TW201211003A - Light-emitting device material and light-emitting device - Google Patents

Abstract

Disclosed is a light-emitting device material which comprises a compound having a specific structure of a carbazole skeleton and can realize a light-emitting device having high light-emitting efficiency and durability. Also disclosed is a light-emitting device comprising the light-emitting device material.

Description

201211003 VI. Description of the Invention: [Technical Field of the Invention] - The present invention converts electrical energy into light, and can be used for displaying components, flat panel displays, backlights, lighting, indoor dressing, logos, billboards , electronic cameras and optical signals generate light-emitting elements in the field of germanium. [Prior Art] When an organic thin film light-emitting element that emits light from a cathode, * λ > $, t , a left-injected electron and a hole injected from an anode are sandwiched between two electrodes, In the past years, the tongue has progressed. The light-emitting element is characterized by high-brightness light emission under a low plastic driving voltage and multicolor light emission obtained by selecting a light-emitting material. The research has been carried out by many research institutes since the Kwdak company's cw Tang et al. and no organic thin film elements can emit light with high brightness. Further, the organic bismuth-emitting device uses various luminescent materials 2 in the luminescent layer to provide a variety of luminescent colors. Therefore, practical research on displays and the like is reserved in the luminescent materials of primary colors, and the research of green luminescent materials is the most studied. Collar, then, in red luminescent materials and blue luminescent materials, for the purpose of improving the characteristics of the study. As a luminescent material, it is conventionally known to use a fluorescent (single-state luminescence) material, which differs in the spin multiplicity when molecules are excited by recombination of electrons and holes, and the singlet excitons are in a ratio of 25% and triplet. The child is produced at a ratio of 75%, so in order to improve the luminous efficiency, a phosphorescent (triple state 100121937 3 201211003 light) material was previously tried. Therefore, as a main material for the performance of the use of the bismuth material as a dopant, it is proposed to have a material-containing bone _ when it is referred to as a patent document. Further, a compound having a tri-morphine skeleton as a compound (for example, a compound to be transported as a host material can be used as a host material (Examples 3 to 4). Further, a material other than the luminescent material is also subjected to a patent: if a hole can be used for transport A compound having a high capacity and excellent electron blocking ability is a compound having a skeleton of 嗤 skeleton as a hole transporting material (for example, refer to the patent document [Prior Art Document] '° [Patent Document] Patent Document 1: Japanese Patent Laid-Open No. 2003-133075 [Patent Document 2] Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Disclosure No. 2011/24451 [Draft of the Invention] (Problems to be Solved by the Invention) However, an organic thin film light-emitting element must satisfy an improvement in luminous efficiency, a decrease in driving voltage, and an improvement in durability, particularly regarding a phosphorescent material. It is difficult to fully satisfy all of these properties. The object of the present invention is to solve the problems of the prior art and to provide an organic thin film with high luminous efficiency and durability. Membrane light-emitting element 100121937 4 201211003 (Means for Solving the Problem) The present invention is a light-emitting element material characterized by containing a compound having a ° card π sitting skeleton represented by the following general formula (1). [^ib 1]

(R31 to R38 are each selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, aryl ether, aryl sulfide, aryl, a group consisting of a heteroaryl group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an amine fluorenyl group, an amine group, a decyl group, a -P(=0)R39R4G group, and a group represented by the following formula (2). And R40 is an aryl group or a heteroaryl group. In R31 to R38, the adjacent substituents may form a ring with each other, wherein any one of R31 to R38 is a group represented by the following formula (2), and a formula (2) Any one of R41 to R49 is bonded. L is selected from the group consisting of a single bond, an extended aryl group and a heteroaryl group. HAr is an aromatic heterocyclic group having electron accepting nitrogen. 2]

100121937 5 (2) 201211003 R~R i are selected from hydrogen, silk, cyclofilament, heterocyclylcycloalkenyl, fluorenyl, alkoxy, thiol, aryl sulfenyl, aryl sulphide: hetero Base, «, county, silk, oxygen county, amine mercapto, i alkyl and - Ρ (,, the group formed. r5Ur51 is an aryl group. R~R towel's adjacent substituents can form a ring with each other. a group consisting of a Z-alkyl group, an aryl group, and a heteroaryl group, wherein any one of the ruler and the ruler 49 is bonded to any of the points f to R38 in the formula (1). According to the present invention, an organic thin film light-emitting element having high luminous efficiency and long-lasting efficiency can be provided. [Embodiment] The compound having a carbazole skeleton represented by the formula (1) of the present invention will be described in detail. [Chemical 3]

(1) cycloalkenyl, alkynyl, alkoxy, alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, arginyl, carbonyl, carboxyl, oxycarbonyl, amidino, amine, The group consisting of a decyl group, _P(=0)R39R4〇, and a group represented by the following formula (2) is a group of 100121937 6 201211003. β and C are aryl or heteroaryl. In R31 to R38, adjacent groups may form a ring with each other. Wherein, the base represented by any of ί^~κ38, and R4!~49~ in the general formula (2), the formula (2) ^Y moxibustion at any position of the sister τ • selected from a single bond, a group consisting of a base and a heteroaryl group. ΗΑγ is; ^ an electron-accepting nitrogen aromatic heterocyclic group. ~, there is ‘[化4]

R41~R48 are respectively selected from hydrogen, alkyl, cycloalkyl, heterocyclic ring, block group, silk group, (tetra) group, aryl group, aryl sulphur heart = heteroaryl group, dentate, several groups, county, A group consisting of oxygen county, amine methyl group, amine: earth alkyl and -P(=0)W. R50&r soil, stone base. The substituents of _ may form a ring with each other. a group consisting of a base group, a square group, and a heteroaryl group. Here, r4 ^free - is bonded to any of the positions 8 to 8 in the general formula (1). In the substituents, hydrogen may also be ruthenium. Further, a saturated aliphatic aliphatic hydrocarbon group such as a silk, an ethyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a second butyl group or a hydrazine group, which may have a silk and a dibutyl group. The feelings of the claws ^ take silk butterfly _; ^ base. The silk, the aryl group and the heteroaromatic surface are also described in the following paragraphs. Further, 焓 100121937 201211003 base = the number of the versatile is not particularly limited, and is usually 1 or more and 2 G or less, and more preferably i or more and 8 or less in terms of availability and cost. The ring-burning group may, for example, represent a ring-based group, a cyclohexyl group, a thief, a ruthenium, or the like, and may have a substituent or may have no substituent. The carbon number of the base portion is not particularly limited, but is usually in the range of 3 or more. x The heterocyclic group is, for example, an aliphatic ring of an atom other than a ring of an n-ring, a chiral ring, or a cyclic amine, which may have a substituent or may have a substituent. The number of carbon atoms of the ring group is not particularly limited, and is usually in the range of 2 or more and 20 or less. The term "gyro group" means, for example, an unsaturated aliphatic hydrocarbon group having a tapered bond such as a hexa-diphenyl group, a dipropyl group or a butyl succinyl group. The number of carbon atoms of the alkenyl group is not particularly limited, and is usually in the range of 2 or more and 2. [The cycloalkenyl group] is, for example, a cyclopentenyl group, a cyclopentadienyl group or a ring. An unsaturated alicyclic hydrocarbon group containing a double bond, such as a dilute group, which may or may not have a substituent. The so-called fast group, for example, the heart # scale contains a triple bond (4) and an aliphatic smoky group, which may have a front Daiji, the village does not have a silk base. Silk carbon number is particularly limited, usually 2 or more, 2 () or less ^ so-called alkoxy, for example, methoxy, ethoxy, propoxy, etc. The key is the key to the fat female base, and the series _ base may have the substitute 100121937 201211003 base, or not The number of carbon atoms of the alkoxy group is not particularly limited, but is usually in the range of 1 or more and 20 or less. The term "alkylthio group" means an oxygen atom of an ether bond of an alkoxy group which is substituted by a sulfur atom. The thiol group may have a substituent or may have no substituent. The number of carbon atoms of the thiol group is not particularly limited, and is usually in the range of 以上 or more and 2 Å or less. The aryl ether group, for example, represents a phenoxy group or the like. The functional group of the aromatic hydrocarbon group may be bonded to the ether group, and the aromatic hydrocarbon group may have a substituent or may have no substituent. The number of carbon atoms of the aryl ether group is not particularly limited, and is usually in the range of 6 or more and 4 Å or less. Sulfur_, which means that the oxygen atom of the (four) group is formed by a sulfur atom. The aromatic group of the aromatic towel may have a substituent or may have no substituent. The carbon number of the Fang County is not particularly limited, and is usually 6 or more. The range of 4 Å or less. The aryl group, for example, represents a phenyl group, a naphthyl group, a phenyl group, a benzyl group, a phenanthryl group, a bis-phenylene group, a succinyl group, and a yl group may have a substituent or may have no substitution. The carbon number of the aryl group is not specified, usually 6 or more. 40 The following called the range heteroaryl group represents furyl system, - based group, [eta] than square piece goods group, say group 0 to Han Lin Ji, naphthyridinyl, benzofuranyl

, _ 丞 并 and thienyl, fluorenyl, two J

The fluoromonyl group, the dibenzopyenyl group, the (tetra) group and the like have a ring group of U or a ring other than the stone in the ring, which may be unsubstituted or may be (four) generation. There are no special mosquitoes in the carbon number of the hetero-basic group, and it is usually in the range of 2 or more and H 100121937 201211003. The halogen atom' means fluorine, chlorine, bromine or iodine. The carbonyl group, the thiol group, the oxycarbonyl group, the amine fluorenyl group, the amine group, and the phosphine oxide group may have a substituent or may have no substituent. Examples of the substituent include a decyl group, a cycloalkyl group, an aromatic group, and a heteroaryl group. The substituents may be further substituted. The carbonyl group, the carboxyl group, the oxycarbonyl group or the aminecarbamyl group may have a substituent or may have no substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group and the like, and the specific substituent may be further substituted. The amine group ' may be unsubstituted or substituted, and examples of the substituent include, for example, an alkyl group, a cyclofilament, an aryl group, and a heteroaryl group. The substituent may be substituted. The so-called Shi Xi Xuan base, for example, means a functional group having a bond to the Shi Xi atom, such as a triterpene base group, and a wealthy substituent. The carbon number of the Shih-hsing base is not particularly limited, and is usually in the range of 3 or more and 2 G or less. Further, the number of stone ceremonies is usually in the range of 1 or more and 6 or less. The aryl group is a divalent group derived from a phenyl group, a naphthyl group, a phenyl group, a phenanthryl group, a triphenylene group, a silk, or the like, which may have a substituent or may have no substituent. . The silk of the silk is fixed and the scale is usually 6, or more. The following range. In the case where l of the formula (1) is an aryl group, the aryl group may have a substituent or may have no substituent, and the substituent has a carbon number in the range of 6 or more and 60 or less. The so-called heteroaryl group is represented by 吱 基 & 塞 塞 塞 塞 塞 100 100 100 100 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 121 a cyclyl group derived from a cyclic aromatic group having an atom other than one or more carbons, which may have a thiol group, a dibenzobenzopyryl group, a dibenzoxanyl group, a decyl group, or the like. The substituent may or may not have a substituent. The carbon number of the heteroaryl group is not specified, and is usually in the range of 2 or more and 3 inches or less. In the case where L of the formula () is a heteroaryl group, the heteroaryl group may have an alternative material, and may also have a wire, and the substituent carbon number is in the range of 2 or more and 50 or less. In the case where the substituted substituents form a loop with each other, any two adjacent substituents (e.g., the formula (3)^2(4)) may be bonded to each other (4) to form a ring of the non-co-peach. As a constituent element of the condensed ring, in addition to carbon, it may contain nitrogen deuterium, sulfur, lin, and dream atoms, and may further condense with other rings. The aromatic heterocyclic group having an electron-accepting nitrogen is represented by. Than base, 啥 基, 异 & & 尔 尔 尔 、 、 异 异 异 异 异 异 异 异 异 异 异 异 异 & & & & & & & & & & & & & & & & & & & & & & & & & & & & & & & (4) A heterocyclic aryl group having one or more nitrogen atoms having at least electron acceptability in the ring as a cyclic aromatic group of an atom other than carbon. The aromatic heterocyclic group containing an electron-accepting nitrogen may be unsubstituted or substituted. The number of the electron-accepting gas contained in the Fangfu County containing the electron-accepting is not particularly limited, and is usually in the range of 仏 or 3 or less. Further, the substitution in the case of an aromatic-ring-based deuteration containing electron-accepting nitrogen 100121937 201211003 is specifically limited, for example, _, aryl, heteroaryl, etc., 乂..., not excessively divided, and containing electron-accepting nitrogen Aromatic miscellaneous production, and it contains an aromatic number of 6 to % Hi and a carbon number A. Further, the a-aromatic heterocyclic group which is a nitrogen-generating group is preferably a terracotta or a ruthenium, and examples thereof include a phenyl group, a naphthyl group, a biphenylphenanthyl group, and a combination: r | w Fuji, L-based, specific κ-based, _-based, hetero-based phenyl-based (tetra)-based, "Bite bite, tower base, beryl, taste wow." Definition, three-speaking thiol, benzene (tetra), benzo, benzo, but not limited to these. Soil Here, the electron-accepting nitrogen means a nitrogen atom which forms a multiple bond with an adjacent atom. The nitrogen atom has a higher anion property, so the multiple bonds have the property of electron acceptability. Therefore, an aromatic heterocyclic ring containing electron-accepting nitrogen has a high electron affinity. The number of carbon atoms of the aromatic heterocyclic group containing electron-accepting nitrogen is not particularly limited, and is usually in the range of 2 or more and 30 or less. The linking position of the aromatic heterocyclic group containing electron-accepting nitrogen may be any moiety, for example, in the case of a pyridyl group, it may be a 2-β ratio β group, a 3-α ratio α group or a 4-σ ratio bite group. Any of the conventional compounds having a carbazole skeleton as a light-emitting device material does not necessarily have sufficient performance. The inventors of the present invention have focused on the strength of the hole transporting energy and the electron carrying energy of the compound having a carbazole skeleton in its improved research. Generally, a compound having a carbazole skeleton has a property of transporting two charges of a hole and an electron, and the inventors believe that the electron transport energy is inferior to that of a hole transport, so 100121937 12 201211003 = medium: charge balance collapse, which leads to The luminescent property is lowered, and according to this assumption, the compound having the skeleton represented by the general formula °) is widely used. > (} The compound having a Leica salivary skeleton has an aromatic heterocyclic ring containing a = salic skeleton and an electron-accepting nitrogen in the molecule. Thus, it can be considered that the aromatic heterocyclic ring of the electron-assisted X-nitrogen is involved. The electrons are injected and transported, so they can be enlarged to obtain the charge balance in the object, and exhibit high efficiency = excellent durability. Moreover, by connecting the material skeleton, it can maintain the taste of the moon frame itself. The high triplet energy level can suppress easy deactivation, so that a higher luminous efficiency can be achieved. Among the compounds represented by the formula (1) of this month, it is preferred that the compound represented by the general formula (3) a compound having a carbazole skeleton.

--------, Wanshi Luxiang, Fangji, Heteroaryl, S Su, County, Hi, Oxygen County, Aminomethyl thiol, Amino Silk and Affliction 0) R%n group. f and Rl7 are aryl or hetero-substituents. In R14, adjacent substituents may form a ring with each other. R15 is selected from the group consisting of = 100121937 13 201211003, an aryl group and a heteroaryl group. Heteronucleobase. (Lust, and "L" is selected from the group consisting of a single bond, an extended aryl group, and a halide having an electron accepting nitrogen, and the substituents are the same as those of the above formula (1). =..... Outside the formula, if R49 and L-HAr in the compound other than the compound represented by the formula (3) in the formula (1), and R15 and L-HAr are different, In the case of an asymmetric structure, the effect of suppressing the interaction between the skeletons is improved by '15 can be formed: the film is fixed, and the durability is improved, so R and R are preferably not reduced by the compound having a ten-seat skeleton. state

The HAr is preferably a substituent which does not lower the triplet energy level of the compound having a carbazole skeleton represented by the general formula (1) or the general formula (7), and preferably, the conjugated substituent is not excessively extended. It is especially preferred to be a pyridyl group, a pyrimidinyl group or a trisyl group. The synthesis of the compound having a carbazole skeleton represented by the formula (1) can be carried out by a known method. The method for synthesizing the carbazole dimer includes, for example, a method of oxidative coupling reaction using carbazole under iron (III) chloride, but is not limited thereto. In addition, as a method of introducing a substituent to N of carbazole, for example, a method of coupling reaction of a carbazole derivative using a palladium or a copper catalyst with a dentate is mentioned, but the invention is not limited thereto. The carbazole compound represented by the above formula (1) is not particularly limited, and specific examples are as follows: 100121937 201211003. [6] 100121937 201211003

100121937 16 201211003 [化7] [16] [19]

[22] [25]

100121937 17 201211003 [Chem. 8]

[37] [38] [39]

100121937 18 201211003 [Chemistry 9]

100121937 19 201211003 [化 ίο]

[58] m [53⁄4 [61]

100121937 20 201211003[化11] [64] [65] [66]

100121937 21 201211003 [Chem. 12]

100121937 22 201211003 [Chem. 13]

100121937 23 201211003 [Chem. 14]

Γ\ Ν ό

100121937 24 201211003 [Chem. 15]

100121937 25 201211003 [Chem. 16]

[133] · [134] [135]

26 100121937 201211003[化17] [136]

Ch3

[142]

[145]

100121937 27 201211003 [Chem. 18]

1154] Ip,

100121937 28 201211003[化 19]

1166} [167] [1681

H^N

100121937 29 201211003[化 20]

1172]

[173] 1174]

100121937 30 201211003 [Chem. 21]

[184]

ό ό 6 100121937 31 201211003 [Chem. 22] 1193] [194] [195] Q 9, 〇

[196] [197] [Tune [199]

[200] ί2〇1]p 0

32 100121937 201211003[化23] [205]

N

M

[211]

[210]

100121937 33 201211003[化 24]

[218] [219]

020]

[222]

100121937 34 201211003 [Chem. 25] [226] [229]

[232] The compound of the material reading frame of the formula (1) of the present invention can be used as [223] == material:. Therefore, the material of the light-emitting element of the present invention is a material of any layer of the sound vr, as described below, and is used in addition to materials for the hole transport layer, the light-emitting layer and/or the electron transport layer. ^ 100121937 35 201211003 Extreme protective film material. By using a compound having a carbazole skeleton represented by the formula (丨) of the present invention in any layer of a light-emitting device, a light-emitting device which can obtain high light-emitting efficiency and is excellent in durability can be obtained. The compound having a D-catalyzed skeleton represented by the general formula (1) has high luminous efficiency, a relatively small doublet energy level, bipolarity (two charge transporting property), and film stability, and is therefore preferably used for light emission. In the luminescent layer of the component. In particular, since it has a higher triplet energy level, it is preferably used as a host material with respect to a phosphorescent dopant in the light-emitting layer. Next, an embodiment of the light-emitting element of the present invention will be described in detail. The light-emitting element of the present invention comprises an anode, a cathode, and an organic layer interposed between the anode and the cathode, the organic layer comprising at least a light-emitting layer that emits light by electrical energy. The organic layer may include, in addition to the structure including only the light-emitting layer, a hole transport layer/light-emitting layer/electron transport layer, and 2) a light-emitting layer/electron transport layer, and 3) a hole transport layer/light-emitting layer, and the like. The composition of the layers. Further, each of the above layers may be a single layer or a plurality of layers. In the case where the hole transport layer and the electron transport layer include several layers, the layers on the side in contact with the electrodes are respectively referred to as a hole injection layer and an electron injection layer, respectively, and the holes are described unless otherwise specified. The injection material is contained in the hole transporting material, and the electron injecting material is contained in the electron transporting material - in the light emitting element of the present invention, the anode and the cathode have a function for supplying a current sufficient to realize the light emission of the element, and the light is taken out. Preferably, at least one of 100121937 36 201211003 is transparent or translucent. Usually, the anode formed on the substrate is set as a transparent electrode. The material used for the anode is, as long as it is a material which can efficiently inject a hole into the organic layer, and is transparent or translucent for taking out light, examples thereof include tin oxide, indium oxide, indium tin oxide (ITO), and oxidation. Conductive metal oxides such as indium (IZO), metals such as gold, silver, and chromium, inorganic conductive materials such as copper iodide and copper sulfide, and conductive polymers such as polythiophene, polypyrrole, and polyaniline. Particularly limited, it is particularly desirable to use 1το glass or NESA glass. These electrode materials may be used singly or in combination of several materials. The electric resistance of the transparent electrode is not limited as long as it can supply a current sufficient to realize the light emission of the element, and is preferably low resistance from the viewpoint of power consumption of the element. For example, if it is an IT 〇 substrate of 300 Ώ/□ or less, it functions as a device electrode. It is also possible to supply a substrate of about 1 ΩΩ/□. Therefore, it is particularly preferable to use a substrate with a low resistance of 20 Ω/□ or less. . The thickness of the crucible can be arbitrarily selected in accordance with the resistance value, and is usually used in the vicinity of just ~3〇〇nm. Further, in order to maintain the mechanical strength of the light-emitting element, it is preferable to form the light-emitting element on the substrate. The substrate drum makes __ or no glass substrate. The thickness of the glass substrate can be as long as it has a strong mechanical strength. It is enough for 〇.5 to follow. Regarding the material of the broken glass, since it is preferable to dissolve ions from the glass, it is preferable to use no glass. Alternatively, it is also commercially available as a s1〇2 4 barrier coating, so it can also be used. In addition, the port 100121937 37 201211003 requires the anode to function stably, and the substrate does not form an anode on the plastic substrate. The IT0 film is formed into a square, and is a glass, for example, a plating method or a chemical reaction method, and the like, and is not particularly limited, and may be an electron beam method or a material for sputtering a cathode, as long as the electron can have six texts. The substance is not particularly limited. It is generally preferred to inject a metal such as tin, bismuth, or indium into the light-emitting layer, or an alloy or a multilayer of the metal with a gold, silver, copper, iron, or a low work function metal. The resistance value of yttrium, potassium, calcium, magnesium, etc., the easiness of film formation, the stability of the film, and the main component are preferably S, G, and Mg. In particular, it is preferable that 兀/, 疋, and right-handed by magnesium and silver transpiration, and the electron transport layer and the electron injection layer of the invention are injected, it is easy to drive to the present. The electrons can be low-voltage, and the following examples are preferable. In the case of gold, silver, copper, iron, tin, indium, etc., the cathode, the pin, the gold dioxo, and the titanium oxide are used. The combination of metal and cerium 4 inorganic materials, polyvinyl chloride, hydrocarbon-based polymer compounding "organic high-scoring ^ ^ ethoxylated alcohol, the upper layer as a protective film layer. Among them, in the yin _ ^ material layer in the genital light-emitting structure) Correction, protection _ 仏 结构 structure (top light material selection. The visible light region of the electrode has a beam of Lu ion ionization and coating, etc., gamma is resistance heating, electronic enthalpy, etc., there is no particular limitation. The layer can be transported by a layered or existing hole to transport the material, or by using a hole wheel to feed the material or the material of the body, and the mixture of the knife, the knife, and the test agent (4). It is also possible to add an inorganic salt such as gasification iron 100121937 38 201211003 _ to form a polling layer. The electrode of the electric reading material must efficiently transport the electrode from the positive electrode, so it is ideal for the efficiency of cavity injection. Higher, it can effectively transport the hole of the person who is injecting. Therefore, the requirement is The following substances have a suitable free potential, and have a large hole mobility, and are excellent in stability, and are difficult to produce impurities during production and production. The substance satisfying the above conditions is not particularly limited, and is preferably 4 , 4, _bis(N-(3-mercaptophenyl)-N-phenylamino) phenyl, 4,4, bis(yi(1~naphthyl)-N-phenylamino)biphenyl a diphenylamine derivative such as 4,4,,4,,_(3_mercaptophenyl (phenyl)amino)triphenylamine; bis(N-allylcarbazole) or bis ( Anthraquinone compounds such as fluorene-alkyl carbazole; lanthanide compounds; biscarbazole derivatives; pyrazoline derivatives; benzophenone derivatives or porphin derivatives, oxadiazole derivatives, phthalocyanine derivatives a heterocyclic compound such as a porphyrin or a living compound; a fullerene derivative; and a polycarbo- or styrene derivative having the above-mentioned monomer in a side bond, polybenzazole, polyaniline, polyfluorene, polyethylene In addition, an inorganic compound such as P-type Si or p-type Sic may be used. Further, a compound represented by the following formula (4) or tetrafluorotetracyanoquinol may be used. Methane (4F-TCNQ) or oxygen Molybdenum. [Formula 26]

100121937 (4) 39 201211003 R18 to R23 may be the same or different, and are selected from the group consisting of halogen, sodium, succinyl, cyano, and trifluoromethyl. Soil, wherein, if the hole transport layer or the hole injection layer contains (5) (1, 4, 5, 8, 9, 12 hexazatriazole), the material pressure is driven, so it is preferred . Low-footed electricity [Chem. 27]

In the present invention, the light-emitting layer may be formed of a single layer, a light material (host material, a material), and t may be a mixture of a dopant material or a single dopant. That is, in the light-emitting element of the material and the light-emitting layer, the light is emitted in the light-emitting layer, and the energy of the main body material (4) or the dopant material can be obtained, and the obtained material emits light. The mixing of the ancient host material and the dopant material is effective in the viewpoint of effectively utilizing the illuminance of the electric ant to return color purity. In addition, the main body of the main body is included as a whole, or may be a combination of several kinds of materials and materials for the material of the dopant, or may be partially contained. Mu_material=Material can be contained in the main body. The dopant material can control the luminescent color. If the change is over the layer, the cut material can be used to destroy the county, so it is difficult to overdo it. Under the weight (4), it is better to use less than 10% by weight in the main material. _937 Μ 掺杂 掺杂 掺杂 掺杂 掺杂 , 2012 2012 2012 2012 2012 2012 It is formed by co-evaporation with the host material, and may be simultaneously subjected to steaming at the same time as the main material is fed. The formula (1) has a hydrazine. The compound of the scaffold has an aromatic heterocyclic group containing electron-accepting nitrogen, so it can also be used as an electron transporting material, but it is preferably used as a luminescent material because of its high luminescent property. Further, since the light-emitting element material of the present invention exhibits strong luminescence in the blue-green to red region (5 〇〇 to 68 〇 nm region), it can be preferably used as a blue-green to red luminescent material. Further, when used as a host-dopant-based luminescent material, a compound having a carbazole skeleton represented by the formula (丨) can also be used as a dopant material, but since the film is excellent in stability, it can be compared. Good land is used as the main material. When a compound having a carbazole skeleton represented by the formula (1) is used as a host material, green light emission or red light emission of high color purity can be obtained with high luminous efficiency depending on the kind of the dopant to be used in combination. In addition to the compound having a carbazole skeleton represented by the formula (1), a luminescent material may be a condensed ring derivative such as ruthenium or osmium previously known as an illuminant, and represented by bis(8-hydroxyquinoline)aluminum. a metal chelating 8-hydroxyquinolinone compound, a bis-vinyl fluorene derivative or a diphenylethylene derivative such as a diphenylethylene derivative, a bismuth bios, a (four) bacterium, and a coumarin Derivatives, H derivatives, squama derivatives, ♦ 瑞 derivatives, cyclopentadienyl derivatives H derivatives n and (9) pour organisms, dibenzopyrene fascinating objects, ah (four) enchantments, And a polyphenylene acetylene derivative, a polyparaphenyl derivative, and a phenanthrene derivative of the polymer system 100121937 41 201211003, etc., but are not limited thereto. 3 The main material in the syllabus is not limited to one of the compounds having the card satin frame represented by the general formula (1), and may be mixed with several compounds of the present invention having the compound of the moon wood, or a kind of The above other host materials are used in combination with the compound of the card skeleton in this month. The material which can be mixed is not particularly limited, and a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, anthracene, chopsticks, copper tetraphenyl, hydrazine, or hydrazine can be used: or a living organism thereof; N,_Dinaphthyl-N,N'-diphenyl_4,4,-diphenyl-u, February female aromatic and other amine-free derivatives; represented by three (8_ 啥 啥 啥 吕 (10) Gold chelating 8' base ketone compound; bisstyryl derivative such as distyrylbenzene derivative; tetraphenylbutadiene derivative; (4) biological; fragrant mutual=he biological "f 嗤 嗤Line; scales and sputum storage organisms; surinic acid derivatives '· cyclopentaene biosynthesis, pyridinium and pyrrole derivatives; thiadiazole pyridinium organisms, a stupid and furan derivatives; carbazole derivatives ; carbazole derivatives. _ ° well Ho; and polyphenylene block of polymer system, poly-peptanthene biopolyfluorene derivatives, polyvinyl carbazole derivatives, polyphene derivatives, etc. The hydrazine is not particularly limited. Among them, as the main body used for the luminescence of the luminescent layer, a metal S compound, a dibenzo sulphur derivative, and a glaze may be preferably used. a derivative, a substance, etc. Z-butyl as a triplet luminescent material used as a dopant material preferably contains a substance selected from the group consisting of silver (8), ruthenium (Ru), palladium (Pd), #(Pt), 锇 ( 0s), and 铢(10)) The metal complex of at least one metal in the group of 100121937 42 201211003. The ligand preferably has a phenyl "backbone or a phenyl n pure skeleton. However, it is not limited to these, and an appropriate complex can be selected according to the desired luminescent color, element performance, and relationship with the host compound. Specifically, three '(2-phenylene)-based silver can be mentioned. Complex, triad-porphinyl (tetra)-based 鈒 鈒 • 、, three {2_(2·benzophenenyl))} silver complex, phenyl phenyl hydrazine , three (2_stupyl benzo-and-sodium) silver complex, tribendivin yttrium complex, bis(2-phenylindole) (ethyl acetonide) silver complex, double {2·(2 singular, fixed base} silver complex, bis (2♦ benzoquinone (tetra))} (ethyl acetate) silver complex, bis(2-phenylbenzopyrene) B-Bing C-complex, bis(2·Benzene (tetra), bis(B) complex, diphenyl啥琳酿丙嗣)鈒 合物 complex, double {2-(2,4_difluorophenyl(tetra)yl}(乙醒丙_) = material non: base wheel complex, (four) thiophene丙早(U0-啡琳胸胸合合,{三(嗟指甲醒三气phenyl-(10)非琳(10)合合,{三(1,3_二苯#丙二哪(U0-非Lin)} 铕 合物 、, triethyl hydrazine acetone 轼 complex, etc. It is also better to use the Japanese special 丨 4 main ^ = agent. Not limited to these, it is easy to obtain high efficiency luminescence = It is preferable to use a silver complex or a starting complex. τ is used as a host material. The compound represented by the formula (1) having a oxazole bone enthalpy and a dopant material is contained only in a type t. The material may be used in the light-emitting layer 100121937 or in combination of two or more. When two or more triplet luminescent materials of 201220123 are used, it is preferred that the total weight of the dopant material is 20% by weight or less based on the host material. Further, in the light-emitting layer, in addition to the host material and the triplet light-emitting material, a third component for adjusting the balance of the carrier in the light-emitting layer or for stabilizing the layer structure of the light-emitting layer may be further included. Among them, as the third component, a material which does not interact with the host material containing the compound having a carbazole skeleton and a dopant material containing a triplet luminescent material can be selected. The preferred host and dopant in the triplet light-emitting system are not particularly limited, and specific examples thereof are as follows. [化 28] 100121937 44 201211003

100121937 45 201211003 [Chem. 29]

In the present invention, the term "electron transfer layer" refers to a layer in which electrons are injected from a cathode to transport electrons. For the electron transport layer, it is desirable that the electron injection efficiency is high, and the electrons of the person can be efficiently transported. S, this requires a good round of the following substances, that is, the affinity of the feron is better than A, and the electrons are relatively large, and the stability is 100121937 46 201211003. It is difficult to manufacture and use when it is used. Hey. Further, in the case where the film thickness is thick, the seven or eight groceries are particularly easily crystallized to deteriorate the film quality, so that the compound having a full capacity of the compound is preferably used. However, in the case of a molecule having a stable membrane quality, as long as the electron transport layer mainly functions as a hole that can be balanced with the transport of electrons, it does not recombine and flows to the cathode side to perform I/stop from the anode. The electrons that are not so high are composed of materials with higher electron transporting ability. The effect of the material is as follows: The electron transport layer of the invention also contains a blocking layer that can effectively prevent the movement of the hole as a synonym. The multi-action hole is used as an electron transport-like electron transport material, and in addition to the compound material of the general formula (1) which does not have a material skeleton, it can also be a polycyclic aromatic derivative such as ^, I, and the like, and 4 4, _双丨_t '' U-bridge m double ("本基乙喊" Lian Bu is represented / Xiji with aroma ring derivatives; pure or biphenyl __ biological; oxidized broken organism; three (8_ Jing蝴 _1 } } 等 ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; In terms of reducing the driving cap and obtaining high-efficiency luminescence, it is preferably composed of an element selected from the group consisting of stone counter, strontium, nitrogen, oxygen, stagnation, and can, and has electron-containing nitrogen. a compound having a heteroaryl ring structure (hereinafter referred to as "specific hybrid"). A heteroaryl ring having an electron-accepting nitrogen has a high electron affinity, and 100121937 201211003 is excellent in sub-delivery energy, and is used for The electron transport layer towel can reduce the riding voltage of the light-emitting element. As a material of the material, it can be exemplified by benzene-flavored saliva. , benzoacyl derivatives, benzopyrene derivatives, etc., such as di-salt derivatives, quinone derivatives, tri-salt derivatives, kiss-wheel organisms, which derivatives, derivatives, derivatives, and derivatives Objects, joint bites, or triplets (four) and other oligo shouts '噎 derivatives and bite derivatives are used as hide-and-beats. For their towels, for the purpose of reading Wei, it is better to use three pings. Phenylbenzimidyl L-based benzene derivative, U-bis[(4_t-phenylphenyl)u, 4n-based] phenyl dinon derivative, N-naphthyl-2, 5-m recognition three materials three wow charm, 29_ dimethyl sentence · biphenyl - U0 - morphine or u · double (1, (four) material base) benzene and other morphine derivatives, 2, 2, - double (stupid And attached to Lin _2_ base) noisy snail (four) benzopyrene: Yan,, 2,5-double (6'_(2,... Earthstone heterodiene) (4) enchantment, 1,3•double 22 A combination of three (four) reading organisms, double (1 pin ortho-diyl) phenyl phosphine oxide special sales. Sacrifice 2 force /, medium ^ good is a specific heteroaryl compound with ttf frame, with a specific compound of the tibia 2 and a specific heteroaryl group having a light carrier = a preferred electron transporting material, and The following is specifically exemplified, and the following examples are given. Further, the following έ (10) is based on the appearance group, the aryl group or the aryl group: the similarity of the _^ ” square group substituted derivative, 1, 3, 7 Alkane 100121937

4S 201211003 Group, aryl or heteroaryl substituted 生物,1> 6-membered aryl, aryl or heteroaryl substituted derivative, uo substituted by alkyl, aryl or heteroaryl Derivatives and the like can also be exemplified as preferred examples. [化30]

The above-mentioned electron transporting material may be used singly or in combination of two or more kinds of the above-mentioned electron transporting materials, or may be used by mixing one or more kinds of other electron transporting materials in the above-mentioned electron transporting materials. Further, it may be used by mixing with a metal such as an alkali metal or an alkaline earth metal. The free potential of the electron transporting layer is not particularly limited, and is preferably 5.8 eV or more and 8.0 eV or less, more preferably 6 〇eV or more and 7.5 eV or less. The method for forming the respective layers constituting the light-emitting element may be, for example, resistance heating vapor deposition, electron beam evaporation, sputtering, molecular layering, or coating, and is not particularly limited. Usually, in terms of device characteristics, resistance is preferred. Heating evaporation or electron beam evaporation. The thickness of the organic layer is also determined by the resistance value of the luminescent material, and is not limited. It is preferably 1 to 1000 nn. The thickness of the luminescent layer, the electron transporting layer, and the hole transporting layer is preferably 1 nm or more and 200 nm or less. More preferably, it is 5 nm or more and 100 nm or less. The light-emitting element of the present invention has a function of converting electrical energy into light. Here, as electrical energy, DC current is mainly used, and pulse current or alternating current can also be used. The current value and voltage value are not particularly limited. When considering the power consumption or life of the component, the maximum brightness should be selected with the lowest possible energy. The light-emitting element of the present invention can be preferably used, for example, as a display which is displayed in a matrix and/or a segment. The matrix method is a set of characters or images in which the pixels to be displayed are two-dimensionally arranged in a lattice shape or indented. The shape or size of the pixel depends on the application. For example, in the computer, monitor, TV image and 100121937 50 201211003 w hanging use - the edge of the _ below the quadrilateral pixel, the level of the stupid display panel of the large display, the use of - side for the face, can be 1 . In the case of monochrome display*, pixels of the same color are arranged and displayed in pixels of red, green, and blue when the color is not displayed. Two ^, typically triangular and striped. Moreover, the driving method of the matrix may be any one of a line sequential driving method or an active matrix. Although the line sequence drive is simple in structure, (4) the active matrix is superior in considering the action characteristics, so it must also be used separately. The segment code method in the case of the present invention forms a pattern in such a manner as to determine the information determined by the first determination, and causes the region to be determined according to the arrangement of the pattern. For example, a time in a digital clock or a thermometer, a temperature display, an operation state display such as an audio device or an induction cooker, and a panel display of a car can be cited. And the above matrix display and segment code display can also coexist in the same panel. The light-emitting element of the present invention can also be preferably used as a backlight for various machines and the like. The backlight is mainly used for the purpose of improving the visibility of the display I which does not emit light by itself. (4) Liquid crystal display (four), clock, audio device, automobile panel, display panel and logo. The characteristic liquid crystal display device, particularly the backlight for researching a thinned computer use, can preferably use the light-emitting element of the present invention, and can provide a thinner and lighter backlight than the conventional one. [Examples] Hereinafter, the present invention will be described by way of Examples, but the present invention is not limited by the Examples. Further, the numbers of the compounds in the following examples are 100121937 51 201211003, which refer to the numbers of the compounds described above. [Synthesis Example 1] Synthesis of Compound [59] Under a nitrogen stream, a mixed solution of 32.0 g of carbazole, 93.13 g of anhydrous ferric chloride [III] and 400 ml of chloroform was stirred at room temperature for 22 hours. The mixed solution was placed in 1000 ml of decyl alcohol, and after stirring for 1 hour, it was filtered. To the obtained powder, tetrahydrofuran 6 〇〇 ml was added and refluxed for 30 minutes, and then filtered to remove insoluble matter. After evaporation, it was dissolved in 100 ml of DMI (1,3-Dimethyl-2-Imidazolidinone) by heating, and then it was 5 . Recrystallization under the armula gave 9 Η, 9 Ή-3,3,-bicarbazole 14.0 g. Then, under nitrogen flow, a mixed solution of 9Η, 9Ή-3,3,-bicarbazole 14.0 g, iron stupid 8.59 g, nitro stupid 4〇〇m copper powder 5.72 g and potassium carbonate 12.44 g was 18〇 . The mixture was heated and stirred for 4 hours. After cooling to room temperature, the nitro group was removed by distillation under reduced pressure and then purified by silica gel chromatography. After vacuum drying, 'yield 9·phenyl-9Η,9Ή·3,3,-bicarbazole 5.59 g was obtained. . Then, a mixed solution of 12.5 g of melamine gas and 12 5 g of tetrahydrofuran was cooled to 〇〇C under a nitrogen stream, followed by stirring. To the mixed solution, phenylmagnesium bromide (32% in THF) was gradually added dropwise to 1 5.6 g over 1 hour and a half. At this time, the temperature in the system is maintained below 15 °C. After the dropwise addition, 80 ml of toluene was added in half at room temperature and cooled to 0 °C. After 12 minutes, 12%HC1 was slowly added to the liquor of °H's S. At this time, the temperature inside the system is maintained below 30 C. Thereafter, water was injected and extracted with benzene. The organic layer was washed twice with water 100121937 52 201211003, dried over magnesium sulfate, and evaporated. The obtained concentrate was purified by Shih Hose column chromatography. After vacuum drying, chloro-4,6-diphenyl-1,3,5-tris was obtained. Well 8.15 §. Then, a mixed solution of 55% sodium hydride 0.40 g and dehydrated DMF (dimethylf〇rmamide) 30 ml was stirred at room temperature under a nitrogen stream. To the mixed solution, a solution obtained by dissolving 9.59 g of 9-phenyl-9Η,9Ή-3,3,-bicarbazole in 100 ml of dehydrated DMF was gradually added dropwise, and the mixture was stirred for 1 hour. Thereafter, 2_chloro-4,6-diphenyl-1,3,5-tri" well 3.52 g was dissolved in dehydrated DMF 130 ml, and slowly added dropwise, and then stirred for 3 hours and a half, and then water was poured into 300 ml. After stirring for 1 hour, filtration was carried out. The obtained solid was heated and washed with 1.5 ml of methanol, and then filtered. The obtained solid was purified by silica gel column chromatography, and then recrystallized twice from a mixed solvent of tetrahydrofuran and methanol, and dried in vacuo to give a white powder of 4.28 g. The results of h-NMR analysis of the obtained powder were as follows. The white crystals obtained above were confirmed to be the compound [59J. iH-NMR (CDC13 (d = ppm)): 7 32 736 (m, 1H), 7.45_ 7.55 (m, 5H), 7.63 - 7.69 (m, lljj^ ? ^ ^ 7 g5 (m, 1H), 7.99 -8.01(m,lH), 8.20-8.21(t,lH),8 25 8.53 (m,lH), 8.40- 8.41(d,lH),8.53 - 8.54 (d,lH),8 79 -8.8l ( m, 4H), 9.21 - 9.23 (d, 1H), 9.26 - 9.27 (d, 1H). Further, the compound [59] is an oil-diffusing fruit, which is about 320° at a pressure of lxl (at a pressure of T3 Pa). C was used as a light-emitting device material after sublimation purification. 100121937 53 201211003 HPLC (High Performance Liquid Chromatography) purity (area % at a measurement wavelength of 254 nm) was 99.8% before sublimation purification, and 99.9% after sublimation purification. 2] Synthesis of compound [44] under nitrogen flow, so that 2,4,6-trichloropyrimidine bite 10 g, phenylboronic acid 13.3 g, 2 Μ sodium carbonate aqueous solution! 63.5 ml, 1,2-dimethoxyl 545 ml of alkane and bis(trisylphosphine) gasification The mixture of (II) was refluxed for 2 hours. After cooling to room temperature, extraction was carried out with benzene. The organic layer was washed twice with water and then with magnesium sulfate. After drying, evaporation is carried out by means of gel column chromatography, and the obtained concentration is concentrated. Purification was carried out, and after vacuum drying, 6.66 g of 2-chloro-4,6-diphenylpyrimidine was obtained. Then, under a nitrogen stream, at room temperature, 9-phenyl-9H, 9H-3,3-hydrazine was added. Mixing solution of 4.08 g of oxazole, 2.93 g of 2-chloro-4,6-diphenylpyrimidine, sodium tributoxide 丨.35 g, and dehydrated ortho-xylene 100 ml. Add three (two) to the mixed solution. After substrate palladium (27 mg) and 0.16 g of tri-t-butyltetrafluoroborate, the mixture was heated and stirred at 140 ° C for 1 hour. The mixed solution was directly filtered and evaporated. After adding methanol 2 〇〇 ml 'reflow for 2 hours', it was filtered, and the obtained 111 body was purified by vacuum column chromatography to obtain 5.7 g of a pale yellow powder. The results of the NMR analysis are as follows. 'It is confirmed that the pale yellow crystal obtained above is the compound [44]. 100121937 54 201211003 H-NMR (CDCI3 (d = ppm)) · 7.32 - 7.35 (m, η 42 7.67 (m (16, H), 7. 8 % (m 4H), 8.42 8.43 (d, 1H), 8.52 - 8.53 (d, 1H), 9.05 - 9.07 (d, 1H), 9.10 - 9.11 (d, 1H). Further, the compound [44] was used as a light-emitting device material jplc purity (area % at a measurement wavelength of 254 nm) after sublimation purification at about 330 ° C using an oil diffusion pump under a pressure of 〇1〇·3 Pa. It was 99 8% before purification, and 99.9% after sublimation purification. [Synthesis Example 3] Synthesis of Compound [18] Under a nitrogen stream, 4.0 g of 2,4,6-trichloropyridine, phenylboronic acid 5 3 gi Μ sodium carbonate aqueous solution 87ird, 1,2-dimethoxyethane 1 〇 8 ml of a mixed solution of bisphenylphosphine)palladium dichloride (11) 290 mg was refluxed for 3 hours. After cooling to room temperature, extraction was carried out with toluene. The organic layer was washed twice with water, dried with magnesium sulfate, and evaporated. The obtained concentrate is purified by a ruthenium column chromatography, and after vacuum drying, 4_gas-2,6-diphenyl group is obtained, and 2 7 g 0 is bitten, and then under a nitrogen stream, at room temperature. 9-phenyl-9H,9'H-3 3,-terbeazole 3.0 g, 4-gas-2,6-diphenylpyridine 2.15 §, third butadiene sodium hydrazine 99 g, dehydrated o-xylene A mixture of 73 ml was stirred. To the mixed solution of tritium (dibenzylideneacetone) dipalladium (0) 0.13 g, tri-t-butyltetrafluoroboric acid 100121937 55 201211003 scale 58 mg, and heat-mixed at 140 ° C for 6 hours. After the mixed solution was directly passed through, the evaporation was carried out. After adding 2 ml of turmeric methanol, ¢7 flow for 2 hours, cooling to room temperature, and carrying out the furnace. The obtained solid was purified by silica gel column chromatography, and dried in vacuo to give 2.9 g of pale yellow powder. The W-NMR analysis results of the obtained powder were as follows. The yellowish powder obtained above was confirmed to be the compound [18]. 'H-NMR (DMSO-d6 (d == ppm)) . 32 _ y 36 (m, 1H), 7.40 - 7.60 (m, 12H), 7.68 - 7.?7 (m, 5Η), 7.83 - 7.84 (d, 1H), 7.91 - 7.93 (m, 1H), 7.95 - 7.97 (m, 1H), 8 29 (s, 2H), 8.34 8.37 (m, 4H), 8.40 _ 8.41 (d, 1H), 8 44 _ 8 46 (d, 1H), 8.73 _ 8 75 (m, 2H). Further, the compound [18] was subjected to sublimation purification under a pressure of 1×1 pa -3 Pa to be used as a light-emitting element material ^hplc purity (measured at an area of 254 nm at a wavelength of 254 nm). It is 99 8% before sublimation purification and 99.9% after sublimation purification. [Synthesis Example 4] Synthesis of compound [3 8] under a nitrogen stream at room temperature, 蚪Λ w to 9-phenyl_9H, 9 , H-3,3,-bicarbazole 3.03 §, 1 preparation 3,5_di-benzene benzene U4 δ, third butyl oxide nano-lG g, dehydrated o-xylene 7 〇ml mixed solution for mixing. Adding tris(diheptylacetone) di I bar (0) 85 mg and tri-t-butyltetrafluorotetrazate meal size % post after mixing in a mixed solution for 4 hours under heating at TC. The mixed solution was directly After the 遽 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , - 吟 吟 0 sit 3.29 g. Then, under a stream of air, make 9_(3,5-dichlorophenyl)_9, _phenyl-9H, 9H-3,3 - together ten 3.29 g, 3" ratio 15 g, 127 M potassium citrate solution 21 M_dioxin 3 〇 卜 三 三 (diphenylidene acetonide) dipalladium (0) 136 mg and di-hexyl phosphine 79 mg mixed solution was refluxed for 12 hours. After cooling to room temperature, extraction with benzene was carried out. The mixture was washed twice, dried over magnesium sulfate, and evaporated. The obtained concentrate was purified by silica gel column chromatography, and dried in vacuo to give a pale yellow powder of 24 g. The yellowish powder obtained above was confirmed to be the compound [38] as described below. 1H-NMR (CDCl3 (d = ppm)): 7.3l - 7.38 (m, 2H), 7.43 - 7.57 (m, 8H), 7.61 - 7.66 (m, 5H), 7.77 - 7.83 (m5 2H), 7.88 > 7.91 (m, 3H), 8.01 - 8.04 (m, 2H), 8.23 - 8.28 (m, 2H), 8 47 - 8.49 (m , 2H), 8.69 - 8.70 (m, 2H), 9.01 - 9.02 (d, 2H). Further, 'this compound [38] is an oil diffusion pump, under the pressure of ixi〇-3 Pa, about 32 〇 The purity of β Ηριχ used as a light-emitting element material after sublimation purification at °C (% of area under measurement wavelength of 254 nm) was 99.8 〇/0 before sublimation purification, and 99.9% after purification by sublimation. [Synthesis Example 5] 100121937 57 201211003 Compound [ 224] The synthesis was carried out under a nitrogen stream to make 5.0 g of 3,6-dibromocarbazole, 2.96 g of phenyloxazole-3-bromide, 267 mg of palladium acetate, 234 mg of tris(2-methylphenyl)phosphine, and 1 μ of carbonic acid. A mixed solution of 30 ml of potassium aqueous solution and 80 ml of dimercaptoacetic acid was refluxed for 2 hours. After cooling to room temperature, extraction was carried out with 100 ml of toluene. The organic layer was washed twice with 50 ml of water. After drying with sulfuric acid, it was evaporated. The obtained concentrate was purified by silica gel column chromatography, and dried under vacuum to give 6-bromo-9'-phenyl-9 oxime, 9 Ή-3,3,-bicarbazole 3.48 g. Then, under a nitrogen stream, 6-bromo-9'-phenyl-9Η, 9Ή-3,3'-bicarbazole 3.48 g, 3-pyridine boronic acid 1.32 g, bis(triphenylphosphine)palladium dichloride (11) A mixed solution of 100 mg of a 1 Μ sodium carbonate aqueous solution of 14 m of 1,4-dioxane 35 ml was refluxed for 2 hours. After cooling to room temperature, extraction was carried out with 50 ml of toluene. The organic layer was washed three times with 20 ml of water, dried with magnesium sulfate, and evaporated. The obtained concentrate was purified by hydrazine column chromatography and dried in vacuo to give 9-phenyl-6-(pyridin-3-yl)-9 oxime, 9 Ή-3,3'-bicarbazole 2.1. g. Then, a mixed solution of 55% sodium hydride 231 mg and dehydrated DMF 10 ml was stirred at room temperature under a nitrogen stream. The dropwise addition of 9,-phenyl-6-(pyridin-3-yl)-9H,9'H-3,3'-bicarbazole 2·1 g to the dehydrated DMF 15 ml was slowly added dropwise to the mixed solution. The solution in the mixture was stirred for 3 hours. Thereafter, '2-gas-4,6-diphenyl-1,3,5-three 41.20 g was dissolved in 25 ml of dehydrated DMF, and slowly added dropwise, and then stirred for 2 hours and a half, then [injected water 50 ml] After stirring for 1 hour, filtration was carried out. The solid obtained was refluxed to 1 small 100121937 58 201211003 in 5 mL of methanol, cooled to room temperature, and then filtered. The obtained solid was purified by a celite column chromatography, and then recrystallized from &lt The result of h-NMR analysis of the obtained powder was as follows. The white crystal obtained by the above was confirmed to be the compound [224]. • iH-NMR (CDCl3 (d = ppm)): 7.31_7.34 (m, lH), 7.39- 7.41 (m, 1H), 7.44 - 7.45 (m, 2H), 7.49 - 7.52 (m, 2H), 7.60 - 7.67 (m, 10H), 7.79 - 7.81 (m, 2H), 7.94 - 7.96 (m, 1H), 8.02 -8.04 (m, 1H), 8.23 - 8.25 (d, 1H), 8.300 - 8.303 (d , 1H), 8.370 -8.373 (d, 1H), 8.495 - 8.498 (d, 1H), 8.62 - 8.63 (t, 1H), 8.72 -8.75 (m, 4H), 9.040 _ 9.043 (d, 1H), 9.18 - 9.23 (m, 2H). Further, the compound [224] was used as a light-emitting device material by sublimation purification at about 360 ° C under an oil diffusion pump using an oil diffusion pump. HPLC purity (measurement area % at a wavelength of 254 nm) It is 99.7% before purification by sublimation and 99.8% after purification by sublimation. [Example 1] A glass substrate (11 □, sputtered product manufactured by Geomatec Co., Ltd.) in which an ITO transparent conductive film was deposited at 125 nm was cut into Etching was carried out at 38×46 mm, and the obtained substrate was ultrasonically cleaned with “Semic〇Clean 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, and then washed with ultrapure water. The substrate was prepared immediately before the device was fabricated. The UV-ozone treatment was performed for 1 hour, and it was placed in a vacuum vapor deposition apparatus, and the exhaust gas was 100121937 59 201211003 until the degree of vacuum in the apparatus was 5 χ 10_4 Pa or less. The copper phthalocyanine was first vapor-deposited by a resistance heating method at 10 nm. 4,4'-bis(N-(l-naphthyl)-N-phenylamino)biphenyl 50 nm as a hole injecting material. Then, as a host material, compound [59], and as a dopant Material D-1 becomes doped concentration 10 The thickness was reduced to a thickness of 40 nm as a light-emitting material, and then a thickness of 20 nm as shown below was used as an electron transporting material. Then, after steaming the IS 0.5 nm, steaming was carried out. The 70 nm is used as the cathode to make a 5×5 mm square element. Here, the film thickness refers to the display value of the quartz oscillation type film thickness monitor. The light-emitting element is driven at 10 mA/cm 2 DC, and the luminous efficiency is obtained. High-efficiency green light emission of 20.0 lm/W. The light-emitting element was continuously driven at a direct current of 10 mA/cm2, and as a result, the luminance was half-decreased after 2000 hours.

(D-1) (E-1) 100121937 60 201211003 A light-emitting device was produced in the same manner as in Example 1 except that H-1 represented by the following formula was used as a host material. The light-emitting element was driven at a direct current of 10 mA/cm2, and as a result, green light having a luminous efficiency of 10.4 lm/W was obtained. The light-emitting element was continuously driven at a direct current of 10 mA/cm2, and as a result, the luminance was half-decayed after 400 hours. [化32]

[Comparative Example 2] A light-emitting device was produced in the same manner as in Example 1 except that H-2 represented by the following formula was used as a host material. The light-emitting element was driven at a direct current of 10 mA/cm2, and as a result, green light having a luminous efficiency of 19.1 lm/W was obtained. The light-emitting element was continuously driven at a direct current of 10 mA/cm2, and as a result, the luminance was half-decayed after 300 hours. [化33]

(H-2) [Comparative Example 3] A light-emitting device was produced in the same manner as in Example 1 of the Japanese Patent Application No. 100121937 61 201211003, except that H-3 represented by the following formula was used as the host material. The light-emitting element was driven at a direct current of 10 mA/cm2, and as a result, green light having a luminous efficiency of 12.3 lm/W was obtained. The light-emitting element was continuously driven at a direct current of 10 mA/cm2, and as a result, the luminance was half-decayed after 700 hours. [34]

[Comparative Example 4] A light-emitting device was produced in the same manner as in Example 1 except that H-4 represented by the following formula was used as a host material. The light-emitting element was driven at a direct current of 10 mA/cm2, and as a result, green light having a luminous efficiency of 11.0 lm/W was obtained. The light-emitting element was continuously driven at a direct current of 10 mA/cm2, and as a result, the luminance was half-decayed after 700 hours. [化35] 100121937 62 201211003

[Comparative Example 5] A light-emitting device was produced in the same manner as in Example 1 except that H-5 represented by the following formula was used as a host material. The light-emitting element was driven at a direct current of 10 mA/cm2, and as a result, green light emission with a luminous efficiency of 9.0 lm/W was obtained. The light-emitting element was continuously driven at a direct current of 10 mA/cm2, and as a result, the luminance was half-decayed after 700 hours. [化36]

(H-5) [Example 2] A light-emitting device was produced in the same manner as in Example 1 except that the compound [44] was used as the host material. The light-emitting element was driven at 10 mA/cm2 of direct current, and as a result, high-efficiency green light emission with a luminous efficiency of 21.0 lm/W was obtained. The light-emitting element was continuously driven with a direct current of 10 100121937 63 201211003 mA/cm2, and as a result, the luminance was half-decayed after 2200 hours. [Example 3] A light-emitting device was produced in the same manner as in Example 1 except that the compound [62] was used as the host material. The light-emitting element was driven at a direct current of 10 mA/cm2, and as a result, a high-efficiency green light emission having a luminous efficiency of 19.2 lm/W was obtained. The light-emitting element was continuously driven at a direct current of 10 mA/cm2, and as a result, the luminance was half-decayed after 1500 hours. [Example 4] A light-emitting device was produced in the same manner as in Example 1 except that the compound [18] was used as the host material. The light-emitting element 'crust was driven at 10 tnA/cm 2 DC to obtain high-efficiency green light with a luminous efficiency of 19.0 lm/W. The light-emitting element was continuously driven at a direct current of 10 mA/cm2, and as a result, the luminance was half-decayed after 1300 hours. [Example 5] A light-emitting device was produced in the same manner as in Example 1 except that the compound [38] was used as the host material. The illuminating element was driven with a direct current of 1 〇 mA/cm 2 as a result of obtaining a high-efficiency green luminescence with a luminous efficiency of 19.0 lm/W. The light-emitting element was continuously driven at a direct current of 10 mA/cm2, and as a result, the luminance was half-decayed after 1300 hours. [Example 6] A light-emitting device was produced in the same manner as in Example 1 100121937 64 201211003 except that the compound [224] was used as the host material. The light-emitting element was driven at 10 mA/cm2 of direct current, and as a result, high-efficiency green light emission with a luminous efficiency of 23.0 lm/W was obtained. The light-emitting element was continuously driven at a direct current of 10 mA/cm2, and as a result, the luminance was half-decayed after 1800 hours. r The results of Examples 1 to 6 and Comparative Examples 1 to 5 are shown in Table 1. [Table 1] host material dopant material luminescent color luminous efficiency (lm/W) luminance half-life time (8) Example 1 Compound [59] D-1 Green 20.0 2000 Example 2 Compound [44] D-1 Green 21.0 2200 Example 3 Compound [62] D-1 Green 19.2 1500 Example 4 Compound [18] D-1 Green 19.0 1300 Example 5 Compound [38] D-1 Green 19.0 1300 Example 6 Compound [224] D-1 Green 23.0 1800 Comparative Example 1 H-1 D-1 Green 10.4 400 Comparative Example 2 H-2 D-1 Green 19.1 300 Comparative Example 3 H-3 D-1 Green 12.3 700 Comparative Example 4 H-4 D-1 Green 11.0 700 Comparative Example 5 H-5 D-1 Green 9.0 700 [Examples 7 to 13] The same materials as in Example 1 were used except that the materials described in Table 2 were used as the host material, the dopant material, and the electron transport material. The method produces a light-emitting element. The results are shown in Table 2. Further, in Table 2, E-2 is a compound shown below. [化37] 100121937 65 201211003

(E-2) [Table 2] Host material dopant material Electron transport material Luminescent color Luminescence efficiency (lm/W) Luminance half-life time (h) Example 7 Compound [59] D-1 Compound [59] Green 23.0 2500 Example 8 Compound [224] D-1 Compound [224] Green 24.0 2300 Example 9 H-4 D-1 Compound Green 20.0 1800 Example 10 H-5 D-1 Compound [224] Green 19.0 1900 Example 11 Compound [59] D-1 Ε-2 Green 13.1 900 Example 12 Compound [44] D-1 Ε-2 Green 12.5 950 Example 13 Compound [224] D-1 Ε-2 Green 13.0 900 Comparative Example 6 H- 1 D-1 Ε-2 Green 8.8 600 [Comparative Example 6] A light-emitting element was produced in the same manner as in Example 1 except that the material described in Table 2 was used as the host material, the dopant material, and the electron transport material. . The results are shown in Table 2. [Examples 14 to 18] Light-emitting elements were produced in the same manner as in Example 1 except that the materials described in Table 3 were used as the host material, the dopant material, and the electron-transporting material. The results are shown in Table 3. In addition, in Table 3, E-3, E-4, E-5, E-6, and E-7 are the compounds shown below. [化38] 66 100121937 201211003

(E-7) 100121937 67 201211003 [Table 3] dopant material ΐ-sub-sputum material

Luminous green, green and green (Example 19) Luminous efficiency (lm/W) Luminance half-life (h) 20.0 19.0 T9.0 T9.0 ]0_0 2200 2000 2100 1900 2400 A transparent conductive film of 125 nm is deposited. The glass substrate (Asahi Glass Co., Ltd., 15 Ω/□, electron beam vapor-deposited) was cut into 30×40 mm, and processed into a pitch (residual width of 27G (four) x 32 stripes) by photolithography. The long-side direction is easy to connect with the outer-side electric rolling, and the pitch is extended to 丨27 (opening width (10) 〇 #m). The obtained substrate is made of acetone and ciean56" (trade name, manufactured by Furuuchi Chemical Co., Ltd.). Ultrasonic cleaning for 15 minutes, X-ray, and water were washed. Then, it was washed with isopropyl alcohol for 15 minutes, and then immersed in hot methanol for 15 minutes, and dried. After a few hours of UVH treatment, and placed in a vacuum U device, 'exhaust until the vacuum in the device becomes 5χ1〇·4 Pa or less. By resistance heating method, first steam 4,4,_ double (N_(p-naphthyl) )_N_phenylamino)biphenyl 15〇nm as The hole is fed with a material. Then, the compound [59] as a host material and (D_l} as a dopant material are vapor-deposited to a thickness of 40 nm so that the doping concentration becomes 10%. The thickness of 20 nm is used as the electron transport material. Here, the film thickness refers to the display value of the quartz forged film thickness monitor of 100121937 68 201211003. Then, the thickness of the 50 kovar (Kgvar) plate is wet (4) The opening of the i6 root (corresponding to the residual width of 5 〇 花 2 υυ m # m) is placed in a vacuum, and the mask is exchanged in a manner orthogonal to the IT0 stripe, so that the r cover is in close contact with the 1το substrate. In this way, the magnet is solidified from the back side, and after vapor deposition of lithium fluoride 〇.5 nm, the aluminum is vaporized by 2 〇〇 nm, and the 掣 邗 χ 32 χ 6 6 dot matrix element. The matrix drives the element 'Result Character display ",, cross-talking (industrial availability) <% of materials, etc., light-emitting element materials useful as luminescent pigments. The light-emitting element material according to the present invention can provide a kind of light-emitting material Higher luminous efficiency A light emitting element emitting invention is excellent in durability of the display element may be used for coexistence, a flat panel display, the present invention is clear, the I member. This and other fields, interior decoration, indicators, signboards, electronic cameras and optical signal generating ,, as squid 10012193769

Claims (1)

201211003 VII. The material of the patent application scope is characterized by containing a compound having a carbazole skeleton represented by the following formula (1), R33 R34^5 36 (1) R31 ^ R38 HAr (R31 to f are respectively selected Free hydrogen, alkyl, cycloalkyl, heterocyclic, dilute ring, alkynyl, alkoxy, thiol, aryl ether, arylsulfanyl, arylheteroaryl, halogen, fluorenyl , silk, tilting group, amine methyl sulfhydryl group, amine group = alkyl group, hydrazine (= 〇) ^, and the group represented by the following formula (7) is a group of aryl or heteroaryl groups; R31 In ～r38, adjacent subunits may form a ring with each other; wherein any of 'R31 to R38' is a group represented by the following formula, and any one of R4i to R49 in the formula (2) a positional group; L is selected from the group consisting of a single bond, an extended aryl group, and a heteroaryl group; and is an aromatic heterocyclic group having an electron accepting nitrogen. R44Rf R46 (2) R4] to R48 are each selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocyclic 100121937 70 201211003 % dilute, block, alkoxy, thiol, aryl, aryl squaring, "hetero a group consisting of a square group, a hydroxyl group, a aryl group, a carboxyl group, an oxo group, a carbamic acid group, a decyl group, and a hydrazine group R50r51; r5〇 and & Shi Ximou. R4]~1?48 a In the base or heterogeneous #, R, the adjacent substituents may form a ring with each other; in R49, the group consisting of a burning group, a square group and a material group H R4 〗 〖R49 ^ free and the general formula (1) Any one of R31 to R38 is connected.) 2. The light-emitting element material according to claim 1 of the patent application, wherein the compound having the carbazole skeleton represented by the formula (1) has the following The compound of the carbazole skeleton, represented by [Chemical 3] (R1 to R14 are each selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocyclic, ethenecycloalkenyl, alkynyl, alkoxy, thiol, aryl fluorenyl, aryl sulphur, aryl a group consisting of a halogen group, a halogen group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an amine group, an amine group, an alkyl group, and a -P(=0)r16r17; R16 and R17 are an aryl group or a heterodiyl group; In R] 4, adjacent substituents may form a ring with each other; Rls is selected from the group consisting of a fluorenyl group, an aryl group, and a heteroaryl group; and L is selected from the group consisting of a single bond, an exoside, and a heteroaryl group. ;HAr is an aromatic group 100121937 71 201211003 heterocyclic group having electron accepting nitrogen. Among them, L-HAr, L-HAr 3. The material of the light-emitting element according to the scope of the patent application is different from R49. 4. The material of the light-emitting element according to item 2 of the patent application is different from R15. 5. If you apply for the special circumstance to the 4th shot - the luminescence of the item, which has the electron accepting nitrogen fang (4) "The base is selected from the base of shouting, 啥琳基, heterogeneous base, and similar" - base, clothing private,. Non-Linki, - (4) base, trifilament, stupid and imi, benzene open base and material (4) base in the group. The material of the light-emitting element according to any one of items 1 to 5, which is substituted by an electron accepting material, is substituted by an alkyl group or an aryl group. ^ 7.----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- In any of the layers between the anode and the cathode, a light-emitting device material of the first to sixth emitters is formed. 8. The light-emitting element of claim 7, wherein the light-emitting element material of any one of claims 1 to 6 is contained in the light-emitting layer. 9. The light-emitting element of claim 7 or 8, wherein an electron transport layer is further present between the anode and the cathode, wherein the electron transport layer comprises 100121937 72 201211003 selected from the group consisting of carbon, hydrogen, nitrogen, oxygen, A compound composed of an element of ruthenium or phosphorus and having a heteroaryl ring structure containing electron-accepting nitrogen. 10. The light-emitting element of claim 7, wherein the light-emitting element material according to any one of claims 1 to 6 is contained in the electron transport layer. 100121937 73 201211003 IV. Designated representative map: (1) The representative representative figure of this case is: None (2) The symbolic symbol of the representative figure is simple: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 1] [Chemical 2] 100121937 (2)