Organic compound and organic light-emitting device

Abstract

To provide an organic compound which is excellent in element life characteristics when used in an organic light-emitting element.SOLUTION: The organic compound is represented by general formula [1]. Ar is selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group; R1 and R2 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group; and m and n are selected from integers of 1-3.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] An organic light-emitting element (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 a light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting element emits light. Recent advances in organic light-emitting devices have been remarkable, including low driving voltage, diverse emission wavelengths, high-speed response, and the possibility of thinning and reducing the weight of light-emitting devices. Furthermore, in terms of high efficiency, elements using highly efficient materials such as phosphorescent materials and delayed fluorescent materials can be cited. For organic light-emitting elements using such highly efficient materials, improving the durability of the elements is a development challenge. Various methods have been proposed to date to improve the durability of elements, one of which is stabilizing the structure of the materials that make up the light-emitting layer. Patent Document 1 describes the following compound 1-A.

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

[0004] [Patent Document 1] Korean Patent Publication No. 2014-091487 Summary of the Invention [Problem to be solved by the invention]

[0005] When the compound described in Patent Document 1 is used in an organic light-emitting device, the organic light-emitting device cannot have excellent durability. An object of the present invention is to provide an organic compound that, when used in an organic light-emitting device, has excellent device life characteristics. [Means for solving the problem]

[0006] An organic compound characterized by being represented by the following general formula [1].

[0007] [ka] In the general formula [1], Ar is selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group. R1 and R2 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. m, n are 1 is . The Ar the aryl group, the heteroaryl group, is the following [a] to [n] A substituted or unsubstituted group represented by is selected from. [ka] In the above [a] to [n], * indicates the bonding position to the naphthalene ring. [Effects of the Invention]

[0008] According to the present invention, an organic compound can be provided that, when used in an organic light-emitting device, has excellent device life characteristics. [Brief explanation of the drawings]

[0009] [Figure 1]1A is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention, and FIG. 1B is a schematic cross-sectional view showing an example of a display device using an organic light-emitting element according to one embodiment of the present invention. [Figure 2] 1 is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention. [Figure 3] 1A is a schematic diagram illustrating an example of an imaging device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of an electronic device according to an embodiment of the present invention. [Figure 4] 1A is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of a foldable display device. [Figure 5] 1A is a schematic diagram showing an example of an illumination device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing an example of a moving body having a vehicle lamp according to an embodiment of the present invention. [Figure 6] 1A is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. [Figure 7] 1A is a schematic diagram illustrating an example of an image forming apparatus according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of an exposure light source of the image forming apparatus according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

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

[0011] [ka]

[0012] Ar is bonded to one benzene ring of the naphthalene ring, and the phenanthro[4,5-bcd]thiophene ring (hereinafter sometimes referred to as the "phenanthrothiophene ring") is bonded to the other benzene ring. R1 is bonded to a position on the naphthalene ring other than the position bonded to Ar or the phenanthrothiophene ring. R2 is bonded to a position on the phenanthrothiophene ring other than the position bonded to the naphthalene ring.

[0013] When n is 2 or greater, each phenanthrothiophene ring may be the same or different. When m is 2 or greater, each Ar may be the same or different. Each R1 may be the same or different, and each R2 may be the same or different.

[0014] <ar> In the general formula [1], Ar is selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group.

[0015] Examples of the aryl group include aromatic hydrocarbon groups, such as a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a fluoranthenyl group, a triphenylenyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, and a perylenyl group, but are not limited to these.

[0016] Examples of heteroaryl groups include aromatic heterocyclic groups, such as pyridyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, phenanthrolyl, azaphenanthryl, dibenzofuranyl, dibenzothiophenyl, azatriphenylenyl, and diazatriphenylenyl groups, but are not limited to these.

[0017] Examples of substituents that the aryl group and heteroaryl group may further have include, but are not limited to, halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl, ethyl, normal propyl, isopropyl, normal butyl, and tertiary butyl; alkoxy groups such as methoxy, ethoxy, and propoxy; amino groups such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino; aryloxy groups such as phenoxy; aromatic hydrocarbon groups such as phenyl and biphenyl; heterocyclic groups such as pyridyl and pyrrolyl; and cyano group.

[0018] Ar is preferably a fused ring, more preferably a fused ring in which three or more five- or six-membered rings are fused, and even more preferably a fused ring in which four or more five- or six-membered rings are fused. Ar is also preferably a fused ring other than a phenanthrothiophenyl group.

[0019] Ar is preferably a phenanthryl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a fluoranthenyl group, an azaphenanthryl group, a phenanthrolyl group, or a diazatriphenylenyl group. Ar is more preferably selected from the following [a] to [n], and even more preferably selected from the following [a] to [f]. In the following [a] to [n], * represents the bonding position to the naphthalene ring.

[0020]

Chemical Structure

[0021] <R1 to R2> In General Formula [1], R1 to R2 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group.

[0022] When R1 is an aryl group or a heteroaryl group, it is preferable that the aryl group and the heteroaryl group are not condensed ring groups.

[0023] Examples of the halogen atom include, but are not limited to, fluorine, chlorine, bromine, iodine, etc.

[0024] Examples of the alkyl group include, but are not limited to, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, tertiary butyl group, secondary butyl group, octyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, etc. The number of carbon atoms of the alkyl group is preferably 1 or more and 10 or less.

[0025] Examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a benzyloxy group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 10.

[0026] Examples of the amino group include, but are not limited to, an N-methylamino group, an N-ethylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-methyl-N-ethylamino group, an N-benzylamino group, an N-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilino group, an N,N-diphenylamino group, an N,N-dinaphthylamino group, an N,N-difluorenylamino group, an N-phenyl-N-tolylamino group, an N,N-ditolylamino group, an N-methyl-N-phenylamino group, an N,N-dianisolylamino group, an N-mesityl-N-phenylamino group, an N,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, and an N-piperidyl group.

[0027] Examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0028] Examples of aryl groups include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, fluoranthenyl, and triphenylenyl groups.

[0029] Examples of heteroaryl groups include, but are not limited to, pyridyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, phenanthrolyl, dibenzofuranyl, and dibenzothiophenyl groups.

[0030] Examples of the aryloxy group and heteroaryloxy group include, but are not limited to, a phenoxy group and a thienyloxy group.

[0031] Examples of substituents that may be further substituted by the alkyl group, alkoxy group, amino group, silyl group, aryl group, heteroaryl group, aryloxy group, and heteroaryloxy group include, but are not limited to, the same as the substituents that may be further substituted by Ar.

[0032] <m,n> In the general formula [1], m and n are selected from integers of 1 or more and 3 or less.

[0033] <Synthesis method> Next, a method for synthesizing the organic compound according to this embodiment will be described. The organic compound according to this embodiment can be synthesized, for example, according to the reaction scheme shown below.

[0034] [ka]

[0035] Here, various compounds can be obtained by appropriately changing the compounds shown in (a), (d), and (f) above. The synthesis method is not limited to the above synthesis scheme, and various synthesis schemes and reagents can be used. The synthesis method will be described in detail in the Examples.

[0036] <Characteristics> Next, the properties of the organic compound according to this embodiment will be described. The organic compound according to this embodiment has the following characteristics, and therefore is a compound that is excellent in film formation and sublimation properties. Furthermore, by using this organic compound, it is possible to provide an organic light-emitting device that is excellent in luminous efficiency and device durability. (1) The dihedral angle between the naphthalene ring and the Ar group is large. (2) It has a low symmetry structure consisting of a phenanthrothiophene ring, a naphthalene ring, and an Ar group.

[0037] (1) The dihedral angle between the naphthalene ring and the Ar group is large In inventing the organic compound of this embodiment, the inventors focused on the dihedral angle formed between a naphthalene ring and an Ar group bonded to the naphthalene ring. Specifically, the organic compound of this embodiment has a structure consisting of a phenanthro[4,5-bcd]thiophene ring and a naphthalene ring, and a third ring, preferably a fused ring, with an Ar group, forming a dihedral angle with the rings on both sides of the naphthalene ring.

[0038] Here, the results of comparing the dihedral angles of Example Compound A25 and Example Compound A28 are shown in Table 1. Comparative Compound 1-A is Compound 1-A described in Patent Document 1. The dihedral angles related to the bond were visualized using molecular orbital calculations.

[0039] [Table 1]

[0040] In Table 1, the bond position with the largest dihedral angle between the fused ring and the naphthalene ring is designated a, and the dihedral angle is shown. The dihedral angle for Example Compound A25 is 56.6°, and for Example Compound A28, it is 55.6°. In contrast, for Comparative Compound 1-A, the dihedral angle is 52.1°. In all structures, steric hindrance exists between the peri-position hydrogen atom on the fused ring bonded to the naphthalene ring and the hydrogen atom on the naphthalene ring. In particular, the planarity alienating effect due to steric hindrance is greater in structures in which two aromatic fused rings, each with three or more rings fused to a naphthalene ring, are bonded. This is because the planarity alienating effect can be maximized by bonding a large aromatic fused ring consisting of three or more rings in space via a relatively small naphthalene ring. For this reason, it can be seen that Example Compound A25 and Example Compound A28 have larger dihedral angles than Comparative Compound 1-A. This means that exemplary compounds A25 and A28 have low planarity, and the vapor-deposited films are highly amorphous, which means that the compounds have excellent thermal stability during continuous operation. In other words, a stable amorphous film can be maintained even during device operation, making it possible to provide an organic light-emitting device with a long life.

[0041] Therefore, it is preferable that the Ar group is bonded to the naphthalene ring at a substitution position that causes steric hindrance between the naphthalene ring and the Ar group. In this case, the Ar group is preferably a fused ring, more preferably a fused ring in which three or more 5- or 6-membered rings are fused, and even more preferably a fused ring in which four or more 5- or 6-membered rings are fused.

[0042] (2) It has a low symmetry structure consisting of a phenanthrothiophene ring, a naphthalene ring, and an Ar group. The organic compound of this embodiment has a low symmetry structure consisting of a phenanthrothiophene ring, a naphthalene ring, and an Ar group. For example, if the phenanthrothiophene ring, the naphthalene ring, and the Ar group are each composed of fused rings with different structures, a high molecular weight and low symmetry structure can be designed. Adopting such a molecular structure has the following effects.

[0043] First, the phenanthrothiophene ring, naphthalene ring, and Ar group adopt a conformation that disrupts planarity, thereby suppressing molecular stacking, which inhibits crystallization when a vapor-deposited film is formed, resulting in high amorphousness. High amorphousness, i.e., good filmability, facilitates maintaining an amorphous state without crystallization, making it preferable for use in organic light-emitting devices. This is because high amorphousness reduces the generation of grain boundaries, trap levels, and quenchers associated with microcrystallization, even during device operation, thereby maintaining good carrier transport properties and highly efficient light-emitting characteristics. As a result, organic light-emitting devices with excellent durability and efficiency can be provided.

[0044] Second, the molecular structure has less symmetry, which suppresses the overlapping of molecules, making them less likely to crystallize and more amorphous.

[0045] From the above, it is possible to increase the amorphous property by breaking the symmetry, more preferably by increasing the molecular weight, and therefore it is possible to maintain a stable amorphous film even during device operation, thereby providing an organic light-emitting device with a long life.

[0046] Furthermore, the organic compound of this embodiment can be particularly suitably used in an organic light-emitting device when it further has the following characteristics.

[0047] (3) SP 3 No carbon In the organic compound of this embodiment, the phenanthrothiophene ring and the naphthalene ring serving as the linking group are SP 3 In addition to having no carbon, the Ar group is SP 3 It is preferred that it has no carbon.

[0048] Because SP 3 This is because the carbon-carbon bond of carbon has a small bond energy, and therefore bond cleavage is likely to occur during operation of the organic light-emitting device. In particular, when used as a host material for the light-emitting layer, it is preferable that the skeleton is responsible for charge recombination and exciton generation. In this case, the generation of a certain amount of exciton concentration increases the possibility of being placed in a high-order excited energy state, so it is preferable that the skeleton be resistant to decomposition.

[0049] As shown below, the stability of the bond energy is F1, F2(CN) <F4(SP 3 Carbon-SP 3 carbon) <F3(SP 2 Carbon-SP 2 carbon).

[0050] [ka]

[0051] Therefore, from the viewpoint of improving the durability of the element, 3 It is preferred that it has no carbon.

[0052] Furthermore, when the organic compound of this embodiment further has the following characteristics, it has high hole-blocking ability and electron-trapping ability, and can be particularly suitably used in organic light-emitting devices.

[0053] (4) Has a nitrogen-containing Ar group In developing the organic compound of this embodiment, the inventors focused on an Ar group bonded to a phenanthrothiophene ring via a naphthalene ring. Specifically, the presence of a nitrogen-containing Ar group, i.e., the inclusion of a nitrogen atom as an element constituting the Ar group ring, allows the HOMO level and LUMO level to be adjusted in a deeper direction (away from the vacuum level). Deeper HOMO and LUMO levels are expected to improve oxidation stability and extend lifetime. Furthermore, the deeper HOMO and LUMO levels are expected to be used in hole-blocking layers that require hole-blocking ability. Furthermore, in light-emitting layers that require electron trapping properties, the compound is expected to be used as a second host that complements the electron-trapping ability of the host material.

[0054] Table 2 shows the calculated values ​​of the HOMO and LUMO levels of Example Compound B17, Example Compound B21, and Comparative Compound 1-A.

[0055] [Table 2]

[0056] As shown in Table 2, the HOMO level of Example Compound B17 was -5.26 eV and the LUMO level was -1.80 eV, and the HOMO level of Example Compound B21 was -5.89 eV and the LUMO level was -1.99 eV. On the other hand, the HOMO level of Comparative Compound 1-A was -5.13 eV and the LUMO level was -1.69 eV. From the above, it can be seen that Example Compound B17 and Example Compound B21 exhibit deeper values ​​than Comparative Compound 1-A.

[0057] Therefore, it is important that this organic compound has a nitrogen-containing Ar group in order to use it as a host material for the light-emitting layer or a carrier-blocking layer of an organic light-emitting device. As a result, it is possible to provide device characteristics with high hole-blocking ability and electron-trapping ability, high efficiency, and long life.

[0058] The molecular orbital calculation method used was the density functional theory (DFT), which is currently widely used. The functional was B3LYP, and the basis set was 6-31G. * It is also a smooth-flowing waveguide called Gaussian09(Gaussian09, RevisionC.01,MJFrisch,GWTrucks,HBSchlegel,GEScuse ria, MARobb,JRCheeseman,G.Scalmani,V.Barone,B.Mennucci,GAPetersson,H.Nakatsuji,M.Caricato,X.Li,HPHra tchian, AFIzmaylov, J. Bloino, G. Zheng, JLSonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishi da,T.Nakajima,Y.Honda,O.Kitao,H.Nakai,T.Vreven,JAMontgomery,Jr.,JEPeralta,F.Ogliaro,M.Bearpark,JJHe yd, E. Brothers, KNKudin, VNS Taroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, JCBurant ,SSIyengar,J.Tomasi,M.Cossi,N.Rega,JMMillam,M.Klene,JEKnox,JBCross,V.Bakken,C.Adamo,J.Jaramillo,R.G omperts,REStratmann,O.Yazyev,AJAustin,R.Cammi,C.Pomelli,JWOchterski,RLMartin,K.Morokuma,VGZakrzews ki,GAVoth,P.Salvador,JJDannenberg,S.Dapprich,ADDaniels,O.Farkas,JBForesman,JVOrtiz,JCioslowski,and DJFox,Gaussian,Inc.,Wallingford CT,2010.)

[0059] Furthermore, since the organic compound of this embodiment has a phenanthrothiophene ring, it has the following characteristics: Therefore, it can be particularly suitably used as a host material for an emission layer in an organic light-emitting device.

[0060] (5) Particularly high affinity with pyrene rings In creating the organic compound represented by the general formula [1], the present inventors focused on the phenanthrothiophene ring, which is a partial structure of the compound.

[0061] As shown below, the difference between a phenanthrothiophene ring and a pyrene ring is whether part of the ring structure is a thiophene ring or a benzene ring. It is known that when the atoms constituting such a ring structure contain heteroatoms, the properties usually change significantly.

[0062] [ka]

[0063] Commonly known five-membered heterocyclic compounds include pyrrole rings with nitrogen atoms, furan rings with oxygen atoms, and thiophene rings with sulfur atoms. The resonance energies of five-membered heterocyclic compounds increase in the order furan < pyrrole < thiophene. Thiophene has the greatest aromatic stabilization, similar to that of benzene, while furan retains some butadiene properties. This is due to the electronegativity of the oxygen and nitrogen atoms, which differs from that of carbon atoms. The highly electronegative oxygen and nitrogen atoms create a dipole moment, which increases the likelihood of π electron bias. Therefore, the resonance stabilization energies of five-membered heterocyclic structures are 67.8 kJ / mol for furan rings and 90.4 kJ / mol for pyrrole rings, lower than the 152 kJ / mol for benzene rings. This indicates differences in aromatic stabilization. On the other hand, since the electronegativity of the sulfur atom is the same as that of the carbon atom, the dipole moment is also suppressed, and the resonance stabilization energy is 122 kJ / mol, a value close to that of the benzene ring, and the properties are similar.

[0064] [ka]

[0065] As described above, a thiophene ring having a sulfur atom in the ring structure has properties similar to those of a benzene ring, and it was therefore discovered that the phenanthrothiophene ring and pyrene ring related to the present invention also have similar properties.

[0066] For the reasons described above, the phenanthrothiophene ring and the pyrene ring are thought to have similar electronic properties, resulting in high affinity. Based on this, the present inventors have discovered that by co-depositing a compound having a pyrene ring in its molecule and a compound having a phenanthrothiophene ring as the host material for the light-emitting layer, a stable thin film with high amorphousness and resistance to crystallization can be formed. Even if a compound having a pyrene ring is compatible with a dopant material and exhibits sufficient performance as a host material, but has low film stability due to its amorphous nature, co-depositing a compound having a phenanthrothiophene ring can be expected to have the effect of improving film stability. This is preferable because it allows for the production of an organic light-emitting device that is highly durable and does not crystallize even after long-term operation. When the Ar group of the organic compound of this embodiment is a pyrene ring, the compound is a compound having a pyrene ring in its molecule and a phenanthrothiophene ring, and therefore can be expected to have the same effect as when both are co-deposited.

[0067] As described above, the organic compound of this embodiment has low molecular planarity, breaks down symmetry, and improves amorphousness, and is a compound that is excellent in film properties and sublimation, making it suitable for organic light-emitting devices. Therefore, by using the organic compound of this embodiment as a constituent material of an organic light-emitting device, an organic light-emitting device with good durability can be obtained.

[0068] <Example> Specific examples of the organic compound according to this embodiment are shown below. (A55, A56, and A57 are examples) However, the present invention is not limited to these.

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] The exemplary compounds belonging to Group A are compounds in which the Ar group is a fused polycyclic hydrocarbon group with a hydrogen atom at the peri-position relative to the bond position. These compounds have a steric hindrance between the naphthalene ring and the fused Ar group, resulting in a large dihedral angle, a twisted relationship between the naphthalene ring and the Ar group, and a low planarity of the molecule as a whole. As a result, these compounds are highly amorphous and are expected to have increased film stability during long-term continuous operation, thereby significantly improving drive durability.

[0078] The exemplary compounds in Group B are nitrogen-containing fused polycyclic rings in which the Ar group contains a nitrogen atom as part of the ring structure. These compounds contain a nitrogen atom as part of the six-membered ring structure of the Ar group. Because nitrogen has a higher electronegativity than carbon, Π electrons are attracted to the nitrogen, reducing the electron density of the ring, affecting the electronic properties of the molecule as a whole. For example, the HOMO and LUMO levels are deepened, resulting in properties different from those of the exemplary compounds in Group A. In this case, the deeper HOMO level improves hole-blocking performance, making them suitable for use in hole-blocking layers. Furthermore, the deeper LUMO level enhances electron injection, which, when used as a host material, improves electron injection into the emissive layer. Furthermore, the deeper HOMO level is expected to improve oxidation stability. These characteristics, combined with the elimination of charge imbalance in the emissive layer during long-term continuous operation, make these compounds promising for significantly improved drive durability.

[0079] Exemplary compounds belonging to Group C are compounds in which R1 and R2 have groups other than hydrogen atoms, or the phenanthrothiophene ring has a substituent. In these compounds, the R1 and R2 other than hydrogen atoms, or the substituents on the phenanthrothiophene ring, act as steric hindrance groups, making intermolecular stacking difficult. Therefore, the thin film after film formation is highly amorphous, and the influence of the steric hindrance groups makes intermolecular rearrangement difficult, resulting in compounds with very high sustainability of the amorphous film. Furthermore, because intermolecular stacking is difficult to occur, when used as a host material in the emissive layer, these compounds are expected to reduce the localization of dopant molecules, facilitating their uniform incorporation into the film.

[0080] <Conditions for the light-emitting layer> Furthermore, the compound of this embodiment is preferably used in the light-emitting layer of the organic light-emitting device under the following conditions. (6) The compound of this embodiment is used in an amount of 0.5% by mass or more and 99% by mass or less in the light-emitting layer. (7) In the light-emitting layer, the compound of this embodiment is used as the first host material, and the second host material mixed as the second component is a compound having at least two or more fused rings of either a phenanthrene ring or a pyrene ring within its molecular structure. The above conditions will be explained below.

[0081] (6) The compound of this embodiment is used in an amount of 0.5% by mass or more and 99% by mass or less in the light-emitting layer.

[0082] When the organic compound of this embodiment is used in the light-emitting layer, the content is preferably 0.5% by mass or more and 99% by mass or less. The organic compound of this embodiment is highly amorphous, making it suitable as a host material for the light-emitting layer, and is preferably used in an amount of 50% by mass or more. Even when used in an amount of 99% by mass, it is a material that is difficult to crystallize, and therefore is a compound that exhibits excellent properties.

[0083] In addition, from the viewpoint of improving the film properties of the light-emitting layer, it may be used as an assist material, and when used as an assist material, it can be used in an amount of 0.5% by mass to 50% by mass.

[0084] This is due to the structural characteristics of the organic compound of this embodiment: the compound is less likely to aggregate, and when driving an organic light-emitting device, crystal grain boundaries associated with molecular aggregation are less likely to occur, making it possible to provide a light-emitting device with excellent characteristics.

[0085] (7) In the light-emitting layer, the compound of this embodiment is used as the first host material, and the second host material mixed as the second component is a compound having at least two or more fused rings of either a phenanthrene ring or a pyrene ring within its molecular structure.

[0086] The light-emitting layer may further contain a second component. Specifically, the organic compound of this embodiment may serve as a first host material in the light-emitting layer, and a second host material may be contained as a second component. The second component preferably has a higher (shallower) highest occupied molecular orbital energy (HOMO energy) than the organic compound of this embodiment. Furthermore, the second component is preferably a compound having two or more fused rings of either phenanthrene or pyrene rings in the molecule, preferably two or more pyrene rings. Because the organic compound of this embodiment has low symmetry and high amorphousness, it can be used as a double host material by co-deposition with a material having two or more fused rings of either phenanthrene or pyrene rings, which is highly symmetric and results in low film amorphousness. In this case, the compound of this embodiment is expected to be effective from as little as 0.5% by mass. Even a content of just 0.5% by mass in the film can improve the amorphousness of the highly symmetric second component. The content of the second component relative to the total of the organic compound of this embodiment and the second component is preferably 10% by mass or less.

[0087] <Organic light-emitting element> The organic light-emitting element of this embodiment has a pair of electrodes (a first electrode and a second electrode) and an organic compound layer disposed between the pair of electrodes. When the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may include, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, and the like. The light-emitting layer may be a single layer or a laminate consisting of multiple layers. When multiple light-emitting layers are included, a charge generation layer may be disposed between the light-emitting layers. The charge generation layer is preferably composed of a compound with a low (deep) LUMO level, specifically, a compound with a lower LUMO level than that of the hole transport layer. The charge generation layer is more preferably composed of a compound with a LUMO level lower than that of the hole transport layer.

[0088] In the organic light-emitting device of this embodiment, the organic compound according to this embodiment is contained in at least one organic compound layer, preferably the light-emitting layer, and is preferably contained in the light-emitting layer as a host, an assist, or a guest, preferably as a host or an assist.

[0089] The host is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. The guest is the compound with a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer, and is the compound that is primarily responsible for emitting light. The concentration of the host in the light-emitting layer is preferably 10% by mass or more and 99% by mass or less, more preferably 10% by mass or more and 90% by mass or less, even more preferably 20% by mass or more and 80% by mass or less, and even more preferably 30% by mass or more and 70% by mass or less, based on the total mass of the light-emitting layer. The concentration of the assist is preferably 0.5% by mass or more and 50% by mass or less.

[0090] The guest concentration is 0.01% by mass or more and 50% by mass or less, and preferably 0.1% by mass or more and 20% by mass or less, based on the total amount of the constituent materials of the light-emitting layer. From the viewpoint of reducing concentration quenching, the guest concentration is particularly preferably 10% by mass or less. The guest may be uniformly contained throughout the layer in which the host serves as a matrix, or may be contained with a concentration gradient. Alternatively, the guest may be partially contained in a specific region within the layer, so that the light-emitting layer has a region containing only the host and no guest.

[0091] The light-emitting layer may include a light-emitting material having a lowest unoccupied molecular orbital energy lower (deeper) than the lowest unoccupied molecular orbital energy (LUMO energy) of the organic compound of this embodiment. Such a light-emitting material may have a five-membered ring in its molecular structure. The light-emitting layer may also include a light-emitting material having a highest occupied molecular orbital energy higher (shallower) than the highest occupied molecular orbital energy (HOMO energy) of the organic compound of this embodiment.

[0092] The light-emitting layer may be a single layer or multiple layers, and it is also possible to mix colors by including a light-emitting material having another light-emitting color. Multiple layers means a state in which a light-emitting layer and another light-emitting layer are stacked. In this case, the light-emitting color of the organic light-emitting element is not particularly limited. More specifically, it may be white or an intermediate color. In the case of white, for example, if the light-emitting color of the light-emitting layer is blue, the other light-emitting layer emits a color different from blue, i.e., green or red.

[0093] Furthermore, a third light-emitting layer emitting blue light and a charge-generating layer may be provided between the light-emitting layer or stacked light-emitting layers and the first or second electrode. The charge-generating layer functions as a tandem device, where electrons generated from the charge-generating layer and holes injected from one electrode recombine to generate excitons, and holes generated from the charge-generating layer and electrons injected from the other electrode recombine to form excitons. The charge-generating layer may contain a compound whose lowest unoccupied molecular orbital (LUMO) energy is lower than the highest occupied molecular orbital (HOMO) energy of the light-emitting layer. Therefore, a white light-emitting device can be provided by constructing a tandem device using a stacked light-emitting layer including the light-emitting layer of this embodiment. The third light-emitting layer contains at least a third organic compound and a fourth organic compound. The third organic compound is a host material, and the fourth organic compound is a blue-emitting material.

[0094] Specific examples of the organic light-emitting device of this embodiment include a multilayer device structure in which electrode layers and organic compound layers shown in (a) to (f) below are sequentially stacked on a substrate. In any device structure, the organic compound layers always include a light-emitting layer containing a light-emitting material. (a) Anode / Emitting layer / Cathode (b) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode (c) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (d) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode (e) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (f) Anode / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode However, these examples of device configurations are merely very basic device configurations and are not limited to these. For example, various layer configurations can be adopted, such as providing an insulating layer, an adhesive layer, or an interference layer at the interface between the electrode and the organic compound layer, configuring the electron transport layer or hole transport layer from two layers with different ionization potentials, or configuring the light-emitting layer from two layers made of different light-emitting materials.

[0095] Among the device configurations (a) to (f), the configuration (f) is preferable because it has both an electron blocking layer and a hole blocking layer. In other words, the configuration (f) having an electron blocking layer and a hole blocking layer can reliably confine both hole and electron carriers within the light-emitting layer, resulting in an organic light-emitting device with no carrier leakage and high luminous efficiency.

[0096] The light output from the light-emitting layer can be extracted from the electrode on the substrate side (device configuration), either in a bottom emission mode, where light is extracted from the electrode on the substrate side, or in a top emission mode, where light is extracted from the opposite side of the substrate.A double-sided emission mode, where light is extracted from both the substrate side and the opposite side of the substrate, can also be used.

[0097] The organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer that constitutes the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not particularly limited. More specifically, it may be white or a neutral color.

[0098] <Other compounds> In the organic light-emitting device according to this embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. may be used together as needed. Examples of these compounds are listed below.

[0099] As the hole injection and transport material, a material with high hole mobility is preferred so that holes can be easily injected from the anode and the injected holes can be transported to the light-emitting layer. Furthermore, a material with a high glass transition temperature is preferred to suppress deterioration of film quality, such as crystallization, in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole injection and transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above-mentioned hole injection and transport materials are also suitable for use in electron blocking layers. Specific examples of compounds that can be used as hole injection and transport materials are listed below, but the present invention is not limited to these.

[0100] [ka]

[0101] Examples of light-emitting materials that are primarily involved in light-emitting function include fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Specific examples of compounds that can be used as light-emitting materials are listed below, but the present invention is not limited to these.

[0102] [ka]

[0103] [ka]

[0104] The light-emitting layer host or light-emitting assist material contained in the light-emitting layer may contain a compound other than the organic compound of this embodiment as a second component. Examples of the second component include aromatic hydrocarbon compounds or derivatives thereof, carbazole derivatives, azine derivatives, xanthone derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, and organic beryllium complexes.

[0105] [ka]

[0106] The electron transport material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected taking into consideration the balance with the hole mobility of the hole transport material. Examples of materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transport materials are also suitable for use in hole-blocking layers. Specific examples of compounds used as electron transport materials are shown below, but of course, the present invention is not limited to these.

[0107] [ka]

[0108] 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, etc. Organic compounds include n-type dopants and reducing dopants. Examples include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives. They can also be used in combination with the above electron transport materials.

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

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

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

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

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

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

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

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

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

[0118] The organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, charge generation layer, etc.) constituting the organic light emitting device according to one embodiment of the present invention are formed by the method shown below.

[0119] The organic compound layer constituting the organic light-emitting device according to one embodiment of the present invention can be formed by dry processes such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively to the dry process, a wet process can be used in which the compound is dissolved in an appropriate solvent and a layer is formed by a known coating method (for example, spin coating, dipping, casting, LB method, inkjet method, etc.).

[0120] Here, when a layer is formed by a vacuum deposition method or a solution coating method, crystallization is unlikely to occur and the layer has excellent stability over time. When a film is formed by a coating method, the film can be formed by combining with an appropriate binder resin.

[0121] Examples of the binder resin include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0122] These binder resins may be used singly or in combination as homopolymers or copolymers, and may further contain known additives such as plasticizers, antioxidants, and ultraviolet absorbers, if necessary.

[0123] [Protective layer] A protective layer may be provided on the second electrode. For example, by adhering glass with a moisture absorbent on the second electrode, the infiltration of water and other contaminants into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the second electrode to reduce the infiltration of water and other contaminants into the organic compound layer. For example, after forming the second electrode, the second electrode may be transferred to another chamber without breaking the vacuum, and a 2 μm-thick silicon nitride film may be formed by CVD to serve as a protective layer. A protective layer may be provided using atomic layer deposition (ALD) after the CVD film formation. The material of the film formed by ALD is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed on the film formed by ALD by CVD. The film formed by ALD may have a thickness smaller than that of the film formed by CVD. Specifically, the thickness may be 50% or less, or even 10% or less.

[0124] [Color Filter] A color filter may be provided on the protective layer. For example, a color filter taking into consideration the size of the organic light-emitting element may be provided on a separate substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using photolithography technology. The color filter may be made of a polymer.

[0125] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing the unevenness of the underlying layer. It may also be called a material resin layer without limiting its purpose. The planarization layer may be composed of an organic compound, and may be either a low molecular weight or a high molecular weight, but a high molecular weight is preferred.

[0126] The planarizing layer may be provided above or below the color filter, and may be made of the same or different materials, such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0127] [Microlens] The organic light-emitting element or organic light-emitting device may have an optical component such as a microlens on its light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be intended to increase the amount of light extracted from the organic light-emitting element or organic light-emitting device or to control the direction of the extracted light. 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 vertex of the microlens is the point of contact between this tangent and the hemisphere. The vertex of the microlens can be determined in the same way in any cross-sectional view. In other words, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the vertex of the microlens is the point of contact between this tangent and the semicircle.

[0128] It is also possible to define the midpoint of a microlens. In the cross section of the microlens, a line segment is imagined from the point where an arc shape ends to the point where another arc shape ends, and the midpoint of this line segment can be called the midpoint of the microlens. The cross section for determining the vertex and midpoint may be a cross section perpendicular to the insulating layer.

[0129] [Counter substrate] An opposing substrate may be provided on the planarization layer. The opposing substrate is called an opposing substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the opposing substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is defined as a first substrate, the opposing substrate may be a second substrate.

[0130] [Pixel circuit] An organic light-emitting device having an organic light-emitting element may have a pixel circuit connected to the organic light-emitting element. The pixel circuit may be an active matrix type that controls the emission of the first light-emitting element and the second light-emitting element independently. The active matrix type circuit may be voltage-programmed or current-programmed. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission brightness of the light-emitting element, a transistor that controls the emission timing, a capacitor that holds the gate voltage of the transistor that controls the emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0131] The light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of a transistor constituting the pixel circuit may be smaller than the mobility of a transistor constituting the display control circuit. The slope of the current-voltage characteristics of the transistor constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistor constituting the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics. The transistor constituting the pixel circuit is a transistor connected to a light-emitting element, such as a first light-emitting element.

[0132] [Pixels] An organic light emitting device having an organic light emitting element may have a plurality of pixels, each of which has sub-pixels that emit different colors, for example, RGB colors.

[0133] A pixel emits light from an area called a 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, more specifically, it may be 8 μm, 7.4 μm, or 6.4 μm.

[0134] The pixels may be arranged in a known manner in a plan view. For example, they may be in a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in a plan view may be any known shape. For example, they may be rectangular, quadrilaterals such as diamonds, or hexagons. Of course, a shape that is close to a rectangle, rather than an exact shape, is included in the rectangle. The shape of the subpixels and the pixel arrangement may be used in combination.

[0135] <Applications of organic light-emitting devices> The organic light-emitting device according to this embodiment can be used as a component of a display device or a lighting device, and can also be used as an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, or a light-emitting device having a white light source and a color filter.

[0136] The display device may be an image information processing device having an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., an information processing unit that processes the input information, and displays the input image on a display unit. The display device may have a plurality of pixels, at least one of which may have the organic light-emitting element of this embodiment and a transistor connected to the organic light-emitting element. In this case, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate.

[0137] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of this touch panel function may be an infrared method, a capacitance method, a resistive film method, or an electromagnetic induction method, and is not particularly limited. The display device may also be used in the display unit of a multifunction printer.

[0138] Next, a display device according to this embodiment will be described with reference to the drawings. Fig. 1 is a cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin-film transistor (TFT).

[0139] FIG. 1(a) shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel includes sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on the light emitted from the sub-pixels. The emitted colors may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the sub-pixels may be selectively transmitted or color-converted using a color filter or the like. Each sub-pixel 10 includes a reflective electrode serving as a first electrode 2 on an interlayer insulating layer 1, an insulating layer 3 covering the edges of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode serving as a second electrode 5, a protective layer 6, and a color filter 7.

[0140] A transistor and a capacitor element may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode 2 may be electrically connected via a contact hole or the like (not shown).

[0141] The insulating layer 3 is also called a bank or a pixel separation film. It covers the edges of the first electrode 2 and is disposed to surround the first electrode 2. The portion where the insulating layer 3 is not disposed is in contact with the organic compound layer 4 and becomes a light-emitting region.

[0142] The organic compound layer 4 includes a hole injection layer 41 , a hole transport layer 42 , a first light-emitting layer 43 , a second light-emitting layer 44 , and an electron transport layer 45 .

[0143] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0144] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 is illustrated as being one layer, it may be multiple layers, and each layer may be an inorganic compound layer and an organic compound layer.

[0145] The color filters 7 are divided into 7R, 7G, and 7B depending on their colors. The color filters 7 may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters 7. The color filters 7 may be formed on a protective layer 6. Alternatively, the color filters 7 may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0146] The display device 100 in FIG. 1(b) has an organic light-emitting element 26 and a TFT 18, which is an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided with an insulating layer 12 on top of it. An active element such as the TFT 18 is disposed on the insulating layer 12, and a gate electrode 13 of the active element, a gate insulating film 14, and a semiconductor layer 15 are provided. The TFT 18 has a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on top of the TFT 18. An anode 21 constituting the organic light-emitting element 26 is connected to the source electrode 17 via a contact hole 20.

[0147] The electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the embodiment shown in Fig. 1(b). In other words, it is sufficient that either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT 18.

[0148] 1(b), the organic compound layer 22 is illustrated as a single layer, but may be a multi-layer organic compound layer 22. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26.

[0149] In the display device 100 of FIG. 1(b), transistors are used as switching elements, but other switching elements such as MIM elements may be used instead.

[0150] The transistors used in the display device 100 of Fig. 1(b) are not limited to thin-film transistors having an active layer on an insulating surface of a substrate, but may also be transistors using a single-crystal silicon wafer. Examples of active layers include single-crystal silicon, amorphous silicon, microcrystalline silicon, and other non-single-crystal silicon, as well as non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0151] The transistors included in the display device 100 of Fig. 1(b) may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the substrate itself, such as a Si substrate, is processed to form the transistors. In other words, having a transistor within a substrate can be seen as the substrate and the transistor being integrally formed.

[0152] The organic light-emitting element according to this embodiment has its emission brightness controlled by a TFT, which is an example of a switching element. By providing multiple organic light-emitting elements on a surface, an image can be displayed based on the emission brightness of each element. 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 referred to as "inside the substrate." Whether to provide a transistor in the substrate or to use a TFT is determined by the size of the display unit. For example, for a display size of about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0153] 2 is a schematic diagram illustrating an example of a display device according to this embodiment. The display device 1000 may include a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The touch panel 1003 and the display panel 1005 are connected by flexible printed circuits FPCs 1002 and 1004. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position even if the display device is a portable device.

[0154] The display device according to this embodiment may have color filters having red, green, and blue colors, which may be arranged in a delta arrangement.

[0155] The display device according to the present embodiment may be used as a display unit of a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include a mobile phone such as a smartphone, a tablet, and a head-mounted display.

[0156] The display device according to this embodiment may be used as a display unit of an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0157] 3A is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may include a display device according to this embodiment. In this case, the display device may display not only an image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject is moving, the possibility that the subject will be blocked by an obstruction, and the like.

[0158] Since the optimum timing for capturing an image is very short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment. This is because the organic light-emitting element has a fast response speed. A display device using the organic light-emitting element can be used more preferably than a liquid crystal display device, which requires a high display speed.

[0159] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses, which form an image on an imaging element housed in a housing 1104. The focus of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may also be called a photoelectric conversion device. Instead of sequentially capturing images, the photoelectric conversion device can include an imaging method that detects the difference from the previous image, or a method of cutting out an image from a constantly recorded image, etc.

[0160] FIG. 3(b) is a schematic diagram illustrating an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit 1202 may be a biometric recognition unit that recognizes a fingerprint to perform operations such as unlocking. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an image sensor. An image captured by the camera function is displayed on the display unit 1201. Examples of the electronic device 1200 include a smartphone and a laptop computer.

[0161] FIG. 4 is a schematic diagram illustrating an example of a display device according to this embodiment. FIG. 4(a) illustrates a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The display unit 1302 may use a light-emitting element according to this embodiment. The display device 1300 has the frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. 4(a). The lower side of the frame 1301 may also serve as the base. The frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0162] FIG. 4(b) is a schematic diagram illustrating another example of a display device according to this embodiment. The display device 1310 in FIG. 4(b) is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include light-emitting elements according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single, seamless display unit. The first display unit 1311 and the second display unit 1312 can be separated by the bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may display a single image.

[0163] FIG. 5(a) is a schematic diagram illustrating an example of a lighting device according to this embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusion unit 1405. The light source 1402 may include an organic light-emitting element according to this embodiment. The optical filter 1404 may be a filter that improves the color rendering of the light source. The light diffusion unit 1405 can effectively diffuse light from the light source, such as for illumination, and deliver the light over a wide area. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the lighting device. If necessary, a cover may be provided on the outermost surface.

[0164] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white, daylight white, or any other color from blue to red. It may have a dimming circuit for dimming them or a color tuning circuit for tuning the emitted color. The lighting device may have the organic light-emitting element of this embodiment and a power supply circuit connected to it. The power supply circuit is a circuit that converts AC voltage to DC voltage. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device may have a color filter.

[0165] The lighting device according to this embodiment may also include a heat dissipation unit, which dissipates heat from within the device to the outside, and may be made of a material such as a metal with a high specific heat capacity or liquid silicon.

[0166] 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 lighting fixtures. The automobile 1500 has tail lamps 1501, and may be configured to turn on the tail lamps when braking or the like is performed.

[0167] The tail lamp 1501 may include an organic light-emitting element according to this embodiment. The tail lamp 1501 may include a protective member for protecting the organic light-emitting element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0168] The automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display as long as it is not a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials of the electrodes and the like of the organic light-emitting element are made of transparent materials.

[0169] The moving body according to this embodiment may be a ship, an aircraft, a drone, or the like. The moving body may have a body and a lighting device provided on the body. The lighting device may emit light to indicate the position of the body. The lighting device has the organic light-emitting element according to this embodiment.

[0170] An application example of the display device of each of the above-described embodiments will be described with reference to Fig. 6. The display device can be applied to a system that can be attached as a wearable device, such as smart glasses, an HMD, or a smart contact lens. An image capturing and displaying device used in such an application example includes an image capturing device capable of photoelectrically converting visible light and a displaying device capable of emitting visible light.

[0171] Fig. 6(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using Fig. 6(a), glasses 1600 (smart glasses) according to one application example will be described. An imaging device 1602 such as a CMOS sensor or SPAD is provided on the front side of a lens 1601 of the glasses 1600. In addition, a display device according to each of the above-mentioned embodiments is provided on the back side of the lens 1601.

[0172] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the image capture device 1602 and the display device. The control device 1603 also controls the operations of the image capture device 1602 and the display device. The lens 1601 is formed with an optical system for focusing light onto the image capture device 1602.

[0173] FIG. 6(b) is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 6(b), glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 have a control device 1612, which is equipped with an imaging device corresponding to the imaging device 1602 in FIG. 6(a) and a display device. A lens 1611 is formed with an optical system for projecting light emitted from the imaging device in the control device 1612 and the display device, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and also controls the operation of the imaging device and the display device.

[0174] The control device 1612 may include a gaze detection unit that detects the wearer's gaze. The gaze detection may use infrared light. The infrared light emitter emits infrared light toward the eyeball of the user gazing at the display image. An imaging unit with a light-receiving element detects the reflected infrared light from the eyeball, thereby obtaining a captured image of the eyeball. A reduction unit that reduces light from the infrared light emitter to the display unit in a planar view reduces degradation of image quality. The user's gaze toward the displayed image is detected from the captured image of the eyeball obtained by capturing infrared light. Any known method can be applied to gaze detection using the captured image of the eyeball. As an example, a gaze detection method based on a Purkinje image formed by reflection of irradiated light on the cornea can be used. More specifically, gaze detection processing based on the pupil-corneal reflex method is performed. Using the pupil-corneal reflex method, a gaze vector representing the orientation (rotation angle) of the eyeball is calculated based on the image of the pupil and the Purkinje image included in the captured image of the eyeball, thereby detecting the user's gaze.

[0175] A display device according to one embodiment of the present invention may include an imaging device having a light receiving element, and may control the display image of the display device based on user line-of-sight information from the imaging device. Specifically, the display device determines a first field of view area where the user gazes and a second field of view area other than the first field of view area based on the line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. In the display area of ​​the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than that of the first field of view area.

[0176] The display area includes a first display area and a second display area different from the first display area, and a high-priority area is determined from the first display area and the second display area based on line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. The resolution of the high-priority area may be controlled to be higher than the resolution of areas other than the high-priority area. In other words, the resolution of an area with a relatively low priority may be lowered.

[0177] Note that AI may be used to determine the first field of view area and areas with high priority. The AI ​​may be a model configured to estimate the angle of gaze and the distance to an object in the line of sight from an image of the eyeball, using as training data an image of the eyeball and the direction in which the eyeball in the image was actually looking. The AI ​​program may be included in the display device, the imaging device, or an external device. If included in an external device, it is transmitted to the display device via communication.

[0178] When display control is performed based on visual recognition detection, the smart glasses can be preferably applied to smart glasses that further include an imaging device for capturing images of the outside world. The smart glasses can display captured external information in real time.

[0179] 7(a) is a schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 includes the organic light-emitting element according to this embodiment. The developing unit 31 includes toner and the like. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0180] 7(b) and 7(c) are diagrams showing an exposure light source 28 and are schematic diagrams illustrating a state in which multiple light-emitting units 36 are arranged on a long substrate. Arrow 37 indicates the direction parallel to the axis of the photoconductor, the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the axis direction about which the photoconductor 27 rotates. This direction can also be referred to as the long axis direction of the photoconductor 27. FIG. 7(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoconductor 27. FIG. 7(c) shows a configuration different from FIG. 7(b), in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are arranged at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged at intervals. In the second column, light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. In other words, multiple light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in FIG. 7(c) can also be described as a grid arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0181] As described above, by using a device using the organic light-emitting element according to this embodiment, it is possible to provide a stable display with good image quality even over a long period of time.

[0182] ≪Included components≫ The disclosure of this embodiment includes the following configuration. (Configuration 1) An organic compound represented by the above general formula [1]. (Configuration 2) 2. The organic compound according to claim 1, wherein Ar is a fused ring. (Configuration 3) 3. The organic compound according to claim 2, wherein Ar is a fused ring in which three or more five-membered or six-membered rings are fused together. (Configuration 4) The organic compound according to the third aspect of the present invention is characterized in that Ar is selected from the above [a] to [n]. (Configuration 5) The organic compound according to structure 4, wherein the Ar is selected from the groups [a] to [f].

[0183] (Configuration 6) a first electrode and a second electrode; an organic compound layer disposed between the first electrode and the second electrode, 6. An organic light-emitting device, wherein at least one of the organic compound layers contains the organic compound according to any one of Structures 1 to 5. (Configuration 7) 7. The organic light-emitting device according to configuration 6, wherein the layer containing the organic compound is a light-emitting layer. (Configuration 8) 8. The organic light-emitting device according to claim 7, wherein the light-emitting layer further comprises a light-emitting material having a lowest unoccupied molecular orbital energy lower than that of the organic compound. (Configuration 9) 9. The organic light-emitting device according to configuration 8, wherein the light-emitting material has a five-membered ring in its molecular structure. (Configuration 10) 8. The organic light-emitting device according to configuration 7, wherein the light-emitting layer further contains a light-emitting material having a highest occupied molecular orbital energy higher than that of the organic compound.

[0184] (Configuration 11) 8. The organic light-emitting device according to claim 7, wherein the light-emitting layer further comprises a second component. (Configuration 12) 12. The organic light-emitting device according to claim 11, wherein the second component has a highest occupied molecular orbital energy higher than that of the organic compound. (Configuration 13) 13. The organic light-emitting device according to claim 11, wherein the second component has two or more fused rings of either a phenanthrene ring or a pyrene ring in the molecule. (Configuration 14) 14. The organic light-emitting device according to any one of configurations 11 to 13, wherein the content of the second component relative to the total of the organic compound and the second component is 10% by mass or less. (Configuration 15) 15. The organic light-emitting element according to any one of Structures 7 to 14, further comprising another light-emitting layer disposed in a stacked state with the light-emitting layer, the another light-emitting layer emitting light of a color different from the color of light emitted by the light-emitting layer.

[0185] (Configuration 16) A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to any one of structures 6 to 15 and a transistor connected to the organic light-emitting element. (Configuration 17) an optical unit having a plurality of lenses, an image pickup element that receives light that has passed through the optical unit, and a display unit that displays an image picked up by the image pickup element; 16. A photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to any one of configurations 6 to 15. (Configuration 18) 16. An electronic device comprising: a display unit having the organic light-emitting element according to any one of configurations 6 to 15; a housing in which the display unit is provided; and a communication unit provided in the housing and communicating with an external device. (Configuration 19) 16. A lighting device comprising: a light source having the organic light-emitting element according to any one of configurations 6 to 15; and a light diffusion section or an optical filter that transmits light emitted by the light source. (Configuration 20) A moving body comprising: a lighting fixture having the organic light-emitting element according to any one of configurations 6 to 15; and a vehicle on which the lighting fixture is provided. (Configuration 21) 16. An exposure light source for an electrophotographic image forming apparatus, comprising the organic light-emitting element according to any one of Configurations 6 to 15. [Example]

[0186] The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

[0187] Example 1 (Synthesis of Exemplary Compound A3) [ka]

[0188] (1) Synthesis of compound m-2 The following reagents and solvents were placed in a 500 ml recovery flask. Compound m-1: 8.2g (0.032mol) Hexane: 160ml Next, the reaction solution was stirred at -30°C under a nitrogen atmosphere, and TMEDA (24 ml, 0.16 mol) and n-BuLi (1.6 M, 100 ml, 0.16 mol) were added via a dropping funnel. After stirring for 3 hours under a nitrogen atmosphere, S2Cl2 (6.4 ml, 0.08 mol) was slowly added and the reaction was allowed to proceed at room temperature for 24 hours. The reaction mixture was partitioned between water and chloroform and then purified by silica gel column chromatography (eluent: heptane / chloroform) to obtain 5.0 g of compound m-2 (yield: 55%).

[0189] (2) Synthesis of compound m-3 The following reagents and solvents were placed in a 300 ml recovery flask. Compound m-2: 2.5g (8.7mmol) Bispinacolatoborane: 2.3g (8.7mmol) [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct: 0.57g (0.71mmol) Potassium acetate: 2.3 g (22.6 mmol) 1,4-dioxane: 90 ml The reaction solution was heated under reflux for 5 hours under nitrogen with stirring. After the reaction was completed, the solvent was distilled off under reduced pressure, and the resulting solid was purified using a silica gel column (chloroform:heptane=2:1) ​​to obtain 2.0 g of m-3 (yield 70%).

[0190] (3) Synthesis of compound m-5 The following reagents and solvents were placed in a 300 ml recovery flask. Compound m-3: 1.5g (4.5mmol) Compound m-4: 1.3g (4.5mmol) Pd(PPh3)4: 0.26 g (0.22 mmol) Toluene: 45 ml Ethanol: 23ml 2M sodium carbonate solution: 23 ml The reaction solution was then heated under reflux under a nitrogen atmosphere for 6 hours. After the reaction was completed, water and toluene were added and the mixture was separated. The mixture was purified by column chromatography (toluene:heptane) and recrystallized from toluene to obtain 1.5 g (yield: 80%) of compound m-5 as a white solid.

[0191] (4) Synthesis of Example Compound A3 The following reagents and solvents were placed in a 300 ml recovery flask. Compound m-5: 1.0g (2.4mmol) Compound m-6: 1.3g (2.4mmol) Pd(PPh3)4: 0.14 g (0.12 mmol) Toluene: 30 ml Ethanol: 15ml 2M sodium carbonate solution: 15 ml The reaction solution was then heated under reflux under a nitrogen atmosphere for 6 hours. After the reaction was completed, water and toluene were added and the mixture was separated. The mixture was purified by column chromatography (toluene:heptane) and recrystallized from toluene to obtain 1.1 g (yield: 90%) of compound A3 as a white solid.

[0192] The exemplary compound A3 was subjected to mass spectrometry using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker). [MALDI-TOF-MS] Measured value: m / z=510 Calculated value: C 38 H 22 S=510

[0193] [Examples 2 to 30 (Synthesis of Exemplary Compounds)] Exemplary compounds were synthesized in the same manner as in Example 1, except that raw materials m-1, m-4, and m-6 were changed as shown in Tables 3 to 6. The actual measured values ​​(m / z) of the mass spectrometry results measured in the same manner as in Example 1 are also shown.

[0194] [Table 3]

[0195] [Table 4]

[0196] [Table 5]

[0197] [Table 6]

[0198] [Example 31] An organic light-emitting device with a bottom emission structure was fabricated by sequentially forming an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode on a substrate.

[0199] First, an ITO film was formed on a glass substrate and then patterned as desired to form an ITO electrode (anode). At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed was used as the ITO substrate in the following process. Next, a 1.33 × 10 -4 The organic compound layer and electrode layer shown in Table 7 were successively formed on the ITO substrate by vacuum deposition using resistance heating in a vacuum chamber at 1000 Pa. At this time, the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was 3 mm 2 It was made to be like this.

[0200] [Table 7]

[0201] The characteristics of the obtained device were measured and evaluated. The light-emitting device emitted a good blue light. The maximum external quantum efficiency (EQE) was 1.3, where Comparative Example 1 was taken as 1.0. Furthermore, at a current density of 100 mA / cm 2 A continuous driving test was carried out at 100°C, and the time when the luminance degradation rate reached 5% was measured. When the time when the luminance degradation rate of Comparative Example 1 reached 5% was set to 1.0, the luminance degradation rate ratio of this example was 1.4.

[0202] In this example, the measuring device was specifically a microcurrent meter 4140B manufactured by Hewlett-Packard Company to measure the current-voltage characteristics, and a BM7 manufactured by Topcon Corporation to measure the luminance.

[0203] [Examples 32 to 40, Comparative Example 1] An organic light-emitting device was produced in the same manner as in Example 31, except for appropriately changing the compounds shown in Table 8. The host material used in Comparative Example 1 was Compound 1-A described in Patent Document 1. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 31. The measurement results are shown in Table 8.

[0204] [Table 8]

[0205] As can be seen from Table 8, the maximum external quantum efficiency (EQE) of each example exceeded 1.0 compared to the maximum external quantum efficiency (EQE) of Comparative Example 1, and the light-emitting devices of the examples had higher luminous efficiency. Furthermore, the light-emitting devices of the examples had a longer life. This is because the organic compound of this embodiment has excellent film properties and sublimation properties, and is therefore excellent in long-term driving durability.

[0206] [Examples 41 to 49, Comparative Example 2] An organic light-emitting device was produced in the same manner as in Example 31, except that the guest material was changed to GD6 and appropriately changed to the compounds shown in Table 9. The host material used in Comparative Example 2 was Compound 1-A described in Patent Document 1. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 31. The measurement results are shown in Table 9.

[0207] The light-emitting device emitted a good green light. The maximum external quantum efficiency (EQE) is shown relative to the value of Comparative Example 2, which is set to 1.0. The luminance degradation rate ratio is shown relative to the time when the luminance degradation rate of Comparative Example 2 reached 5%, which is set to 1.0.

[0208] [Table 9]

[0209] As can be seen from Table 9, the maximum external quantum efficiency (EQE) of each example exceeded 1.0 compared to the maximum external quantum efficiency (EQE) of Comparative Example 2, and the optical elements of the examples had higher luminous efficiency. Furthermore, the light-emitting elements of the examples had a longer life. This is because the organic compound of this embodiment has excellent film-forming properties and sublimation properties, resulting in good long-term driving durability.

[0210] [Examples 50 to 52, Comparative Example 3] An organic light-emitting device was produced in the same manner as in Example 31, except that the guest material was changed to RD1 and appropriately replaced with the compounds shown in Table 10. The host material used in Comparative Example 3 was Compound 1-A described in Patent Document 1. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 31. The measurement results are shown in Table 10.

[0211] The light-emitting device emitted a good red light. The maximum external quantum efficiency (EQE) is shown relative to the value of Comparative Example 3, which is set to 1.0. The luminance degradation rate ratio is shown relative to the time when the luminance degradation rate of Comparative Example 3 reached 5%, which is set to 1.0.

[0212] [Table 10]

[0213] As can be seen from Table 10, the maximum external quantum efficiency (EQE) of each example exceeded 1.0 compared to the maximum external quantum efficiency (EQE) of Comparative Example 3, and the light-emitting devices of the examples had higher luminous efficiency. Furthermore, the light-emitting devices of the examples had a longer life. This is because the organic compound of this embodiment has excellent film properties and sublimation properties, and is therefore excellent in long-term driving durability.

[0214] [Example 53] An organic light-emitting device was produced in the same manner as in Example 31, except that the organic compound layer and the electrode layer shown in Table 11 were successively formed.

[0215] [Table 11]

[0216] The characteristics of the obtained element were measured and evaluated in the same manner as in Example 31. The light-emitting element emitted white light, and the luminance degradation rate ratio was 1.8, where the time when the luminance degradation rate in Comparative Example 4 reached 5% was taken as 1.0.

[0217] [Examples 54 to 70] Organic light-emitting devices were produced in the same manner as in Example 53, except that the compounds (upper row) and mass ratios (lower row) were appropriately changed as shown in Tables 12 and 13. The characteristics of the obtained devices were measured and evaluated in the same manner as in Example 53. The measurement results are shown in Tables 12 and 13.

[0218] [Table 12]

[0219] [Table 13] [Explanation of symbols]

[0220] 1: interlayer insulating layer, 2: first electrode, 3: insulating layer, 4: organic compound layer, 5: second electrode, 6: protective layer, 7: color filter, 10: subpixel, 11: substrate, 12: insulating layer, 13: gate electrode, 14: gate insulating film, 15: semiconductor layer, 16: drain electrode, 17: source electrode, 18: TFT, 19: insulating film, 20: contact hole, 21: anode, 22: organic compound layer, 23: cathode, 24: first protective layer, 25: second protective layer, 26: organic light-emitting element, 100: display device< / ar>

Claims

1. An organic compound represented by the following general formula [1]: 【Chemical Formula 1】 In the general formula [1], Ar is selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group. R 1 ~R 2 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. m and n are 1. The aryl group and heteroaryl group represented by Ar are selected from the substituted or unsubstituted groups represented by [a] to [n] below. 【Chemistry 2】 In the above [a] to [n], * indicates the bonding position to the naphthalene ring.

2. 2. The organic compound according to claim 1, wherein the aryl group and the heteroaryl group represented by Ar are selected from the substituted or unsubstituted groups represented by [a] to [f].

3. a first electrode and a second electrode; an organic compound layer disposed between the first electrode and the second electrode, An organic light-emitting device, wherein at least one of the organic compound layers contains the organic compound according to claim 1 or 2.

4. 4. The organic light-emitting device according to claim 3, wherein the layer containing the organic compound is a light-emitting layer.

5. The organic light-emitting device according to claim 4 , wherein the light-emitting layer further comprises a light-emitting material having a lowest unoccupied molecular orbital energy lower than that of the organic compound.

6. The organic light-emitting element according to claim 5 , wherein the light-emitting material has a five-membered ring in its molecular structure.

7. The organic light-emitting device according to claim 4 , wherein the light-emitting layer further contains a light-emitting material having a highest occupied molecular orbital energy higher than that of the organic compound.

8. The organic light-emitting device according to claim 4 , wherein the light-emitting layer further comprises a second component.

9. The organic light-emitting device according to claim 8 , wherein the second component has a highest occupied molecular orbital energy higher than that of the organic compound.

10. The organic light-emitting element according to claim 8, wherein the second component has two or more fused rings of either a phenanthrene ring or a pyrene ring in the molecule.

11. 9. The organic light-emitting element according to claim 8, wherein the content of the second component relative to the total of the organic compound and the second component is 10% by mass or less.

12. 5. The organic light-emitting element according to claim 4, further comprising another light-emitting layer disposed in a stacked state with the light-emitting layer, the another light-emitting layer emitting light of a color different from the color of light emitted by the light-emitting layer.

13. 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 3 and a transistor connected to the organic light-emitting element.

14. an optical unit having a plurality of lenses, an image pickup element that receives light that has passed through the optical unit, and a display unit that displays an image picked up by the image pickup element; The photoelectric conversion device according to claim 3, wherein the display section comprises the organic light-emitting element according to claim 3.

15. An electronic device comprising: a display unit having the organic light-emitting element according to claim 3; a housing in which the display unit is provided; and a communication unit provided in the housing for communicating with an external device.

16. 4. A lighting device comprising: a light source having the organic light-emitting element according to claim 3; and a light diffusion section or an optical filter that transmits light emitted by the light source.

17. A moving body comprising: a lamp having the organic light-emitting element according to claim 3; and a body on which the lamp is provided.

18. An exposure light source for an electrophotographic image forming apparatus, comprising the organic light emitting device according to claim 3 .

Images