Organic compound and organic light-emitting element

Abstract

This organic compound is represented by general formula [1]. L1 and L2 are linking groups composed of at least one selected from the group consisting of a directly bonded or a substituted or unsubstituted benzene residue, a residue of a substituted or unsubstituted compound represented by general formula [a], and the like. In general formula [a], X1 and X2 are selected from O, S, and the like. HAr1 is selected from the groups represented by general formulae [b] to [d], and HAr2 is selected from the groups represented by general formulae [e] to [g]. In general formulae [b] to [g], X3 to X10 are selected from O, S, and the like. In general formulae [b] to [d], * represents a bonding position with L1. In general formulae [e] to [g], * represents a bonding position with L2 or H. R1 to R6 are each independently selected from a hydrogen atom, a deuterium atom, and the like. n represents 0 or 1.

Description

Organic compound and organic light-emitting device

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

[0002] An organic light-emitting device (sometimes referred to as an organic electroluminescent device or organic EL device) is an electronic device having a pair of electrodes and an organic compound layer disposed between the electrodes. By injecting electrons and holes from the pair of electrodes, excitons of a light-emitting organic compound in the organic compound layer are generated, and the organic light-emitting device emits light when the excitons return to the ground state. Recent advances in organic light-emitting devices have been remarkable, with key features including low driving voltage, a wide range of emission wavelengths, fast response, and the ability to reduce the thickness and weight of light-emitting devices.

[0003] Incidentally, there has been active research to date into compounds suitable for organic light-emitting devices. 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.

[0004]

[0005] US Patent Application Publication No. 2016 / 0233435

[0006] However, further improvement in durability is desired for the organic light-emitting device containing the compound 1-a described in Patent Document 1.

[0007] 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 that are excellent in durability.

[0008] The organic compound according to the present invention is characterized by being represented by the following general formula [1] or [2].

[0009]

[0010] In the general formula [1], L １ , L ２are 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]:

[0011]

[0012] In the general formula [a], X １ , X ２ are each independently selected from O, S, Se, and Te.

[0013] H.A.R. １ is selected from groups represented by the following general formulas [b] to [d], and HAr ２ 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.

[0014]

[0015] In the general formulae [b] to [g], X ３ ~X １０ are each independently selected from O, S, Se, and Te. In 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.

[0016] 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.

[0017] n is 0 or 1.

[0018]

[0019] In the general formula [2], L ３is 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]:

[0020]

[0021] In the general formulae [h] to [j], X １１ ~X １４ are independently selected from O, S, Se, and Te. * represents a bonding position.

[0022] 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.

[0023] The organic compound according to the present invention can provide an organic light-emitting device with excellent durability.

[0024] FIG. 1 is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention. FIG. 2 is a schematic cross-sectional view of an example of a display device using an organic light-emitting element according to one embodiment of the present invention. FIG. 3 is a schematic view showing an example of a display device according to one embodiment of the present invention. FIG. 4 is a schematic view showing an example of an imaging device according to one embodiment of the present invention. FIG. 5 is a schematic view showing an example of an electronic device according to one embodiment of the present invention. FIG. 6 is a schematic view showing an example of a display device according to one embodiment of the present invention. FIG. 7 is a schematic view showing an example of a bendable display device. FIG. 8 is a schematic view showing an example of an illumination device according to one embodiment of the present invention. FIG. 9 is a schematic view showing an example of a moving body having a vehicle lamp according to one embodiment of the present invention. FIG. 10 is a schematic view showing an example of a wearable device according to one embodiment of the present invention. FIG. 11 is a schematic view showing another example of a wearable device according to one embodiment of the present invention. FIG. 12 is a schematic view showing an example of an image forming apparatus according to one embodiment of the present invention. FIG. 13 is a schematic view showing an example of an exposure light source of an image forming apparatus according to one embodiment of the present invention. FIG. 14 is a schematic view showing an example of an exposure light source of an image forming apparatus according to one embodiment of the present invention.

[0025] <Organic Compound> First, the organic compound according to this embodiment will be described. The organic compound according to this embodiment is represented by the following general formula [1] or [2].

[0026] <Organic compound represented by general formula [1]>

[0027]

[0028] [L １ , L ２ In the general formula [1], L １ , L ２ are each independently 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]. Here, the linking group is a group formed by bonding one or more groups selected from benzene residues, etc. For example, in Exemplary Compound A7 described later, the linking group L １ is composed of five benzene ring residues.

[0029]

[0030] In the general formula [a], X １ , X ２ are each independently selected from O, S, Se, and Te. １ , X ２ are preferably independently selected from O and S.

[0031] L １ , L ２ are preferably 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].

[0032] Also, L １ , L ２ are preferably 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.

[0033] The benzene residue is preferably a residue bonded at the meta position, and L １ , L ２ is preferably a linking group composed of one or more metaphenylene groups.

[0034] Examples of the substituent that may be possessed by the residue constituting the linking group include, but are not limited to, 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], and the like.

[0035] [HAr １ , H.A.R. ２ In the general formula [1], HAr １ is selected from groups represented by the following general formulas [b] to [d], and HAr ２ is selected from groups represented by the following general formulas [e] to [g]: １ is preferably a group represented by the following general formula [c] or [d], ２ is preferably a group represented by the following general formula [f] or [g]:

[0036]

[0037] In the general formulae [b] to [g], X ３ ~X １０ are each independently selected from O, S, Se, and Te. ３ ~X １０ are preferably independently selected from O and S.

[0038] In the general formulas [b] to [d], * represents L １ In the general formulae [e] to [g], * represents the bonding position with L ２or represents the bonding position with H.

[0039] The groups represented by general formulas [b] to [d] are monovalent groups, and the bonding position * may be on any carbon atom. For example, in the group represented by general formula [b], the bonding position * may be on either a carbon atom constituting a five-membered ring or a carbon atom constituting a six-membered ring. Furthermore, the groups represented by general formulas [e] to [g] are divalent groups, and the two bonding positions * may be on either carbon atoms. For example, in the group represented by 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 one carbon atom constituting a six-membered ring.

[0040] The groups represented by general formulas [b] to [g] may further have a fused ring, which may include, but is not limited to, aromatic rings such as a benzene ring, a naphthalene ring, and a phenanthrene ring, and aromatic heterocycles such as a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furan ring, a benzofuran ring, and a dibenzofuran ring.

[0041] [R １ ~R ６ In the general formula [1], 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.

[0042] Examples of halogen atoms include, but are not limited to, fluorine, chlorine, bromine, iodine, astatine, tennessine, and the like.

[0043] The alkyl group may be an alkyl group having from 1 to 20 carbon atoms, such as, but 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.

[0044] The alkoxy group may be an alkoxy group having from 1 to 10 carbon atoms, including, but not limited to, a methoxy group, an ethoxy group, a propoxy group, an isopropyloxy group, a tertiary butoxy group, a 2-ethyl-octyloxy group, and a benzyloxy group.

[0045] Examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0046] Examples of substituents that the alkyl group, alkoxy group, and silyl group may further have include, but are not limited to, 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.

[0047] [n] n is 0 or 1. n is preferably 0.

[0048] <Organic compound represented by general formula [2]>

[0049]

[0050] [L ３ In the general formula [2], L ３is 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 substituted or unsubstituted groups represented by the following general formulas [h] to [j]. Here, the linking group is a group formed by bonding one or more groups selected from the benzene residues, etc. For example, in the exemplary compound D3 described later, the linking group L ３ is composed of two benzene ring residues.

[0051]

[0052] In the general formulae [h] to [j], X １１ ~X １４ are each independently selected from O, S, Se, and Te. １１ ~X １４ are preferably independently selected from O and S.

[0053] In general formulas [h] to [j], * represents a bonding position. The groups represented by general formulas [h] to [j] are divalent groups, and the two bonding positions * may be on either carbon atom. For example, in the group represented by general formula [h], the two bonding positions * may be on one carbon atom constituting the five-membered ring and one carbon atom constituting the six-membered ring, or may be on only one of the carbon atoms constituting the five-membered ring and the carbon atom constituting the six-membered ring.

[0054] L ３ 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].

[0055] 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.

[0056] [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.

[0057] Examples of the alkyl group, alkoxy group, and silyl group include R １ ~R ６ Examples of the substituent that the alkyl group, alkoxy group, and silyl group may further have include, but are not limited to, groups such as those described above. １ ~R ６ Examples of the groups include, but are not limited to, those described above.

[0058] <Features> The organic compound of this embodiment has the following features. (1-1) Having at least one indolocarbazole unit and two terminal units of the molecule being heteroaryl groups improves compatibility, improves charge and energy accumulation, and provides excellent durability. Alternatively, having at least one indolocarbazole unit and two terminal units of the molecule being heteroaryl groups increases the permanent dipole moment of the molecule, providing excellent durability. (1-2) Having two terminal units of the molecule being heteroaryl groups with hole-transporting properties improves hole transport ability, providing excellent low driving voltage.

[0059] These characteristics of the basic skeleton of the organic compound according to this embodiment will be explained below with reference to comparative compounds having structures similar to those of the organic compound according to this embodiment. Specifically, comparative compound 1-a and exemplary compounds according to this embodiment will be mentioned.

[0060] (1-1) Having at least one indolocarbazole unit and two terminal units of the molecule being heteroaryl groups improves compatibility, improves charge and energy accumulation, and provides excellent durability. Alternatively, having at least one indolocarbazole unit and two terminal units of the molecule being heteroaryl groups increases the permanent dipole moment of the molecule, providing excellent durability. The organic compound of this embodiment has an indolocarbazole unit. The indolocarbazole unit is characterized by high hole transport performance and high structural stability due to the absence of 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 HAr １ and both are heteroaryl groups. When n=1, the terminal unit of the molecule is HAr １ And, H.A.R. ２ Both 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.

[0061] In inventing the organic compounds represented by the general formula [1] or [2], the present inventors focused on the terminal units and permanent dipole moments of the molecules.

[0062] The organic layer of an organic light-emitting device, 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 device. In particular, in an organic phosphorescent light-emitting device, the triplet excited state (T １ It is important to control the T １ It is necessary to promote efficient energy transfer from the host molecule to the guest molecule, and to efficiently emit light from the guest molecule. If the energy transfer efficiency is poor, the generated excitation energy is more likely to be used in reactions with adjacent molecules, which leads to the generation of quencher molecules, resulting in a deterioration in durability. １The energy transfer process from the host molecule to the guest molecule is known to occur via Dexter energy transfer. To improve the efficiency of Dexter energy transfer, it is important to minimize the distance between the host molecule and the guest molecule.

[0063] As a result of extensive research, the present inventors have found that, in order to reduce the intermolecular distance between a host molecule and a guest molecule, it is effective to have at least one indolocarbazole unit and to have heteroaryl groups at two terminal units of the molecule. This is believed to be because, by arranging heteroatom units that favorably interact with a metal atom (e.g., an iridium atom) of a guest molecule at both terminals of the molecule, the intermolecular interaction with the guest molecule increases, thereby reducing the intermolecular distance. In order to reduce the intermolecular distance as much as possible, it is preferable that the terminal heteroaryl units are unsubstituted. Specifically, a compound represented by general formula [1] where n=0 can be obtained by disposing R １ ~R ６ is preferably a hydrogen atom. The compound represented by the general formula [1] where n=1 is HAr １ , H.A.R. ２ is unsubstituted, which is preferable. The compound represented by the general formula [2] is １１ ~R ２８ is preferably a hydrogen atom.

[0064] From another perspective, heterocycles have a heteroatom in the skeleton, which is characterized by increased polarization. In other words, the organic compound of this embodiment is characterized by a large 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 permanent dipole moment calculated by molecular orbital calculation and the number of terminal hetero units for exemplary compounds B27 and E12 of this embodiment and comparative compound 1-a. Furthermore, Table 1 shows the durability characteristics (luminance degradation rate) when used as a host for organic light-emitting devices in Examples (Examples 35 and 53, Comparative Example 1).

[0065]

[0066] As shown in Table 1, exemplary compounds B27 and E12 had an increased number of terminal hetero units and a higher dipole moment than comparative compound 1-a, and thus exhibited improved durability.

[0067] As described above, by having at least one indolocarbazole unit and two heteroaryl groups at the terminal units of the molecule, compatibility is improved, charge and energy accumulation is improved, and durability is excellent. Alternatively, by having at least one indolocarbazole unit and two heteroaryl groups at the terminal units of the molecule, the permanent dipole moment of the molecule is high, resulting in excellent durability.

[0068] (1-2) When two terminal units of the molecule are heteroaryl groups with hole transporting properties, the hole transporting ability is improved and the driving voltage is excellent. 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 device, and is particularly suitable for use as a host for the light emitting layer. Furthermore, the organic compound of this embodiment has T １ Since the organic compound of this embodiment has a high triplet excited state energy (lowest triplet excited state energy), it can be suitably used as a host for an emission layer in a system that uses a triplet excited state for emission, such as phosphorescence or delayed fluorescence. 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.

[0069] The organic compound of this embodiment has an indolocarbazole unit and is characterized by high hole transporting performance. Here, the compound represented by general formula [2] has two indolocarbazole units at its terminal units. However, the compound represented by general formula [1] has at least one of the terminal units of the molecule being not an indolocarbazole unit but an HAr １ or HAr ２ Therefore, HAr １ , H.A.R. ２It is preferable that the heteroaryl group represented by the formula (I) also has hole transporting properties. Examples thereof include furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, thianthrene, and units formed by condensing these rings. Note that azine-based units such as pyridine, pyrazine, pyrimidine, and triazine, azole-based units such as imidazole, oxazole, and thiazole, and ketone-containing units are electron-transporting units and are not preferred because they have low hole transporting properties. Therefore, in the organic compound of this embodiment, HAr １ is selected from groups represented by general formulas [b] to [d], and HAr ２ is selected from groups represented by general formulas [e] to [g].

[0070] Furthermore, in order to improve mobility, it is preferable that the terminal heteroaryl unit is unsubstituted. Specifically, as described above, the compound represented by the general formula [1] where n=0 is R １ ~R ６ is preferably a hydrogen atom. The compound represented by the general formula [1] where n=1 is HAr １ , H.A.R. ２ is unsubstituted, which is preferable. The compound represented by the general formula [2] is １１ ~R ２８ is preferably a hydrogen atom.

[0071] As described above, by having both an indolocarbazole unit and a hole-transporting heteroaryl group, the hole transport 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 devices of Examples (Example 35, Comparative Example 1) using Exemplary Compound B27 and Comparative Compound 1-a exhibited a 100 mA / cm ２ The driving voltage was measured at this time, and the values ​​are shown in Table 2, with the voltage of Comparative Example 1 being taken as 1.0. As shown in Table 2, when the two were compared, it was found that Exemplified Compound B27 had a lower driving voltage of 0.95.

[0072]

[0073] 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 function was 6-31G. ＊Thanks for watching, it's a nice place to stayるfingernail nine(fingernail nine,six THIS 01, 100,000,000 THIS, CHASE, CHASE Yes, ROCKS, ROCKS feelings ,ShanaShana,ShaShanaSay,MYS THIS, THIS IS YOUR FAVORITE The sight, the smile, the sight, the snowflake, snowflake, snow Yes, scientists, scientists, THIS, THIS IS, THIS IS, THIS. The snow, the smile, the smile, THIS IS, THIS IS, THIS ANNAI, THIS THING, THIS THING snow,20,000,000,000 Thanks, smile, CHAN,D FAMILIES, POPE, POST Emotional, scientific, scientific Yes, I love you, I love you FASHIONA, DAHAFASHION, WAY Thanks, smile, smile,. THIS, THIS IS YOUR LIFE, THIS THIS, THIS IS, THIS IS, THIS, THIS IS THE LIFE, THIS THIS IS YOUR FAVORITE, YOUR FAVORITE, ASHASI, CHARISM, CHASE Yes, I love it, I love it ,poetry,potheographic, AN IMAGINATION, THIS YOU CAN smile, smile, smile It is, scientifically, scientifically AND YOUTH, THIS THINGS, THIS FAIR, THIS, THIS, THIS IS GOOD THIS,20100) is the best place to stay Thanks for watching the rest of the snowflakes.

[0074] Furthermore, the organic compound of this embodiment preferably has the following characteristics: (1-3) All freely rotatable single bonds are sp ２ By using carbon-carbon bonds, the bond energy is high, and the durability of the element is improved. １ , L ２ However, by using a linking group consisting of only hydrocarbons, the effect of the terminal heteroaryl group can be enhanced. １ , L ２ is a linking group composed of one or more metaphenylene groups, so that T １ (1-5) When n is 0 in the general formula [1], T １ This increases the efficiency and durability of the device.

[0075] These features will be explained below.

[0076] (1-3) All freely rotatable single bonds are sp ２ The carbon-carbon bond provides high bond energy, improving device durability. The organic layer of an organic light-emitting device, 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 device. During this transition, intense molecular movements such as stretching, contraction, and rotation occur. If a site where the bond is easily dissociated exists, the bond may be cleaved, resulting in the liberation of a portion of the compound. The liberation of a portion of the compound changes the structure, and the compound's durability decreases if liberation is likely to occur. Furthermore, when such a compound is used in an organic light-emitting device, the liberated portion acts as a quencher, reducing device durability. Therefore, molecules with a structure that makes bond dissociation and liberation less likely to occur have better durability.

[0077] In the organic compound of this embodiment, all of the freely rotatable single bonds are sp ２Since the compound is composed of carbon atoms, the bond cleavage hardly occurs, resulting in high durability. Therefore, when the compound according to this embodiment is used in the organic layer of an organic light-emitting device, the bond cleavage hardly occurs during operation of the device, so that deterioration of the device is suppressed even when the device is operated for a long time, resulting in an organic light-emitting device with excellent durability.

[0078] (1-4) In the general formula [1], L １ , L ２ However, by using a linking group consisting of only hydrocarbons, the effect of the terminal heteroaryl group can be enhanced. １ , L ２ is a linking group composed of one or more metaphenylene groups, so that T １ 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 more easily obtained. Therefore, L １ , L ２ is preferably a linking group composed only of hydrocarbons with low polarity. １ , L ２ are preferably 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.

[0079] Furthermore, L １ , L ２ is a linking group composed of one or more metaphenylene groups, １ For example, as shown in Table 3, １ However, the exemplary compound B31, which is composed of two metaphenylene groups, has a higher L １ T than the comparative compound 1-a which is composed of a heteroarylene group. １ is high. １The high T in Table 3 increases the efficiency of energy transfer to guest molecules, improving the device efficiency and shortening the exciton lifetime, thereby improving the device durability. １ prepared a single film and measured the emission spectrum at 77K, and showed the wavelength at which the peak rose.

[0080]

[0081] (1-5) In the general formula [1], n is 0, so that T １ As described above, the organic compound of this embodiment has a T １ Furthermore, among the organic compounds of this embodiment, when n=0 in the general formula [1], T １ The results of the molecular orbital calculation are shown in Table 4. As shown in Table 4, for example, the exemplary compound B27 in which n = 0 in the general formula [1] has a higher T than the exemplary compound E9 in which n = 1 in the general formula [1]. １ This is preferable because it has a high T value, which improves the element efficiency and element durability. １ is the T in Table 3 １ The wavelength of the peak rise was similar to that of the

[0082]

[0083] In this specification, the HOMO and LUMO can be calculated using the ionization potential and band gap.

[0084] The HOMO can be estimated by measuring the ionization potential, which can be measured using a measuring device such as an 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.

[0085] 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.

[0086] The LUMO can also be estimated from the reduction potential. For example, the one-electron reduction potential is estimated using CV (cyclic volmetry) measurement. CV measurement is performed, for example, in a 0.1 M tetrabutylammonium perchlorate solution in DMF, and a Ag / Ag reference electrode is used. ＋ Measurements can be made using a Pt counter electrode and a glassy carbon working electrode. The LUMO can be estimated by adding -4.8 eV, the difference between the reduction potential of the obtained compound and that of ferrocene.

[0087] <Specific Examples> Specific examples of the organic compound according to this embodiment are shown below, but this embodiment is not limited to these.

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] The exemplary compounds belonging to group A are those represented by the formula [1], where n=0 and HAr １ The compounds of 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.

[0098] The exemplary compounds belonging to group B are those represented by the formula [1], where n=0 and HAr １ The compounds of group B are compounds represented by formula [c]. １ However, since it has a fused ring structure consisting of three or more rings, it has high thermal stability and T １ This also has the effect of being highly

[0099] The exemplary compounds belonging to group C are those represented by the formula [1], where n=0 and HAr １ is formula [d], or L １ The compounds of group C are compounds containing a residue of a compound represented by formula [a]. １ -HAr １ Since the compound contains a ring structure of an ether or thioether bridge and has many unshared electron pairs of heteroatoms, it has the effect of providing high compatibility.

[0100] An example compound belonging to Group D is a compound represented by formula [2]. Compounds in Group D have two indolocarbazole units, and exhibit the effect of high hole transport ability and higher hole mobility.

[0101] The exemplary compounds belonging to Group E are compounds in which n = 1 in formula [1]. The compounds in Group E have an increased molecular weight, which results in improved thermal stability, and a high permanent dipole moment.

[0102] <Organic Light-Emitting Element> Next, the organic light-emitting element of this embodiment will be described. The organic light-emitting element 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 element of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has a light-emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, etc. Furthermore, the light-emitting layer may be a single layer or a laminate consisting of multiple layers.

[0103] 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.

[0104] In the organic light-emitting device of this embodiment, when the organic compound according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer consisting solely of the organic compound according to this embodiment, or may be a layer consisting of the organic compound according to this embodiment and other compounds. Here, when the light-emitting layer is a layer consisting of the organic compound according to this embodiment and other compounds, the organic compound according to this embodiment may be used as a host or a guest of the light-emitting layer. It may also be used as an assist material that can be contained in the light-emitting layer. The organic compound according to this embodiment can be suitably used as a host for the light-emitting layer in systems that use triplet excited states, such as phosphorescence and delayed fluorescence, for light emission. Therefore, it is preferable that the light-emitting layer further contains a phosphorescent compound. Furthermore, the organic compound according to this embodiment can be used in combination with an electron-transporting host. Therefore, it is preferable that the light-emitting layer further contains an electron-transporting compound. Here, the host is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. Furthermore, the guest is a compound with a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer, and is responsible for the main light emission. Furthermore, the assist material is a compound with 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.

[0105] The concentration of the host in 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 concentration of the guest 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 concentration of the guest is particularly preferably 10% by mass or less.

[0106] The guest may be contained uniformly throughout the layer in which the host serves as a matrix, or may be contained with a concentration gradient. Alternatively, the guest may 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.

[0107] The light-emitting layer of this embodiment may be a single layer or multiple layers, and color mixing is possible by including a light-emitting material having a different emission color. Multiple layers refer to a state in which the light-emitting layer and another light-emitting layer are stacked. In this case, the emission color of the organic light-emitting element is not particularly limited. More specifically, it may be white or a neutral color. In the case of white, for example, if the light-emitting layer emits blue, the other light-emitting layer emits a color different from blue, i.e., green or red. Furthermore, the film formation method may be vapor deposition or coating film formation. Furthermore, a third light-emitting layer emitting blue light and a charge generation layer may be provided between the light-emitting layer or stacked light-emitting layer of this embodiment and the first or second electrode. The charge generation layer functions as a tandem element, where electrons generated from the charge generation layer and holes injected from the first electrode recombine to generate excitons, and holes generated from the charge generation layer and electrons injected from the second electrode recombine to form excitons. This doubles the internal quantum efficiency. 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 the complementary color of the blue light-emitting element. Therefore, by using a stacked light-emitting layer made of the light-emitting layer of this embodiment and a blue light-emitting layer to form a tandem element, a white light-emitting element can be provided. 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.

[0108] Specific device configurations of the organic light-emitting element of this embodiment include multilayer device configurations in which electrode layers and organic compound layers shown in (1) to (6) below are sequentially stacked on a substrate. In any device configuration, the organic compound layer always 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

[0109] However, these examples of device configurations 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, configuring the electron transport layer or hole transport layer from two layers with different ionization potentials, or configuring the light-emitting layer from two layers made of different light-emitting materials.

[0110] Among the device configurations shown in (1) to (6) above, configuration (6) is preferred because it has both an electron blocking layer and a hole blocking layer. That is, in 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 made of carbon-carbon bonds. In other words, it is preferably made 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 element. This allows the electron blocking layer and the hole blocking layer to play important roles. 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 Preferably, it is an organic compound consisting of carbon-carbon bonds.

[0111] The mode of extraction of light output from the light-emitting layer (device configuration) 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.A double-sided emission type in which light is extracted from both the substrate side and the opposite side of the substrate may also be employed.

[0112] The organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer that constitutes the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not particularly limited. More specifically, it may be white or a neutral color.

[0113] <Other Compounds> The organic light-emitting device according to this embodiment may contain, if necessary, conventionally known low-molecular-weight or high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. Examples of these compounds are listed below.

[0114] As the hole injection and transport material, a material with high hole mobility is preferred so that holes can be easily injected from the anode and the injected holes can be transported to the light-emitting layer. Furthermore, a material with a high glass transition temperature is preferred to suppress deterioration of film quality, such as crystallization, in the organic light-emitting device. Examples of low-molecular-weight and high-molecular-weight materials with hole injection and transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above-mentioned hole injection and transport materials are also suitable for use in electron blocking layers. Specific examples of compounds that can be used as hole injection and transport materials are listed below, but of course, the present invention is not limited to these.

[0115]

[0116] Examples of light-emitting materials that are primarily involved in light-emitting function include fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Specific examples of compounds that can be used as light-emitting materials are shown below, but the present invention is not limited to these.

[0117]

[0118]

[0119] 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, organoaluminum complexes such as tris(8-quinolinolato)aluminum, and organic beryllium complexes.

[0120]

[0121] The electron transport material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected taking into consideration the balance with the hole mobility of the hole transport material. Examples of materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the electron transport material is also preferably used in the hole blocking layer. Specific examples of compounds used as electron transport materials are shown below, but of course, are not limited to these.

[0122]

[0123] The electron injection material can be arbitrarily selected from those that allow easy electron injection from the cathode, and is selected taking into consideration the balance with hole injection properties, etc. Organic compounds include n-type dopants and reducing dopants. Examples include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives. They can also be used in combination with the above-mentioned electron transport materials.

[0124] <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.

[0125] [Substrate] Examples of the substrate include quartz, glass, silicon wafer, resin, and metal. Furthermore, the substrate may be provided with a switching element such as a transistor and wiring, and an insulating layer thereon. The insulating layer may be made of any material as long as it can form a contact hole so that wiring can be formed between the first electrode and the insulating layer, and can ensure insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0126] [Electrodes] 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.

[0127] The anode material should have as large a work function as possible. Examples of such materials include simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, mixtures containing these metals, alloys of these metals, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and zinc indium oxide. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0128] These electrode materials may be used alone or in combination of two or more. The anode may be composed of one layer or multiple layers.

[0129] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. The above materials can also function as a reflective film without functioning as an electrode. When used as a transparent electrode, transparent conductive oxide layers such as indium tin oxide (ITO) and indium zinc oxide can be used, but are not limited to these. Photolithography technology can be used to form the electrode.

[0130] On the other hand, materials with a low work function are preferred for the cathode. Examples include alkali metals such as lithium, alkaline earth metals such as calcium, and metals such as aluminum, titanium, manganese, silver, lead, and chromium, as well as mixtures containing these metals. Alternatively, alloys combining these metals can be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, and zinc-silver can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials can be used alone or in combination. The cathode can have either a single-layer or multi-layer structure. Among these, silver is preferred, and a silver alloy is even more preferred to reduce silver aggregation. The alloy ratio is not critical as long as silver aggregation can be reduced. For example, the silver:other metal ratio can be 1:1, 3:1, or the like.

[0131] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but DC and AC sputtering methods are more preferable because they provide good film coverage and make it easier to reduce resistance.

[0132] [Organic Compound Layer] The organic compound layer may be formed as a single layer or as multiple layers. When multiple layers are present, they may be called hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, or electron injection layer depending on their functions. The organic compound layer is mainly composed of organic compounds but may also contain inorganic atoms or inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. 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.

[0133] 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.

[0134] The organic compound layer constituting the organic light-emitting device according to one embodiment of the present invention can be formed by a dry process such as vacuum deposition, ionization deposition, sputtering, or plasma. Instead of a dry process, a wet process can also be used in which a 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, or LB method). Among these, vacuum deposition, ionization deposition, inkjet printing, and nozzle coating are suitable for producing a large-area organic light-emitting device.

[0135] Here, when a 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 a film is formed by a coating method, the film can be formed by combining with an appropriate binder resin.

[0136] 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.

[0137] These binder resins may be used singly or in combination as homopolymers or copolymers, and may further contain known additives such as plasticizers, antioxidants, and ultraviolet absorbers, if necessary.

[0138] The thickness of each layer in the organic light-emitting device is preferably 1 nm to 10 μm in general, and in particular, the thickness of the light-emitting layer of the organic compound layer is preferably 10 nm to 100 nm in order to obtain effective light-emitting characteristics.

[0139] [Protective Layer] A protective layer may be provided on the second electrode. For example, by adhering glass with a moisture absorbent to the second electrode, the intrusion of water and other contaminants into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the second electrode to reduce the intrusion of water and other contaminants into the organic compound layer. For example, after forming the second electrode, the second electrode may be transferred to another chamber without breaking the vacuum, and a 2 μm-thick silicon nitride film may be formed by CVD to serve as a protective layer. A protective layer may be provided using atomic layer deposition (ALD) after the CVD film formation. The material of the film formed by ALD is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed on the film formed by ALD by CVD. The film formed by ALD may have a thickness smaller than that of the film formed by CVD. Specifically, the thickness may be 50% or less, or even 10% or less.

[0140] [Color Filter] A color filter may be provided on the protective layer. For example, a color filter taking into consideration the size of the organic light-emitting element may be provided on a separate substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using photolithography technology. The color filter may be made of a polymer.

[0141] [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 the unevenness of the underlying layer. It may also be called a material resin layer without limiting its purpose. The planarization layer may be composed of an organic compound, and may be either a low molecular weight or a high molecular weight, but is preferably a high molecular weight.

[0142] The planarizing layer may be provided above or below the color filter, and may be made of the same or different materials, such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0143] [Microlens] The organic light-emitting element may have an optical component such as a microlens on its light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be used to increase the amount of light extracted from the organic light-emitting element and to control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be determined in the same way in any cross-sectional view. In other words, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the semicircle is the vertex of the microlens.

[0144] It is also possible to define the midpoint of a microlens. In the cross section of the microlens, a line segment is imagined from the point where an arc shape ends to the point where another arc shape ends, and the midpoint of this line segment can be called the midpoint of the microlens. The cross section for determining the vertex and midpoint may be a cross section perpendicular to the insulating layer.

[0145] [Counter Substrate] An 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 defined as a first substrate, the counter substrate may be a second substrate.

[0146] [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 voltage-programmed or current-programmed. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission brightness of the light-emitting element, a transistor that controls the emission timing, a capacitor that holds the gate voltage of the transistor that controls the emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0147] 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 characteristics of the transistor constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistor constituting the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics. The transistor constituting the pixel circuit is a transistor connected to a light-emitting element, such as a first light-emitting element.

[0148] [Pixel] An organic light-emitting device having an organic light-emitting element may have a plurality of pixels. Each pixel has sub-pixels that emit different colors. The sub-pixels may each emit RGB light, for example.

[0149] The pixel emits light from 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 subpixels may be 10 μm or less, or more specifically, it may be 8 μm, 7.4 μm, or 6.4 μm.

[0150] The pixels may be arranged in a known manner in a plan view. For example, they may be in a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in a plan view may be any known shape. For example, they may be rectangular, quadrilaterals such as diamonds, or hexagons. Of course, a shape that is close to a rectangle, rather than an exact shape, is included in the rectangle. The shape of the subpixels and the pixel arrangement may be used in combination.

[0151] The organic light-emitting device according to this embodiment can be used as a component of a display device or a lighting device. Other applications include an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, and a light-emitting device having a white light source and a color filter.

[0152] The display device may be an image information processing device having an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., an information processing unit that processes the input information, and displays the input image on a display unit. The display device has a plurality of pixels, and at least one of the plurality of pixels 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.

[0153] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of this touch panel function may be an infrared method, a capacitance method, a resistive film method, or an electromagnetic induction method, and is not particularly limited. The display device may also be used in the display unit of a multifunction printer.

[0154] Next, a display device according to this embodiment will be described with reference to the drawings. Figures 1A and 1B are cross-sectional schematic diagrams 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).

[0155] 1A is a cross-sectional schematic diagram of an example of a pixel, which is a component of a display device according to this embodiment. The pixel includes subpixels 10. The subpixels are divided into 10R, 10G, and 10B based on their light emission. The emitted colors may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the subpixels may be selectively transmitted or color-converted using a color filter or the like. Each subpixel 10 includes a reflective electrode serving as a first electrode 2 on an interlayer insulating layer 1, an insulating layer 3 covering the edge of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode serving as a second electrode 5, a protective layer 6, and a color filter 7.

[0156] A transistor and a capacitor element 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).

[0157] The insulating layer 3 is also called a bank or a pixel separation film. It covers the edges of the first electrode 2 and is disposed to surround the first electrode 2. The portion where the insulating layer 3 is not disposed is in contact with the organic compound layer 4 and becomes a light-emitting region.

[0158] 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 .

[0159] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0160] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 is illustrated as being one layer, it may be a multi-layer structure, with each layer being an inorganic compound layer and an organic compound layer.

[0161] The color filters 7 are divided into 7R, 7G, and 7B depending on their colors. The color filters 7 may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters 7. The color filters 7 may be formed on a protective layer 6. Alternatively, the color filters 7 may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0162] The display device 100 in FIG. 1B 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 is provided with an insulating layer 12 on top of it. An active element such as the TFT 18 is disposed on the insulating layer 12, and a gate electrode 13 of the active element, a gate insulating film 14, and a semiconductor layer 15 are provided. The TFT 18 has a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on top of the TFT 18. An anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film 19.

[0163] Note that the method of electrical connection between the electrodes (anode 21 and cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17 and drain electrode 16) included in the TFT 18 is not limited to the mode shown in FIG. 1B. That is, any one of the anode 21 or the cathode 23 may be electrically connected to any one of the source electrode 17 or the drain electrode 16 of the TFT 18.

[0164] In the display device 100 of FIG. 1B, the organic compound layer 22 is illustrated as if it were a single layer, but the organic compound layer 22 may be a plurality of layers. On the cathode 23, a first protective layer 24 and a second protective layer 25 for reducing the deterioration of the organic light-emitting element 26 are provided.

[0165] In the display device 100 of FIG. 1B, a transistor is used as the switching element, but other switching elements such as a MIM element may be used instead.

[0166] Further, the transistor used in the display device 100 of FIG. 1B is not limited to a thin-film transistor having an active layer on an insulating surface of a substrate, and a transistor using a single-crystalline silicon wafer may also be used. Examples of the active layer include non-single-crystalline silicon such as single-crystalline silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystalline oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Note that the thin-film transistor is also called a TFT element.

[0167] The transistor included in the display device 100 of FIG. 1B may be formed in a substrate such as a Si substrate. Here, forming in the substrate means manufacturing a transistor by processing the substrate itself such as a Si substrate. That is, having a transistor in the substrate can also be regarded as the substrate and the transistor being integrally formed.

[0168] The organic light-emitting element according to this embodiment has its emission brightness controlled by a TFT, which is an example of a switching element. By providing multiple organic light-emitting elements on a surface, an image can be displayed based on the emission brightness of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor formed from low-temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also be referred to as "inside the substrate." Whether to provide a transistor within the substrate or to use a TFT is determined by the size of the display unit. For example, for a display unit of about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0169] 2 is a schematic diagram illustrating an example of a display device according to this embodiment. The display device 1000 may include a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The touch panel 1003 and the display panel 1005 are connected by flexible printed circuits FPCs 1002 and 1004. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position even if the display device is a portable device.

[0170] The display device according to this embodiment may have color filters having red, green, and blue colors, which may be arranged in a delta arrangement.

[0171] The display device according to the present embodiment may be used as a display unit of a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include a mobile phone such as a smartphone, a tablet, and a head-mounted display.

[0172] The display device according to this embodiment may be used as a display unit of an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0173] 3A is a schematic diagram illustrating an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may include a display device according to this embodiment. In this case, the display device may display not only an image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject is moving, the possibility that the subject will be blocked by an obstruction, and the like.

[0174] Since the optimum timing for capturing an image is very short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment. This is because the organic light-emitting element has a fast response speed. Display devices using organic light-emitting elements require high display speed, and these devices can be used more preferably than liquid crystal display devices.

[0175] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses, which form an image on an imaging element housed in a housing 1104. The focus of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may also be called a photoelectric conversion device. Instead of sequentially capturing images, the photoelectric conversion device may include an imaging method that detects the difference from the previous image, or a method of cutting out an image that is constantly being recorded.

[0176] FIG. 3B is a schematic diagram illustrating an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit 1202 may be a biometric recognition unit that recognizes a fingerprint to perform operations such as unlocking. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an image sensor. An image captured by the camera function is displayed on the display unit 1201. Examples of the electronic device 1200 include a smartphone and a laptop computer.

[0177] 4A and 4B are schematic diagrams illustrating an example of a display device according to this embodiment. FIG. 4A illustrates a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The display unit 1302 may use a light-emitting element according to this embodiment. The display device 1300 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. 4A . 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.

[0178] FIG. 4B is a schematic diagram illustrating another example of a display device according to the present embodiment. The display device 1310 in FIG. 4B is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include a light-emitting element according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be a single, seamless display device. The first display unit 1311 and the second display unit 1312 can be separated by the bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may display a single image.

[0179] 5A is a schematic diagram illustrating an example of an illumination device according to this embodiment. The illumination device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusion unit 1405. The light source 1402 may include an organic light-emitting element according to this embodiment. The optical filter 1404 may be a filter that improves the color rendering of the light source. The light diffusion unit 1405 can effectively diffuse light from the light source, such as for illumination, and deliver the light over a wide area. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the illumination device. If necessary, a cover may be provided on the outermost surface.

[0180] The lighting device is, for example, a device for illuminating a room. The lighting device may emit white, daylight white, or any other color from blue to red. It may have a dimming circuit for dimming them or a color tuning circuit for tuning 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 for converting AC voltage to DC voltage. The lighting device may have an inverter circuit. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device may have a color filter.

[0181] The lighting device according to this embodiment may also include a heat dissipation unit, which dissipates heat from within the device to the outside, and may be made of a material such as a metal with a high specific heat capacity or liquid silicon.

[0182] 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 lighting device. The automobile 1500 has tail lamps 1501, and may be configured to turn on the tail lamps when braking or the like is performed.

[0183] The tail lamp 1501 may include the organic light-emitting element according to this embodiment. The tail lamp 1501 may include a protective member for protecting the organic light-emitting element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0184] The automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display as long as it is not a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, constituent materials of the electrodes and the like of the organic light-emitting element are made of transparent materials.

[0185] The moving body according to this embodiment may be a ship, an aircraft, a drone, or the like. The moving body may have a body and a lighting device provided on the body. The lighting device may emit light to indicate the position of the body. The lighting device has the organic light-emitting element according to this embodiment.

[0186] 6A and 6B , application examples of the display devices according to the above-described embodiments will be described. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, HMDs, and smart contact lenses. The image capturing and display device used in such application examples includes an image capturing device capable of photoelectrically converting visible light and a display device capable of emitting visible light.

[0187] Fig. 6A is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using Fig. 6A, eyeglasses 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 lenses 1601 of the eyeglasses 1600. Furthermore, a display device according to any of the above-described embodiments is provided on the back side of the lenses 1601.

[0188] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the image capture device 1602 and the display device. The control device 1603 also controls the operations of the image capture device 1602 and the display device. The lens 1601 is formed with an optical system for focusing light onto the image capture device 1602.

[0189] FIG. 6B is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 6B , glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 have a control device 1612, which is equipped with an imaging device corresponding to the imaging device 1602 in FIG. 6A and a display device. A lens 1611 is formed with an optical system for projecting light emitted from the imaging device in the control device 1612 and the display device, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and also controls the operation of the imaging device and the display device.

[0190] The control device 1612 may include a gaze detection unit that detects the wearer's gaze. The gaze detection may use infrared light. The infrared light emitter emits infrared light toward the eyeball of the user gazing at the display image. An imaging unit with a light-receiving element detects the reflected infrared light from the eyeball, thereby obtaining a captured image of the eyeball. By including a reduction unit that reduces light from the infrared light emitter to the display unit in a planar view, degradation of image quality is reduced. The user's gaze toward the displayed image is detected from the captured image of the eyeball obtained by capturing infrared light. Any known method can be applied to gaze detection using the captured image of the eyeball. As an example, a gaze detection method based on a Purkinje image formed by reflection of irradiated light on the cornea can be used. More specifically, gaze detection processing based on the pupil-corneal reflex method is performed. Using the pupil-corneal reflex method, a gaze vector representing the orientation (rotation angle) of the eyeball is calculated based on the image of the pupil and the Purkinje image included in the captured image of the eyeball, thereby detecting the user's gaze.

[0191] A display device according to one embodiment of the present invention may include an imaging device having a light receiving element, and may control the display image of the display device based on user line-of-sight information from the imaging device. Specifically, the display device determines a first field of view area where the user gazes and a second field of view area other than the first field of view area based on the line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. In the display area of ​​the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than that of the first field of view area.

[0192] The display area includes a first display area and a second display area different from the first display area, and a high-priority area is determined from the first display area and the second display area based on line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. The resolution of the high-priority area may be controlled to be higher than the resolution of areas other than the high-priority area. In other words, the resolution of an area with a relatively low priority may be lowered.

[0193] Note that 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 gaze and the distance to an object in the line of sight from the image of the eyeball, using as training data an image of the eyeball and the direction in which the eyeball in the image was actually looking. The AI ​​program may be included in the display device, the imaging device, or an external device. If included in the external device, it is transmitted to the display device via communication.

[0194] When display control is performed based on visual recognition detection, the smart glasses can be preferably applied to smart glasses that further include an imaging device for capturing images of the outside world. The smart glasses can display captured external information in real time.

[0195] 7A is a schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 includes the organic light-emitting element according to this embodiment. The developing unit 31 includes toner and the like. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0196] 7B and 7C are diagrams showing an exposure light source 28 and are schematic diagrams illustrating a state in which multiple light-emitting units 36 are arranged on a long substrate. 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 referred to as the long axis direction of the photoconductor 27. FIG. 7B shows a configuration in which the light-emitting units 36 are arranged along the long axis of the photoconductor 27. FIG. 7C shows a configuration different from that shown in FIG. 7B, in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are arranged at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged at intervals. In the second column, the light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. In other words, multiple light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in FIG. 7C can also be described as a grid-like arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0197] As described above, by using the device using the organic light-emitting element according to this embodiment, it is possible to achieve a display with good image quality and stability even over a long period of time. Furthermore, by using the device using the organic light-emitting element according to this embodiment, it is possible to achieve both good visibility outdoors due to highly efficient and bright light output and power-saving display.

[0198] The present invention will be described below with reference to examples, although the present invention is not limited to these examples.

[0199] Example 1 (Synthesis of Exemplary Compound B27)

[0200]

[0201] The following reagents and solvents were placed in a 500 ml recovery flask: Compound G1: 1.00 g (3.63 mmol), Compound G2: 1.40 g (3.63 mmol), Pd(OAc). ２ : 25mg (0.11mmol) s-phos: 163mg (0.36mmol) K ３ P.O. ４ : 1.54 g (7.26 mmol) Toluene: 30 ml Water: 1 ml

[0202] 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 the mixture was filtered to obtain a crude product. This crude product was purified by silica gel column chromatography (chlorobenzene) and recrystallized from xylene to obtain 907 mg (yield: 65%) of Exemplary Compound B27.

[0203] Exemplary Compound B27 was subjected to mass spectrometry using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[0204] [MALDI-TOF-MS] Measured value: m / z = 500 Calculated value: C ３６ H ２１ NS=500

[0205] 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 for 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.

[0206]

[0207]

[0208]

[0209]

[0210] Example 29 An organic light-emitting device having a bottom-emission structure was fabricated in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed on a substrate.

[0211] First, an ITO film was formed on a glass substrate and then patterned as desired to form an ITO electrode (anode). At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed was used as the ITO substrate in the following steps. 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 100 Pa. At this time, the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was 3 mm ２ It was made to be like this.

[0212]

[0213] 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 carried out 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.

[0214] In this example, the measuring device was specifically a microcurrent meter 4140B manufactured by Hewlett-Packard Company to measure the current-voltage characteristics, and a BM7 manufactured by Topcon Corporation to measure the luminance.

[0215] [Examples 30 to 52, Comparative Example 1] Organic light-emitting devices were fabricated 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 devices were measured and evaluated in the same manner as in Example 29. The measurement results are shown in Table 10.

[0216]

[0217] As described above, when the exemplary compound according to this embodiment is used, since it has an indolocarbazole unit and heteroaryl units at two ends of the molecule, 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.

[0218] The present invention is not limited to the above-described embodiments, and various modifications and variations can be made without departing from the spirit and scope of the present invention. Therefore, the following claims are appended to apprise the public of the scope of the present invention.

[0219] This application claims priority based on Japanese Patent Application No. 2023-185492, filed on October 30, 2023, the entire contents of which are incorporated herein by reference.

[0220] REFERENCE SIGNS LIST 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]: 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]: In the general formula [a], X １ , X ２ are each independently selected from O, S, Se, and Te. 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. 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 H. 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. 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]: 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 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 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]; 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], 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. The organic compound according to claim 1 or 2, characterized in that 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. The organic compound according to claim 1 or 2, characterized in that in the general formula [1], n is 0.

7. In the general formula [1], the HAr 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], the HAr 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], 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. 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 of the organic compound layers contains the organic compound described in claim 1 or 2.

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

13. The organic light-emitting element 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 laminated state with the light-emitting layer, the other 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 having 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. A photoelectric conversion device comprising an optical section having a plurality of lenses, an image sensor that receives light that has passed through the optical section, and a display section that displays an image captured by the image sensor, wherein the display section has the organic light-emitting element according to claim 10.

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

19. 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 the light emitted by the light source.

20. A moving object comprising a lighting fixture having the organic light-emitting element according to claim 10, and a body on which the lighting fixture is mounted.

21. An image forming apparatus comprising: a photoconductor; and an exposure light source for exposing said photoconductor, said exposure light source comprising the organic light-emitting element according to claim 10.

Images