Amine compound, and organic electroluminescent element, electronic device, and electronic element each containing same

Abstract

The purpose of the present invention is to provide a compound which absorbs light having a wavelength of 400 nm to 410 nm of sunlight, does not affect the material in the element, and has a high refractive index in the wavelength range of 450 nm to 750 nm, in order to prevent deterioration in the element interior of an organic EL element and greatly improve light extraction efficiency. An amine compound having a specific benzoxazole ring structure and having excellent stability and durability of a thin film of an arylamine material and a high design refractive index is used as a material constituting a capping layer, thereby obtaining an organic EL element having excellent luminous efficiency.

Description

Technical Field

[0001] The present invention relates to compounds and elements suitable for self-luminous electronic elements suitable for various display devices, especially organic electroluminescent elements (hereinafter referred to as organic EL elements), and specifically, to amine compounds having a benzoxazole structure, and organic EL elements or electronic devices using the amine compounds. Background Art

[0002] In 1987, CW Tang and others from Eastman Kodak Company developed a stacked structure element that divided the functions among the materials, making the organic EL element using organic materials a practical element. They stacked a phosphor that can transfer electrons and an organic substance that can transfer holes, and injected the charges of both into the phosphor layer to make it emit light, thereby obtaining 1000 cd / m with a voltage of less than 10V. 2 The above high brightness (see Patent Document 1 and Patent Document 2).

[0003] So far, a large number of improvements have been made for the practical application of organic EL elements. In the field-luminescent element in which the various functions of the stacked structure are further subdivided and an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially arranged on a substrate, a light-emitting element with a bottom emission structure that emits light from the bottom has been used to achieve high efficiency and durability (for example, refer to non-patent document 1).

[0004] In recent years, a light-emitting element with a top emission structure that uses a metal with a high work function for the anode and emits light from the top has been used. In a bottom emission structure that extracts light from the bottom with a pixel circuit, the area of ​​the light-emitting portion is limited. In contrast, in a light-emitting element with a top emission structure, light is extracted from the top and the pixel circuit is not blocked, so there is an advantage of expanding the light-emitting portion. In a light-emitting element with a top emission structure, a semi-transparent electrode such as LiF / Al / Ag (for example, see non-patent document 2), Ca / Mg (for example, see non-patent document 3), LiF / MgAg, etc. is used as the cathode.

[0005] In such a light-emitting element, when the light emitted from the light-emitting layer is incident on other films, if the incident angle is above a certain angle, total reflection occurs at the interface between the light-emitting layer and the other films. Therefore, only a part of the emitted light can be used. In recent years, in order to improve the light extraction efficiency, a light-emitting element having a "capping layer" with a high refractive index arranged outside a semi-transparent electrode with a low refractive index has been proposed (for example, refer to non-patent documents 2 and 3).

[0006] Regarding the effect of the capping layer in the top emission structure light emitting element, when Ir(ppy) 3In the light-emitting element used for the light-emitting material, the current efficiency was 38 cd / A without a capping layer, while in the light-emitting element using ZnSe with a film thickness of 60 nm as a capping layer, it was 64 cd / A, confirming an efficiency improvement of about 1.7 times. In addition, it is shown that the maximum point of the transmittance of the semi-transparent electrode and the capping layer is not necessarily consistent with the maximum point of the efficiency, indicating that the maximum point of the light extraction efficiency is determined by the interference effect (for example, refer to non-patent document 3).

[0007] In the past, it was proposed to use a high-precision metal mask in the formation of the capping layer, but when used under high temperature conditions, the metal mask is deformed due to heat, which has the problem of reduced positioning accuracy. Therefore, in the case of ZnSe, the melting point is as high as 1100°C or more (for example, refer to non-patent document 3), and it is impossible to evaporate at the correct position in the high-precision metal mask, which may also affect the light-emitting element itself. Furthermore, even if the film is formed by sputtering, it will affect the light-emitting element, so the capping layer with inorganic substances as the constituent material is not suitable for use.

[0008] In addition, as a capping layer for adjusting the refractive index, tris(8-hydroxyquinoline)aluminum (hereinafter referred to as Alq 3 ) (see, for example, Non-Patent Document 2), it is known that Alq 3 Organic EL materials generally used as green light-emitting materials or electron transport materials have weak absorption near 450nm for cyan light-emitting materials, so in the case of cyan light-emitting elements, there are problems of reduced color purity and reduced light extraction efficiency.

[0009] Furthermore, in the device manufactured using the conventional cover layer, sunlight with a wavelength of 400 nm to 410 nm passes through, affecting the materials inside the device, and there is also the problem of reduced color purity and reduced light extraction efficiency.

[0010] In order to improve the device characteristics of the organic EL element and to significantly improve the light extraction efficiency, the material of the capping layer needs to have a high refractive index, a low extinction coefficient, and excellent thin film stability and durability.

[0011] Prior art literature

[0012] Patent Literature

[0013] Patent Document 1: Japanese Patent Application Laid-Open No. 8-048656

[0014] Patent Document 2: Japanese Patent No. 3194657

[0015] Patent Document 3: International Publication No. 2014009310

[0016] Patent Document 4: International Publication No. 2013 / 038627

[0017] Patent Document 5: International Publication No. 2021140896

[0018] Non-patent literature

[0019] Non-patent document 1: Proceedings of the 9th Seminar of the Society of Applied Physics, pp. 55-61 (2001)

[0020] Non-patent document 2: Appl. Phys. Let., 78, 544 (2001)

[0021] Non-patent document 3: Appl. Phys. Let., 82, 466 (2003)

[0022] Non-patent document 4: J. Org. Chem., 71, 1802 (2006)

[0023] Non-patent document 5: Chem. Rev. 2016, 116, 12564

[0024] Non-patent document 6: Tetrahedron, 58, (2002), 9633

[0025] Non-patent document 7: Appl. Phys. Lett., 98, 083302 (2011) Summary of the invention

[0026] Problems to be solved by the invention

[0027] The object of the present invention is to provide an organic EL element having a capping layer in order to improve the element characteristics of an organic EL element and to significantly improve the light extraction efficiency, wherein the capping layer is composed of a material having (1) a high refractive index, (2) good thin film stability, (3) excellent durability, (4) excellent light resistance, and (5) no absorption in the respective wavelength regions of cyan, green and red.

[0028] Examples of physical properties of materials suitable for the capping layer of the present invention include (1) high refractive index, (2) vapor deposition, (3) stable thin film state, and (4) high glass transition temperature. In addition, examples of physical properties of elements suitable for the present invention include (1) high light extraction efficiency, (2) reduction in colorless purity, (3) light transmission without time-dependent changes, and (4) long life.

[0029] Means for solving problems

[0030] Therefore, in order to achieve the above-mentioned purpose, the present inventors focused on the excellent stability and durability of the thin film of the arylamine material, prepared a selective amine compound with a specific benzoxazole structure having a high refractive index at a concentration of 10 -5 The present invention was accomplished as a result of intensive evaluation of the characteristics of an organic EL element using a material having a high absorbance at a wavelength of 400 nm to 410 nm in an absorption spectrum of 1.5 mol / L as a material constituting a capping layer.

[0031] That is, according to the present invention, there are provided an amine compound represented by the following general formula (A), and an organic EL device or an electronic device thereof.

[0032] 1) An amine compound represented by the following general formula (A).

[0033] [Chemistry 1]

[0034]

[0035] In the formula, Ar 1 represents a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, Ar 2 ,Ar 3 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, L 1 ~L 3 They may be the same as or different from each other, and represent a single bond, a divalent group obtained by removing two hydrogen atoms from unsubstituted benzene, a divalent group obtained by removing two hydrogen atoms from unsubstituted biphenyl, or a divalent group obtained by removing two hydrogen atoms from unsubstituted naphthalene, and X represents an oxygen atom or a sulfur atom.

[0036] 2) The amine compound according to 1) above, which is represented by the following general formula (B) or (C),

[0037] [Chemistry 2]

[0038]

[0039] [Chemistry 3]

[0040]

[0041] In the above general formula (B) or (C), Ar 1 ~Ar 3 , L 1 ~L 3 and X has the same meaning as in the above general formula (A).

[0042] 3) The amine compound according to 2) above, wherein L in the general formula (A), (B) or (C) is 1 ~L 3 It is a single bond, unsubstituted 1,4-phenylene, unsubstituted 4,4'-biphenylene, unsubstituted 2,6-naphthylene, or unsubstituted 2,7-naphthylene.

[0043] 4) The amine compound according to 3) above, wherein Ar in the general formula (A), (B) or (C) is 3 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted furyl or substituted or unsubstituted thienyl.

[0044] 5) The amine compound according to 4) above, wherein Ar in the general formula (A), (B) or (C) 3 is unsubstituted phenyl, unsubstituted biphenyl, unsubstituted naphthyl, unsubstituted furyl or unsubstituted thienyl.

[0045] 6) The amine compound according to 3) above, wherein Ar in the general formula (A), (B) or (C) 1 is substituted or unsubstituted 2-benzoxazolyl, substituted or unsubstituted 2-benzothiazolyl, substituted or unsubstituted 2-benzofuranyl, substituted or unsubstituted 2-benzothiophenyl, substituted or unsubstituted 2-dibenzofuranyl, substituted or unsubstituted 2-dibenzothiophenyl, substituted or unsubstituted 3-dibenzofuranyl, or substituted or unsubstituted 3-dibenzothiophenyl.

[0046] 7) The amine compound according to 6) above, wherein Ar in the general formula (A), (B) or (C) is 1 It is unsubstituted 2-benzoxazolyl, unsubstituted 2-benzothiazolyl, unsubstituted 2-benzofuranyl, unsubstituted 2-benzothiophenyl, unsubstituted 2-dibenzofuranyl, unsubstituted 2-dibenzothiophenyl, unsubstituted 3-dibenzofuranyl or unsubstituted 3-dibenzothiophenyl.

[0047] 8) The amine compound according to 7) above, wherein in the general formula (A), (B) or (C), Ar 3 is unsubstituted phenyl, unsubstituted biphenyl, unsubstituted naphthyl, unsubstituted furyl, or unsubstituted thienyl.

[0048] 9) An organic EL element comprising at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode and a capping layer in this order, wherein the capping layer contains the amine compound described in 1) or 2) above.

[0049] 10) The organic EL element according to 9) above, characterized in that the capping layer has an extinction coefficient of 0.2 or more in the wavelength range of 400 nm to 410 nm and a concentration of 10 -5 The absorbance in the absorption spectrum of mol / L is 0.2 or more in the wavelength range of 400 nm to 410 nm.

[0050] 11) The organic EL element according to 9) above, wherein the refractive index of the capping layer is 1.85 or more within a wavelength range of 450 nm to 750 nm of light passing through the capping layer.

[0051] 12) An organic EL element, which is an organic EL element having at least an anode electrode, a hole transport layer, a light-emitting layer, an electron transport layer, a cathode electrode and a capping layer in sequence, wherein the capping layer is a stacked layer or a mixed layer composed of two or more compounds, at least one of which is the amine compound described in 1) or 2) above.

[0052] 13) An electronic device or electronic component comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer contains the amine compound described in 1) or 2) above.

[0053] Effects of the Invention

[0054] The amine compound of the present invention has the following characteristics: (1) high extinction coefficient, (2) high refractive index in the wavelength range of 450 nm to 750 nm, (3) vapor deposition, (4) stable thin film state, and (5) high heat resistance. It can be used as a capping layer provided outside the transparent or semi-transparent electrode of an organic EL element and having a higher refractive index than the semi-transparent electrode, thereby greatly improving the light extraction efficiency. An organic EL element can be obtained in which the material inside the element is prevented from deteriorating. BRIEF DESCRIPTION OF THE DRAWINGS

[0055] Figure 1 It is a figure which shows the structural formula of the compound 1 to 12 as an example of the amine compound of this invention.

[0056] Figure 2 It is a figure which shows the structural formula of the compound 13 - 24 as an example of the amine compound of this invention.

[0057] Figure 3It is a figure which shows the structural formula of Compounds 25 to 36 as examples of the amine compound of the present invention.

[0058] Figure 4 It is a figure which shows the structural formula of the compound 37 to 48 as an example of the amine compound of the present invention.

[0059] Figure 5 It is a figure which shows the structural formula of Compounds 49 to 60 as examples of the amine compound of the present invention.

[0060] Figure 6 It is a diagram showing the structural formulas of Compounds 61 to 69 as examples of the amine compound of the present invention.

[0061] Figure 7 It is a figure which shows the structural formula of Compounds 70 to 79 as examples of the amine compound of the present invention.

[0062] Figure 8 It is a figure which shows the structural formula of Compounds 80 to 92 as examples of the amine compound of the present invention.

[0063] Fig. 9 It is a figure which shows the structural formula of Compounds 93 to 104 as examples of the amine compound of the present invention.

[0064] Fig.10 It is a diagram showing the structural formulas of Compounds 105 to 116 as examples of the amine compound of the present invention.

[0065] Fig.11 It is a diagram showing the structural formulas of Compounds 117 to 128 as examples of the amine compound of the present invention.

[0066] Fig.12 It is a diagram showing the structural formulas of Compounds 129 to 136 as examples of the amine compound of the present invention.

[0067] Fig.13 It is a diagram showing the structural formulas of Compounds 137 to 144 as examples of the amine compound of the present invention.

[0068] Fig.14 It is a diagram showing the structural formulas of Compounds 145 to 152 as examples of the amine compound of the present invention.

[0069] Fig.15 It is a diagram showing the structural formulas of Compounds 153 to 160 as examples of the amine compound of the present invention.

[0070] Fig.16 It is a diagram showing the structural formulas of Compounds 161 to 168 as examples of the amine compound of the present invention.

[0071] Fig.17 It is a diagram showing the structural formulas of Compounds 169 to 178 as examples of the amine compound of the present invention.

[0072] Fig.18 It is a diagram showing the structural formulas of Compounds 179 to 188 as examples of the amine compound of the present invention.

[0073] Fig.19 It is a figure which shows the structural formula of the compound 189-200 as an example of the amine compound of this invention.

[0074] Fig. 20 This is a diagram showing the structural formulas of Compounds 201 to 208 as examples of the amine compound of the present invention.

[0075] Fig.21 This is a diagram showing an example of the structure of the organic EL element of the present invention. DETAILED DESCRIPTION

[0076] The amine compound of the present invention is a novel compound represented by the general formula (A), (B) or (C), and the benzoxazole derivatives serving as the main skeleton of these compounds can be synthesized by a known method per se (see, for example, Non-Patent Document 4).

[0077] Furthermore, the amine compound of the present invention can be synthesized by subjecting the synthesized halogenated benzoxazole derivative to a coupling reaction with an arylamine using a copper catalyst, a palladium catalyst, etc. In addition, the amine compound of the present invention can be synthesized similarly by subjecting the halogenated benzoxazole derivative to a borate ester derivative and then subjecting it to a coupling reaction with a halogenated arylamine (for example, see Non-Patent Documents 5 and 6).

[0078] In the amine compounds of the present invention, Ar in the general formula (A), (B) or (C) 2 ,Ar 3 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.

[0079] In the amine compound of the present invention, Ar in the general formula (A), (B) or (C) 2 ,Ar 3The “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” specifically refers to phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, spirobifluorenyl, indenyl, pyrenyl, peryl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyridyl, pyrimidinyl, triphenylene radical, pyrimidinyl ... In addition to the oxazine group, furanyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, imidazopyridyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group and carbolyl group, there can be mentioned an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms.

[0080] In the amine compound of the present invention, Ar in the general formula (A), (B) or (C) 2 ,Ar 3 The "substituent" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" specifically includes, except for a deuterium atom; a cyano group, a nitro group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom; a silyl group such as a trimethylsilyl group, a triphenylsilyl group; a straight-chain or branched alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group; a straight-chain or branched alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group; an alkenyl group such as a vinyl group, an allyl group; an aryloxy group such as a phenoxy group, a tolyloxy group; an arylalkoxy group such as a benzyloxy group, a phenethoxy group; a phenyl group, a biphenyl group, a triphenyl group In addition to aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, spirobifluorenyl, indenyl, pyrenyl, peryl, fluoranthenyl, and benzo[9,10]phenanthrenyl; pyridyl, thienyl, furanyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, and carbolyl, aryl groups having 6 to 30 carbon atoms or heteroaryl groups having 2 to 20 carbon atoms can be listed. These substituents may be further substituted with the substituents exemplified above. Furthermore, these substituents and the substituted benzene ring or a plurality of substituents substituted on the same benzene ring may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

[0081] In the amine compound of the present invention, Ar in the above general formula (A), (B) or (C) 2It is preferably an unsubstituted aromatic hydrocarbon group or an unsubstituted aromatic heterocyclic group, and more preferably an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted benzoxazolyl group, an unsubstituted benzothiazolyl group, an unsubstituted benzofuranyl group, an unsubstituted benzothiophenyl group, an unsubstituted phenanthrenyl group, or an unsubstituted quinolyl group.

[0082] In the amine compound of the present invention, Ar in the above general formula (A), (B) or (C) 3 Preferably it is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted furyl or a substituted or unsubstituted thienyl, more preferably it is an unsubstituted phenyl, an unsubstituted biphenyl, an unsubstituted naphthyl, an unsubstituted furyl or an unsubstituted thienyl, further preferably it is an unsubstituted phenyl or an unsubstituted naphthyl, further preferably it is an unsubstituted phenyl or an unsubstituted 2-naphthyl.

[0083] In the amine compounds of the present invention, Ar in the general formula (A), (B) or (C) 1 represents a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0084] Preferably, Ar 1 It is represented by a substituted or unsubstituted 2-benzoxazolyl group, a substituted or unsubstituted 2-benzothiazolyl group, a substituted or unsubstituted 2-benzofuranyl group, a substituted or unsubstituted 2-benzothiophenyl group, a substituted or unsubstituted 2-dibenzofuranyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, a substituted or unsubstituted 3-dibenzofuranyl group, or a substituted or unsubstituted 3-dibenzothiophenyl group.

[0085] More preferably, Ar 1 It is represented by unsubstituted 2-benzoxazolyl, unsubstituted 2-benzothiazolyl, unsubstituted 2-benzofuranyl, unsubstituted 2-benzothiophenyl, unsubstituted 2-dibenzofuranyl, unsubstituted 2-dibenzothiophenyl, unsubstituted 3-dibenzofuranyl or unsubstituted 3-dibenzothiophenyl.

[0086] In the amine compound of the present invention, Ar in the general formula (A), (B) or (C) 1 The "substituent" in the "substituted benzoxazolyl", "substituted benzothiazolyl", "substituted benzofuranyl", "substituted benzothiophenyl", "substituted dibenzofuranyl" or "substituted dibenzothiophenyl" represented by the general formula (A) can be exemplified by the same substituents as those for Ar in the general formula (A). 2 ,Ar3 The "substituent" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" is the same group, and the same forms can be taken.

[0087] In the amine compound of the present invention, L in the above general formula (A), (B) or (C) 1 ~L 3 may be the same as or different from each other, and represent a single bond, a divalent group obtained by removing two hydrogen atoms from unsubstituted benzene, a divalent group obtained by removing two hydrogen atoms from unsubstituted biphenyl, or a divalent group obtained by removing two hydrogen atoms from unsubstituted naphthalene, and are preferably a single bond, unsubstituted 1,4-phenylene, unsubstituted 4,4'-biphenylene, unsubstituted 2,6-naphthylene, or unsubstituted 2,7-naphthylene. In particular, L 3 It is preferably an unsubstituted 1,4-phenylene group or an unsubstituted 4,4'-biphenylene group, and more preferably an unsubstituted 1,4-phenylene group.

[0088] In the amine compound of the present invention, X in the above general formula (A), (B) or (C) represents an oxygen atom or a sulfur atom.

[0089] The amine compound of the present invention is suitable for use in organic EL devices, electronic devices, or electronic components.

[0090] The electronic device or electronic component is, for example, a television, a mobile phone, a car navigation system, a digital camera or other electronic device, or an electronic component such as a semiconductor element, and has a pair of electrodes and at least one organic layer sandwiched therebetween. The amine compound of the present invention is contained in the organic layer.

[0091] Among the amine compounds of the present invention which are suitable for the organic EL device, electronic device and electronic component of the present invention, specific examples of preferred compounds are shown below. Figures 1 to 20 , but are not limited to these compounds.

[0092] There is no particular limitation on the purification of the amine compound of the present invention. It can be purified by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization purification using a solvent, crystallization purification, sublimation purification, etc., and the compound is identified by NMR analysis. As physical property values, the melting point, glass transition temperature (Tg) and refractive index are measured. The melting point becomes an index of vapor deposition, the glass transition temperature (Tg) becomes an index of the stability of the thin film state, and the refractive index becomes an index related to the improvement of light extraction efficiency.

[0093] The melting point and the glass transition temperature (Tg) were measured using a powder with a high-sensitivity differential scanning calorimeter (DSC3100SA manufactured by Bruker-AXS).

[0094] The refractive index and the extinction coefficient can be measured by forming a thin film of 80 nm on a silicon substrate and using a spectrophotometer (F10-RT-UV manufactured by Filmecics).

[0095] Regarding the absorbance at wavelengths of 400 nm and 410 nm, the compound of the present invention was used and the concentration was adjusted to 10 with toluene solvent. -5 mol / L, in terms of absorption coefficient, a toluene solution was used and the concentration was adjusted to 5.0×10 -6 mol / L、1.0×10 - 5 mol / L、1.5×10 -5 mol / L、2.0×10 -5 The absorption coefficient was calculated from the calibration curve obtained by measuring four concentrations of 1 mol / L using an ultraviolet-visible-near-infrared spectrophotometer (V-650 manufactured by JASCO Corporation).

[0096] As the structure of the organic EL element of the present invention, for example, in the case of a light-emitting element of a top emission structure, a structure consisting of an anode, a hole transport layer, a light-emitting layer, an electron transport layer, a cathode and a capping layer in sequence on a glass substrate can be listed, and in addition, a structure having a hole injection layer between the anode and the hole transport layer, a structure having an electron blocking layer between the hole transport layer and the light-emitting layer, a structure having a hole blocking layer between the light-emitting layer and the electron transport layer, and a structure having an electron injection layer between the electron transport layer and the cathode can be listed. In these multilayer structures, it is possible to omit or concurrently serve as one or some organic layers, for example, it is possible to make a structure that concurrently serves as a hole injection layer and a hole transport layer, a structure that concurrently serves as a hole transport layer and an electron blocking layer, a structure that concurrently serves as a hole blocking layer and an electron transport layer, a structure that concurrently serves as an electron transport layer and an electron injection layer, etc. In addition, it is also possible to make a structure in which two or more organic layers having the same function are stacked, a structure in which two hole transport layers are stacked, a structure in which two light-emitting layers are stacked, a structure in which two electron transport layers are stacked, a structure in which two capping layers are stacked, etc.

[0097] The total thickness of each layer of the organic EL element is preferably about 200nm to 750nm, more preferably about 350nm to 600nm. In addition, the thickness of the capping layer is preferably, for example, 30nm to 120nm, more preferably 40nm to 80nm. In this case, a good light extraction efficiency is obtained. It should be noted that the thickness of the capping layer can be appropriately changed according to the type of light-emitting material used in the light-emitting element, the thickness of the organic EL element other than the capping layer, etc.

[0098] As the anode of the organic EL element of the present invention, an electrode material having a large work function such as ITO or gold is used.

[0099] As the hole injection layer of the organic EL element of the present invention, an arylamine compound having a structure in which three or more triphenylamine structures are connected by a single bond or a divalent group containing no heteroatoms in the molecule can be used, such as a starburst-type triphenylamine derivative, various triphenylamine tetramers and other materials, porphyrin compounds represented by copper phthalocyanine, acceptor heterocyclic compounds such as hexacyanoazabenzo[9,10]phenanthrene, and coating-type polymer materials. These can be formed into a film alone, or can be used as a single layer mixed with other materials to form a film, or can be used as a stacked structure between layers formed by a single film, between layers formed by a mixed film, or between layers formed by a single film and layers formed by a mixed film. For these materials, in addition to the vapor deposition method, thin film formation can also be performed by a known method such as a spin coating method and an inkjet method.

[0100] As the hole transport layer of the organic EL element of the present invention, it is preferred to use benzidine derivatives such as N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (hereinafter referred to as TPD), N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine, N,N,N',N'-tetra(biphenyl)benzidine; 1,1-bis[4-(di-4-tolylamino)phenyl]cyclohexane, and especially arylamine compounds having a structure in which two triphenylamine structures are connected by a single bond or a divalent group not containing a hetero atom in the molecule, such as N,N,N',N'-tetraphenylbenzidine, etc. In addition, it is preferred to use arylamine compounds having a structure in which three or more triphenylamine structures are connected by a single bond or a divalent group not containing a hetero atom in the molecule, such as various triphenylamine trimers and tetramers, etc. These can be formed into films alone, or used as a single layer mixed with other materials to form films, or as a laminated structure between layers formed alone, between layers formed by mixing, or between layers formed alone and layers formed by mixing. In addition, as a hole injection-transport layer, a coating-type polymer material such as poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) can be used. For these materials, in addition to the vapor deposition method, thin film formation can also be performed by known methods such as spin coating and inkjet method.

[0101] In addition, in the hole injection layer or the hole transport layer, products obtained by further P-doping tri(bromophenyl)amine antimony hexachloride, axialene derivatives (for example, see Patent Document 3), etc., or polymer compounds having the structure of a benzidine derivative in a partial structure such as TPD can be used for the materials commonly used in this layer.

[0102] As the electron blocking layer of the organic EL element of the present invention, carbazole derivatives such as 4,4',4"-tri(N-carbazyl)triphenylamine (hereinafter referred to as TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (hereinafter referred to as mCP), and 2,2-bis(4-carbazol-9-yl-phenyl)adamantane can be used; 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl] Compounds with electron blocking effect such as compounds having triphenylsilyl and triarylamine structures represented by [1,2-diphenyl]-9H-fluorene. These can be formed into a film alone, or used as a single layer mixed with other materials to form a film, or as a stacked structure between layers formed into a film alone, between layers formed into a film mixed, or between layers formed into a film alone and layers formed into a film mixed. For these materials, in addition to the evaporation method, thin films can also be formed by known methods such as spin coating and inkjet.

[0103] As the light-emitting layer of the organic EL element of the present invention, in addition to Alq 3 In addition to the metal complex of quinolinephenol derivatives headed by, various metal complexes, anthracene derivatives, bis-styrylbenzene derivatives, pyrene derivatives, oxazole derivatives, poly-p-phenylene vinylene derivatives, etc. can also be used. In addition, the light-emitting layer can be composed of a host material and a dopant material. As the host material, an anthracene derivative is preferably used. In addition, in addition to the above-mentioned light-emitting materials, a heterocyclic compound having an indole ring as a partial structure of the condensed ring, a heterocyclic compound having a carbazole ring as a partial structure of the condensed ring, a carbazole derivative, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, etc. can also be used. In addition, as a dopant material, quinacridone, coumarin, rubrene, perylene and their derivatives, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, etc. can be used. These can be formed into a film alone, or used as a single layer mixed with other materials to form a film, or as a laminated structure between layers formed into a film alone, between layers formed into a film mixed, or between layers formed into a film alone and layers formed into a film mixed.

[0104] In addition, as the luminescent material, a phosphorescent light emitting body can also be used. As the phosphorescent light emitting body, a phosphorescent light emitting body of a metal complex such as iridium or platinum can be used. For example, Ir(ppy) can be used. 3Green phosphorescent materials, FIrpic, FIr6 and other cyan phosphorescent materials, Btp 2 Red phosphorescent light emitters such as Ir(acac) can be used as the main material at this time. As the main material of hole injection-transport, carbazole derivatives such as 4,4'-di(N-carbazolyl)biphenyl, TCTA, and mCP can be used. As the main material of electron transport, p-bis(triphenylsilyl)benzene, 2,2',2"-(1,3,5-phenylene)-tri(1-phenyl-1H-benzimidazole) can be used, and high-performance organic EL elements can be produced.

[0105] In order to avoid concentration quenching, the phosphorescent light-emitting material is preferably doped into the host material in a range of 1 to 30 wt % based on the entire light-emitting layer by co-evaporation.

[0106] In addition, as the luminescent material, materials emitting delayed fluorescence such as CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN can also be used (for example, see Non-Patent Document 7). These materials can be formed into thin films by known methods such as spin coating and inkjet in addition to the vapor deposition method.

[0107] As the hole blocking layer of the organic EL element of the present invention, it is possible to use metal complexes of quinoline phenol derivatives such as bathocuproine, bis(2-methyl-8-hydroxyquinoline)-4-phenylphenol aluminum (III) (hereinafter referred to as BAlq), various rare earth complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, benzoxazole derivatives and other compounds with hole blocking effects. These materials can also serve as materials for electron transport layers. These can be formed into films alone, or used as a single layer mixed with other materials to form a film, or as a laminated structure between layers formed alone, between layers formed by mixing, or between layers formed alone and layers formed by mixing. For these materials, in addition to the evaporation method, thin film formation can also be performed by known methods such as spin coating and inkjet.

[0108] As the electron transport layer of the organic EL element of the present invention, in addition to Alq 3In addition to the metal complex of quinoline phenol derivatives headed by BAlq, various metal complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, pyridine derivatives, benzimidazole derivatives, benzoxazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, thiole derivatives, etc. can also be used. These can be film-formed alone, or used as a single layer mixed with other materials to form a film, or as a laminated structure between layers formed alone, between layers formed by mixing, or between layers formed alone and layers formed by mixing. For these materials, in addition to the evaporation method, thin film formation can also be carried out by known methods such as spin coating and inkjet.

[0109] As the electron injection layer of the organic EL element of the present invention, alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinolinephenol derivatives such as lithium quinolinephenol, metal oxides such as aluminum oxide, or metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs) can be used. In the preferred selection of the electron transport layer and the cathode, they can be omitted.

[0110] Furthermore, in the electron injection layer or the electron transport layer, a material generally used in the layer and further N-doped with a metal such as cesium can be used.

[0111] As the cathode of the organic EL element of the present invention, electrode materials with low work function such as aluminum, alloys with lower work function such as magnesium-silver alloy, magnesium-calcium alloy, magnesium-indium alloy, aluminum-magnesium alloy, ITO, IZO, etc. are used as electrode materials.

[0112] As the capping layer of the organic EL element of the present invention, an amine compound represented by the above general formula (A), (B) or (C) is used. These can be formed into a film alone, or can be used as a single layer mixed with other materials to form a film, or can be used as a laminated structure between layers formed into a film alone, between layers formed into a film by mixing, or between layers formed into a film alone and layers formed into a film by mixing. For these materials, in addition to the evaporation method, thin film formation can also be performed by known methods such as spin coating and inkjet method.

[0113] It should be noted that, in the above description, an organic EL element with a top emission structure is described, but the present invention is not limited thereto, and is also applicable to an organic EL element with a bottom emission structure and an organic EL element with a dual emission structure that emits light from both the top and the bottom. In these cases, the electrode in the direction in which light is taken out from the light-emitting element to the outside needs to be transparent or translucent.

[0114] The refractive index of the material constituting the capping layer is preferably greater than the refractive index of the adjacent electrode. That is, the efficiency of light extraction in the organic EL element is improved by the capping layer. As for its effect, when the reflectivity at the interface of the capping layer and the material connected to the capping layer is large, the effect of light interference is large, so it is effective. Therefore, the refractive index of the material constituting the capping layer is preferably greater than the refractive index of the adjacent electrode.

[0115] In the organic EL element of the present invention, the refractive index of light passing through the capping layer within the wavelength range of 450 nm to 750 nm may be 1.70 or more, more preferably 1.80 or more, particularly preferably 1.85 or more, and even more preferably 1.90 or more.

[0116] In the organic EL device of the present invention, the thickness of the capping layer is preferably in the range of 30 nm to 120 nm, and more preferably in the range of 40 nm to 80 nm.

[0117] In the capping layer of the organic EL element of the present invention, the extinction coefficient is 0.2 or more in the wavelength range of 400 nm to 410 nm, and the concentration is 10 -5 The absorbance in the absorption spectrum of mol / L is preferably 0.2 or more in the wavelength range of 400 nm to 410 nm.

[0118] In the organic EL element of the present invention, the capping layer can be prepared by laminating or mixing two or more different constituent materials. It is noted that at least one of the constituent materials is the amine compound of the present invention. The refractive index, extinction coefficient and absorbance of the capping layer are preferably within the above-mentioned numerical ranges.

[0119] Hereinafter, the embodiments of the present invention will be specifically described by way of examples, but the present invention is not limited to the following examples unless the scope of the invention exceeds the scope of the invention.

[0120] Example 1

[0121] <Synthesis of N-(4-benzofuran-2-yl-phenyl)-N-(4-dibenzofuran-3-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 40)>

[0122] In a nitrogen-purged reaction vessel, N-(4-benzofuran-2-yl-phenyl)-N-(4-dibenzofuran-3-yl-phenyl)-amine: 10.0 g, 6-(4-chloro-phenyl)-2-phenyl-benzoxazole: 7.4 g, tris(dibenzylideneacetone)dipalladium(0): 0.4 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 3.2 g were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was recrystallized and purified using chlorobenzene solvent to obtain 8.6 g (yield: 53.9%) of yellow powder of N-(4-benzofuran-2-yl-phenyl)-N-(4-dibenzofuran-3-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 40).

[0123] [Chemistry 4]

[0124]

[0125] The structure of the obtained yellow powder was identified using NMR.

[0126] use 1 H-NMR (CDCl 3 ) The following 32 hydrogen signals were detected.

[0127] δ(ppm)=8.29(1H), 8.28(1H), 7.99(1H), 7.96(1H), 7.80(5H), 7.68-7.57(8H) ,7.57-7.49(4H), 7.46(1H), 7.36(1H), 7.38-7.26(6H), 7.23(2H), 6.95(1H).

[0128] Example 2

[0129] <Synthesis of N,N-bis(4-benzofuran-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 50)>

[0130] In a nitrogen-purged reaction vessel, 4-(2-phenyl-benzoxazol-6-yl)-phenyl-amine: 8.7 g, 2-(4-bromo-phenyl)-benzofuran: 17.4 g, tris(dibenzylideneacetone)dipalladium(0): 0.6 g, tri-tert-butylphosphine: 0.3 g, sodium tert-butoxide: 4.4 g were placed, and refluxed with stirring overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was recrystallized and purified using chlorobenzene solvent to obtain a yellow powder of N,N-bis(4-benzofuran-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 50): 14.3 g (yield: 70.1%).

[0131] [Chemistry 5]

[0132]

[0133] The structure of the obtained yellow powder was identified using NMR.

[0134] use 1 H-NMR (CDCl 3 ) The following 30 hydrogen signals were detected.

[0135] δ(ppm)=8.28(2H), 7.80(6H), 7.65-7.54(8H), 7.52(2H), 7.31-7.20(10H), 6.96(2H).

[0136] Example 3

[0137] <Synthesis of N-(4-benzooxazol-2-yl-phenyl)-N-(4-benzothiazol-2-yl-phenyl)-N-{4-(2-naphth-2-yl-benzooxazol-6-yl)-phenyl}-amine (Compound 69)>

[0138] In a nitrogen-purged reaction vessel, N-(4-benzoxazol-2-yl-phenyl)-N-(4-benzothiazol-2-yl-phenyl)-amine: 7.0 g, 6-(4-chloro-phenyl)-2-naphth-2-yl-benzoxazole: 6.5 g, tris(dibenzylideneacetone)dipalladium(0): 0.3 g, tri-tert-butylphosphine: 0.1 g, sodium tert-butoxide: 2.4 g were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain 3.6 g (yield: 28.9%) of yellow powder of N-(4-benzoxazol-2-yl-phenyl)-N-(4-benzothiazol-2-yl-phenyl)-N-{4-(2-naphthalen-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 69).

[0139] [Chemistry 6]

[0140]

[0141] The structure of the obtained yellow powder was identified using NMR.

[0142] use 1 H-NMR (CDCl 3 ) The following 30 hydrogen signals were detected.

[0143] δ(ppm)=8.80(1H), 8.34(1H), 8.18(2H), 8.05(3H), 8.00(2H), 7.90(2H), 7.8 6(1H), 7.85(1H), 7.76(1H), 7.65(3H), 7.58(3H), 7.49(1H), 7.41-7.27(9H).

[0144] Example 4

[0145] <Synthesis of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzooxazol-2-yl-phenyl)-N-{4-(2-naphth-2-yl-benzooxazol-6-yl)-phenyl}-amine (Compound 70)>

[0146] In a nitrogen-purged reaction vessel, 6.4 g of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzoxazol-2-yl-phenyl)-amine, 6.2 g of 6-(4-chloro-phenyl)-2-naphth-2-yl-benzoxazole, 0.3 g of tris(dibenzylideneacetone)dipalladium(0), 0.1 g of tri-tert-butylphosphine, and 2.3 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain 4.3 g (yield: 37.3%) of a yellow powder of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzoxazol-2-yl-phenyl)-N-{4-(2-naphthalen-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 70).

[0147] [Chemistry 7]

[0148]

[0149] The structure of the obtained yellow powder was identified using NMR.

[0150] use 1 H-NMR (CDCl 3 ) The following 31 hydrogen signals were detected.

[0151] δ(ppm)=8.81(1H), 8.34(1H), 8.16(2H), 8.01(1H), 7.99(1H), 7.91(1H), 7.84(4H) ,7.75(1H),7.64(3H),7.58(4H),7.52(1H),7.32-7.26(9H),7.24(1H),6.98(1H).

[0152] Example 5

[0153] <Synthesis of N,N-bis(4-benzofuran-2-yl-phenyl)-N-{4-(2-naphth-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 78)>

[0154] In a nitrogen-purged reaction vessel, 4-(2-naphthyl-2-yl-benzoxazol-6-yl)-phenyl-amine: 5.7 g, 2-(4-bromo-phenyl)-benzofuran: 10.2 g, tri(dibenzylideneacetone)dipalladium(0): 0.6 g, tri-tert-butylphosphine: 0.3 g, sodium tert-butoxide: 4.9 g were placed, and refluxed with stirring overnight in toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was recrystallized and purified using chlorobenzene solvent to obtain 8.9 g (yield: 72.9%) of yellow powder of N,N-bis(4-benzofuran-2-yl-phenyl)-N-{4-(2-naphthyl-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 78).

[0155] [Chemistry 8]

[0156]

[0157] The structure of the obtained yellow powder was identified using NMR.

[0158] use 1 H-NMR (CDCl 3 ) The following 32 hydrogen signals were detected.

[0159] δ(ppm)=8.80(1H), 8.34(1H), 8.00(1H), 7.99(1H), 7.90(1H), 7.81(6H), 7.66-7.54(7H), 7.51(2H), 7.32-7.20(10H), 6.95(2H).

[0160] Example 6

[0161] <Synthesis of N,N-bis(4-benzofuran-2-yl-phenyl)-N-{4-(2-phenyl-benzothiazol-6-yl)-phenyl}-amine (Compound 119)>

[0162] In a nitrogen-substituted reaction vessel, 4-(2-phenyl-benzothiazol-6-yl)-phenyl-amine: 4.2 g, 2-(4-bromo-phenyl)-benzofuran: 8.0 g, tri(dibenzylideneacetone)dipalladium(0): 0.5 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 4.0 g were placed, and refluxed with stirring overnight in toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by recrystallization using toluene solvent to obtain a yellow powder of N,N-bis(4-benzofuran-2-yl-phenyl)-N-{4-(2-phenyl-benzothiazol-6-yl)-phenyl}-amine (Compound 119): 7.6 g (yield: 79.7%).

[0163] [Chemistry 9]

[0164]

[0165] The structure of the obtained yellow powder was identified using NMR.

[0166] use 1 H-NMR (CDCl 3 ) The following 30 hydrogen signals were detected.

[0167] δ(ppm)=8.12(4H), 7.79(4H), 7.73(1H), 7.61(2H), 7.57(2H), 7.51(5H), 7.32-7.19(10H), 6.95(2H).

[0168] Example 7

[0169] <Synthesis of N,N-(bis(4-benzofuran-2-yl-phenyl)-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 150)>

[0170] In a nitrogen-purged reaction vessel, 5.0 g of 4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl-amine, 7.9 g of 2-(4-bromo-phenyl)-benzofuran, 0.5 g of tris(dibenzylideneacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 4.0 g of sodium tert-butoxide were placed, and the mixture was refluxed and stirred overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by recrystallization using chlorobenzene solvent to obtain 5.4 g of yellow powder of N,N-bis(4-benzofuran-2-yl-phenyl)-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 150) (yield: 52.6%).

[0171] [Chemistry 10]

[0172]

[0173] The structure of the obtained yellow powder was identified using NMR.

[0174] use 1 H-NMR (CDCl 3 ) The following 34 hydrogen signals were detected.

[0175] δ(ppm)=8.29(2H), 7.84(2H), 7.79(4H), 7.72(4H), 7.66(1H), 7.61(2H), 7.56(5H), 7.52(2H), 7.32-7.20(10H), 6.95(2H).

[0176] Example 8

[0177] <Synthesis of N-(4-benzoxazol-2-yl-phenyl)-N-(4-naphth-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 2)>

[0178] In a nitrogen-purged reaction vessel, 5.8 g of N-(4-benzoxazol-2-yl-phenyl)-N-(4-naphth-2-yl-phenyl)-amine, 4.7 g of 6-(4-chloro-phenyl)-2-phenyl-benzoxazole, 0.3 g of tris(dibenzylideneacetone)dipalladium(0), 0.1 g of tri-tert-butylphosphine, and 2.7 g of sodium tert-butoxide were placed, and the mixture was refluxed and stirred overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain 5.3 g of yellow powder of N-(4-benzoxazol-2-yl-phenyl)-N-(4-naphth-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 2) (yield: 55.8%).

[0179] [Chemistry 11]

[0180]

[0181] The structure of the obtained yellow powder was identified using NMR.

[0182] use 1 H-NMR (CDCl 3 ) The following 31 hydrogen signals were detected.

[0183] δ(ppm)=8.32(2H), 8.18(2H), 8.09(1H), 7.94(2H), 7.90(1H), 7.86(1H), 7.84(1H), 7 .80(1H), 7.78(1H), 7.75(2H), 7.66(3H), 7.62-7.48(6H), 7.40-7.33(6H), 7.31(2H).

[0184] Example 9

[0185] <Synthesis of N,N-bis(4-benzoxazol-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 17)>

[0186] In a nitrogen-substituted reaction vessel, N,N-bis(4-benzoxazol-2-yl-phenyl)-amine: 7.1 g, 6-(4-chloro-phenyl)-2-phenyl-benzoxazole: 5.9 g, tri(dibenzylideneacetone)dipalladium(0): 0.3 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 3.4 g were placed, and refluxed with stirring overnight in toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain a yellow powder of N,N-bis(4-benzoxazol-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 17): 3.1 g (yield: 26.3%).

[0187] [Chemistry 12]

[0188]

[0189] The structure of the obtained yellow powder was identified using NMR.

[0190] use 1 H-NMR (CDCl 3 ) The following 28 hydrogen signals were detected.

[0191] δ(ppm)=8.31(2H), 8.21(4H), 7.85(1H), 7.84(1H), 7.79(2H), 7.68(2H), 7.65(1H), 7.62-7.53(5H), 7.37(4H), 7.33(6H).

[0192] Example 10

[0193] <Synthesis of N-(4-benzothiazol-2-yl-phenyl)-N-(4-benzothiophen-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 38)>

[0194] In a nitrogen-purged reaction vessel, 6.1 g of N-(4-benzothiophene-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine, 3.9 g of 2-(4-bromo-phenyl)-benzothiazole, 0.2 g of tris(dibenzylideneacetone)dipalladium(0), 0.1 g of tri-tert-butylphosphine, and 1.8 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was recrystallized and purified using chlorobenzene solvent to obtain 6.8 g (yield: 78.3%) of golden yellow powder of N-(4-benzothiazol-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 38).

[0195] [Chemistry 13]

[0196]

[0197] The structure of the obtained golden yellow powder was identified using NMR.

[0198] use 1 H-NMR (CDCl 3 ) The following 29 hydrogen signals were detected.

[0199] δ(ppm)=8.31(2H), 8.08(1H), 8.03(2H), 7.91(1H), 7.85(2H), 7.83(1H), 7.80(1H) , 7.70(2H), 7.65(3H), 7.58(3H), 7.54(1H), 7.51(1H), 7.43-7.30(5H), 7.28(4H).

[0200] Embodiment 11

[0201] <Synthesis of N-(4-benzothiophen-2-yl-phenyl)-N-(4-naphth-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 52)>

[0202] In a nitrogen-purged reaction vessel, 10.0 g of N-(4-benzothiophene-2-yl-phenyl)-N-(4-naphthalen-2-yl-phenyl)-amine, 7.9 g of 6-(4-chloro-phenyl)-2-phenyl-benzoxazole, 0.4 g of tris(dibenzylideneacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 4.5 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain 12.1 g (yield: 74.2%) of yellow powder of N-(4-benzothiophene-2-yl-phenyl)-N-(4-naphthalen-2-yl-phenyl)-N-{4-(2-phenyl-benzothiophene-6-yl)-phenyl}-amine (Compound 52).

[0203] [Chemistry 14]

[0204]

[0205] The structure of the obtained light yellow powder was identified using NMR.

[0206] use 1 H-NMR (CDCl 3 ) The following 32 hydrogen signals were detected.

[0207] δ(ppm)=8.55(1H), 8.26(1H), 8.09(1H), 7.94(2H), 7.90(1H), 7.85(2H), 7.80(3H), 7 .72(2H), 7.68(4H), 7.63(2H), 7.52(3H), 7.41(2H), 7.37(1H), 7.34(5H), 7.27(2H).

[0208] Example 12

[0209] <Synthesis of N-(4-benzothiophen-2-yl-phenyl)-N-(4-[1,10]phenanthroline-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 61)>

[0210] In a nitrogen-purged reaction vessel, N-(4-benzothiophene-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine: 12.6 g, 2-(4-bromo-phenyl)-[1,10]phenanthroline: 16.7 g, tris(dibenzylideneacetone)dipalladium(0): 0.9 g, tri-tert-butylphosphine: 0.4 g, sodium tert-butoxide: 9.5 g were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain a brown powder of N-(4-benzothiophene-2-yl-phenyl)-N-(4-[1,10]phenanthroline-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 61): 12.4 g (yield: 64.9%).

[0211] [Chemistry 15]

[0212]

[0213] The structure of the obtained brown powder was identified using NMR.

[0214] use 1 H-NMR (CDCl 3 ) The following 32 hydrogen signals were detected.

[0215] δ(ppm)=9.26(1H), 8.35-8.26(6H), 8.10(1H), 7.85(4H), 7.79(2H), 7.71-7.61(6H), 7.57(3H), 7.53(1H), 7.37(3H), 7.33(3H), 7.28(2H).

[0216] Example 13

[0217] <Synthesis of N,N-bis(4-benzothiophen-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 62)>

[0218] In a nitrogen-purged reaction vessel, N,N-bis(4-benzothiophen-2-yl-phenyl)-amine: 7.6 g, 6-(4-chloro-phenyl)-2-phenyl-benzoxazole: 5.9 g, tri(dibenzylideneacetone)dipalladium(0): 0.3 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 3.4 g were placed, and refluxed with stirring in toluene solvent overnight. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 9.5 g (yield: 77.2%) of yellow powder of N,N-bis(4-benzothiophen-2-yl-phenyl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 62).

[0219] [Chemistry 16]

[0220]

[0221] The structure of the obtained yellow powder was identified using NMR.

[0222] use 1 H-NMR (CDCl 3 ) The following 30 hydrogen signals were detected.

[0223] δ(ppm)=8.31(2H), 7.85(3H), 7.82(1H), 7.79(2H), 7.68(4H), 7.65-7.60(3H), 7.60-7.55(3H), 7.52(2H), 7.35(4H), 7.30(2H), 7.25(4H).

[0224] Embodiment 14

[0225] <Synthesis of N-(4-benzooxazol-2-yl-phenyl)-N-(4-benzothiophen-2-yl-phenyl)-N-{4-(2-naphth-2-yl-benzooxazol-6-yl)-phenyl}-amine (Compound 71)>

[0226] In a nitrogen-purged reaction vessel, N-(4-benzoxazol-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-amine: 10.0 g, 6-(4-chloro-phenyl)-2-naphth-2-yl-benzoxazole: 9.4 g, tris(dibenzylideneacetone)dipalladium(0): 0.4 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 3.4 g were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain a yellow powder of N-(4-benzoxazol-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-N-{4-(2-naphthalene-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 71): 16.5 g (yield: 93.6%).

[0227] [Chemistry 17]

[0228]

[0229] The structure of the obtained yellow powder was identified using NMR.

[0230] use 1 H-NMR (CDCl 3 ) The following 31 hydrogen signals were detected.

[0231] δ(ppm)=8.83(1H), 8.37(1H), 8.19(2H), 8.03(1H), 8.02(1H), 7.93(1H), 7.88(1H), 7. 87(1H), 7.85(1H), 7.79(2H), 7.71(2H), 7.69-7.57(6H), 7.54(1H), 7.41-7.28(10H).

[0232] Embodiment 15

[0233] <Synthesis of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzothiophen-2-yl-phenyl)-N-{4-(2-naphth-2-yl-benzooxazol-6-yl)-phenyl}-amine (Compound 79)>

[0234] In a nitrogen-purged reaction vessel, N-(4-benzofuran-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-amine: 10.0 g, 6-(4-chloro-phenyl)-2-naphth-2-yl-benzoxazole: 9.4 g, tris(dibenzylideneacetone)dipalladium(0): 0.4 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 3.5 g were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was recrystallized and purified using chlorobenzene solvent to obtain a yellow powder of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-N-{4-(2-naphthalen-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 79): 16.1 g (yield: 91.2%).

[0235] [Chemistry 18]

[0236]

[0237] The structure of the obtained yellow powder was identified using NMR.

[0238] use 1 H-NMR (CDCl 3 ) The following 32 hydrogen signals were detected.

[0239] δ(ppm)=8.83(1H), 8.37(1H), 8.04(1H), 8.02(1H), 7.94(1H), 7.88(1H), 7.85(2H), 7. 83(2H), 7.79(1H), 7.71-7.58(8H), 7.55(1H), 7.53(1H), 7.42-7.22(10H), 6.98(1H).

[0240] Example 16

[0241] <Synthesis of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzooxazol-2-yl-phenyl)-N-{4-(2-phenyl-benzothiazol-6-yl)-phenyl}-amine (Compound 101)>

[0242] In a nitrogen-purged reaction vessel, 9.8 g of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzoxazol-2-yl-phenyl)-amine, 8.6 g of 6-(4-chloro-phenyl)-2-phenyl-benzothiazole, 0.5 g of tris(dibenzylideneacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 3.5 g of sodium tert-butoxide were placed, and the mixture was refluxed and stirred overnight in a xylene solvent. After natural cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 3.1 g of yellow powder of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzoxazol-2-yl-phenyl)-N-{4-(2-phenyl-benzothiazol-6-yl)-phenyl}-amine (Compound 101) (yield: 18.5%).

[0243] [Chemistry 19]

[0244]

[0245] The structure of the obtained yellow powder was identified using NMR.

[0246] use 1 H-NMR (CDCl 3 ) The following 29 hydrogen signals were detected.

[0247] δ(ppm)=8.21-8.12(6H), 7.86(2H), 7.78(2H), 7.68(2H), 7.60(2H), 7.54(4H), 7.41-7.23(10H), 7.01(1H).

[0248] Embodiment 17

[0249] <Synthesis of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzooxazol-2-yl-phenyl)-N-{4′-(2-phenyl-benzooxazol-6-yl)-[1,1′]biphenyl-4-yl}-amine (Compound 137)>

[0250] In a nitrogen-purged reaction vessel, N-(4-benzofuran-2-yl-phenyl)-N-(4-benzoxazol-2-yl-phenyl)-amine: 10.0 g, 6-(4'-bromo-[1,1']biphenyl-4-yl)-2-phenyl-benzoxazole: 11.7 g, tris(dibenzylideneacetone)dipalladium(0): 0.5 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 3.6 g were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain a yellow powder of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzoxazol-2-yl-phenyl)-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 137): 14.3 g (yield: 76.4%).

[0251] [Chemistry 20]

[0252]

[0253] The structure of the obtained yellow powder was identified using NMR.

[0254] use 1 H-NMR (CDCl 3 ) The following 34 hydrogen signals were detected.

[0255] δ(ppm)=8.32(2H), 8.18(2H), 7.87(2H), 7.85(2H), 7.80-7.73(5H), 7.69(1H) , 7.67(2H), 7.64-7.53(6H), 7.37(2H), 7.35-7.28(8H), 7.27(1H), 7.01(1H).

[0256] Embodiment 18

[0257] <Synthesis of N-(4-benzooxazol-2-yl-phenyl)-N-(4-benzothiophen-2-yl-phenyl)-N-{4′-(2-phenyl-benzooxazol-6-yl)-[1,1′]biphenyl-4-yl}-amine (Compound 138)>

[0258] In a nitrogen-purged reaction vessel, N-(4-benzoxazol-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-amine: 10.0 g, 6-(4'-bromo-[1,1']biphenyl-4-yl)-2-phenyl-benzoxazole: 11.2 g, tris(dibenzylideneacetone)dipalladium(0): 0.4 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 3.4 g were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain a yellow powder of N-(4-benzoxazol-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 138): 15.6 g (yield: 85.5%).

[0259] [Chemistry 21]

[0260]

[0261] The structure of the obtained yellow powder was identified using NMR.

[0262] use 1 H-NMR (CDCl 3 ) The following 34 hydrogen signals were detected.

[0263] δ(ppm)=8.32(2H), 8.18(2H), 7.90-7.83(3H), 7.82-7.73(6H), 7.70(3H), 7.67(2H), 7.58(4H), 7.54(1H), 7.41-7.25(11H).

[0264] Embodiment 19

[0265] <Synthesis of N,N-(bis(4-benzofuran-2-yl-phenyl)-N-{4'-(2-phenyl-benzothiazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 155)>

[0266] In a nitrogen-purged reaction vessel, 8.0 g of 4'-(2-phenyl-benzothiazol-6-yl)-[1,1']biphenyl-4-yl-amine, 12.7 g of 2-(4-bromo-phenyl)-benzofuran, 0.8 g of tris(dibenzylideneacetone)dipalladium(0), 0.3 g of tri-tert-butylphosphine, and 6.1 g of sodium tert-butoxide were placed, and the mixture was refluxed and stirred overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by recrystallization using chlorobenzene solvent to obtain 10.9 g (yield: 67.3%) of a yellow powder of N,N-(bis(4-benzofuran-2-yl-phenyl)-N-{4'-(2-phenyl-benzothiazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 155) as a yellow powder.

[0267] [Chemistry 22]

[0268]

[0269] The structure of the obtained yellow powder was identified using NMR.

[0270] use 1 H-NMR (CDCl 3 ) The following 34 hydrogen signals were detected.

[0271] δ (ppm)=8.17(3H), 8.14(1H), 7.82(5H), 7.76(4H), 7.64(2H), 7.60(2H), 7.57-7.51(5H), 7.35-7.22(10H), 6.98(2H).

[0272] Embodiment 20

[0273] <Synthesis of N-(4-benzoxazol-2-yl-phenyl)-N-phenyl-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 171)>

[0274] In a nitrogen-purged reaction vessel, N-phenyl-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine: 12.0 g, 2-(4-bromo-phenyl)-benzoxazole: 8.3 g, tris(dibenzylideneacetone)dipalladium(0): 0.5 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 5.3 g were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 9.5 g (yield: 54.9%) of yellow powder of N-(4-benzoxazol-2-yl-phenyl)-N-phenyl-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 171).

[0275] [Chemistry 23]

[0276]

[0277] The structure of the obtained yellow powder was identified using NMR.

[0278] use 1 H-NMR (CDCl 3 ) The following 29 hydrogen signals were detected.

[0279] δ(ppm)=8.32(2H), 8.14(2H), 7.88(1H), 7.86(1H), 7.80-7.71(5H), 7.69(1H), 7.6 4(2H), 7.61-7.55(4H), 7.38(3H), 7.35(1H), 7.31-7.24(4H), 7.22(2H), 7.19(1H).

[0280] Embodiment 21

[0281] <Synthesis of N-(4-benzoxazol-2-yl-phenyl)-N-phenyl-N-{4'-(2-naphth-2-yl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 173)>

[0282] In a nitrogen-purged reaction vessel, N-phenyl-N-{4'-(2-naphthyl-2-yl-benzooxazol-6-yl)-[1,1']biphenyl-4-yl}-amine: 11.0 g, 2-(4-bromo-phenyl)-benzoxazole: 6.8 g, tris(dibenzylideneacetone)dipalladium(0): 0.4 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 4.3 g were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 12.8 g (yield: 83.6%) of yellow powder of N-(4-benzoxazol-2-yl-phenyl)-N-phenyl-N-{4'-(2-naphthalen-2-yl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 173).

[0283] [Chemistry 24]

[0284]

[0285] The structure of the obtained yellow powder was identified using NMR.

[0286] use 1 H-NMR (CDCl 3 ) The following 31 hydrogen signals were detected.

[0287] δ(ppm)=8.83(1H), 8.37(1H), 8.14(2H), 8.04(1H), 8.02(1H), 7.94(1H), 7.90(1H), 7.89(1H), 7. 80-7.72(5H), 7.70(1H), 7.67-7.55(5H), 7.43-7.31(4H), 7.31-7.25(4H), 7.23(2H), 7.20(1H).

[0288] Embodiment 22

[0289] <Synthesis of N-(4'-benzoxazol-2-yl-[1,1']biphenyl-4-yl)-N-phenyl-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 177)>

[0290] In a nitrogen-purged reaction vessel, N-phenyl-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine: 10.0 g, 2-(4'-chloro-[1,1']biphenyl-4-yl)-benzoxazole: 7.7 g, tris(dibenzylideneacetone)dipalladium(0): 0.4 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 4.4 g were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 9.9 g (yield: 61.5%) of yellow powder of N-(4'-benzoxazol-2-yl-[1,1']biphenyl-4-yl)-N-phenyl-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 177).

[0291] [Chemistry 25]

[0292]

[0293] The structure of the obtained yellow powder was identified using NMR.

[0294] use 1 H-NMR (CDCl 3 ) The following 33 hydrogen signals were detected.

[0295] δ(ppm)=8.34(2H), 8.32(2H), 7.87(1H), 7.86(1H), 7.82(1H), 7.78(2H), 7.74 (4H), 7.68(1H), 7.65-7.55(8H), 7.42-7.32(4H), 7.28-7.23(6H), 7.14(1H).

[0296] Embodiment 23

[0297] <Synthesis of N-(4'-benzoxazol-2-yl-[1,1']biphenyl-4-yl)-N-phenyl-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 180)>

[0298] In a nitrogen-purged reaction vessel, N-phenyl-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine: 6.5 g, 2-(4'-chloro-[1,1']biphenyl-4-yl)-benzoxazole: 6.0 g, tris(dibenzylideneacetone)dipalladium(0): 0.3 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 3.4 g were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 6.1 g (yield: 53.7%) of yellow powder of N-(4'-benzoxazol-2-yl-[1,1']biphenyl-4-yl)-N-phenyl-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 180).

[0299] [Chemistry 26]

[0300]

[0301] The structure of the obtained yellow powder was identified using NMR.

[0302] use 1 H-NMR (CDCl 3 ) The following 29 hydrogen signals were detected.

[0303] δ(ppm)=8.34(2H), 8.31(2H), 7.83(3H), 7.77(2H), 7.65-7.59(5H), 7.59-7.53(4H), 7.42-7.33(4H), 7.28-7.22(6H), 7.14(1H).

[0304] Embodiment 24

[0305] <Synthesis of N-(4'-benzofuran-2-yl-[1,1']biphenyl-4-yl)-N-phenyl-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 182)>

[0306] In a nitrogen-purged reaction vessel, N-phenyl-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine: 6.5 g, 2-(4'-chloro-[1,1']biphenyl-4-yl)-benzofuran: 6.0 g, tris(dibenzylideneacetone)dipalladium(0): 0.3 g, tri-tert-butylphosphine: 0.2 g, sodium tert-butoxide: 3.4 g were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 5.4 g (yield: 47.7%) of light yellow powder of N-(4'-benzofuran-2-yl-[1,1']biphenyl-4-yl)-N-phenyl-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 182).

[0307] [Chemistry 27]

[0308]

[0309] The structure of the obtained light yellow powder was identified using NMR.

[0310] use 1 H-NMR (CDCl 3 ) The following 30 hydrogen signals were detected.

[0311] δ(ppm)=8.31(2H), 7.96(2H), 7.84(1H), 7.81(1H), 7.71(2H), 7.66-7.54(10H), 7.39-7.29(3H), 7.28-7.22(7H), 7.13(1H), 7.08(1H).

[0312] Embodiment 25

[0313] <Synthesis of N-(4'-benzooxazol-2-yl-[1,1']biphenyl-4-yl)-N-phenyl-N-{4-(2-naphth-2-yl-benzooxazol-6-yl)-phenyl}-amine (Compound 184)>

[0314] In a nitrogen-purged reaction vessel, 6.3 g of N-phenyl-N-{4-(2-naphthyl-2-yl-benzooxazol-6-yl)-phenyl}-amine, 5.1 g of 2-(4'-chloro-[1,1']biphenyl-4-yl)-benzoxazole, 0.3 g of tris(dibenzylideneacetone)dipalladium(0), 0.1 g of tri-tert-butylphosphine, and 2.9 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 3.4 g (yield: 32.7%) of yellow powder of N-(4'-benzoxazol-2-yl-[1,1']biphenyl-4-yl)-N-phenyl-N-{4-(2-naphthalen-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 184).

[0315] [Chemistry 28]

[0316]

[0317] The structure of the obtained yellow powder was identified using NMR.

[0318] use 1 H-NMR (CDCl 3 ) The following 31 hydrogen signals were detected.

[0319] δ(ppm)=8.81(1H), 8.36(1H), 8.34(2H), 8.02(1H), 8.01(1H), 7.93(1H), 7.86(1H)7.84 (1H), 7.82(1H), 7.78(2H), 7.66-7.56(8H), 7.42-7.33(4H), 7.36-7.23(6H), 7.15(1H).

[0320] Embodiment 26

[0321] <Synthesis of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzooxazol-2-yl-phenyl)-N-{4-(2-furan-2-yl-benzooxazol-6-yl)-phenyl}-amine (Compound 188)>

[0322] In a nitrogen-purged reaction vessel, 8.0 g of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzoxazol-2-yl-phenyl)-amine, 6.5 g of 6-(4-chloro-phenyl)-2-(furan-2-yl)-benzoxazole, 0.4 g of tris(dibenzylideneacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 2.9 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 8.4 g (yield: 63.9%) of yellow powder of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzoxazol-2-yl-phenyl)-N-{4-(2-furan-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 188).

[0323] [Chemistry 29]

[0324]

[0325] The structure of the obtained yellow powder was identified using NMR.

[0326] use 1 H-NMR (CDCl 3 ) The following 27 hydrogen signals were detected.

[0327] δ(ppm)=8.18(2H), 7.85(1H), 7.83(1H), 7.80(1H), 7.78(1H), 7.71(1H), 7.67-7 .57(5H), 7.55(1H), 7.36(2H), 7.35-7.28(9H), 7.26(1H), 7.01(1H), 6.66(1H).

[0328] Embodiment 27

[0329] <Synthesis of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzothiophen-2-yl-phenyl)-N-{4-(2-furan-2-yl-benzooxazol-6-yl)-phenyl}-amine (Compound 189)>

[0330] In a nitrogen-purged reaction vessel, N-(4-benzofuran-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-amine: 7.2 g, 6-(4-chloro-phenyl)-2-(furan-2-yl)-benzoxazole: 5.6 g, tris(dibenzylideneacetone)dipalladium(0): 0.3 g, tri-tert-butylphosphine: 0.1 g, sodium tert-butoxide: 2.5 g were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain 5.4 g (yield: 45.9%) of yellow powder of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-N-{4-(2-furan-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 189).

[0331] [Chemistry 30]

[0332]

[0333] The structure of the obtained yellow powder was identified using NMR.

[0334] use 1 H-NMR (CDCl 3 ) The following 28 hydrogen signals were detected.

[0335] δ(ppm)=7.88-7.76(6H), 7.72(1H), 7.68(2H), 7.64(1H), 7.62-7.58(3H), 7.54(1H), 7.52(1H), 7.41-7.23(11H), 6.98(1H), 6.66(1H).

[0336] Embodiment 28

[0337] <Synthesis of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzooxazol-2-yl-phenyl)-N-{4-(2-thiophen-2-yl-benzooxazol-6-yl)-phenyl}-amine (Compound 190)>

[0338] In a nitrogen-purged reaction vessel, 9.0 g of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzoxazol-2-yl-phenyl)-amine, 7.7 g of 6-(4-chloro-phenyl)-2-(thiophen-2-yl)-benzoxazole, 0.4 g of tris(dibenzylideneacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 3.2 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain a yellow powder of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzoxazol-2-yl-phenyl)-N-{4-(2-thiophen-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 190): 10.3 g (yield: 68.0%).

[0339] [Chemistry 31]

[0340]

[0341] The structure of the obtained yellow powder was identified using NMR.

[0342] use 1 H-NMR (CDCl 3 ) The following 27 hydrogen signals were detected.

[0343] δ(ppm)=8.18(2H), 7.96(1H), 7.86(1H), 7.81(1H), 7.79(1H), 7.78(1H), 7 .67-7.57(6H), 7.55(1H), 7.37(2H), 7.35-7.25(9H), 7.23(1H), 7.01(1H).

[0344] Embodiment 29

[0345] <Synthesis of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzothiophen-2-yl-phenyl)-N-{4-(2-thiophen-2-yl-benzooxazol-6-yl)-phenyl}-amine (Compound 191)>

[0346] In a nitrogen-purged reaction vessel, N-(4-benzofuran-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-amine: 7.2 g, 6-(4-chloro-phenyl)-2-(furan-2-yl)-benzoxazole: 5.9 g, tris(dibenzylideneacetone)dipalladium(0): 0.3 g, tri-tert-butylphosphine: 0.1 g, sodium tert-butoxide: 2.5 g were placed, and the mixture was stirred under reflux overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain 7.5 g (yield: 62.8%) of yellow powder of N-(4-benzofuran-2-yl-phenyl)-N-(4-benzothiophene-2-yl-phenyl)-N-{4-(2-thiophene-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 191).

[0347] [Chemistry 32]

[0348]

[0349] The structure of the obtained yellow powder was identified using NMR.

[0350] use 1 H-NMR (CDCl 3 ) The following 28 hydrogen signals were detected.

[0351] δ(ppm)=7.96(1H), 7.87-7.75(6H), 7.68(2H), 7.61(5H), 7.55(1H), 7.52(1H), 7.38(1H), 7.36-7.21(10H), 6.97(1H).

[0352] Embodiment 30

[0353] <Synthesis of N-(4-naphth-2-yl-phenyl)-N-(2-phenyl-benzoxazol-6-yl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 192)>

[0354] In a nitrogen-purged reaction vessel, 6.2 g of N-(4-naphthyl-2-yl-phenyl)-N-(2-phenyl-benzoxazol-6-yl)-amine, 5.1 g of 6-(4-chloro-phenyl)-2-phenyl-benzoxazole, 0.3 g of tris(dibenzylideneacetone)dipalladium(0), 0.1 g of tri-tert-butylphosphine, and 2.9 g of sodium tert-butoxide were placed, and the mixture was refluxed and stirred overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 6.4 g of yellow powder of N-(4-naphthyl-2-yl-phenyl)-N-(2-phenyl-benzoxazol-6-yl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 192) (yield: 62.7%).

[0355] [Chemistry 33]

[0356]

[0357] The structure of the obtained yellow powder was identified using NMR.

[0358] use 1 H-NMR (CDCl 3 ) The following 31 hydrogen signals were detected.

[0359] δ(ppm)=8.31(2H), 8.25(2H), 8.08(1H), 7.93(2H), 7.89(1H), 7.84(1H), 7.82(1H), 7 .79(1H), 7.72(3H), 7.64(1H), 7.62(2H), 7.60-7.47(8H), 7.46(1H), 7.35-7.25(5H).

[0360] Embodiment 31

[0361] <Synthesis of N-(4-dibenzofuran-3-yl-phenyl)-N-(2-phenyl-benzoxazol-6-yl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 193)>

[0362] In a nitrogen-purged reaction vessel, 8.8 g of N-(4-dibenzofuran-3-yl-phenyl)-N-(2-phenyl-benzoxazol-6-yl)-amine, 6.5 g of 6-(4-chloro-phenyl)-2-phenyl-benzoxazole, 0.4 g of tris(dibenzylideneacetone)dipalladium(0), 0.2 g of tri-tert-butylphosphine, and 3.7 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain a yellow powder of N-(4-dibenzofuran-3-yl-phenyl)-N-(2-phenyl-benzoxazol-6-yl)-N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 193): 10.2 g (yield: 72.8%).

[0363] [Chemistry 34]

[0364]

[0365] The structure of the obtained yellow powder was identified using NMR.

[0366] use 1 H-NMR (CDCl 3 ) The following 31 hydrogen signals were detected.

[0367] δ(ppm)=8.31(2H), 8.25(2H), 8.01(1H), 7.99(1H), 7.84(1H), 7.82(2H), 7.72(1H), 7 .69-7.59(7H), 7.59-7.52(6H), 7.49(1H), 7.46(1H), 7.38(1H), 7.31(4H), 7.28(1H).

[0368] Embodiment 32

[0369] <Synthesis of N-(4-naphth-2-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 195)>

[0370] In a nitrogen-purged reaction vessel, 4.5 g of 4-(naphthalene-2-yl)-aniline, 13.8 g of 6-(4-chloro-phenyl)-2-phenyl-benzoxazole, 0.8 g of tris(dibenzylideneacetone)dipalladium(0), 0.3 g of tri-tert-butylphosphine, and 6.0 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 7.3 g of a yellow powder of N-(4-naphthalene-2-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazole-6-yl)-phenyl}-amine (Compound 195) (yield: 46.8%).

[0371] [Chemistry 35]

[0372]

[0373] The structure of the obtained yellow powder was identified using NMR.

[0374] use 1 H-NMR (CDCl 3 ) The following 35 hydrogen signals were detected.

[0375] δ(ppm)=8.32(4H), 8.08(1H), 7.94(2H), 7.89(1H), 7.87-7.82(4H), 7.80(1H), 7.72(2H), 7.67-7.61(6H), 7.61-7.47(8H), 7.38-7.31(6H).

[0376] Embodiment 33

[0377] <Synthesis of N-(4-quinolin-3-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 196)>

[0378] In a nitrogen-purged reaction vessel, 4-(quinolin-3-yl)-aniline: 3.9 g, 6-(4-chloro-phenyl)-2-phenyl-benzoxazole: 11.9 g, tris(dibenzylideneacetone)dipalladium(0): 0.7 g, tri-tert-butylphosphine: 0.3 g, sodium tert-butoxide: 4.3 g were placed, and refluxed with stirring overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain a yellow powder of N-(4-quinolin-3-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazole-6-yl)-phenyl}-amine (Compound 196): 4.2 g (yield: 31.3%).

[0379] [Chemistry 36]

[0380]

[0381] The structure of the obtained yellow powder was identified using NMR.

[0382] use 1 H-NMR (CDCl 3 ) The following 34 hydrogen signals were detected.

[0383] δ(ppm)=9.25(1H), 8.35-8.27(5H), 8.17(1H), 7.91(1H), 7.85(2H), 7.83(2H), 7 .75(1H), 7.71(2H), 7.65(6H), 7.62(1H), 7.60-7.54(6H), 7.38(2H), 7.35(4H).

[0384] Embodiment 34

[0385] <Synthesis of N-(4-thiophen-2-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 198)>

[0386] In a nitrogen-substituted reaction vessel, 2.9 g of 4-(thiophene-2-yl)-aniline, 11.1 g of 6-(4-chloro-phenyl)-2-phenyl-benzoxazole, 0.6 g of tris(dibenzylideneacetone)dipalladium(0), 0.3 g of tri-tert-butylphosphine, and 4.0 g of sodium tert-butoxide were placed, and the mixture was refluxed and stirred overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 7.4 g of a golden yellow powder of N-(4-benzofuran-2-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazole-6-yl)-phenyl}-amine (Compound 198) (yield: 62.6%).

[0387] [Chemistry 37]

[0388]

[0389] The structure of the obtained golden yellow powder was identified using NMR.

[0390] use 1 H-NMR (CDCl 3 ) The following 31 hydrogen signals were detected.

[0391] δ(ppm)=8.31(4H), 7.84(2H), 7.82(2H), 7.66-7.52(14H), 7.33-7.26(7H), 7.24(1H), 7.11(1H).

[0392] Embodiment 35

[0393] <Synthesis of N-(dibenzofuran-3-yl)-N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 199)>

[0394] In a nitrogen-substituted reaction vessel, N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine: 7.0 g, 3-bromo-dibenzofuran: 3.4 g, tri(dibenzylideneacetone)dipalladium(0): 0.2 g, tri-tert-butylphosphine: 0.1 g, sodium tert-butoxide: 2.4 g were placed, and refluxed with stirring overnight in toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain 6.2 g (yield: 68.1%) of a yellow powder of N-(dibenzofuran-3-yl)-N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 199).

[0395] [Chemistry 38]

[0396]

[0397] The structure of the obtained yellow powder was identified using NMR.

[0398] use 1 H-NMR (CDCl 3 ) The following 31 hydrogen signals were detected.

[0399] δ(ppm)=8.31(4H), 7.92(1H), 7.87(1H), 7.84(2H), 7.81(2H), 7.66-7.59( 6H), 7.59-7.52(7H), 7.43(1H), 7.42(1H), 7.36(1H), 7.32(4H), 7.24(1H).

[0400] Embodiment 36

[0401] <Synthesis of N-(dibenzothiophen-2-yl)-N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 200)>

[0402] In a nitrogen-substituted reaction vessel, 4.5 g of 2-amino-dibenzothiophene, 15.2 g of 6-(4-chloro-phenyl)-2-phenyl-benzoxazole, 0.8 g of tris(dibenzylideneacetone)dipalladium(0), 0.4 g of tri-tert-butylphosphine, and 6.5 g of sodium tert-butoxide were placed, and the mixture was refluxed and stirred overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 11.1 g (yield: 66.5%) of a yellow powder of N-(dibenzothiophene-2-yl)-N,N-bis{4-(2-phenyl-benzoxazole-6-yl)-phenyl}-amine (Compound 200).

[0403] [Chemistry 39]

[0404]

[0405] The structure of the obtained yellow powder was identified using NMR.

[0406] use 1 H-NMR (CDCl 3 ) The following 31 hydrogen signals were detected.

[0407] δ(ppm)=8.31(4H), 8.06(1H), 8.05(1H), 7.89(1H), 7.86-7.81(5H), 7.65( 2H), 7.62(4H), 7.59-7.53(6H), 7.48(1H), 7.43(1H), 7.40(1H), 7.32(4H).

[0408] Embodiment 37

[0409] <Synthesis of N-(4-benzoxazol-2-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 201)>

[0410] In a nitrogen-purged reaction vessel, 4.0 g of 4-benzoxazol-2-yl-aniline, 12.8 g of 6-(4-chloro-phenyl)-2-phenyl-benzoxazole, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.3 g of tri-tert-butylphosphine, and 5.5 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain 9.4 g of a yellow powder of N-(4-benzoxazol-2-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 201) (yield: 66.2%).

[0411] [Chemistry 40]

[0412]

[0413] The structure of the obtained yellow powder was identified using NMR.

[0414] use 1 H-NMR (CDCl 3 ) The following 32 hydrogen signals were detected.

[0415] δ(ppm)=8.32(4H), 8.19(2H), 7.88-7.83(4H), 7.78(1H), 7.71-7.63(6H), 7.62-7.54(7H), 7.41-7.33(6H), 7.31(2H).

[0416] Embodiment 38

[0417] <Synthesis of N-(4-benzofuran-2-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 203)>

[0418] In a nitrogen-purged reaction vessel, 4-(benzofuran-2-yl)-aniline: 3.2 g, 6-(4-chloro-phenyl)-2-phenyl-benzoxazole: 10.3 g, tri(dibenzylideneacetone)dipalladium(0): 0.6 g, tri-tert-butylphosphine: 0.3 g, sodium tert-butoxide: 3.7 g were placed, and the mixture was refluxed and stirred overnight in a xylene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a toluene / acetone mixed solvent to obtain 5.8 g (yield: 50.7%) of a yellow powder of N-(4-benzofuran-2-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazole-6-yl)-phenyl}-amine (Compound 203).

[0419] [Chemistry 41]

[0420]

[0421] The structure of the obtained yellow powder was identified using NMR.

[0422] use 1 H-NMR (CDCl 3 ) The following 33 hydrogen signals were detected.

[0423] δ(ppm)=8.32(4H), 7.85(2H), 7.82(4H), 7.67-7.52(14H), 7.32(4H), 7.31-7.22(3H), 7.26(1H), 6.98(1H).

[0424] Embodiment 39

[0425] <Synthesis of N-(4-benzothiophen-2-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-amine (Compound 204)>

[0426] In a nitrogen-purged reaction vessel, 4.5 g of 4-(benzothiophene-2-yl)-aniline, 13.4 g of 6-(4-chloro-phenyl)-2-phenyl-benzoxazole, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.3 g of tri-tert-butylphosphine, and 5.8 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain 10.5 g of yellow powder of N-(4-benzothiophene-2-yl-phenyl)-N,N-bis{4-(2-phenyl-benzoxazole-6-yl)-phenyl}-amine (Compound 204) (yield: 68.6%).

[0427] [Chemistry 42]

[0428]

[0429] The structure of the obtained yellow powder was identified using NMR.

[0430] use 1 H-NMR (CDCl 3 ) The following 33 hydrogen signals were detected.

[0431] δ(ppm)=8.32(4H), 7.88-7.81(5H), 7.79(1H), 7.69(2H), 7.67-7.61(6H), 7.58(4H), 7.57(2H), 7.52(1H), 7.38(1H), 7.32(5H), 7.27(2H).

[0432] Embodiment 40

[0433] <Synthesis of N-phenyl-N,N-bis{4-(2-naphth-2-yl-benzoxazol-6-yl)-phenyl}-amine (Compound 205)>

[0434] Aniline: 2.0 g, 6-(4-chloro-phenyl)-2-(naphthalene-2-yl)-benzoxazole: 16.1 g, tris(dibenzylideneacetone)dipalladium(0): 1.0 g, tri-tert-butylphosphine: 0.9 g, sodium tert-butoxide: 6.2 g were placed in a nitrogen-purged reaction vessel, and refluxed with stirring overnight in a toluene solvent. After natural cooling, ethanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The obtained crude product was purified by crystallization using a chlorobenzene / acetone mixed solvent to obtain 12.7 g (yield: 80.8%) of a yellow powder of N-phenyl-N,N-bis{4-(2-naphthalene-2-yl-benzoxazole-6-yl)-phenyl}-amine (Compound 205).

[0435] [Chemistry 43]

[0436]

[0437] The structure of the obtained yellow powder was identified using NMR.

[0438] use 1 H-NMR (CDCl 3 ) The following 33 hydrogen signals were detected.

[0439] δ(ppm)=8.81(2H), 8.35(2H), 8.01(4H), 7.92(2H), 7.86(2H), 7.83(2H), 7.64(2H), 7.63-7.56(8H), 7.37(2H), 7.31-7.25(6H), 7.14(1H).

[0440] Embodiment 41

[0441] <Synthesis of N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-N-phenyl-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 206)>

[0442] In a nitrogen-purged reaction vessel, 6.4 g of N-phenyl-N-{4'-(2-phenyl-benzooxazol-6-yl)-[1,1']biphenyl-4-yl}-amine, 4.9 g of 6-(4-chloro-phenyl)-2-phenyl-benzooxazole, 0.3 g of tris(dibenzylideneacetone)dipalladium(0), 0.1 g of tri-tert-butylphosphine, and 2.8 g of sodium tert-butoxide were placed, and the mixture was stirred under reflux overnight in a toluene solvent. After natural cooling, methanol was added to the system, and the precipitated solid was filtered out to obtain a crude product. The crude product was purified by crystallization using a dichloromethane / acetone mixed solvent to obtain 6.2 g (yield: 60.2%) of light yellow powder of N-{4-(2-phenyl-benzoxazol-6-yl)-phenyl}-N-phenyl-N-{4'-(2-phenyl-benzoxazol-6-yl)-[1,1']biphenyl-4-yl}-amine (Compound 206).

[0443] [Chemistry 44]

[0444]

[0445] The structure of the obtained light yellow powder was identified using NMR.

[0446] use 1 H-NMR (CDCl 3 ) The following 33 hydrogen signals were detected.

[0447] δ(ppm)=8.31(4H), 7.87(1H), 7.86(1H), 7.83(1H), 7.81(1H), 7.74(4H), 7.68(1H), 7.65-7.53(11H), 7.36(2H), 7.28-7.22(6H), 7.13(1H).

[0448] Embodiment 42

[0449] Table 1 shows the results of measuring the glass transition temperature and melting point of the compounds obtained in the above Examples using a high-sensitivity differential scanning calorimeter (DSC3100SA manufactured by Bruker-AXS).

[0450] [Table 1]

[0451] [Table 1-1]

[0452] Exemplary compounds Glass transition temperature Melting point Example 1 Compound 40 119℃ Not observed Example 2 Compound 50 115℃ 240℃ Example 3 Compound 69 134℃ Not observed Example 4 Compound 70 131℃ Not observed Example 5 Compound 78 125℃ 266℃ Example 6 Compound 119 118℃ Not observed Example 7 Compound 150 126℃ Not observed Example 8 Compound 2 115.7 Not observed Example 9 Compound 17 125.6 Not observed Example 10 Compound 38 122.7 Not observed Embodiment 11 Compound 52 114 245.3 Example 12 Compound 61 150.5 Not observed Example 13 Compound 62 122.3 265.2 Embodiment 14 Compound 71 132.6 Not observed Embodiment 15 Compound 79 127.9 261.4 Example 16 Compound 101 122.5 Not observed Embodiment 17 Compound 137 130 Not observed Embodiment 18 Compound 138 133.7 Not observed Embodiment 19 Compound 155 130.2 237.1 Embodiment 20 Compound 171 106.8 Not observed

[0453] [Table 1-2]

[0454] Embodiment 21 Compound 173 116.4 Not observed Embodiment 22 Compound 177 117.5 Not observed Embodiment 23 Compound 180 106.3 Not observed Embodiment 24 Compound 182 102.8 206.6 Embodiment 25 Compound 184 116.3 240.2 Embodiment 26 Compound 188 120.9 Not observed Embodiment 27 Compound 189 120.6 Not observed Embodiment 28 Compound 190 123.9 Not observed Embodiment 29 Compound 191 122.8 Not observed Embodiment 30 Compound 192 108.8 Not observed Embodiment 31 Compound 193 118.4 Not observed Embodiment 32 Compound 195 117.6 Not observed Embodiment 33 Compound 196 120.8 Not observed Embodiment 34 Compound 198 116.1 Not observed Embodiment 35 Compound 199 120.8 Not observed Embodiment 36 Compound 200 130 266.4 Embodiment 37 Compound 201 127.6 291.8 Embodiment 38 Compound 203 121.9 Not observed Embodiment 39 Compound 204 125.6 Not observed Embodiment 40 Compound 205 121.3 220.2 Embodiment 41 Compound 206 111.1 Not observed

[0455] The above measurement results show that the amine compound according to the present invention has a glass transition temperature of 100° C. or higher, indicating that the thin film state is stable.

[0456] Embodiment 43

[0457] Using the compounds obtained in the above examples, a vapor-deposited film with a thickness of 80 nm was prepared on a silicon substrate, and a spectrophotometer (manufactured by Filmetic Corporation, F10-RT-UV) was used to measure the refractive index n at wavelengths of 450 nm and 750 nm and the extinction coefficient k at wavelengths of 400 nm and 410 nm. For comparison, the comparative compounds (2-1), (2-2) and Alq 3 The results of the measurements of the refractive index n and the extinction coefficient k are summarized in Table 2 (see, for example, Patent Document 4 and Patent Document 5).

[0458] [Chemistry 45]

[0459]

[0460] [Chemistry 46]

[0461]

[0462] [Table 2]

[0463] [Table 2-1]

[0464]

[0465] [Table 2-2]

[0466] Example 16 Compound 101 2.43 1.93 1.07 0.79 Embodiment 17 Compound 137 2.36 1.91 099 0.68 Embodiment 18 Compound 138 2.38 1.92 0.99 0.70 Example 19 Compound 155 2.40 1.93 0.99 0.73 Embodiment 20 Compound 171 2.30 1.88 0.63 0.42 Embodiment 21 Compound 173 2.31 1.91 0.67 0.44 Embodiment 22 Compound 177 2.30 1.89 0.69 0.50 Embodiment 23 Compound 180 2.32 1.89 0.75 0.54 Embodiment 24 Compound 182 2.32 1.89 0.72 0.43 Embodiment 25 Compound 184 2.32 1.91 0.74 0.57 Embodiment 26 Compound 188 2.41 1.91 1.08 0.76 Embodiment 27 Compound 189 2.44 1.93 1.05 0.78 Embodiment 28 Compound 190 2.43 192 1.08 0.80 Embodiment 29 Compound 191 2.43 1.94 1.04 0.80 Embodiment 30 Compound 192 2.31 1.91 0.62 039 Embodiment 31 Compound 193 2.33 1.91 0.76 0.49 Embodiment 32 Compound 195 2.30 1.92 0.74 0.43 Embodiment 33 Compound 196 2.31 1.93 0.79 0.50 Embodiment 34 Compound 198 2.33 1.92 0.76 047 Embodiment 35 Compound 199 2.32 1.92 0.66 0.37 Embodiment 36 Compound 200 2.31 191 0.65 0.32 Embodiment 37 Compound 201 2.35 1.91 0.94 0.65 Embodiment 38 Compound 203 2.35 1.92 0.88 058 Embodiment 39 Compound 204 2.33 1.93 0.85 0.59 Embodiment 40 Compound 205 2.35 194 061 0.45 Embodiment 41 Compound 206 2.31 1.89 0.49 0.28 Comparative Example 1 Ala3 1.88 173 0.16 014 Comparative Example 2 Compound (2-1) 1.84 1.77 0.07 0.03 Comparative Example 3 Compound (2-2) 2.29 1.89 0.85 0.56

[0467] As shown in Table 2, the compound of the present invention has a refractive index equal to or greater than that of A1q3, comparative compound (2-1), and comparative compound (2-2) at wavelengths between 450 nm and 750 nm, and since the extinction coefficient at wavelengths of 400 nm and 410 nm is low, the loss of light absorption in the cyan region is small. This can be expected to improve the light extraction efficiency in an organic EL element using the amine compound of the present invention as a constituent material of a capping layer.

[0468] Embodiment 44

[0469] As for organic EL elements, Fig.21 As shown in the figure, a reflective ITO electrode is pre-formed on a glass substrate 1 as a transparent anode 2, and then a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, a cathode 8, and a capping layer 9 are sequentially deposited.

[0470] Specifically, a glass substrate 1 on which a 50 nm thick ITO film, a 100 nm thick silver alloy reflective film, and a 5 nm thick ITO film were sequentially formed was ultrasonically cleaned in isopropyl alcohol for 20 minutes and then dried on a hot plate heated to 250° C. for 10 minutes. Then, after a 2 minute UV ozone treatment, the glass substrate with ITO was mounted in a vacuum deposition machine and the pressure was reduced to below 0.001 Pa. Next, an electron acceptor (Acceptor-1) of the following structural formula and a compound (3-1) of the following structural formula were binary deposited at a deposition rate ratio of Acceptor-1: Compound (3-1) = 3:97 as a hole transport layer 3 to cover the transparent anode 2, and the film thickness was 10 nm. On the hole injection layer 3, a compound (3-1) of the following structural formula was formed as a hole transport layer 4 to a film thickness of 140 nm. On the hole transport layer 4, as the light-emitting layer 5, the compound (3-2) of the following structural formula and the compound (3-3) of the following structural formula were binary deposited at a deposition rate ratio of (3-2): (3-3) = 5:95, and the film thickness was 20nm. On the light-emitting layer 5, as the electron transport layer 6, the compound (3-4) of the following structural formula and the compound (3-5) of the following structural formula were binary deposited at a deposition rate ratio of (3-4): (3-5) = 50:50, and the film thickness was 30nm. On the electron transport layer 6, as the electron injection layer 7, lithium fluoride was formed in a film thickness of 1nm. On the electron injection layer 7, as the cathode 8, a magnesium-silver alloy was formed in a film thickness of 12nm. Finally, as the capping layer 9, the compound (40) of Example 1 was formed in a film thickness of 60nm. The characteristics of the produced organic EL element were measured in the atmosphere at room temperature.

[0471] Table 3 summarizes the results of measuring the light emission characteristics of the produced organic EL elements when a direct current voltage was applied.

[0472] [Chemistry 47]

[0473]

[0474] Embodiment 45

[0475] An organic EL element was prepared under the same conditions except that, as the capping layer 9 in Example 44, the compound (50) of Example 2 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0476] Embodiment 46

[0477] An organic EL element was prepared under the same conditions except that the compound (69) of Example 3 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0478] Embodiment 47

[0479] An organic EL element was prepared under the same conditions except that the compound (70) of Example 4 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0480] Embodiment 48

[0481] An organic EL element was prepared under the same conditions except that the compound (78) of Example 5 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0482] Embodiment 49

[0483] An organic EL element was prepared under the same conditions except that the compound (119) of Example 6 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0484] Embodiment 50

[0485] An organic EL element was prepared under the same conditions except that the compound (150) of Example 7 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0486] Embodiment 51

[0487] An organic EL element was prepared under the same conditions except that, as the capping layer 9 in Example 44, the compound (2) of Example 8 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0488] Embodiment 52

[0489] An organic EL element was prepared under the same conditions except that, as the capping layer 9, the compound (17) of Example 9 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0490] Embodiment 53

[0491] An organic EL element was prepared under the same conditions except that in Example 44, the compound (38) of Example 10 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0492] Embodiment 54

[0493] An organic EL element was prepared under the same conditions except that the compound (52) of Example 11 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0494] Embodiment 55

[0495] An organic EL element was prepared under the same conditions except that, as the capping layer 9 in Example 44, the compound (61) of Example 12 was formed in a manner to have a film thickness of 60 nm instead of the compound (40) of Example 1. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0496] Embodiment 56

[0497] An organic EL element was prepared under the same conditions except that the compound (62) of Example 13 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0498] Embodiment 57

[0499] An organic EL element was prepared under the same conditions except that the compound (71) of Example 14 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0500] Embodiment 58

[0501] An organic EL element was prepared under the same conditions except that the compound (79) of Example 15 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0502] Embodiment 59

[0503] An organic EL element was prepared under the same conditions except that the compound (101) of Example 16 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0504] Embodiment 60

[0505] An organic EL element was prepared under the same conditions except that the compound (137) of Example 17 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0506] Embodiment 61

[0507] An organic EL element was prepared under the same conditions except that the compound (138) of Example 18 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0508] Embodiment 62

[0509] An organic EL element was prepared under the same conditions except that the compound (155) of Example 19 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0510] Embodiment 63

[0511] An organic EL element was prepared under the same conditions except that the compound (171) of Example 20 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0512] Embodiment 64

[0513] An organic EL element was prepared under the same conditions except that the compound (173) of Example 21 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0514] Embodiment 65

[0515] An organic EL element was prepared under the same conditions except that the compound (177) of Example 22 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0516] Embodiment 66

[0517] An organic EL element was prepared under the same conditions except that the compound (180) of Example 23 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0518] Embodiment 67

[0519] An organic EL element was prepared under the same conditions except that the compound (182) of Example 24 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0520] Embodiment 68

[0521] An organic EL element was prepared under the same conditions except that the compound (184) of Example 25 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0522] Embodiment 69

[0523] An organic EL element was prepared under the same conditions except that the compound (188) of Example 26 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0524] Embodiment 70

[0525] An organic EL element was prepared under the same conditions except that the compound (189) of Example 27 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0526] Embodiment 71

[0527] An organic EL element was prepared under the same conditions except that the compound (190) of Example 28 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0528] Embodiment 72

[0529] An organic EL element was prepared under the same conditions except that the compound (191) of Example 29 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0530] Embodiment 73

[0531] An organic EL element was prepared under the same conditions except that the compound (192) of Example 30 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0532] Embodiment 74

[0533] An organic EL element was prepared under the same conditions except that the compound (193) of Example 31 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0534] Embodiment 75

[0535] An organic EL element was prepared under the same conditions except that the compound (195) of Example 32 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0536] Embodiment 76

[0537] An organic EL element was prepared under the same conditions except that the compound (196) of Example 33 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0538] Embodiment 77

[0539] An organic EL element was prepared under the same conditions except that the compound (198) of Example 34 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0540] Embodiment 78

[0541] An organic EL element was prepared under the same conditions except that the compound (199) of Example 35 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0542] Embodiment 79

[0543] An organic EL element was prepared under the same conditions except that the compound (200) of Example 36 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0544] Embodiment 80

[0545] An organic EL element was prepared under the same conditions except that the compound (201) of Example 37 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0546] Embodiment 81

[0547] An organic EL element was prepared under the same conditions except that the compound (203) of Example 38 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0548] Embodiment 82

[0549] An organic EL element was prepared under the same conditions except that the compound (204) of Example 39 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1 as the capping layer 9 in Example 44. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0550] Embodiment 83

[0551] An organic EL element was prepared under the same conditions except that, as the capping layer 9 in Example 44, the compound (205) of Example 40 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0552] Embodiment 84

[0553] An organic EL element was prepared under the same conditions except that, as the capping layer 9 in Example 44, the compound (206) of Example 41 was formed in a film thickness of 60 nm instead of the compound (40) of Example 1. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0554] [Comparative Example 4]

[0555] For comparison, in Example 44, instead of the compound (40) of Example 1, Alq was formed as the capping layer 9 to a film thickness of 60 nm. 3 The organic EL element was produced under the same conditions except for the above. The characteristics of the produced organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the light emission characteristics of the produced organic EL element when a direct current voltage was applied are summarized in Table 3.

[0556] [Comparative Example 5]

[0557] For comparison, an organic EL element was prepared under the same conditions except that in Example 44, as the capping layer 9, the compound (2-1) was formed in a manner of 60 nm instead of the compound (40) of Example 1. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0558] [Comparative Example 6]

[0559] For comparison, an organic EL element was prepared under the same conditions except that in Example 44, as the capping layer 9, the compound (2-2) was formed in a manner of 60 nm instead of the compound (40) of Example 1. The characteristics of the prepared organic EL element were measured in the atmosphere at room temperature. The results of the measurement of the luminescent characteristics of the prepared organic EL element with a DC voltage applied are summarized in Table 3.

[0560] The results of measuring the device life using the organic EL devices prepared in Examples 44 to 84 and Comparative Examples 4 to 6 are summarized in Table 3. The device life was measured at 10 mA / cm 2 The initial brightness during constant current driving was set to 100%, and the time until the brightness was decayed to 95% was measured.

[0561] [Table 3]

[0562] [Table 3-1]

[0563]

[0564] [Table 3-2]

[0565] Embodiment 56 Compound 62 362 833 8.33 7.22 156 hours Embodiment 57 Compound 71 3.62 833 8.33 7.24 159 hours Embodiment 58 Compound 79 3.65 832 8.32 7.16 168 hours Embodiment 59 Chemicals 101 3.64 833 8.34 7.20 164 hours Embodiment 60 Compound 137 3.63 823 8.23 7.11 157 hours Embodiment 61 Compound 138 3.64 824 8.24 7.12 166 hours Embodiment 62 Compound 155 3.65 831 8.30 7.15 154 hours Embodiment 63 Compound 171 3.65 812 8.11 6.98 140 hours Embodiment 64 Compound 173 3.66 821 8.21 7.06 167 hours Embodiment 65 Compound 177 3.62 814 8.14 7.07 142 hours Embodiment 66 Compound 180 3.65 819 8.19 7.04 171 hours Embodiment 67 Compound 182 3.66 821 8.20 7.04 148 hours Embodiment 68 Compound 184 3.64 822 8.22 7.09 141 hours Embodiment 69 Compound 188 3.63 833 8.32 7.20 167 hours Embodiment 70 Compound 189 3.61 835 8.35 7.25 171 hours Embodiment 71 Compound 190 3.63 832 8.31 7.19 151 hours Embodiment 72 Compound 191 3.64 832 8.32 7.17 169 hours Embodiment 73 Compound 192 3.65 817 8.16 7.03 154 hours Embodiment 74 Compound 193 3.63 834 8.33 7.20 173 hours Embodiment 75 Compound 195 3.65 819 8.18 7.04 165 hours Embodiment 76 Compound 196 3.63 822 8.22 7.12 158 hours Embodiment 77 Compound 198 3.64 827 827 7.14 152 hours Embodiment 78 Compound 199 3.64 830 8.30 7.16 166 hours Embodiment 79 Compound 200 3.65 822 8.21 7.07 149 hours Embodiment 80 Compound 201 3.66 824 8.24 7.07 150 hours Embodiment 81 Compound 203 3.64 829 8.28 7.15 142 hours Embodiment 82 Compound 204 3.63 819 8.19 7.09 158 hours Embodiment 83 Compound 205 3.65 825 8.25 7.11 163 hours Embodiment 84 Compound 206 364 816 8.17 7.06 173 hours Comparative Example 4 Alq3 3.65 714 7.14 6.15 114 hours Comparative Example 5 Compound (2-1) 3.65 709 7.08 6.10 121 hours Comparative Example 6 Compound (2-2) 3.63 789 7.89 6.83 138 hours

[0566] As shown in Table 3, at a current density of 10 mA / cm 2 In terms of the driving voltage at , the elements of Comparative Examples 4 to 6 are substantially equivalent to the elements of Examples 44 to 84, whereas the elements of Examples 10 to 16 are significantly improved relative to the elements of Comparative Examples 4 to 6 in terms of brightness, luminous efficiency, power efficiency, and life. This indicates that the amine compound of the present invention is a suitable material for a capping layer, and since the capping layer has a high refractive index and a low extinction coefficient, it is possible to significantly improve the light extraction efficiency in an organic EL element.

[0567] Industrial Applicability

[0568] The amine compound of the present invention has a high refractive index and a low extinction coefficient, can greatly improve the light extraction efficiency, and is stable in a thin film state, so it is excellent as a compound suitable for an organic EL element. The organic EL element made using the amine compound of the present invention can obtain high efficiency. In addition, by using the amine compound of the present invention that does not have absorption in each wavelength region of cyan, green and red, it is particularly suitable when it is desired to display a clear and bright image with good color purity. For example, it can be expanded to the use of household electrical products and lighting.

[0569] Description of Reference Numerals

[0570] 1 Glass substrate

[0571] 2 Transparent anode

[0572] 3 Hole injection layer

[0573] 4 Hole transport layer

[0574] 5. Luminous layer

[0575] 6 Electron Transport Layer

[0576] 7 Electron injection layer

[0577] 8 Cathode

[0578] 9 Capping layer

Claims

1. An amine compound represented by the following general formula (A), In the formula, Ar1 represents a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, Ar2 and Ar3 may be the same or different and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. L1 to L3 may be the same as or different from each other, and represent a single bond, a divalent group obtained by removing two hydrogen atoms from unsubstituted benzene, a divalent group obtained by removing two hydrogen atoms from unsubstituted biphenyl, or a divalent group obtained by removing two hydrogen atoms from unsubstituted naphthalene. X represents an oxygen atom or a sulfur atom.

2. The amine compound according to claim 1, which is represented by the following general formula (B) or (C), In the formula, Ar1 to Ar3, L1 to L3 and X have the same definitions as those in the general formula (A).

3. The amine compound according to claim 2, wherein L1 to L3 in the general formula (A), (B) or (C) are single bonds, unsubstituted 1,4-phenylene, unsubstituted 4,4'-biphenylene, unsubstituted 2,6-naphthylene or unsubstituted 2,7-naphthylene.

4. The amine compound according to claim 3, wherein Ar3 in the general formula (A), (B) or (C) is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted furanyl group, or a substituted or unsubstituted thienyl group.

5. The amine compound according to claim 4, wherein Ar3 in the general formula (A), (B) or (C) is an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted furyl group, or an unsubstituted thienyl group.

6. The amine compound according to claim 3, wherein Ar1 in the general formula (A), (B) or (C) is substituted or unsubstituted 2-benzoxazolyl, substituted or unsubstituted 2-benzothiazolyl, substituted or unsubstituted 2-benzofuranyl, substituted or unsubstituted 2-benzothiophenyl, substituted or unsubstituted 2-dibenzofuranyl, substituted or unsubstituted 2-dibenzothiophenyl, substituted or unsubstituted 3-dibenzofuranyl, or substituted or unsubstituted 3-dibenzothiophenyl.

7. The amine compound according to claim 6, wherein Ar1 in the general formula (A), (B) or (C) is an unsubstituted 2-benzoxazolyl, an unsubstituted 2-benzothiazolyl, an unsubstituted 2-benzofuranyl, an unsubstituted 2-benzothiophenyl, an unsubstituted 2-dibenzofuranyl, an unsubstituted 2-dibenzothiophenyl, an unsubstituted 3-dibenzofuranyl, or an unsubstituted 3-dibenzothiophenyl.

8. The amine compound according to claim 7, wherein In the general formula (A), (B) or (C), Ar3 is an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted furyl group, or an unsubstituted thienyl group.

9. An organic EL element, comprising at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode and a capping layer in this order, wherein: The capping layer contains the amine compound according to claim 1 or claim 2.

10. The organic EL element according to claim 9, characterized in that In the capping layer, the extinction coefficient thereof is greater than 0.2 in the wavelength range of 400 nm to 410 nm, and the concentration is 10 -5 The absorbance in the absorption spectrum of mol / L is 0.2 or more in the wavelength range of 400 nm to 410 nm.

11. The organic EL element according to claim 9, characterized in that The refractive index of the capping layer is 1.85 or more within a range of 450 nm to 750 nm of wavelength of light passing through the capping layer.

12. An organic EL element, comprising at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode and a capping layer in this order, wherein: The capping layer is a laminated or mixed layer composed of two or more compounds, at least one of which is the amine compound according to claim 1 or claim 2.

13. An electronic device or electronic component comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein: The organic layer contains the amine compound according to claim 1 or claim 2.

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