Organic compound and organic light-emitting device

Abstract

To provide an organic compound that can be used in an organic light-emitting device to have excellent luminous efficiency and durability and give blue light emission of good color purity.SOLUTION: An organic compound has a specific 5-membered ring structure including an N-B-N bond as ring-constituting elements represented by, for example, the general formula[7].SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an organic compound and an organic light-emitting device using the same. [Background technology]

[0002] An organic light-emitting device (hereinafter sometimes referred to as an "organic electroluminescence device" or "organic EL device") is an electronic device having a pair of electrodes and an organic compound layer disposed between the electrodes. By injecting electrons and holes from the pair of electrodes, excitons of a light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting device emits light. Recent advances in organic light-emitting devices have been remarkable, including low driving voltage, diverse emission wavelengths, high-speed response, and the possibility of thinning and reducing the weight of light-emitting devices. Furthermore, the sRGB and AdobeRGB standards are used to represent the color reproduction range of displays, and materials that can reproduce these have been in demand. Recently, however, BT-2020 has been proposed as a standard that will further expand the color reproduction range. Incidentally, there has been active research into the creation of luminescent organic compounds. This is because the creation of compounds with excellent luminescent properties is important for providing high-performance organic light-emitting devices. Patent Document 1 describes the following compound 1-a.

[0003] [ka] [Prior art documents] [Patent documents]

[0004] [Patent Document 1] US Patent Application Publication No. 2016 / 0351811 Summary of the Invention [Problem to be solved by the invention]

[0005] Patent Document 1 discloses a synthesis example of Compound 1-a, but does not suggest anything about the luminous efficiency or luminescent color. Furthermore, considering the blue color reproduction range corresponding to the sRGB, AdobeRGB, and BT2020 standards, further improvement in the color purity of blue light emission is desired. Further improvement in color purity or durability is desired for organic light-emitting devices using these compounds. The present invention has been made in view of the above problems, and an object of the present invention is to provide a blue light-emitting material that is excellent in luminous efficiency and durability and has good color purity. [Means for solving the problem]

[0006] The organic compound of the present invention is characterized by being represented by either of the following general formulas [1-1] and [1-2].

[0007] [ka] In the above formulas [1-1] and [1-2], R1 to R8 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a cyano group, a silyl group, and a deuterium atom, provided that R4 may be bonded to Ar1 to form a ring. Ar1 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. Ar2 is any of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, and a substituted or unsubstituted quinolyl group; represents a divalent linking group derived from The phenyl group, the biphenyl group, the naphthyl group, the pyridyl group, the pyrimidyl group, and the quinolyl group are bonded to adjacent carbon atoms. X1 and X2 are each independently selected from an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, and a nitrogen atom having a substituent Z, and the substituent Z is selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and deuterium. [Effects of the Invention]

[0008] The organic compound of the present invention is a blue light-emitting material having high color purity and high oscillator strength, and therefore high luminous efficiency. Therefore, when used in an organic light-emitting device, particularly in an emitting layer thereof, it is possible to provide an organic light-emitting device having excellent color purity, luminous efficiency, and durability. [Brief explanation of the drawings]

[0009] [Figure 1] 1A is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention, and FIG. 1B is a schematic cross-sectional view showing an example of a display device using an organic light-emitting element according to one embodiment of the present invention. [Figure 2] 1A is a schematic diagram of an image forming apparatus according to one embodiment of the present invention, and FIGS. 1B and 1C are schematic diagrams showing a configuration in which a plurality of light-emitting units of an exposure light source are arranged on a long substrate. [Figure 3] 1 is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention. [Figure 4] 1A is a schematic diagram illustrating an example of an imaging device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of an electronic device according to an embodiment of the present invention. [Figure 5] 1A is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of a foldable display device. [Figure 6] 1A is a schematic diagram showing an example of an illumination device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing an example of an automobile having a vehicle lamp according to an embodiment of the present invention. [Figure 7] 1A is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, having an imaging device. DETAILED DESCRIPTION OF THE INVENTION

[0010] ≪Organic compounds≫ First, the organic compound of the present invention will be described. The organic compound of the present invention is an organic compound represented by either of the following general formulas [1-1] and [1-2].

[0011] [ka]

[0012] In the above formulas [1-1] and [1-2], R1 to R8 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a cyano group, a silyl group, and a deuterium atom, provided that R4 may be bonded to Ar1 to form a ring. Ar1 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. Ar2 represents a divalent linking group derived from a substituted or unsubstituted divalent arylene group or a substituted or unsubstituted heterocyclic group. X1 and X2 are each independently selected from an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, and a nitrogen atom having a substituent Z, and the substituent Z is selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and deuterium.

[0013] The halogen atoms, alkyl groups, alkoxy groups, amino groups, aryl groups, heteroaryl groups, aryloxy groups, and silyl groups represented by R1 to R8 will be specifically described. Examples of halogen atoms include, but are not limited to, fluorine, chlorine, bromine, and iodine.

[0014] Preferred examples of the alkyl group include alkyl groups having 1 or more and 10 or less carbon atoms, such as a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a 1-adamantyl group, and a 2-adamantyl group.

[0015] Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, 2-ethyl-octyloxy, and benzyloxy groups. Among these, alkoxy groups having 1 to 6 carbon atoms are preferred.

[0016] Examples of the amino group include, but are not limited to, an N-methylamino group, an N-ethylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-methyl-N-ethylamino group, an N-benzylamino group, an N-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilino group, an N,N-diphenylamino group, an N,N-dinaphthylamino group, an N,N-difluorenylamino group, an N-phenyl-N-tolylamino group, an N,N-ditolylamino group, an N-methyl-N-phenylamino group, an N,N-dianisolylamino group, an N-mesityl-N-phenylamino group, an N,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, and an N-piperidyl group.

[0017] The aryl group is preferably an aryl group having 6 or more and 18 or less carbon atoms, such as a phenyl group, naphthyl group, indenyl group, biphenyl group, terphenyl group, fluorenyl group, phenanthryl group, or triphenylenyl group.

[0018] The heteroaryl group is preferably a heteroaryl group having 3 or more and 15 or less carbon atoms, and examples thereof include, but are not limited to, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, an oxazolyl group, a thiazolyl group, an imidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzimidazolyl group, a thienyl group, a furanyl group, a pyrrolyl group, a benzothienyl group, a benzofuranyl group, an indonyl group, a dibenzothiophenyl group, and a dibenzofuranyl group.

[0019] The aryloxy group is preferably an aryloxy group having 6 to 18 carbon atoms, and examples thereof include a phenoxy group and a thienyloxy group, but are not limited to these.

[0020] Examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0021] Next, Ar1 and Ar2 will be specifically described. Ar1 is an aryl group or a heterocyclic group, and the heterocyclic group is preferably a heteroaryl group. Ar1 may be unsubstituted or substituted.

[0022] Examples of the aryl group include a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, and a triphenylenyl group.

[0023] Examples of heteroaryl groups include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, an oxazolyl group, a thiazolyl group, an imidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzimidazolyl group, a thienyl group, a furanyl group, a pyronyl group, a benzothienyl group, a benzofuranyl group, an indonyl group, a dibenzothiophenyl group, and a dibenzofuranyl group.

[0024] In the formulas [1-1] and [1-2], R4 may be bonded to Ar1 to form a ring as a divalent linking group.

[0025] Ar2 is a divalent linking group derived from a divalent arylene group or a heterocyclic group, and the heterocyclic group is preferably a heteroarylene group. Ar2 may be unsubstituted or substituted.

[0026] Examples of the arylene group include divalent linking groups derived from a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, and the like.

[0027] Examples of heteroarylene groups include divalent linking groups derived from a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, an oxazolyl group, a thiazolyl group, an imidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzimidazolyl group, a thienyl group, a furanyl group, a pyrrolyl group, a benzothienyl group, a benzofuranyl group, an indonyl group, a dibenzothiophenyl group, a dibenzofuranyl group, and the like.

[0028] Next, the case where X1 and X2 are nitrogen atoms having a substituent Z, and Z is an alkyl group, an aryl group, or a heteroaryl group, will be specifically described. Preferred examples of the alkyl group include alkyl groups having 1 or more and 10 or less carbon atoms, such as a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a 1-adamantyl group, and a 2-adamantyl group.

[0029] The aryl group is preferably an aryl group having 6 or more and 18 or less carbon atoms, such as a phenyl group, naphthyl group, indenyl group, biphenyl group, terphenyl group, fluorenyl group, phenanthryl group, or triphenylenyl group.

[0030] The heteroaryl group is preferably a heteroaryl group having 3 or more and 15 or less carbon atoms, and examples thereof include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, and an isoquinolyl group.

[0031] In the substituent Z of R1 to R8, Ar1, Ar2, X1 and X2, examples of the substituent that the alkyl group, alkoxy group, amino group, aryl group, heteroaryl group or aryloxy group may further have include, but are not limited to, alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group and tertiary butyl group; aralkyl groups such as benzyl group; aryl groups such as phenyl group and biphenyl group; amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group and ditolylamino group; alkoxy groups such as methoxy group, ethoxy group and propoxy group; aryloxy groups such as phenoxy group; halogen atoms such as fluorine, chlorine, bromine and iodine; thienyl group; and thiol group.

[0032] Next, a method for synthesizing the organic compound according to this embodiment will be described. For example, the organic compound according to this embodiment can be synthesized by synthesizing a compound represented by general formula [1-1] according to synthesis route 1 shown below, or a compound represented by general formula [1-2] according to synthesis route 2 shown below.

[0033] [ka]

[0034] [ka]

[0035] Here, by appropriately changing G1 to G6, compounds represented by general formulas [1-1] and [1-2] can be obtained. Details of the synthesis method will be explained in the Examples.

[0036] Next, the organic compound according to this embodiment has the following characteristics, and therefore is a compound that has high luminous efficiency, high color purity, and deep HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) levels (far from the vacuum level), making it stable against oxidation. Furthermore, by using the organic compound according to this embodiment, it is possible to provide an organic light-emitting device that is excellent in color purity, luminous efficiency, and device durability. (1) The emission wavelength of the basic structure itself is in the blue region, the oscillator strength is high, and the luminous efficiency is high. (2) Because it has a low LUMO level, it is highly stable against oxygen and has high durability.

[0037] The properties of the basic skeleton of the organic compound according to this embodiment will be explained below with reference to comparative compounds having structures similar to those of the organic compound according to this embodiment. Specifically, the comparative compounds are 1-b, which is the basic skeleton of the comparative compound 1-a described in Patent Document 1, and exemplary compounds A1 and B1 of this embodiment.

[0038] [ka]

[0039] (1) The organic compounds having a fused ring-containing diazaborole derivative as the basic skeleton exhibit high-efficiency blue light emission. In inventing the organic compounds represented by the general formulas [1-1] and [1-2], the inventors focused on the basic skeleton itself.

[0040] First, in order to emit blue light with good color purity, the basic skeleton itself must be in a blue region with high color purity. In this embodiment, the desired emission wavelength region is a blue region with high color purity, specifically, when the emission intensity of the maximum emission wavelength in a dilute solution is taken as 1.0, the intensity ratio at 460 nm is 0.3 or more. The basic skeleton of this embodiment is a skeleton suitable for emitting the desired blue light.

[0041] Table 1 shows a comparison of the wavelength of S1 (lowest singlet excited state) calculated by molecular orbital calculation and the emission spectrum in a dilute toluene solution using exemplary compounds A1 and B1 according to this embodiment and comparative compounds 1-a and 1-b. Specifically, after measuring the emission spectrum, the emission intensity at 460 nm was compared when the maximum emission intensity was set to 1.0. The emission wavelength was measured by photoluminescence measurement of a dilute toluene solution at room temperature with an excitation wavelength of 350 nm using a Hitachi F-4500.

[0042] [Table 1]

[0043] Table 1 shows that the fused ring-containing diazaborole derivative of this embodiment has a longer S1 wavelength than the comparative compounds 1-a and 1-b. Furthermore, when the PL intensity at 460 nm, which is the wavelength required for blue light emission with high color purity, was compared, the comparative compounds 1-a and 1-b had a shorter emission wavelength and were therefore <0.1, whereas the fused ring-containing diazaborole derivative of this embodiment was confirmed to be 0.3 or higher. In other words, the compound of this embodiment has a longer emission wavelength and exhibits highly efficient emission in the blue region with high color purity.

[0044] Thus, it was found that the unique effect of fused ring-containing diazaborole derivatives is that they exhibit high color purity and high efficiency blue light emission. The above HOMO and LUMO electron orbital distributions, as well as the S1 and T1 energies, were visualized using molecular orbital calculations. The molecular orbital calculation method used was the density functional theory (DFT), which is currently widely used. The functional used was B3LYP, and the basis set was 6-31G. *It is also a smooth-flowing waveguide called Gaussian09(Gaussian09, RevisionC.01,MJFrisch,GWTrucks,HBSchlegel,GEScuse ria, MARobb,JRCheeseman,G.Scalmani,V.Barone,B.Mennucci,GAPetersson,H.Nakatsuji,M.Caricato,X.Li,HPHra tchian, AFIzmaylov, J. Bloino, G. Zheng, JLSonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishi da,T.Nakajima,Y.Honda,O.Kitao,H.Nakai,T.Vreven,JAMontgomery,Jr.,JEPeralta,F.Ogliaro,M.Bearpark,JJHe yd, E. Brothers, KNKudin, VNS Taroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, JCBurant ,SSIyengar,J.Tomasi,M.Cossi,N.Rega,JMMillam,M.Klene,JEKnox,JBCross,V.Bakken,C.Adamo,J.Jaramillo,R.G omperts,REStratmann,O.Yazyev,AJAustin,R.Cammi,C.Pomelli,JWOchterski,RLMartin,K.Morokuma,VGZakrzews ki,GAVoth,P.Salvador,JJDannenberg,S.Dapprich,ADDaniels,O.Farkas,JBForesman,JVOrtiz,JCioslowski,and DJFox,Gaussian,Inc.,Wallingford CT,2010.) In addition, a scientifically-defined scientific study was conducted.

[0045] (2) Because it has a low LUMO, it is highly stable against oxygen and has high durability. In organic semiconductors, for compounds with similar band gaps, the lower the HOMO-LUMO level (the farther from the vacuum level), the higher the stability against oxygen. Therefore, lowering the LUMO energy level increases the stability against oxygen, improving the durability of the compound itself and the durability of the organic light-emitting device. Therefore, the inventors focused on the LUMO. Table 2 shows a comparison of the LUMO levels by molecular orbital calculation using example compounds A1 and B1 according to this embodiment and comparative compounds 1-a and 1-b.

[0046] [Table 2]

[0047] From Table 2, it was found that, compared with the comparative compounds 1-b and 1-a, the fused-ring-containing diazaborole derivative of this embodiment has a feature that the LUMO orbital distribution extends not only in the long axis direction of the molecule but also throughout the molecule, resulting in an extended conjugation length and a low LUMO level (far from the vacuum level). That is, it was found that a unique effect of the fused-ring-containing diazaborole derivative is that it has a low LUMO level, which results in high stability against oxygen and high device durability.

[0048] The LUMO level is significantly affected by the electron-withdrawing boron atom. The higher the electron-withdrawing property, the lower the LUMO level. Therefore, the diazaborole derivative of the present invention, in which the electron-withdrawing property of the boron atom in the basic skeleton is conjugated with the orbital of the entire molecule, has a lower LUMO level than the comparative compounds 1-a and 1-b. As described above, it was found that the condensed ring-containing diazaborole derivative has a specific effect of having a low LUMO level, which increases the stability against oxygen and improves the durability of the device.

[0049] As described above, the organic compound according to this embodiment is a compound having the properties (1) and (2) described above, and therefore exhibits high-color purity, highly efficient blue light emission, and is a compound with a high reduction potential and chemical stability compared to comparative compounds. Therefore, by using the organic compound according to this embodiment, an organic light-emitting device excellent in color purity, luminous efficiency, and device durability can be obtained.

[0050] Preferred structures of the organic compounds represented by the general formulas [1-1] and [1-2] are shown in the following [1] to

[11] . [1] An organic compound represented by either of the following general formulas [2-1] and [2-2], which has a structure in which R4 and Ar1 are bonded to each other in the general formulas [1-1] and [1-2].

[0051] [ka]

[0052] [2] It is represented by either of the following general formulas [3-1] and [3-2], and in the general formulas [1-1] and [1-2], Ar1 and Ar2 are both organic compounds having six-membered rings.

[0053] [ka]

[0054] Y1 to Y9 each independently represent a hydrogen atom or a carbon atom or nitrogen atom having a substituent W1, which constitutes a ring, and when adjacent elements are carbon atoms, these carbon atoms may further form a ring. The substituent W1 is selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a cyano group, a silyl group, and deuterium.

[0055] [3] An organic compound represented by either of the following general formulas [4-1] and [4-2], wherein Ar1 and Ar2 in the general formulas [2-1] and [2-2] of the above [1] are 6-membered rings.

[0056] [ka]

[0057] Y2 to Y9 each independently represent a hydrogen atom or a carbon atom or nitrogen atom which has a substituent W2 and forms a ring, and when the adjacent elements are carbon atoms, these carbon atoms may further form a ring. The substituent W2 is independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a cyano group, a silyl group, and deuterium.

[0058] (4) An organic compound represented by either of the following general formulas [5-1] and [5-2], in which Ar1 is a five-membered ring and Ar2 is a six-membered ring in the general formulas [1-1] and [1-2].

[0059] [ka]

[0060] Y6 to Y9 each independently represent a hydrogen atom or a carbon atom or nitrogen atom which has a substituent W3 and constitutes a ring. Y 10 or Y 13 each represents a hydrogen atom or a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom which has a substituent Q1 and constitutes a ring; Y 10 or Y 13 One of the atoms is a nitrogen atom, an oxygen atom, or a sulfur atom. Y6~Y 13 When the adjacent elements are carbon atoms, these carbon atoms may further form a ring. The substituents W3 and Q1 are each independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a cyano group, a silyl group, and deuterium.

[0061] [5] An organic compound represented by either of the following general formulas [6-1] and [6-2], wherein Ar1 and Ar2 in the general formulas [1-1] and [1-2] are both five-membered rings.

[0062] [ka]

[0063] Y 10 or Y 16 each independently represents a hydrogen atom or a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom which has a substituent Q2 and constitutes a ring; Y 10 or Y 13 One of the following and Y 14 or Y 16 One of the atoms is a nitrogen atom, an oxygen atom, or a sulfur atom. Y 10 or Y 16 When the adjacent elements are carbon atoms, these carbon atoms may further form a ring.

[0064] The substituents Q2 are each independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a cyano group, a silyl group, and deuterium.

[0065] [6] An organic compound represented by the following general formula [7], in which X1 and X2 in the general formula [3-1] of the above [2] are both sulfur atoms.

[0066] [ka]

[0067] [7] An organic compound represented by the following general formula [8], in which X1 and X2 in the general formula [3-1] of the above [2] are both oxygen atoms.

[0068] [ka]

[0069] [8] An organic compound represented by the following general formula [9], in which X1 in the general formula [3-1] of the above [2] is an oxygen atom and X2 is a nitrogen atom having a substituent Z1.

[0070] [ka]

[0071] The substituent Z1 is selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a deuterium atom.

[0072] [9] An organic compound represented by the following general formula

[10] , in which X1 in the general formula [3-2] of the above [2] is a sulfur atom.

[0073] [ka]

[0074]

[10] An organic compound represented by the following general formula

[11] , in which X1 in the general formula [3-2] of the above [2] is an oxygen atom.

[0075] [ka]

[0076]

[11] An organic compound represented by the following general formula

[12] , in which X1 in the general formula [3-2] of the above [2] is a nitrogen atom having a substituent Z2.

[0077] [ka]

[0078] The substituent Z2 is selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and deuterium.

[0079] In the preferred organic compounds of [1] to

[11] above, in the substituents W1, W2, W3, Q1, Q2, Z1, and Z2, examples of the substituent that may be further substituted by the alkyl group, alkoxy group, amino group, aryl group, aryloxy group, and heteroaryl group include, but are not limited to, alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, and tertiary butyl group; aralkyl groups such as benzyl group; aryl groups such as phenyl group and biphenyl group; amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, and ditolylamino group; alkoxy groups such as methoxy group, ethoxy group, and propoxy group; aryloxy groups such as phenoxy group; halogen atoms such as fluorine, chlorine, bromine, and iodine; thienyl group; and thiol group.

[0080] Specific examples of the organic compound according to this embodiment are shown below, but this embodiment is not limited to these.

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] [ka]

[0088] Among the above exemplary compounds, compounds belonging to Group A are compounds of formula [1-1] and formula [1-2] in which the substituents Ar1 and Ar2 substituted on the basic skeleton have aryl groups such as phenyl groups, biphenyl groups, naphthyl groups, etc., and divalent linking groups derived from these substituents. Compounds belonging to Group A emit blue light with a shorter wavelength and exhibit higher luminous intensity, even among the compounds according to this embodiment. That is, when used in an emitting layer, compounds belonging to Group A emit blue light with higher color purity and exhibit high luminous efficiency.

[0089] Among the above exemplary compounds, compounds belonging to Group B are compounds of formula [1-1] and formula [1-2] in which the substituents Ar1 and Ar2 substituted on the basic skeleton have aryl groups such as phenyl groups, biphenyl groups, naphthyl groups, etc., and divalent linking groups derived from these substituents, and further, Ar1 forms a ring with R4 of formula [1-1] and [1-2] as a single bond. Group B is a compound group that, due to the increased number of fused ring structures, has increased thermal stability and high reducing properties, making it possible to finely adjust blue light emission and reduction potential.

[0090] Among the above exemplary compounds, the compounds belonging to Group C are compounds of formula [1-1] and formula [1-2] in which the substituents Ar1 and Ar2 substituted on the basic skeleton have heteroaryl groups such as pyridyl, pyrimidyl, and quinolyl groups, and divalent linking groups derived from these substituents. These heteroaryl groups have the properties of electron-withdrawing groups, and therefore can have higher electron-accepting properties and can also emit blue light with high color purity.

[0091] Among the above exemplary compounds, those belonging to group D have a substituent Ar1 but Heteroaryl groups such as benzofuranyl, dibenzofuranyl, benzothienyl, and dibenzothiophenyl is This compound has a lower electron-accepting property than the substituents in group C, but its Tg improves with increasing molecular weight, and it combines high heat resistance with blue light emission with good color purity.

[0092] The organic compound according to this embodiment is a compound that exhibits high efficiency and is suitable for blue light emission, and has high chemical stability. Therefore, by using the organic compound according to this embodiment as a constituent material of an organic light-emitting device, an organic light-emitting device having good light-emitting properties and excellent durability can be obtained.

[0093] <Organic light-emitting element> Next, the organic light-emitting device of this embodiment will be described. The organic light-emitting device of this embodiment has at least a pair of electrodes, an anode and a cathode, and an organic compound layer disposed between these electrodes. In the organic light-emitting device of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has a light-emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, etc. Furthermore, the light-emitting layer may be a single layer or a laminate consisting of multiple layers.

[0094] In the organic light-emitting device of this embodiment, at least one of the organic compound layers contains the organic compound of this embodiment. Specifically, the organic compound of this embodiment is contained in any of the above-mentioned light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, hole / exciton blocking layer, electron transport layer, electron injection layer, etc. The organic compound of this embodiment is preferably contained in the light-emitting layer.

[0095] In the organic light-emitting device of this embodiment, when the organic compound according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer consisting solely of the organic compound according to this embodiment, or may be a layer consisting of the organic compound according to this embodiment and other compounds. Here, when the light-emitting layer is a layer consisting of the organic compound according to this embodiment and other compounds, the organic compound according to this embodiment may be used as a host or a guest of the light-emitting layer. It may also be used as an assist material that can be contained in the light-emitting layer. Here, the host is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. Furthermore, the guest is a compound that is smaller in mass ratio than the host among the compounds constituting the light-emitting layer and is responsible for the main emission of light. Furthermore, the assist material is a compound that is smaller in mass ratio than the host among the compounds constituting the light-emitting layer and assists the emission of the guest. The assist material is also called a second host.

[0096] When the organic compound according to this embodiment is used as a guest in the light-emitting layer, the concentration of the guest is preferably 0.01% by mass or more and 20% by mass or less, and more preferably 0.1% by mass or more and 5% by mass or less, based on the total mass of the light-emitting layer.

[0097] Furthermore, when the organic compound according to this embodiment is used as a guest in the light-emitting layer, it is preferable to use a material having a higher LUMO level than the organic compound according to this embodiment (a material whose LUMO level is closer to the vacuum level) as the host. This is because using a material having a higher LUMO level than the organic compound according to this embodiment as the host allows the organic compound according to this embodiment to better accept electrons supplied to the host in the light-emitting layer. In particular, the organic compounds represented by the general formulas [1-1] and [1-2] have high electron-accepting properties, i.e., low LUMO levels. Therefore, using a material having a higher LUMO level than the organic compounds represented by the general formulas [1-1] and [1-2] as the host allows the organic compound according to this embodiment to better accept electrons supplied to the host in the light-emitting layer.

[0098] The present inventors have conducted various studies and found that when the organic compound according to this embodiment is used as a host or guest in the light-emitting layer, particularly as a guest in the light-emitting layer, a device exhibiting high efficiency and high luminance light output and extremely high durability can be obtained. This light-emitting layer may be a single layer or multiple layers, and it is also possible to mix the blue light emitted by this embodiment with a light-emitting material having another emission color. "Multiple layers" refers to a state in which a first light-emitting layer and a second light-emitting layer are stacked. In this case, the emission color of the organic light-emitting device is not limited to blue. More specifically, it may be white or a neutral color. In the case of white, the second light-emitting layer emits a color other than blue, i.e., red or green. Furthermore, the film is formed by vapor deposition or coating. Details of this will be explained in detail in the examples below.

[0099] The organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer that constitutes the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not limited to blue. More specifically, it may be white or a neutral color.

[0100] In addition to the organic compound according to this embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. may also be used together as needed. Examples of these compounds are listed below.

[0101] As the hole injection and transport material, a material with high hole mobility is preferred so that holes can be easily injected from the anode and the injected holes can be transported to the light-emitting layer. Furthermore, a material with a high glass transition temperature is preferred to reduce deterioration of film quality, such as crystallization, in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole injection and transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above-mentioned hole injection and transport materials are also suitable for use in electron blocking layers. Specific examples of compounds that can be used as hole injection and transport materials are listed below, but the present invention is not limited to these.

[0102] [ka]

[0103] Examples of light-emitting materials that are primarily involved in light-emitting function include organic compounds represented by general formulas [1-1] and [1-2], as well as fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Specific examples of compounds that can be used as light-emitting materials are listed below, but of course, they are not limited to these.

[0104] [ka]

[0105] Examples of the light-emitting layer host or light-emitting assist material contained in the light-emitting layer include aromatic hydrocarbon compounds or derivatives thereof, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, and organic beryllium complexes. Specific examples of compounds used as the light-emitting layer host or light-emitting assist material contained in the light-emitting layer are shown below, but the present invention is not limited to these.

[0106] [ka]

[0107] The electron transport material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected taking into consideration the balance with the hole mobility of the hole transport material. Examples of materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transport materials are also suitable for use in hole-blocking layers. Specific examples of compounds used as electron transport materials are shown below, but of course, the present invention is not limited to these.

[0108] [ka]

[0109] [Configuration of organic light-emitting element] The organic light-emitting element is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate. A protective layer, a color filter, a microlens, etc. may be provided on the cathode. When a color filter is provided, a planarizing layer may be provided between the protective layer. The planarizing layer may be made of acrylic resin or the like. The same applies when a planarizing layer is provided between the color filter and the microlens.

[0110] [substrate] Examples of the substrate include quartz, glass, a silicon wafer, a resin, and a metal. Furthermore, the substrate may be provided with a switching element such as a transistor and wiring, and an insulating layer thereon. Any material can be used for the insulating layer, as long as it allows for the formation of a contact hole so that wiring can be formed between the first electrode and the insulating layer, and ensures insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0111] [electrode] A pair of electrodes can be used. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. It can also be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0112] The anode material should have as high a work function as possible. Examples include simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, mixtures containing these metals, alloys of these metals, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and zinc indium oxide. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0113] These electrode materials may be used alone or in combination of two or more. The anode may be composed of one layer or multiple layers.

[0114] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. The above materials can also function as a reflective film without functioning as an electrode. When used as a transparent electrode, transparent conductive oxide layers such as indium tin oxide (ITO) and indium zinc oxide can be used, but are not limited to these. Photolithography techniques can be used to form the electrode.

[0115] On the other hand, materials with a low work function are preferred for the cathode. Examples include alkali metals such as lithium, alkaline earth metals such as calcium, and metals such as aluminum, titanium, manganese, silver, lead, and chromium, as well as mixtures containing these metals. Alternatively, alloys combining these metals can be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, and zinc-silver can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials can be used alone or in combination. The cathode can have either a single-layer or multi-layer structure. Among these, silver is preferred, and a silver alloy is even more preferred to reduce silver aggregation. The alloy ratio is not critical as long as silver aggregation can be reduced. For example, the silver:other metal ratio can be 1:1, 3:1, or the like.

[0116] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but DC and AC sputtering methods are more preferred because they provide good film coverage and make it easier to reduce resistance.

[0117] [Organic compound layer] The organic compound layer may be formed as a single layer or as multiple layers. When multiple layers are included, they may be called hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, or electron injection layer depending on their functions. The organic compound layer is mainly composed of organic compounds but may also contain inorganic atoms or inorganic compounds. For example, the organic compound layer may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, or the like. The organic compound layer may be disposed between the first electrode and the second electrode, or may be disposed in contact with the first electrode and the second electrode.

[0118] [Protective layer] A protective layer may be provided on the cathode. For example, by adhering glass with a moisture absorbent on the cathode, the intrusion of water and other contaminants into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the intrusion of water and other contaminants into the organic compound layer. For example, after forming the cathode, the cathode may be transferred to another chamber without breaking the vacuum, and a 2 μm-thick silicon nitride film may be formed by CVD to serve as a protective layer. A protective layer may be provided using atomic layer deposition (ALD) after the CVD film formation. The material of the film formed by ALD is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed on the film formed by ALD by CVD. The film formed by ALD may have a thickness smaller than that of the film formed by CVD. Specifically, the thickness may be 50% or less, or even 10% or less.

[0119] [Color Filter] A color filter may be provided on the protective layer. For example, a color filter taking into consideration the size of the organic light-emitting element may be provided on a separate substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using photolithography technology. The color filter may be made of a polymer.

[0120] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing unevenness of the underlying layer. It may also be called a material resin layer without limiting its purpose. The planarization layer may be composed of an organic compound, and may be low molecular weight or high molecular weight, but is preferably high molecular weight. The planarization layers may be provided above and below the color filter, and may be made of the same or different materials. Specific examples include polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0121] [Microlens] The organic light-emitting device may have an optical component such as a microlens on its light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be used to increase the amount of light extracted from the organic light-emitting device and to control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be determined in the same way in any cross-sectional view. In other words, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the semicircle is the vertex of the microlens.

[0122] It is also possible to define the midpoint of a microlens. In the cross section of the microlens, a line segment is imagined from the point where an arc shape ends to the point where another arc shape ends, and the midpoint of this line segment can be called the midpoint of the microlens. The cross section for determining the vertex and midpoint may be a cross section perpendicular to the insulating layer.

[0123] [Counter substrate] An opposing substrate may be provided on the planarization layer. The opposing substrate is called an opposing substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the opposing substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is defined as a first substrate, the opposing substrate may be a second substrate.

[0124] [Organic compound layer] The organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light emitting device according to this embodiment are formed by the method shown below.

[0125] The organic compound layer can be formed by dry processes such as vacuum deposition, ionization deposition, sputtering, and plasma. Instead of a dry process, a wet process can be used in which the compound is dissolved in an appropriate solvent and a layer is formed by a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.). Forming a layer by vacuum deposition or solution coating, etc., makes it less likely to crystallize and provides excellent stability over time. When forming a film by a coating method, a film can also be formed by combining it with an appropriate binder resin.

[0126] Examples of the binder resin include, but are not limited to, polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin. These binder resins may be used singly or in combination as homopolymers or copolymers. If necessary, known additives such as plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.

[0127] [Pixel circuit] The light-emitting device may have a pixel circuit connected to the light-emitting element. The pixel circuit may be an active matrix type that controls the emission of the first light-emitting element and the second light-emitting element independently. The active matrix type circuit may be voltage-programmed or current-programmed. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission brightness of the light-emitting element, a transistor that controls the emission timing, a capacitor that holds the gate voltage of the transistor that controls the emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0128] The light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of a transistor constituting the pixel circuit may be smaller than the mobility of a transistor constituting the display control circuit. The slope of the current-voltage characteristics of the transistor constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistor constituting the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics. The transistor constituting the pixel circuit is a transistor connected to a light-emitting element, such as a first light-emitting element.

[0129] [Pixels] An organic light emitting device having an organic light emitting element may have a plurality of pixels, each of which has sub-pixels that emit different colors, for example, RGB light emitting colors.

[0130] A pixel has an area, also called a pixel opening, that emits light. This area is the same as the first area. The pixel opening may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc. The distance between subpixels may be 10 μm or less, more specifically, it may be 8 μm, 7.4 μm, or 6.4 μm.

[0131] The pixels may be arranged in a known manner in a plan view. For example, they may be in a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in a plan view may be any known shape. For example, they may be rectangular, quadrilaterals such as diamonds, or hexagons. Of course, a shape that is close to a rectangle, rather than an exact shape, is included in the rectangle. The shape of the subpixels and the pixel arrangement may be used in combination.

[0132] <Applications of organic light-emitting devices> The organic light-emitting device according to this embodiment can be used as a component of a display device or a lighting device, and can also be used as an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, or a light-emitting device having a white light source and a color filter.

[0133] The display device may be an image information processing device that has an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., has an information processing unit that processes the input information, and displays the input image on a display unit. The display device may have a plurality of pixels, at least one of which may have the organic light-emitting element of this embodiment and a transistor connected to the organic light-emitting element.

[0134] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of this touch panel function may be an infrared method, a capacitance method, a resistive film method, or an electromagnetic induction method, and is not particularly limited. The display device may also be used in the display unit of a multifunction printer.

[0135] Next, a display device according to this embodiment will be described with reference to the drawings. Fig. 1 is a cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin-film transistor (TFT).

[0136] FIG. 1(a) shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel includes sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The emitted colors may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the sub-pixels may be selectively transmitted or color-converted using a color filter or the like. Each sub-pixel 10 includes a reflective electrode serving as a first electrode 2 on an interlayer insulating layer 1, an insulating layer 3 covering the edge of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode serving as a second electrode 5, a protective layer 6, and a color filter 7.

[0137] A transistor and a capacitor element may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

[0138] The insulating layer 3 is also called a bank or a pixel separation film. It covers the edges of the first electrode 2 and is disposed to surround the first electrode 2. The portion where the insulating layer 3 is not disposed contacts the organic compound layer 4 and becomes a light-emitting region.

[0139] The organic compound layer 4 includes a hole injection layer 41 , a hole transport layer 42 , a first light-emitting layer 43 , a second light-emitting layer 44 , and an electron transport layer 45 .

[0140] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0141] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 is illustrated as being one layer, it may be multiple layers, and each layer may be an inorganic compound layer and an organic compound layer.

[0142] The color filters 7 are divided into 7R, 7G, and 7B depending on their colors. The color filters 7 may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters 7. The color filters 7 may be formed on the protective layer 6. Alternatively, the color filters 7 may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0143] The display device 100 in FIG. 1(b) has an organic light-emitting element 26 and a TFT 18 as an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided with an insulating layer 12 on top of it. An active element such as the TFT 18 is disposed on the insulating layer 12, and a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element are disposed on top of it. The TFT 18 also comprises a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on top of the TFT 18. An anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film 19.

[0144] The electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the embodiment shown in Fig. 1(b). In other words, it is sufficient that either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT 18. TFT stands for thin film transistor.

[0145] 1(b), the organic compound layer 22 is illustrated as a single layer, but may be a multi-layer organic compound layer 22. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26.

[0146] Although the display device 100 in FIG. 1(b) uses transistors as switching elements, other switching elements may be used instead.

[0147] The transistors used in the display device 100 of Fig. 1(b) are not limited to transistors using single-crystal silicon wafers, but may also be thin-film transistors having an active layer on an insulating surface of a substrate. Examples of active layers include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0148] The transistors included in the display device 100 of Fig. 1(b) may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the substrate itself, such as a Si substrate, is processed to form the transistors. In other words, having a transistor within a substrate can be seen as the substrate and the transistor being integrally formed.

[0149] The organic light-emitting element according to this embodiment has its emission brightness controlled by a TFT, which is an example of a switching element. By providing multiple organic light-emitting elements on a surface, an image can be displayed based on the emission brightness of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor formed from low-temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also be referred to as "inside the substrate." Whether to provide a transistor within the substrate or to use a TFT is determined by the size of the display unit. For example, for a display size of about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0150] FIG. 2(a) is a schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 includes an organic light-emitting element according to this embodiment. The developing unit 31 includes toner and the like. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0151] 2(b) and 2(c) are schematic diagrams showing an exposure light source 28, each illustrating a plurality of light-emitting units 36, each of which is an organic light-emitting element according to this embodiment, arranged on a long substrate. Arrow 37 indicates the direction parallel to the axis of the photoconductor 27, representing the column direction in which the light-emitting units 36 are arranged. This column direction is the same as the axis direction about which the photoconductor 27 rotates. This direction can also be referred to as the long axis direction of the photoconductor 27. FIG. 2(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoconductor 27. FIG. 2(c) shows a different configuration from FIG. 2(b), in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are arranged at different positions in the row direction. The first column includes multiple light-emitting units 36 spaced apart. The second column includes light-emitting units 36 at positions corresponding to the spacing between the light-emitting units 36 in the first column. That is, the light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in Fig. 2(c) can also be described as a grid-like arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0152] 3 is a schematic diagram illustrating an example of a display device according to this embodiment. The display device 1000 may include a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The touch panel 1003 and the display panel 1005 are connected by flexible printed circuits FPCs 1002 and 1004. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position even if the display device is a portable device.

[0153] The display device according to this embodiment may have color filters having red, green, and blue colors, which may be arranged in a delta arrangement.

[0154] The display device according to the present embodiment may be used as a display unit of a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include a mobile phone such as a smartphone, a tablet, and a head-mounted display.

[0155] The display device according to this embodiment may be used as a display unit of an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0156] 4A is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may include a display device according to this embodiment. In this case, the display device may display not only an image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject is moving, the possibility that the subject will be blocked by an obstruction, and the like.

[0157] Since the optimum timing for capturing an image is very short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment. This is because the organic light-emitting element has a fast response speed. A display device using the organic light-emitting element can be used more preferably than a liquid crystal display device, which requires a high display speed.

[0158] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses, which form an image on an imaging element housed in a housing 1104. The focus of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may also be called a photoelectric conversion device. Instead of sequentially capturing images, the photoelectric conversion device can include an imaging method that detects the difference from the previous image, or a method of cutting out an image from a constantly recorded image, etc.

[0159] FIG. 4(b) is a schematic diagram illustrating an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit 1202 may be a biometric recognition unit that recognizes a fingerprint to perform operations such as unlocking. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an image sensor. An image captured by the camera function is displayed on the display unit 1201. Examples of the electronic device 1200 include a smartphone and a laptop computer.

[0160] FIG. 5 is a schematic diagram illustrating an example of a display device according to this embodiment. FIG. 5(a) illustrates a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The display unit 1302 may use a light-emitting element according to this embodiment. The display device 1300 includes the frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. 5(a). The lower side of the frame 1301 may also serve as the base. The frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0161] FIG. 5(b) is a schematic diagram illustrating another example of a display device according to this embodiment. The display device 1310 in FIG. 5(b) is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include light-emitting elements according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single, seamless display unit. The first display unit 1311 and the second display unit 1312 can be separated by the bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may display a single image.

[0162] FIG. 6(a) is a schematic diagram illustrating an example of a lighting device according to this embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusion unit 1405. The light source 1402 may include an organic light-emitting element according to this embodiment. The optical filter 1404 may be a filter that improves the color rendering of the light source. The light diffusion unit 1405 can effectively diffuse light from the light source, such as for illumination, and deliver the light over a wide area. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the lighting. If necessary, a cover may be provided on the outermost surface.

[0163] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white, daylight white, or any other color from blue to red. It may have a dimming circuit that dims these colors. The lighting device may have the organic light-emitting element of this embodiment and a power supply circuit connected thereto. The power supply circuit is a circuit that converts AC voltage to DC voltage. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device may have a color filter.

[0164] The lighting device according to this embodiment may also include a heat dissipation unit, which dissipates heat from within the device to the outside, and may be made of a material such as a metal with a high specific heat capacity or liquid silicon.

[0165] 6(b) is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has tail lamps, which are an example of lighting fixtures. The automobile 1500 has tail lamps 1501, and may be configured to turn on the tail lamps when braking or the like is performed.

[0166] The tail lamp 1501 may include an organic light-emitting element according to this embodiment. The tail lamp 1501 may include a protective member for protecting the organic light-emitting element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0167] The automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display as long as it is not a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials of the electrodes and the like of the organic light-emitting element are made of transparent materials.

[0168] The moving body according to this embodiment may be a ship, an aircraft, a drone, or the like. The moving body may have a body and a lighting device provided on the body. The lighting device may emit light to indicate the position of the body. The lighting device has the organic light-emitting element according to this embodiment.

[0169] An application example of the display device of each of the above-described embodiments will be described with reference to Fig. 7. The display device can be applied to a system that can be attached as a wearable device, such as smart glasses, an HMD, or a smart contact lens. The image capturing and display device used in such an application example includes an image capturing device capable of photoelectrically converting visible light and a display device capable of emitting visible light.

[0170] Fig. 7(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using Fig. 7(a), glasses 1600 (smart glasses) according to one application example will be described. An imaging device 1602 such as a CMOS sensor or SPAD is provided on the front side of a lens 1601 of the glasses 1600. In addition, a display device according to each of the above-mentioned embodiments is provided on the back side of the lens 1601.

[0171] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the image capture device 1602 and the display device. The control device 1603 also controls the operations of the image capture device 1602 and the display device. The lens 1601 is formed with an optical system for focusing light onto the image capture device 1602.

[0172] FIG. 7(b) is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 7(b), glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 have a control device 1612, which is equipped with an imaging device corresponding to the imaging device 1602 in FIG. 7(a) and a display device. A lens 1611 is formed with an optical system for projecting light emitted from the imaging device in the control device 1612 and the display device, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and also controls the operation of the imaging device and the display device.

[0173] The control device 1612 may include a gaze detection unit that detects the wearer's gaze. The gaze detection may use infrared light. The infrared light emitter emits infrared light toward the eyeball of the user gazing at the display image. An imaging unit with a light-receiving element detects the reflected infrared light from the eyeball, thereby obtaining a captured image of the eyeball. A reduction unit that reduces light from the infrared light emitter to the display unit in a planar view reduces degradation of image quality. The user's gaze toward the displayed image is detected from the captured image of the eyeball obtained by capturing infrared light. Any known method can be applied to gaze detection using the captured image of the eyeball. As an example, a gaze detection method based on a Purkinje image formed by reflection of irradiated light on the cornea can be used. More specifically, gaze detection processing based on the pupil-corneal reflex method is performed. Using the pupil-corneal reflex method, a gaze vector representing the orientation (rotation angle) of the eyeball is calculated based on the image of the pupil and the Purkinje image included in the captured image of the eyeball, thereby detecting the user's gaze.

[0174] A display device according to one embodiment of the present invention may include an imaging device having a light receiving element, and may control the display image of the display device based on user line-of-sight information from the imaging device. Specifically, the display device determines a first field of view area where the user gazes and a second field of view area other than the first field of view area based on the line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. In the display area of ​​the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than that of the first field of view area.

[0175] The display area includes a first display area and a second display area different from the first display area, and a high-priority area is determined from the first display area and the second display area based on line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. The resolution of the high-priority area may be controlled to be higher than the resolution of areas other than the high-priority area. In other words, the resolution of an area with a relatively low priority may be lowered.

[0176] Note that AI may be used to determine the first field of view area or the area with high priority. The AI ​​may be a model configured to estimate the angle of gaze and the distance to an object in the line of sight from the image of the eyeball, using as training data an image of the eyeball and the direction in which the eyeball in the image was actually looking. The AI ​​program may be included in the display device, the imaging device, or an external device. If included in the external device, it is transmitted to the display device via communication.

[0177] When display control is performed based on visual recognition detection, the smart glasses can be preferably applied to smart glasses that further include an imaging device for capturing images of the outside world. The smart glasses can display captured external information in real time.

[0178] As described above, by using a device using the organic light-emitting element according to this embodiment, it is possible to provide a stable display with good image quality even over a long period of time. [Example]

[0179] The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

[0180] [Example 1 (Synthesis of Exemplary Compound A1)] Exemplary compound A1 was synthesized according to the synthesis route shown below.

[0181] [ka]

[0182] (1) Synthesis of compound H3 The following compounds, reagents, and solvents were placed in a 1 L recovery flask. Compound H1: 10.00g (46.7mmol) Compound H2: 10.94g (70.1mmol) Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium): 2.70 g (2.34 mmol) Na2CO3: 9.90g (93.4mmol) Toluene: 500 ml Ethanol: 100ml Water: 100ml Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred at this temperature (90°C) for 5 hours. After the reaction was completed, the solution was extracted with toluene and water, concentrated, purified by silica gel column chromatography (heptane:toluene = 1:10), and then dispersed and washed with methanol to obtain 9.71 g (yield: 85%) of white compound H3.

[0183] (2) Synthesis of compound H4 The following compounds, reagents, and solvents were placed in a 1 L recovery flask. Compound H3: 9.50g (38.8mmol) N-Bromosuccinimide: 7.25 g (40.7 mmol) Acetonitrile: 500 ml The reaction solution was stirred under a nitrogen stream for 2 hours. After the reaction was completed, water was added and the mixture was filtered. The residue was recrystallized from cyclohexane to obtain 10.30 g (yield: 82%) of a white compound H4.

[0184] (3) Synthesis of Compound H5 The following compounds, reagents, and solvents were placed in a 500 ml recovery flask. Compound H4: 5.00g (15.4mmol) Boronic acid trimethyl ester 2.40g (23.1mmol) Tetrahydrofuran: 250 ml Next, the reaction solution was cooled to −78° C. under a nitrogen stream, and the following reagents were added dropwise. n-Butyllithium (1.6M hexane solution) 10.56ml (16.9mmol) Next, the reaction solution was stirred at -78°C for 30 minutes, then slowly warmed to room temperature over about 1 hour, and stirred at room temperature for 1 hour. After the reaction was completed, the solution was cooled to 0°C, and 50 ml of 2 M hydrochloric acid was added and stirred for 30 minutes at 0°C. After that, 200 mL of water was added, and the solution was filtered and washed with water and methanol to obtain 3.11 g (yield: 70%) of white compound H5.

[0185] (4) Synthesis of Compound H7 The following compounds, reagents, and solvents were placed in a 300 ml recovery flask. Compound H5: 3.00g (10.4mmol) Compound H6: 1.71g (10.4mmol) Toluene: 120 ml The reaction solution was then heated to 120°C under a nitrogen stream and stirred for 5 hours under reflux. After the reaction was completed, the solution was concentrated, heptane was added, and the mixture was filtered. Subsequently, the mixture was dispersed and washed with heptane to obtain 2.82 g (yield: 65%) of white compound H7.

[0186] (5) Synthesis of Compound H8 The following compounds, reagents, and solvents were placed in a 300 ml recovery flask. Compound H7: 2.8g (6.72mmol) Pd(OAc)2 (palladium acetate): 75 mg (0.34 mmol) XPhos (2-dicyclohexylsulfosphino-2',4',6'-triisopropylbiphenyl): 320 mg (0.68 mmol) tBuOK (potassium tert-butoxide): 1.13 g (10.8 mmol) Xylene: 140 ml The reaction solution was then heated to 145°C under a nitrogen stream and stirred for 7 hours under reflux. After the reaction was completed, the mixture was filtered. The resulting mixture was purified by silica gel column chromatography (toluene / ethyl acetate = 10 / 1) and then dispersed and washed with toluene to obtain 1.28 g (yield: 50%) of white compound H8.

[0187] (6) Synthesis of Example Compound A1 The following compounds, reagents, and solvents were placed in a 200 ml recovery flask. Compound H8: 1.20g (2.63mmol) Compound H9: 229mg (3.95mmol) Pd(OAc)2: 29 mg (0.13 mmol) Tri-o-tolylphosphine: 79 mg (0.26 mmol) tBuOK: 0.59 g (5.26 mmol) Xylene: 120 ml Next, the reaction solution was heated to 145°C under a nitrogen stream and stirred under reflux for 5 hours. After the reaction was completed, the solution was filtered. The solution was purified by silica gel column chromatography (chlorobenzene) and then recrystallized from toluene to obtain 0.84g (yield: 70%) of white exemplary compound A1.

[0188] The exemplary compound A1 obtained in the above step was subjected to mass spectrometry using a MALDI-TOF-MS (Bruker Autoflex LRF). 28 H 17 The calculated value obtained from BN2S2 was 456, while the measured value (m / z) was 456, which agreed.

[0189] [Examples 2 to 25 (Synthesis of Exemplary Compounds)] As shown in Tables 3 to 7, the exemplary compounds shown in Examples 2 to 25 were synthesized in the same manner as in Example 1, except that compound H1 in Example 1 was replaced with raw material 1, compound H2 with raw material 2, compound H6 with raw material 3, and compound H9 with raw material 4. The actual measured values ​​(m / z) of the mass spectrometry results measured in the same manner as in Example 1 are also shown.

[0190] [Table 3]

[0191] [Table 4]

[0192] [Table 5]

[0193] [Table 6]

[0194] [Table 7]

[0195] [Example 26 (Synthesis of Exemplary Compound B1)] Exemplary compound B1 was synthesized according to the synthesis route shown below.

[0196] [ka]

[0197] (1) Synthesis of compound H8 H8 was synthesized from H1 via five steps by the method shown in Example 1.

[0198] (2) Synthesis of Compound H11 The following compounds, reagents, and solvents were placed in a 200 ml recovery flask. Compound H8: 2.50g (6.57mmol) Compound H10: 2.79g (9.87mmol) Pd(OAc)2: 73 mg (0.33 mmol) Tri-o-tolylphosphine: 200 mg (0.66 mmol) tBuOK: 1.11 g (9.86 mmol) Xylene: 120 ml Next, the reaction solution was heated to 145°C under a nitrogen stream and stirred under reflux for 5 hours. After the reaction was completed, the solution was filtered. The solution was purified by silica gel column chromatography (chlorobenzene) and then recrystallized from toluene to obtain 1.76g (yield: 50%) of white exemplary compound H11.

[0199] (3) Synthesis of Exemplary Compound B1 The following compounds, reagents, and solvents were placed in a 500 ml recovery flask. Compound H11: 1.50g (2.80mmol) Aluminum chloride: 1.12 g (8.40 mmol) Tetralin: 150ml Next, the reaction solution was heated to 180°C under a nitrogen stream and stirred at this temperature (180°C) for 8 hours. After the reaction was completed, 300 ml of methanol was added at room temperature, stirred for 30 minutes, and filtered. The obtained residue was recrystallized from chlorobenzene to obtain 254 mg (yield: 20%) of pale yellow exemplary compound B1. The exemplary compound B1 obtained in the above step was subjected to mass spectrometry using a MALDI-TOF-MS (Bruker Autoflex LRF). 28 H 15 The calculated value obtained from BN2S2 was 454, while the measured value (m / z) was 454, which agreed.

[0200] [Examples 27 to 34 (Synthesis of exemplified compounds)] As shown in Tables 8 and 9, the exemplary compounds shown in Examples 27 to 34 were synthesized in the same manner as in Example 26, except that compound H8 in Example 26 was replaced with raw material 5 and compound H10 was replaced with raw material 6. The actual measured values ​​(m / z) of the mass spectrometry results measured in the same manner as in Example 1 are also shown.

[0201] [Table 8]

[0202] [Table 9]

[0203] [Example 35] In this example, an organic light-emitting element having a bottom-emission structure was fabricated in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed on a substrate.

[0204] First, an ITO film was formed on a glass substrate and then patterned as desired to form an ITO electrode (anode). At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed was used as the ITO substrate in the following process. Next, a 1.33 × 10 -4 Pa(1×10 -6 The organic EL layer and electrode layer shown in Table 10 were successively formed on the ITO substrate by vacuum deposition using resistance heating in a vacuum chamber at 1000 kJ / cm² (Torr). At this time, the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was 3 mm². 2 It was made to be like this.

[0205] [Table 10]

[0206] The device characteristics were measured and evaluated. Blue light emission was obtained with a maximum current efficiency of 12.5 cd / A. Specifically, the current-voltage characteristics were measured using a microcurrent meter 4140B manufactured by Hewlett-Packard, and the luminance was measured using a BM7 manufactured by Topcon. Furthermore, the device was driven at a current density of 20 mA / cm. 2 The time until the luminance degradation rate reached 5% (LT95) was measured, and it was 120 hours. The measurement results are shown in Table 11.

[0207] [Examples 36 to 53, Comparative Example 1] An organic light-emitting device was produced in the same manner as in Example 35, except that the compounds were appropriately changed to those shown in Table 11. The characteristics of the obtained light-emitting device were measured and evaluated in the same manner as in Example 35. The measurement results are shown in Table 11.

[0208] [Table 11]

[0209] As shown in Table 11, Comparative Example 1, which used comparative compound 1-a described in Patent Document 1, had a current efficiency of 7.5 cd / A or less and a 5% degradation lifetime (LT95) of 70 hours or less, which were poor compared to the current efficiency and durability characteristics of the blue light-emitting devices of the Examples. On the other hand, the light-emitting devices of the Examples, which used the organic compound of this embodiment, showed good durability characteristics. This is because the organic compound of this embodiment has a condensed ring-containing diazaborole skeleton, which results in an emission wavelength suitable for blue light emission, a stable molecular structure due to the condensed ring structure, a low LUMO level, and high stability against oxygen.

[0210] [Example 54] An organic light-emitting device was produced in the same manner as in Example 35, except that the compounds shown in Table 12 were appropriately changed.

[0211] [Table 12]

[0212] The resulting light-emitting device emitted good green light. 2 The time until the luminance degradation rate reached 5% (LT95) was measured, and it exceeded 500 hours. The measurement results are shown in Table 13.

[0213] [Examples 55 to 62, Comparative Examples 2 and 3] Organic light-emitting devices were fabricated in the same manner as in Example 35, except for appropriately changing the compounds shown in Table 13. The LT95 of the obtained light-emitting devices was measured in the same manner as in Example 54. The measurement results are shown in Table 13. In Examples 60 to 62, only the first host was used as the host, and the content of the guest in the light-emitting layer was set to be equal to the content of the guest in Examples 55 to 59.

[0214] [Table 13]

[0215] From Table 13, it can be seen that the 5% degradation lifespans of Comparative Examples 2 and 3 are 500 hours or less, indicating poor durability, whereas the 5% degradation lifespans of the light-emitting devices of Examples using the organic compound according to this embodiment are longer than 500 hours, indicating long lifespans. The light-emitting devices using the organic compound according to this embodiment exhibit good durability.

[0216] [Example 63] In this example, an organic light-emitting element having a top-emission structure was fabricated in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a first emitting layer, a second emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed on a substrate.

[0217] A 40 nm thick laminated film of Al and Ti was formed on a glass substrate by sputtering, and then patterned using photolithography to form an anode. At this time, the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was 3 mm2. 2Next, the substrate with the cleaned electrodes and the material were placed in a vacuum deposition device (manufactured by ULVAC), and a 1.3 × 10 -4 Pa(1×10 -6 After evacuating the chamber to a pressure of 1000 Torr, the chamber was subjected to UV / ozone cleaning. After that, each layer was formed according to the layer configuration shown in Table 14, and finally, the chamber was sealed in a nitrogen atmosphere.

[0218] [Table 14]

[0219] The obtained light-emitting device exhibited excellent white light emission. Furthermore, the initial luminance was 1000 cd / m 2 A continuous driving test was carried out at 100 hours, and the luminance deterioration rate after 100 hours was measured in the same manner as in Example 35. The results are shown in Table 15.

[0220] [Examples 64 to 71, Comparative Example 4] An organic light-emitting device was produced in the same manner as in Example 63, except for appropriately changing the compounds shown in Table 15. The characteristics of the obtained light-emitting device were measured and evaluated in the same manner as in Example 63. The measurement results are shown in Table 15.

[0221] [Table 15]

[0222] As can be seen from Table 15, the luminance degradation rate of the light-emitting device using comparative compound 1-a was 55%. This is because when the comparative compound is used as a guest, the LUMO level is high and stability against oxygen is poor.

[0223] On the other hand, the light-emitting devices of the examples using the organic compound of this embodiment exhibited good durability characteristics. This is because the compound of this embodiment has a condensed ring-containing diazaborole skeleton, a low LUMO level, and high stability against oxygen.

[0224] From the above, it has been found that the organic compound according to this embodiment has high luminous efficiency, high color purity, and a deep LUMO level (far from the vacuum level), and is capable of emitting blue light. Therefore, by using the organic compound according to this embodiment, an organic light-emitting device excellent in color purity, luminous efficiency, and durability can be provided. [Explanation of symbols]

[0225] 2: first electrode, 4, 22: organic compound layer, 5: second electrode, 21: anode, 23: cathode, 26: organic light-emitting element, 28: exposure light source, 40: image forming apparatus, 100: display device, 1201, 1302, 1311, 1312: display unit, 1404: optical filter, 1045: light diffusion unit, 1601: lens

Claims

1. An organic compound represented by either of the following general formulas [1-1] and [1-2]: 【Chemistry 1】 In the above formulas [1-1] and [1-2], R 1 ~R 8 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a cyano group, a silyl group, and a deuterium atom, provided that R 4 is Ar 1 may be bonded to form a ring. Ar 1 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. Ar 2 represents a divalent linking group derived from any one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, and a substituted or unsubstituted quinolyl group, and the phenyl group, the biphenyl group, the naphthyl group, the pyridyl group, the pyrimidyl group, and the quinolyl group are bonded to each other through adjacent carbon atoms. X 1 and X 2 are each independently selected from an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, and a nitrogen atom having a substituent Z, and the substituent Z is selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and deuterium.

2. The organic compound described in Claim 1, characterized in that when Ar2 has a substituent, the substituent is either a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or a cyano group.

3. 2. The organic compound according to claim 1, which is represented by either of the following general formulas [2-1] and [2-2]: 【Chemistry 2】

4. 2. The organic compound according to claim 1, which is represented by either of the following general formulas [3-1] and [3-2]: 【Transformation 3】 In the above formulas [3-1] and [3-2], Y 1 to Y5 are each independently a hydrogen atom or a substituent W 1 and represents a carbon atom or a nitrogen atom which constitutes a ring, and when the adjacent elements are carbon atoms, these carbon atoms may further form a ring. All of Y6 to Y9 are carbon atoms, or one or two are nitrogen atoms and the rest are carbon atoms, and when there are two nitrogen atoms, Y6 and Y8 or Y7 and Y9 are nitrogen atoms. The carbon atoms have a hydrogen atom or a substituent P1. When all of Y6 to Y9 are carbon atoms, adjacent carbon atoms may further form a substituted or unsubstituted benzene ring or a substituted or unsubstituted pyridine ring. The substituent W 1 , P1 is selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a cyano group, a silyl group, and deuterium.

5. The organic compound according to claim 3, which is represented by either of the following general formulas [4-1] and [4-2]: 【Chemistry 4】 In the above formulas [4-1] and [4-2], Y 2 to Y5 are each independently a hydrogen atom or a substituent W 2 and represents a carbon atom or a nitrogen atom which constitutes a ring, and when the adjacent elements are carbon atoms, these carbon atoms may further form a ring. All of Y6 to Y9 are carbon atoms, or one or two are nitrogen atoms and the rest are carbon atoms. When there are two nitrogen atoms, Y6 and Y8 or Y7 and Y9 are nitrogen atoms. The carbon atoms have a hydrogen atom or a substituent P2. When all of Y6 to Y9 are carbon atoms, adjacent carbon atoms may further form a substituted or unsubstituted benzene ring or a substituted or unsubstituted pyridine ring. The substituent W 2 P2 is independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a cyano group, a silyl group, and deuterium.

6. 2. The organic compound according to claim 1, which is represented by either of the following general formulas [5-1] and [5-2]: 【Transformation 5】 In the above formulas [5-1] and [5-2], Y 6 or Y 9 are all carbon atoms, or one or two are nitrogen atoms and the rest are carbon atoms, and when there are two nitrogen atoms, Y and Y or Y and Y are nitrogen atoms. The carbon atoms have a hydrogen atom or a substituent W. When Y to Y are all carbon atoms, adjacent carbon atoms may further form a substituted or unsubstituted benzene ring or a substituted or unsubstituted pyridine ring. Y 10 or Y 13 are each a hydrogen atom or a substituent Q 1 represents any one of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom constituting a ring, and Y 10 or Y 13 One of the atoms is a nitrogen atom, an oxygen atom, or a sulfur atom. Y 10 to Y 13 When the adjacent elements are carbon atoms, these carbon atoms may further form a ring. The substituent W 3 , Q 1 are each independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a cyano group, a silyl group, and deuterium.

7. The organic compound according to claim 4, which is represented by the following general formula [7]: 【Transformation 6】

8. The organic compound according to claim 4, which is represented by the following general formula [8]: 【Transformation 7】

9. The organic compound according to claim 4, which is represented by the following general formula [9]: 【Transformation 8】 In the above formula [9], the substituent Z 1 is selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a deuterium atom.

10. The organic compound according to claim 4, which is represented by the following general formula [10]: 【Chemistry 9】

11. The organic compound according to claim 4, which is represented by the following general formula [11]: 【Chemistry 10】

12. The organic compound according to claim 4, which is represented by the following general formula [12]: 【Chemistry 11】 In the above formula [12], the substituent Z 2 is selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and deuterium.

13. an anode and a cathode, an organic compound layer disposed between the anode and the cathode, An organic light-emitting device, wherein at least one of the organic compound layers comprises the organic compound according to claim 1 .

14. The organic light-emitting device according to claim 13 , wherein the layer containing the organic compound is a light-emitting layer.

15. 15. The organic light-emitting device according to claim 13, which emits blue light.

16. 16. The organic light-emitting device according to claim 15, further comprising a second light-emitting layer disposed by stacking the light-emitting layer as a first light-emitting layer, wherein the second light-emitting layer emits light of a color different from the light color emitted by the first light-emitting layer.

17. The organic light-emitting device according to claim 16, which emits white light.

18. A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to claim 13 and a transistor connected to the organic light-emitting element.

19. an optical unit having a plurality of lenses, an image pickup element that receives light that has passed through the optical unit, and a display unit that displays an image picked up by the image pickup element; The photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to claim 13 .

20. 18. An electronic device comprising: a display unit having the organic light-emitting element according to claim 13; a housing in which the display unit is provided; and a communication unit provided in the housing and communicating with an external device.

21. 18. A lighting device comprising: a light source having the organic light-emitting element according to claim 13; and a light diffusion section or an optical filter that transmits light emitted by the light source.

22. A moving body comprising: a lamp having the organic light-emitting element according to any one of claims 13 to 17; and a body on which the lamp is provided.

23. An exposure light source for an electrophotographic image forming apparatus, comprising the organic light-emitting element according to claim 13 .

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