TW200920180A - Organic EL device - Google Patents

Abstract

Disclosed is an organic EL device comprising an anode, a cathode and an organic thin film layer arranged between the anode and the cathode. The organic thin film layer has a fluorescent light-emitting layer containing a fluorescent host and a fluorescent dopant, and a first phosphorescent light-emitting layer containing a first phosphorescent host and a first phosphorescent dopant. When the triplet energy gap of the fluorescent host is expressed as EgfH and the triplet energy gap of the first phosphorescent host is expressed as EgpH1, they satisfy the following relation: EgfH > EgpH1.

Description

200920180 IX. Description of the Invention [Technical Field of the Invention] The present invention relates to an organic EL element. In particular, it relates to an organic EL element having a fluorescent light-emitting layer and a phosphorescent light-emitting layer. [Prior Art] In the past, a plurality of light-emitting layers having light-emitting colors exhibiting mutually different wavelengths have been known, and organic EL elements of mixed color light in which the light-emitting layers are mixed are obtained. For example, a laminated red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer are provided, and an organic EL element in which white light of the light-emitting layer is mixed is obtained. However, the excited state of the organic compound has a state of arousing a single state and a state of arousing a triplet state. The self-excited light of a single state is called fluorescence, and the light of self-excited triplet state is called twilight. Generally, a single state and a triple state are generated at a ratio of 1:3. Among them, in the conventional organic EL device, a fluorescent luminescent material which mainly emits fluorescence is used. In the organic EL device in which such a fluorescent light is emitted, only 25% of the arouses generated by the light-emitting layer generate light, and the remaining 35% of the excited triplet does not emit light and loses activity. Therefore, in order to improve the luminous efficiency of the organic EL element, a neon light-emitting material that emits self-excited triplet light is developed (for example, Document 1: U.S. Patent No. 2002/1 8244 1). For example, a luminescent material that exhibits red luminescence or a luminescence that exhibits green luminescence has been disclosed -5-200920180. However, it is not practical for those who display blue-emitting luminescent materials. It is only suitable for such a luminescent material, and it can also improve the luminous efficiency in the organic of mixed colors. For example, it is known to obtain a white EL element using a fluorescent material which exhibits red to green light emission of a fluorescent material which emits blue light. This improves the luminous efficiency of the entire organic EL element by increasing the amount of red to green light emission. However, in the organic EL device having such a mixed color, the red light-emitting layer is self-excited to emit light in a triplet state, and on the other hand, the blue triplet state does not cause light emission and loses activity. Here, the excited triplet state of the blue light-emitting layer is diffused to the red light-emitting layer, thereby obtaining a red and green light-emitting organic EL (for example, Document 2: WO2006/038020, WO2004/060026, and literature) 4 : nature vol 440 The organic EL device can obtain red light and light by using the energy of the triplet state of the light-emitting blue light-emitting layer, thereby improving the light-emitting efficiency of the entire organic EL device. The EL element is provided by a blue fluorescent red luminescent layer, a green luminescent layer, and a blue luminescent layer. This document is a blue fluorescent luminescence from the blue fluorescent luminescent layer and blue The color fluorescent light-emitting layer evokes a triple red and green light-emitting layer, thereby generating a red-and-green light-emitting triplet state, and obtaining red and green light-emitting light to obtain an EL element material and an illuminating sub-efficiency. ~ The green color of the luminescent layer and the green component have been lost by the green 燐 燐 、 、 、 、 、 、 、 、 、 、 、 、 、 、 hair . The blue -6-200920180 fluorescent light is mixed with the red and green neon light, and the white light is obtained as a whole. However, in the past (Document 4), the main material of the fluorescent light-emitting layer (the agonist layer) and the phosphorescent layer was CBP. Thereby, the triplet energy gap of the main material of the fluorescent light-emitting layer is larger than that of the light-emitting mixture, so that the triplet agonist energy generated by the main material of the fluorescent light-emitting layer is diffused by the calendering blend. However, there is actually a problem that cannot reach the theoretically expected quantum efficiency. Therefore, the present invention has the following constitution for the purpose of improving the energy efficiency of the organic EL element utilizing the triplet diffusion. The organic EL device of the present invention is an organic EL device including an anode, a cathode, and an organic thin film layer between the anode and the cathode, and the organic thin film layer contains a fluorescent main material and a fluorescent light-emitting compound. a fluorescent light-emitting layer of the compound, and a first light-emitting layer containing the first light-emitting main material and the first light-emitting mixture; the triplet energy gap of the fluorescent main material is EgfH, and the first light-emitting main material The triplet energy gap is an organic EL element characterized by 'EgfH>EgpH at EgpH!. In such a configuration, one of the agonist energies generated by the camphor main material moves to the fluorescent blend to emit light. -7- 200920180 And the triplet agonist energy in the agonist energy generated by the fluorescent main material is emitted by moving the first luminescent main material to the first luminescent mixture. In the present invention, the triplet energy gap EgfH of the fluorescent main material is configured to be larger than the triplet energy gap E g ρ Η 1 of the phosphorescent main material. Therefore, it is easy to move the triplet agonist energy from the fluorescent main material to the first fluorescent main material. Thereby, the triplet agonist inactivation ratio in the fluorescent main material is reduced, and the energy efficiency is improved more than in the past. Further, since the excited triplet state of the fluorescent light-emitting layer is diffused to the first fluorescent light-emitting layer, the thickness of the fluorescent light-emitting layer is preferably reduced. For example, the thickness of the fluorescent light-emitting layer is preferably from 5 nm to 20 nm. Further, since the fluorescent light-emitting layer is thinned, the recombination probability of electric charge can be improved, and the effect of increasing the activation efficiency of the excitons can be obtained. In order to increase the probability of agonist formation in the fluorescent light-emitting layer, a hole blocking layer may be provided on the cathode side of the fluorescent light-emitting layer, or an electron blocking layer may be provided on the anode side of the light-emitting light-emitting layer. The fluorescent light-emitting layer may contain not only one type of fluorescent blend but also two or more kinds of fluorescent blends. The first luminescent layer contains not only one type of first fluorene blend, but also two or more types of luminescent binders. In the present invention, EgfH-〇.leV>EgPHi is preferred. By reducing the difference between the triplet energy gap of the first fluorescent main material of the fluorescent main material, the moving efficiency of the excited triplet energy from the fluorescent main material to the first light main material can be improved. 200920180 In the present invention, the second neon light-emitting layer including the second luminescent main material and the second luminescent sub-mixture is provided, and when the triplet energy gap of the second luminescent main material is EgPH2,

EgpH12EgpH2 is preferred. At this time, the phosphorescent layer which is closer to the first luminescent layer than the luminescent layer of the fluorescent luminescent layer is used as the second luminescent layer. When a non-light-emitting layer such as an intermediate layer is provided, it is not necessary to consider the existence of the non-light-emitting layers. Here, a fluorescent light-emitting layer can be disposed between the first light-emitting layer and the second light-emitting layer. At this time, the first neon light-emitting layer and the second neon light-emitting layer have the same distance from the fluorescent light-emitting layer. At this time, the triplet energy gap of the main material of the enamel is used as the first luminescent main material. In the present invention, when the luminescent layer is disposed between the fluorescent luminescent layer and the second luminescent layer, EgpH1 > EgpH2 is preferred. In the above configuration, the second light-receiving layer is provided, and when the triplet energy gap of the second light-emitting main material is the same as the triplet energy gap of the first light-emitting main material, the same effects as those of the above-described invention can be exhibited. Moreover, the triplet energy gap of the second light-emitting main material is smaller than the triplet energy gap of the first light-emitting main material, and the triplet agonist energy moved from the fluorescent main material to the first light-emitting layer is more easily moved to the second light The main material, the first luminescent layer and the second luminescent layer can be illuminated by triplet energy diffusion. Further, since the triplet energy gap of the main material in the order of the first light-emitting layer and the second light-emitting layer -9-200920180 is small, the efficiency of triplet energy diffusion can be improved, and as a whole, Amazingly efficient color mixing components. In the present invention, it is preferred that the triplet energy gap of the fluorescent main material has an E g f Η of 2.76 eV or more. In the present invention, 2.38 eV <EgpH1 < 2.81 eV is preferred. In the present invention, 2.1 eV <EgpH2 < 2.81 eV is preferred. More preferably, it is 2.1 eV < EgpH2 < 2.7 eV. For example, when the fluorescent light-emitting layer is used as blue light, the first green light-emitting layer is used as green light, and the second green light-emitting layer is made to emit red light, a high-efficiency three-wavelength white element can be obtained. In the case where the fluorescent light-emitting layer is provided on the anode side of the fluorescent light-emitting layer, it is preferable that the hole mobility of the light-emitting main material is large. Thereby, the hole injection into the phosphor layer of the agonist generating layer can be easily performed by the detachment of the luminescent layer, thereby increasing the probability of recombination of charges. At this time, the hole mobility of the main material of the calender is 1×χ104~l_〇xl〇6V/cm in the electric field of lxl (T5cm2/Vs or more is preferable. More preferably 10_4cm2/vs or more, especially preferably l〇'3cm2 Further, when the phosphorescent layer is provided on the cathode side of the fluorescent light-emitting layer, it is preferable that the electron mobility of the light-emitting main material is large. Therefore, it is possible to easily perform the glow of the agonist generating layer from the fluorescent light-emitting layer. The electron injection of the light-emitting layer can increase the recombination probability of the charge. At this time, the electron mobility of the main light-emitting material is preferably x4 1.0 1.0×10×2 V/cm, preferably Ixl0_5 cm 2 /Vs or more. More preferably (T4cm2/Vs or more, l (T3Cm2/Vs or more is particularly preferable. -10-200920180 Further, between the fluorescent light-emitting layer and the fluorescent light-emitting layer, the fluorescent light-emitting layer is provided in the intermediate layer of the carrier. When the light-emitting layer is provided on the anode side, the intermediate layer functions as an electron blocking layer, and the affinity level of the intermediate layer is preferably small, for example, preferably smaller than 2.7 eV and smaller than 2.6 eV. More preferably, when the intermediate layer is disposed on the anode side for the fluorescent light-emitting layer The middle layer does not capture the hole (holl), and it is preferable from the viewpoint of injecting the carrier (hole) of the fluorescent light-emitting layer. Therefore, the hole mobility of the intermediate layer is preferably larger. The layer can easily perform hole injection into the phosphor layer of the agonist generating layer, thereby increasing the recombination probability of the charge. At this time, the hole mobility of the intermediate layer is Ι.ΟχΙΟ4~l.〇xl〇6V/cm The electric field is preferably lxl (T5cm2/Vs or more is preferred. l (T4cm2/Vs or more is more preferable, and l(T3Cm2/VS or more is particularly preferable. Similarly, when the intermediate layer is disposed on the cathode side for the fluorescent light-emitting layer, the middle The layer functions as a hole barrier layer, so that the ionization potential of the intermediate layer is preferably larger, for example, preferably larger than 5.6 eV, and larger than 5.8 eV. Further, the intermediate layer is disposed on the fluorescent light-emitting layer. On the cathode side, the intermediate layer does not capture electrons, and it is preferable from the viewpoint of injecting the carrier (electron) to the fluorescent light-emitting layer. Therefore, it is preferable that the intermediate layer has a larger electron mobility. Easily perform electron injection into the phosphor layer of the agonist generating layer, However, the recombination probability of the electric charge can be increased. At this time, the electron mobility of the intermediate layer is preferably x.4~1.0xl06V/cm in the electric field of lxlO_5cm2/VS or more, more preferably l (T4Cm2/Vs or more, especially good 1 (T3cm2/Vs or more. -11 - 200920180 In addition, in the fluorescent light-emitting layer, it is necessary to perform agonist generation.] The light-emitting layer carrier is directly consumed by the calendering blend and is consumed, so it is not good in the phosphorescent layer. It is preferred that the blending concentration of the calender blend is lower. For example, the blending concentration of the phosphorescent blend in the calendering layer is preferably 1% or less, preferably 5% or less. Further, when an agonist is generated in the fluorescent light-emitting layer, when the agonist is to be moved to the luminescent light-emitting layer, the fluorescent light-emitting layer is preferably thin. Further, in order to prevent the movement energy of the phosphorescent layer from the fluorescent layer, it is preferable to have a sufficient thickness. That is, it is preferable that the thickness of the fluorescent light-emitting layer is thinner than the thickness of the light-emitting layer (the thickness of the first light-emitting layer and the second light-emitting layer). However, when a green light-emitting layer is disposed between the fluorescent light-emitting layer and the red light-emitting layer, if all the energy is stopped by the green light-emitting layer, the red light is not obtained, and the green light-emitting layer is preferably thinner. Compared with the fluorescent light-emitting layer, the green light-emitting layer is preferably thinner, and the green light-emitting layer is thinner than the green light-emitting layer. The measurement of the mobility of the carrier (hole, electron) was carried out as follows. A glass substrate (manufactured by Asahi Glass Co., Ltd.) having an ITO transparent electrode of 25 mm x 75 mm x 1.1 mm was ultrasonically washed in isopropyl alcohol for 5 minutes, and then washed by UV ozone for 30 minutes. The cleaned glass substrate was assembled on a substrate holder of a vacuum deposition apparatus, and first, the measurement material was vapor-deposited on the ITO transparent substrate electrode by resistance heating to a film formation of 3 to 5 μηη. Subsequently, metal ruthenium 1 was evaporated to 10 nm on the film to form a translucent electrode. With the element thus fabricated, the electric field strength of 010 to 1 06 V/cm is -12 - 200920180. The carrier (hole, electron) mobility is measured by the (T) 〇ptel Time of Flight measuring device TOF-401. . The laser can use a 3 3 7 nm nitrogen laser. The photocurrent (I)-time (t) curve is plotted in a double logarithmic manner, and the resulting curve is taken as tr, and the mobility μ is obtained by the mobility μ = L2 / (trxV). Here, L represents the sample film thickness, and V is an applied voltage. According to an embodiment of the present invention, the anode film, the cathode, and the organic thin film layer provided between the anode and the cathode are provided on the transparent substrate, and the fluorescent layer is included in the organic thin film layer. The phosphorescent layer, or the fluorescent emitting layer, the first phosphorescent layer, and the second phosphorescent layer. Further, a hole injection/transport layer or the like may be provided between the anode and the light-emitting layer, and an electron injection/transport layer or the like may be provided between the cathode and the light-emitting layer. Next, the main materials constituting the fluorescent light-emitting layer, the first green light-emitting layer, and the second green light-emitting layer will be described in order. In the present invention, the fluorescent main material has a triplet energy gap larger than that of the main material of the first luminescent layer and the second luminescent layer. When the luminescent color of the first luminescent layer is green, the triplet energy gap of the fluorescent main material is preferably 2_76 eV or more. Specific examples of the fluorescent main material include the following. For example, examples of the oxazole derivative include compounds represented by any one of the following formulas (1 0 1 ) to (1 〇 5 ). -13- 200920180

• · · (lm)

In particular, the compound represented by the above formula (1 (Η) or (1 0 3 ) is preferably used as the main material for calendering. -14 - 200920180 The above formula (1 0 1) may be any of the following structures. .

Examples of the above formula (1 〇 3 ) include the following structures. -15- (103’ )200920180

(103,’ )

Among these, a compound represented by the above general formula (101') or (103') is particularly preferred. In the formulae (101) to (104), R1 to R7 each independently represent a hydrogen atom, a halogen atom, and a carbon number of 丨~4〇 (preferably, a carbon number of 1 to 30) which may have a substituent, and may have a substitution. The heterocyclic group having a carbon number of 3 to 3 Å (preferably having a carbon number of 3 to 20) may have a substituent having a carbon number of 1 to 4 Å (preferably having a carbon number of 1 to 30), and an S* - an aryl group having a carbon number of 6 to 40 (preferably having a carbon number of 6 to 30) having a substituent, and a carbon number of 7 to 4 Å (preferably a carbon number of 7 to 4) which may have a substituent. Aralkyl anthracene having a carbon number of from 2 to 40 (preferably having a carbon number of 2, an aryloxy group of 3 to 40 (preferably having a carbon number of 6 to 30), 3 Å) having a substituent -16-200920180 80 (preferably an alkenyl group having a carbon number of 16 to 80 (preferably carbon 30), an alkylamino group having a carbon number of 1 to 60) which may have a substituent, may have a substituent An arylamine group having 6 to 60% of carbon atoms, an aralkylamino group having 7 to 8 Å (preferably having a carbon number of 7 to 00) which may have a substituent, and a carbon number which may have a substituent of 3 to 3 1 〇 (preferably having a carbon number of 3 to 9) alkylcarbenyl group, an arylmethyl fluorenyl group having 6 to 30 carbon atoms which may have a substituent (preferably having a carbon number of 8) 20) or a cyano group. R1 to R7 may each be plural, and adjacent ones may form a saturated or unsaturated cyclic structure. Examples of the halogen atom of R1 to R7 include fluorine, chlorine, bromine, and iodine. The alkyl group having 1 to 4 carbon atoms which may have a substituent of R1 to R7 may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an S-butyl group or an isobutyl group. T-butyl, η-pentyl, η-hexyl, η·heptyl, η-octyl, n-fluorenyl, n-fluorenyl, —alkyl, η-dodecyl, η-tride Alkyl, η-tetradecyl, η-pentadecyl, η-hexadecyl, η-heptadecyl, η_ + octadecyl, neopentyl, 1-methylpentyl, 2- Methylpentyl, pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxy Isobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl ' 2,3-dihydroxybutyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloro Ethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2 , 3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3_dibromo-bubutyl, 1,2,3-tribromopropyl, iodomethyl, iodoethyl, 2 - Ethyl, 2_ -17- 200920180 Iodine isobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-t-butyl, 1,2,3 - Di-propyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-aminoethyl, 1,3 -amino-iso Propyl, 2,3-diamino-t-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-arylethyl, 2-nonylethyl, 2-chloro Isobutyl, 1,2-oxoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl, 1,2,3-tricyanopropyl , nitromethyl, 1-nitroethyl, 2-nitroethyl, 1,2-dinitroethyl, 2,3-dinitro-t-butyl, 1,2,3-trinitropropyl, ring A pentyl group, a cyclohexyl group, a cyclooctyl group, a 3,5-tetramethylcyclohexyl group or the like. Preferred among them are methyl, ethyl, propyl, isopropyl, η-butyl, s-butyl, isobutyl, t-butyl, η-pentyl' η-hexyl, η-heptyl , η-octyl, η-fluorenyl, η-fluorenyl, η-undecyl, η-dodecyl, η-trityl, η -14; (: complete, η - 十Five-story base, η-sixteen yard base, η-seventeen yard base, η-eighteen yard base, neopentyl, 1-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1- Heptyloctyl, cyclohexyl, cyclooctyl, 3,5-tetramethylcyclohexyl, etc. Examples of the heterocyclic group having 3 to 30 carbon atoms which may have a substituent of R1 to R7 include, for example, 1-pyrrole. , 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, b-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-pyridazinyl, 2-pyridazinyl, 3- Pyridazinyl, 5-oxazinyl, 6-pyridazinyl, 7-pyridazinyl, 8-pyridazinyl, 2-imidazolidinyl, 3-imidazolidinyl, 5-imidazolidinyl, 6-imidazolium , 7-imidazolidinyl, 8-imidazolidinyl, 3-pyridyl, 4-pyridyl, 1-indenyl, 2-indenyl, 3-indenyl, 4-indenyl, 5-吲,6-fluorenyl, 7-fluorenyl, 1 -isoindenyl, -18- 200920180 2-isoindenyl, 3-isoindenyl, 4-isodecyl, 5-isoindole Sulfhydryl, 6-isodecyl, 7-isodecyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5- Benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuran , 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7- Quinolinyl, 8-quinolyl, 1-isoquinolinyl, 3-isoquinolyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinoline , 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-isoxazolyl, 2-isoxazolyl, 3-oxazolyl, 4- Carbazolyl, 9-carbazolyl, β-morpholin-1-yl, β-isomorpholin-3-yl, β-carboline-4-yl, β-isomorpholin-5-yl, β-porphyrin -6-yl, β-morpholin-7-yl, β-isomorpholine-6-yl, β-carboline-9-yl, 1-phenanthryl, 2-phenanthridine , 3-phenanthryl, 4-phenanthroline D, 6-phenanthrene D-based, 7-phenanthrene- D-decyl, 8-phenanthrene-2-yl, 9-phenanthrene-H, 10-phenanthryl, 1 -acridinyl, 2 - aridinyl, 3-arridinyl, 4-acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, U7-phenanthrene Cyclolin-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline -9-yl, 1,7-phenanthroline-10-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4 -yl, 1,8-phenanthroline-5-yl, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl 1,8-phenanthroline-1 0-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1, 9-phenanthroline-1 0-yl, 1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline--19- 200920180 4-based 1,10-phenanthroline-5-yl, 2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-enyl, 2,9-phenanthroline-4-yl, 2 , 9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl, 2,9-phenanthrene -7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl, 2,8-phenanthroline-3 -yl, 2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl , 2,8-phenanthroline-9-yl, 2,8-phenanthroline-1 0-yl, 2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2, 7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazine, 2-phenothiazine, 3- Phenothiazine, 4-phenothiazine, 10-phenothiazine, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenyloxazinyl, 4-phenoxazinyl, 1 0 - Phenooxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furenyl, 2-thiol, 3 -Thienyl, 2-methylpyrrole-1 -yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methyl-D-slight-5-yl, 3-methyl Kebbi-1-yl, 3-methylindole- 2-yl, 3-methylazolo-4-yl, 3-methyl-D]t--5-yl, 2-t-butyl Kirillo _ 4 - base 3-(2-phenylpropyl)indole-1-yl, 2-methyl-1-D-d-d, 4-methyl-1-D fluorenyl, 2-methyl- 3- D fluorenyl, 4-methyl-3-D fluorenyl, 2-t-butyl fluorene, 4-t-butyl-1-pyrene, 2-t-butyl- 3 - D 卩 卩, 4-t_butyl-3-fluorenyl and the like. Preferred among them are 2-pyridyl, 1-pyridazinyl, 2-pyridazinyl, 3-pyridazinyl, 5-pyridazinyl, 6-pyridazinyl, 7-pyridazinyl, 8- Pyridazinyl, 2-imidazolidinyl, 3-imidazolidinyl, 5-imidazolidinyl, 6-imidazolidinyl, 7-imidazolidinyl, 8-imidazolidinyl, 3-pyridyl, 4-pyridine-20 - 200920180 base, 1 - D lead D base, 2 - D extract base, 3 - D primer base, 4 - lead fluorenyl group, 5 - Π 哄 base, 6 - fluorenyl, 7 - 吲哚Base, 1-isoindolyl, 2-isoindolyl, 3-isodecyl, 4-isoindenyl, 5-isodecyl, 6-isoindenyl, 7-isodecyl 1, 1-oxazolyl, 2-isoxazolyl, 3-oxazolyl, 4-n-zolylzolyl, 9-n-zolylyl and the like. The alkoxy group having 1 to 40 carbon atoms which may have a substituent in R1 to R7 is a group represented by -?, and specific examples of the anthracene are the same as those described above, and preferred examples are also the same. Examples of the aryl group having 6 to 40 carbon atoms which may have a substituent of R1 to R7 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, and a 9-fluorenyl group. , 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-butyl, 2-butyl, 9-butyl, 1-indenyl, 2 - indenyl, 4-indenyl, 2-indenyl, 3-indolent, 4-indenyl, ρ-biphenyl-4-yl, ρ-bitriphenyl-3-yl, ρ -bitriphenyl-2-yl, m-bitriphenyl-4-yl, m-biphenyl-3-yl, m-bitriphenyl-2-yl, fluorenyl-tolyl, m- Tolyl, ρ-methylbenyl, pt-butylcarbyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4- Methyl-1-fluorenyl, 4'-methylbiphenyl, 4"-t-butyl-ρ-bi-diyl-4-yl, anthracene-halogen, m-carbocarbyl, P- A cumyl group, a 2,3-dimethylphenyl group, a 3,4-dimethylphenyl group, a 2,5-dimethylphenyl group, a mesityl group, etc., preferably a phenyl group, a 1-naphthyl group, or 2 -naphthyl, 9-phenanthryl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, p-tolyl, 3,4-xylyl, etc. R1 to R7 may have a substituent The aryloxy group having 6 to 40 carbon atoms is a group represented by -21 to 200920180 OAr, and specific examples of Ar may be the same as those described for the above aryl group, and preferred examples are also the same. The aralkyl group having 7 to 40 carbon atoms which may have a substituent, and examples thereof include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, and a 2-benzene group. Isopropyl, phenyl-t-butyl, ex-naphthylmethyl, Ια-naphthylethyl, 2-ct-naphthylethyl, l-α-naphthylisopropyl, 2-01- Naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl ,pyrrolemethyl, 2-(1_pyrrole)ethyl, Ρ-methylbenzyl, m-methylbenzyl, 〇-methylbenzyl, ρ-chlorobenzyl, m-chloride Benzyl, 〇-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, 〇-bromobenzyl, P-iodobenzyl, m-iodobenzyl, oxime-iodobenzene Methyl, P-hydroxybenzyl, m-hydroxybenzyl, fluorenyl-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, fluorenyl-aminobenzyl, ρ- Nifexyl, m-nitrobenzyl, guanidine-nitrobenzene Base, ρ-cyanobenzyl, m-cyanobenzyl, 〇-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, 1-chloro-2-phenylisopropyl, etc. Preferred among them are benzyl, P-cyanobenzyl, m-cyanobenzyl, decyl-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl and the like. Examples of the alkenyl group having 2 to 40 carbon atoms which may have a substituent of R1 to R7 include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, and 1,3. -butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-di Methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl-22 - 200920180, 3-phenylallyl, 3,3-diphenylene A propyl group, a fluorene group, a 2-dimethyl propyl group, a fluorenyl phenyl-1-butenyl group, a 3-phenyl-1-butenyl group, etc., preferably a styryl group, 2,2- Diphenylvinyl, 1,2-diphenylvinyl, and the like. An alkylamino group having 1 to 80 carbon atoms which may have a substituent as R1 to R7, an arylamine group having 6 to 80 carbon atoms which may have a substituent, and an aralkyl group having 7 to 80 carbon atoms which may have a substituent The amino group is represented by -Ni^Q2'. Specific examples of Q1 and Q2 are the same as those described for the alkyl group, the aryl group and the aralkyl group described above, and preferred examples are also the same. Examples of the alkylmercaptoalkyl group having 3 to 10 carbon atoms which may have a substituent of R1 to R7 include a trimethylcarbinyl group, a triethylmethane alkyl group, and a t-butyldimethylformyl group. Vinyl dimethyl methacrylate, propyl dimethyl methacrylate, and the like. Examples of the aryl methadone group having 6 to 30 carbon atoms which may have a substituent of R1 to R7 include triphenyl methacrylate, phenyl dimethylaxyl, t-butyl diphenyl. Carbenyl and the like. In addition, as the ring structure formed when R1 to R7 are plural, a non-saturated 6-membered ring such as a benzene ring may be used, and a saturated or unsaturated 5-membered ring or a 7-membered ring structure may be mentioned. In the formulae (101) to (104), X represents a group represented by any one of the following general formulas (111) to (116). -23- 200920180 R8

Dll)

(113)

(115)

(112) (114) (116) In the formulae (1) 1) to (116), R8 to R17 each independently represent a hydrogen atom, a halogen atom, and may have a carbon number of 1 to 40 of a substituent (preferably a substituent having a carbon number of 1 to 30), a heterocyclic group having a carbon number of 3 to 3 Å (preferably having a carbon number of 3 to 20), and a carbon number of 1 to 40 which may have a substituent (preferably An alkoxy group having 1 to 30 carbon atoms, an aryl group having 6 to 40 carbon atoms (preferably having a carbon number of 6 to 30) which may have a substituent, and a carbon number of 6 to 40 which may have a substituent (preferably carbon) An aryloxy group having 6 to 30), an aralkyl group having 7 to 40 carbon atoms (preferably having 7 to 30 carbon atoms) which may have a substituent, and a carbon number of 2 to 40 which may have a substituent (preferably The alkyl group having a carbon number of 2 -24 to 200920180 to 30), an alkyl group having 1 to 8 carbon atoms (preferably having a carbon number of 1 to 60) which may have a substituent, and a carbon number 6 which may have a substituent An arylamino group having 80 (preferably having a carbon number of 6 to 60), an aralkylamino group having a carbon number of 7 to 80 (preferably having a carbon number of 7 to 60), and a carbon which may have a substituent a number of 3 to 1 〇 (preferably a carbon number of 3 to 9) of a syllabary base of a sylvestre based on a carbon number of 6 to 30 (a carbon number of 3 to 9) Best 8~20 carbon atoms) or cyano. R8 to R17 may each be plural, and adjacent ones may form a saturated or unsaturated cyclic structure. Specific examples of the respective groups represented by R8 to R17 are the same as those described for the above-mentioned r1 to R7, and preferred examples are also the same. In the formulae (111) to (114), Y1 to Y3 each independently represent -CR (R is a hydrogen atom, the group of the X bond in the above general formulas (101) to (104) or the aforementioned R8, R9, R1G, R12, When any of R13 and R14 or a nitrogen atom is a nitrogen atom, the number is at least two on the same ring. Cz is the same as below. In the general formula (116), t is an integer of 〇~1. As the group represented by the general formula (11 1 1), any of the following structures is preferred. -25- 200920180

As the group represented by the general formula (1 1 2), any of the following structures is preferred. -26- 200920180

-27- 200920180 As a group represented by the general formula (1 1 3 ), any of the following structures is preferred.

As the group represented by the general formula (1 14), any of the following structures is preferred.

As the group represented by the general formula (Η 5), any of the following structures is preferred. -28- 200920180

base. R18

(121)

• · · · (122) R22 Υ1々/γ2

R25 * · (123) • · (125)

-29- • · . . . (124) 200920180 In the equations (a) 21) to (125), R18 to R25 and R8 to r1 Y1 to Y3 are the same as γ1 to Y3 of the equations (111) to (114). Specific examples of the groups represented by rU to R25 are the same as those described for R7, and the preferred examples are also the same. In the formulas (101) to (105), 'Cz is the following general formula (13). It is the same group. I R 1 to [1] or (132) r24 p 25 • ( .

An integer of z to 3), _SiR28R29·, _nr3〇_ 'R2 7, R28 and R29 may be combined with each other to form a saturation or structure. R24 to R3Q each independently represent a hydrogen atom, an alkyl group having 1 to 40 carbon atoms of a halogen atomic group, a ring group which may have a substituent, and a carbon number of 6 to 4 of an alkoxy group having 1 to 40 carbon atoms which may have a substituent. The aryl group of the fluorene, the group oxy group which may have a substituent, the aryl group having a carbon number of 7 to 4 Å having a substituent, and the carbon number of 2 to 40, may have a substituent alkyl group. 27)n-(n is 1 S-, a ring having a carbon number of 6 to 8 Å having a substituent, and a ring having a substitution of 3 to 30 may have a aryl group having a substitution of 6 to 40, which may have Amino groups of 1 to 80, can have -30-200920180

2 5 R each having 6 to 30 carbon atoms which may have a substituent may be a plurality of alkylcarboxyalkyl groups, arylcarbenyl groups or cyano groups having a carbon number of 7 to 80 and 3 to 10 which are substituted with each other. . R24~ can form a saturated or unsaturated cyclic structure. In the formula (132), Z represents an alkyl group having a carbon number which may be substituted, an aryl group having 6 to 18 carbon atoms which may be substituted, or an aromatic group having 7 to 4 carbon atoms which may have a substituent. Examples of the alkyl group having a carbon number of 1 to 20, such as methyl group, ethyl group, propyl group, isopropyl group, η-butyl group, s-butyl group, isobutyl group, t-butyl group, and η-pentyl group. , η-hexyl, n-heptyl, n-octyl, n-fluorenyl, n-fluorenyl, n-undecyl, η-dodecyl, n-tridecyl, n_four Alkyl, n_fifteen; k-kid' η-hexadecayl 'n _ seventeen yards base 'n _ eighteen yards, neopentyl, 1-methylpentyl, 2-methylpentyl,丨_Pentylhexyl, 丨-butylpentyl, 1-heptyloctyl, 3-methylpentyl, etc., preferably methyl, ethyl, decyl, η-hexyl, η-heptyl and the like. Examples of the aryl group of fluorene include a phenyl group, a naphthyl group, a tolyl group, a biphenyl group, and a terphenyl group. Preferred examples thereof include a phenyl group, a biphenyl group, and a tolyl group. Examples of the aralkyl group of fluorene include α-naphthylmethyl group, 丨_α-naphthylethyl group, 2-α-naphthylethyl group, fluorenyl-naphthylnaphthylisopropyl group, and quinone naphthyl group. Sulfhydryl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, benzo ''p-cyanobenzyl, m-cyanobenzyl, fluorenyl-cyanobenzyl, phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenyl The isopropyl group or the like is preferably benzyl, P-31 - 200920180, cyanobenzyl or the like. As the aforementioned c Z, the following structure

Further, it is particularly preferable that Cz is an oxazolyl group which may have a substituent or an arylcarbazolyl group which may have a substituent. Examples of the substituent 'for each group exemplified in the above general formulas (101) to (1〇5) include a halogen atom, a trans-amino group, a nitro group, a cyano group, a decyl group, an alkenyl group, and a ring. Ordinary EL of the general formula (101) to (105) of the present invention, such as a group, an alkoxy group, an aromatic radial group, an aromatic heterocyclic group, an aralkyl group, an aryloxy group or an alkoxycarbonyl group; Specific examples of the material for the element are, for example, the compounds exemplified below.

The compound shown by the organic EL is shown, but is not limited to -33- 200920180

ΰ ΰ ΰ -34- 200920180

-35- 200920180

-36- 200920180

-37- 200920180

-38- 200920180

No No -39- 200920180

-40- 200920180

A

N

-41 - 200920180

42- 200920180

-43- 200920180

Next, the main materials of the first luminescent layer and the second luminescent layer will be described. The main materials of the first luminescent layer and the second luminescent layer may be the same or different. Moreover, the energy diffusion of the triplet agonist energy generated by the fluorescent light-emitting layer is easily accepted, and the triplet energy gap of the main material of the first light-emitting layer and the second light-emitting layer is smaller than the main material of the fluorescent light-emitting layer. It is better. The triplet energy generated by the lower fluorescent main material is easily diffused into the first and second neoluminescent layers. Further, the triplet agonist energy to make the fluorescent light-emitting layer a main material can be easily diffused in the first light-emitting layer and the second light-emitting layer, and the triplet energy gap of the main material of the egg light-emitting layer is the first And the difference in the triplet energy gap of the main material of the second luminescent layer is preferably 0.1 volt or more. With this configuration, the triplet energy diffusion is more likely to occur, and the energy efficiency can be improved by -44-200920180. Further, a main material different from the first luminescent layer and the second luminescent layer can be used. In this case, the triplet energy gap of the second luminescent layer is made larger than the triplet gap of the main material of the first luminescent layer. In the hour, it is easy to diffuse the triplet energy from the first to fourth light-emitting layers to the second light-emitting layer. The main material of the first luminescent layer and the main material of the second luminescent layer are exemplified by the following (for example, a carbazole derivative). The triplet energy gap of such a compound is in the above range and can be applied as a main material of a green to red calendering blend. -45- 200920180

-46 - 200920180

-47- 200920180

-48- 200920180

-49 - 200920180

-50 200920180

-51 - 200920180

-52- 200920180

Further, the compound having a polycyclic condensed aromatic skeleton as follows may be used as a main material of the first luminescent layer or the second luminescent layer. That is, the polycyclic condensed aromatic skeleton having a substitution or an unsubstituted, and the lowest triplet energy gap of 2·0 e V or more and 3.0 e V or less. Among them, the polycyclic condensed aromatic skeleton has a nuclear atom number of 14 to 3 Å. It is preferred to be included in the chemical structural formula. Examples of the substituent of the polycyclic condensed aromatic skeleton moiety include a halogen atom, a trans group, a substituted or unsubstituted amine group, a nitro group, a cyano group, a substituent group of == generation, substitution or no extraction. a substituted, unsubstituted or unsubstituted family of: a substituted or unsubstituted aromatic disubstituted or unsubstituted aromatic heterocyclic group, a aryl group, a substituted or unsubstituted aryloxy group, Substituted: substituted or unsubstituted or unsubstituted alkoxy-53-200920180-based carbonyl or carboxyl group. When the polycyclic condensed aromatic skeleton has a complex substituent, two of them can form a ring. The atom may be a fluorine, a chlorine, a substituted or unsubstituted amino group represented by -XI X2, and as a child of XI and X2, each independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, or a η-butyl group. S-butyl, isobutyl, butyl, η-pentyl, η-hexyl, η-heptyl, η & „-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2 -hydroxyl.~1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-1 γ'-based, 1,2,3-trihydroxypropyl, Methyl, 1-chloroethyl, 2-$, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, mono-t-butyl, 1,2, 3. Trichloropropyl, bromomethyl, 1-bromoethyl, 2 _ _ 乙 乙 乙, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl , 2 ' 'dibromo-t-butyl, 1,2,3-tribromopropyl, iodomethyl, iodoethyl, '2' thief ethyl, 2-iodoisobutyl, 1,2-di Iodoethyl, 1,3-diiodide, 〇<3-diiodo-bubutyl, 1,2,3-triiodopropyl, aminomethyl, 1-anthraquinone, 2- Aminoethyl, 2-aminoisobutyl, I,2-diaminoethyl, 1 q diaminoisopropyl, 2,3-diamino-t-butyl, 1,2,3 -Triamine@基,备及amp; gas methyl, cyanoethyl, 2-cyanoethyl, 2-cyanobutyl, " dicyanethyl, 1,3-dicyanide Isopropyl, 2,3-dicyano-t-butyl, 1 Λ, 2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2婿骞butyl, dinitroethyl, 1,3-dinitroisopropyl, 2,3-di 5H -1 - ~r onion, 2 sinyl 1-butyl, 2-butyl, 9-Ding, 4-styryl, 1, 2, 3 - 3 Propyl, phenyl, 1-naphthyl, 2-naphthyl, phenyl, cleavage, 9-onionyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthrene-9--54- 200920180 Phenylphenyl, 1-indenyl, 2-indenyl, 4-indenyl, 2-biphenylyl, 3-yl, 4-biphenylyl, p-bitriphenyl-4-yl, p-linked Triphenyl-3-yl, triphenyl-2-yl, m-biphenyl-4-yl, m-biphenyl-3-yl, triphenyl-2-yl, fluorenyl-tolyl , m-tolyl, p-tolyl, pt phenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl, 4-methyl-1 - mercapto, 4'-methylbiphenyl, 4"-t-butyl-P-biphenyl-4-yl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, pyridine , 4-pyridyl, 2-indenyl, 3-indenyl, 4-indenyl, fluorenyl, 6-D fluorenyl, 7-fluorenyl D-based, 1-iso-D-indenyl , 3-iso D, D, 4-isoindolyl, 5-isodecyl, 6-isodecyl, 7-isodecylfuranyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, hexylfuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzoyl, 1-isobenzofuranyl, 3-isobenzene Furanyl, 4-isobenzoyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzoyl, 2-quinolyl, 3-quinolyl, 4-quinolyl , 5-quinolyl, 6-, 7-quinolyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinylisoquinolyl, 5-isoquinolinyl, 6-iso Quinolinyl, 7-isoquinolyl, quinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-yl, 2-phenanthryl, 3-phenanthryl 4-phenantidinyl, 6-phenanthryl, 7.-yl, 8-phenanthryl, 9-phenanthryl, 10-phenanthryl, 1-anthyridyl, 2-yl, 3-anthranyl , 4-arridinyl, 9-acridinyl, 1, 7-phenanthroline-2 1.7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1,7-phenanthrene Porphyrin-5-1.7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline-9·1.7-phenanthroline-10-yl, 1,8- Phenanthroline-2-yl, 1,8-phenanthroline-3·-biphenyl P-linked m-bi-butyl-1-naphthalene: diphenyl 3-pyridin-5, ; - benzofuranfuranfuran-quinoline, 4-8-iso-non-steep-phenanthroline- acridine-yl, yl,-yl,-yl, -55- 200920180 1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl, 1,8-phenanthrene -6-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl, 1,8-phenanthroline-1 0-yl, 1.9-phenanthroline-2 -yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1.9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl, 1 , 9-phenanthroline-7-yl, 1, 9-phenanthroline-8-yl, 1,9-phenanthroline-1 0-yl, 1,1 0-phenanthroline-2-yl, 1 , 1〇-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl, 2,9-phenanthroline-1-yl, 2, 9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl, 2,9- Phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl, 2,8-phenanthrene Benz-3-yl, 2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl, 2,8-non-cyclolin-6-yl, 2,8-non-twisted- 7-based, 2,8-non-cyclolin-9 ·yl, 2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl, 2,7-phenanthroline-3- , 2J-phenanthroline-4-yl, 2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2, 7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazine, 2-phenothiazine , 3-phenothiazinyl, 4-phenothiazinyl, 1-phenoxazinyl, 2-phenyloxazinyl, 3-phenyloxazinyl, 4-phenyloxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furenyl, 2-thiol, 3-thiol, 2-methylpyrrole- ; 1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrol-1-yl, 3-methyl Pyrrol-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2 -1 -butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrole- 1-yl, 2-methyl-1 -fluorenyl, 4-methyl-1-indenyl, 2-methyl-3-indenyl, 4-methyl-3-indenyl, 2- 1-butyl-1-indenyl, 4 -1 -butyl-1-indenyl, 2 -1 -butyl-3-indenyl, -56- 200920180 4-t-butyl-3-吲哚基等. Examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an η-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, and an η-pentyl group. , η-hexyl, η-heptyl, η-octyl, benzylmethyl, 1-ethylideneethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1 , 3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2- Chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloropropyl, bromomethyl , 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodide Isopropyl, 2,3-diiodo-t-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-amino Isobutyl, 1,2-amino-ethyl, 1,3 -amino-isopropyl, 2,3-amino-t-butyl, 1,2,3-diaminopropyl , aminomethyl, 1-isoethylethyl , 2-aminoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl, 1 , 2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroiso Propyl, 2,3-dinitro-t-butyl, 1,2,3-trinitropropyl and the like. Examples of the substituted or unsubstituted alkenyl group include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, and 1- Methylvinyl, styryl, 4-diphenylaminostyryl, 4_di-p-methylbenylamine, substantially ethylene, 4 - _-m-methylbenylaminophenylidene , 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, -57- 200920180 1,1-dimethyl dilute, 2-methylallyl Base, 丨-phenylallyl, 2-phenylene propyl ' 3 · phenylallyl, 3,3-diphenylallyl, 1,2-dimethyl propyl propyl, hydrazine Phenyl-1-butenyl, 3-phenyl-1-butenyl and the like. Examples of the it or unsubstituted cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group and the like. The substituted or unsubstituted alkoxy group is a group represented by -OY, and examples of Y include a methyl group, an ethyl group, a propyl group, an isopropyl group, an η-butyl group, an s-butylene group, and a butyl group. Η-pentyl, η-hexyl, η-heptyl, η-octyl, benzylmethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-aminoethyl , 1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2_chloroisobutyl, U2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-bubutyl, hydrazine, 2,3'trichloropropyl, bromomethyl, 1- Bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1, 2,3-tribromopropyl, iodomethyl, iodoethyl, 2-iodoethyl, 2-nonylisobutyl, hydrazine, 2-diiodoethyl, hydrazine, 3-diiodoisopropyl, 2,3-dip-t-butyl, 1,2,3-triiodopropyl, aminomethyl, ethylamino, 2-aminoethyl, 2-aminoisobutyl, hydrazine, 2-diaminoethyl, U-diaminoisopropyl, 2,3-diamino _t-butyl, hydrazine, 2,3-triaminopropyl Cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, u-dicyanoethyl, anthracene, 3-dicyanoisopropyl, 2,3_ Dicyano-t-butyl, 1,2,3-tricyanopropyl, nitromethyl, hydrazine-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitrate Ethyl, 1,3-dinitroisopropyl, 2,3-dinitro-t-butyl, hydrazine, 2,3-trinitropropyl, and the like. -58- 200920180 Examples of the substituted or unsubstituted aromatic hydrocarbon group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 9-fluorenyl group, and a 1-phenanthrene group. Base, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-butanyl, 2-butyl, 9-butyl, 1-indenyl, 2-indenyl, 4-indenyl, 2-biphenylyl, 3-butybenyl, 4-butybenyl, p-biphenyl-4-yl, p-bi-di--3-yl, p-bitriphenyl Benzyl-2-yl, m-bitriphenyl-4-yl, m-bitriphenyl-3-yl, m-biphenyl-2-yl, anthracene-tolyl, m-tolyl, p -tolyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1 - mercapto, 4'-methylbiphenyl, 4"-t-butyl-P-biphenyl-4-yl, etc. Examples of the substituted or unsubstituted aromatic heterocyclic group include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1-indenyl, 2-indenyl, 3-indole Base, 4-portion thiol group, 5-D fluorenyl group, 6-fluorene fluorenyl group, 7-P fluorenyl group, 1-iso 11 fluorenyl group, 2-iso Indenyl, 3-isoindenyl, 4-isoindenyl, 5-isodecyl, 6-isoindenyl, 7-isoindenyl, 2-furyl, 3-indolyl, 2 -benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3 -isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolyl , 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinoline , 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl '6-quinoxalinyl , 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthrene-59- 200920180 pyridine, 6-phenanthryl, 7-phenanthryl, 8-phenanthryl, 9-phenanthrene Pyridyl, 10-phenanthryl, 1-anridinoyl, 2-anridinoyl, 3-anridinoyl, 4-acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl 1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6- 1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl, 1,7-phenanthroline-1 0-yl, 1,8-phenanthroline-2-yl, 1,8-non-cyclo-lin-3-yl, 1,8-non-anthrace-4-yl, 1,8-non-anneal- 5·yl, 1,8-non-fluorinated-6-yl, 1, 8-non-cyclolin-7-yl, 1,8-non-circular- 9-yl, 1,8-non-cyclolin-10-yl, 1,9-non-alternative-2-yl, 1,9- Non-cyclolin- 3·yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl, 1,9-phenanthrene Porphyrin-7-yl, 1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl, 1,10-unaryolin-2-yl, 1,10-non-twisted- 3-Based, 1,10-Non-twisted _ 4-yl, 1,10-phenanthroline-5-yl, 2,9-phenanthroline-1·yl, 2,9-phenanthroline-3 -yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl , 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl, 2 ,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl' 2,8 - phenanthrene-9-yl, 2,8-non-cyclolin-10-yl, 2,7-non-union-l-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthrene Rotunolin-4-yl '2,7-phenanthroline-5- , 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1 - phenazinyl, 2-phenazine, 1-phenothiazine, 2-phenothiazine, 3-phenothiazine, 4-phenothiazine, 10-phenothiazine, 1- pheno Zinyl, 2-phenyloxazinyl, 3-phenyloxazinyl, 4-phenyloxazinyl, 10-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl '5-oxadiazolyl, 3-furenyl, 2-thiol, 3-thiol, -60- 200920180 2-methylpyrrol-1-yl, 2-methyl Pyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrole-2-yl, 3- Methyl hydrazine is a slightly 4-benzyl group, 3-methyl leuco-5-yl, 2 -1 - butyl succinyl-4 yl, 3-(2-phenylpropyl)pyrrole-1 -yl, 2-methyl-1-indenyl, 4-methyl-1-D fluorenyl, 2-methyl-3-D-U-based, 4-methyl-3-D-indenyl, 2- T-butyl-1 -fluorenyl, 4 -1 -butyl-1-indenyl, 2 -1 -butyl-3-indenyl, 4-t-butyl-3-indenyl, etc. . Examples of the substituted or unsubstituted aralkyl group include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, and a benzene group. Base-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-ot-naphthylisopropyl , β-naphthylmethyl, l-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, 1-pyridyl Methyl, 2-(1-pyrrole)ethyl, ρ-methylbenzyl, m-methylbenzyl, 〇-methylbenzyl, ρ-chlorobenzyl, m-chlorobenzyl Base, 〇-chlorobenzyl, P-bromobenzyl, m-bromobenzyl, 〇-bromobenzyl, ρ-iodobenzyl, m-iodobenzyl, oxime-iodobenzyl , ρ-p-benzylmethyl, m-hydroxybenzyl, fluorenyl-hydroxybenzyl, ρ-aminobenzyl, m-aminobenzyl, fluorenyl-aminobenzyl, ρ-nitro Benzyl, m-nitrobenzyl, 〇-nitrobenzyl, P-cyanobenzyl, m-cyanobenzyl, fluorenyl-cyanobenzyl, 1-hydroxy-2-phenyl Isopropyl, 1-chloro-2-phenylisopropyl and the like. The substituted or unsubstituted aryloxy group is represented by -〇Z, and examples of Z include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, and a 9-fluorenyl group. , 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-butyl, 2-butyl- 9-butyl, 1-mercapto, 2 -fluorenyl, 4-mercapto, -61 - 200920180 2 -biphenyl, 3-biphenyl, 4-biphenyl, p-bitriphenyl-4-yl, p-biphenyl-3 -yl, p-bi-diyl-2-yl, m-bi-diyl-4-yl, m-biphenyl-3-yl, m-biphenyl-2-yl, anthracene-toluene Base, m-tolyl, p-tolyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthalene , 4-methyl-1-indenyl, 4'-methylbiphenyl, 4"-t-butyl-P-biphenyl-4-yl, 2-pyrrolyl, 3-pyrrolyl, Pyrazinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-indenyl, 3-oxoindenyl, 4-13 indole, 5-D indole, 6- D leads D, 7 - D leads D, 1 -isoindenyl, 3 -isoindolyl, 4 -isoindolyl, 5-isoindolyl, 6-isoindolyl, 7 - Different , 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzene And furyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuran , 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl , 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-fluorenyl, 1-non-D-decyl, 2-undecyl, 3-undecyl, 4-non-D-decyl, 6-nonindolyl, 7-non D-based, 8-non-D-based, 9-undecyl, 10-phenanthryl, 1-anridinoyl, 2-anridinoyl, 3-anridinoyl, 4-anridinoyl, 9-acridine 1,1,phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl, 1, 7-phenanthroline-6-yl, 1, 7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl, 1, 7 -phenanthroline-1 0-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl, 1,8- Philippine 咐-5- -62 - 200920180, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl, 1, 8-phenanthroline-1 0-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9 -phenanthroline-5-yl, 1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1, 9-phenanthrene Rotunolin-1 0-yl, 1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1,10-non-wound Lin-5-yl, 2,9-non-inden-1-yl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline -5-yl, 2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10 -yl, 2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl , 2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl, 2 , 7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl, 2,7 -phenanthroline-6-yl, 2,7- Cyclopiperidin-8-yl, 2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazine, 2- phenothiazine, 3-phenylthiazinyl, 4-phenothiazine, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenyloxazinyl, 4-phenyloxazinyl, 2 -oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furenyl, 2-thiol, 3-thiol, 2 -methylpyrrole-1 -yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1 -yl, 3 -methylpyrrol-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-t-butylpyrrol-4-yl, 3-(2-phenylpropyl Pyrrol-1-yl, 2-methyl-1-indenyl, 4-methyl-1-indenyl, 2-methyl-3-indenyl, 4-methyl-3-indolyl , 2-t-butyl-1-indenyl, 4-t-butyl-1-indenyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indole哚基等. -63 - 200920180 The substituted or unsubstituted alkoxycarbonyl group is represented by -COOY, and examples of the oxime include methyl group, ethyl group, propyl group, isopropyl group, η-butyl group, S-butyl group, and different groups. Butyl, t-butyl, η-pentyl, η-hexyl, η-heptyl, η-octyl, benzylmethyl, L hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl,丨, 2-dihydroxyethyl, hydrazine, 3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, chloromethyl, ι-chloro Base, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-bubutyl, 1,2,3-tri Chloropropyl, bromomethyl ' 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, hydrazine, 2-dibromoethyl, hydrazine, 3 -dibromoisopropyl, 2,3_ Dimethyl butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl '2-isobutylene, hydrazine, 2-diiodoethyl, hydrazine, 3_diiodoisopropyl, 2,3_bis, _t-butyl, anthracene, 2,3-triiodopropyl, aminomethyl '1 ·aminoethyl, 2-aminoethyl, 2_Aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl, 2,3·diamino-t-butyl 1,2,3-Triaminopropyl, cyanomethyl, oxime-aminoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1 ,3-dicyanoisopropyl, 2,3-dicyano-bubutyl, 1,2,3-triaminopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitro Isobutyl, U2-mononitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-t-butyl, 1,2,3-trinitropropyl, and the like. The %' SU polycyclic condensed aromatic skeleton has a substituent, and the above substituent is preferably a substituted or unsubstituted aryl or heteroaryl group. It is preferred that the heteroaryl group as a substituent has a carbazole skeleton removed. ', ' Further, the polycyclic condensed aromatic skeleton is selected from substituted or unsubstituted -64 - 200920180 phenanthrenyl, substituted or unsubstituted sulfonyl, substituted or unsubstituted fluoranthene, substituted or A group of unsubstituted tribenzophenyldiyl-substituted or unsubstituted naphthalenediyl groups is preferred. Further, the polycyclic condensed aromatic skeleton portion is preferably replaced by a group having a phenanthrene, a crucible, a scalper, a triphenyl group or a naphthalene group. The polycyclic condensed aromatic skeleton portion is preferably one of the following formulas (1) to (4).

Ar1,,. (1) (2)

Ar3, ., (3) (4), Ar4,. A^-Np-Ar6 In the formula (1) to the formula (3), the condensed ring structure of Ar1 to Ar4 is 4 to 1 Å. The substituted or unsubstituted nucleus carbon-65-200920180 The compound represented by the formula (1) may, for example, be substituted or unsubstituted phenanthrene, or the like. Examples of the compound of the formula (2) include substituted or unsubstituted terpenes, anthracenes, fluoranthene and the like. The compound represented by the formula (3) is, for example, a substituted or unsubstituted benzofluoranthene or the like. In the formula (4), 'Np represents a substituted or unsubstituted naphthalene, and each of Ar5 and Ar6 independently represents a substituent composed of a substituted or unsubstituted aryl group having 5 to 14 carbon atoms in a single or plural combination. However, Ar5 and Ar6 do not contain antimony. In the present invention, the polycyclic condensed aromatic skeleton portion is preferably a phenanthrene derivative represented by the following formula (10).

The phenanthrene derivative may have a substituent, and examples of the substituent include hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy 'alkyl Sulfur, aryl ether, aryl sulfide, aryl, heterocyclic, halogen, halogenated alkane, halogenated alkene, halogenated alkyne, cyano, aldehyde, carbonyl, carboxyl, ester Amine, nitro, formalyl, decyloxy. As such a phenanthrene derivative, the following are mentioned, for example. -66 - 200920180

-67- 200920180

In the present invention, the polycyclic condensed aromatic skeleton portion is preferably a cave derivative represented by the following formula (11). -68 - 200920180

Examples of the cave derivative include the following.

-69- 200920180

-70- 200920180

In the present invention, the polycyclic condensed aromatic skeleton portion is preferably a derivative of a compound (benzo[c]phenanthrene) represented by the following formula (12). -71 - 200920180

In the present invention, the polycyclic condensed aromatic skeleton is preferably a derivative of a compound (benzo[c]) represented by the following formula (13).

U • · _ (13) Examples of the derivative of such a compound include the following. -72 - 200920180

In the present invention, the polycyclic condensed aromatic skeleton is preferably a derivative of a compound (dibenzo[c, g]phenanthrene) represented by the following formula (14).

As a derivative of such a compound, the following are mentioned, for example.

In the present invention, the polycyclic condensed aromatic skeleton portion is preferably a fluoranthene derivative represented by the following formula (15). -73- (15) 200920180 As a fluoranthene derivative, for example, the following

Examples of the substituted or unsubstituted benzofluoranthene include a benzo[b]fluoranthene derivative represented by the following formula -74-200920180 (152) and a formula [k]. 】 fluoranthene derivatives. X1

• (151) • (152) Carbocyclic aromatic monocyclic aromatics such as paper atoms, halogen or branched gas, such as fluorine atoms, chlorine compounds (151) and (152) X1 to X24 represent a sub, straight, branched or cyclic alkyl group, a linear chain, a divided group, or a substituted or unsubstituted aryl group. Further, the aryl group means, for example, a phenyl group or a naphthyl group, and represents, for example, a furyl group, a thiol group or a pyridyl group. X1 to X24 are preferably a hydrogen atom, a halogen atom (for example, -75 - 200920180 atom, a bromine atom), a linear, branched or cyclic alkyl group having a carbon number of 1 to 16 (for example, methyl group, ethyl group, η-). Propyl, isopropyl, η-butyl, isobutyl, sec-butyl, tert-butyl, η-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, η- Hexyl, 3,3-dimethylbutyl, cyclohexyl, η-heptyl, cyclohexylmethyl, η-octyl, tert-octyl, 2-ethylhexyl, η-fluorenyl, η-fluorenyl , η-dodecyl, η-tetradecyl, η-hexadecyl, etc.), a linear, branched or cyclic alkoxy group having a carbon number of 1 to 16 (for example, methoxy, B) Oxyl, η-propoxy, isopropoxy, η-butoxy, isobutoxy, sec-butoxy, η-pentyloxy, neopentyloxy, cyclopentyloxy, Η-hexyloxy, 3,3-dimethylbutyloxy, cyclohexyloxy, η-heptyloxy, η-semiyloxy, 2-ethylhexyloxy, η-hydrazine a group, an η-fluorenyloxy group, an η-dodecyloxy group, an η-tetradecyloxy group, an η-hexadecyloxy group, or the like, or a carbon number of 4 to 16 a substituted or unsubstituted aryl group (for example, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl, 4-η-butylphenyl, 4-tert-butylphenyl, 4-isopentylphenyl, 4-tert-pentylphenyl, 4-η-hexylphenyl , 4-cyclohexylphenyl, 4-η-octylphenyl, 4-η-decylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5- Dimethylphenyl, 3,4-dimethylphenyl, 5-indanyl, 1,2,3,4-tetrahydro-5-naphthyl, 1,2,3,4-tetrahydro-6 -naphthyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 4-η-propoxy Phenylphenyl, 4-isopropoxyphenyl, 4-η-butoxyphenyl, 4-η-pentyloxyphenyl, 4-η-hexyloxyphenyl, 4-cyclohexyloxy Phenyl, 4-η-heptyloxyphenyl, 4-η-octyloxyphenyl, 4-η-fluorenyloxyphenyl, 2,3- -76 - 200920180 dimethoxyphenyl , 2,5-dimethoxyphenyl, 3,4-dimethoxyphenyl, 2-methoxy-5-methylphenyl, 3-methyl-4-methoxyphenyl, 2 _fluorophenyl, 3-fluorobenzene , 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-trifluoromethylphenyl, 3,4-dichlorophenyl, 2 -methyl-4-chlorophenyl, 2-chloro-4-methylphenyl, 3-chloro-4-methylphenyl, 2-chloro-4-methoxybenyl, 4-predominyl, 3 -phenylphenyl, 4-(4'-methylphenyl)phenyl, 4-(4'-methoxyphenyl)phenyl, 1-naphthyl, 2-naphthyl, 4-ethoxy- 1-naphthyl, 6-methoxy-2-naphthyl, 7-ethoxy-2-naphthyl, 2-furyl, 2-thiol, 3-thiol, 2-pyridyl, 3 a pyridyl group, a 4-pyridyl group or the like, preferably a hydrogen atom, a fluorine atom, a chlorine atom, a group having a carbon number of 1 to 10, a oxy group having a carbon number of 1 to 10, or a aryl group having a carbon number of 6 to 12 The group is more preferably a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or a carbocyclic aromatic group having 6 to 10 carbon atoms. The benzo[b]fluoranthene derivative represented by the formula (1 5 1) may, for example, be as follows. -77- 200920180

The following. -78- 200920180

In the present invention, the polycyclic condensed aromatic skeleton portion is preferably a tribenzo benzene derivative represented by the following formula (16). One part of the carbon of the skeleton portion may be nitrogen.

(16) The triphenyl benzene derivative is exemplified by the following. -79- 200920180

-80- 200920180

-81 - 200920180 0~n h3c

H3c

200920180

Further, the polycyclic condensed aromatic skeleton may contain a nitrogen atom, and may be, for example, the following. -83- 200920180

Examples of the compound of the formula (4) include compounds represented by the following formulas (41) to (48).

Np-(Np)n-Np · (41) In the formula (41), Np represents a substituted or unsubstituted naphthalene, and n is an integer of 〇 to 3.

-84- • (42) 200920180 However, 'An, Ar2, and A represent a hydrogen atom or a substituent. a k is an integer from 1 to 4, in the formula (42), ΑΓι and the substituted phenanthrene. Ar3 representation

Al"2 indicates that at least one of the nuclear carbon numbers 6 f ~ which are independently substituted by ^ is naphthalene ' b, and c is each 1 to k is 2 or more, R, substituted naphthalene or ί 3 0 Aryl. . An integer from R1, R7, and R8. Can be the same or phase

(43) In the formula (43), ΑΓ3 represents a aryl group having a nucleus number of 6 to 3 Ri Rii to R·23 represents a hydrogen atom or a substituent. k is an integer from 1 to 4, and when k is 2 or more, & base, R1, R8, may be the same or phase

* * * (44) , R* , R8 , and (14), AI·3 represents aryl Rii to R19 and Rm to R·3 having a nuclear carbon number of 6 to 3 Å. Represents a hydrogen atom or a substituent. -85- 200920180 k is an integer from 1 to 4, and when k is 2 or more, R1 may be the same or phase S.

In the formula (45), Ar3 represents an aryl group having a core carbon number of 6 to 30, and R!, r8 and R36 represent a hydrogen atom or a substituent. k is an integer from 1 to 4, and when k is 2 or more, R may be the same or different.

* (4) In the formula (46), "Ar; an aryl group having a carbon number of 6 to 30, R, and 8, and r31 to r42 represent a hydrogen atom or a substituent. k is an integer from 1 to 4, and when k is 2 or more, Ri may be the same or different. -86- • · · (47) 200920180 • · · (47)

In the formula (47), Αγ3 represents a nucleus carbon number of 6 to 3 Rs, and Rs and RS1 to r65 represent a hydrogen atom or a substituent. k is an integer from 1 to 4, and when k is 2 or more,

In the formula (48), Ar3 represents an RSI to R58 having a core carbon number of 6 to 30, and R70 to R74 represents a hydrogen atom or a substitution of 9 k which is an integer of 1 to 4, and when k is 2 or more, the difference is. Specific examples of the compound include, for example, the aryl group of the following I, and R! to R1 may be the same or the bovine • (48) aryl group, R!, R8, and £. Can be the same or phase -87- 200920180

-88-200920180 Further, as the main material, for example, an oligophthalene derivative represented by the following formula (49) can be given.

(wherein π is 1 or 2, Ar1 is a substituent represented by the general formula (50) or the general formula (51), Ar2 is a substituent represented by the general formula (52) or the general formula (53), and Ar3 is a general formula. (54) or a substituent represented by the general formula (55), each of r1 to R3 independently represents a hydrogen atom, a linear or branched alkyl group having 6 or less carbon atoms, an alicyclic group, or an unsubstituted or substituted group. An aromatic ring having an unsubstituted -89-200920180 or a heteroaromatic ring of a substituent, an alkoxy group, an amine group, a cyano group, a decyl group, a vine group, a carbonyl group, or a halogen) and an 'oligonaphthalene derivative It may be a structure having the general formula (56).

• · · · (56) • · · (57) • · · (58) • · · (59) • · · (60) • · · (61), η is 1 or 2, Arl is general (57 Or the general formula (58) /, the substituent Ar is a substituent represented by the general formula (59), Ar3 is a general formula (), or the substituent represented by the general formula (61), and each of R1 to R3 is independently represented. a hydrogen atom, a linear or branched alkyl 'alicyclic or alkylene group having a 亘Si number of 6 or less, an aromatic ring having a substituent or a substituent, a heteroaromatic ring having an unsubstituted or substituted group -90-200920180, an alkoxy group Any one of an amine group, a cyano group, a methoxyalkyl group, an ester group, a carbonyl group, and a halogen) More specifically, the oligonaphthalene derivative has a structure represented by the general formula (62).

• · · · (62) • · · (63) • · · (64) . . . (65) • (66) (where η is 1 or 2, Ar1 is general (63) or general (64) A substituent represented by the general formula (65) or the general formula (66), and each of R1 and R3 independently represents a nitrogen atom, a linear or branched alkyl group having 6 or less carbon atoms, An alicyclic alkyl group, an aromatic ring having an unsubstituted or substituted group, a heteroaryl 91 ring having an unsubstituted or substituted group, an alkoxy group, an amine group, a cyanogen 200920180 group, a decyl group, an ester group, a carbonyl group, a halogen Further, the oligophthalene derivative may have a structure represented by the general formula (67).

• · · (67) • · · (68) • · · (69) • · · (70) • · · (71) (where n is 1 or 2, Arl is general (68) or general (69) The substituent shown, Ar3 is a substituent represented by the general formula (70) or the general formula (71), and each of R1 and R3 independently represents a hydrogen atom and has a linear or branched alkyl group having 6 or less carbon atoms. An alicyclic alkyl group, an aromatic ring having an unsubstituted or substituted group, a heteroaromatic ring having an unsubstituted or substituted group, an alkoxy group, an amine group, a cyano group, a decyl group, an ester group, a carbonyl group, or a halogen ~ test) Especially for those with the structure shown in general formula (72). -92- 20〇92〇18〇

• · · · (72) • · · (73) • · · (74) • · · (75) • · · (76) (where η , — 绮 1 or 2, Ar1 is general (73) or General formula (74) is not substituted, 3

Rl and 3 r are a substituent represented by the general formula (75) or the general formula (76), and a hydrogen atom, a linear or a few group having a carbonium 6 or less, an alicyclic alkyl group, or the like, Any of a hetero-aromatic ring having an unsubstituted ring, a fluorene-substituted substituent, a heterocyclic ring having an anthracene, a substituent or a substituent, an alkoxy group, a methane group, an ester group, a condensing group, or a halogen. It is preferred that the chlorine has a structure represented by the general formula (77). -93 - 200920180 \〇(Ar3 • · · (77) Ο • · · (78) ~O-R3 • · · (79) ο • · . (80) (81) (where η is 1 or 2, Ar1 is a general formula wherein the substituent Ar is a substituent represented by the general formula (80) or the general formula (81), and each of R1 and R3 independently represents a hydrogen atom and has a straight bond or a branch having a carbon number of 6 or less. An alkyl group, an alicyclic alkyl group, an unsubstituted ring, an anthracene having a te, a sulphur, a sulfonium group, an amine group, a cyanocyanyl group, an ester group, a carbonyl group, or a halogen) Specific examples of the alkyl group having 6 or less carbon atoms include a methyl group, a propyl group, an i-propyl group, an η_τ group, a butyl group, an ethyl group, an η-ylpentyl group, a 1-butyl group, a sec-butyl group, and the like. I-pentyl group, η-hexyl group, etc. A cycloalkyl group, a cyclopentyl group, and an alicyclic alkyl group may, for example, be a cyclopropylcyclohexyl group. Examples of the aryl group (tetra) having an unsubstituted or substituted group include a phenyl group. , naphthalene-94- 200920180, fluorenyl, fluorenyl, fluorenyl, etc. Examples of the heteroaromatic ring having an unsubstituted or substituted group include a pyridyl group, a fluorenyl group, a carbazolyl group, a thiol group, and a furyl group. Etc. Also, as shown in general formula (49) Specific examples of the naphthalene derivative, an oligonucleotide can include a naphthalene derivative represented by the following structural formula. However, the present invention is not limited thereto. -95-200920180

-96- 200920180

-97- 200920180

-98- 200920180

-99- 200920180

100- 200920180

f-Bu f-Bu i-Bu 200920180

Ch3 -102- 200920180

-103- 200920180

-104- 200920180

-105- 200920180

106- 200920180

-107- 200920180

Further, examples of the oligonaphthalene derivative include those represented by the following formula (43).

-108- 200920180 (wherein R1 to R6 are each independently a group, and are optionally selected from the group consisting of hydrogen, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted amino group, η The integer of 2 to 4) As the oligonaphthalene compound, for example, the following ones can be mentioned.

-109- 200920180 9

The main material "as the first luminescent layer or the second luminescent layer" is exemplified by the following compounds. R, a-Ar11-Ar12-Ar13-Rlb (21) represents the 2,7-13_] of the ring, ring, and benzene ring. In the above formula (21), Rla, Rlb, Ar11, Ari2, and Arl3 Self-substituted or unsubstituted benzene ring, or substituted or unsubstituted naphthalene ring, scald ring, tribenzophenone ring, phenanthrene ring, benzophenanthrene ring, dibenzophenanthrene benzophenone, benzo[ b) annihilation ring, benzo ring and fluorene aromatic hydrocarbon ring. When A r 12 is a substituted or unsubstituted ring or a substituted or unsubstituted phenanthrenyl or tribenzophenyl group, [R, Ar11-] and [Rlb-Ar phase have a structure having a different structure. -110 - ... (22) 200920180 In the above formula (22), the Han 2 1 is a substituted or unsubstituted naphthalene ring. R2b represents a self-substituted or unsubstituted phenanthrene ring, a tribenzophenone ring, a benzophenanthrene ring, a phenanthrene ring, a benzotribenzophenone ring, a fluoranthene ring, a benzo ring and a ring. Condensed aromatic cannes.

Ar2 2 represents a benzene ring selected from substituted or unsubstituted, naphthalene ring, cave ring, fluoranthene ring, tribenzophenone ring, triphenylene ring, dibenzophenanthrene ring, benzotribenzophenone ring, benzo An anthracene ring, a benzo[b]fluoranthene ring, and a condensed aromatic hydrocarbon group of a genomic ring. Further, the substituent of R2a and R2b is not an aryl group, and when Ar21 or Ar22 is a naphthalene ring, the substituents of Ar21 and Ar22 are not aromatic.

In the above formula (22_1), R 2a and R 2b represent a phenanthrene ring selected from substituted or unsubstituted, a tribenzophenone ring, a triphenylene ring, a dibenzophenanthrene ring, a benzobenzophenone ring, and a benzo[b] group. 】 Fluorinated ring, fluoranthene ring, benzo ring and ring-condensed aromatic hydrocarbon group. Further, the substituent of R2a, R2b, Ar2i or Ar22 is not an aryl group. 200920180 B31 / "31-Ar32

B32 B33

(23) In the formula (23), when Ar3i, Ar32, Ar33, B31, B32, B33, and B34 have one or a plurality of substituents, the substituent is an alkyl group having 1 to 20 carbon atoms and a carbon number of 1 to A halogenated alkyl group of 20, a cycloalkyl group having 5 to 18 carbon atoms, a carboxyalkyl group having 3 to 20 carbon atoms, a cyano group or a halogen atom is preferred. The substituent of Ar32 may further be an aryl group having 6 to 22 carbon atoms. Since the substitution gene does not have a nitrogen atom, the stability of the host material can be further improved, and the life of the element can be further extended. Further, the number of the complex aryl substituents of Ar32 is preferably 2 or less, and preferably 1 or less. Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an η-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, and an n-pentyl group. , η-hexyl, η-heptyl, η-octyl, η-fluorenyl, η-fluorenyl, η-undec' alkyl, η-dodecyl, η-tridecyl, η_ten Tetraalkyl, η-pentadecyl, η-hexadecyl, η-heptadecyl, η-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, butylpentyl, 1-heptyloctyl, 3-methylpentyl and the like. Examples of the halogenated alkyl group having 1 to 20 carbon atoms include a chloromethyl group, a 1-chloroethyl group, a 2-chloroethyl group, a 2-chloroisobutyl group, an ι,2-dichloroethyl group, and 1, 3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloropropyl, bromomethyl, -112-1 -mobromoiso-1-ioioiodoyl, Octylaryltrimethyloctyl, benzyl, ethylformamidine, and the like. Atomic phenyl group, benzo, base, 200920180 ethyl, 2-bromoethyl, 2-bromoisobutyl, anthracene, 2-dibromoethyl, propyl, 2,3-dibromo-t-butyl Base, hydrazine, 2,3·tribromopropyl, iodoethyl, 2-iodoethyl, 2-iodoisobutyl, hydrazine, 2-diiodoethyl, propyl, 2,3-diiodo-t - butyl, 1,2,3-triiodopropyl, and the like. Examples of the cycloalkyl group having 5 to 18 carbon atoms include, for example, a cyclopentylcyclooctyl group and a 3,5-tetramethylcyclohexyl group, and examples thereof include cyclohexene, 3,5-tetramethylcyclohexyl, and the like. . As a carbon number of 3 to 20, a methylidene group is, for example, an alkylmercaptoalkylene group or an aralkylcarboalkyl group as an example. A methoxyalkyl group, a triethylmethyl sulfonyl group, a tributyl carbene group.矽alkyl, triisobutylcarboxyalkyl, dimethylethyldimethylisofuranmethylmercaptoalkyl, dimethylpropyldimethylbutyrylalkyl, dimethyl-tert-butylformamidine isopropylformane The base, phenyldimethylformylalkyl group, diphenylalkyl group, diphenyl tert-butylformamyl group, and triphenylmethyl group as a halogen atom include a fluorine atom, a chlorine atom, and a bromine atom as a carbon number 6~ Examples of the aryl substituent of 22 include benzene, terphenyl, naphthyl, fluorenyl, fluoranthyl, 9,10-di 9,10-diarylindenyl, trimethyl, phenanthryl , benzofifidolyl, benzotrimethylene, benzofluorenyl, dibenzofuran is preferably a phenyl group having 6 to 18 carbon atoms, a biphenyl group, a bisphenylene group, a fluorenyl group, and 9 , 10-dimethylindenyl, trimethyl, 1,3-dimethyl, 1,3-di, cyclohexyl, cycloalkyl, exemplified by trimethyldecylcarbenyl, diyl Methyl sand alkyl, iodine, fluorenyl, dimethyl, naphthyl, -113- 200920180 benzophenanyl, a fluorenyl group, more preferably a carbon number of 6 to 14 Phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl. R4a-Ar41-R4b (24) In the above formula (24), when R4a, R4b, and Ar4i have a single or plural substituent, the substituent is a substituent having a carbon number of 1 to 2 0. A halogenated alkyl group having 1 to 2 carbon atoms, a cycloalkyl group having 5 to 18 carbon atoms, a methylidene group having 3 to 2 carbon atoms, a cyano group or a halogen atom is preferred. The substituent of Ar41 may further be a carbon number. The aryl group of 6 to 22. The substitution gene does not have a nitrogen atom, so that the stability of the main material can be further improved, and the life of the element can be further extended. Moreover, the number of the complex aryl substituents of Ar41 is preferably two. The following is preferably one or less. Examples of the hospital base having a carbon number of 1 to 20 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an η-butyl group, an s-butyl group, and an isobutyl group. T_butyl, pupentyl, η-hexyl, η-heptyl, η-octyl, n-fluorenyl, n_fluorenyl, n_---院, η - eleven, η - twelve House base, η_fourteen yard base, η_ fifteen yard base, η-hexadecyl, η·heptadecyl, η-octadecyl, neopentyl, 1-methylpentyl, 2 -methylpentyl, 1-pentylhexyl, b-butylpentyl, bheptyl-semiyl, 3-methylpentyl, etc. Examples of the halogenated alkyl group having 1 to 20 carbon atoms include a chloromethyl group, a 1-chloroethyl '2-chloroethyl group, a 2-chloroisobutyl group, a 1,2-dichloroethyl group, and 1 ,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloropropyl, bromomethyl, -114- 200920180 1-bromoethyl, 2-bromoethyl Base, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2,3-tribromopropyl , iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo- T-butyl, 1,2,3-triiodopropyl, etc. Examples of the cycloalkyl group having 5 to 18 carbon atoms include a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and a 3,5-tetramethyl group. Examples of the cyclohexyl group and the like include a cyclohexyl group, a cyclooctyl group, a 3,5-tetramethylcyclohexyl group, etc. As a carboxyalkyl group having a carbon number of 3 to 20, for example, an alkylcarbenyl group or an arylcarbenyl group. Or an aralkylmethyl sulfonyl group is preferable, and examples thereof include a trimethylmethane alkyl group, a triethyl methoxyalkyl group, a tributyl methoxyalkyl group, a trioctyl methoxyalkyl group, a triisobutyl methoxyalkyl group, and a dimethyl group. Base ethyl methacrylate, two Isofuranylmercaptoalkyl, dimethylpropylformamidin, dimethylbutylformamidinyl, dimethyl-tert-butylmethyldecyl, diethylisopropylformamidinyl, phenyldimethyl A mercaptoalkyl group, a diphenyl-tertylmethyl fluorenyl group, a diphenyl-tert-butyl carboxymethyl group, a triphenyl fluorene group, etc. The halogen atom is a fluorine atom, a chlorine atom, a bromine atom, and a picking atom. Examples of the aryl substituent having 6 to 22 carbon atoms include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluoranthenyl group, a 9,10-dialkylfluorenyl group, and 9, 10-Diarylsulfonyl, trimethylidene, phenanthryl, benzophenanthrenyl, dibenzophenanthrenyl, benzotrimethyl, benzophenanyl, dibenzopyranyl are preferred, preferably a phenyl group, a biphenyl group, a triphenylene group, a naphthyl group, a fluorenyl group, a fluorenyl group 9,10-dimethylindenyl group, a trimethyl group, a phenanthryl group, a -115 group having a carbon number of 6 to 18. - 200920180 Benzophenanthrenyl, dibenzofuranyl group, more preferably a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group or a dibenzofuranyl group having a carbon number of 6 to 14. Further, examples of the main material include the following phenanthrene derivatives or tribenzobenzene derivatives.

-116- 200920180

-117- 200920180

-118 200920180

-119- 200920180

Wherein, when the fluorescent light-emitting layer and the first and second fluorescent light-emitting layers are formed using the main material of the energy gap, the ionization potential (Ip) of the main material and the hole-120-200920180 injection into the transport layer and the like When it becomes larger, it is difficult to inject the hole in the fluorescent light-emitting layer, and it is feared that the driving voltage rise with sufficient brightness cannot be achieved. At this time, when the fluorescent light-emitting layer contains a hole injection and a transport charge injection aid, it is easy to inject the hole into the fluorescent light-emitting layer, and the driving voltage can be lowered. As the charge injection auxiliary agent, for example, general hole injection, transport material, or the like can be used. Specific examples include triazole derivatives (U.S. Patent No. 3,112,197, etc.) and oxadiazole derivatives (U.S. Patent No. 3,1,8,9,4,7, etc.). Reference), imidazole derivatives (for reference), and polyarylalkane derivatives (U.S. Patent No. 3,6,5,402, the same as No. 3,820,98,9, the same specification) Japanese Patent Publication No. 3,542,544, Japanese Patent Publication No. 45-5-5, Japanese Patent Publication No. 51-1978, Japanese Patent Application Laid-Open No. No. No. No. No. No. No. No. No. No. No. No. No. No. No. Japanese Patent Publication No. 55-108667, Japanese Patent Application Laid-Open No. 55-156953, and No. 56-3 66 5-6, etc., pyrazoline derivatives and pyrazole derivatives (U.S. Patent No. 3,180,729) The specification is the same as in the specification of the Japanese Patent Publication No. 4,278,746, the Japanese Patent Application Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. 55-510. -88141, the same as 57-45545, the same as the 54-H2637, the same as the 55-74 546, etc.), the phenyldiamine derivative (US) Japanese Patent Publication No. 3,6 1 5,404, Japanese Patent Publication No. 51-1〇1〇5, the same as No. 46-3712, the same as No. 47-25336, and Japanese Patent Publication No. 54-5343, the same as 54-1 1 053 No. 6, No. 54--121-200920180 1 1 9925, etc.), arylamine derivatives (US Patent No. 3,567,450, the same as No. 3,180,703, the same as No. 3,240,597, the same No. 3, 658, 520, the same as the 4th, 232, and 103th, the same as the 4th, 175, 961, the same as the 4th, 012, 376, the 4th, 012, 376, the Japanese Patent Publication No. 49_357〇2, the same as 39_27577, the special opening 55-144250, the same 56-119132 No. Bulletin, No. 56-22437, No. 56-22437, the reference book for the West, and a substitute for the Chalcone derivative (US Patent No. 3, 5 2 6, 5 0 1 for reference) ), a chewing azole derivative (disclosed in the specification of U.S. Patent No. 3,25, 203, etc.), a styrene-based hydrazine derivative (for reference, JP-A-56-46234, etc.), an anthrone derivative (Special opening) 54- 1 1 083 7th bulletin, etc.), 腙 derivative (US special Japanese Patent Publication No. 3,717,462, Japanese Patent Application Laid-Open No. SHO-54-59143, No. 55-52063, Japanese Patent Publication No. 55-52064, Japanese Patent Publication No. 5-5-4676, No. 55-85495, and No. 57-11350 Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Japanese Patent Publication No. 61-72255, No. 61-72255, No. 62-47646, No. 62-36674, No. 62-10652, No. 62-30255, and No. 60-93455, the same as 60 -94462, the same as the 60-174749, the same as the 60-1 7 5 5 2, etc.), the decazane derivative (US Patent No. 4,950,950), and the 矽; Japanese Unexamined Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. (especially thiophene oligomers) and the like. The hole injecting material may be exemplified by the above-mentioned porphyrin compound (expressed by JP-A-63-295695, etc.), an aromatic tertiary amine compound, and a styrylamine compound (US Patent No.) 4,1 2,7,1 2, and Japanese Patent Laid-Open No. 53-27033, the same as No. 54-58445, the same as No. 54-149634, the same as No. 54-64299, the same as No. 55-79450, the same It is preferable to use an aromatic tertiary amine compound in particular, in the case of the above-mentioned Japanese Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Further, in the case of having two condensed aromatic rings in the molecule described in U.S. Patent No. 5,061,569, for example, 4,4'-bis(N-(1-naphthyl)-N-anilino)biphenyl (hereinafter referred to as Further, 4,4',4"-parameter (N-(3-methylphenyl)) in which three triphenylamine units are linked in a starburst manner as described in JP-A-4-308688 -N-anilino)triphenylamine group (hereinafter abbreviated as MTDATA), etc. Further, Patent Publication No. 3 6 1 440 5, 3 5 7 1 977 or US Patent 4,78 0,5 3 6 An azatribenzophenone derivative or the like can also be used as a hole injecting material. Further, an inorganic compound such as P-type Si or p-type SiC can also be used as a hole injecting material. The hole injecting layer and the hole transporting layer are Helps to inject the hole into the light-emitting layer into the layer of the light-emitting layer, the hole mobility is large, and the ionization energy is generally less than 5 · 5 eV. As such a hole injection layer and hole -123- 200920180 The material of the transport layer is preferably a material that can transport holes to the light-emitting layer at a lower electric field strength, and the mobility of the hole is, for example, 1〇4~ When the electric field of 106 V/cm is applied, it is preferably 1 (T4 cm 2 /V. or more. The material of the hole injection layer and the hole transport layer is not particularly limited, and any material selected from the past may be used as the light-conducting material. A person skilled in the charge transporting material of the electric hole or a hole injecting layer and a hole transporting layer used for the organic EL element. For the hole injection layer and the hole transport layer, for example, the following formula can be used. Amine derivative Ar2'/N-|_|Ar22 Ar206 Avian 207-Ar212--Ar213--Ar223- r211

Ar208

Ar221

P, N.

Ar203' and Ar204 are each substituted or unsubstituted (wherein Ar211 to Ar213 and Ar221 to Ar223 are substituted with an aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted core having 5 to 50 atoms). Aryl, Ar2〇3~Ar2〇8 are each substituted or unsubstituted aryl group having a core number of 6 to 50, or a substituted or unsubstituted heteroaryl group having a number of cores of from 0 to π. a~c and p~ r is an integer of 〇~3. Ar2Q3 and ^2〇4,

Ar2. 5 and 'Ar2〇7 and "8 can be linked to each other to form a saturated or unsaturated ring." Specific examples of the substituted or unsubstituted aryl group having a core carbon number of 6 to 5 are phenyl, 1 _Naphthyl, 2_A certain π-based fluorenyl-fluorenyl, 2-fluorenyl, 9-fluorenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthryl, Buding Province-124- 200920180 base, 2-butyl biphenyl, 3-: phenyl-3-yl, phenyl-3-yl, tolyl, P-naphthyl, 4-methyl-4"-t- Butyl-P. As an example, a pyridyl group, a 3-mercapto group, a 4-isodecyl group, a fluorenyl group, a hexyl group, a 2-benzofuranyl group may be mentioned. , benzyl, 3-isophenyl, 6-isophenyl, 4-quinolyl, 1-isoquinoyl, 6-isoquinoyl, 5-quinoxalyl, 4-yl, 9-butyl , 1_fluorenyl, 2-indenyl, 4-fluorenyl, 2-biphenyl, 4-biphenyl, P-diphenyl-4-yl, P-triplex p_terphenyl-2-yl , m-diphenyl-4-yl, m-tripy m-terphenylphenyl-2-yl, 0-tolyl, tolyl, Pt-butylphenyl, P-(2-phenylpropyl Phenyl, 3-methyl-2-yl-1-naphthyl, 4-methyl-1-indenyl 4'-methyl-biphenyl, - terphenyl-4-yl. Specific examples of the exoaryl group having a nuclear carbon number of 6 to 50 which is substituted or unsubstituted. The aryl group is a group obtained by removing one hydrogen atom. Specific 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 4-pyridyl, ;-_吲 of a heteroaryl group having a nuclear atom number of 5 to 50 or not. Sulfhydryl, 2 _ fluorenyl, 3 _ fluorenyl, 5- fluorenyl, 6 吲哚 fluorenyl, 7 吲哚 fluorenyl, 1 _ 2-isoindolyl, 3-isoindolyl, 4 -isodecyl, 5-isoisoindolyl, 7-isoindolyl, 2-indolyl, 3-furfurfuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzene 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranfuranyl, 4-isobenzofuranyl, 5-isobenzofuranfuranyl, 7-isobenzofuranyl, Quinolinyl, 3-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinolinyl, 3-isoquinolyl, 4-isosinolinyl, 5 -isoquinolinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinolyl, 6-quinoxalinyl, buxazolyl, 2-oxazolyl, 3-flavor Azyl, 9-carbazolyl, fluorenylpyridinyl, 2-phenanthryl, 3-125-200920180 phenanthryl, 4-phenanthryl, 6-phenanthryl, 7-phenanthryl, 8 - phenanthryl, 9-phenanthryl, 1 0-phenanthryl, 1 - Pyridyl, 2-anridinyl, 3-anridinoyl, 4-anridinoyl, 9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl 1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1 , 7-phenanthroline-9-yl, 1, 7-phenanthroline-1 0-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1, 8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8- Phenanthroline-9-yl, 1,8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthrene Benzan-4-yl, 1,9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline 8-based, 1,9-phenanthroline-1 0-yl, 1,1 0-phenanthroline-2-yl, 1,1 0-phenanthroline-3-yl, 1,1 0-phenanthrene Benzin-4-yl, 1,1 0-phenanthroline-5-yl, 2,9-phenanthroline 1-yl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline 4-yl, 2,9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8 -yl, 2,9-non-cyclolin-10-yl, 2,8-non-anthene-1-yl, 2,8-non-cyclolin-3-yl, 2,8-phenanthroline-4 , 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl, 2,8-phenanthroline-1 0-yl, 2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2 , 7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7 -phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazine, 2-phenothiazine, 3-phenothiazine, 4-phenothiazine, 1 0 - phenothiazine, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenyloxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, 2-oxazolyl, 4 -oxazolyl, 5-oxazolyl '2-oxadiazolyl, 5-oxadiazolyl, 3-furazinyl, 2-thiol-126- 200920180, 3-thiol, 2-methyl Pyridyl-i-yl, 2-methylpyrrol-3-yl, 2-methylindole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-bry, 3_ Methylpyrrole-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-t-butylpyrrole-4-yl, 3 _(2 _phenylpropyl Pyrrole-buyl, 2-methyl-1-indenyl, 4-methyl-1-indenyl, 2-methyl-3-indolyl, 4-methyl Base 3 - fluorenyl, 2-t-butyl 1-indenyl, 4-t-butylindolyl, 2-t-butyl 3-indenyl, 4-t-butyl 3 _吲哚基. Specific examples of the substituted or unsubstituted heteroaryl group having a core carbon number of 6 to 50 include a group obtained by removing one hydrogen atom from the above heteroaryl group. Further, the 'hole injection layer and the hole transport layer may not contain a compound represented by the following formula.

(-rl Ul-I , At*'J 丽λ 2^4. ~A r is an aryl group having 6 to 50 nucleus having a substituted or unsubstituted nucleus, or a substituted or unsubstituted nucleus atom number: 〜5 〇 Heteroaryl. L is a linking group, a single bond, or a substituted or unsubstituted aryl group having a nucleus number of ό~50, or a substituted or unsubstituted heteroaryl group having a core number of 5 to 5 Å. Is an integer from 0 to 5)

Ar232ISi Ar233'K'-j-D^r Eight Red phases can be joined to form a saturated or unsaturated ring. -127- 200920180 wherein the aryl and extended aryl groups having a substituted or unsubstituted nucleocarbon number ό~50, and the substituted or unsubstituted heteroaryl group and heteroaryl group having a nuclear atom number of 5 to 5 Å Examples are the same as described above. Specific examples of the material of the hole injection layer and the hole transport layer include a triazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, and a pyrazoline derivative. , pyrazole g-derivative, phenyldiamine derivative, arylamine derivative, amine-substituted chalcone derivative, oxazole derivative, styrylpurine derivative, anthrone derivative A substance, an anthracene derivative, a stilbene derivative, a decazane derivative, an aniline-based cohesive body, a conductive polymer oligomer (particularly a thiophene oligomer), and the like. As the material of the hole injection layer and the hole transport layer, the above may be used, but a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound are preferred, and an aromatic tertiary amine compound is particularly preferred. Further, a compound having two condensed aromatic rings in the molecule is used, for example, an NPD or a triphenylamine unit is used to connect to 4 starburst type 4, 4, 4"-parameters (!^-(3-A) Phenylphenyl)-phenylamino)triphenylamine (hereinafter abbreviated as MTDATA) or the like is preferred. Other nitrogen-containing heterocyclic derivatives represented by the following formula may also be used. -128- 200920180

In T, R2. 1 to R2. 6 are each substituted or unsubstituted carbon number alkyl-substituted or unsubstituted aryl group having a carbon number of 6 to 50, substituted or unsubstituted carbon number of 7 to 5 Å. Any one of an aralkyl group, a substituted or unsubstituted heterocyclic group having a nuclear atom number of 5 to 5 Å. R2(m and r2()2, r2()3 and r2Q4, r2〇5 and with R2Q3, or R2M and r2G5 can form R206, r20

With R 2 0 6

R 2 0 2 condensed ring. Compounds of the formula below can also be used. R211 R212

216 r211 to r2 16 are an electron-attracting group of a substituent, preferably a cyano group, a nitro group, a sulfonic acid group, a carbonyl group, a trifluoromethyl group or a halogen. Further, an inorganic compound such as P-type Si or p-type SiC can also be used as a material for the hole entry layer and the hole transport layer. Hole injection layer and hole transport layer - 129 - 200920180 The above-mentioned compound is formed by thin film formation by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. The film thickness of the hole injection layer and the hole transport layer is not particularly limited, but is generally 5 nm to 5 μm. The hole injection layer and the hole transport layer may be formed of one or more layers of the above materials, or may be formed by laminating a plurality of hole injection layers and hole transport layers formed by different compounds. . Further, an inorganic compound such as p-type Si or bismuth-based Sic can also be used as a material for the hole injection layer. A compound of the following formula can also be used as a hole injection layer. R1

In the formula, 'R1 to R6' represent a halogen, a cyano group, a nitro group, an alkyl group or a trifluoromethyl group, and each may be the same or different. Further, R1 to R6 are preferably a cyano group. The hole injection layer is formed by, for example, thinning the above compound by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an L B method. The film thickness of the hole injection layer is not particularly limited, but is generally 5 nm to 5 μm. -130- 200920180 Next, the luminescent blend is explained. As the fluorescent blend blended in the fluorescent light-emitting layer, it is not preferable to obtain a white color as a whole of the element, and a blue light which is difficult to obtain by the light-emitting light. The fluorescent blend may be exemplified by the following formula: (20) In the formula (2〇), 'P represents a substituted or unsubstituted nucleus carbon number of 6 to 40. Aromatic hydrocarbon group, substituted or unsubstituted nuclear atom number 3~ a substituted or unsubstituted styryl group of a heterocyclic group of fluorene. ]^ is an integer of 丨~3.

Ar1 to Ar4 each independently represent a substituted or unsubstituted nucleus carbon number 6 to a fragrant sulphur group, or a substituted or unsubstituted nucleus having a number of core atoms of from 3 to 40 is an integer of from 0 to 4. 1 2

Any two adjacent substituents selected in Af 'At 'p are combined with each other to form a ring. When k is 2 or more, p may be the same or different. Examples of the sulfonate-saturated hydrocarbon group and the heterocyclic group include an aromatic hydrocarbon group having 6 to 4 fluorene substituted groups, substituted or unsubstituted white lice. a heterocyclic group of 3 to 40, for example, benzene, biphenyl, bispyrene, phenanthrene, fluoranthene, anthracene, anthracene, anthracene, anthracene, sulfonium, quinone, dinaphthyl, benzyl, onion, and Phenyl hydrazine, hydrazine, tribenzo benzene, Rubrene, benzoquinone, diphenyl hydrazine, fluoranthene, tribendive, wavelength limit

Aromatic, or 40, heterocyclic, reciprocal: or no I nucleoside: ketone, trinaphthalene fluoranthene-131 - 200920180 茈 茈 residues, especially 蒽 蒽, diphenyl fluorene and fluoranthene The residues of benzofluoranthene, benzofluoranthene, di-naphthalene, phenanthrene, fluoranthene, anthracene, anthracene, anthracene, porphyrin, residue and plural are preferred. In the formula (20), each of Ar1 to Ar4 independently represents an unsubstituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 40 nuclear atoms, and s is An integer from 0 to 4. Examples of the aromatic hydrocarbon group of Ar1 to Ar4 include a phenyl group, an i-nyl group, a 2-naphthyl group, a fluorenyl group, a 2-onion group, a 9-fluorenyl group, a phenanthryl group, a 2-phenanthryl group, and 3 - Fickey, Renfiki, 9_Fiki, 丨_丁省基, 2·丁省基, 9_丁省基,; _芘 base, 2_ fluorenyl, 4_ fluorenyl, 2_biphenyl Base, 3_biphenyl, 4-biphenyl, ? _Linotriphenyl-4-yl, b-triphenyl-3-yl, p-bi-diyl-2-yl'm-biphenyl-4-yl, m-bitriphenyl-3 ·Base, cardinal dibenzyl-2-yl, fluorenyl-tolyl, m-tolyl, ρ-tolyl, p_t_butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl 4-naphthyl, 4-methyl-oxime-naphthyl, 4-methyl-1-indenyl, 4'-methylbiphenyl, 4,-t-butyl-P-bitriphenyl Base-4-yl and the like. Examples of the heterocyclic group of Ar1 to Ar4 include a 1-pyrrolyl group, a 2-portylpyryl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-lanyl group, and 1 · fluorenyl, 2 _ fluorenyl, 3 _ fluorenyl, 4- fluorenyl, 5 _ D fluorenyl, 6-fluorenyl, 7-fluorenyl, 1-isodecyl, 2 -isoindenyl, 3-isoindenyl, 4-isodecyl, 5-isodecyl, 6-isodecyl, 7-isodecyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-iso-132- 200920180 benzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, quinolyl, 3- Quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4- Isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoline Porphyrin, 1-razozolyl, 2-oxazole , 3-oxazolyl, 4-oxazolyl, 9-isoxazolyl, 1-non-B-fluorenyl, 2-non-D-decyl, 3-nonindolyl, 4-non-D-decyl, 6-non B-mercapto, 7-non-D-mercapto, 8-phenanthrene-B-yl, 9-non-indenyl, 10-non-D-yl, Ι-nf fluorenyl, 2-B 丫D 疋, 3 - tff II fluorenyl, 4 - D丫D fluorenyl, 9 - Π f fluorenyl, 1,7-non-cyclopentan-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthrene啉-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline- 9-yl, 1,7-phenanthroline-10-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4- 1,1,phenanthroline-5-yl, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl, 1,8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1, 9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9- Phenanthroline-10-yl, 1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,1 0-phenanthroline-4-yl, 1, 1 0 -phenanthroline-5-yl, 2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl, 2, 9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl, 2,8- Phenanthroline-4-yl, 2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl, 2,8-phenanthrene Porphyrin-9-yl, 2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl, 2,7-phenanthroline-133- 200920180 oxa-3-yl, 2,7- Phenanthroline-4-yl, 2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthrene Rung-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazine, 2-phenothiazine, 3-phenothiazine , 4-phenothiazine, 10-phenothiazine, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenyloxazinyl, 4-phenoxazinyl, 10-phenoxazinyl , 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furenyl, 2-thiol, 3-thiol , 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyridin-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole- 1-based, 3-methylpyrrol-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrol-5-yl, 2-t-butylpyrrol-4-yl, 3-( 2-phenylpropyl) lysyl-1-yl, 2-methyl-1-D-derived D-, 4-methyl-1-D fluorenyl, 2-methyl-3-indenyl, 4-methyl-3-indolyl, 2-t-butyl 1-indenyl, 4-t-butyl 1-indenyl, 2-t-butyl 3-indenyl, 4-t - Butyl 3-indenyl and the like. Specific examples of the amine compound represented by the formula (20) are condensed aromatic amine, styrylamine, benzidine, etc., but are not limited thereto. And,

Me represents a methyl group. -134- 200920180

-135 200920180

6T(V) 8T(V) ZT(V) 9"7(<

S-(v)CSICN-(V) i(v) OCNJ-(V)

ZCNI-(V) 9cnj-(v) 9c\i-(v) 义义<) -136- 200920180 σ

S-(v) 9ε-(V) ζε-(ν) 9ε_<) -137- 200920180

CN11V) T-iv)

ΩΙΛΙ

CNIs-<)

Q 3IAI0L Nω1ΛΙ

9HV) ω1ΛΙ

——9-(ν)

11ΛΙ os_(v) s'(v)

o inch - (V)

5-(v)

61V) -138 200920180

-139- 200920180

CNZ-(V) (υΙΛΙ ιζ_(ν) οζ—(ν)

.9ΙΛΙ ΟΙΛΙ I

Ucr

ωΙΛΙ 32 ζζ·(ν)

9Z_(V) ΘΙΛΙωιΛΙ 9|/\|9一/\| i sz-(v)

Inch ζ-(ν) -140 200920180 91λιλ91λι ωΙΛΙ 1 ΙΛΓωΙΛΙ

ι'(ν) ωιΛΙ ωΙΛΙωΙΛΙ ·3ΙΛΙ

§-(<) ω1ΛΙφΙΛΙ 1ΙΛΙ

S-(v) ωΙΛΙωΙΛΙφΙΛΙ

1 ΙΛΙωΙΛΙ ω1ΛΓωΙΛΙ

6Ζ person V) ωΙΛΙ 1ΙΛΙ ωΙΛΓωΙΛΙ 9ΙΛΙ- ωΙΛΙωΙΛΓ91ΛΙ

ΩΙΛΙω1ΛΙ ε8·(ν) ωΙΛΙ-ΘΙΛΓωιΛΙ

91ΛΙωΙΛΙ ωΙΛΙ ωΙΛΙ i _ω1ΛΙω1ΛΙ ζ·(ν) ωΙΛΙ 1ΙΛΙ1ΙΛΙ Φ5 csloo-(v) ωΙΛΙ (υΙΛΓωΙΛΙ

ωΙΛΙ 1ΙΛΙ 1ΙΛΙ 99έ 200920180

S-(v) s-(v) δν) 06-(v)

Oov(v) 66-(v) 96-( V) -142- 200920180

91ΛΙ

Οοοτ(ν) ζοτ(ν) 9°·(ν) ωΙΛΙ Ρ -143- 200920180

9U-(V) m-(v)

Sl4-{< -144- 200920180

OOCNIV(V) ZCNIT(V) ΘΙΛΙΘΙΛΙ ωΙΛί ΦΙΛΙ 93-V) 63τ(ν) -145- 200920180 ΘΙΛΙ-^^ωιΛΙ ΦΙΛΙ

9ΙΛΙ-1ΙΛΓωιΛΙ οετ(ν)

6εν(ν) ΦΙΛΙ > ω1ΛΙ ΦΙΛΙ > ΦΙΛΙ αα

Ρ Q ··1/9ΙΛΙ Γ 9ΙΛΙ r

ΩΙΛΙ 8ετ(ν) ΦΙΛΙ

9|Λ| ζετ(ν) 146- 200920180

Sn-(v) εη·(ν)

Ζκ-(ν)

ωΙΛΙ(υ1ΛΙ 9 inches τ(ν) -147- 200920180 9ΙΛΙΟ

α 0JroT_^ οιητ(ν)

6Η-(ν)

Ο1ΙΛΙ

OOST(V) SAV)

9ST(V) SL-(<) όττοτ^ οοη person V) α όττότ^ 5_(<)

3T(V)

-148- 200920180

-149 - 200920180 EM41

—CH=CH

(A)-171

-150- 200920180

EM48 (A )-176 (A )-177

(A )-178 (A )-179 EM50

CH = CH 200920180 EM51

(A)-181

(A)-182 (A)-183 (A)-184

Me Me -152- 200920180

EM57 EM58

(A)-187 (A)-188

(A)-189 EM60

-153- 200920180

-Ο (A)-194 Or CH=CH (A)-193

CH=CH—<Q) (A )-195

Further, it may be a compound containing an oxazole group as follows. -154- 200920180

(A)-164 In the present invention, the fluorescent dopant blend is preferably a fluoranthene derivative represented by any one of the following formulas (5) to (8). -155- 200920180

In the formulae (5) to (8), X1 to X52 each independently represent a hydrogen atom, a halogen atom-156-200920180, a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 3 carbon atoms. , substituted or unsubstituted linear, branched or cyclic carbon atoms! 〇3〇 alkoxy, substituted or unsubstituted linear, branched or cyclic alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic carbon atom number 2 〜30 alkenyl, substituted or unsubstituted linear 'branched or cyclic alkenyloxy group having 2 to 30 carbon atoms, substituted or unsubstituted linear 'branched or cyclic carbon number 2 to 3 An alkenylthio group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 30 carbon atoms, a substituted or unsubstituted carbon atom number 7 〇 3 芳 aralkylthio group, substituted or unsubstituted aryl group having 6 to 2 Å carbon atoms, substituted or unsubstituted aryloxy group having 6 to 碳 carbon atoms, substituted or unsubstituted carbon atom a 6 to 20 arylthio group, a substituted or unsubstituted amino group having 2 to 30 carbon atoms, a cyano group, a decyl group, a hydroxyl group, a _c〇〇Ri group (wherein R1 represents a hydrogen atom, a substitution or An unsubstituted linear, branched or cyclic alkyl group having a carbon number of from 〜30, a substituted or unsubstituted linear, branched or cyclic alkenyl group having from 2 to 30 carbon atoms. Or an unsubstituted aralkyl group having 7 to 30 carbon atoms or a substituted or unsubstituted aryl group, -C〇R2 group (wherein R 2 represents a hydrogen atom, a substituted or unsubstituted direct bond) , branched or cyclic carbon atom number 〜3〇 alkyl group, substituted or unsubstituted linear bond, branched or cyclic 2 to 3 fluorene alkenyl group, substituted or unsubstituted carbon atom number 7 An aralkyl group of ～30, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or an amine group, and a 〇〇c〇R3 group (wherein v represents a substituted or unsubstituted linear chain, a branch or A cyclic, carbon atom number 1 to fluorenyl group, substituted or unsubstituted linear, branched or cyclic carbon atom number 2 - 157 - 200920180 〜 3 0 alkenyl group, substituted or unsubstituted carbon atom number 7 ～30 aralkyl, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and in X1 to X52, the adjacent groups and the substituents of the respective groups may be bonded to each other to form a substituted or unsubstituted carbocyclic ring. As such a fluoranthene derivative, the following are mentioned, for example. -158- 200920180

-159- 200920180

-160- 200920180

200920180

-162 - 200920180

-163- 200920180

-164- 200920180

-165- 200920180

-166- 200920180

-167- 200920180

-168- 200920180

-169 200920180

90 τι. CNIOV 66Η 170- 200920180

200920180

σ> τ ι CNJ

00 τ ι CM

-172 200920180

-173- 200920180

-174- 200920180

-175- 200920180

In the present invention, the fluorescent light-emitting blend may be represented by the following formula. -176- 200920180

(Xb)m where A and A' represent a corresponding pyridazine ring system 'Xa and Xb corresponding to a 6-membered aromatic ring containing one or more nitrogens, each independently selected substituent' A condensed ring corresponding to A or A' is formed, and m and η each independently represent 0 to 4'. Za& Zb are each independently selected substituents, !, 2, 3, 4, 1', 2', 3' and 4 'As a carbon atom or a nitrogen atom, it is independently selected. 1, 2, 3, 4, 1', 2', 3, and 4' of the pyridazine ring are all carbon atoms, m and η are 2 or more ' and Xa and Xb are combined to represent the formation of the aromatic ring 2 Preferably, a sinoline ring or an isoquinoline ring of more than one carbon substituent is preferred. Preferably, za and Zb are fluorine atoms. Preferred examples are as follows: two condensed ring systems are quinoline or isoquinoline-based 'aryl or heteroaryl substituent is phenyl'. At least two Xa groups are bonded when a 6-6 condensed ring is formed. And two Xb groups, the condensed ring system is condensed at each i _ 2 position, 3-4 position, 1 '-2' position or 3 '-4' position, and one or both of the condensed rings are substituted by a phenyl group, and A fluorescent blend as shown by the following formula (91), (92) or (93). -177- 200920180

base. 1, 2, 3, 4, 丨, 2, 3, and 4' of the mouth ring are all carbon atoms, and m and η are 2 or more 'Xa and Xb represent 2 combinations when forming an aromatic ring It is preferred that the above carbon substituent 'and one is an aryl or substituted aryl quinoline ring or isoquinoline ring. Za and fluorine atoms are preferred. The following is a exemplified boron compound in which two ring nitrogens are deprotonated with a bis(oxazinyl)amine ligand, and the two ring nitrogens are different 6,6 condensed ring systems, of which at least 1 The ones are boron compounds useful in the present invention having a composition of an aryl or heteroaryl substituent. -178- 200920180

Next, the following is mentioned as a luminescent compound. That is, it is preferred to contain a metal complex formed of a metal selected from the group consisting of Ir, Pt, Os, Au, Cu, Re, and Ru and a ligand. Specific examples of the luminescent complex include, for example, PQIr(iridium(III)bis(2-phenyl quinolyl-N, C2, ac ety 1 ac et ο nate) ' Ir (ppy ) 3 ( f ac In addition to -1 ris (2 - pheny 1 py rid in e) iridium), the following compounds may also be mentioned. -179- 200920180

-180- 200920180

200920180

CF3

-182- 200920180

In the present invention, the organic thin film layer has an electron injecting layer between the cathode and the mixed color light-emitting layer. The electron injecting layer preferably contains a nitrogen-containing ring derivative. When a nitrogen-containing ring derivative having high electronic properties is used as an electron injecting and transporting layer, the driving voltage can be lowered. In particular, in the present invention, the light-emitting layer (the fluorescent light-emitting layer and the phosphorescent light-emitting layer) is composed of a main material of a wide gap as compared with a main material (for example, an anthracene derivative) of the conventional fluorescent light-emitting layer, so that the charge is The injection barrier becomes larger and may be related to the increase in the driving voltage of -183- 200920180. This can avoid the rise of the driving voltage by having an electron transporting layer having a high electron transporting property. The electron injecting layer is preferably one containing a nitrogen-containing ring derivative. When such a nitrogen-containing ring derivative having high electronic properties is used as an electron injecting and transporting layer, the driving voltage can be lowered. As the material used for the electron injecting layer or the electron transporting layer, a metal complex of 8-hydroxyquinoline or a derivative thereof, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative is preferred. Specific examples of the metal complex of the above 8-hydroxyquinoline or a derivative thereof include a chelated metal chelate oxynoid compound containing oxine (usually 8-oxo or 8-hydroxysalthorphyrin), for example, A ginseng (8-quinolinol) aluminum can be used. As the oxadiazole derivative, the following general formula [29] to [31] can be cited.

Ar17

Ar18

[29] [30] [31] (wherein, Ar17, Ar18, Ari9, Ar21, Ar22 and Ar25 represent an aryl group having or not having each substituent, and Ar17 and Ar18, Ar19 and Ar21, and Ar22 and Ar25 may be The same or different. Ar2, Ar23 and Ar24 represent an electron-transporting compound represented by an extended aryl group having or not having a substituent, and Ar23 and Ar24 may be the same or different from each other. -184- 200920180 Examples of the aryl group in the general formulas [29] to [31] include a phenyl group, a biphenyl group, a fluorenyl group, an anthracenyl group, an anthracenyl group and the like. Further, examples of the aryl group include a stretching phenyl group, a stretching naphthyl group, a stretching phenyl group, a stretching thiol group, a stretching thiol group, and a stretching thiol group. Further, examples of the substituents thereof include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a cyano group. The electron-transporting compound can be preferably used in which film formability is good. Specific examples of these electron-transporting compounds include the following.

The organic compound of the general formula is a nitrogen-containing heterocyclic derivative, and a nitrogen-containing compound having a non-metal complex formed of a τ compound is mentioned. -185 - 200920180 VIII · · · (A) K1 ?2 • · · (B (wherein χ represents a carbon atom or a nitrogen atom. Ζι and Z2 each independently represent an atomic group capable of forming a nitrogen-containing hetero ring)

Preferably, the nitrogen-containing aromatic polycyclic ring having a 5-membered ring or a 6-membered ring is a plurality of nitrogen atoms having a skeleton, wherein the skeleton has a bonding position which is not adjacent. Further, the case of the nitrogen-containing aromatic polycyclic group having such a plurality of nitrogen atoms is a nitrogen-containing aromatic polycyclic organic compound having a skeleton in which the above (A) and (B) or (A) and (C) are combined. The nitrogen-containing group (H Ar) of the nitrogen-containing organic compound is selected from the following general formula -186- 200920180

(wherein R is an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, a group having 1 to 20 carbon atoms, or a oxy group having 1 to 20 carbon atoms, and η is 0 to 5 An integer, when η is an integer of 2 or more, the plural R may be the same or different from each other) a nitrogen-containing heterocyclic derivative of a nitrogen-containing heterocyclic group. As a more preferable specific compound, a nitrogen-containing heterocyclic derivative represented by the following general formula is mentioned. -187- 200920180 HAr—L1—Ari, Ar2 (in the formula, HAr

a single bond, a nitrogen-containing heterocyclic ring having a carbon number of 3 to 40 which may have a /κ group, a aryl group having 6 to 40 carbon atoms which may have a substituent or a carbon number of 3 to 40 which may have a substituent Arylene group, Ar1 is a divalent aromatic hydrocarbon group having 6 to 40 carbon atoms which may have a substituent, and Ar2 is an aryl group having 6 to 40 carbon atoms which may have a substituent or a carbon number of 3 to 40 which may have a substituent Heteroaryl) is a nitrogen-containing heterocyclic derivative. Also, the HAR is selected from

-188- 200920180 A group of nitrogen-containing heterocyclic derivatives. L is selected from

Groups of nitrogen-containing heterocyclic derivatives. Ar2 is selected from

Groups of nitrogen-containing heterocyclic derivatives. Ar1 has a general formula

(wherein R1 to R14 are each independently a hydrogen atom, a halogen atom, a carbon number: a hospital group, a carbon number of 1 to 20, and an aryloxy group having 6 to 40 carbon atoms which may have a carbon number of 6 Nitrogen-containing heterocyclic ring derived from aryl group of aryl group or aryl group containing aryl group of aryl group or aryl group of aryl group or aryl group having aryl group of aryl group or aryl group Things.

In Ar1, all of R1 to R8 are nitrogen-containing heterocyclic derivatives of a hydrogen atom. Others can be cited in the special report 9-344 8 ~ 20 base, miscellaneous -189- 200920180

Ri X2 R2-N

M-r4

Xi R3 (wherein, 1 to 114 each independently represent a hydrogen atom 'substituted or unsubstituted aliphatic K group, substituted or unsubstituted aliphatic cyclic group, substituted or unsubstituted magnetic cyclic aromatic ring group, a substituted or unsubstituted heterocyclic group, Χι, X2 each independently ii· represents an oxygen atom, a sulfur atom or a dicyanomethyl group), or R1\ /R2 described in JP-A-2000 173774

II HIC

HIC II HIC

• ( 51) [However, in the above general formula (51), R1, R2, R3 and R4 may be the same or different from each other, and the aryl group represented by the following general formula (52)

52 (However, in the above general formula (52), R: R (

R R8 and R 9 may be the same or different from each other, or at least one of them may be a saturated or unsaturated alkoxy group, an alkyl group, an amine group or an alkylamino group)] -190- 200920180, etc. Conditional organic compounds. Further, it may be a compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing hetero molecule. The film thickness of the electron injecting layer or the electron transporting layer is not particularly limited to 1 to 10 nm. In the present invention, it is preferred to add a reducing blend to the cathode and the organic thin film. Thus, the illuminating brightness of the organic EL element can be achieved. Among them, the so-called reducing blend is defined as a substance of a reducible compound. Therefore, for example, at least one selected from the group consisting of an alkali metal, a rare earth metal, an alkali metal oxide, an alkali metal earth metal oxide, and an alkaline earth metal halide can be used. A halide of an oxide or a rare earth metal, a metal-based organic complex of an alkali metal, or an organic complex of a rare earth metal is preferred. Further, a more specific preferred reductive blend is, to Li (work function: 2.9 eV), Na (work function: 2.36 eV) 2.28 eV) 'Rb (work function: 2_16 eV) and Cs (work function! The group of alkali metals, or at least one selected from the group consisting of Ca (work function Sr (work function: 2.0 to 2.5 eV), and Ba (work function: alkaline earth metal, with a work function of 2.9 eV or less, preferably reduced) The blend is at least one selected from the group consisting of K and a ring derivative. The preferred interfacial region is improved or the long-lived electron transportability is possible. The halides and alkali rare earths of each genus, alkaline earth gold can be used. The metal-like machine body and the alkaline earth group are less than one species selected from the group consisting of K (work function: 汝:1 9 5 e V): 2_9eV), !. 5 2 e V) It is especially good for Rb and Cs to form -191 - 200920180 group of alkali metals, more preferably Rb or Cs' is preferably Cs. These reducing powers are extremely high, and can be added by the electron injection area. A reduction blend having an increase in luminescence brightness and longevity in an organic EL device, and a reductive blend having a work function of 2.9 eV or less, preferably a combination of more than one kind of alkali metal, particularly The group of Cs such as Cs and Na, Cs and K, Cs and Rb or Cs and Na and K are preferred. By combining Cs, the reduction can be efficiently performed by adding electron injection regions to achieve organic EL. In the present invention, the anode of the organic EL element has a function of injecting a hole transport layer or a light-emitting layer, and has an effect of 4.5 eV or more. The anode material used in the present invention is used. Specific examples thereof include indium tin oxide alloy (ITO), tin oxide (NESA), gold, silver, etc. Further, as the cathode, it is preferred to inject a material having a small work function in the electron injecting layer or the light emitting layer. The cathode material is not determined to specifically use indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum-lithium alloy, aluminum-niobium-lithium alloy, magnesium-silver alloy, etc. Layers of the organic EL element of the present invention The formation method is not limited. A conventionally known method such as a vacuum deposition method or a spin coating method can be used. The organic thin film layer containing the compound of the above formula used in the organic EL device of the present invention can be subjected to vacuum evaporation or molecular line. (Μ BE method) or dissolve The coating method such as the solution immersion method of the solvent, the spin coating method, the bar coating method, or the roll coating method is formed by a known method, and the thickness of each organic layer of the organic EL device of the present invention is not increased by the amount of alkali metal.命化. : These two combinations, the combination of the ability, the power to the hole function function can be platinum, copper electrons are special alloys, special limited formation (1) shown by vapor deposition, casting. Limit -192- 200920180, generally, when the film thickness is too thin, defects such as pores are likely to occur. On the contrary, if the thickness is too thick, a higher applied voltage is required to deteriorate the efficiency, and it is generally in the range of several nm to 1 μm. . The organic EL device is fabricated on a light-transmissive substrate. The light-transmitting substrate is a substrate supporting an organic EL element, and it is preferably a smooth substrate having a light transmittance of 50% or more in a visible light region of 400 to 700 nm. Specifically, a glass plate, a polymer plate, etc. are mentioned. Specific examples of the glass plate include soda lime glass, bismuth-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium boron silicate glass, and quartz. Further, examples of the polymer sheet include polycarbonate, acryl, polyethylene terephthalate, polyether sulfide, and polyfluorene. [Embodiment] [Embodiment] The present invention will be described in more detail by way of examples and comparative examples, but the invention is not limited by the description of the examples. The compounds used in the examples are shown in the following table. Further, the physical properties of each of the materials described in the following tables were measured as follows. The triplet energy gap Eg is defined by the luminescence spectrum. Namely, each of the materials was dissolved in EPA solvent (distillation ratio: diethyl ether: isoamyl: ethanol = 5:5:2) at ΙΟμηιοΙ/L, and used as a sample for calender measurement. -193- 200920180 The sample for calender measurement was placed in a quartz container, cooled to 7 7 Torr, and irradiated with laser light to measure the wavelength. For the short-wavelength side front lead-out connecting line of the obtained neon spectrum, 値 which converts the wavelength 値 into energy is taken as the triplet energy gap E g (Τ). Further, the measurement was carried out using a commercially available measuring device F - 4500 (manufactured by Hitachi, Ltd.). The so-called affinity level Ea (electron affinity) is the energy released or absorbed when one electron is imparted to a material molecule, and is defined as positive at the time of release and negative at the time of absorption. The affinity level Ea is defined by the ionization potential Ip and the optical energy gap Eg(S) as follows. A f = I p - E g ' where the ionization potential Ip represents the energy required to extract electrons from each material compound for ionization, for example, by ultraviolet photoelectron spectroscopy (AC-3, 硏 硏) Measured by the meter. The optical energy gap Eg(S) is the difference between the conduction level and the valence electron level, and is obtained, for example, by converting the wavelength 値 of the intersection of the long-wavelength side wiring and the bottom line of the absorption spectrum of the toluene thin solution of each material into energy. -194- 200920180 Table 1

Ea Eg$) EgCT) Compound A 5.88 2.64 3.24 2.38 Compound D 5.98 2.41 3.57 2.89 Compound E 5.95 2.56 3.39 2.72 CBP & Na § 6.06 2.50 3.56 2.81 Blend A d#b 5.47 2.67 2.80 - Compound I i Q Compound J ό 5r(tpil) 2 fecac) i (o^), r^ -195- 200920180 (Example 1) A glass substrate (manufactured by Geomatics Co., Ltd.) having an ITO transparent electrode of 25 mm >< 75 mm x 1.1 mm thick was applied thereto. The propyl alcohol was washed with ultrasonic waves for 5 minutes, and then washed with UV ozone for 30 minutes. The glass substrate with the transparent electrode line after cleaning is assembled on the substrate holder of the vacuum evaporation method, firstly formed on the side of the transparent electrode line, such as 4, 4'-double [N] covering a thickness of 55 nm under the transparent electrode. The -(l-naphthyl)-N-phenylamino]biphenyl film (hereinafter abbreviated as "NPD film") was formed by a film formed by resistance heating. The NPD film can be used as a hole injection and a transport layer to perform its function. Next, the CBP, which is the main material of the red enamel, was formed on the NPD film by a resistance heating shovel to a thickness of 3 Onm. At the same time, Ir(tpiq) 2 (acac) as a red calendering blend was vapor-deposited to a mass ratio of CBP of 5%. The film can function as a red luminescent layer. Next, on the red luminescent layer, CBP, which is a green luminescent main material, was deposited by a resistance heating film to a thickness of 5 nm. At the same time, Ir(ppy) 3 (TriS(2-phenylpyridine)iridium(III)) as a green light-emitting illuminating blend was vapor-deposited to a mass ratio of CBP of 5%. This film functions as a calender light-emitting layer. Further, on the green calendering layer, a compound D as a fluorescent main material was deposited by a resistance heating film to have a thickness of 1 Onm. At the same time, the NPD as a fluorescent luminescent blend was evaporated to a mass ratio of 2% to the compound D. This film functions as a fluorescent light emitting layer. The following compound I was formed on the film to a film thickness of 1 Onm. This functions as an electric barrier of the -196-200920180 hole. And the film was formed on the film to a ginseng (8-salofolic phenol) aluminum (Alq) complex having a film thickness of 30 nm. This can function as an electron transport layer. Thereafter, LiF was formed into a film of 0.5 nm. Metal A1 was vapor-deposited to 150 nm on the LiF film to form a metal cathode, thereby forming an organic EL luminescent element. (Example 2 to Example 10) The compound used was changed, and the element was produced in the same manner as in the above Example 1. The compounds used in the examples are shown in Table 1. Regarding the film thickness and the blend concentration of each layer, the layer having the same function as the layer in Example 1 was the same film thickness and the same blend as in Example 1. Further, in Example 4, an intermediate layer (without a blending layer) was provided, and these intermediate layers had a thickness of 5 nm. In Example 6, as the second fluorescent main material of the second luminescent layer, BAlq was used, and its Eg(T) was 2.28 eV. (Comparative Example 1) The compound to be used was changed, and an element was produced in the same manner as in the above Example 1. In Comparative Example 1, the main materials of the fluorescent light-emitting layer, the green light-emitting layer, and the red light-emitting layer were all CBP. And an intermediate layer is provided between the fluorescent light emitting layer and the green light emitting layer. The film thickness was 5 nm. -197- 200920180 [Table 2] Example 1 NPD/CBP fecac)/CBP: fr(bpy)3/Compound D: NPB/Compound FAlj3/LiVA 1 Example 2 NPD/Compound E: fr(tpii)2 fecac) /CBP :H3py)3Af chelate D NP B/compound FAlq3/LF/A 1 Example 3 NPDA chelate A Gcac) / compound E: Hpy) 3 / compound D: NPB / compound I / A 1} 3 /LF/A1 Example 4 NPD/compound fecac)/compound A/compound E: frfcpy)3/compound E/compound D NP B/compound]/A h3/LF/A 1 Example 5 NPD/Compound D Qing/ Compound E ΑΛ·4ρί]) 2fecacV-doped VA WLF/A1 Example 6 NPD/Compound D NPD/Compound E: frfcpy) 3/BAkf: t(tpii) 2fecac)/A h3/LF/A 1 Example 7 NPDA chelate D: NPD/compound E: H>pyM chelate A: fr(W2^icaC)/compound, compound J/LF/A1 Example 8 NPD/Compound D: Blend A / Compound E :frWy)3/Compound AiftpijSfecac)/Compound I/Ah3/Lf/Al Example 9 NPD/CBP:fr(tpii)2fecac)/Compound D: NPB/Compound I/AljS/LF/Al Example 10 NPD/Compound Airftpi]) 2 fecacV compound D: NPB/compound FA Ij3/L f/A 1 Comparative Example 1 NPD/CBP :fr (tp i)) 2 (k:ac)/CBP :H3py)3/C BP/CBPN PB / compound] / A ] q3 / LF / A 1 [Evaluation of organic EL device] The organic EL device produced as described above is irradiated with a direct current to measure luminescence chromaticity, brightness (L) and Voltage. Thereby, the external quantum efficiency (EQE%) is obtained. Further, the half-life of each organic EL element was measured by a DC continuous power test at an initial luminance of 1 〇 00 nit. The results are shown in Table 3 below. [Table 3] EQE Life @1000nit Example 1 12.4K 300hr Example 2 12.2% 350hr Example 3 13.2% 400 hr Example 4 13.3X 450 hr Example 5 12.8% 400 hr Example 6 11.9% 350 hr Example 7 14.8% 400 hr Example 8 13.1% 450 hr Example 9 13.5* 400 hr Example 10 13.7% 500 hr Comparative Example 1 11.6% 150 hr - 198 - 200920180 It is known from Table 3 'Organic EL elements of the examples 丨~丨3 constituting the elements of the present invention Compared with Comparative Example 1, it shows a longer life and higher efficiency. And 'in this specification' the term "egg light main material and twilight main material" is combined with a fluorescent blend as a fluorescent main material, and a combination with a neon light blend is called a twilight main material, not only a molecule. The structure is defined by a narrow fluorescent main material or a fluorescent main material. In other words, in the present specification, the term "fluorescent main material" means a material constituting a fluorescent light-emitting layer containing a fluorescent blend, and it is not only a main material of a fluorescent material. Similarly, the so-called calender master material means that the material constituting the peculiar light-emitting layer containing the calendering blend is not only the main material of the calendering material. -199-

Claims (1)

200920180 X. Patent Application Area 1. An organic EL element which is an organic EL element having an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin film layer has a light main a fluorescent material of the material and the fluorescent dopant, and a first light-emitting layer containing the first light-emitting main material and the first light-emitting blend, wherein the triplet energy gap of the fluorescent main material is EgfH, when the triplet energy gap of the first luminescent main material is EgPH1, EgfH>EgpHI 〇2 · The organic EL element according to claim 1, wherein EgfH-〇.leV>EgPHi. 3. The organic EL device according to claim 1 or 2, comprising a second luminescent layer comprising a second luminescent main material and a second light-emitting conjugate, the second luminescent main material When the triplet energy gap is EgPH2, EgpHi$EgpH2. The organic EL element of claim 3, wherein the first luminescent layer is disposed between the luminescent layer and the second luminescent layer, and EgpH1 > EgpH2. -200- 200920180 VII. Designated representative map: (1) The representative representative of the case is: No (2), the representative symbol of the representative figure is a simple description: No. 8. If there is a chemical formula in this case, please reveal the best display invention. Chemical formula of the feature: none