Organic compound and organic light-emitting element

Abstract

To provide an organic compound and an organic light-emitting element that are excellent in durability characteristics.SOLUTION: The invention provides an organic compound represented by general formula [1] which has specific substituents.SELECTED DRAWING: None

Description

[Technical field]

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

[0002] An organic light-emitting element (sometimes called an organic electroluminescent element or an organic EL element) is an electronic element having a pair of electrodes and an organic compound layer disposed between the electrodes. By injecting electrons and holes from the pair of electrodes, excitons of a light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting element emits light. Recent progress in organic light-emitting elements has been remarkable, and their features include low driving voltage, a variety of emission wavelengths, high-speed response, and the possibility of making light-emitting devices thinner and lighter. Incidentally, compounds suitable for organic light-emitting devices have been actively developed up to now. This is because the creation of compounds with excellent device life characteristics is important in providing high-performance organic light-emitting devices. As a compound that has been created so far, indolocarbazole derivative 1-a is described in Patent Document 1.

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

[0004] [Patent Document 1] US Patent Application Publication No. 2016 / 0233435 Summary of the Invention [Problem to be solved by the invention]

[0005] However, it is desired to further improve the durability of the organic light-emitting device containing the compound 1-a described in Patent Document 1. The present invention has been made in view of the above problems, and an object of the present invention is to provide an organic compound and an organic light-emitting device having excellent durability characteristics. [Means for solving the problem]

[0006] The organic compound according to the present invention is characterized by being represented by the following general formula [1] or [2].

[0007] [ka] In general formula [1], L1 and L2 each independently represent a direct bond or a linking group consisting of at least one selected from the group consisting of a substituted or unsubstituted benzene residue, a substituted or unsubstituted naphthalene residue, a substituted or unsubstituted phenanthrene residue, a substituted or unsubstituted triphenylene residue, and a substituted or unsubstituted compound residue represented by the following general formula [a]:

[0008] [ka] In general formula [a], X1 and X2 are each independently selected from O, S, Se, and Te. HAr1 is selected from groups represented by the following general formulae [b] to [d], and HAr2 is selected from groups represented by the following general formulae [e] to [g]. The groups represented by the general formulae [b] to [g] may further have a condensed ring.

[0009] [ka] In the general formulas [b] to [g], X3 to X 10 are each independently selected from O, S, Se, and Te. In formulae [b] to [d], * represents the bonding position with L1. In formulae [e] to [g], * represents the bonding position with L2 or H. R1 to R6 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group. n is 0 or 1.

[0010] [ka] In the general formula [2], L3 is a linking group composed of at least one selected from the group consisting of a substituted or unsubstituted benzene residue, a substituted or unsubstituted naphthalene residue, a substituted or unsubstituted phenanthrene residue, a substituted or unsubstituted triphenylene residue, and substituted or unsubstituted groups represented by the following general formulas [h] to [j]:

[0011] [ka] In the general formulas [h] to [j], X 11 ~X 14 are independently selected from O, S, Se, and Te. * indicates the bond position. R 11 ~R 28 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group. Effect of the Invention

[0012] The organic compound according to the present invention can provide an organic light-emitting device having excellent durability. [Brief description of the drawings]

[0013] [Figure 1] 1A is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention, and FIG. 1B is a schematic cross-sectional view showing an example of a display device using an organic light-emitting element according to one embodiment of the present invention. [Diagram 2] FIG. 1 is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention. [Diagram 3] 1A is a schematic diagram illustrating an example of an imaging device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of an electronic device according to an embodiment of the present invention. [Figure 4] 1A is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of a foldable display device. [Diagram 5] 1A is a schematic diagram showing an example of an illumination device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing an example of a moving body having a vehicle lamp according to an embodiment of the present invention. [Figure 6] 1A is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. [Figure 7] 1A is a schematic diagram illustrating an example of an image forming apparatus according to an embodiment of the present invention, and (b) and (c) are schematic diagrams illustrating an example of an exposure light source of the image forming apparatus according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] ≪Organic compounds≫ First, the organic compound according to the present embodiment will be described. The organic compound according to the present embodiment is represented by the following general formula [1] or [2].

[0015] <Organic compound represented by general formula [1]> [ka]

[0016] [L1,L2] In the general formula [1], L1 and L2 are each independently a direct bond or a linking group composed of at least one selected from the group consisting of a substituted or unsubstituted benzene residue, a substituted or unsubstituted naphthalene residue, a substituted or unsubstituted phenanthrene residue, a substituted or unsubstituted triphenylene residue, and a substituted or unsubstituted compound residue represented by the following general formula [a]. Here, the linking group is a group composed of one or more groups selected from the benzene residues, etc., and for example, in the exemplary compound A7 described later, the linking group L1 is composed of five benzene ring residues.

[0017] [ka]

[0018] In the general formula [a], X1 and X2 are each independently selected from O, S, Se, and Te. It is preferable that X1 and X2 are each independently selected from O and S.

[0019] It is preferable that L1 and L2 are each independently a direct bond or a linking group composed of at least one selected from the group consisting of a trivalent or less, preferably divalent or less, residue of a substituted or unsubstituted benzene, a trivalent or less, preferably divalent or less, residue of a substituted or unsubstituted naphthalene, a trivalent or less, preferably divalent or less, residue of a substituted or unsubstituted phenanthrene, a trivalent or less, preferably divalent or less, residue of a substituted or unsubstituted triphenylene, and a trivalent or less, preferably divalent or less, residue of a substituted or unsubstituted compound represented by the general formula [a].

[0020] Furthermore, it is preferable that L1 and L2 are each independently a linking group composed of at least one selected from the group consisting of a substituted or unsubstituted benzene residue, a substituted or unsubstituted naphthalene residue, a substituted or unsubstituted phenanthrene residue, and a substituted or unsubstituted triphenylene residue.

[0021] Moreover, the benzene residue is preferably a residue bonded at the meta position, and L1 and L2 are preferably linking groups composed of one or more metaphenylene groups.

[0022] Examples of the substituent that may be possessed by the residue constituting the linking group include a deuterium atom, a group represented by the following general formula [b], a heterocyclic group such as a group represented by the following general formula [c], etc., but are not limited thereto.

[0023] [HAr1, HAr2] In the general formula [1], HAr1 is selected from groups represented by the following general formulae [b] to [d], and HAr2 is selected from groups represented by the following general formulae [e] to [g]. HAr1 is preferably a group represented by the following general formula [c] or [d], and HAr2 is preferably a group represented by the following general formula [f] or [g].

[0024] [ka]

[0025] In the general formulas [b] to [g], X3 to X 10 are independently selected from O, S, Se, and Te. 10 are preferably independently selected from O and S.

[0026] In the general formulae [b] to [d], * indicates the bonding position to L1. In the general formulae [e] to [g], * indicates the bonding position to L2 or H.

[0027] The groups represented by the general formulae [b] to [d] are monovalent groups, and the bonding position* may be on any carbon atom. For example, in the group represented by the general formula [b], the bonding position* may be on any carbon atom constituting a five-membered ring or on any carbon atom constituting a six-membered ring. In addition, the groups represented by the general formulae [e] to [g] are divalent groups, and the two bonding positions* may be on any carbon atom. For example, in the group represented by the general formula [e], the two bonding positions* may be on one carbon atom constituting a five-membered ring and one carbon atom constituting a six-membered ring, or on only one of the carbon atoms constituting a five-membered ring and the carbon atom constituting a six-membered ring.

[0028] The groups represented by the general formulae [b] to [g] may further have a condensed ring, which may include, but is not limited to, aromatic rings such as a benzene ring, a naphthalene ring, or a phenanthrene ring, and aromatic heterocycles such as a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furan ring, a benzofuran ring, or a dibenzofuran ring.

[0029] [R1 to R6] In the general formula [1], R1 to R6 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group.

[0030] Examples of halogen atoms include, but are not limited to, fluorine, chlorine, bromine, iodine, astatine, tennessine, and the like.

[0031] The alkyl group may be an alkyl group having from 1 to 20 carbon atoms. Examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a tertiary pentyl group, a 3-methylpentan-3-yl group, a 1-adamantyl group, and a 2-adamantyl group.

[0032] The alkoxy group may be an alkoxy group having from 1 to 10 carbon atoms. Examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a tertiary butoxy group, a 2-ethyl-octyloxy group, and a benzyloxy group.

[0033] Examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0034] Examples of substituents that the alkyl group, alkoxy group, and silyl group may further have include deuterium, alkyl groups such as a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, and a tertiary butyl group; aralkyl groups such as a benzyl group; aryl groups such as a phenyl group and a biphenyl group; heterocyclic groups such as a pyridyl group and a pyrrolyl group; amino groups such as a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, and a ditolylamino group; alkoxy groups such as a methoxy group, an ethoxy group, and a propoxy group; aryloxy groups such as a phenoxy group; halogen atoms such as fluorine, chlorine, bromine, and iodine; and a cyano group, but are not limited to these.

[0035] [n] n is 0 or 1. It is preferable that n is 0.

[0036] <Organic compound represented by general formula [2]> [ka]

[0037] [L3] In the general formula [2], L3 is a linking group composed of at least one selected from the group consisting of a substituted or unsubstituted benzene residue, a substituted or unsubstituted naphthalene residue, a substituted or unsubstituted phenanthrene residue, a substituted or unsubstituted triphenylene residue, and a substituted or unsubstituted group represented by the following general formulas [h] to [j]. Here, the linking group is a group composed of one or more groups selected from the benzene residues, etc., and for example, in the exemplary compound D3 described later, the linking group L3 is composed of residues of two benzene rings.

[0038] [ka]

[0039] In the general formulas [h] to [j], X 11 ~X 14 are independently selected from O, S, Se, and Te. 11 ~X 14 are preferably independently selected from O and S.

[0040] In the general formulae [h] to [j], * represents a bonding position. The groups represented by the general formulae [h] to [j] are divalent groups, and the two bonding positions * may be on any of the carbon atoms. For example, in the group represented by the general formula [h], the two bonding positions * may be on one carbon atom constituting a five-membered ring and one carbon atom constituting a six-membered ring, or may be on only one of the carbon atoms constituting a five-membered ring and the carbon atom constituting a six-membered ring.

[0041] L3 is preferably a linking group composed of at least one selected from the group consisting of a trivalent or less, preferably divalent or less, residue of a substituted or unsubstituted benzene, a trivalent or less, preferably divalent or less, residue of a substituted or unsubstituted naphthalene, a trivalent or less, preferably divalent or less, residue of a substituted or unsubstituted phenanthrene, a trivalent or less, preferably divalent or less, residue of a substituted or unsubstituted triphenylene, and a substituted or unsubstituted group represented by any of the general formulae [h] to [j].

[0042] Examples of the substituent that may be contained in the group that constitutes the linking group include, but are not limited to, a deuterium atom.

[0043] [R 11 ~R 28 ] In the general formula [2], R 11 ~R 28 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group.

[0044] Examples of the alkyl group, alkoxy group, and silyl group include, but are not limited to, the groups described for R1 to R6. Examples of the substituent that the alkyl group, alkoxy group, and silyl group may further have include, but are not limited to, the groups described for R1 to R6.

[0045] <Features> The organic compound of this embodiment has the following characteristics. (1-1) At least one indolocarbazole unit and two heteroaryl groups at the terminal units of the molecule improve compatibility, improve charge and energy storage, and provide excellent durability. Or, at least one indolocarbazole unit and two heteroaryl groups at the terminal units of the molecule increase the permanent dipole moment of the molecule, providing excellent durability. (1-2) The two terminal units of the molecule are heteroaryl groups with hole-transporting properties, which improves the hole-transporting ability and provides excellent low driving voltage.

[0046] The following describes the properties of the basic skeleton of the organic compound according to this embodiment, with reference to a comparative compound having a structure similar to that of the organic compound according to this embodiment. Specifically, the comparative compound 1-a and the exemplary compound according to this embodiment are given.

[0047] (1-1) At least one indolocarbazole unit and two heteroaryl groups at the terminal units of the molecule improve compatibility, improve charge and energy storage, and provide excellent durability. Or, at least one indolocarbazole unit and two heteroaryl groups at the terminal units of the molecule increase the permanent dipole moment of the molecule, providing excellent durability.

[0048] The organic compound of this embodiment has an indolocarbazole unit. The indolocarbazole unit is characterized by high hole transport performance and high structural stability without a rotation axis. The compound represented by general formula [1] has one indolocarbazole unit. When n=0, the terminal units of the molecule are an indolocarbazole unit and HAr1, both of which are heteroaryl groups. When n=1, the terminal units of the molecule are HAr1 and HAr2, both of which are heteroaryl groups. On the other hand, the compound represented by general formula [2] has two indolocarbazole units. The terminal units of the molecule are indolocarbazole units and heteroaryl groups.

[0049] In inventing the organic compounds represented by the general formula [1] or [2], the inventors focused on the terminal units and permanent dipole moments of the molecules.

[0050] The organic layer of an organic light-emitting device, particularly the compounds in the light-emitting layer, repeatedly transition between the ground state and the excited state during the light emission process of the organic light-emitting device. In particular, in organic phosphorescent light-emitting devices, it is important to control the triplet excited state (T1), which accounts for 75% of the excited state. For example, it is necessary to promote efficient energy transfer from T1 of the host molecule to the guest molecule, and to efficiently emit light from the guest molecule. If the energy transfer efficiency is poor, the probability that the generated excitation energy will be used for reactions with adjacent molecules increases, causing deterioration of durability characteristics due to the generation of quencher molecules. It is known that the energy transfer process from T1 of the host molecule to the guest molecule occurs by Dexter energy transfer. In order to improve the efficiency of Dexter energy transfer, it is important to make the distance between the host molecule and the guest molecule as close as possible.

[0051] As a result of intensive research, the present inventors have found that it is effective to have at least one indolocarbazole unit and to have heteroaryl groups at two terminal units of the molecule in order to shorten the intermolecular distance between the host molecule and the guest molecule. The reason for this is believed to be that by arranging heteroatom units that favorably interact with the metal atom (e.g., iridium atom) of the guest molecule at both terminals of the molecule, the intermolecular interaction with the guest molecule becomes large, and the intermolecular distance becomes short. In order to shorten the intermolecular distance as much as possible, it is preferable that the terminal heteroaryl unit is unsubstituted. Specifically, in the compound represented by the general formula [1] and n=0, R1 to R6 are preferably hydrogen atoms. In the compound represented by the general formula [1] and n=1, HAr1 and HAr2 are unsubstituted, and therefore it is preferable. In the compound represented by the general formula [2], R 11 ~R 28 is preferably a hydrogen atom.

[0052] From another perspective, the heterocycle has a heteroatom in the skeleton, and thus has a characteristic of being highly polarized. In other words, the organic compound of this embodiment has a characteristic of being highly permanent dipole moment. Furthermore, host molecules with a large permanent dipole moment are preferable because they are compatible with highly polar guest molecules such as Ir complexes and Pt complexes. Table 1 shows the values ​​of the permanent dipole moment calculated by molecular orbital calculation and the number of terminal hetero units for the exemplary compounds B27 and E12 of this embodiment and the comparative compound 1-a. Furthermore, Table 1 shows the durability characteristics (luminance deterioration ratio) when used as a host for an organic light-emitting device in Examples (Examples 35, 53, Comparative Example 1).

[0053] [Table 1]

[0054] As shown in Table 1, in the example compounds B27 and E12, the terminal hetero units were increased and the dipole moment was also increased compared to the comparative compound 1-a, and thus the durability was improved.

[0055] From the above, by having at least one indolocarbazole unit and two terminal units of the molecule being heteroaryl groups, compatibility is improved, charge and energy storage are improved, and durability properties are excellent.Alternatively, by having at least one indolocarbazole unit and two terminal units of the molecule being heteroaryl groups, the permanent dipole moment of the molecule is high, resulting in excellent durability.

[0056] (1-2) The two terminal units of the molecule are heteroaryl groups with hole-transporting properties, which improves the hole-transporting ability and provides excellent low driving voltage.

[0057] The organic compound of this embodiment can be used in the hole transport layer, electron blocking layer, light emitting layer, other functional layers, etc. of the organic light emitting element, and is particularly suitable for use as a host for the light emitting layer. Furthermore, since the organic compound of this embodiment has a high T1 (lowest triplet excitation energy), it can be preferably used as a light emitting layer host for a system that uses a triplet excited state such as phosphorescence or delayed fluorescence for emission. Furthermore, since the organic compound of this embodiment has a shallow HOMO (highest occupied molecular orbital) (close to the vacuum level) and a high hole transport ability, it can be used in combination with an electron transport host.

[0058] The organic compound of the present embodiment has an indolocarbazole unit and is characterized by high hole transport performance. Here, in the compound represented by the general formula [2], two terminal units of the molecule are indolocarbazole units. However, in the compound represented by the general formula [1], at least one of the terminal units of the molecule is not an indolocarbazole unit, but HAr1 or HAr2. Therefore, it is preferable that the heteroaryl groups represented by HAr1 and HAr2 also have hole transport performance. For example, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, thianthrene, or units condensed with these can be mentioned. In addition, azines such as pyridine, pyrazine, pyrimidine, and triazine, azoles such as imidazole, oxazole, and thiazole, and ketone-containing units are electron transporting units and are not preferable because they have low hole transport performance. In the organic compound of this embodiment, HAr1 is selected from the groups represented by general formulas [b] to [d], and HAr2 is selected from the groups represented by general formulas [e] to [g].

[0059] Furthermore, in order to improve the mobility, it is preferable that the terminal heteroaryl unit is unsubstituted. Specifically, as described above, in the compound represented by the general formula [1] where n=0, R1 to R6 are preferably hydrogen atoms. In the compound represented by the general formula [1] where n=1, HAr1 and HAr2 are unsubstituted, which is preferable. In the compound represented by the general formula [2], R 11 ~R 28is preferably a hydrogen atom.

[0060] As described above, by having both an indolocarbazole unit and a hole-transporting heteroaryl group, the hole transporting ability is improved and mobility is improved, so that the voltage of the organic light-emitting device can be reduced. Furthermore, the greater the number of hole-transporting units arranged at the ends of the molecule, the greater the effect. For example, the organic light-emitting device of the examples (Example 35, Comparative Example 1) using Exemplary Compound B27 and Comparative Compound 1-a had a 100 mA / cm 2 The driving voltage was measured at this time, and the values ​​are shown in Table 2, assuming that the voltage in Comparative Example 1 was 1.0. As shown in Table 2, when comparing the two, it was found that the exemplary compound B27 was lower at 0.95.

[0061] [Table 2]

[0062] The permanent dipole moments in Tables 1 and 2 were calculated using molecular orbital calculations. The molecular orbital calculation method used was the density functional theory (DFT), which is currently widely used. The functional 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.

[0063] In the meantime, the snowflakes of the snowflakes are a bit of a snowflake. (1-3) All freely rotatable single bonds are sp 2 The carbon-carbon bonds provide high bond energy, improving the durability of the element. (1-4) In the general formula [1], when L1 and L2 are linking groups composed only of hydrocarbons, the effect of the terminal heteroaryl group can be enhanced. More preferably, when L1 and L2 are linking groups composed of one or more metaphenylene groups, T1 is increased, and the element efficiency and element durability are improved. (1-5) In the general formula [1], n is 0, whereby T1 becomes high, and the element efficiency and element durability are improved. These features are explained below.

[0064] (1-3) All freely rotatable single bonds are sp 2 The carbon-carbon bonds provide high bond energy, improving the durability of the element.

[0065] The organic layer of the organic light-emitting element, particularly the compound in the light-emitting layer, repeatedly transitions between the ground state and the excited state during the light-emitting process of the organic light-emitting element. In this process, intense molecular movements such as stretching, contraction, and rotation occur. At that time, if there is a site where the bond is easily dissociated, the bond may be cleaved and a part of the compound may be liberated. If a part of the compound is liberated, the structure will change, so if liberation is likely to occur, the durability of the compound will be reduced. In addition, when such a compound is used in an organic light-emitting element, the liberated part becomes a quencher and reduces the durability of the element. Therefore, the more the molecule has a structure that is less likely to dissociate and liberation to occur, the better the durability.

[0066] In the organic compound of this embodiment, all of the freely rotatable single bonds are sp 2 Since the compound is composed of carbon atoms, the bond is unlikely to be cleaved to cause separation, and the compound has high durability. Therefore, when the compound according to this embodiment is used in the organic layer of an organic light-emitting device, the bond is unlikely to be cleaved to cause separation during operation of the device, so that deterioration of the device is suppressed even when the device is operated for a long time, and an organic light-emitting device having excellent durability can be obtained.

[0067] (1-4) In the general formula [1], when L1 and L2 are linking groups composed only of hydrocarbons, the effect of the terminal heteroaryl group can be enhanced. More preferably, when L1 and L2 are linking groups composed of one or more metaphenylene groups, T1 is increased, and the element efficiency and element durability are improved.

[0068] As described in (1-1), the organic compound of this embodiment has improved compatibility with guest molecules due to the effect of the heteroatom at the end of the molecule. Therefore, if the units other than the end of the molecule are composed of units with low polarity, the effect of the polarity of the end of the molecule can be easily obtained. Therefore, it is preferable that L1 and L2 are linking groups composed only of hydrocarbons with low polarity. Specifically, it is preferable that L1 and L2 are each independently a linking group composed of at least one selected from the group consisting of a residue of substituted or unsubstituted benzene, a residue of substituted or unsubstituted naphthalene, a residue of substituted or unsubstituted phenanthrene, and a residue of substituted or unsubstituted triphenylene.

[0069] Furthermore, it is preferable that L1 and L2 are linking groups composed of one or more metaphenylene groups, since T1 is higher. For example, as shown in Table 3, exemplary compound B31, in which L1 is composed of two metaphenylene groups, has a higher T1 than comparative compound 1-a, in which L1 is composed of a heteroarylene group. High T1 increases the efficiency of energy transfer to guest molecules, improving device efficiency, and shortens the exciton lifetime, improving device durability. Note that T1 in Table 3 indicates the wavelength at which the peak rises when a single film is prepared and the emission spectrum is measured at 77K.

[0070] [Table 3]

[0071] (1-5) In the general formula [1], n is 0, whereby T1 becomes high, and the element efficiency and element durability are improved.

[0072] As described above, the organic compound of this embodiment is characterized by a high T1. Furthermore, among the organic compounds of this embodiment, the general formula [1] n=0 makes the T1 higher. The results of molecular orbital calculations are shown in Table 4. As shown in Table 4, for example, the exemplary compound B27 in the general formula [1] where n=0 has a higher T1 and improves the element efficiency and element durability, and is therefore preferable, compared to the exemplary compound E9 in the general formula [1] where n=1. Note that the T1 in Table 4 indicates the wavelength of the rise of the peak similar to that of the T1 in Table 3.

[0073] [Table 4]

[0074] In this specification, the HOMO and LUMO can be calculated using the ionization potential and band gap.

[0075] The HOMO can be estimated by measuring the ionization potential, which can be measured with a measuring device such as AC-3 after dissolving the compound to be measured in a solvent such as toluene, or after depositing the compound to be measured on a substrate such as glass.

[0076] The LUMO can be calculated using the band gap and ionization potential values. The LUMO can be estimated by subtracting the ionization potential value from the band gap. The band gap can be measured by dissolving the compound to be measured in a solvent such as toluene and irradiating it with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum of the excitation light. Alternatively, the band gap can be measured by depositing the compound to be measured on a substrate such as glass and irradiating the deposited film with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum where the deposited film absorbs the excitation light.

[0077] The LUMO can also be estimated from the reduction potential. For example, the one-electron reduction potential is estimated using cyclic volmetry (CV) measurements. CV measurements are performed, for example, in a 0.1 M tetrabutylammonium perchlorate solution in DMF, with a Ag / Ag reference electrode. + The measurement can be performed using a Pt counter electrode and a glassy carbon working electrode. The LUMO can be estimated by adding the difference between the reduction potential of the obtained compound and that of ferrocene, which is -4.8 eV.

[0078] <Example> Specific examples of the organic compound according to this embodiment are shown below, but this embodiment is not limited to these.

[0079] [ka]

[0080] [ka]

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] [ka]

[0088] Exemplary compounds belonging to Group A are compounds in which n = 0 and HAr1 is the formula [b] in formula [1]. Compounds in Group A have a small molecular weight and a low sublimation temperature, and therefore have the effect of increasing the margin of the sublimation temperature relative to the decomposition temperature.

[0089] Exemplary compounds belonging to group B are compounds in which n = 0 and HAr1 is the formula [c] in formula [1]. Since HAr1 has a condensed ring structure consisting of three or more rings, the compounds in group B have the effect of having high thermal stability and high T1.

[0090] Exemplary compounds belonging to group C are compounds in which n=0 in formula [1], HAr1 is formula [d], or L1 contains a residue of a compound represented by formula [a]. Compounds in group C have an ether or thioether bridged ring structure in L1-HAr1, and many unshared electron pairs of heteroatoms, so that they have a high compatibility effect.

[0091] An example compound belonging to group D is a compound represented by formula [2]. The compounds in group D have two indolocarbazole units, and have the effect of having high hole transport ability and higher hole mobility.

[0092] The exemplary compounds belonging to Group E are compounds in which n = 1 in formula [1]. The compounds in Group E have the effect of improving thermal stability due to their large molecular weight, and the effect of having a high permanent dipole moment.

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

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

[0095] In the organic light-emitting device of this embodiment, when the organic compound according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer consisting of only the organic compound according to this embodiment, or may be a layer consisting of the organic compound according to this embodiment and other compounds. Here, when the light-emitting layer is a layer consisting of the organic compound according to this embodiment and other compounds, the organic compound according to this embodiment may be used as a host of the light-emitting layer or may be used as a guest. It may also be used as an assist material that can be contained in the light-emitting layer. The organic compound of this embodiment can be suitably used as a light-emitting layer host of a system using a triplet excited state such as phosphorescence or delayed fluorescence for light emission. Therefore, it is preferable that the light-emitting layer further contains a phosphorescent light-emitting compound. In addition, the organic compound of this embodiment can be used by mixing with an electron-transporting host. Therefore, it is preferable that the light-emitting layer further contains an electron-transporting compound. Here, the host is a compound having the largest mass ratio among the compounds constituting the light-emitting layer. In addition, the guest is a compound having a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer, and is a compound that is responsible for the main light emission. In addition, the assist material is a compound having a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer, and assists the light emission of the guest. The assist material is also called a second host. The host material can also be called a first compound, and the assist material can also be called a second compound.

[0096] The host concentration of the light-emitting layer according to this embodiment is preferably 10% by mass or more and 90% by mass or less, more preferably 20% by mass or more and 80% by mass or less, and even more preferably 30% by mass or more and 70% by mass or less, based on the total amount of the constituent materials of the light-emitting layer. The guest concentration relative to the host is 0.01% by mass or more and 50% by mass or less, preferably 0.1% by mass or more and 20% by mass or less, based on the total amount of the constituent materials of the light-emitting layer. From the viewpoint of suppressing concentration quenching, the guest concentration is particularly preferably 10% by mass or less.

[0097] The guest may be uniformly contained throughout the layer in which the host is the matrix, or may be contained with a concentration gradient.The guest may also be contained partially in a specific region within the layer, so that the light-emitting layer has a region containing only the host and no guest.

[0098] The light-emitting layer of this embodiment may be a single layer or multiple layers, and it is also possible to mix colors by including a light-emitting material having another light-emitting color. Multiple layers means a state in which the light-emitting layer and another light-emitting layer are laminated. In this case, the light-emitting color of the organic light-emitting element is not particularly limited. More specifically, it may be white or an intermediate color. In the case of white, for example, if the light-emitting layer emits blue light, the other light-emitting layer emits a color different from blue, that is, green or red. In addition, the film formation method is also performed by deposition or coating film formation. Furthermore, a third light-emitting layer that emits blue light and a charge generation layer may be provided between the light-emitting layer or the laminated light-emitting layer in this embodiment and the first or second electrode. The charge generation layer exerts the function as a tandem element, and the electrons generated from the charge generation layer and the holes injected from the first electrode are charge-recombined to generate excitons, and the holes generated from the charge generation layer and the electrons injected from the second electrode are charge-recombined to form excitons. As a result, the internal quantum efficiency is doubled. In this case, the organic light-emitting element of this embodiment can be applied to one side of a tandem element as a yellow light-emitting layer, which is a complementary color to the blue light-emitting layer. Therefore, a white light-emitting element can be provided by forming a tandem element with a blue light-emitting layer using a stacked light-emitting layer made of the light-emitting layer of this embodiment. The third light-emitting layer contains at least a third organic compound and a fourth organic compound. The third organic compound is a host material, and the fourth organic compound is a blue light-emitting material.

[0099] A specific example of the device configuration of the organic light-emitting device of this embodiment is a multi-layer device configuration in which an electrode layer and an organic compound layer as shown in (1) to (6) below are sequentially laminated on a substrate. In any device configuration, the organic compound layer necessarily includes a light-emitting layer having a light-emitting material. (1) Anode / light-emitting layer / cathode (2) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (3) Anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (4) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode (5) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (6) Anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode However, these device configuration examples are merely very basic device configurations, and are not limited to these. For example, various layer configurations can be adopted, such as providing an insulating layer, an adhesive layer, or an interference layer at the interface between the electrode and the organic compound layer, forming an electron transport layer or a hole transport layer from two layers having different ionization potentials, forming an emitting layer from two layers made of different emitting materials, and so on.

[0100] Among the device configurations shown in (1) to (6) above, the configuration (6) is preferred since it has both an electron blocking layer and a hole blocking layer. In other words, in the configuration (6) having an electron blocking layer and a hole blocking layer, both hole and electron carriers can be reliably confined within the light-emitting layer, resulting in an organic light-emitting device with no carrier leakage and high light-emitting efficiency. Here, in the organic light-emitting device of this embodiment, the first organic compound and the second organic compound constituting the light-emitting layer are all carbon-carbon bonds, preferably sp 2 It is preferably composed of carbon-carbon bonds. In other words, it is preferably composed of a host material with high planarity. As a result, the hole transporting ability and electron transporting ability are higher than those of a general organic light-emitting device. This allows the electron blocking layer and the hole blocking layer to play an important role. For example, since the hole blocking layer needs to be stable against holes, it is preferable that the hole blocking layer compound is an organic compound with low reactivity, and furthermore, an organic compound consisting only of hydrocarbons. For example, since the electron blocking layer also needs to be stable against electrons, it is preferable that the electron blocking layer compound is an organic compound with low reactivity, and furthermore, all of the freely rotatable single bonds are carbon-carbon bonds, preferably sp 2 It is preferably an organic compound consisting of carbon-carbon bonds.

[0101] The mode of extraction (element form) of the light output from the light emitting layer may be a so-called bottom emission type in which light is extracted from the electrode on the substrate side, or a so-called top emission type in which light is extracted from the opposite side of the substrate. Also, a double-sided extraction type in which light is extracted from the substrate side and the opposite side of the substrate can be adopted.

[0102] The organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer constituting the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not particularly limited. More specifically, it may be white or a neutral color.

[0103] <Other compounds> In the organic light-emitting device according to this embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. can be used together as necessary. Examples of these compounds are given below.

[0104] As the hole injection transport material, a material having high hole mobility is preferable so that the injection of holes from the anode can be easily performed and the injected holes can be transported to the light emitting layer. In addition, a material having a high glass transition temperature is preferable so as to suppress deterioration of the film quality such as crystallization in the organic light emitting device. Examples of low molecular weight and high molecular weight materials having hole injection transport performance include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above hole injection transport material is also preferably used in the electron blocking layer. Specific examples of compounds used as the hole injection transport material are shown below, but of course, the present invention is not limited to these.

[0105] [ka]

[0106] Examples of luminescent materials mainly involved in luminescence function include condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Specific examples of compounds used as luminescent materials are shown below, but are of course not limited to these.

[0107] [ka]

[0108] [ka]

[0109] The light-emitting layer host or light-emitting assist material contained in the light-emitting layer may contain a compound other than the organic compound of this embodiment as a third component. Examples of the third component include aromatic hydrocarbon compounds or derivatives thereof, carbazole derivatives, azine derivatives, xanthone derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organic aluminum complexes such as tris(8-quinolinolato)aluminum, and organic beryllium complexes.

[0110] [ka]

[0111] The electron transporting material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected in consideration of the balance with the hole mobility of the hole transporting material. Examples of materials having electron transporting properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organic aluminum complexes, and condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the electron transporting material is also preferably 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.

[0112] [ka]

[0113] The electron injection material can be selected from those that can easily inject electrons from the cathode, and is selected in consideration of the balance with hole injection properties. Organic compounds include n-type dopants and reducing dopants. For example, compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, acridine derivatives, etc. can also be used in combination with the above-mentioned electron transport materials.

[0114] <Configuration of organic light-emitting element> The organic light-emitting element is provided by forming a first electrode, an organic compound layer, and a second electrode on a substrate. An insulating layer may be provided on the substrate. A protective layer, a color filter, a microlens, etc. may be provided on the second electrode. When a color filter is provided, a planarizing layer may be provided between the protective layer. The planarizing layer may be made of acrylic resin, etc. The same applies when a planarizing layer is provided between the color filter and the microlens. Either the first electrode or the second electrode may be an anode, and the other may be a cathode.

[0115] [substrate] Examples of the substrate include quartz, glass, silicon wafer, resin, and metal. In addition, a switching element such as a transistor and wiring may be provided on the substrate, and an insulating layer may be provided thereon. As the insulating layer, any material can be used as long as it can form a contact hole so that wiring can be formed between the first electrode and the insulating layer, and insulation from wiring that is not connected can be ensured. For example, resin such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0116] [electrode] A pair of electrodes can be used. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. It can also be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0117] The material constituting the anode should have as large a work function as possible. For example, metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, mixtures containing these metals, alloys combining these metals, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0118] These electrode materials may be used alone or in combination of two or more kinds. The anode may be composed of one layer or multiple layers.

[0119] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. The above materials can also function as a reflective film without serving as an electrode. When used as a transparent electrode, a transparent conductive layer of oxide such as indium tin oxide (ITO) or indium zinc oxide can be used, but is not limited to these. Photolithography technology can be used to form the electrode.

[0120] On the other hand, the material for the cathode should have a small work function. Examples of the material include alkali metals such as lithium, alkaline earth metals such as calcium, aluminum, titanium, manganese, silver, lead, chromium, and other metals or mixtures containing these metals. Alternatively, alloys combining these metals can be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver, and the like can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials may be used alone or in combination of two or more types. The cathode may have a single layer structure or a multi-layer structure. Among these, it is preferable to use silver, and it is even more preferable to use a silver alloy to reduce the aggregation of silver. As long as the aggregation of silver can be reduced, the ratio of the alloy is not important. For example, the ratio of silver to other metals may be 1:1, 3:1, and the like.

[0121] 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 it is more preferable to use a direct current or alternating current sputtering method, etc., since the film coverage is good and the resistance can be easily reduced.

[0122] [Organic compound layer] The organic compound layer may be formed as a single layer or as multiple layers. When the organic compound layer has multiple layers, it may be called a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, or an electron injection layer depending on its function. The organic compound layer is mainly composed of an organic compound, but may contain inorganic atoms or inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, or the like. The organic compound layer may be disposed between the first electrode and the second electrode, or may be disposed in contact with the first electrode and the second electrode.

[0123] The organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light emitting device according to one embodiment of the present invention are formed by the method shown below.

[0124] The organic compound layer constituting the organic light-emitting device according to one embodiment of the present invention can be formed by dry processes such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively, instead of the dry process, a wet process can be used in which the compound is dissolved in an appropriate solvent and a layer is formed by a known coating method (e.g., spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, capillary coating, nozzle coating, LB method, etc.). Among them, the vacuum deposition, ionization deposition, inkjet printing, nozzle coating, etc. are suitable for manufacturing a large-area organic light-emitting device.

[0125] Here, when the layer is formed by a vacuum deposition method or a solution coating method, crystallization is unlikely to occur and the layer has excellent stability over time. When the layer is formed by a coating method, the layer can be formed by combining with a suitable binder resin.

[0126] Examples of the binder resin include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0127] These binder resins may be used alone as homopolymers or copolymers, or in combination of two or more kinds. If necessary, known additives such as plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.

[0128] The thickness of each layer in the organic light-emitting device is usually preferably 1 nm to 10 μm, and particularly preferably 10 nm to 100 nm in thickness of the light-emitting layer of the organic compound layer in order to obtain effective light-emitting characteristics.

[0129] [Protective layer] A protective layer may be provided on the second electrode. For example, by bonding glass provided with a moisture absorbent on the second electrode, it is possible to reduce the intrusion of water and the like into the organic compound layer and reduce 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 the like into the organic compound layer. For example, after the second electrode is formed, it may be transported to another chamber without breaking the vacuum, and a silicon nitride film having a thickness of 2 μm may be formed by the CVD method to serve as a protective layer. A protective layer may be provided using an atomic deposition method (ALD method) after the film is formed by the CVD method. The material of the film formed by the ALD method is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed by the CVD method on the film formed by the ALD method. The film formed by the ALD method may have a smaller thickness than the film formed by the CVD method. Specifically, it may be 50% or less, or even 10% or less.

[0130] [Color Filter] A color filter may be provided on the protective layer. For example, a color filter taking into consideration the size of the organic light-emitting element may be provided on another substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using a photolithography technique. The color filter may be made of a polymer.

[0131] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing unevenness of the layer below. It may also be called a material resin layer without limiting the purpose. The planarization layer may be composed of an organic compound, and may be either a low molecular weight or a high molecular weight, but is preferably a high molecular weight.

[0132] The planarization layer may be provided above and below the color filter, and may be made of the same or different materials.Specific examples of the materials include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0133] [Microlens] The organic light-emitting element may have an optical member such as a microlens on its light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be intended to increase the amount of light extracted from the organic light-emitting element and control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the tangent and the hemisphere are the vertices of the microlens. The vertex of the microlens can be determined in the same manner in any cross-sectional view. That is, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the tangent and the semicircle are the vertices of the microlens.

[0134] It is also possible to define the midpoint of the microlens. In the cross section of the microlens, a line segment is imaginary from a point where an arc shape ends to a point where another arc shape ends, and the midpoint of the line segment can be called the midpoint of the microlens. The cross section for determining the vertex and midpoint may be a cross section perpendicular to the insulating layer.

[0135] [Opposite substrate] A counter substrate may be provided on the planarization layer. The counter substrate is called a counter substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is a first substrate, the counter substrate may be a second substrate.

[0136] [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 controls the emission of the first light-emitting element and the second light-emitting element independently. The active matrix type circuit may be a voltage programming circuit or a current programming circuit. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission luminance of the light-emitting element, a transistor that controls the emission timing, a capacitance that holds the gate voltage of the transistor that controls the emission luminance, and a transistor for connecting to GND without going through the light-emitting element.

[0137] The light emitting device has a display region and a peripheral region arranged around the display region. The display region has a pixel circuit, and the peripheral region has a display control circuit. The mobility of a transistor constituting the pixel circuit may be smaller than the mobility of a transistor constituting the display control circuit. The slope of the current-voltage characteristic of the transistor constituting the pixel circuit may be smaller than the slope of the current-voltage characteristic of the transistor constituting the display control circuit. The slope of the current-voltage characteristic can be measured by the so-called Vg-Ig characteristic. The transistor constituting the pixel circuit is a transistor connected to a light emitting element, such as a first light emitting element.

[0138] [Pixels] An organic light emitting device having an organic light emitting element may have a plurality of pixels, each of which has sub-pixels that emit different colors, for example, each of which may have one of the RGB emission colors.

[0139] The pixel emits light in an area also called the pixel aperture. This area is the same as the first area. 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 the subpixels may be 10 μm or less, more specifically, it may be 8 μm, 7.4 μm, 6.4 μm.

[0140] The pixels may have a known arrangement in plan view. For example, they may be a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in plan view may be any known shape. For example, they may be a rectangle, a quadrangle such as a diamond, or a hexagon. Of course, if the shape is not an exact figure but is close to a rectangle, it is included in the rectangle. The shape of the subpixels and the pixel arrangement may be used in combination.

[0141] <Applications of organic light-emitting devices> The organic light-emitting device according to the present embodiment can be used as a component of a display device or a lighting device, and can also be used as an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, a light-emitting device having a white light source and a color filter, etc.

[0142] The display device may be an image information processing device having an image input unit for inputting image information from an area CCD, a linear CCD, a memory card, or the like, an information processing unit for processing the input information, and displaying the input image on a display unit. The display device may have a plurality of pixels, at least one of which may have the organic light-emitting element of this embodiment and an active element such as a transistor connected to the organic light-emitting element. In this case, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate. The image display device has an input unit for inputting image information and a display unit for outputting an image, and the display unit has the display device of this embodiment.

[0143] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of the touch panel function may be an infrared type, a capacitance type, a resistive film type, or an electromagnetic induction type, and is not particularly limited. The display device may be used in the display unit of a multifunction printer.

[0144] Next, the display device according to the present embodiment will be described with reference to the drawings. Fig. 1 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).

[0145] FIG. 1(a) is a schematic cross-sectional view of 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 according to their light emission. The emitted light 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 edge 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.

[0146] A transistor and a capacitor may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode 2 may be electrically connected via a contact hole or the like (not shown).

[0147] The insulating layer 3 is also called a bank or a pixel separation film. It covers the ends of the first electrodes 2 and is disposed so as to surround the first electrodes 2. The portions where the insulating layer 3 is not disposed are in contact with the organic compound layer 4 and become light-emitting regions.

[0148] The organic compound layer 4 includes a hole injection layer 41 , a hole transport layer 42 , a light emitting layer 43 , a hole blocking layer 44 , and an electron transport layer 45 .

[0149] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode. The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. The protective layer 6 is illustrated as being a single layer, but may be a multi-layer. Each layer may be an inorganic compound layer and an organic compound layer.

[0150] The color filters 7 are divided into 7R, 7G, and 7B according to their colors. The color filters 7 may be formed on a planarization film (not shown). Also, a resin protective layer (not shown) may be provided on the color filters 7. Also, the color filters 7 may be formed on the protective layer 6. Alternatively, the color filters 7 may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0151] The display device 100 in Fig. 1(b) has an organic light-emitting element 26 and a TFT 18, which is an example of a transistor. A substrate 11 made of glass, silicon, or the like, and an insulating layer 12 are provided thereon. An active element such as the TFT 18 is disposed on the insulating layer 12, and a gate electrode 13 of the active element, a gate insulating film 14, and a semiconductor layer 15 are provided thereon. The TFT 18 has a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on the upper part of the TFT 18. An anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film 19.

[0152] The electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the embodiment shown in Fig. 1(b). In other words, it is sufficient that either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT 18.

[0153] 1(b), the organic compound layer 22 is illustrated as a single layer, but the organic compound layer 22 may be a multi-layer. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26.

[0154] In the display device 100 of FIG. 1(b), transistors are used as switching elements, but other switching elements such as MIM elements may be used instead.

[0155] The transistor used in the display device 100 of Fig. 1(b) is not limited to a thin film transistor having an active layer on an insulating surface of a substrate, but may be a transistor using a single crystal silicon wafer. Examples of the active layer include single crystal silicon, amorphous silicon, non-single crystal silicon such as 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.

[0156] The transistors included in the display device 100 of Fig. 1(b) may be formed in a substrate such as a Si substrate. Here, "formed in a substrate" means that the substrate itself such as a Si substrate is processed to produce the transistors. In other words, having a transistor in a substrate can be seen as the substrate and the transistor being integrally formed.

[0157] The organic light-emitting element according to this embodiment has its light emission brightness controlled by a TFT, which is an example of a switching element, and by providing the organic light-emitting element on a plurality of surfaces, an image can be displayed based on the respective light emission brightnesses. The switching element according to this embodiment is not limited to a TFT, and may be a transistor formed of low-temperature polysilicon, or an active matrix driver formed on a substrate such as a Si substrate. On the substrate may also be within the substrate. Whether to provide a transistor within the substrate or to use a TFT is selected according to the size of the display unit. For example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0158] 2 is a schematic diagram showing an example of a display device according to the present 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 FPC1002 and 1004 are connected to the touch panel 1003 and the display panel 1005. A transistor is printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position if the display device is a portable device.

[0159] The display device according to this embodiment may have color filters having red, green, and blue colors, the red, green, and blue colors being arranged in a delta arrangement.

[0160] The display device according to the present embodiment may be used as a display unit of a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include mobile phones such as smartphones, tablets, and head-mounted displays.

[0161] The display device according to the present embodiment may be used as a display unit of an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device, or may be a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0162] 3(a) is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may have 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 this case, the display device may display not only an image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the moving speed of the subject, the possibility that the subject will be blocked by an obstruction, and the like.

[0163] Since the timing suitable for imaging is short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment. This is because the organic light-emitting element has a fast response speed. Display devices using organic light-emitting elements are required to have a high display speed, and these devices can be used more preferably than liquid crystal display devices.

[0164] The imaging device 1100 has an optical section (not shown). The optical section has a plurality of lenses, which form an image on an imaging element housed in a housing 1104. The focus of the plurality of lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may be called a photoelectric conversion device. The photoelectric conversion device can include an imaging method that does not capture images sequentially, but detects the difference from the previous image, cuts out an image from an image that is always recorded, and the like.

[0165] FIG. 3(b) is a schematic diagram showing an example of an electronic device according to the present embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit 1202 may be a biometric recognition unit that recognizes a fingerprint and performs unlocking or the like. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an image sensor. An image captured by the camera function is displayed on the display unit 1201. Examples of the electronic device 1200 include a smartphone and a notebook computer.

[0166] FIG. 4 is a schematic diagram showing an example of a display device according to the present embodiment. FIG. 4(a) shows 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 light-emitting element according to the present embodiment may be used in the display unit 1302. The display device 1300 has the frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. 4(a). The lower side of the frame 1301 may also serve as the base. The frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0167] FIG. 4(b) is a schematic diagram showing another example of the display device according to the present embodiment. The display device 1310 in FIG. 4(b) is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have a light-emitting element according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be one display unit without a joint. The first display unit 1311 and the second display unit 1312 can be separated at the bending point. The first display unit 1311 and the second display unit 1312 may display different images, or the first and second display units may display one image.

[0168] FIG. 5(a) is a schematic diagram showing an example of a lighting device according to the present embodiment. The lighting device 1400 may have a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusion unit 1405. The light source 1402 may have an organic light-emitting element according to the present 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 of the light source, such as for lighting up, and deliver the light over a wide range. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the lighting. If necessary, a cover may be provided on the outermost part.

[0169] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white, neutral white, or any other color from blue to red. It may have a dimming circuit that adjusts the light intensity and a color adjusting circuit that adjusts the emitted color. 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 into DC voltage. The lighting device may have an inverter circuit. Moreover, white has a color temperature of 4200K, and neutral white has a color temperature of 5000K. The lighting device may have a color filter.

[0170] The lighting device according to the present embodiment may also include a heat dissipation section that dissipates heat from within the device to the outside, and examples of the heat dissipation section include metals with high specific heat, liquid silicon, and the like.

[0171] 5B is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has tail lamps, which are an example of a lamp. The automobile 1500 has tail lamps 1501, and may be configured to turn on the tail lamps when braking or the like is performed.

[0172] The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp 1501 may have a protective member for protecting the organic light-emitting element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0173] The automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display unless it is a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials of the electrodes and the like of the organic light-emitting element are made of transparent members.

[0174] The moving body according to the present embodiment may be a ship, an aircraft, a drone, or the like. The moving body may have a body and a lamp provided on the body. The lamp may emit light to indicate the position of the body. The lamp has the organic light-emitting element according to the present embodiment.

[0175] An application example of the display device of each of the above-mentioned embodiments will be described with reference to Fig. 6. The display device can be applied to a system that can be worn as a wearable device such as smart glasses, HMD, and smart contacts. An image capturing and display device used in such an application example has an image capturing device capable of photoelectrically converting visible light, and a display device capable of emitting visible light.

[0176] Fig. 6(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using Fig. 6(a), glasses 1600 (smart glasses) according to one application example will be described. An imaging device 1602 such as a CMOS sensor or SPAD is provided on the front side of a lens 1601 of the glasses 1600. In addition, a display device according to each of the above-mentioned embodiments is provided on the back side of the lens 1601.

[0177] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the image capture device 1602 and the display device. The control device 1603 also controls the operations of the image capture device 1602 and the display device. The lens 1601 is formed with an optical system for focusing light on the image capture device 1602.

[0178] FIG. 6(b) is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 6(b), glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 have a control device 1612, and the control device 1612 is equipped with an imaging device corresponding to the imaging device 1602 in FIG. 6(a) and a display device. The lens 1611 is formed with an imaging device in the control device 1612 and an optical system for projecting light emitted from the display device, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operations of the imaging device and the display device.

[0179] The control device 1612 may have a gaze detection unit that detects the gaze of the wearer. Infrared light may be used to detect the gaze. The infrared light emitting unit emits infrared light to the eyeball of the user gazing at the display image. The image capturing unit having a light receiving element detects the reflected light of the emitted infrared light from the eyeball to obtain an image of the eyeball. By providing a reduction means for reducing the light from the infrared light emitting unit to the display unit in a planar view, the deterioration of image quality is reduced. The gaze of the user to the display image is detected from the image of the eyeball obtained by capturing 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 a Purkinje image due to reflection of irradiated light on the cornea can be used. More specifically, gaze detection processing based on a pupil-corneal reflex method is performed. Using the pupil-corneal reflex method, a gaze vector representing the direction (rotation angle) of the eyeball is calculated based on the image of the pupil and the Purkinje image included in the image of the eyeball, thereby detecting the gaze of the user.

[0180] A display device according to an embodiment of the present invention may have an imaging device having a light receiving element, and may control a display image of the display device based on the user's line of sight information from the imaging device. Specifically, the display device determines a first field of view area to which the user gazes and a second field of view area other than the first field of view area based on the line of sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be received from an external control 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.

[0181] The display area includes a first display area and a second display area different from the first display area, and an area having a high priority is determined from the first display area and the second display area based on line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. The resolution of the area having a high priority may be controlled to be higher than the resolution of areas other than the area having a high priority. In other words, the resolution of an area having a relatively low priority may be lowered.

[0182] AI may be used to determine the first field of view area and the area with high priority. The AI ​​may be a model configured to estimate the angle of the line of sight and the distance to an object at the end of the line of sight from the image of the eyeball, using the image of the eyeball and the direction in which the eyeball in the image was actually looking as teacher data. The AI ​​program may be included in the display device, the imaging device, or an external device. If included in the external device, it is transmitted to the display device via communication.

[0183] When display control is performed based on visual recognition detection, the present invention is preferably applicable to smart glasses that further include an imaging device for capturing images of the outside world. The smart glasses can display captured outside information in real time.

[0184] FIG. 7(a) is a schematic diagram showing an example of an image forming apparatus according to an embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus, and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 includes an organic light-emitting element according to this embodiment. The developing unit 31 includes a toner, etc. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0185] 7(b) and 7(c) are diagrams showing the exposure light source 28, and are schematic diagrams showing a state in which a plurality of light-emitting units 36 are arranged on a long substrate. The arrow 37 is a direction parallel to the axis of the photoconductor, and represents the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the axis direction about which the photoconductor 27 rotates. This direction can also be called the long axis direction of the photoconductor 27. FIG. 7(b) shows a form in which the light-emitting units 36 are arranged along the long axis direction of the photoconductor 27. FIG. 7(c) shows a form different from FIG. 7(b), in which the light-emitting units 36 are alternately arranged in the column direction in each of the first column and the second column. The first column and the second column are arranged at different positions in the row direction. In the first column, a plurality of light-emitting units 36 are arranged at intervals. In the second column, the light-emitting units 36 are arranged at positions corresponding to the intervals between the light-emitting units 36 in the first column. That is, a plurality of light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in FIG. 7(c) can also be described as a grid-like arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0186] As described above, the use of the device using the organic light-emitting element according to this embodiment makes it possible to display images with good image quality and stable display even over a long period of time. In addition, the use of the device using the organic light-emitting element according to this embodiment makes it possible to achieve both good visibility outdoors and power-saving display due to highly efficient and high-luminance light output.

[0187] ≪Included components≫ The disclosure of this embodiment includes the following configuration. (Configuration 1) An organic compound characterized by being represented by general formula [1] or [2]. In the general formula [1], L1 and L2 each independently represent a direct bond or a linking group consisting of at least one selected from the group consisting of a substituted or unsubstituted benzene residue, a substituted or unsubstituted naphthalene residue, a substituted or unsubstituted phenanthrene residue, a substituted or unsubstituted triphenylene residue, and a substituted or unsubstituted residue of a compound represented by the general formula [a]. In general formula [a], X1 and X2 are each independently selected from O, S, Se, and Te. HAr1 is selected from groups represented by general formulae [b] to [d], and HAr2 is selected from groups represented by general formulae [e] to [g]. The groups represented by general formulae [b] to [g] may further have a condensed ring. In the general formulas [b] to [g], X3 to X 10 are each independently selected from O, S, Se, and Te. In formulae [b] to [d], * represents the bonding position with L1. In formulae [e] to [g], * represents the bonding position with L2 or H. R1 to R6 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group. n is 0 or 1. In the general formula [2], L3 is a linking group composed of at least one selected from the group consisting of a substituted or unsubstituted benzene residue, a substituted or unsubstituted naphthalene residue, a substituted or unsubstituted phenanthrene residue, a substituted or unsubstituted triphenylene residue, and a substituted or unsubstituted group represented by any of the general formulae [h] to [j]. In the general formulas [h] to [j], X 11 ~X 14 are independently selected from O, S, Se, and Te. * indicates the bond position. R 11~R 28 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group. (Configuration 2) In the general formula [1], L1 and L2 each independently represent a direct bond or a linking group composed of at least one selected from the group consisting of a trivalent or less residue of a substituted or unsubstituted benzene, a trivalent or less residue of a substituted or unsubstituted naphthalene, a trivalent or less residue of a substituted or unsubstituted phenanthrene, a trivalent or less residue of a substituted or unsubstituted triphenylene, and a trivalent or less residue of a substituted or unsubstituted compound represented by the general formula [a]; In the general formula [2], L3 is a linking group consisting of at least one selected from the group consisting of a trivalent or less residue of a substituted or unsubstituted benzene, a trivalent or less residue of a substituted or unsubstituted naphthalene, a trivalent or less residue of a substituted or unsubstituted phenanthrene, a trivalent or less residue of a substituted or unsubstituted triphenylene, and a substituted or unsubstituted group represented by the general formulas [e] to [g]. The organic compound according to structure 1. (Configuration 3) In the general formula [1], each of L1 and L2 is independently a linking group consisting of at least one selected from the group consisting of a substituted or unsubstituted benzene residue, a substituted or unsubstituted naphthalene residue, a substituted or unsubstituted phenanthrene residue, and a substituted or unsubstituted triphenylene residue. The organic compound according to structure 1 or 2. (Configuration 4) 4. The organic compound according to any one of structures 1 to 3, wherein the benzene residue is a residue bonded at a meta position. (Configuration 5) 5. The organic compound according to any one of structures 1 to 4, wherein in the general formula [1], L1 and L2 are linking groups each composed of one or more metaphenylene groups. (Configuration 6) 6. The organic compound according to any one of structures 1 to 5, wherein in the general formula [1], n is 0. (Configuration 7) The organic compound according to any one of structures 1 to 6, characterized in that, in the general formula [1], HAr1 is a group represented by the general formula [c], and HAr2 is a group represented by the general formula [f]. (Configuration 8) The organic compound according to any one of structures 1 to 6, characterized in that, in the general formula [1], HAr1 is a group represented by the general formula [d], and HAr2 is a group represented by the general formula [g]. (Configuration 9) In the general formula [1], R1 to R6 are hydrogen atoms, and in the general formula [2], R 11 ~R 28 9. The organic compound according to any one of structures 1 to 8, wherein is a hydrogen atom.

[0188] (Configuration 10) An organic light-emitting element having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein at least one layer of the organic compound layer contains the organic compound according to any one of Structures 1 to 9. (Configuration 11) 11. The organic light-emitting device according to configuration 10, wherein the organic compound layer has a light-emitting layer, and the light-emitting layer has the organic compound. (Configuration 12) 12. The organic light-emitting device according to claim 11, wherein the light-emitting layer further comprises a phosphorescent compound. (Configuration 13) 13. The organic light-emitting device according to claim 11 or 12, wherein the light-emitting layer further comprises an electron-transporting compound. (Configuration 14) 14. The organic light-emitting element according to any one of structures 11 to 13, further comprising another light-emitting layer disposed in a stacked manner with the light-emitting layer, the another light-emitting layer emitting a color different from the color of light emitted by the light-emitting layer. (Configuration 15) 15. The organic light-emitting device according to claim 14, which emits white light.

[0189] (Configuration 16) A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising an organic light-emitting element according to any one of structures 10 to 15 and a transistor connected to the organic light-emitting element. (Configuration 17) an optical unit having a plurality of lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays an image captured by the image sensor; 16. A photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to any one of configurations 10 to 15. (Configuration 18) An electronic device comprising: a display unit having the organic light-emitting element according to any one of structures 10 to 15; a housing in which the display unit is provided; and a communication unit provided in the housing and configured to communicate with the outside. (Configuration 19) 16. An illumination device comprising: a light source having the organic light-emitting element according to any one of configurations 10 to 15; and a light diffusion section or an optical filter that transmits light emitted by the light source. (Configuration 20) A moving body comprising: a lighting fixture having the organic light-emitting element according to any one of configurations 10 to 15; and a body on which the lighting fixture is provided. (Configuration 21) A photoconductor and an exposure light source for exposing the photoconductor, 16. An image forming apparatus, wherein the exposure light source has the organic light-emitting element according to any one of configurations 10 to 15. EXAMPLES

[0190] The present invention will be described below with reference to examples, although the present invention is not limited thereto.

[0191] [Example 1 (Synthesis of Exemplary Compound B27)] [ka]

[0192] The following reagents and solvents were placed in a 500 ml recovery flask. Compound G1: 1.00g (3.63mmol) Compound G2: 1.40g (3.63mmol) Pd(OAc)2: 25 mg (0.11 mmol) s-phos: 163 mg (0.36 mmol) K3PO4: 1.54g (7.26mmol) Toluene: 30 ml Water: 1ml

[0193] Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred at this temperature (90°C) for 5 hours. After the reaction was completed, methanol was added and filtration was performed to obtain a crude product as a residue. This was purified by silica gel column chromatography (chlorobenzene) and recrystallized with xylene to obtain 907mg (yield: 65%) of exemplary compound B27.

[0194] Exemplary compound B27 was subjected to mass spectrometry using MALDI-TOF-MS (Autoflex LRF, manufactured by Bruker). [MALDI-TOF-MS] Measured value: m / z=500 Calculated value: C 36 H 21 NS=500

[0195] [Examples 2 to 28 (Synthesis of Exemplary Compounds)] Exemplary compounds were synthesized in the same manner as in Example 1, except that raw material G1 in Example 1 was replaced with raw material 1, and raw material G2 was replaced with raw material 2. However, in Examples 22 to 24, the molar ratio of raw material 1 to raw material 2 was changed to raw material 1:raw material 2=2:1. Raw materials 1 and 2 in each Example are shown in Tables 5 to 8. In addition, the actual measured values: m / z of the mass spectrometry results measured in the same manner as in Example 1 are shown in Tables 5 to 8.

[0196] [Table 5]

[0197] [Table 6]

[0198] [Table 7]

[0199] [Table 8]

[0200] [Example 29] An organic light-emitting device of bottom emission type structure was produced by sequentially forming 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 on a substrate.

[0201] First, an ITO film was formed on a glass substrate, and the desired patterning process was performed to form an ITO electrode (anode). At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed was used as an ITO substrate in the following process. Next, a 1.33×10 -4 The organic compound layer and the electrode layer shown in Table 9 were successively formed on the ITO substrate by vacuum deposition using resistance heating in a vacuum chamber at 1000 Pa. Note that at this time, the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was 3 mm 2 It was made so that:

[0202] [Table 9]

[0203] The characteristics of the obtained device were measured and evaluated. The maximum external quantum efficiency (EQE) of the light-emitting device was 13%. Furthermore, at a current density of 100 mA / cm 2 A continuous driving test was performed at 100° C., and the time when the luminance degradation rate reached 5% was measured. When the time when the luminance degradation rate of Comparative Example 1 reached 5% was taken as 1.0, the luminance degradation rate ratio of this example was 1.3.

[0204] In this example, the measuring device was a microammeter 4140B manufactured by Hewlett-Packard Company to measure the current-voltage characteristics, and a BM7 manufactured by Topcon Corporation to measure the luminance.

[0205] [Examples 30 to 52, Comparative Example 1] An organic light-emitting device was produced in the same manner as in Example 29, except that the compounds were appropriately changed to those shown in Table 10. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 29. The measurement results are shown in Table 10.

[0206] [Table 10]

[0207] As described above, when the exemplary compound according to the present embodiment is used, since it has an indolocarbazole unit and the two ends of the molecule are heteroaryl units, the compatibility with guest molecules is improved, the intermolecular distance is shortened, and the energy transfer efficiency is increased. Therefore, a highly efficient element with excellent durability can be provided. [Explanation of symbols]

[0208] 1: interlayer insulating layer, 2: first electrode, 3: insulating layer, 4: organic compound layer, 5: second electrode, 6: protective layer, 7: color filter, 10: subpixel, 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

Claims

1. An organic compound represented by the following general formula [1] or [2]: 【Chemistry 1】 In the general formula [1], L 1 , L 2 are each independently a direct bond or a linking group composed of at least one selected from the group consisting of a residue of a substituted or unsubstituted benzene, a residue of a substituted or unsubstituted naphthalene, a residue of a substituted or unsubstituted phenanthrene, a residue of a substituted or unsubstituted triphenylene, and a residue of a substituted or unsubstituted compound represented by the following general formula [a]: 【Chemistry 2】 In the general formula [a], X 1 , X 2 are each independently selected from O, S, Se, and Te. H.A.R. 1 is selected from groups represented by the following general formulas [b] to [d], 2 is selected from the groups represented by the following general formulae [e] to [g]: The groups represented by the general formulae [b] to [g] may further have a condensed ring. 【Chemistry 3】 In the general formulas [b] to [g], X 3 ~X 10 are each independently selected from O, S, Se, and Te. In the general formulas [b] to [d], * represents L 1 In the general formulae [e] to [g], * represents the bonding position with L 2 or represents the bonding position with H. R 1 ~R 6 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group. n is 0 or 1. 【Chemistry 4】 In the general formula [2], L 3 is a linking group composed of at least one selected from the group consisting of a substituted or unsubstituted benzene residue, a substituted or unsubstituted naphthalene residue, a substituted or unsubstituted phenanthrene residue, a substituted or unsubstituted triphenylene residue, and substituted or unsubstituted groups represented by the following general formulas [h] to [j]: 【Chemistry 5】 In the general formulas [h] to [j], X 11 ~X 14 are independently selected from O, S, Se and Te. * represents a bonding position. R 11 ~R 28 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group.

2. In the general formula [1], the L 1 , L 2 each independently represents a direct bond or a linking group composed of at least one selected from the group consisting of a trivalent or less residue of a substituted or unsubstituted benzene, a trivalent or less residue of a substituted or unsubstituted naphthalene, a trivalent or less residue of a substituted or unsubstituted phenanthrene, a trivalent or less residue of a substituted or unsubstituted triphenylene, and a trivalent or less residue of a substituted or unsubstituted compound represented by the general formula [a], In the general formula [2], the L 3 is a linking group composed of at least one selected from the group consisting of a trivalent or lower residue of a substituted or unsubstituted benzene, a trivalent or lower residue of a substituted or unsubstituted naphthalene, a trivalent or lower residue of a substituted or unsubstituted phenanthrene, a trivalent or lower residue of a substituted or unsubstituted triphenylene, and a substituted or unsubstituted group represented by any of the general formulae [h] to [j].

3. In the general formula [1], the L 1 , L 2 are each independently a linking group consisting of at least one selected from the group consisting of a substituted or unsubstituted benzene residue, a substituted or unsubstituted naphthalene residue, a substituted or unsubstituted phenanthrene residue, and a substituted or unsubstituted triphenylene residue.

4. 3. The organic compound according to claim 1, wherein the benzene residue is a residue bonded at the meta position.

5. In the general formula [1], the L 1 , L 2 The organic compound according to claim 3, characterized in that is a linking group composed of one or more metaphenylene groups.

6. 3. The organic compound according to claim 1, wherein, in the general formula [1], n is 0.

7. In the general formula [1], 1 is a group represented by the general formula [c], and 2 is a group represented by the general formula [f].

8. In the general formula [1], 1 is a group represented by the general formula [d], 2 is a group represented by the general formula [g].

9. In the general formula [1], the R 1 ~R 6 is a hydrogen atom, and in the general formula [2], 11 ~R 28 3. The organic compound according to claim 1, wherein: is a hydrogen atom.

10. 3. An organic light-emitting element having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein at least one layer of the organic compound layer contains the organic compound according to claim 1.

11. The organic light-emitting element according to claim 10 , wherein the organic compound layer has a light-emitting layer, and the light-emitting layer has the organic compound.

12. The organic light-emitting device according to claim 11, wherein the light-emitting layer further comprises a phosphorescent compound.

13. The organic light-emitting device according to claim 12 , wherein the light-emitting layer further comprises an electron-transporting compound.

14. The organic light-emitting element according to claim 11, further comprising another light-emitting layer disposed in a stacked manner with the light-emitting layer, the another light-emitting layer emitting light of a color different from the color of light emitted by the light-emitting layer.

15. The organic light-emitting device according to claim 14, which emits white light.

16. A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to claim 10 and a transistor connected to the organic light-emitting element.

17. an optical unit having a plurality of lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays an image captured by the image sensor; The photoelectric conversion device according to claim 10 , wherein the display section comprises the organic light-emitting element according to claim 10 .

18. 11. An electronic device comprising: a display section having the organic light-emitting element according to claim 10; a housing in which the display section is provided; and a communication section provided in the housing for communicating with an external device.

19. 11. A lighting device comprising: a light source having the organic light-emitting element according to claim 10; and a light diffusion section or an optical filter that transmits light emitted by the light source.

20. A moving body comprising: a lighting device having the organic light-emitting element according to claim 10; and a body on which the lighting device is provided.

21. A photoconductor and an exposure light source for exposing the photoconductor, 11. An image forming apparatus, comprising: an exposure light source having the organic light emitting element according to claim 10.

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