JP7622028B2 - Organic compound and organic light-emitting device - Google Patents

Description

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

An organic light-emitting element (hereinafter sometimes referred to as an "organic electroluminescence element" or "organic EL element") is an electronic element having a pair of electrodes and an organic compound layer disposed between the electrodes. By injecting electrons and holes from the pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting element emits light.

Recent progress in organic light-emitting devices has been remarkable, with features including low driving voltage, diverse emission wavelengths, fast response, and the ability to make light-emitting devices thinner and lighter.

In addition, sRGB and AdobeRGB standards are used to represent the color reproduction range of displays, and materials that can reproduce these have been in demand, but recently BT-2020 has been proposed as a standard that will further expand the color reproduction range.

Incidentally, there has been active research into the creation of luminescent organic compounds to date. This is because the creation of compounds with excellent luminescent properties is important in providing high-performance organic light-emitting devices.

As a compound that has been created so far, Patent Document 1 describes the following compound 1-a.

US Patent Application Publication No. 2017/0256717 Chinese Patent Publication No. 107043382

Patent Document 1 describes compound 1-a as a light-emitting material, but compound 1-a has issues with color purity.

The present invention has been made in consideration of the above problems, and aims to provide an organic compound with excellent color purity.

The organic compound according to the present invention is characterized by being represented by general formula (1).

In general formula (1), _R1 to _R20 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a cyano group.

R ₁ to R ₂₀ may be bonded to each other to form a ring. The bond may be via a chalcogen atom. At least one of the combinations of R ₉ and R ₁₀ and R ₁₉ and R ₂₀ is bonded to each other to form a 5-membered or 6-membered ring .

_X1 and _X2 are each independently selected from the group consisting of a chalcogen atom and a substituted or unsubstituted silylene group.

The organic compound according to the present invention has a fused ring structure, which allows it to emit blue light with excellent color purity.

1A is a schematic cross-sectional view showing an example of a pixel of a display device according to an embodiment of the present invention, and FIG. 1B is a schematic cross-sectional view showing an example of a display device using an organic light-emitting element according to an embodiment of the present invention. FIG. 1 is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention. 1A is a schematic diagram illustrating an example of an imaging device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of an electronic device according to an embodiment of the present invention. 1A is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of a foldable display device. 1A is a schematic diagram showing an example of an illumination device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing an example of an automobile having a vehicle lamp according to an embodiment of the present invention. 1A is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, the wearable device having an imaging device. 1A is a schematic diagram showing an example of an image forming apparatus according to an embodiment of the present invention, FIG. 1B is a schematic diagram showing an example of an exposure light source of the image forming apparatus according to an embodiment of the present invention, and FIG. 1C is a schematic diagram showing an example of an exposure light source of the image forming apparatus according to an embodiment of the present invention.

In this specification, examples of halogen atoms include, but are not limited to, fluorine, chlorine, bromine, iodine, astatine, and tennessine.

Examples of chalcogen atoms include, but are not limited to, oxygen, sulfur, selenium, tellurium, polonium, and livermorium.

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

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

The aryl group may be an aryl group having 6 to 20 carbon atoms. Examples include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, an anthranyl group, a perylenyl group, a chrysenyl group, and a fluoranthenyl group.

The heteroaryl group may be a heteroaryl group having 3 to 20 carbon atoms. Examples include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, and a phenanthrolyl group.

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

Examples of amino groups include N-methylamino, N-ethylamino, N,N-dimethylamino, N,N-diethylamino, N-methyl-N-ethylamino, N-benzylamino, N-methyl-N-benzylamino, N,N-dibenzylamino, anilino, N,N-diphenylamino, N,N-dinaphthylamino, N,N-difluorenylamino, N-phenyl-N-tolylamino, and N,N-ditolylamino. , N-methyl-N-phenylamino group, N,N-dianisolylamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tertiarybutylphenyl)amino group, N-phenyl-N-(4-trifluoromethylphenyl)amino group, N-piperidyl group, carbazolyl group, acridyl group, trimethylamino group, triphenylamino group, etc., but are not limited to these.

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

(1) Organic Compound First, the organic compound according to the present invention will be described.

The organic compound according to the present invention is a compound represented by general formula (1). In this specification, the main skeleton refers to a skeleton having a structure in which three benzene rings and two six-membered rings containing a chalcogen atom are condensed. In addition, the basic skeleton refers to a skeleton having a structure in which at least one of the substituents that respectively substitute for the two nitrogen atoms in the main skeleton is condensed to the main skeleton.

In general formula (1), _R1 to _R20 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a cyano group.

R ₁ to R ₂₀ may be bonded to each other to form a ring. The bond may be via a chalcogen atom. The chalcogen atom via the bond is preferably an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom, and more preferably an oxygen atom or a sulfur atom. At least one of the combinations of R ₉ and R ₁₀ and R ₁₉ and R ₂₀ is bonded to each other.

_X1 and _X2 are each independently selected from the group consisting of a chalcogen atom, a substituted or unsubstituted imino group, a substituted or unsubstituted methylene group, and a substituted or unsubstituted silylene group. In _X1 and _X2 , the chalcogen atom is preferably an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom, and more preferably an oxygen atom or a sulfur atom.

In addition, among the organic compounds according to the present invention, those having a structure represented by general formula (2) or (3) are preferred.

In general formulas (2) and (3), _R21 to _R36 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a cyano group.

_R21 to _R36 may be bonded to each other to form a ring. The bond may be via a chalcogen atom. The chalcogen atom via the bond is preferably an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom, more preferably an oxygen atom or a sulfur atom, and particularly preferably an oxygen atom.

_X1 to _X4 are each independently selected from the group consisting of a chalcogen atom, a substituted or unsubstituted imino group, a substituted or unsubstituted methylene group, and a substituted or unsubstituted silylene group. _X1 to _X4 are preferably an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom, more preferably an oxygen atom or a sulfur atom, and particularly preferably an oxygen atom.

It is particularly preferable that the organic compound according to the present invention has a structure represented by general formula (3).

In addition, in one embodiment of the present invention, the structure shown in general formula (4) may not be present.

In the general formula (4), _X5 and _X6 are selected from an oxygen atom, a sulfur atom, a dimethylmethylene group, a sulfonyl group, and the general formula (5). * represents the bonding position to _R26 and _R34 , and *' represents the bonding position to _R27 and _R35 .

In formula (5), R ₄₁ is a phenyl group. * indicates the bonding position.

The organic compounds represented by the general formulas (1) to (3) have the following characteristics.
(1-1) The basic skeleton has a structure in which at least one of the substituents substituted on each of the two nitrogen atoms in the main skeleton is fused to the main skeleton, thereby emitting blue light with excellent color purity.
(1-2) The basic skeleton is composed of multiple condensed ring structures, and therefore has high thermal stability.

The following describes the properties of the basic skeleton of the organic compound according to the present invention, while comparing and contrasting comparative compounds that have a structure similar to that of the organic compound according to the present invention. Specifically, the comparative compound 1-a and the exemplary compound of this embodiment are given.

(1-1) The basic skeleton has a structure in which at least one of the substituents substituted on each of the two nitrogen atoms in the main skeleton is fused to the main skeleton, emitting blue light with excellent color purity.

When inventing the organic compound represented by general formula (1), the inventors focused on the basic skeleton itself.

First, in order to emit blue light with good color purity, the basic skeleton itself must be in the blue region with high color purity. In this embodiment, blue light emission with the desired excellent color purity means that the maximum emission wavelength of the emission spectrum in a dilute toluene solution is 440 to 475 nm, and the half-width is 50 nm or less. Furthermore, in order to obtain blue light emission with even better color purity, it is preferable that the half-width is 40 nm or less. In this specification, the half-width of the emission spectrum refers to the spectral width of 0.5 intensity when the maximum intensity is 1.0.

The exemplary compound according to the present invention has a structure in which at least one of the substituents substituted on each of the two nitrogen atoms in the main skeleton is fused to the main skeleton. As a result, it has been found that the half-width of the emission spectrum is narrowed because molecular vibration and structural changes between the excited state and the ground state are suppressed compared to a structure in which the substituents are not fused to the main skeleton.

On the other hand, comparative compound 1-a has two C-N bonds with rotation axes, and none of the substituents that are substituted for the two nitrogen atoms in the main skeleton are condensed to the main skeleton. Therefore, the half-width of the emission spectrum becomes wider due to the influence of vibrations caused by the C-N bonds and structural changes between the excited state and the ground state.

In Table 1, the emission spectra in a dilute toluene solution were compared using the exemplary compounds according to the present invention and the comparative compounds. Specifically, after measuring the emission spectra, the half-widths of the obtained emission spectra and the emission colors were compared. The emission wavelengths were measured by photoluminescence measurement of a dilute toluene solution at room temperature and an excitation wavelength of 350 nm using a Hitachi F-4500. Note that with regard to the half-widths of the emission spectra in Table 1, "A" indicates that they are 40 nm or less, "B" indicates that they are 50 nm or less, and "C" indicates that they are greater than 50 nm. AA indicates that the color purity is even better than A.

As can be seen from Table 1, in contrast to the comparative compound 1-a, the compound according to the present invention has a structure in which at least one of the substituents substituting each of the two nitrogen atoms in the main chain is fused to the main chain. Therefore, it can be seen that the compound has a half-width of 50 nm or less, which is necessary for blue emission with excellent color purity. In this way, as a unique effect of having a structure in which at least one of the substituents substituting each of the two nitrogen atoms in the main chain is fused to the main chain, blue emission with excellent color purity is emitted. In particular, it is preferable that both of the substituents substituting each of the two nitrogen atoms in the main chain are fused to the main chain.

(1-2) The basic skeleton is made up of multiple fused ring structures, so it has high thermal stability.

The organic layer of an organic light-emitting element, particularly the compounds in the light-emitting layer, repeatedly transition between the ground state and the excited state during the light-emitting process of the organic light-emitting element, particularly in the light-emitting layer. During this process, molecular movements such as stretching, contraction, and rotation occur. If there is a site where the bond is easily dissociated, the bond may be cleaved and part of the compound may become free. When part of the compound becomes free, the structure changes, and compounds that are prone to freeing have low durability. Furthermore, when such a compound is used in an organic light-emitting element, the free part becomes a quencher, reducing the durability of the element. Therefore, the more molecules have a structure that makes it difficult for bonds to dissociate and freeing to occur, the better the durability of the element.

Table 2 shows the structural differences between the exemplary compound A2 according to the present invention and the comparative compound 1-a. The exemplary compound A2 according to the present invention has a basic skeleton, and therefore has a C-C bond with high bond energy in addition to a C-N bond with low bond energy. On the other hand, the comparative compound 1-a only has a C-N bond with low bond energy. Therefore, the organic compound according to the present invention has higher bond stability than the comparative compound 1-a, and therefore the element durability characteristics are improved.

Furthermore, the organic compound according to the present invention preferably has the following characteristics.
(1-3) In general formulas (2) and (3), durability is improved when at least one of R ₂₁ , R ₂₂ , R ₂₃ , R ₂₆ , R ₂₇ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₄ , and R ₃₅ is other than a hydrogen atom, i.e., a substituent.
(1-4) In the general formulae (2) and (3), when at least one of R ₂₁ and R ₂₉ is a substituent, concentration quenching can be suppressed.

These features are explained below.

(1-3) In general formulas (2) and (3), durability is improved when at least one of R ₂₁ , R ₂₂ , R ₂₃ , R ₂₆ , R ₂₇ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₄ , and R ₃₅ is other than a hydrogen atom, i.e., a substituent.

Table 3 shows the calculation results of the basic skeleton torsion angle and S1 (lowest excited singlet energy) when a phenyl group is introduced into each substitution position in the general formula (3). The basic skeleton torsion angle is an index representing the planarity of the basic skeleton, and it can be said that the smaller the basic skeleton torsion angle, the higher the planarity. According to Table 3, it is preferable that at least one of the substitution positions R ₂₁ , R ₂₂ , R ₂₃ , R ₂₆ , or R ₂₇ is a substituent, since the basic skeleton torsion angle shows a small value, it is more preferable that at least one of R ₂₂ , R ₂₃ , R ₂₆ , or R ₂₇ is a substituent, and it is particularly preferable that at least one of R _{22 , R 23 , or R 27 is a substituent. In particular, it is preferable that at least one of the substitution positions R 22 , R 23 ,} or R ₂₇ is a substituent, so that S1 shows a large value. By showing a small value of the basic skeleton twist angle, the half width of the emission spectrum becomes narrow, and excellent durability is shown. In addition, by showing a large value of S1, blue light emission with high color purity is shown. Therefore, in the general formulas (2) and (3), it is preferable that at least one of R ₂₁ , R ₂₂ , R ₂₃ , R ₂₆ , R ₂₇ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₄ , or R ₃₅ is a substituent, it is more preferable that at least one of _{R 22} , R ₂₃ , R _{27 , R 30 , R 31 , or R 35 is a substituent, it is more preferable that at least one of R 27 or R 35 has a substituent , and it is} particularly preferable that R ₂₇ and R ₃₅ are substituents. As the substituent, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms is preferable, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms is more preferable, and a tert-butyl group, an isopropyl group, or a phenyl group is particularly preferable.

The above S1 energy and basic skeleton torsion angle were calculated using molecular orbital calculations. The currently widely used density functional theory (DFT) was used as the molecular orbital calculation method. The functional used was B3LYP, and the basis set was 6-31G ^* . The molecular orbital calculation method used was the currently widely used Gaussian 09 (Gaussian 09, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hračky, et al., J ... hian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr. , J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. B Rothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gompert s, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc. , Wallingford CT, 2010. ). Hereinafter, the same method will be used for molecular orbital calculations in this specification.

(1-4) In the general formulae (2) and (3), when at least one of R ₂₁ and R ₂₉ is a substituent, concentration quenching can be suppressed.

Since the basic skeleton has high planarity, in the thin film state, intermolecular stacking tends to cause concentration quenching of luminescence. In the general formulas (2) and (3), when at least one of R ₂₁ or R ₂₉ is a substituent, the basic skeleton and the substituent are twisted due to steric hindrance. Therefore, in the thin film state, intermolecular stacking is suppressed, and concentration quenching of luminescence can be suppressed. Therefore, at least one of R ₂₁ or R ₂₉ is preferably a substituent, and more preferably R ₂₁ and R ₂₉ are substituents. As the substituent, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a fluorine group are preferable, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 12 carbon atoms are more preferable, and a tert-butyl group, an isopropyl group, and an ortho-substituted phenyl group are particularly preferable.

In addition, the organic compound represented by general formula (2) further has the following characteristics:

(1-5) The organic compound represented by general formula (2) has a basic skeleton composed of a six-membered ring, and therefore exhibits a high T1 (lowest excited triplet energy).

Among the organic compounds according to the present invention, the organic compound represented by the general formula (2) has a conjugation length that is difficult to extend compared to the organic compound represented by the general formula (3) because _X3 and _X4 are not direct bonds. Therefore, the organic compound represented by the general formula (2) exhibits a particularly high T1 among the organic compounds according to the present invention. Due to the above characteristics, the organic compound represented by the general formula (2) is preferably used as a host material or an assist material in an organic light-emitting device. The organic compound represented by the general formula (2) is preferably used as a host material for a blue light-emitting layer or a green light-emitting layer in an organic light-emitting device.

Specific examples of organic compounds according to the present invention are shown below. However, the present invention is not limited to these.

The exemplified compounds belonging to Group A are a compound group having at least one substituent selected from R ₂₂ , R ₂₃ , R ₂₇ , R ₃₀ , R ₃₁ , and R ₃₅ in general formula (3), and X ₁ and X ₂ are oxygen. Among the organic compounds according to the present invention, the compounds in Group A have a basic skeleton with higher planarity than the other groups, and therefore have the effect of having the shortest emission wavelength and high color purity.

Among the exemplary compounds belonging to group B, the organic compounds excluding B37 to B40 have a substituent in general formula (3) in which at least one of _R22 , _R23 , _R27 , _R30 , _R31 , or _R35 has a substituent. Furthermore, this is a compound group in which _X1 and _X2 are oxygen atoms, sulfur atoms, selenium atoms, or tellurium atoms. Among the organic compounds according to the present invention, the compound group in group B has a feature that the HOMO and LUMO are low (far from the vacuum level), and has the effect of being stable against oxidation.

Among the exemplary compounds belonging to group B, the organic compounds represented by B37 to B40 are a group of compounds in which _X1 or _X2 is a methylene group in general formula (1). When _X1 or _X2 is a methylene group, molecular association can be reduced. Therefore, the compounds are less susceptible to concentration quenching.

The organic compounds excluding C12 and C20 among the exemplary compounds belonging to Group C are organic compounds represented by general formula (3) in which at least one of R ₂₁ and R ₂₉ has a substituent. Among the organic compounds according to the present invention, the compounds in Group C have an effect of suppressing intermolecular stacking in a thin film state and suppressing concentration quenching of luminescence by twisting the basic skeleton and the substituent due to steric hindrance.

Among the exemplary compounds belonging to Group C, C12 and C20 are compounds in which any one pair of _R9 and _R10 , or _R19 and _R20 in the general formula (1) is bonded to form a condensed ring structure. C12 and C20 have the effect of emitting light of a short wavelength.

The exemplary compounds belonging to Group D are a group of compounds having substituents at R ₂₆ and R ₃₄ in general formula (3). Among the organic compounds according to the present invention, the group of compounds in Group D are a group of compounds having excellent durability because they have substituents at R ₂₆ and R _34. In addition, because the substituents are aryl groups, the compounds have high planarity and are also excellent in color purity.

The exemplary compounds belonging to group E are a group of compounds having a halogen group, a deuterium substituent, a silyl group, an alkoxy group, a cyano group, or a heteroaryl group as a substituent. Among the organic compounds according to the present invention, the group of compounds in group E has the effect of being able to adjust the HOMO and LUMO.

The exemplary compounds belonging to group F are a group of compounds represented by general formula (2). The exemplary compounds belonging to group F have a basic skeleton composed of a six-membered ring, and therefore exhibit a particularly high T1.

(2) Details of the organic light-emitting element Next, the organic light-emitting element according to this embodiment will be described. The organic light-emitting element according to 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 according to this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers as long as it has a light-emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have a hole injection layer, a hole transport layer, an electron blocking layer, a hole-exciton blocking layer, an electron transport layer, an electron injection layer, etc. in addition to the light-emitting layer. The light-emitting layer may be a single layer or a laminate consisting of multiple layers.

In the organic light-emitting device according to this embodiment, at least one of the organic compound layers contains the organic compound according to the present invention. Specifically, the organic compound according to the present invention 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 the present invention is preferably contained in the hole transport layer, electron blocking layer, hole/exciton blocking layer, electron transport layer, or light-emitting layer, and is particularly preferably contained in the light-emitting layer.

In the organic light-emitting device according to this embodiment, when the organic compound according to the present invention is contained in the light-emitting layer, the light-emitting layer may further contain a first compound (hereinafter, sometimes referred to as a "host material"). The first compound has an S1 higher than the S1 of the organic compound according to the present invention. The light-emitting layer may further contain a second compound (hereinafter, sometimes referred to as an "assist material"). It is preferable that the second compound has an S1 higher than the S1 of the organic compound according to the present invention and lower than the S1 of the first compound.

In the organic light-emitting device according to the present embodiment, when the organic compound according to the present invention is contained in the light-emitting layer, the light-emitting layer may be a layer consisting of only the organic compound according to the present invention, or may be a layer consisting of the organic compound according to the present invention and other compounds. Here, when the light-emitting layer is a layer consisting of the organic compound according to the present invention and other compounds, the organic compound according to the present invention may be used as a host material of the light-emitting layer, may be used as an assist material, or may be used as a guest material. When the organic compound according to the present invention is used as a host, it may contain a third compound (hereinafter, sometimes referred to as a "guest material" or "dopant material"). It is preferable that the third compound has a T1 lower than the S1 of the organic compound according to the present invention, and it is more preferable that the third compound has a T1 lower than the S1 of the organic compound according to the present invention. When the organic compound according to the present invention is used as an assist material, it may contain a first compound and a third compound. Here, the host is a compound having the largest mass ratio among the compounds constituting the light-emitting layer. Moreover, the assist material is a compound having a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer, and assists the emission of the guest. The assist material is also called a second host. The guest is a compound that is smaller in mass ratio than the host among the compounds that make up the light-emitting layer, and is the compound that is primarily responsible for emitting light.

When the organic compound according to the present invention is used as a guest in the light-emitting layer, the concentration of the guest is preferably 0.01% by mass or more and 30% by mass or less, and more preferably 2% by mass or more and 20% by mass or less, based on the entire light-emitting layer.

The present inventors have conducted various studies and found that when the organic compound according to the present invention is used as a host or guest of the light-emitting layer, particularly as a guest of the light-emitting layer, an element that exhibits high efficiency and high luminance light output and is extremely durable can be obtained. This light-emitting layer may be a single layer or multiple layers, and it is also possible to mix the light emitted by the light-emitting layer with the red light emitted in this embodiment by including a light-emitting material having another light-emitting color. Multiple layers means a state in which the light-emitting layer and another light-emitting layer are laminated. In this case, the light-emitting color of the organic light-emitting element is not limited to red. More specifically, it may be white or an intermediate color. In the case of white, the other light-emitting layer emits a color other than red, i.e., blue or green. In addition, the film is formed by deposition or coating. Details of this will be explained in detail in the examples described later.

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

Here, in addition to the organic compound according to the present invention, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. can be used together as necessary. Examples of these compounds are given below.

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

Among the hole transport materials listed above, HT16 to HT18 can reduce the driving voltage when used in a layer in contact with the anode. HT16 is widely used in organic light-emitting elements. HT2, HT3, HT4, HT5, HT6, HT10, and HT12 may be used in the organic compound layer adjacent to HT16. Also, multiple materials may be used in one organic compound layer.

Light-emitting materials that are primarily involved in the light-emitting function include condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives.

Specific examples of compounds that can be used as luminescent materials are shown below, but of course they are not limited to these.

When the luminescent material is a hydrocarbon compound, this is preferable because it can reduce the decrease in luminous efficiency due to exciplex formation and the decrease in color purity due to changes in the emission spectrum of the luminescent material due to exciplex formation.

Hydrocarbon compounds are compounds that are composed only of carbon and hydrogen, and among the above example compounds are BD7, BD8, GD5 to GD9, and RD1.

When the light-emitting material is a condensed polycyclic ring containing a five-membered ring, it is preferable because it has a high ionization potential, is less likely to oxidize, and results in an element with a long durability and life. Among the above example compounds, BD7, BD8, GD5 to GD9, and RD1 are preferred.

Examples of the light-emitting layer host or light-emitting assist material contained in the light-emitting layer include aromatic hydrocarbon compounds or their derivatives, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organic aluminum complexes such as tris(8-quinolinolato)aluminum, and organic beryllium complexes.

Specific examples of compounds that can be used as the light-emitting layer host or light-emitting assist material contained in the light-emitting layer are shown below, but the present invention is not limited to these.

When the host material is a hydrocarbon compound, the compound of the present invention is more likely to trap electrons and holes, and the effect of improving efficiency is greater. A hydrocarbon compound is a compound composed only of carbon and hydrogen, and among the above-mentioned exemplary compounds, EM1 to EM12 and EM16 to EM27 are mentioned. The host material preferably has an aryl group having 6 to 18 carbon atoms, and is more preferably a hydrocarbon compound. In addition, when the organic compound of the present invention is used as an assist material, the host material preferably has at least one of a pyrene skeleton, a triphenylene skeleton, and a chrysene skeleton. Among the above-mentioned exemplary compounds, EM1 to EM4, EM9 to EM12, EM26, and EM27 are mentioned.

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. Materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organic aluminum complexes, and condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transport materials are also suitable for use in hole blocking layers.

Specific examples of compounds that can be used as electron transport materials are shown below, but of course the materials are not limited to these.

The electron injection material can be selected from those that allow easy electron injection from the cathode, taking into consideration the balance with hole injection properties. 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.

It can also be used in combination with the above electron transport materials.

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

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

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

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

One of these electrode materials may be used alone, or two or more may be used in combination. The anode may be composed of a single layer or multiple layers.

When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates of these can be used. The above materials can also function as a reflective film without acting 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.

On the other hand, the material for the cathode should have a small work function. Examples of such materials include alkali metals such as lithium, alkaline earth metals such as calcium, aluminum, titanium, manganese, silver, lead, and chromium, or 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 may be used alone or in combination of two or more types. The cathode may have a single layer or a multilayer structure. Among these, it is preferable to use silver, and it is even more preferable to use a silver alloy to reduce the aggregation of silver. As long as the aggregation of silver can be reduced, the ratio of the alloy is not important. For example, the ratio of silver to other metal may be 1:1, 3:1, etc.

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.

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

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

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

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

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

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

It is also possible to define the midpoint of a microlens. In the cross section of the microlens, a line segment can be 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.

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

[Organic Layer]
The organic compound layers constituting the organic light-emitting device according to this embodiment (such as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer) are formed by the method described below.

The organic compound layer constituting the organic light-emitting device according to this embodiment can be formed using a dry process such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively, instead of a dry process, a wet process can be used in which the compound is dissolved in an appropriate solvent and a layer is formed using a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

If a layer is formed by vacuum deposition or solution coating, crystallization is unlikely to occur and the layer has excellent stability over time. When forming a film by coating, the film can also be formed by combining with an appropriate binder resin.

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, urea resin, etc.

These binder resins may be used alone as homopolymers or copolymers, or two or more types may be mixed together. If necessary, known additives such as plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.

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

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 the transistors constituting the pixel circuit may be smaller than the mobility of the transistors constituting the display control circuit.

The slope of the current-voltage characteristics of the transistors that make up the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistors that make up the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics.

The transistors that make up the pixel circuit are transistors that are connected to a light-emitting element, such as the first light-emitting element.

[Pixels]
An organic light emitting device includes a plurality of pixels, each of which includes sub-pixels that emit different colors, for example, each of which may emit RGB colors.

A pixel emits light in an area also called the pixel aperture. This area is the same as the first area. The pixel aperture may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc.

The distance between subpixels may be 10 μm or less, specifically 8 μm, 7.4 μm, or 6.4 μm.

The pixels may have a known arrangement in plan view. For example, they may be a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in plan view may be any known shape. For example, they may be rectangular, quadrilaterals such as diamonds, or hexagons. Of course, any shape 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.

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

The display device may be an image information processing device that has an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., has an information processing unit that processes the input information, and displays the input image on the display unit.

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

Next, the display device according to this embodiment will be described with reference to the drawings.

Figure 1 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin-film transistor (TFT).

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

The interlayer insulating layer 1 may have a transistor and a capacitance element disposed underneath or inside it. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

The insulating layer 3 is also called a bank or pixel separation film. It covers the edge of the first electrode and is disposed so as to surround the first electrode. The part where the insulating layer is not disposed contacts the organic compound layer 4 and becomes the light-emitting region.

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

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

The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is illustrated as being a single layer, it may be multiple layers. Each layer may include an inorganic compound layer and an organic compound layer.

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

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

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

In the display device 100 of FIG. 1(b), the organic compound layer is illustrated as one layer, but the organic compound layer 22 may be multiple layers. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element.

In the display device 100 of FIG. 1(b), a transistor is used as the switching element, but other switching elements may be used instead.

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

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

The organic light-emitting element according to this embodiment has its light emission brightness controlled by a TFT, which is an example of a switching element, and by providing the organic light-emitting element on multiple surfaces, an image can be displayed with the respective light emission brightnesses. Note that the switching element according to this embodiment is not limited to a TFT, and may 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 within the substrate. Whether to provide a transistor within the substrate or to use a TFT is selected according to the size of the display unit, and for example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

Figure 2 is a schematic diagram showing an example of a display device according to this embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The display panel 1005 may have an organic light-emitting element according to this embodiment. The touch panel 1003 and the display panel 1005 are connected to flexible printed circuits FPCs 1002 and 1004, respectively. A transistor is printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position even if the display device is a portable device.

The display device according to this embodiment may have a color filter having red, green, and blue colors. The color filters may be arranged such that the red, green, and blue colors are arranged in a delta arrangement.

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

The display device according to this embodiment may be used in the display section of an imaging device having an imaging element that receives light. The imaging device may have a display section that displays information acquired by the imaging element. The display section may be a display section that is exposed to the outside of the imaging device, or a display section that is arranged within the viewfinder. The imaging device may be a digital camera or a digital video camera.

FIG. 3(a) is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may have a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 and the rear display 1102 may have an organic light-emitting element according to this embodiment. In this case, the viewfinder 1101 and the rear display 1102 may display not only the image to be captured, but also environmental information, imaging instructions, etc. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject moves, the possibility that the subject will be blocked by an obstruction, etc.

The optimal timing for capturing an image is very short, so it is better to display the information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting elements according to this embodiment. This is because organic light-emitting elements have a fast response speed. A display device using organic light-emitting elements can be used more preferably than liquid crystal display devices, which require high display speed.

The imaging device 1100 may further have an optical section (not shown). The optical section may have a single lens or 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 be called a photoelectric conversion device. Rather than capturing images sequentially, 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 recorded.

FIG. 3B is a schematic diagram showing an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit may be a biometric recognition unit that recognizes a fingerprint and performs unlocking, etc. An electronic device having a communication unit can also be called a communication device. The electronic device 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. Examples of the electronic device include a smartphone and a laptop computer.

Figure 4 is a schematic diagram showing an example of a display device according to this embodiment. Figure 4(a) shows a display device such as a television monitor or a PC monitor. The display device 1300 has a housing 1301 and a display unit 1302. The organic light-emitting element according to this embodiment may be used in the display unit 1302.

The display device 1300 has a housing 1301 and a base 1303 that supports a display unit 1302. The base 1303 is not limited to the form shown in FIG. 4(a). The bottom side of the housing 1301 may also serve as the base.

The housing 1301 and the display unit 1302 may also be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

Figure 4 (b) is a schematic diagram showing another example of a display device according to this embodiment. The display device 1310 in Figure 4 (b) is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have an organic light-emitting element according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single display unit without a joint. 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.

5A is a schematic diagram showing an example of an illumination device according to the present embodiment. The illumination device 1400 may have a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may have an organic light-emitting element according to the present embodiment. The illumination device 1400 may have an optical film 1404 to improve the color rendering of the light source. The illumination device 1400 may also have a light diffusion section 1405 to effectively diffuse the light of the light source. By having the light diffusion section 1405, the illumination device 1400 can deliver light over a wide range. The optical film 1404 and the light diffusion section 1405 may be provided on the light emission side of the illumination. If necessary, a cover may be provided on the outermost part.

The lighting device is, for example, a device that illuminates a room. The lighting device may emit white light, daylight white light, or any other color from blue to red. It may have a dimming circuit that adjusts the light intensity. The lighting device may have a power supply circuit. The power supply circuit may be a circuit that converts AC voltage to DC voltage. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device may have a color filter.

The lighting device according to this embodiment may also have a heat dissipation section. The heat dissipation section dissipates heat from within the device to the outside, and is made of metal or ceramic with high thermal conductivity.

Figure 5(b) is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has tail lamps, which are an example of a lamp. The automobile 1500 has tail lamps 1501, and may be a mobile phone in which the tail lamps are turned on when the brakes are applied, etc. The automobile 1500 may have a body 1503 and a window 1502 attached thereto.

The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp may have a protective member that protects the light source. The protective member may be made of any material as long as it has a relatively high strength and is transparent, but it is preferable that the protective member is made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

The moving body according to this embodiment may be an automobile, a ship, an aircraft, a drone, etc. The moving body may have a body and a lamp provided on the body. The lamp may emit light to indicate the position of the body.

The electronic device or display device can be applied to a system that can be attached as a wearable device such as smart glasses, a head-mounted display, or smart contacts. The electronic device may have an imaging device capable of photoelectric conversion of visible light, and a display device capable of emitting visible light.

Figure 6 is a schematic diagram showing an example of glasses (smart glasses) according to this embodiment. Glasses 1600 (smart glasses) will be described using Figure 6 (a). Glasses 1600 have a display unit on the back side of lens 1601. The display unit may have an organic light-emitting element according to the present invention. Furthermore, an imaging device 1602 such as a CMOS sensor or SPAD may be provided on the front side of lens 1601.

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 unit. The control device 1603 also controls the operation of the image capture device 1602 and the display unit. The lens 1601 is formed with an optical system for focusing light from the image capture device 1602 and the display unit.

The glasses 1610 (smart glasses) will be described with reference to FIG. 6(b). The glasses 1610 have a control device 1612, and the control device 1612 is provided with a display device having an organic light-emitting element according to the present invention. The control device 1612 may further have an imaging device corresponding to the imaging device 1602. The lens 1611 is formed with an optical system for projecting light emitted from the control device 1612, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operation of the imaging device and the display device. The control device may have a line of sight detection unit that detects the line of sight of the vehicle in which the glasses are mounted. The line of sight may be detected using infrared rays. The infrared light emitting unit emits infrared rays to the eyeball of a user who is gazing at a displayed image. Of the emitted infrared light, the imaging unit having a light receiving element detects the reflected light from the eyeball, thereby obtaining an image of the eyeball. By having a reduction means for reducing the light from the infrared light emitting unit to the display unit in a planar view, the deterioration of image quality is reduced.

The control device 1612 detects the user's line of sight with respect to the displayed image 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 can be used based on the Purkinje image formed by reflection of irradiated light on the cornea.

More specifically, gaze detection processing is performed based on the pupil-corneal reflex method. Using the pupil-corneal reflex method, a gaze vector that represents the direction (rotation angle) of the eyeball is generated based on the pupil image and Purkinje image contained in the captured image of the eyeball, thereby detecting the user's gaze.

A display device according to one embodiment of the present invention may have 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 on which the user gazes and a second field of view area other than the first field of view area based on the line of sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be received from an external control device. In the display area of the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than the first field of view area.

AI may be used to determine the first display area or the display area with high priority. The AI may be a model configured to estimate the angle of the line of sight and the distance to an object in the line of sight from the image of the eyeball, using as teacher data an image of the eyeball and the direction in which the eyeball in the image was actually looking. The AI may be included in the display device, the imaging device, or an external device. When the external device includes AI, it is preferably applicable to smart glasses that further include an imaging device that captures images of the outside. The smart glasses can display captured external information in real time.

Figure 7 (a) is a schematic diagram showing an example of an image forming apparatus according to this embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus, and has 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. This exposure light source 28 may have an organic light-emitting element according to this embodiment. The developing unit 31 has toner, etc. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a storage 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.

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

As explained above, by using a 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 long periods of time.

The present invention will be explained below with reference to examples. However, the present invention is not limited to these examples.

[Example 1 (Synthesis of Exemplary Compound A1)]

(1) Synthesis of Compound H3 The following reagents and solvent were placed in a 500 ml recovery flask.
Compound H1: 500mg (1.73mmol)
Compound H2: 1.33g (6.94mmol)
Pd(dba) ₂ : 45mg (0.09mmol)
DPPF: 143mg (0.27mmol)
t-BuONa: 664 mg (6.92 mmol)
Toluene: 200 ml

Next, the reaction solution was heated to 110°C under a nitrogen stream and stirred at this temperature (110°C) for 5 hours. After the reaction was completed, the solution was extracted with toluene and water, concentrated, and purified by silica gel column chromatography (toluene), yielding 546 mg of compound H3 (yield: 62%).

(2) Synthesis of Exemplary Compound A1 The following reagents and solvent were placed in a 100 ml recovery flask.
Compound H1: 500 mg (0.98 mmol)
Pd(OAc) ₂ : 6 mg (0.03 mmol)
P(t-Bu)3: 20mg (0.09mmol)
DBU: 596mg (3.92mmol)
o-xylene: 30 ml

Next, the reaction solution was heated to 140°C under a nitrogen stream and stirred at this temperature (140°C) for 6 hours. After the reaction was completed, methanol was added, filtered, and washed with water and methanol. After purifying this by silica gel column chromatography (chlorobenzene), 47 mg of exemplary compound A1 (yield: 11%) was obtained.

Exemplary compound A1 was subjected to mass spectrometry using MALDI-TOF-MS (Bruker Autoflex LRF).

[MALDI-TOF-MS]
Measured value: m/ _{z = 436 Calculated value: C42H24B2N4 = 436}

[Examples 2 to 31 (Synthesis of Exemplary Compounds)]
The exemplary compounds shown in Examples 2 to 31 were synthesized in the same manner as in Example 1, except that the raw material H1 in Example 1 was replaced with raw material 1 and the raw material H2 was replaced with raw material 2. Raw materials 1 and 2 in each Example are shown in Tables 4-1 to 4-6.

The actual measured value (m/z) of the mass spectrometry results measured in the same manner as in Example 1 is also shown.

[Example 32]
In this example, an organic EL element having a bottom emission structure was produced 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 successively formed on a substrate.

First, an ITO film was formed on a glass substrate, and an ITO electrode (anode) was formed by performing a desired patterning process. At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed in this manner was used as an ITO substrate in the following process. Next, vacuum deposition was performed by resistance heating in a vacuum chamber to continuously form an organic compound layer and an electrode layer shown in Table 5 on the ITO substrate. At this time, the electrode area of the opposing electrodes (metal electrode layer, cathode) was set to 3 ^mm2 .

The characteristics of the obtained element were measured and evaluated. When the emission spectrum of the light-emitting element was confirmed at a luminance of 1000 cd/ ^m2 , blue light was emitted. Specifically, the current-voltage characteristics were measured using a microammeter 4140B manufactured by Hewlett-Packard, and the emission luminance was measured using a BM7 manufactured by Topcon. Furthermore, a continuous driving test was performed at a current density of 20 mA/ ^cm2 , and the time (LT95) at which the luminance degradation rate from the initial luminance reached 5% was measured, which was 130 hours.

[Examples 33 to 51, Comparative Example 1]
An organic light-emitting device was produced in the same manner as in Example 32, except that the compounds were appropriately changed to those shown in Table 6. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 32. The measurement results are shown in Table 6.

From Table 6, the element using the organic compound according to the present invention showed good durability. This is because the compound according to the present invention has a skeleton in which at least one of the substituents that substitute for each of the two nitrogen atoms in the main skeleton is fused to the main skeleton, and thus can obtain blue light emission with a narrow half-width and excellent color purity. Furthermore, the fused ring structure has a C-C bond with high bond energy, so the molecular structure is highly stable and showed excellent durability. On the other hand, the emission color of Comparative Example 1 using Comparative Compound 1-a described in Patent Document 1 is light blue and the half-width is also large. The LT95 of Comparative Compound 1-a is 75 hours, which is not preferable compared to the color purity, current efficiency, and durability of the blue light-emitting element of this example.

[Example 52]
An organic light-emitting device was produced in the same manner as in Example 32, except that the compounds were appropriately changed to those shown in Table 7. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 32.

The characteristics of the obtained element were measured and evaluated. The measurement results are shown in Table 8. As a result, good green light emission was obtained from the light-emitting element. Specifically, the current-voltage characteristics were measured using a microammeter 4140B manufactured by Hewlett-Packard, and the luminance was measured using a BM7 manufactured by Topcon. Furthermore, a continuous driving test was performed at a current density of 10 mA/ ^cm2 , and the LT95 was measured, which exceeded 500 hours.

[Examples 53 to 64, Comparative Example 2]
An organic light-emitting device was produced in the same manner as in Example 54, except that the compounds were appropriately changed to those shown in Table 8. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 54. The measurement results are shown in Table 8.

As can be seen from Table 8, the LT95 of the element using the organic compound according to the present invention exceeds 500 hours, and the element using the organic compound according to the present invention has excellent durability characteristics. On the other hand, the LT95 of the organic light-emitting element of Comparative Example 2 is less than 500 hours, and has poor durability characteristics, which is not preferable.

[Example 65]
In this example, an organic EL element having a top emission structure was produced in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a first emitting layer, a second emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were successively formed on a substrate.

A 40 nm thick laminated film of Al and Ti was formed on a glass substrate by sputtering, and patterned using photolithography to form an anode. At this time, the electrode area of the opposing electrodes (metal electrode layer, cathode) was set to 3 mm ^2. Next, the substrate and material on which the cleaned electrodes were formed were attached to a vacuum deposition apparatus (manufactured by ULVAC), and the vacuum was evacuated to 1.3×10 ⁻⁴ Pa (1×10 ⁻⁶ Torr), after which UV/ozone cleaning was performed. Thereafter, each layer was formed in the layer configuration shown in Table 9, and finally, sealing was performed under a nitrogen atmosphere.

The characteristics of the obtained element were measured and evaluated. The obtained element emitted white light with excellent color purity. Furthermore, a continuous driving test was performed at an initial luminance of 1000 cd/ ^m2 , and the luminance degradation rate after 100 hours was measured, which was 26%.

[Examples 66 to 68, Comparative Example 3]
An organic light-emitting device was produced in the same manner as in Example 66, except that the compounds were appropriately changed to those shown in Table 10. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 66. The measurement results are shown in Table 10.

As can be seen from Table 10, elements using the organic compound of the present invention have excellent durability. This is because the compound of the present invention has a structure in which at least one of the substituents on the two nitrogen atoms in the main skeleton is fused to the main skeleton, making the substituents less likely to dissociate and resulting in a highly stable molecular structure. On the other hand, the luminance degradation rate of the organic light-emitting element using the comparative compound 1-a was 52%. This is because when the comparative compound 1-a is used as a guest, the substituents on the two nitrogen atoms in the main skeleton are not fused to the main skeleton, making the substituents more likely to dissociate and resulting in a less stable molecular structure.

[Example 69]

(1) Synthesis of Compound H7 The following reagents and solvent were placed in a 300 ml recovery flask.
Compound H5: 2.00 g (6.50 mmol)
Compound H6: 2.98g (13.0mmol)
Pd(OAc) ₂ : 69mg (0.05mmol)
P(t-Bu) ₃ : 217 mg (0.09 mmol)
NaOtBu: 2.50g (26.0mmol)
o-xylene: 150 ml

Next, the reaction solution was heated to 140°C under a nitrogen stream and stirred at this temperature (140°C) for 6 hours. After the reaction was completed, water was added and the organic layer was extracted with toluene. After purifying this by silica gel column chromatography (toluene, heptane), 943 mg of compound H7 (yield: 24%) was obtained.

(2) Synthesis of Compound H8 The following reagents and solvent were placed in a 50 ml recovery flask.
1-Decanthiol: 389 mg (2.23 mmol)
KOtBu: 250mg (2.23mmol)
DMF: 10 ml

Next, the mixture was stirred at room temperature for 15 minutes, and the following compound was added to the reaction mixture.
Compound H7: 900mg (1.49mmol)

Next, the reaction solution was heated to 110°C under a nitrogen stream and stirred at this temperature (110°C) for 3 hours. After the reaction was completed, water was added at room temperature, and 1M hydrochloric acid was added dropwise until the pH reached 1. The organic layer was extracted from this mixture with ethyl acetate. After concentrating the organic layer, it was dispersed and washed with heptane to obtain 482 mg of compound H8 (yield: 59%).

(3) Synthesis of Exemplary Compound F1 The following reagents and solvent were placed in a 100 ml recovery flask.
Compound H8: 450 mg (0.82 mmol)
_K2CO3 : _735mg (6.56mmol)
DMAc: 20 ml

Next, the reaction solution was heated to 120°C under a nitrogen stream and stirred at this temperature (120°C) for 4 hours. After the reaction was completed, water was added at room temperature and filtered to obtain a crude product. This crude product was dispersed with silica gel in xylene solvent at 120°C and filtered through Celite. The filtrate was concentrated and washed with toluene:ethanol (volume ratio 1:1) to obtain 46 mg of exemplary compound F1 (yield: 12%).

Exemplary compound F1 was subjected to mass spectrometry using MALDI-TOF-MS (Bruker Autoflex LRF).

[MALDI-TOF-MS]
Measured value: m/ _{z = 468 Calculated value: C30H16N2O4 = 468}

[Examples 70 to 84 (Synthesis of Exemplary Compounds)]
The exemplary compounds shown in Examples 70 to 84 were synthesized in the same manner as in Example 69, except that the raw material H6 in Example 69 was changed to raw material 3. Raw material 3 for each Example is shown in Tables 11-1 and 11-2.

The actual measured value (m/z) of the mass spectrometry results measured in the same manner as in Example 69 is also shown.

[Examples 85 to 95]
An organic light-emitting device was produced in the same manner as in Example 32, except that the compounds shown in Table 12 were appropriately changed.

The characteristics of the obtained element were measured and evaluated. The measurement results are shown in Table 12. Specifically, the current-voltage characteristics were measured using a microammeter 4140B manufactured by Hewlett-Packard, and the luminance was measured using a BM7 manufactured by Topcon. Furthermore, a continuous driving test was performed at a current density of 100 mA/ ^cm2 , and the LT95 was measured. The measurement results are shown in Table 12. The parentheses in the table indicate the concentration of the compound in the light-emitting layer.

From Table 12, the LT95 of the organic light-emitting element using the organic compound according to the present invention as the second host (assist material) for the blue guest exceeded 10 hours. Furthermore, the LT95 of the organic light-emitting element using the organic compound according to the present invention as the second host (assist material) for the green guest was about 10 hours. Furthermore, the organic light-emitting element using the organic compound according to the present invention as the EBL exhibited particularly excellent durability characteristics among the organic light-emitting elements listed in Table 12. From the above, it was found that the organic light-emitting element using the organic compound according to the present invention has excellent durability characteristics.

As described above, the organic compound according to the present invention is capable of emitting blue light with excellent color purity and also has excellent durability. Furthermore, when the organic compound according to the present invention is used as a host material, an assist material, or an electron blocking material, it is possible to provide an organic light-emitting device with excellent durability.

The present invention can also have the following configurations:

(Configuration 1)
An organic compound represented by general formula (1):

(In the general formula (1), R ₁ to R ₂₀ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a cyano group. R ₁ to R ₂₀ may be bonded to each other to form a ring. The bond may be via a chalcogen atom. At least one of the combinations of R ₉ and R ₁₀ , and R ₁₉ and R ₂₀ are bonded to each other. _{X 1} and X ₂ are each independently selected from the group consisting of a chalcogen atom, a substituted or unsubstituted imino group, a substituted or unsubstituted methylene group, and a substituted or unsubstituted silylene group.)

(Configuration 2)
The organic compound according to the structure 1, characterized in that the organic compound is represented by general formula (2) or (3).

(In general formulas (2) and (3), R ₂₁ to R ₃₆ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a cyano group. R ₂₁ to R ₃₆ may be bonded to each other to form a ring. The bond may be via a chalcogen atom. _{X 1} to X ₄ are each independently selected from the group consisting of a chalcogen atom, a substituted or unsubstituted imino group, a substituted or unsubstituted methylene group, and a substituted or unsubstituted silylene group.)

(Configuration 3)
In the general formulas (2) and (3), at least one of R ₂₁ , R ₂₂ , R ₂₃ , R ₂₆ , R _{27 , R 29 ,} R ₃₀ , R ₃₁ , R ₃₄ , and R ₃₅ is other than a hydrogen atom.

(Configuration 4)
In the general formulas (2) and (3), at least one of R ₂₁ , R ₂₂ , R ₂₃ , R ₂₆ , R ₂₇ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₄ , and R ₃₅ is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms.

(Configuration 5)
In the general formulas (2) and (3), the substituents represented by R ₂₇ and R ₃₅ are an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms.

(Configuration 6)
6. The organic compound according to any one of structures 2 to 5, wherein in general formulae (2) and (3), X ₁ to X ₄ are oxygen atoms or sulfur atoms.

(Configuration 7)
7. The organic compound according to any one of structures 2 to 6, wherein in general formulae (2) and (3), the compound does not have a structure of general formula (4).

In the general formula (4), _X5 and _X6 are each independently selected from the group consisting of an oxygen atom, a sulfur atom, a dimethylmethylene group, a sulfonyl group, and the general formula (5). * represents the bonding position with _R26 and _R34 , and *' represents the bonding position with _R27 and _R35 .

In formula (5), R ₄₁ is a phenyl group. * indicates the bonding position.

(Configuration 8)
A first electrode and a second electrode,
an organic compound layer disposed between the first electrode and the second electrode,
The organic compound layer comprises the organic compound according to any one of the first to seventh aspects of the present invention.

(Configuration 9)
the organic compound layer has a light-emitting layer,
The organic light-emitting element according to Structure 8, wherein the light-emitting layer contains the organic compound.

(Configuration 10)
the light-emitting layer further comprises a first compound;
The organic light-emitting device according to Structure 9, wherein the first compound has a minimum excited singlet energy higher than that of the organic compound.

(Configuration 11)
11. The organic light-emitting device according to claim 10, wherein the first compound has an aryl group having 6 to 18 carbon atoms.

(Configuration 12)
12. The organic light-emitting device according to claim 10, wherein the first compound is a hydrocarbon compound.

(Configuration 13)
13. The organic compound according to any one of structures 10 to 12, wherein the first compound has at least one of a pyrene skeleton, a triphenylene skeleton, and a chrysene skeleton.

(Configuration 14)
the light-emitting layer further comprises a third compound;
14. The organic light-emitting element according to any one of Structures 10 to 13, wherein the lowest excited singlet energy of the third compound is lower than the lowest excited singlet energy of the organic compound.

(Configuration 15)
15. The organic light-emitting device according to Structure 14, wherein the lowest excited triplet energy of the third compound is lower than the lowest excited triplet energy of the organic compound.

(Configuration 16)
16. The organic light-emitting device according to claim 14, wherein the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the third compound.

(Configuration 17)
17. A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to any one of configurations 8 to 16 and a transistor connected to the organic light-emitting element.

(Configuration 18)
an optical unit having a plurality of lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays an image captured by the image sensor;
17. A photoelectric conversion device, wherein the display section has the organic light-emitting element according to any one of configurations 8 to 16.

(Configuration 19)
17. An electronic device comprising: a display unit having the organic light-emitting element according to any one of configurations 8 to 16; a housing in which the display unit is provided; and a communication unit provided in the housing and configured to communicate with an external device.

(Configuration 20)
17. A lighting device comprising: a light source having the organic light-emitting element according to any one of configurations 8 to 16; and a light diffusion section or an optical film that transmits light emitted by the light source.

(Configuration 21)
17. A moving body comprising: a lighting device having the organic light-emitting element according to any one of configurations 8 to 16; and a body on which the lighting device is provided.

(Configuration 22)
A photoconductor and an exposure light source for exposing the photoconductor,
17. An image forming apparatus comprising: an exposure light source having the organic light-emitting element according to any one of configurations 8 to 16.

(Configuration 23)
17. A wearable device comprising: a display unit having the organic light-emitting element according to any one of configurations 8 to 16; an optical system that collects light from the display unit; and a control device that controls display of the display unit.

LIST OF REFERENCE NUMERALS 1 Interlayer insulating layer 2 Reflective electrode 3 Insulating layer 4 Organic compound layer 5 Transparent 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 Thin film transistor 19 Insulating film 20 Contact hole 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting element 100 Display device 1000 Display device 1001 Upper cover 1002 Flexible printed circuit 1003 Touch panel 1004 Flexible printed circuit 1005 Display panel 1006 Frame 1007 Circuit board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation unit 1104 Housing 1200 Electronic device 1201 Display unit 1202 Operation unit 1203 Housing 1300 Display device 1301 Housing 1302 Display unit 1303 Base 1310 Display device 1311 First display unit 1312 Second display unit 1313 Housing 1314 Bend point 1400 Illumination device 1401 Housing 1402 Light source 1403 Circuit board 1404 Optical film 1405 Light diffusion unit 1500 Automobile 1501 Tail lamp 1502 Window 1503 Vehicle body 1600 Smart glasses 1601 Lens 1602 Imaging device 1603 Control device 1610 Smart glasses 1611 Lens 1612 Control device

Claims (35)

An organic compound represented by general formula (1):

(In general formula (1), R ₁ to R ₂₀ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a cyano group. _{R 1} to R ₂₀ may be bonded to each other to form a ring. The bond may be via a chalcogen atom. At least one of the combinations of R ₉ and R ₁₀ and R ₁₉ and R ₂₀ is bonded to each other to form a 5-membered ring or a 6-membered ring . _{X 1} and X ₂ are each independently selected from the group consisting of a chalcogen atom and a substituted or unsubstituted silylene group.) In the general formula (1), R ₉ and R ₁₀ When R is bonded ₄ and R ₅ does not bond, R ₁₉ and R ₂₀ When R is bonded ₁₄ and R ₁₅ The organic compound according to claim 1, characterized in that: 2. The organic compound according to claim 1, which is represented by general formula (2) or (3).

(In general formulas (2) and (3), R ₂₁ to R ₃₆ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a cyano group. R ₂₁ to R ₃₆ may be bonded to each other to form a ring. The bond may be via a chalcogen atom. X ₃ and X ₄ are each independently selected from the group consisting of a chalcogen atom, a substituted or unsubstituted methylene group, and a substituted or unsubstituted silylene group.) In the general formulas (2) and (3), R ₂₄ and R ₂₅ , and R ₃₂ and R ₃₃ The organic compound according to claim 3, characterized in that: The organic compound according to claim 3, characterized in that, in general formulas (2) and (3), at least one of R ₂₁ , R ₂₂ , R ₂₃ , R ₂₆ , R ₂₇ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₄ , or R ₃₅ is other than a hydrogen atom. The organic compound according to claim 3, characterized in that, in general formulas (2) and (3), at least one of R ₂₁ , R ₂₂ , R ₂₃ , R ₂₆ , R ₂₇ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₄ , or R ₃₅ is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms. The organic compound according to claim 3, characterized in that in general formulas (2) and (3), the substituents represented by R ₂₇ and R ₃₅ are an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms. 4. The organic compound according to claim 3 , wherein in the general formulae (2) and (3), X ₁ to X ₄ are oxygen atoms or sulfur atoms. In the general formulas (2) and (3), X ₁ and X ₂ The organic compound according to claim 3, characterized in that is an oxygen atom. 4. The organic compound according to claim 3 , which does not have a structure of general formula (4) in general formulas (2) and (3).

In the general formula (4), _X5 and _X6 are each independently selected from the group consisting of an oxygen atom, a sulfur atom, a dimethylmethylene group, a sulfonyl group, and the general formula (5). * represents the bonding position with _R26 and _R34 , and *' represents the bonding position with _R27 and _R35 .
In formula (5), R ₄₁ is a phenyl group. * indicates the bonding position. A first electrode and a second electrode,
an organic compound layer disposed between the first electrode and the second electrode,
The organic compound layer comprises the organic compound according to claim 1 . the organic compound layer has a light-emitting layer,
The organic light-emitting device according to claim 11 , wherein the light-emitting layer comprises the organic compound. the light-emitting layer further comprises a first compound;
The organic light-emitting device according to claim 12 , wherein the first compound has a minimum excited singlet energy higher than that of the organic compound. The organic light-emitting device according to claim 13 , wherein the first compound is a hydrocarbon compound. The organic compound according to claim 13 , wherein the first compound has at least one of a pyrene skeleton, a triphenylene skeleton, and a chrysene skeleton. the light-emitting layer further comprises a third compound;
The organic light-emitting device according to claim 13 , wherein the lowest excited singlet energy of the third compound is lower than the lowest excited singlet energy of the organic compound. The organic light-emitting device according to claim 16 , wherein the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the third compound. A first electrode and a second electrode;
an organic compound layer disposed between the first electrode and the second electrode,
the organic compound layer has a light-emitting layer,
The light-emitting layer comprises an organic compound represented by general formula (1) and a first compound,
the first compound has at least one of a pyrene skeleton, a triphenylene skeleton, and a chrysene skeleton,
The organic light-emitting device is characterized in that the organic compound is not Compound 11.

(In the general formula (1), R ₁ or R ₂₀ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a cyano group. ₁ or R ₂₀ may be bonded to each other to form a ring. The bond may be via a chalcogen atom. ₉ and R ₁₀ , R ₁₉ and R ₂₀ At least one of the combinations of X is bonded to each other to form a 5-membered or 6-membered ring. ₁ and X ₂ are each independently selected from the group consisting of a chalcogen atom, a substituted or unsubstituted methylene group, and a substituted or unsubstituted silylene group. The organic light-emitting device according to claim 18 , wherein the organic compound is represented by general formula (2) or (3).

(In the general formulas (2) and (3), R ₂₁ or R ₃₆ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a cyano group. ₂₁ or R ₃₆ may be bonded to each other to form a ring. The bond may be via a chalcogen atom. ₃ and X ₄ are each independently selected from the group consisting of a chalcogen atom, a substituted or unsubstituted methylene group, and a substituted or unsubstituted silylene group. In the general formulas (2) and (3), R ₂₁ , R ₂₂ , R ₂₃ , R ₂₆ , R ₂₇ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₄ , or R ₃₅ The organic light-emitting element according to claim 19 , wherein at least one of the groups is other than a hydrogen atom. In the general formulas (2) and (3), R ₂₁ , R ₂₂ , R ₂₃ , R ₂₆ , R ₂₇ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₄ , or R ₃₅ 20. The organic light-emitting device according to claim 19, wherein at least one of the groups is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms. In the general formulas (2) and (3), R ₂₇ and R ₃₅ 20. The organic light-emitting element according to claim 19, wherein the substituent represented by the following formula is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms. In the general formulas (2) and (3), X ₁ to X ₄ The organic light-emitting element according to claim 19 , wherein is an oxygen atom or a sulfur atom. In the general formulas (2) and (3), X ₁ and X ₂ The organic compound according to claim 19, characterized in that is an oxygen atom. The organic light-emitting device according to claim 18, wherein the first compound has a minimum excited singlet energy higher than that of the organic compound. The organic light-emitting device according to claim 18 , wherein the first compound is a hydrocarbon compound. the light-emitting layer further comprises a third compound;
The organic light-emitting device according to claim 18, wherein the lowest excited singlet energy of the third compound is lower than the lowest excited singlet energy of the organic compound. The organic light-emitting device according to claim 27, wherein the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the third compound. 29. A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to claim 11 and a transistor connected to the organic light-emitting element. an optical unit having a plurality of lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays an image captured by the image sensor;
A photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to claim 11 . 29. An electronic device comprising: a display unit having the organic light-emitting element according to claim 11 ; a housing in which the display unit is provided; and a communication unit provided in the housing and configured to communicate with an external device. 29. A lighting device comprising: a light source having the organic light-emitting element according to claim 11 ; and a light diffusion section or an optical film that transmits light emitted by the light source. 29. A moving object comprising: a lighting device having the organic light-emitting element according to claim 11 ; and a body on which the lighting device is provided. A photoconductor and an exposure light source for exposing the photoconductor,
29. An image forming apparatus, comprising: said exposure light source comprising the organic light emitting element according to claim 11 . 29. A wearable device comprising: a display unit having the organic light-emitting element according to claim 11 ; an optical system for concentrating light from the display unit; and a control device for controlling display of the display unit.

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