the aqueous layer was extracted twice with 20 ml of dichloromethane. The obtained organic layers were combined and dried over 1.2 g of magnesium sulfate. After filtration, the dichloromethane in the filtrate was distilled off under reduced pressure, and the obtained residue was washed with 20 ml of warm ethanol, 15 ml of warm hexane, and dried under reduced pressure to give 2,5-dimercapto-1,4- as a white solid. Bis(triphenylphosphonium)benzene 0.88 g (yield 99%). 'iH-NMRpOOMHz, CDC13) 3 : 7.59-7.20 (m, 32H), 2.38 (q, 4H), 0.62 (t, 6H) EI-MS (m/e): 738 (M+) CI-MS (m/ z) : 739(MH+) Elemental analysis observed C : 74.50 Η : 5.26 Theoretical value C : 74.22 Η : 5.38

Melting point: 272 ° C Decomposition temperature: 306 ° C Example 6 (Synthesis of 2,5-diethyl-1,4-bis(triphenylphosphonium)benzene) 32 320302 200910664 Repair tube in 25 ml (Schulenk Tube) mixed under argon atmosphere. 1,4-dibromo-2,5-diethylbenzene 350 mg (1.2 mmol), tetrahydrofuran 8.5 ml • solution, cooled with dry ice (solid carbon dioxide)-ethanol To a temperature of 78 ° C, 3.5 ml (6.0 mmol) of a tributyl pentoxide solution (f = 1.0) was added dropwise. After the dropwise addition, the temperature of the reaction solution was maintained at 78 ° C for 1 hour, and then 875 mg (2.6 mmol) of triphenylphosphonium chloride was added. After stirring at -78 ° C for 10 minutes, it was stirred at 0 ° C for 2 hours in an ice bath. After the completion of the reaction, 40 ml of water and 80 ml of dichloromethane were added to the reaction solution to separate a liquid. The aqueous layer was extracted twice with dichloromethane (20 ml), After filtration, the dichloromethane was distilled off from the filtrate under reduced pressure, and the obtained residue was washed with 20 ml of warm ethanol and 15 ml of warm hexane, and dried under reduced pressure to give 2,5-diethyl-1,4 as white solid. - bis(triphenylphosphonium)benzene 0.88 g (yield 99%). W-NMRpOOMHz, CDC13) 5 : 7.59_7.20 (m, 32H), 2.38 (q, 4H), 0.62 (t, 6H) EI-MS (m/e): 738 (M+) k CI-MS (m /z) : 739(MH+)

Elemental analysis observed C: 74.50 Η : 5.26 Theoretical value C : 74.22 Η : 5.38 Melting point: 272 ° C Decomposition temperature: 306 ° C Example 7 (Synthesis of 1,3-bis(triphenylphosphonium)benzene) In a 20 ml Schulenk tube, 495 mg (1.5 mmol) of 1,3-mothene benzene and diethyl _ 10 ml solution were mixed under argon atmosphere, and cooled to 78° with dry ice (solid carbon dioxide)-ethanol. C, dropwise addition of tributyl butyllithium 33 320302 200910664 alkane solution (f = 1.59) 2.8 ml (4.5 mmol). After the dropwise addition, the temperature of the reaction solution was maintained at -78 C for 1 hour, and then 1.12 g of triphenylphosphonium chloride (3.3 mmol) was added. After maintaining at 78 ° C for 15 minutes; after 15 minutes of mixing, the reaction was carried out for 1 hour in an ice bath at 〇C. After the completion of the reaction, water was added to the reaction solution by adding 4 ml of water and 80 ml of dichloromethane to separate the mixture, and the aqueous layer was extracted twice with dioxane 2 〇mi. The obtained organic layers were combined and dried over magnesium sulfate. After filtration, the dichlorohydrazine was distilled off from the mash liquid under reduced pressure, and the obtained residue was purified by a layer of stellite, and purified by a solution - (developing solvent: hexane) to obtain a white solid of 1,3 bis (three Phenylhydrazine) benzene 0.61 g (yield 59%). h-NMRpoOMHz, CDC13)6: 7.83 (s, lH), 7.50-7.31 (m, 33H) EI-MS (m/e): 684 (M+) Elemental analysis observed C: 73.04 Η : 4.98

Theoretical value C : 73.76 Η : 5.01 • Melting point: 227 ° C

Decomposition temperature: 325 ° CI Reference Example 1 (Synthesis of 1,4-bis(triphenylphosphonium)benzene) 1,4-monobromobenzene 236 mg mixed in an argon atmosphere in a 20 ml schulenk tube (l. 〇mrn〇l) and 4 氲 氲 夫 8 8ml solution, cooled with dry ice (solid carbon monoxide) - ethanol to -78, drip into the tertiary butyl clock pentane solution (f = l_7) 2.9ml (5.0 Mm). After the dropwise addition, the suspension was maintained at a reaction temperature of -78 ° C for 1 hour, and then 875 mg (2.2 mm 〇l) of triphenylphosphonium chloride was added. After stirring for 5 minutes while maintaining _78t:, it was reacted at 0 C for 2 hours in an ice bath. After the completion of the reaction, 4 ml of water and 40 ml of dichloromethane were added to the reaction solution to separate a liquid, and the suspended decane chloride layer was filtered. 34 320302 200910664 The obtained filtrate was washed with water 20 ml x 2 times, 20 ml x 2 times, 20 ml x 2 times of ethanol, and dried under reduced pressure to give 1,4-bis(triphenylphosphonium)benzene 0.56 g (yield 82) as a white solid. %). h-NMRpOOMHz, CDC13) 5 : 7.60-7.45 (m, 16H), 7.44-7.30 (m, 18H) EI-MS(m/e) : 684(M+)

Elemental analysis observed C : 73.87 Η : 5.09 Theoretical value C : 73·76 Η : 5.01 Melting point: 340 ° C Decomposition temperature: 365 ° C Reference example 2 (phosphorescent ligand (Au(IPr)(4F-PE)) [(4-Fluorophenylethynyl) [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] gold] (synthesis of gold ligand 1) in argon Add 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride 0.166 g (IPrH+Cl_: 0.39 mmol) in a 25 ml repair tube (Schulenk tube), a three-stage butoxy bell 67 mg (85 mass%: 0.51 mmol), 6.0 ml of tetrahydrofuran, and stirred at room temperature for 20 minutes. After distilling off tetrahydrofuran under reduced pressure, 6.0 ml of toluene was added, and the reaction was carried out at 70 ° C for 5 minutes. 174 mg (0.30 mmol) of 4-fluorophenylethyl (triphenylphosphino) gold and 6.0 ml of toluene in another 25 ml repair tube. After the dropwise addition, the reaction mixture was reacted at 70 ° C. 2.5 hours. After cooling the reaction mixture to room temperature, the benzene was distilled off under reduced pressure, and the obtained white solid was recrystallized from η-hexane-diethyl-di-carbazide to give gold ligand 1 White solid 0.1 87g (closed (%) , 2.60 (sept, 4H), l_38 (d, 12H), 1.21 (d, 12H) FAB-MS (M/Z): 705 (M+H) + luminescence analysis: (CHC13, 77K, Ex250nm); l ( Nm): 412 (max), 430, 451 Elemental analysis Observed value C : 59.32 Η : 5.68 N : 3.95 Theoretical value C : 59.66 Η : 5.72 N : 3.98 Example 8 (Production of pure blue phosphorescent organic electroluminescent device) A glass coated with an indium tin oxide (hereinafter abbreviated as ITO) film made of EHC was used as a transparent electrode substrate, and a vacuum vapor deposition apparatus (ULVAC JAPAN CO., manufactured by Nippon Vacuum Technology Co., Ltd.) was used. 2xl (vacuum degree below T3Pa, sequentially evaporating a hole transport layer 3 of 2-(4,-tridecylfluorenylphenyl)triphenyl with a thickness of 40 nm, film thickness 3 Onm in 2-methyl a guest phosphorescent ligand (Au(IPr)(4F-PE)[-4- in the host material of -1,4-bis(triphenylphosphonium)benzene (hereinafter abbreviated as .Me-p-BTPGB) Fluorophenylethynyl)[1,3-bis(2,6-diisopropylphenyl)imidazolium-2-phenylene]gold] Slightly Au(IPr)(4F_PE)) 5.0% by weight of luminescent layer 4, thickness 30nm from 3-(4-biphenyl)-4-indolyl-5-tert-butylphenyl-1,2,4 a hole layer 5 formed by triazole (sublimation refined product 'slightly 以下), an electron transport layer 6 made of a fluorinated chain (hereinafter abbreviated as LiF) having a thickness of 0.5 nm, as an electrode 7 having a thickness of 100 nm Aluminum (hereinafter abbreviated as A1) is used to form an electroluminescent element. Vacuum vapor deposition is carried out by charging a raw material placed in a crucible placed on a substrate, and heating the crucible together with the raw material. The ITO electrode 2 is used as a positive electrode, and the A1 electrode 7 is used as a negative electrode and is electrically connected to 36 320302 200910664. When the voltage between the electrodes is gradually increased, the component starts at about +14 V, and the component can be clearly recognized by the naked eye. 3.9 cd/m2 in +23V • Illuminated. The current efficiency was 0.017 cd/A at +20V. The luminescent color of this element was measured by a spectrophotometer. The spectrum obtained by the voltage between the electrodes at +19 V was confirmed to have a chromaticity square. The value was x = 0.172 and y = 0.157. Further, the EL spectrum of the organic electroluminescence device is shown in Fig. 1, and it is understood that the deep blue region near 425 nm has a maximum peak of phosphorescence photoluminescence f. Production of an organic electroluminescence device containing SIC0009 as a hole transport layer. A glass coated with an ITO film made of EHC is used as a transparent electrode substrate, and a vacuum vapor deposition device manufactured by ULVAC JAPAN CO. On the substrate, a hole transport layer 3 of 2-(4'-trimethyldecylphenyl)triphenyl having a film thickness of 30 nm was sequentially deposited at a vacuum of 2×1 (T3Pa or less), and the film thickness was 30 nm. (Me-p-BTPGB) in the host material I has a guest (in 11 (11) 1 〇 (4? -?)) 5.0% by weight of the light-emitting layer 4, a thickness of 30nm formed by TAZ Layer 5, an electron transport layer 6 made of LiF having a thickness of 0.5 nm, is made of A1 having a thickness of 100 nm of the electrode 7, and is made into an electroluminescence element. Vacuum evaporation is performed in a crucible placed opposite to the substrate. The raw material is charged and the crucible is heated together with the raw material. The ITO electrode 2 described above is used as a positive electrode, and the A1 electrode 7 is energized as a negative electrode, and the voltage between the electrodes is gradually increased. At about +12 V, the component starts to be visible to the naked eye. A clearly recognizable degree of blue luminescence, illuminating at 7.4 cd/m2 37 320302 200910664 in +25V. The rate was 0.026 cd/A at +22 V. The luminescent color of this device was measured by a spectrophotometer of Japan Spectrophotometer. The spectrum obtained by the voltage between electrodes was +1 8 V, and the chromaticity coordinate value was confirmed to be x=0.176. y = 0.175. Further, the EL spectrum of the organic electroluminescence device is shown in Fig. 5, and it is understood that there is a maximum luminescence peak of phosphorescence in the deep blue region near 424 nm. Reference Example 3 (1,4-double (III) Synthesis of phenylhydrazine) benzene) In a 20 ml Schulenk tube substituted with sufficiently dry argon, 236 mg (1.0 mmol) of 1,4-dibromobenzene and 8 ml of tetrahydrofuran were mixed in an argon atmosphere. The clear solution was cooled to a temperature of 78 ° C with dry ice (solid carbon dioxide)-ethanol, and butyl chloride solution (f = 1.7) of 2.9 ml (5.0 mmol) was added dropwise. After the dropwise addition, it was changed to yellow. The reaction suspension was maintained at a reaction temperature of -78 ° C for 1 hour, and then 747 mg (2.2 mmol) of triphenylphosphonium chloride was added. After stirring at a temperature of 78 ° C for 5 minutes, in an ice bath ί Stir at 〇 ° C for 2 hours. After the reaction was completed, add 40 ml of water and 40 ml of dichloromethane to the reaction solution to separate the liquid. The obtained filtrate was washed with water (20 ml×2 times, 20 ml×2 times, 20 ml×2×), and dried under reduced pressure to give 1,4-bis(triphenylphosphonium)benzene 0.56 as a white solid. g (yield 82%). W-NMRpOOMHz, CDC13) 5: 7.60-7.45 (m, 16H), 7.44-7.30 (m, 18H) EI-MS (m/e): 684 (M+) C : 73.87 Η : 5.09 38 320302 200910664

Theoretical value C : 73.76 Η : 5.01 Melting point: 340 ° C

Decomposition temperature: 365 ° C McC. 4 (phosphorescent ligand (Au (Ipr) (4F-pE) [(4-fluorophenylethynyl) [1,3-bis (2,6-diisopropyl) Synthesis of phenyl)imida_2_subunit]gold])) Add 1,3-bis(2,6-diisopropylphenyl) to a 25 ml Schulenk tube under chlorine atmosphere Imidazolinium chloride 0.166 g (IprH+Cr: 0.39 mmol) 'Diethylpotassium butoxide (85% by mass, 67 mg, 0.51 mmol) of tetrahydrofuran (6 〇ml) was stirred at room temperature for 2 hr. After deuteration and decantation to remove tetrahydrofuran, 'toluene (6 〇πι1) was added, and the mixture was stirred at 7 ° C for 5 minutes. The reaction mixture was passed through, and the filtrate was dropped into 4-fluorophenylethyl (triphenylphosphino) gold (174 mg, 0.30 mmol), toluene 6. 〇mi, placed in another 25 ml. After the dropwise addition, the reaction mixture was heated at 7 ° C for 2.5 hours. After the reaction mixture was cooled to room temperature, the toluene was distilled off under reduced pressure. The obtained white solid was recrystallized from n-hexane/diethyl ether/dichlorobenzene to give the object as a white solid. Yield 88%) ° W-NMRPOOMHz, CDC13) 5 : 7.49 (dd, 2H), 7.30-7.22 (m, 8H), 7.12 (s, 2H), 6.82-6.75 (m, 2H), 2.60 (sept, 4H), 1.38 (d, 12H), 1.21 (d, 12H) FAB-MS (M/Z): 705 (M+H)+ luminescence analysis: (CHC13, 77K, Ex250nm) A (nm): 412 (max ), 430, 451 Elemental analysis observation C : 59.32 Η : 5.68 N : 3.95 Theoretical value C : 59.66 Η : 5.72 N : 3.98 39 320302 200910664 (Probability of industrial use) The present invention relates to 4 wavelengths below 44Gnm. An organic electroluminescent element (electric field illuminating element) of a photoluminescence illuminating edge, and a scaly photoluminescence illuminating peak in the dark blue area of f 440 nm or less, and an illuminating color in CIE (International Commission on Illumination) The y coordinate value of the color system is 7"pieces" and the component materials of the organic electroluminescent element::she organic electroluminescent elements can be considered, for example, in full color , the shoulder is not a good element into a useful component. BRIEF DESCRIPTION OF THE DRAWINGS The rainbow spectrum of the organic electroluminescent device of Example 1 is shown. Figure 2 is an organic example of Example 1. The EL spectrum of the electroluminescent element (expanded Fig. 3, Embodiments 1, 2 and § eclipse, is a glass substrate, 2 is a transparent, Hi-emitting element, 4 is a light-emitting layer, and 5 is a hole layer 6, the hole transport layer, the fourth figure is the organic electro-electric 4 of the embodiment 2: '7 is the electrode. Figure 5 is the organic electricity of the embodiment 8 =: spectrum. [Main component symbol description] The muscle of the piece is first. The glass hole is the electrode layer of the electrode layer 246 ΙΤ〇 The film electrode layer is the electron wheel layer 320302 40 7

Claims (1)

200910664 X. Patent application scope: 1. An organic electroluminescent device is formed by forming a light-emitting layer between electrodes, or a thin layer of organic compound having three light layers, which is characterized by having a wavelength of 44 〇 nmw. Luminescence peak of phosphorescent electroluminescence. 2. For example, the organic electroluminescent device of the patent application range f is the maximum luminescence peak of the phosphorescence photoluminescence peak in the dark blue region below 4, and the luminescent color is in the International Commission on Illumination. If the coordinate value is less than 180180, 3. If the organic electroluminescent device of the first and second divisions of the patent application is in the optical layer, it contains "a kind of compound or multiple kinds of wrong compounds." The third organic electroluminescent device, wherein the deuterated compound is a compound represented by the general formula (1), QeR1R2R3 GeR4R5Re {1) (In the formula, L is 〇 to 2, k is an integer from 〇 to 3; Μ or not the same 'is a yard base, a ring-based base, a di-base:; a di-fragrance, a heterocyclic group, a burn An oxy or aryloxy group: a di-, fluorenyl, cycloalkyl, aryl, arylalkyl, alkoxy, laughing/radical | group or an organic (tetra) group; a read group, a sulfur group, a aryl group 'R1 or R6 may also be a ring bond group which may be a single bond, a lysine; a two-ring ring' which binds a hard thioether bond, an alkyl group, a 320302 41 200910664 alkyl group, or a sulfur-extension group; X is an alkyl group. a cycloalkyl group, a aryl group, an aryloxy group, a sulfur-burning group, an aromatic sulfur U-based group, an amine group having a substituent or a substituted group, and an amine group having a substituent. Electromechanical A, occluded electroluminescent device, erbium, mismatched 5 system is a general formula (la) 锗 compound, GeR1R2R3 (la) / ^^GeR4RsR6 ^ U and RI or even R6 is the scope of the patent Item 4. 6.::: The organic electroluminescent compound of the fourth aspect of the patent range is a wrong compound represented by the following formula (2), ... (In the above formula, it is the integer of 〇2 to 2 敕 ^^ 疋2, Π1 is the gold-positive number of the 至1 to 3, and the number k疋 is synonymous with the narration; Ar can be the same as η, It is the same as the aromatic genus. (2) It can also be the second of these. The base is any hydrogen thereof. 攸 atom, alkyl, cycloalkaneoxy, aryl, aryl, aryl. · π sulphuryl, arylthio, or organodecane wu household, at the same time, different Ar / 基 卩 Ar can also be the same 锗 atom 320302 42 200910664 different Ar base number is equal to m; The αγ may also be bonded via a single bond, an ether bond, a thioether bond, an alkylene group, an oxygen alkyl group, or a sulfur alkyl group; further, R is an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, Or an oxy group; X is an organic electroluminescence device according to the invention of claim 4, wherein the ruthenium compound is a ruthenium compound represented by the following formula (2a) ; f (wherein k, m, η, χ, Ar, and R are synonymous with those described in the application). ® ^ 8. The organic electroluminescent conversion according to item 7 of the patent application, wherein the compound is an anthracene compound represented by the general formula (2b), Ar is the same as described in item 7 of the patent application (in the above formula, k, X meaning). 9. If the application of the 8th item of the patent scope is the eighth item, the total 丄 丄 致 , , , , , , , , , , , σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ σ Group 320302 43 200910664 Selected at least 1 compound 10. The organic electroluminescent device according to any one of items 3 to 9 of the claims, wherein the luminescent layer contains a plurality of bismuth compounds. 11. The organic electroluminescent 1 luminescence member according to any one of the items 1 to 1 of the patent application, wherein the luminescent layer contains a mono- or a substituent which constitutes a plurality of compounds represented by the following formula: , V — ——AuL ο) (In the above formula, L is a nitrogen-containing heterocyclic carbene ligand, γ is an alkyl group, a cycloalkyl group, an aromatic group, an aromatic group, or a heterocyclic group, and, The plural hydrogen atoms of the y-f of the formula may also be derived from an atom, an alkyl group, a cycloalkyl group, a fluorenyl group, an aryl aryl group, an alkoxy group, an aryloxy group, a diestylamine group, a carbon-based base. Or a substituted by an aryl group, and a plurality of hydrogen atoms on a carbon atom of γ, an alkyl group, a dilute group, an aromatic group, a aryl group, an alkoxy group, an aryloxy group, a second 320302 44 200910664 alkylamino group In the case where a carbon alkyl group or a carbon aryl group is substituted, the phase groups may also be bonded to each other to form a ring). 12. The organic electroluminescent device according to any one of claims 1 to 5, which comprises a hole transport layer, and the hole transport layer contains a single or a substituent to form a plurality of different species. Compound shown by the formula, early one (In the above formula, Z is a single or plural alkyl group, a cycloalkyl group, an aryl group, an arylalkyl group or a heterocyclic group; further, one or a plurality of hydrogen atoms on the carbon atom of z' may also be a halogen atom or an alkane. Substituted by a cycloalkyl, alkenyl, aryl, arylalkyl, alkoxy, aryloxy, dialkylamino, carboalkyl, carboaryl or organoalkylene group). 45 320302