Organic compounds and organic light-emitting elements

Abstract

To provide a blue-light-emitting material with high light emission efficiency and good color purity.SOLUTION: The invention provides an organic compound represented by the general formula [1] in the figure. In the formula, R1 to R8 are each independently selected from the group consisting of a hydrogen atom, alkyl groups, and the like; Ar1 to Ar4 are each independently selected from the group consisting of alkyl groups, aryl groups, and the like; L denotes a substituted or unsubstituted arylene group or the like; X is independently selected from the group consisting of an oxygen atom, a sulfur atom, and the like.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] An organic light-emitting element (hereinafter sometimes referred to as an "organic electroluminescent element" or "organic EL element") is an electronic element having a pair of electrodes and an organic compound layer placed between these electrodes. By injecting electrons and holes from this pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated, and when these excitons return to the ground state, the organic light-emitting element emits light. Recent advances in organic light-emitting elements are remarkable, including low driving voltage, diverse emission wavelengths, fast response, and the ability to make light-emitting devices thinner and lighter. Furthermore, while sRGB and AdobeRGB standards have been used for the color reproduction range in displays, and materials that can reproduce them have been sought after, BT-2020 has recently emerged as a standard that further expands the color reproduction range. Incidentally, there has been a great deal of activity in creating luminescent organic compounds to date. This is because creating compounds with excellent luminescence properties is important in 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] International Publication No. 2010 / 108579 [Overview of the project] [Problems that the invention aims to solve]

[0005] Patent Document 1 discloses a synthesis example of Compound 1-a, but there is no suggestion regarding luminous efficiency or emission color. Further, considering the blue color reproduction range corresponding to the sRGB, Adobe RGB, and even BT2020 standards, further improvement in the color purity of blue emission is desired. For organic light-emitting devices using these compounds, further improvement in color purity or durability characteristics is desired. The present invention has been made in view of the above problems, and an object thereof is to provide a blue light-emitting material having high luminous efficiency and good color purity. Another object of the present invention is to provide an organic light-emitting device excellent in color purity and luminous efficiency.

Means for Solving the Problems

[0006] The organic compound of the present invention is characterized by being represented by the following general formula [1].

[0007]

Chemical formula

Advantages of the Invention

[0008] The organic compound according to the present invention is a blue light-emitting material with good color purity and high luminous efficiency. Therefore, it is possible to provide an organic light-emitting device having excellent color purity and luminous efficiency.

Brief Description of the Drawings

[0009] [Figure 1] It is a diagram showing the value of LUMO and the electron orbits of LUMO and HOMO by molecular orbital calculation. [Figure 2] (a) It is a schematic cross-sectional view showing an example of a pixel of a display device according to an embodiment of the present invention. (b) It is a schematic cross-sectional view of an example of a display device using an organic light-emitting device according to an embodiment of the present invention. [Figure 3] It is a schematic diagram showing an example of a display device according to an embodiment of the present invention. [Figure 4] (a) It is a schematic diagram showing an example of an imaging device according to an embodiment of the present invention. (b) It is a schematic diagram showing an example of an electronic device according to an embodiment of the present invention. [Figure 5] (a) It is a schematic diagram showing an example of a display device according to an embodiment of the present invention. (b) It is a schematic diagram showing an example of a foldable display device. [Figure 6] (a) It is a schematic diagram showing an example of a lighting device according to an embodiment of the present invention. (b) It is a schematic diagram showing an example of a moving body having a vehicle lamp according to an embodiment of the present invention. [Figure 7](a) A schematic diagram showing an example of a wearable device according to one embodiment of the present invention. (b) A schematic diagram showing another example of a wearable device according to one embodiment of the present invention. [Figure 8] (a) A schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. (b) A schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. [Modes for carrying out the invention]

[0010] ≪Organic compounds≫ The organic compound according to this embodiment is represented by the following general formula [1].

[0011] [ka]

[0012] <R1からR8> In general formula [1], R1 to R8 are 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 substituted or unsubstituted heteroaryloxy group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

[0013] Examples of halogen atoms include, but are not limited to, fluorine, chlorine, bromine, and iodine.

[0014] Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, secondary butyl, octyl, cyclohexyl, 1-adamantyl, and 2-adamantyl groups. Among these, alkyl groups having 1 to 10 carbon atoms are preferred.

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

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

[0017] Examples of aryl groups include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, and triphenylenyl groups. Among these, aryl groups with 6 to 18 carbon atoms are preferred.

[0018] Examples of heteroaryl groups include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, thienyl, furanyl, pyronyl, benzothienyl, benzofuranyl, indonyl, dibenzothiophenyl, and dibenzofuranyl groups. Among these, heteroaryl groups with 3 to 15 carbon atoms are preferred.

[0019] Examples of aryloxy groups and heteroaryloxy groups include, but are not limited to, phenoxy groups and thienyloxy groups. Among these, aryloxy groups with 6 to 18 carbon atoms and heteroaryloxy groups with 3 to 15 carbon atoms are preferred.

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

[0021] Examples of substituents that may further be present include, but are not limited to, alkyl groups, alkoxy groups, amino groups, aryl groups, aryloxy groups, heteroaryl groups, heteroaryloxy groups, and silyl groups; alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, and tert-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, thiol group, and cyano group.

[0022] <Ar1からAr4> In general formula [1], Ar1 to Ar4 are independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, respectively.

[0023] Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, secondary butyl, octyl, cyclohexyl, 1-adamantyl, and 2-adamantyl groups. Among these, alkyl groups having 1 to 10 carbon atoms are preferred.

[0024] Examples of aryl groups include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, and triphenylenyl groups.

[0025] Examples of heteroaryl groups include, but are not limited to, heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, thienyl, furanyl, pyronyl, benzothienyl, benzofuranyl, indonyl, dibenzothiophenyl, and dibenzofuranyl.

[0026] Specific examples of substituents that alkyl groups, aryl groups, and heteroaryl groups may further have include, but are not limited to, those described in R1 to R8.

[0027] <l> In the general formula [1], L represents a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0028] Examples of arylene groups include, but are not limited to, divalent groups derived from phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, and triphenylenyl groups.

[0029] Examples of heteroarylene groups include, but are not limited to, divalent groups derived from pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, thienyl, furanyl, pyronyl, benzothienyl, benzofuranyl, indonyl, dibenzothiophenyl, and dibenzofuranyl groups.

[0030] Specific examples of substituents that the arylene group and heteroarylene group may further possess include, but are not limited to, those described in R1 to R8.

[0031] <x> In the general formula [1], X is independently selected from oxygen, sulfur, selenium, tellurium, N(Z), and C(W1)(W2). The X atoms may be the same or different.

[0032] [Z] Z is independently 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.

[0033] Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, secondary butyl, octyl, cyclohexyl, 1-adamantyl, and 2-adamantyl groups. Among these, alkyl groups having 1 to 10 carbon atoms are preferred.

[0034] Examples of aryl groups include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, and triphenylenyl groups. Among these, aryl groups with 6 to 18 carbon atoms are preferred.

[0035] Examples of heteroaryl groups include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, and isoquinolyl groups. Among these, heteroaryl groups with 3 to 15 carbon atoms are preferred.

[0036] Specific examples of substituents that alkyl groups, aryl groups, and heteroaryl groups may further have include, but are not limited to, those described in R1 to R8.

[0037] [W1 to W2] W1 and W2 are independently 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, respectively.

[0038] Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, secondary butyl, octyl, cyclohexyl, 1-adamantyl, and 2-adamantyl groups. Among these, alkyl groups having 1 to 10 carbon atoms are preferred.

[0039] Examples of aryl groups include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, and triphenylenyl groups. Among these, aryl groups with 6 to 18 carbon atoms are preferred.

[0040] Examples of heteroaryl groups include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, and isoquinolyl groups. Among these, heteroaryl groups with 3 to 15 carbon atoms are preferred.

[0041] Specific examples of substituents that alkyl groups, aryl groups, and heteroaryl groups may further have include, but are not limited to, those described in R1 to R8.

[0042] <Preferred Compounds> Preferred organic compounds include those represented by the following general formulas [2-1] to [5-2].

[0043] [ka]

[0044] [ka]

[0045] [Chemical formula]

[0046] [Chemical formula]

[0047] [From Y1 to Y 17 , Y 19 to Y 25 In general formulas [2-1] to [5-2], Y1 to Y 17 , Y 19 to Y 25 are each independently selected from C(A) and a nitrogen atom.

[0048] In general formulas [3-1], [3-2] or [3-3], when Y2 and Y7, Y4 and Y 11 are C(A), the respective As may be bonded to each other to form a ring.

[0049] In general formulas [4-1], [4-2] or [4-3], when Y2 and Y7, Y4 and Y 11 , Y8 and Y 13 , Y 10 and Y 17 are C(A), the respective As may be bonded to each other to form a ring. In general formula [4-4], when Y2 and Y 12 , Y4 and Y 10 , Y8 and Y 13 , Y 10 and Y 17 are C(A), the respective As may be bonded to each other to form a ring.

[0050] {A} ​A is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

[0051] Specific examples of halogen atoms, alkyl groups, aryl groups, heteroaryl groups, and silyl groups are the same as those described in R1 to R8, but are not limited to these. Similarly, specific examples of substituents that alkyl groups, aryl groups, heteroaryl groups, and silyl groups may further have are the same as those described in R1 to R8, but are not limited to these.

[0052] Further preferred organic compounds include those represented by the following general formulas [6] to

[14] .

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] [R9 to R 44 ] In general formulas [6] to

[14] , R9 to R 44 Each of these is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

[0063] Specific examples of halogen atoms, alkyl groups, aryl groups, heteroaryl groups, and silyl groups are the same as those described in R1 to R8, but are not limited to these. Similarly, specific examples of substituents that alkyl groups, aryl groups, heteroaryl groups, and silyl groups may further have are the same as those described in R1 to R8, but are not limited to these.

[0064] In the general formula

[11] , R 16 and R 19 , R 18 and R 21 These elements may also be joined to each other to form a ring.

[0065] In the general formula

[12] , R 24 and R 27 , R 26 and R 29 , R 28 and R 31 , R 30 and R 33 These elements may also be joined to each other to form a ring.

[0066] [W3 to W4] In general formula

[14] , W3 to W4 are independently 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, respectively.

[0067] Specific examples of alkyl groups, aryl groups, and heteroaryl groups are the same as those described in R1 to R8, but are not limited to these. Similarly, specific examples of substituents that alkyl groups, aryl groups, and heteroaryl groups may further have are the same as those described in R1 to R8, but are not limited to these.

[0068] <Synthesis method> Next, a method for synthesizing the organic compound according to this embodiment will be described. The organic compound according to this embodiment is synthesized, for example, according to the synthesis route shown below.

[0069] [ka]

[0070] Here, by appropriately changing G1 to G4 above, a compound represented by the general formula [1] can be obtained. Details of the synthesis method will be explained in the examples.

[0071] <Features> Next, the organic compound according to this embodiment has the following characteristics, resulting in a compound with high luminous efficiency and high color purity. Furthermore, by using the organic compound according to this embodiment, it is possible to provide an organic light-emitting element with excellent color purity and luminous efficiency. (1) The emission wavelength of the basic skeleton itself is in the blue region, resulting in good color purity and high luminescence efficiency. (2) Due to its low LUMO level, it has high stability against oxygen and high durability.

[0072] The following describes the properties of the basic skeleton of the organic compound according to this embodiment, comparing and contrasting it with comparative compounds having a similar structure to the organic compound of this embodiment.

[0073] (1) The emission wavelength of the basic skeleton itself is in the blue region, resulting in good color purity and high luminescence efficiency.

[0074] In inventing the organic compound represented by general formula [1], the inventors focused on the basic structure itself.

[0075] First, in order to exhibit blue emission with good color purity, it is preferable that the basic framework itself is in the blue region with high color purity. In this embodiment, the desired emission wavelength region is the blue region with high color purity, and specifically, when the emission intensity at the maximum emission wavelength in a dilute solution is set to 1.0, the intensity ratio at 460 nm is 0.3 or higher. The basic framework of this embodiment is a framework suitable for producing the desired blue emission.

[0076] Table 1 shows a comparison of the wavelength of the S1 (lowest singlet excited state) determined by molecular orbital calculations and the emission spectra in dilute toluene solution for exemplary compounds A1, A7, A10, and A13 according to this embodiment, and comparative compound 1-a. Specifically, after measuring the emission spectra, the emission intensity at 460 nm was compared, with the maximum emission intensity set to 1.0. The emission wavelength was measured using a Hitachi F-4500 at room temperature by photoluminescence measurement of a diluted toluene solution at an excitation wavelength of 350 nm.

[0077] [Table 1]

[0078] Table 1 shows that, compared to comparative compound 1-a, the compound of this embodiment, which is a condensed ring structure diazabolol derivative, has a longer S1 wavelength. Furthermore, when comparing the emission (PL) intensity at 460 nm, which is the wavelength required for high-purity blue emission, comparative compound 1-a had an intensity of less than 0.1 because its emission wavelength is short, while the compound of this embodiment showed an intensity of 0.3 or higher.

[0079] As described above, the compound of this embodiment exhibits a longer emission wavelength and high-efficiency emission in the blue region with high color purity. Thus, we have found that a unique effect of the fused ring structure diazabolol derivative is that it exhibits high-efficiency blue emission with high color purity.

[0080] Furthermore, the LUMO energy, electron orbital distribution, and S1 energy mentioned above were visualized using molecular orbital calculations. The molecular orbital calculation method used was the widely adopted Density Functional Theory (DFT). 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.

[0081] (2) Due to its low LUMO level, it has high stability against oxygen and high durability.

[0082] In organic semiconductors, for compounds with similar band gaps, a lower HOMO-LUMO energy level (further from the vacuum level) results in greater stability against oxygen. Therefore, lowering the LUMO energy level increases stability against oxygen, improving the durability of the compound itself and the organic light-emitting device.

[0083] Therefore, the inventors focused on LUMO. Figure 1 shows a comparison of the LUMO values, LUMO and HOMO electron orbitals, obtained by molecular orbital calculations, using exemplary compounds A1, A5, and C1 according to this embodiment, and comparative compound 1-b, which has a benzene ring fused along the long axis of comparative compound 1-a. Note that comparative compound 1-b is used instead of 1-a in the explanation in order to compare the number of π electrons fused to the cyclic diazabolol skeleton.

[0084] As shown in Figure 1, compared to comparative compound 1-b, the LUMO orbital distribution in the compound of this embodiment is less concentrated in the aromatic ring region at the long axis terminal and more localized near the center of the molecule containing two electron-withdrawing boron atoms. Therefore, we found that the compound of this embodiment is more influenced by the boron atoms and has the characteristic of having a lower LUMO (further from the vacuum level).

[0085] Comparative compound 1-b has a skeleton in which 10π electrons derived from naphthalene are condensed onto the cyclic diazabolol skeleton, while exemplary compound A1, one of the compounds in this embodiment, has a skeleton in which 10π electrons derived from benzothiophene are condensed onto the cyclic diazabolol skeleton. In other words, the number of π electrons influencing the diazabolol skeleton is the same in comparative compound 1-b and exemplary compound A1. However, as described above, in the compounds of this embodiment, the molecular orbitals of the LUMO are not well distributed in the benzothiophene region at the long axis terminal. Therefore, in the compounds of this embodiment, the 10π electrons derived from benzothiophene have little influence on the LUMO and are localized near the center of the molecule containing two boron atoms, thereby maintaining the electron-withdrawing properties derived from the boron atoms and achieving a low LUMO.

[0086] Furthermore, example compound A5 has two benzene rings as L between the two boron atoms, and its structure is one benzene ring extended in the central part of the molecular structure compared to example compound A1. Similar to example compound A1, it can be seen that the LUMO molecular orbital of example compound A5 is localized in the center of the molecule, containing the two boron atoms. Example compound C1 has an electron-withdrawing pyrazine group at L, which links the two boron atoms, and similar to example compound A1, the LUMO molecular orbital is localized in the center of the molecule, containing the two boron atoms.

[0087] Furthermore, because the organic compounds according to this embodiment have a low LUMO, they have high stability against oxygen. When using the organic compounds according to this embodiment as a guest in the light-emitting layer of an organic light-emitting device, it is particularly preferable to use a material with a higher LUMO than the organic compounds according to this embodiment (a material whose LUMO is closer to the vacuum level) as the host. As shown in the example compounds above, the LUMO orbital distribution of the organic compounds according to this embodiment is localized near the center of the molecule, and the orbitals do not extend to the terminal portion in the long axis direction. Therefore, the organic compounds according to this embodiment have a structure in which the transfer of electrons accepted by the guest to other molecules is suppressed, increasing the probability of hole-electron recombination in the light-emitting layer and improving luminescence efficiency. In addition, because the organic compounds according to this embodiment have a low LUMO, their stability against oxygen is also improved when used in an organic light-emitting device, resulting in improved durability.

[0088] On the other hand, similarly in the case of comparative compound 1-b, if a material with a higher LUMO is used as the host, the LUMO orbital distribution is uniformly distributed along the long axis, making it easier for electrons accepted by the guest to be transferred to other molecules, making it difficult to retain electrons in the luminescent layer, and thus reducing the luminescence efficiency. Furthermore, because comparative compound 1-b has a higher LUMO than the example compound, its stability to oxygen is inferior, resulting in reduced durability.

[0089] Furthermore, regarding the electron orbitals of the HOMO, while example compounds A1, A5, and C1 have a uniform distribution along the long axis, comparative compound 1-b lacks orbitals in the region containing two boron atoms and the benzene ring bonded between them, resulting in a significantly different orbital distribution from that of the LUMO. Consequently, the emission spectrum exhibits an emission spectrum originating from intramolecular CT, leading to a broad full width at half maximum (FWHM) and making it difficult to achieve high color purity. On the other hand, in the organic compounds according to this embodiment, represented by example compounds A1, A5, and C1, although there are differences in the electron orbitals of the HOMO and LUMO, both the HOMO and LUMO have electron orbitals on the diazabolol structure. Therefore, in the organic compounds according to this embodiment, there is little structural change between the ground state and the excited state, resulting in a narrower FWHM of the emission spectrum and enabling the exhibiting of high color purity.

[0090] As described above, the organic compound according to this embodiment is a compound having the properties of (1) and (2) above, and therefore exhibits high-efficiency blue light emission with high color purity, and is a chemically stable compound with a low LUMO compared to the comparative compound. Accordingly, by using the organic compound according to this embodiment, an organic light-emitting element with excellent color purity, luminous efficiency, and element durability can be obtained.

[0091] <Specific example> Specific examples of organic compounds according to this embodiment are shown below. However, this embodiment is not limited to these examples.

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] Examples of compounds belonging to Group A are compounds in formula [1] in which Ar1 to Ar4 are aryl groups, alkyl groups, benzofuranyl groups, and benzothienyl groups, and L is an arylene group. Compounds belonging to Group A exhibit short-wavelength blue emission and higher emission intensity. That is, when used in an emission layer, compounds belonging to Group A exhibit blue emission with higher color purity and higher luminescence efficiency.

[0099] Examples of compounds belonging to group B are compounds in formula [1] in which Ar1 to Ar4 are electron-withdrawing groups such as heteroaryl groups, cyano groups, or phenyl groups having halogen elements, and L is an arylene group. Compounds belonging to group B have higher electron-accepting ability among the compounds in this embodiment, and at the same time can also exhibit blue light emission with high color purity.

[0100] Examples of compounds belonging to group C are compounds in formula [1] in which Ar1 to Ar4 are aryl groups, alkyl groups, benzofuranyl groups, and benzothienyl groups, and L is a heteroarylene group. Compounds belonging to group C can exhibit high electron-accepting ability and high luminescence efficiency among the compounds according to this embodiment.

[0101] The organic compound according to this embodiment exhibits highly efficient luminescence suitable for blue light emission and is a compound with high chemical stability. Therefore, by using the organic compound according to this embodiment as a constituent material for an organic light-emitting device, an organic light-emitting device with good luminescence characteristics and excellent durability can be obtained.

[0102] Organic light-emitting diodes The organic light-emitting element of this embodiment comprises 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 element of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, provided that it has a light-emitting layer. If 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, and the like. The light-emitting layer may also be a single layer or a laminate consisting of multiple layers.

[0103] In the organic light-emitting element of this embodiment, at least one layer of the organic compound layer contains the organic compound according to this embodiment. Specifically, the organic compound according to this embodiment is included 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 according to this embodiment is preferably included in the light-emitting layer.

[0104] In the organic light-emitting element of this embodiment, when the organic compound according to this embodiment is included in the light-emitting layer, the light-emitting layer may consist only of the organic compound according to this embodiment, or it may consist of the organic compound according to this embodiment and other compounds. Here, when the light-emitting layer consists 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 in the light-emitting layer. It may also be used as an assist material that can be included in the light-emitting layer. Here, the host is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. The guest is a compound with a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and is responsible for the main light emission. The assist material is a compound with a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and assists the light emission of the guest. The assist material is also called the second host.

[0105] 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, relative to the entire light-emitting layer.

[0106] When the organic compound according to this embodiment is used as an assist material for the light-emitting layer, the concentration of the assist material is preferably 5% by mass or more and 50% by mass or less, and more preferably 10% by mass or more and 30% by mass or less, relative to the entire light-emitting layer.

[0107] Furthermore, when using the organic compound according to this embodiment as a guest for the light-emitting layer, it is preferable to use a material with a higher LUMO level than the organic compound according to this embodiment (a material with a LUMO level closer to the vacuum level) as the host. This is because using a material with a higher LUMO level than the organic compound according to this embodiment as the host allows the organic compound according to this embodiment to accept more electrons supplied to the host of the light-emitting layer. In particular, since the organic compound of this embodiment has high electron-accepting ability, i.e., a low LUMO level, using a material with a higher LUMO level than the organic compound of this embodiment as the host allows the organic compound according to this embodiment to accept more electrons supplied to the host of the light-emitting layer.

[0108] The inventors have conducted various studies and found that when the organic compound according to this embodiment is used as a host or guest for the light-emitting layer, particularly as a guest for the light-emitting layer, a device can be obtained that exhibits high efficiency, high brightness, and extremely high durability. This light-emitting layer may be a single layer or a multi-layer, and it is also possible to mix the light emission with the blue light emission of the organic compound in this embodiment by including a light-emitting material having another light emission color. A multi-layer means a state in which one light-emitting layer and another light-emitting layer are stacked. In this case, the light emission color of the organic light-emitting element is not limited to blue. More specifically, it may be white or an intermediate color. In the case of white, the other 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 described later.

[0109] The organic compound according to this embodiment can be used as a constituent material for organic compound layers other than the light-emitting layer constituting the organic light-emitting element of this embodiment. Specifically, it may be used as a constituent material for electron transport layers, electron injection layers, hole transport layers, hole injection layers, hole blocking layers, etc. In this case, the light-emitting color of the organic light-emitting element is not limited to blue. More specifically, it may be white or an intermediate color.

[0110] <Compounds other than the organic compounds of this embodiment> In addition to the organic compounds according to this embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, luminescent compounds, electron-injecting or electron-transporting compounds, etc., can be used together as needed. Examples of these compounds are listed below.

[0111] As hole-implantation transport materials, materials with high hole mobility are preferred to facilitate hole injection from the anode and to transport the injected holes to the light-emitting layer. Furthermore, materials with a high glass transition temperature are preferred to reduce film quality degradation such as crystallization in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole-implantation transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Moreover, the above-mentioned hole-implantation transport materials are also suitably used in electron-blocking layers. Specific examples of compounds used as hole-implantation transport materials are shown below, but are not limited to these.

[0112] [ka]

[0113] Luminescent materials primarily involved in light emission include 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-quinolinolate)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 used as luminescent materials are shown below, but are not limited to these.

[0114] [ka]

[0115] Examples of luminescent layer hosts or luminescence assist materials included in the luminescent layer include aromatic hydrocarbon compounds or their derivatives, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, and organoberylium complexes. Specific examples of compounds used as luminescent layer hosts or luminescence assist materials are shown below, but are not limited to these.

[0116] [ka]

[0117] As electron-transporting materials, any material capable of transporting electrons injected from the cathode to the light-emitting layer can be arbitrarily selected, taking into consideration the balance with the hole mobility of the hole-transporting material. Examples of materials with electron-transporting properties include oxadiazole 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-transporting materials are also suitably used in the hole-blocking layer. Specific examples of compounds used as electron-transporting materials are shown below, but are of course not limited to these.

[0118] [ka]

[0119] <Configuration of an organic light-emitting element> An organic light-emitting element is provided on a substrate by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode. A protective layer, a color filter, a microlens, etc., may be provided on the second electrode. If a color filter is provided, a planarization layer may be provided between it and the protective layer. The planarization layer can be made of acrylic resin or the like. The same applies when a planarization layer is provided between the color filter and the microlens.

[0120] [substrate] Examples of substrates include quartz, glass, silicon wafers, resins, and metals. The substrate may also be equipped with switching elements such as transistors and wiring, and an insulating layer may be provided on top of them. The insulating layer can be made of any material that allows for the formation of contact holes between it and the first electrode, while ensuring insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, and silicon nitride can be used.

[0121] [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 the higher potential is the anode, and the other is the cathode. Alternatively, the electrode that supplies holes to the light-emitting layer can be the anode, and the electrode that supplies electrons can be the cathode.

[0122] For the anode, materials with the largest possible work function are preferable. For example, elemental metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, or mixtures containing these, or alloys combining them, as well as metal oxides such as tin oxide, zinc oxide, indium oxide, tin-indium oxide (ITO), and zinc-indium oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0123] These electrode materials may be used individually or in combination of two or more. Furthermore, the anode may consist of a single layer or multiple layers.

[0124] When used as a reflective electrode, materials such as chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. It is also possible to use the above materials as a reflective film without serving as an electrode. Furthermore, when used as a transparent electrode, oxide transparent conductive layers such as indium tin oxide (ITO) or indium zinc oxide can be used, but are not limited to these. Photolithography can be used to form the electrodes.

[0125] On the other hand, materials with a small work function are preferred for the cathode. Examples include alkali metals such as lithium, alkaline earth metals such as calcium, and elemental metals or mixtures containing aluminum, titanium, manganese, silver, lead, and chromium. Alternatively, alloys combining these elemental metals can also 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 may be used individually or in combination of two or more. The cathode may also be 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 important as long as silver aggregation is reduced. For example, the ratio of silver to other metals may be 1:1, 3:1, etc.

[0126] 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 using DC and AC sputtering methods is more preferable because it provides good film coverage and makes it easier to reduce resistance.

[0127] [Organic compound layer] The organic compound layer may be formed as a single layer or as multiple layers. If there are multiple layers, they may be called a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, or an electron injection layer, depending on their function. The organic compound layer is mainly composed of organic compounds, but may also contain inorganic atoms and inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be placed between the first electrode and the second electrode, or it may be placed in contact with the first electrode and the second electrode.

[0128] The organic compound layer (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 element according to one embodiment of the present invention is formed by the method shown below.

[0129] The organic compound layer constituting the organic light-emitting element according to one embodiment of the present invention can be formed using a dry process such as vacuum deposition, ionization deposition, sputtering, or plasma deposition. Alternatively, instead of a dry process, a wet process can be used in which the layer is formed by dissolving the compound in a suitable solvent and applying a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

[0130] When layers are formed using methods such as vacuum deposition or solution coating, crystallization is less likely to occur, resulting in excellent stability over time. Furthermore, when forming films using coating methods, it is possible to combine the film with an appropriate binder resin.

[0131] Examples of the binder resins mentioned above include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0132] Furthermore, these binder resins may be used individually as homopolymers or copolymers, or as a mixture of two or more types. Additionally, known additives such as plasticizers, antioxidants, and UV absorbers may be used in combination as needed.

[0133] [Protective layer] A protective layer may be provided on the second electrode. For example, by bonding glass with a desiccant to the second electrode, the intrusion of water and other substances 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 second electrode to reduce the intrusion of water and other substances into the organic compound layer. For example, after forming the second electrode, it may be transported to another chamber without breaking the vacuum and a silicon nitride film with a thickness of 2 μm may be formed by the CVD method to serve as a protective layer. A protective layer may also be provided using atomic deposition (ALD) after film formation by the CVD method. The material of the film formed by the ALD method is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed on the film formed by the ALD method by the CVD method. The film formed by the ALD method may have a thinner film thickness than the film formed by the CVD method. Specifically, it may be 50% or less, or even 10% or less.

[0134] [Color Filter] A color filter may be provided on top of the protective layer. For example, a color filter that takes into account the size of the organic light-emitting element may be provided on a separate substrate and bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer as described above using photolithography technology. The color filter may be made of polymer.

[0135] [Planarization layer] A planarizing layer may be provided between the color filter and the protective layer. The planarizing layer is provided to reduce the unevenness of the layer below. It may also be called a material resin layer without limiting its purpose. The planarizing layer may be composed of an organic compound, which may be low molecular weight or high molecular weight, but high molecular weight is preferred.

[0136] The planarization layer may be provided above or below the color filter, and its constituent materials may be the same or different. Specifically, examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, urea resin, etc.

[0137] [Microlens] An organic light-emitting element or organic light-emitting device may have optical elements such as microlenses on its light-emitting side. Microlenses may be made of acrylic resin, epoxy resin, or the like. Microlenses may be used to increase the amount of light extracted from the organic light-emitting element or organic light-emitting device, or to control the direction of the extracted light. Microlenses may have a hemispherical shape. If they have a hemispherical shape, among the tangents tangent to the hemisphere, there is a tangent parallel to the insulating layer, and the point of contact between that tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be similarly determined in any cross-sectional view. That is, among the tangents tangent to the semicircle of the microlens in the cross-sectional view, there is a tangent parallel to the insulating layer, and the point of contact between that tangent and the semicircle is the vertex of the microlens.

[0138] Furthermore, the midpoint of a microlens can also be defined. In the cross-section of a microlens, a line segment can be imagined from the point where one arc ends to the point where another arc ends, and the midpoint of this line segment can be called the midpoint of the microlens. The cross-section used to determine the vertices and midpoints may be a cross-section perpendicular to the insulating layer.

[0139] [Opposite substrate] A counter substrate may be provided on the planarized layer. The counter substrate is called a counter substrate because it is provided in a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. The counter substrate may be the second substrate if the aforementioned substrate is referred to as the first substrate.

[0140] [Pixel circuit] An organic light-emitting device having an organic light-emitting element may have a pixel circuit connected to the organic light-emitting element. The pixel circuit may be an active-matrix type that independently controls the light emission of a first light-emitting element and a second light-emitting element. The active-matrix type circuit may be voltage-programmed or current-programmed. The driving circuit has a pixel circuit for each pixel. The pixel circuit may include a light-emitting element, a transistor that controls the light emission brightness of the light-emitting element, a transistor that controls the light emission timing, a capacitor that holds the gate voltage of the transistor that controls the light emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0141] 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 the transistors constituting the pixel circuit may be smaller than the mobility of the transistors constituting the display control circuit. The slope of the current-voltage characteristic of the transistors constituting the pixel circuit may be smaller than the slope of the current-voltage characteristic of the transistors constituting the display control circuit. The slope of the current-voltage characteristic can be measured by the so-called Vg-Ig characteristic. The transistors constituting the pixel circuit are transistors connected to the light-emitting element, such as the first light-emitting element.

[0142] [Pixels] An organic light-emitting device having an organic light-emitting element may have a plurality of pixels. Each pixel may have subpixels that emit light of a different color from the others. The subpixels may each have, for example, RGB light-emitting colors.

[0143] A pixel emits light from a region also called the pixel aperture. This region is the same as the first region. The pixel aperture 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, and specifically, it may be 8 μm, 7.4 μm, 6.4 μm.

[0144] Pixels can take on known arrangements in a plan view. For example, they may be in a stripe arrangement, delta arrangement, pentile arrangement, or Bayer arrangement. The shape of subpixels in a plan view may be any known shape. For example, rectangles, rhombuses, hexagons, etc. Of course, even if it is not a precise shape, if it is close to a rectangle, it is included in the category of rectangles. The shape of subpixels and the pixel arrangement can be used in combination.

[0145] <Applications of organic light-emitting diodes> The organic light-emitting element according to this embodiment can be used as a component of a display device or lighting device. Other applications include exposure light sources for electrophotographic image forming apparatuses, backlights for liquid crystal display devices, and light-emitting devices with a color filter in a white light source.

[0146] The display device may also be an image information processing device having an image input unit that receives image information from an area CCD, linear CCD, memory card, etc., 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, and at least one of the plurality of pixels may have the organic light-emitting element of this embodiment and a transistor connected to the organic light-emitting element.

[0147] Furthermore, the display unit of the imaging device or inkjet printer may have a touch panel function. The driving method for this touch panel function may be infrared, capacitive, resistive, or electromagnetic induction, and is not particularly limited. The display device may also be used as the display unit of a multifunction printer.

[0148] Next, a display device according to this embodiment will be described with reference to the drawings. Figure 2 is a schematic 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).

[0149] Figure 2(a) shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The light emission color may be distinguished by the wavelength emitted from the light-emitting layer, or the light emitted from the sub-pixel may be selectively transmitted or color-converted by a color filter or the like. Each sub-pixel 10 has a reflective electrode which is a first electrode 2 on an interlayer insulating layer 1, an insulating layer 3 covering the end of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode which is a second electrode 5, a protective layer 6, and a color filter 7.

[0150] The interlayer insulating layer 1 may have transistors and capacitive elements placed in the layer below or inside it. The transistor and the first electrode 2 may be electrically connected via a contact hole or the like (not shown).

[0151] The insulating layer 3 is also called a bank or pixel isolation layer. It covers the edge of the first electrode 2 and surrounds the first electrode 2. The portion not covered by the insulating layer 3 is in contact with the organic compound layer 4 and becomes the light-emitting region.

[0152] 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.

[0153] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0154] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 is shown as a single layer, it may consist of multiple layers. Each layer may contain an inorganic compound layer and an organic compound layer.

[0155] The color filter 7 is classified into 7R, 7G, and 7B according to its color. The color filter 7 may be formed on a planarization film (not shown). The color filter 7 may also have a resin protective layer (not shown). Alternatively, the color filter 7 may be formed on a protective layer 6. Or it may be bonded to an opposing substrate such as a glass substrate after being placed on it.

[0156] The display device 100 in Figure 2(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 placed on the insulating layer 12, and the gate electrode 13, gate insulating film 14, and semiconductor layer 15 of the active element are arranged therein. The TFT 18 is also composed of a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on top of the TFT 18. The anode 21 and the source electrode 17 that constitute the organic light-emitting element 26 are connected via a contact hole 20 provided in the insulating film 19.

[0157] Note that the method of 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 configuration shown in Figure 2(b). In other words, it is sufficient if 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 refers to a thin-film transistor.

[0158] In the display device 100 shown in Figure 2(b), the organic compound layer 22 is depicted as a single layer, but the organic compound layer 22 may consist of multiple layers. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce the degradation of the organic light-emitting element 26.

[0159] In the display device 100 shown in Figure 2(b), a transistor is used as the switching element, but other switching elements may be used instead.

[0160] Furthermore, the transistor used in the display device 100 in Figure 2(b) is not limited to a transistor using a single-crystal silicon wafer, but may also be a thin-film transistor having an active layer on an insulating surface of the substrate. Examples of the active layer 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.

[0161] The transistors included in the display device 100 in Figure 2(b) may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the transistors are manufactured by processing the substrate itself, such as a Si substrate. In other words, having transistors within a substrate can be seen as the substrate and transistors being formed as a single unit.

[0162] The organic light-emitting element according to this embodiment has its luminescence controlled by a TFT, which is an example of a switching element, and by providing multiple organic light-emitting elements on the surface, an image can be displayed using the luminescence of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor made of low-temperature polysilicon, or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also mean "within the substrate." Whether to provide a transistor within the substrate or to use a TFT is selected depending on the size of the display area; for example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0163] Figure 3 is a schematic diagram showing an example of a display device according to this embodiment. The display device 1000 may have 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. Flexible printed circuits FPCs 1002 and 1004 are connected to the touch panel 1003 and the display panel 1005. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, or it may be provided in a different location even if it is a portable device.

[0164] The display device according to this embodiment may have a color filter having red, green, and blue colors. The color filter may have the red, green, and blue colors arranged in a delta array.

[0165] The display device according to this embodiment may be used in the display unit of a mobile terminal. In that case, it may have both display and operation functions. Examples of mobile terminals include smartphones and other mobile phones, tablets, and head-mounted displays.

[0166] The display device according to this embodiment may be used in the display unit of an imaging device having an optical unit with multiple lenses and an image sensor that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the image sensor. Furthermore, the display unit may be a display unit exposed to the outside of the imaging device or a display unit located inside the viewfinder. The imaging device may be a digital camera or a digital video camera.

[0167] Figure 4(a) 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 have a display device according to this embodiment. In that case, the display device may display not only the image to be captured, but also environmental information, imaging instructions, etc. Environmental information may include the intensity of ambient light, the direction of ambient light, the speed at which the subject is moving, the possibility of the subject being obscured by an obstacle, etc.

[0168] Since the optimal timing for imaging is very short, it is best to display the information as quickly as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment, because organic light-emitting elements have a fast response speed. Display devices using organic light-emitting elements can be used more suitably than liquid crystal display devices, which require a fast display speed.

[0169] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses that form an image on the image sensor housed in the housing 1104. The focus can be adjusted by adjusting the relative positions of the multiple lenses. This operation can also be performed automatically. The imaging device may also be called a photoelectric converter. The photoelectric converter may not capture images sequentially, but may include imaging methods such as detecting the difference from the previous image or extracting from an image that is always being recorded.

[0170] Figure 4(b) is a schematic diagram showing 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 response unit. The operation unit 1202 may also be a biometric recognition unit that recognizes a fingerprint to unlock or otherwise perform actions. 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. Images captured by the camera function are displayed on the display unit 1201. Examples of the electronic device 1200 include smartphones and laptop computers.

[0171] Figure 5 is a schematic diagram showing an example of a display device according to this embodiment. Figure 5(a) is 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. It has a frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in Figure 5(a). The lower edge of the frame 1301 may also serve as the base. In addition, 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.

[0172] Figure 5(b) is a schematic diagram showing another example of the display device according to this embodiment. The display device 1310 in Figure 5(b) is configured to be foldable 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 have light-emitting elements according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single display device without seams. The first display unit 1311 and the second display unit 1312 can be separated by a 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 together display a single image.

[0173] Figure 6(a) is a schematic diagram showing 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, and an optical filter 1404 and a light diffusion unit 1405 that transmit light emitted from the light source 1402. The light source 1402 may have 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 the light from the light source, such as for lighting up, and deliver light over a wide area. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light-emitting side of the lighting. A cover may be provided on the outermost part as needed.

[0174] The lighting device is, for example, a device for illuminating a room. The lighting device may emit white light, cool white light, or any other color from blue to red. It may have a dimming circuit to adjust the brightness of these lights. 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. White light has a color temperature of 4200K, and cool white light has a color temperature of 5000K. The lighting device may have a color filter.

[0175] Furthermore, the lighting device according to this embodiment may have a heat dissipation section. The heat dissipation section releases heat from inside the device to the outside, and examples include metals with high specific heat, liquid silicon, etc.

[0176] Figure 6(b) is a schematic diagram of an automobile, which is an example of a mobile body according to this embodiment. The automobile has a taillight, which is an example of a lighting device. The automobile 1500 has a taillight 1501, and may be configured to illuminate when the brakes are applied or the like.

[0177] The taillight 1501 may have an organic light-emitting element according to this embodiment. The taillight 1501 may have a protective member to protect the organic light-emitting element. The protective member has a reasonably high strength and can be made of any transparent material, but it is preferably made of polycarbonate or the like. A frangic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.

[0178] The automobile 1500 may have a body 1503 and windows 1502 attached thereto. The windows 1502 may be transparent displays, unless they are windows for checking the front and rear of the automobile. The transparent displays may have organic light-emitting elements according to this embodiment. In this case, the constituent materials such as electrodes of the organic light-emitting element are made of transparent members.

[0179] The mobile body according to this embodiment may be a ship, aircraft, drone, etc. The mobile 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 an organic light-emitting element according to this embodiment.

[0180] Referencing Figure 7, examples of applications of the display devices of each embodiment described above will be explained. The display device can be applied to systems that can be worn as wearable devices such as smart glasses, HMDs, and smart contacts. The imaging display device used in such applications has an imaging device capable of photoelectric conversion of visible light and a display device capable of emitting visible light.

[0181] Figure 7(a) is a schematic diagram showing an example of a wearable device according to one embodiment of the present invention. Using Figure 7(a), we will explain a pair of glasses 1600 (smart glasses) according to one application example. An imaging device 1602, such as a CMOS sensor or SPAD, is provided on the front surface side of the lens 1601 of the glasses 1600. In addition, the display devices of each embodiment described above are provided on the back surface side of the lens 1601.

[0182] The eyeglasses 1600 further include a control device 1603. The control device 1603 functions as a power supply that provides power to the imaging device 1602 and the display device. The control device 1603 also controls the operation of the imaging device 1602 and the display device. The lens 1601 has an optical system formed therein for focusing light onto the imaging device 1602.

[0183] Figure 7(b) is a schematic diagram showing another example of a wearable device according to one embodiment of the present invention. Using Figure 7(b), we will describe a pair of glasses 1610 (smart glasses) according to one application example. The glasses 1610 have a control device 1612, which is equipped with an imaging device corresponding to the imaging device 1602 in Figure 7(a) and a display device. The lens 1611 has an optical system formed therein for projecting light emitted from the imaging device and the display device in the control device 1612, and an image is projected onto the lens 1611. The control device 1612 functions as a power supply that supplies power to the imaging device and the display device, and also controls the operation of the imaging device and the display device.

[0184] The control device 1612 may have a gaze detection unit that detects the wearer's gaze. Gaze detection may use infrared light. The infrared light emitter emits infrared light towards the user's eyeball that is fixated on the displayed image. An imaging unit having a photodetector detects the reflected light from the eyeball of the emitted infrared light, thereby obtaining an image of the eyeball. By having a reduction means that reduces the light from the infrared light emitter to the display unit in a planar view, the degradation of image quality is reduced. The user's gaze toward the displayed image is detected from the image of the eyeball obtained by imaging with infrared light. Any known method can be applied to gaze detection using the image of the eyeball. As an example, a gaze detection method based on the Purkinje image obtained by the reflection of irradiated light from the cornea can be used. More specifically, gaze detection processing based on the pupil-corneal reflection method is performed. Using the pupil-corneal reflection method, the user's gaze is detected by calculating a gaze vector representing the orientation (rotation angle) of the eyeball based on the pupil image and Purkinje image included in the image of the eyeball.

[0185] A display device according to one embodiment of the present invention has an imaging device having a light-receiving element, and may control the display image of the display device based on the user's gaze information from the imaging device. Specifically, the display device determines a first field of view area that the user is fixated on and a second field of view area other than the first field of view area, based on the gaze information. The first field of view area and the second field of view area may be determined by the control device of the display device, or they may be determined by an external control device and received by the display device. 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.

[0186] Furthermore, the display area has a first display area and a second display area different from the first display area, and based on gaze information, the area with higher priority is determined from the first display area and the second display area. The first and second view areas may be determined by the control device of the display device, or they 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 the areas other than the high-priority area. In other words, the resolution of areas with relatively lower priority may be set lower.

[0187] AI may be used to determine the primary field of view and high-priority areas. The AI ​​may be a model configured to estimate the angle of gaze and the distance to the target object at the end of the line of sight from the image of the eye, using the image of the eye and the direction the eye was actually looking in that image as training data. The AI ​​program may be installed in the display device, the imaging device, or an external device. If installed in an external device, it will be transmitted to the display device via communication.

[0188] When display control is based on visual detection, this method is preferably applicable to smart glasses that further include an imaging device for capturing images of the surrounding environment. The smart glasses can display the captured external information in real time.

[0189] Figure 8(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 photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fuser 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoreceptor 27. This exposure light source 28 has an organic light-emitting element according to this embodiment. The developing unit 31 has toner or the like. The charging unit 30 charges the photoreceptor 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 fuser 35 fixes the image formed on the recording medium 34.

[0190] Figures 8(b) and 8(c) are diagrams showing the exposure light source 28, schematic diagrams showing how multiple light-emitting units 36 are arranged on a long substrate. The arrow 37 is parallel to the axis of the photoreceptor and represents the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis in which the photoreceptor 27 rotates. This direction can also be called the long axis direction of the photoreceptor 27. Figure 8(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoreceptor 27. Figure 8(c) is a different configuration from Figure 8(b), in which the light-emitting units 36 are arranged alternately in the column direction in the first column and the second column, respectively. The first column and the second column are arranged at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged with intervals between them. In the second column, light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. That is, multiple light-emitting units 36 are also arranged with intervals between them in the row direction. The arrangement in Figure 8(c) can also be described as a grid pattern, a houndstooth pattern, or a checkerboard pattern.

[0191] As described above, by using the device employing the organic light-emitting element according to this embodiment, it becomes possible to display images with good quality and stable display even for extended periods. [Examples]

[0192] The present invention will be described below with reference to examples. However, the present invention is not limited to these examples.

[0193] [Example 1 (Synthesis of Exemplary Compound A1)] [ka]

[0194] (1) Synthesis of compound H2 The following compounds, reagents, and solvents were placed in a 300 mL round-bottom flask. Compound H1: 10.00 g (46.9 mmol) Glacial acetic acid: 140 ml Next, the reaction solution was stirred under a nitrogen stream at room temperature for 10 minutes, and then 40 ml of acetic acid and 20 ml of HNO3 were mixed and gradually added dropwise. After stirring at room temperature for 5 hours, the mixture was quenched by adding water, filtered, and the resulting filtrate was washed with water. Purification by recrystallization with ethyl acetate / heptane = 1 / 1 yielded 8.48 g of the yellow compound H2 (yield: 70%).

[0195] (2) Synthesis of compound H4 The following compounds, reagents, and solvents were placed in a 300 mL round-bottom flask. Compound H2: 8.40g (32.6mmol) Compound H3: 8.66g (93.0mmol) Triethylamine: 4.95g (48.9mmol) DMF: 150ml Next, the reaction solution was heated under a nitrogen stream at 120°C for 30 minutes, and then quenched with water. The solid was isolated by filtration, washed with water, and recrystallized from dichloromethane / heptane to obtain 7.93 g of the yellow compound H4 (yield: 90%).

[0196] (3) Synthesis of compound H5 The following compounds, reagents, and solvents were placed in a 300 ml round-bottom flask. Compound H4: 7.00g (25.9 mmol) Acetic acid: 150ml Water: 150ml Next, 7.55 g (135 mmol) of iron powder was added to the reaction solution under a nitrogen stream in small portions. After stirring at room temperature for 2 hours, the mixture was filtered through Celite and washed with dichloromethane. The combined filtrate was washed with water and aqueous sodium carbonate solution. After removing the solvent by distillation, the mixture was purified by silica gel column chromatography (hexane / dichloromethane = 4 / 1) to obtain 4.05 g (yield: 65%) of the white compound H5.

[0197] (4) Synthesis of compound H7 The following compounds, reagents, and solvents were placed in a 300 ml round-bottom flask. Compound H5: 3.00g (12.5mmol) Compound H6: 2.07g (12.5mmol) Toluene: 150ml Next, the reaction solution was heated to 120°C under a nitrogen stream and stirred under reflux for 5 hours. After the reaction was complete, the solution was concentrated, heptane was added, and the mixture was filtered. Subsequently, the mixture was dispersed and washed with heptane to obtain 3.95 g of the white compound H7 (yield: 55%).

[0198] (5) Synthesis of Exemplary Compound A1 The following compounds, reagents, and solvents were placed in a 200 ml round-bottom flask. Compound H7: 1.50g (1.32mmol) Compound H8: 4.26g (1.98mmol) Pd(OAc)2: 15 mg (0.06 mmol) Tri-O-trilphosphine: 35 mg (0.12 mmol) tBuOK: 0.67g (5.90 mmol) Xylene: 75ml Next, the reaction solution was heated to 145°C under a nitrogen stream and stirred under reflux for 5 hours. After the reaction was complete, it was filtered. This was purified by silica gel column chromatography (chlorobenzene), and then recrystallized with toluene to obtain 0.43 g (yield: 45%) of the white exemplary compound A1.

[0199] For example compound A1, mass spectrometry was performed using MALDI-TOF-MS (Bruker Autoflex LRF). [MALDI-TOF-MS] Measured value: m / z = 726 Calculated value: C 46 H 32 B2N4S2=726

[0200] [Example 2 (Synthesis of Exemplary Compound A4)] Compounds up to H7 were synthesized in the same manner as in Example 1. [ka]

[0201] (1) Synthesis of Exemplary Compound A4 The following compounds, reagents, and solvents were placed in a 100 ml round-bottom flask. Compound H7: 1.50g (1.32mmol) Compound H9: 0.94g (6.60mmol) Triethylamine: 0.80g (7.92 mmol) DMF: 50ml Next, the reaction solution was heated under a nitrogen stream at 120°C for 30 minutes, and then quenched with water. The solid was isolated by filtration, washed with water, purified by silica gel column chromatography (chlorobenzene), and then recrystallized with cyclohexane to obtain 0.43 g (yield: 55%) of the white exemplary compound A4.

[0202] For example compound A4, mass spectrometry was performed using MALDI-TOF-MS (Bruker Autoflex LRF). [MALDI-TOF-MS] Measured value: m / z = 602 Calculated value: C 36 H 28 B2N4S2=602

[0203] [Examples 3 to 30 (Synthesis of Exemplary Compounds)] As shown in Tables 2 to 6, for the exemplary compounds shown in Examples 3 to 30, except that the raw material H1 in Example 1 was changed to raw material 1, the raw material H3 in Example 1 was changed to raw material 2, the raw material H6 in Example 1 was changed to raw material 3, and the raw material H8 in Example 1 or the raw material H9 in Example 2 was changed to raw material 4, the exemplary compounds were synthesized in the same manner as in Example 1 or Example 2. The measured values of the mass spectrometry results measured in the same manner as in Example 1: m / z are also shown.

[0204]

Table 2

[0205]

Table 3

[0206]

Table 4

[0207]

Table 5

[0208]

Table 6

[0209] [Example 31] In this example, an organic EL device with a bottom emission structure 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 was fabricated.

[0210] First, an ITO film was deposited on a glass substrate, and an ITO electrode (anode) was formed by applying a desired patterning process. At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed in this way was used as the ITO substrate in the following steps. Next, the organic compound layer and electrode layer shown in Table 7 were continuously deposited on the ITO substrate by vacuum deposition using resistance heating in a vacuum chamber. At this time, the electrode area of ​​the opposing electrodes (metal electrode layer, cathode) was 3 mm². 2 I made it so that it would be like that.

[0211] [Table 7]

[0212] The characteristics of the obtained elements were measured and evaluated. A blue light emission with a maximum current efficiency of 12.5 cd / A was obtained for the light-emitting element. Specifically, the current-voltage characteristics were measured using a Hewlett-Packard 4140B micro-ammeter, and the luminous intensity was measured using a Topcon BM7. Furthermore, the current density was 20 mA / cm². 2 A continuous operation test was conducted, and the time (LT95) at which the brightness degradation rate reached 5% was measured to be 110 hours. The measurement results are shown in Table 8.

[0213] [Examples 32 to 47, Comparative Example 1] Organic light-emitting devices were fabricated in the same manner as in Example 31, except that the compounds shown in Table 8 were appropriately changed. The characteristics of the obtained devices were measured and evaluated in the same manner as in Example 31. The measurement results are shown in Table 8. Note that comparative compound 1-a is compound 1-a described in Patent Document 1.

[0214] [Table 8]

[0215] As shown in Table 8, the current efficiency of Comparative Example 1 using Comparative Compound 1-a was 8.0 cd / A or less, and the 5% degradation life (LT95) was 70 hours or less, which was worse than the current efficiency and durability characteristics of the blue light-emitting device of this Example. On the other hand, the device using the organic compound of this embodiment showed good durability characteristics. This is because the compound according to this embodiment has a condensed ring structure diazaborole skeleton, so that the emission wavelength is suitable for blue light emission, and the LUMO level is low and the stability against oxygen is high.

[0216] [Example 48] An organic light-emitting device was fabricated in the same manner as in Example 31, except that the compound shown in Table 9 was appropriately changed. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 31.

[0217] [Table 9]

[0218] For the obtained device, the characteristics of the device were measured and evaluated. As a result, good green light emission was obtained from the light-emitting device. The same measuring apparatus as in Example 31 was used. Furthermore, a continuous driving test was conducted at a current density of 100 mA / cm 2 , and when the time (LT95) when the luminance degradation rate reached 5% was measured, it exceeded 410 hours. The measurement results are shown in Table 10.

[0219] [Examples 49 to 56, Comparative Examples 2 to 3] An organic light-emitting device was fabricated in the same manner as in Example 48, except that the compound shown in Table 10 was appropriately changed. Note that the mass ratio of the first host to the guest in Examples 54 to 56 and Comparative Example 3 is 99.5:0.5. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 48. The measurement results are shown in Table 10.

[0220] [Table 10]

[0221] Table 10 shows that Comparative Examples 2 and 3 have a 5% degradation life of 400 hours or less, indicating poor durability. However, the element using the organic compound according to this embodiment has a 5% degradation life exceeding 400 hours. This indicates that the examples have a longer lifespan. The element using the organic compound according to this embodiment exhibits good durability characteristics.

[0222] [Example 57] In this embodiment, an organic EL element with a top-emission structure was fabricated on a substrate in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a first light-emitting layer, a second light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed.

[0223] A 40nm layer of Al and Ti was deposited on a glass substrate using sputtering, and the anode was formed by patterning using photolithography. At this time, the electrode area of ​​the opposing electrodes (metal electrode layer, cathode) was 3mm². 2 Next, the substrate and material, with the washed electrodes already formed, were attached to the vacuum deposition apparatus (manufactured by ULVAC), and 1.3 × 10 -4 Pa(1 × 10) -6 After exhausting to Torr, UV / ozone cleaning was performed. Subsequently, each layer was deposited according to the layer configuration shown in Table 11, and finally, sealing was carried out under a nitrogen atmosphere.

[0224] [Table 11]

[0225] The characteristics of the obtained elements were measured and evaluated. The obtained elements showed good white light emission. Furthermore, the initial brightness was 1000 cd / m². 2 A continuous operation test was conducted, and the brightness degradation rate after 100 hours was measured. The results are shown in Table 12.

[0226] [Examples 58 to 64, Comparative Example 4] Organic light-emitting devices were fabricated in the same manner as in Example 57, except that the compounds shown in Table 12 were appropriately changed. The characteristics of the obtained devices were measured and evaluated in the same manner as in Example 57. The measurement results are shown in Table 12.

[0227] [Table 12]

[0228] Table 12 shows that the brightness degradation rate of the organic light-emitting element using comparative compound 1-a was 60%. This is because, when comparative compound 1-a is used as a guest, it has a high LUMO level and poor stability against oxygen. On the other hand, the element using the organic compound of this embodiment showed good durability characteristics. This is because the compound according to this embodiment has a condensed ring structure diazabolol skeleton, has a low LUMO level and high stability against oxygen.

[0229] Based on the above, the organic compound according to this embodiment is capable of blue light emission with high luminous efficiency, high color purity, and a deep LUMO level (far from the vacuum level). Therefore, when the organic compound according to this embodiment is used in an organic light-emitting device, an organic light-emitting device with excellent color purity, luminous efficiency, and durability can be provided. [Explanation of Symbols]

[0230] 1: Interlayer insulating layer, 2: First electrode, 3: Insulating layer, 4: Organic compound layer, 5: Second electrode, 6: Protective layer, 7: Color filter, 10: Sub-pixel, 11: Substrate, 12: Insulating layer, 13: Gate electrode, 14: Gate insulating film, 15: Semiconductor layer, 16: Drain electrode, 17: Source electrode, 18: TFT, 19: Insulating film, 20: Contact hole, 21: Anode, 22: Organic compound layer, 23: Cathode, 24: First protective layer, 25: Second protective layer, 26: Organic light-emitting element, 100: Display device< / x> < / l>

Claims

1. An organic compound characterized by the general formula [1] shown below. 【Chemistry 1】 (In general formula [1], R 1 From R 8 Each of these is 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 substituted or unsubstituted heteroaryloxy group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom. Ar 1 From Ar 4 Each of these is independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. L represents a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. X represents an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, N (Z), and C (W), respectively. 1 ) (W 2 Z is independently selected from ) . Z is independently 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, respectively. W 1 , W 2 Each of these is independently 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.

2. The organic compound according to claim 1, characterized by being represented by the following general formula [2-1] or [2-2]. 【Chemistry 2】 (In general formula [2-1] or [2-2], Y 1 to Y 5 is independently selected from C(A) and a nitrogen atom, respectively.) Each of the elements A is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

3. The organic compound according to claim 1, characterized by being represented by the following general formulas [3-1], [3-2], or [3-3]. 【Transformation 3】 (In general formulas [3-1], [3-2], or [3-3], Y 1 From Y 2 , Y 4 From Y 11 Each is independently selected from C(A) and nitrogen atoms. However, if at least one of the Y atoms belonging to one of the first Y group consisting of Y1 to Y2 and Y4 to Y6, and the second Y group consisting of Y7 to Y11, is a nitrogen atom, then at least one of the Y atoms belonging to the other Y group is a nitrogen atom. Each of the elements A is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom. Y 2 and Y 7 , Y 4 and Y 11 If C(A), then each A may be bonded to each other to form a ring.

4. The organic compound according to claim 1, characterized by being represented by the following general formulas [4-1], [4-2], [4-3], or [4-4]. 【Chemistry 4】 (In general formulas [4-1], [4-2], [4-3] or [4-4], Y 1 From Y 2 , Y 4 From Y 8 , Y 10 From Y 17 Each of these is independently selected from C(A) and nitrogen atoms. However, if at least one of the Y atoms belonging to one of the following Y groups is a nitrogen atom: the first Y group consisting of Y1 to Y2 and Y4 to Y6, the second Y group consisting of Y7 to Y8 and Y10 to Y12, and the third Y group consisting of Y13 to Y17, then at least one of the Y atoms belonging to each of the other two Y groups is a nitrogen atom. Each of the elements A is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom. In general formulas [4-1], [4-2], or [4-3], Y 2 and Y 7 , Y 4 and Y 11 , Y 8 and Y 13 , Y 10 and Y 17 If C(A), then each A may be bonded to each other to form a ring. In general formula [4-4], Y 2 and Y 12 , Y 4 and Y 10 , Y 8 and Y 13 , Y 10 and Y 17 If C(A), then each A may be bonded to each other to form a ring.

5. The organic compound according to claim 1, characterized by being represented by the following general formula [5-1] or [5-2]. 【Transformation 5】 (In general formula [5-1] or [5-2], Y 19 From Y 25 These are independently selected from C(A) and nitrogen atoms, respectively. Each of the elements A is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

6. The organic compound according to claim 1 or 2, characterized by being represented by the following general formula [6]. 【Transformation 6】 (In general formula [6], R 9 From R 12 Each of these is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

7. The organic compound according to claim 1 or 2, characterized by being represented by the following general formula [7]. 【Transformation 7】 (In general formula [7], R 9 From R 12 Each of these is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

8. The organic compound according to claim 1 or 2, characterized by being represented by the following general formula [8]. 【Transformation 8】 (In general formula [8], R 9 From R 12 Each of these is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

9. The organic compound according to claim 1 or 2, characterized by being represented by the following general formula [9]. 【Chemistry 9】 (In general formula [9], R 9 From R 12 Each of these is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

10. The organic compound according to claim 1 or 2, characterized by being represented by the following general formula [10]. 【Chemistry 10】 (In general formula [10], R 13 From R 14 Each of these is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

11. The organic compound according to claim 1 or 3, characterized by being represented by the following general formula [11]. 【Chemistry 11】 (In general formula [11], R 15 From R 22 Each of these is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom. R 16 and R 19 , R 18 and R 21 (These elements may also be joined to each other to form a ring.)

12. The organic compound according to claim 1 or 4, characterized by being represented by the following general formula [12]. 【Chemistry 12】 (In general formula [12], R 23 From R 34 Each of these is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom. R 24 and R 27 , R 26 and R 29 , R 28 and R 31 , R 30 and R 33 (These elements may also be joined to each other to form a ring.)

13. The organic compound according to claim 1 or 5, characterized by being represented by the following general formula [13]. 【Chemistry 13】 (In general formula [13], R 35 From R 40 Each of these is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom.

14. The organic compound according to claim 3, characterized by being represented by the following general formula [14]. 【Chemistry 14】 (In general formula [14], R 41 From R 44 Each of these is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a cyano group, a substituted or unsubstituted silyl group, and a deuterium atom. W 3 From W 4 Each of these is independently 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.

15. An organic light-emitting element having an anode, a cathode, and an organic compound layer disposed between the anode and the cathode, An organic light-emitting element characterized in that at least one layer of the organic compound layer has the organic compound described in any one of claims 1 to 14.

16. The organic light-emitting element according to claim 15, characterized in that the layer having the organic compound is a light-emitting layer.

17. The organic light-emitting element according to claim 16, further comprising another light-emitting layer arranged in lamination with the aforementioned light-emitting layer, wherein the other light-emitting layer emits a color different from the light-emitting color emitted by the aforementioned light-emitting layer.

18. A display device having a plurality of pixels, wherein at least one of the plurality of pixels is an organic light-emitting element according to any one of claims 15 to 17 and a transistor connected to the organic light-emitting element.

19. It comprises an optical unit having multiple lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays the image captured by the image sensor. The photoelectric conversion device is characterized in that the display unit has an organic light-emitting element as described in any one of claims 15 to 17.

20. An electronic device comprising: a display unit having an organic light-emitting element as described in any one of claims 15 to 17; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

21. A lighting device comprising a light source having an organic light-emitting element as described in any one of claims 15 to 17, and a light-diffusing section or optical filter that transmits light emitted by the light source.

22. A mobile body characterized by comprising a lamp having an organic light-emitting element as described in any one of claims 15 to 17, and a body on which the lamp is provided.

23. An exposure light source for an electrophotographic image forming apparatus, characterized by having an organic light-emitting element according to any one of claims 15 to 17.

Images