Organic compound and organic light-emitting device

Abstract

To provide an organic compound having a large reverse intersystem crossing rate constant (kRISC).SOLUTION: The organic compound is represented by general formula (1). In the formula (1), ring a to ring c are each independently selected from an aryl ring and the like. X is a sulfur atom or the like. R1 to R3 are each independently selected from hydrogen atoms, alkyl groups, and the like. However, at least two of R1 to R3 are each independently selected from groups represented by the formula (2). In the formula (2), R4 to R11 are each independently selected from hydrogen atoms, alkyl groups, and the like. Adjacent two of R4 to R11 may be bonded to the group represented by the formula (3). In the formula (3), R12 to R15 are each independently selected from hydrogen atoms, alkyl groups, and the like. Y is selected from an oxygen atom and the like; 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 device (hereinafter sometimes referred to as an "organic electroluminescence device" or "organic EL device") is an electronic device having a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. By injecting electrons and holes from this pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic EL device emits light. Delayed fluorescent materials (TADF materials) generally have a structure in which donor and acceptor moieties are bonded (hereinafter referred to as "DA type"). DA type TADF materials undergo reverse intersystem crossing from the excited triplet state to the excited singlet state in the excited state, and then emit fluorescence when returning from the excited singlet state to the ground state. In other words, TADF materials can utilize not only the excited singlet state but also the excited triplet state for fluorescence emission via a pathway mediated by reverse intersystem crossing, resulting in higher luminous efficiency than conventional fluorescent materials. On the other hand, multi-resonance (MR) type TADF materials, known as DABNA, which incorporate boron and nitrogen atoms into a single molecule and utilize the multiple resonance effect, have a narrower half-width than DA types and are highly efficient materials. Since this principle was clarified, various researches have led to the discovery of various TADF materials. Among them, MR-DA type TADF materials are materials that combine the properties of both MR type and DA type, and Patent Document 1 discloses Compound A as an MR-DA type TADF material.

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

[0004] [Patent Document 1] Chinese Patent Application Publication No. 112898322 Summary of the Invention [Problem to be solved by the invention]

[0005] Compound A described in Patent Document 1 has a reverse intersystem crossing rate constant (k RISC ) there is room for improvement. Therefore, the present invention has been made in consideration of the above problems, and an object of the present invention is to provide a method for determining the reverse intersystem crossing rate constant (k RISC Another object of the present invention is to provide an organic EL device, such as an organic light-emitting device, that uses this organic compound and has reduced roll-off characteristics. [Means for solving the problem]

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

[0007] [ka] In general formula (1), rings a to c are each independently selected from substituted or unsubstituted aryl rings and substituted or unsubstituted heteroaryl rings. X is a sulfur atom or a selenium atom. R1 to R3 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group, provided that at least two of R1 to R3 are each independently selected from groups represented by the following general formula (2):

[0008] [ka] In general formula (2), R4 to R 11 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. 11 Any two adjacent ones of these may be bonded to a group represented by the following general formula (3).

[0009] [ka] In general formula (3), R 12 ~R 15 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. Y is selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, and a nitrogen atom substituted with an alkyl group or an aryl group. In general formula (2), * represents the bonding position with general formula (1). In general formula (3), * represents the bonding position with general formula (2). [Effects of the Invention]

[0010] According to the present invention, the reverse intersystem crossing rate constant (k RISC ) can provide organic compounds with large molecular weights. [Brief explanation of the drawings]

[0011] [Figure 1] 1 is a graph showing the relative ST values ​​of the compounds shown in Tables 1 to 6. [Figure 2] 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 3] 1 is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention. [Figure 4] 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 5] 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 6] 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 7] 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 8] 1A is a schematic diagram illustrating an example of an image forming apparatus according to an embodiment of the present invention, and FIGS. 1B and 1C are schematic diagrams illustrating an example of an exposure light source of the image forming apparatus according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0012] In this specification, examples of halogen atoms include, but are not limited to, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0013] The alkyl group may be an alkyl group having from 1 to 20 carbon atoms, or may be an alkyl group having from 1 to 6 carbon atoms. Examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, a pentyl group, a hexyl group, an octyl group, a cyclohexyl group, a tertiary pentyl group, and a 3-methylpentan-3-yl group.

[0014] The aryl group may be an aryl group having from 6 to 20 carbon atoms, or may be an aryl group having from 6 to 18 carbon atoms. Examples of the aryl group include, but are not limited to, a phenyl group and a naphthyl group.

[0015] The heterocyclic group may be a heterocyclic group having 3 to 24 carbon atoms, or a heterocyclic group having 6 to 18 carbon atoms. The heterocyclic group may be a heteroaryl group. Examples of heterocyclic groups include, but are not limited to, a pyridyl group, a carbazolyl group, an acridinyl group, and a phenanthrolyl group.

[0016] Examples of the amino group include, but are not limited to, a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, and a ditolylamino group.

[0017] Examples of alkoxy groups include, but are not limited to, groups in which the above-mentioned alkyl groups are bonded to oxygen.

[0018] Specific examples of the aryloxy group include, but are not limited to, a phenoxy group.

[0019] Specific examples of heteroaryloxy groups include, but are not limited to, thienyloxy groups.

[0020] Examples of aralkyl groups include, but are not limited to, benzyl groups.

[0021] Examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triphenylsilyl group, etc.

[0022] Examples of the substituent that the alkyl group, aryl group, heterocyclic group, amino group, alkoxy group, aryloxy group, heteroaryloxy group, aralkyl group, and silyl group may further have include, but are not limited to, an alkyl group such as a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group; an aralkyl group such as a benzyl group; an aryl group such as a phenyl group, a biphenyl group; a heteroaryl group such as a pyridyl group, a pyrrolyl group, a pyrazolyl group, a triazyl; an amino group such as a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, a ditolylamino group; an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group; an aryloxy group such as a phenoxy group; a deuterium atom, a cyano group, etc.

[0023] (1) Organic compound First, the organic compound according to the present invention will be described. The organic compound according to the present invention is an organic compound represented by the following general formula (1). The isotope species of the hydrogen atoms present in the molecule of the organic compound according to the present invention is not particularly limited. For example, all of the hydrogen atoms in the molecule may be 1 H, or some or all of them may be 2 H (deuterium). The organic compound according to the present invention may be a compound exhibiting delayed fluorescence, and may be a compound exhibiting thermally activated delayed fluorescence (TADF). [[ID=第十八]] [[ID=第十九]]

[0024] [[ID=第二十]] [[ID=第二十一]] [[ID=第二十二]]

Chemical formula

[0025] [[ID=第二十八]] [[ID=第二十九]][[ID=第三十]] [[ID=第三十一]]In the general formula (1), the a ring to the c ring are each independently selected from a substituted or unsubstituted aryl ring and a substituted or unsubstituted heteroaryl ring. [[ID=第三十二]]

[0026] <x> In general formula (1), X is a sulfur atom or a selenium atom. X is preferably a sulfur atom.

[0027] <R1 to R3> In general formula (1), R1 to R3 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. R1 to R3 are preferably each independently selected from a hydrogen atom and a substituted or unsubstituted aryl group. However, at least two of R1 to R3 are each independently selected from the groups represented by the following general formula (2).

[0028] [Chemical formula]

[0029] <R4 to R 11 > In general formula (2), R4 to R 11 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. R4 to R 11 are preferably each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group.

[0030] Two adjacent ones of R4 to R 11 may be bonded to the group represented by the following general formula (3). R4 to R 11 The two adjacent ones of R4 to R7 or R8 to R 11 may be two adjacent ones of R8 to R 11 It is preferable that two of R4 to R7 are adjacent to each other. Specifically, two of R4 to R7 that are adjacent to each other are R4 and R5, R5 and R6, or R6 and R7. 11 Specifically, the two adjacent ones are R8 and R9, and R9 and R 10 , or R 10 and R 11 Among these, it is preferable that R8 and R9 bond to the group represented by general formula (3).

[0031] [ka]

[0032] <R 12 ~R 15 > In general formula (3), R 12 ~R 15 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. 12 ~R 15 are preferably each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group.

[0033] <y> In general formula (3), Y is selected from an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, a nitrogen atom substituted with an alkyl group or an aryl group. Y is preferably selected from an oxygen atom and a nitrogen atom substituted with an aryl group.

[0034] <*> In general formula (2), * represents the bonding position with general formula (1). In general formula (3), * represents the bonding position with general formula (2).

[0035] The compound of the present invention is preferably represented by the following general formula (4).

[0036]

Chemical formula

[0037] <Y1 to Y7> In general formula (4), Y1 to Y7 are each independently selected from a carbon atom and a nitrogen atom. Y1 to Y7 are preferably carbon atoms, and more preferably all carbon atoms. When Y1 to Y7 are carbon atoms, they are bonded to R 16 to R 22 and are bonded.

[0038] <R 16 to R 26 > In general formula (4), R 16 to R 26 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. R 16 to R 26 are preferably each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. Since ring a and ring b are aryl rings or heteroaryl rings, R 16 ~R 22 is bonded to Y1 to Y7 when Y1 to Y7 are carbon atoms, but is not bonded to Y1 to Y7 when Y1 to Y7 are nitrogen atoms.

[0039] Substituents that may be possessed by rings a to c, R to R 15 , R1 to R 15 From the viewpoint of sublimability, at least one of the substituents that may be possessed by the compound is preferably selected from a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, a substituted or unsubstituted heterocyclic group having from 6 to 18 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, and a cyano group.

[0040] Substituents that may be possessed by rings a to c, R to R 15 , R1 to R 15 At least one of the substituents which may be possessed by is preferably selected from Group A below.

[0041] [ka]

[0042] <Structural characteristics of the compound> The organic compound represented by the general formula (1) has the following characteristics. (1) By introducing a large number of donor units into MR-type TADF materials, the reverse intersystem crossing rate is fast and the roll-off characteristics are effectively reduced.

[0043] TADF materials undergo reverse intersystem crossing from the excited triplet state to the excited singlet state in an excited state, and then emit fluorescence when returning from the excited singlet state to the ground state. The rate constant of this reverse intersystem crossing (k RISC ) is known to be expressed by the following formula (1).

[0044]

number

[0045] Here, H bar, k B is a constant, λ (Marcus reorganization energy) does not vary significantly among compounds, and the temperature T is constant. Assuming this, k RISC is substituted by the following equation (2), so k RISC The ST value will be used as an indicator in the following discussion.

[0046]

number

[0047] If the ST value is large, k RISC In addition, when considering intersystem crossing via higher-order triplets, the ST is calculated by considering not only the intersystem crossing between the lowest-level singlet S1 and the lowest-level triplet T1, but also the intersystem crossing between S1 and T2, S1 and T3, and S1 and T4. The ΔE ST The SOC was calculated as follows:

[0048] (Calculation method) ΔE between each level ST The density functional method with the functional PBE1PBE and the basis set 6-31g* was used to perform a geometry optimization calculation to find the most stable structure of the ground state S0. The time-dependent density functional method with the functional and basis set described above was used to calculate the excitation energy E from S0 to S1 for the most stable structure of S0. S1 , the excitation energy E from S0 to T1 T1 , the excitation energy E from S0 to T2 T2 , the excitation energy E from S0 to T3 T3 , the excitation energy E from S0 to T4 T4 Calculate ΔE for T1 ST is E S1 -E T1 , ΔE for T2 ST is E S1 -E T2 , ΔE for T3 ST is E S1 -E T3 , ΔE for T4 ST is E S1 -E T4 It can be calculated by:

[0049] Determination of the thermodynamic range and the gaussian 16th Revision C.01(Gaussian 16、Revision C.01, MJFrisch, GWTrucks, HBSchlegel, GEScuseria, MARobb, JRCheeseman, G. Scalmani, V. Barone, GAPeter sson, H. Nakatsuji, X. Li, M. Caricato, AVMarenich, J. Bloino, BG Janesko, R. Gomperts, B. Mennucci, HPHratc is, JVOrtiz, AFIzmaylov, JLSonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. A., et al .Peng, A. Petrone, T. Henderson, D. Ranasinghe, VG Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M.S. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K.T hrossell, JMontgomery,Jr., JEPeralta, F. Ogliaro, MJBearpark, JJHeyd, ENBrothers, KNKudin, VNStarove rov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, APRendell, JCBurant, SSIyengar, J. Thomas, M.Co ssi, JMMillam, M. Klene, C. Adamo, R. Cammi, JWOchterski, RLMartin, K. Morokuma, O. Farkas, JB Foresman, and DJFox, Gaussian, Inc., Wallingford CT,

[0050] S1 and T n The calculation of the SOC between the levels (n=1, 2, 3, 4) is performed using the aforementioned time-dependent density functional method, as described in the following Non-Patent Document 1. S1 and E Tn Casida-type wave function Ψ using configuration interaction coefficients output in the calculation of S1 and Ψ Tn and the effective charge approximation Breit-Pauli spin-orbit interaction Hamiltonian H eff SOC As software for calculating the SOC, for example, PySOC (Non-Patent Document 1) can be used.

[0051] <Non-Patent Document 1> Evaluation of Spin-Orbit Couplings with Linear-Response Time-Dependent Density Functional Methods Xing Gao, Shuming Bai, Daniele Fazzi, Thomas Niehaus, Mario Barbatti, and Walter Thiel J.Chem.Theory Comput.,2017,13(2),pp515-524

[0052] The relative ST values ​​(ST values ​​of triplets at various levels and S1) of the compounds shown in Tables 1 to 6 are shown in Tables 1 to 6 and Figure 1, with the compounds (comparative compounds 1, 10, and 11) having one carbazole unit introduced as the donor unit (D) as the standard.

[0053] [Table 1]

[0054] [Table 2]

[0055] [Table 3]

[0056] [Table 4]

[0057] [Table 5]

[0058] [Table 6]

[0059] Comparing Tables 1 to 6 reveals the following about the ST values ​​of S1-T4. In Tables 1 and 2, where X in general formula (1) is an oxygen atom, the maximum ST value is about 100 times that of the case where D is one (comparative compound 1). In contrast, in Tables 3, 4, 5, and 6, where X in general formula (1) is a sulfur atom or a selenium atom, respectively, the maximum ST value can be 10,000 times or more that of the case where D is one (comparative compounds 10 and 11). RISC In particular, when X is a sulfur atom, the ST value is up to 80,000 times larger than when X is a selenium atom. This is because the strong heavy atom effect of the selenium atom increases SOC, weakening the effect of the introduction of D.

[0060] <Example> Specific examples of the organic compound of this embodiment are listed below, but the present invention is not limited to these.

[0061] [ka]

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[0065] [ka]

[0066] (2) Organic light-emitting devices Next, the organic light-emitting device of this embodiment will be described. The organic light-emitting device of this embodiment has at least a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is an anode, and the other is a cathode. In the organic light-emitting device of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has an emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, etc. Furthermore, the emitting layer may be a single layer or a laminate consisting of multiple layers.

[0067] In the organic light-emitting device of this embodiment, at least one of the organic compound layers contains the organic compound of this embodiment. Specifically, the organic compound of this embodiment is contained in any of the above-mentioned light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, hole / exciton blocking layer, electron transport layer, electron injection layer, etc. The organic compound of this embodiment is preferably contained in the light-emitting layer.

[0068] In the organic light-emitting device of this embodiment, when the organic compound according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer consisting of only the organic compound according to this embodiment, or may be a layer consisting of the organic compound according to this embodiment and other compounds such as a second organic compound, a third organic compound, etc. In the light-emitting layer, the organic compound according to this embodiment may be used as a guest and doped into a host material (second organic compound), or may be used as an assist dopant and doped into a host material (second organic compound) together with a fluorescent material (third organic compound).

[0069] In the case of the doped type, 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 smaller mass ratio than the host among the compounds constituting the light-emitting layer and is the compound that is primarily responsible for emitting light. The assist dopant is the compound with a smaller mass ratio than the host among the compounds constituting the light-emitting layer and plays a role in sensitizing excitons.

[0070] When the organic compound of this embodiment is used as a guest, the concentration of the organic compound of this embodiment is preferably 0.01% by mass to 50% by mass, and more preferably 10% by mass to 50% by mass, of the entire light-emitting layer. When the organic compound of this embodiment is used as an assist dopant, the concentration of the organic compound of this embodiment is preferably 1% by mass to 50% by mass, and more preferably 10% by mass to 50% by mass, of the entire light-emitting layer. In this case, the concentration of the fluorescent material is preferably 0.01% by mass to 20% by mass, and more preferably 0.01% by mass to 5% by mass, of the entire light-emitting layer.

[0071] The present inventors have conducted various studies and found that when the organic compound according to this embodiment is used as a host or guest in an emitting layer, particularly as a guest in the emitting layer, an element exhibiting high efficiency and high luminance light output and extremely high durability can be obtained. This emitting layer may be a single layer or multiple layers, and it is also possible to mix the emitting color with the emitting color of the organic compound according to this embodiment by including a luminescent material having another emitting color. "Multiple layers" refers to a state in which the emitting layer and another emitting layer are stacked. In this case, the emitting color of the organic light-emitting element is not limited to the emitting color of the organic compound according to this embodiment. More specifically, it may be white or a neutral color. In the case of white, the other emitting layer emits a color other than the emitting color of the organic compound according to this embodiment; for example, if the emitting color of the organic compound according to this embodiment is blue, it will emit green or red. Furthermore, the film formation method is performed by vapor deposition or coating film formation. Details of this will be explained in detail in the examples below.

[0072] 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 limited to the emission color of the organic compound according to this embodiment. More specifically, it may emit white light or an intermediate color.

[0073] <Other compounds> In addition to the organic compound 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 also be used together as needed. Examples of these compounds are listed below.

[0074] As the hole injection / transport material, a material with high hole mobility is preferred, facilitating the injection of holes from the anode and transporting the injected holes to the light-emitting layer. Furthermore, a material with a high glass transition temperature is preferred to reduce film quality degradation, such as crystallization, in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole injection / 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 / transport materials are also suitable for use in electron blocking layers. Furthermore, a mixture of polyethylenedioxythiophene and polystyrene sulfonic acid (PEDOT:PSS), which is commonly used as a hole injection material when fabricating a light-emitting device by a coating method, may also be used. Specific examples of compounds that can be used as hole injection / transport materials are listed below, but the present invention is not limited to these.

[0075] [ka]

[0076] [ka]

[0077] Among the hole-transporting materials listed above, HT16-HT18 can reduce the driving voltage when used in the layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2-HT7, HT10, HT12, and HT22-HT28 may be used in the organic compound layer adjacent to HT16. Hole-transporting polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinyl carbazole (PVK), and derivatives thereof may also be used. In addition, inorganic insulating layers such as SiO2 and SiN, and organic silicon polymers such as siloxane may also be used. Multiple materials may also be used in a single organic compound layer.

[0078] Light-emitting materials primarily related to light-emitting function include donor-acceptor organic compounds, boron-containing complexes, indocarbazole fused ring compounds, 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. Furthermore, when fabricating light-emitting layers using coating methods, luminescent polymer compounds are primarily used. This is because polymer compounds are highly amorphous and therefore less prone to crystallization than small molecule systems. Specific examples of materials that can be used include polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinyl carbazole (PVK), and derivatives thereof. Specific examples of compounds that can be used as light-emitting materials are shown below, but the present invention is not limited to these.

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[0083] Specific examples of compounds that can be used as the light-emitting layer host or light-emitting assist material contained in the light-emitting layer are shown below, but the present invention is not limited to these.

[0084] [ka]

[0085] [ka]

[0086] When the host material is used together with a delayed fluorescent material or a phosphorescent material, the triplet potential of the host material is preferably higher than that of the delayed fluorescent material. Preferred host materials include, but are not limited to, EM32-EM45.

[0087] 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.

[0088] [ka]

[0089] 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.

[0090] <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 protective layer and the color filter. The planarizing layer may be made of acrylic resin, etc. The same applies when a planarizing layer is provided between the color filter and the microlens. Either the first electrode or the second electrode may be an anode, and the other may be a cathode.

[0091] [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.

[0092] [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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] [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 is mainly composed of organic compounds but may also contain inorganic atoms or inorganic compounds. For example, the organic compound layer may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, or the like. The organic compound layer may be disposed between the first electrode and the second electrode, or may be disposed in contact with the first electrode and the second electrode.

[0099] The organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light emitting device according to one embodiment of the present invention are formed by the method shown below.

[0100] The organic compound layer constituting the organic light-emitting device according to one embodiment of the present invention can be formed by a dry process such as vacuum deposition, ionization deposition, sputtering, or plasma. Instead of a dry process, a wet process can be used in which a compound is dissolved in an appropriate solvent and a layer is formed by a known coating method (e.g., spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, capillary coating, or nozzle coating). Among these, vacuum deposition, ionization deposition, inkjet printing, and nozzle coating are preferred for producing large-area organic light-emitting devices.

[0101] When forming a light-emitting layer using a compound highly soluble in an organic solvent among the organic compounds of this embodiment, it is preferable to form the light-emitting layer by a coating method. Examples of the coating method include spin coating, slit coating, printing, inkjet printing, dispensing, and spraying. Alternatively, the light-emitting layer may be formed by a vacuum deposition method.

[0102] 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.

[0103] 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.

[0104] 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.

[0105] The thickness of each layer in the organic light-emitting device is preferably 1 nm to 10 μm in general, and particularly the thickness of the light-emitting layer of the organic compound layer is preferably 10 nm to 100 nm in order to obtain effective light-emitting characteristics.

[0106] [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.

[0107] [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.

[0108] [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.

[0109] 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.

[0110] [Microlens] The organic light-emitting element may have an optical component such as a microlens on its light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be intended to increase the amount of light extracted from the organic light-emitting element and control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be determined in the same way in any cross-sectional view. In other words, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the semicircle is the vertex of the microlens.

[0111] 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.

[0112] [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.

[0113] [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.

[0114] 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.

[0115] [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.

[0116] A pixel has an area, also called a pixel aperture, from which light is emitted. 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.

[0117] 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.

[0118] <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.

[0119] The display device may be an image information processing device having an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., an information processing unit that processes the input information, and displays the input image on a display unit. The display device has a plurality of pixels, at least one of which may have an organic light-emitting element of this embodiment and an active element such as a transistor connected to the organic light-emitting element. In this case, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate. The image display device has an input unit for inputting image information and a display unit for outputting an image, and the display unit has the display device of this embodiment.

[0120] 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.

[0121] Next, a display device according to this embodiment will be described with reference to the drawings. Fig. 2 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).

[0122] FIG. 2(a) is a cross-sectional schematic diagram of an example of a pixel, which is a component of the display device according to this embodiment. The pixel includes subpixels 10. The subpixels are divided into 10R, 10G, and 10B based on their light emission. The emitted colors may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the subpixels may be selectively transmitted or color-converted using a color filter or the like. Each subpixel 10 includes a reflective electrode serving as a first electrode 2 on an interlayer insulating layer 1, an insulating layer 3 covering the 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.

[0123] 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).

[0124] 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 contacts the organic compound layer 4 and becomes a light-emitting region.

[0125] The organic compound layer 4 includes a hole injection layer 41 , a hole transport layer 42 , a light emitting layer 43 , a hole blocking layer 44 , and an electron transport layer 45 .

[0126] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0127] 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.

[0128] 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.

[0129] The display device 100 in Fig. 2(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 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film 19.

[0130] 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. 2(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.

[0131] 2(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.

[0132] In the display device 100 of FIG. 2(b), transistors are used as switching elements, but other switching elements such as MIM elements may be used instead.

[0133] The transistors used in the display device 100 of Fig. 2(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.

[0134] The transistors included in the display device 100 of Fig. 2(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 formed integrally.

[0135] 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.

[0136] 3 is a schematic diagram illustrating an example of a display device according to this embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The 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.

[0137] 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.

[0138] 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.

[0139] 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.

[0140] 4A 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.

[0141] 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.

[0142] 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.

[0143] FIG. 4(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.

[0144] FIG. 5 is a schematic diagram illustrating an example of a display device according to this embodiment. FIG. 5(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. 5(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.

[0145] FIG. 5(b) is a schematic diagram illustrating another example of a display device according to this embodiment. The display device 1310 in FIG. 5(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.

[0146] FIG. 6(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. If necessary, a cover may be provided on the outermost surface.

[0147] 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. The lighting device may have an inverter circuit. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device may have a color filter.

[0148] 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.

[0149] 6(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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] An application example of the display device of each of the above-described embodiments will be described with reference to Fig. 7. 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. The image capturing and display device used in such an application example includes an image capturing device capable of photoelectrically converting visible light and a display device capable of emitting visible light.

[0154] Fig. 7(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using Fig. 7(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.

[0155] 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.

[0156] FIG. 7(b) is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 7(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. 7(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.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 8(a) is a schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a 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.

[0163] 8(b) and 8(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. 8(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoconductor 27. FIG. 8(c) shows a configuration different from FIG. 8(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. 8(c) can also be described as a grid arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0164] As described above, by using the device using the organic light-emitting element according to this embodiment, it is possible to achieve a display with good image quality and stability even over a long period of time. Furthermore, by using the device using the organic light-emitting element according to this embodiment, it is possible to achieve both good visibility outdoors due to highly efficient and bright light output and power-saving display.

[0165] (3) Ink composition Next, an ink composition according to one embodiment of the present invention will be described. The ink composition according to this embodiment contains at least one organic compound according to this embodiment.

[0166] The organic compound of this embodiment has good solubility in organic solvents and can be used as an ink composition. Furthermore, by using the ink composition of this embodiment, it is possible to prepare the organic compound layer, particularly the light-emitting layer, constituting the organic light-emitting device of this embodiment by a coating method, and large-area devices can be easily produced at relatively low cost.

[0167] Examples of solvents that dissolve the organic compound of this embodiment include toluene, xylene, mesitylene, dioxane, methylnaphthalene, tetrahydrofuran, diglyme, 1,2-dichlorobenzene, and 1,2-dichloropropane. These organic solvents can be used alone or in combination of two or more. Among these, it is preferable to use organic solvents that have a moderate evaporation rate, specifically, organic solvents with a boiling point of about 70°C to 200°C, in order to easily obtain a thin film with a uniform thickness.

[0168] The ink composition of this embodiment may also contain other compounds that serve as additives, such as the above-mentioned known light-emitting layer hosts or light-emitting assist materials, hole-transporting materials, light-emitting materials, and electron-transporting materials.

[0169] The concentration of the organic compound of this embodiment in the ink composition is preferably 0.05% by mass or more and 20% by mass or less, and more preferably 0.1% by mass or more and 5% by mass or less, based on the total mass of the composition.

[0170] The ink composition of this embodiment can be formed into a film by a spin coating method, a bar coating method, a slit coating method, an inkjet method, a nozzle coating method, a casting method, a gravure printing method, etc. The organic light-emitting element of this embodiment can be used to construct a display device such as a display by forming a layer containing the organic compound of this embodiment on an electrode formed in a pixel pattern. [Example]

[0171] Examples will be described below, but the present invention is not limited to these examples.

[0172] Example 1 (Synthesis of Compound) <Synthesis of Comparative Example Compound 1 (Comparative Compound 10 in Table 3)> [ka]

[0173] (1) Synthesis of IM1 A 100 mL Schlenk flask was charged with 2-bromo-1,3,5-trifluorobenzene (8.2 g, 39 mmol), K2CO3 (11 g, 80 mmol), benzenethiol (4.3 g, 39 mmol), and triglyme (20 mL) and stirred at 100 °C under nitrogen for 15 hours. After returning to room temperature, water was added to the reaction solution, which was then extracted with hexane. The organic layer was washed with water. The organic layer was dried over Na2SO4, the filtrate was collected, and the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel chromatography (eluent: hexane). The resulting solid was recrystallized from hexane to give IM1 as a white solid (yield: 7.4 g, 25 mmol, 64%).

[0174] 1 H NMR(400MHz,CDCl3) δ 7.57-7.53(m,2H),7.50-7.46(m,3H),6.65(td,J=8.4,2.8Hz,1H),6.23-6.20(m,1H).

[0175] (2) Synthesis of IM2 IM1 (2.0 g, 6.6 mmol), carbazole (2.9 g, 17 mmol), Cs2CO3 (7.5 g, 23 mmol), and dry DMF (33 mL) were added to a 300 mL Schlenk flask and stirred at 140 °C under nitrogen for 14 hours. After cooling to room temperature, water was added to the reaction solution and the mixture was filtered through Celite. The residue was washed with MeOH, and the remaining residue was eluted with CHCl3. The filtrate was collected and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography (eluent: CHCl2 / Hexane = 1 / 9, v / v) to give IM2 as a white solid (yield: 2.9 g, 4.9 mmol, 74%).

[0176] 1 H NMR(400MHz,CD2Cl2) δ 8.21-8.18(m,2H),8.09-8.06(m,2H),7.78-7.75(m,2H),7.56-7.45(m,6H),7.40-7.25(m,10H),7.09(d,J=2.4Hz,1H).

[0177] (3) Synthesis of Comparative Compound 1 A 100 mL Schlenk flask was charged with IM2 (0.99 g, 1.7 mmol) and tert-butylbenzene (24 mL) and dissolved. The flask was then cooled to 0 °C, and n-BuLi (1.6 M in hexane, 1.4 mL, 2.2 mmol) was added dropwise. After stirring at 70 °C for 1 hour, the flask was cooled to 0 °C, and BBr3 (0.30 mL, 3.2 mmol) was added dropwise. After stirring at room temperature for 2 hours, the flask was cooled to 0 °C, and NEt(i-Pr)2 (0.80 mL, 4.6 mmol) was added dropwise. After stirring at room temperature for 1 hour, the mixture was stirred at 140 °C for 16 hours. After cooling to room temperature, water was added to the reaction solution, which was then extracted with CHCl2. The organic layer was washed with water. The mixture was dried over NaSO4, and the filtrate was collected. The solvent was evaporated under reduced pressure. The resulting crude product was added with MeOH, and the precipitate was collected by filtration. The precipitate was purified by silica gel chromatography (developing solvent: CH2Cl2) to obtain Comparative Compound 1 as a yellow solid (yield: 0.42 g, 0.80 mmol, 47% yield).

[0178] 1 H NMR(400MHz,CD2Cl2) δ 8.90-8.84(m,2H),8.65(s,1H),8.51(d,J=7.6Hz,1H),8.30-8.25(m,4H),7.86-7.39(m,13H). MS(MALDI-TOF):m / z found 524.26 ([M] + );calcd for C 36 H 21 BN2S 524.15.

[0179] <Synthesis of Comparative Example Compound 2> [ka]

[0180] (1) Synthesis of 2-bromo-3,4-difluoro-1-iodobenzene (IM3) A 300 mL three-neck flask was charged with 2-bromo-3,4-difluoroaniline (8.0 g, 38 mmol) and dilute hydrochloric acid (6 M, 80 mL) and cooled to 0 °C. NaNO (4.0 g, 58 mmol) dissolved in water (18 mL) was added dropwise and stirred at 0 °C for 20 min (diazonium salt solution). KI (13 g, 78 mmol) dissolved in water (28 mL) was added to a 500 mL beaker, and the diazonium salt solution was added dropwise and stirred at room temperature for 30 min. The mixture was filtered, washed with water and NaHSO solution, and the residue was eluted with CHCl. ​​The solvent in the filtrate was evaporated under reduced pressure, and the resulting crude product was purified by silica gel chromatography (eluent: hexane) to give IM3 as a white solid (yield: 11 g, 34 mmol, 89%).

[0181] 1 H NMR(400MHz,CD2Cl2) δ 7.72-7.68(m,1H),7.05-6.99(m,1H).

[0182] (2) Synthesis of IM4 IM4 was obtained in 45% yield by the same method as for the synthesis of IM2.

[0183] (3) Synthesis of IM5 A 50 mL Schlenk flask was charged with IM4 (0.61 g, 0.99 mmol), benzenethiol (1.0 g, 9.1 mmol), DPEphos (25 mg, 0.046 mmol), [Pd(dba)2] (30 mg, 0.052 mmol), tBuONa (0.13 g, 1.4 mmol), and dry toluene (2.8 mL) and stirred at 80 °C under nitrogen for 4 h. After returning to room temperature, water was added to the reaction solution, which was then extracted with CHCl2. The organic layer was washed with water and aqueous NaCl solution. NaSO4 was added for drying, and the filtrate was recovered. The solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography (eluent: CHCl2 / hexane = 2 / 5, v / v) to give IM5 as a white solid (yield: 0.50 g, 0.84 mmol, 85%).

[0184] 1 H NMR(400MHz,CDCl3) δ 7.78-7.68(m,6H),7.60-7.55(m,3H),7.47(d,J=8.8Hz,1H),7.10-6.97(m,13H).

[0185] (4) Synthesis of Comparative Compound 2 Comparative Compound 2 was obtained in a yield of 50% in the same manner as Comparative Compound 1.

[0186] 1 H NMR(400MHz,CD2Cl2) δ 8.73-8.69(m,2H),8.27(dd,J=7.2,1.2Hz,1H),8.02(d,J=8.4Hz,1H),7.97-7.94(m,2H),7.83 -7.53(m,7H),7.16-7.14(m,4H),6.94(s,1H),6.83-6.76(m,2H),6.29(dd,J=7.2,1.2Hz,1H). MS(MALDI-TOF):m / z found 524.33([M] + );calcd for C 36 H 21 BN2S 524.15.

[0187] <Synthesis of Example Compound 1 (Compound 1 in Table 3)> [ka]

[0188] (1) Synthesis of IM6 A 100 mL Schlenk flask was charged with 2-bromo-3,4,6-trifluoroaniline (13 g, 58 mmol), diphenyl disulfide (4.3 g, 20 mmol), and DMSO (22 mL) and purged with nitrogen. After cooling to 0 °C, tBuONO (10 mL, 84 mmol) was added dropwise. The mixture was stirred at 0 °C for 30 minutes and then at room temperature for 41 hours. Water was added to the reaction solution, which was then extracted with hexane. The organic layer was washed with water and aqueous NaCl solution. NaSO was added for drying, and the NaSO hydrate was filtered off. The filtrate was recovered, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography (eluent: hexane) and further purified by preparative GPC with recycling. IM6 was obtained as a pale yellow oil (yield: 1.6 g, 5.0 mmol, 13%).

[0189] (2) Synthesis of IM7 IM6 (1.6 g, 5.0 mmol), carbazole (3.4 g, 20 mmol), cesium carbonate (8.7 g, 27 mmol), and dry DMF (25 mL) were added to a 100 mL Schlenk flask and stirred at 140 °C under nitrogen for 10 hours. After cooling to room temperature, water was added to the reaction solution and the mixture was filtered through Celite. The residue was washed with MeOH, and the remaining residue was eluted with CHCl3. The filtrate was collected and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography (eluent: CHCl2 / Hexane = 2 / 5, v / v) to give IM7 as a white solid (yield: 1.9 g, 2.5 mmol, 50%).

[0190] (3) Synthesis of Example Compound 1 In the same manner as in the preparation of Comparative Example Compound 1, Example Compound 1 was obtained as a yellow solid (yield: 0.19 g, 0.28 mmol, 30%).

[0191] 1 H NMR (400MHz,CD2Cl2) δ 8.84-8.78(m,2H),8.40(dd,J=7.2,1.2Hz,1H),8.26(dq,J=8.0,1.2,0.8Hz,2H),8.23(s,1H),7.98-7.94(m,2H),7.83(t,J=7. 6Hz,2H),7.60-7.55(m,3H),7.45-7.34(m,5H),7.26(d,J=8.0Hz,2H),7.16-7.15(m,4H),7.02-6.89(m,3H),6.40-6.36(m,1H). MS(MALDI-TOF):m / z found 689.41([M]+);calcd for C 48 H 28 BN3S 689.21.

[0192] <Synthesis of Example Compound 2 (Compound 4 in Table 3)> [ka]

[0193] (1) Synthesis of IM8 IM8 was obtained in 13% yield by the same method as IM5.

[0194] (2) Synthesis of IM9 IM9 was obtained in 32% yield by the same method as IM4.

[0195] (3) Synthesis of Example Compound 2 Example Compound 2 was obtained in a yield of 18% in the same manner as Example Compound 1. MS: m / z found 855.8 ([M] + );calcd for 854.8.

[0196] Example 2 (Optical Property Spectrum in Solution) Example compounds 1 and 2 and Comparative Example compounds 1 and 2 were each -5 PL spectrum, PL lifetime, PLQY (reverse intersystem crossing rate (k RISC [10 -6 s -1 The results are shown in Table 7 as relative values ​​when the result of Comparative Example Compound 1 is set to 100%.

[0197] [Table 7]

[0198] From Table 7, Example Compounds 1 and 2 have a higher k RISC was found to be fast.

[0199] Example 3 (Evaluation of EL spectrum) <Fabrication of element 1> A glass substrate was used as a transparent conductive support substrate (ITO substrate) by forming a 50 nm thick ITO film as an anode by sputtering. On this ITO substrate, the organic compound layer and electrode layer shown in Table 8 were formed for 10 minutes. -5 The electrodes were continuously formed by vacuum deposition using resistance heating in a vacuum chamber at 3 Pa. 2 It was made so that

[0200] [Table 8]

[0201] Next, in order to prevent deterioration of the element due to moisture absorption, the element was covered with a protective glass plate in a dry air atmosphere and sealed with an acrylic resin adhesive. In this way, an organic light-emitting element was obtained.

[0202] <Preparation of element 2 and comparative elements 1 and 2> Device 2 and comparative devices 1 and 2 were produced in the same manner as Device 1, except that the compounds shown in Table 9 were used instead of Example Compound 1 as guest materials in the light-emitting layer.

[0203] <Evaluation> The obtained organic light-emitting device was driven at a driving current of 100 mA / m using the ITO electrode as the anode and the Al electrode as the cathode. 2 Drive current 1,000mA / m for EQE (EQE100) 2 The ratio (EQE1000 / EQE100) of EQE (EQE1000) at the time of measurement was measured as the roll-off reduction effect (%). Each result is shown in Table 9 as a relative value when the result of Comparative element 1 is set to 100%.

[0204] [Table 9]

[0205] As shown in Table 9, the roll-off reducing effect of the elements 1 and 2, which used the example compounds 1 and 2, respectively, was improved compared to the comparative elements 1 and 2, which used the comparative compounds 1 and 2.

[0206] ≪Included components≫ The disclosure of this embodiment includes the following configuration. (Configuration 1) An organic compound represented by general formula (1): In general formula (1), rings a to c are each independently selected from substituted or unsubstituted aryl rings and substituted or unsubstituted heteroaryl rings. X is a sulfur atom or a selenium atom. R1 to R3 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group, with the proviso that at least two of R1 to R3 are each independently selected from groups represented by general formula (2). In general formula (2), R4 to R 11 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. 11 Any two adjacent ones of these may be bonded to a group represented by general formula (3). In general formula (3), R 12 ~R 15 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. Y is selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, and a nitrogen atom substituted with an alkyl group or an aryl group. In general formula (2), * represents the bonding position with general formula (1). In general formula (3), * represents the bonding position with general formula (2).

[0207] (Configuration 2) The organic compound according to configuration 1, which is represented by general formula (4): In general formula (4), Y1 to Y7 are each independently selected from carbon atoms and nitrogen atoms. When Y1 to Y7 are carbon atoms, R 16 ~R 22 and combine. R 16 ~R 26 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. (Configuration 3) 3. The organic compound according to claim 2, wherein all of Y1 to Y7 are carbon atoms. (Configuration 4) The substituents that the rings a to c may have, the R to R 15 , the R1 to R 15 at least one of the substituents that may be present on the organic compound according to any one of structures 1 to 3 is selected from a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, a substituted or unsubstituted heterocyclic group having from 6 to 18 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, and a cyano group. (Configuration 5) The substituents that the rings a to c may have, the R to R 15 , the R1 to R 15 5. The organic compound according to claim 4, wherein at least one of the substituents which may be possessed by the group is selected from Group A. (Configuration 6) The substituents that the rings a to c may have, the R to R 15 , the R1 to R 15 The organic compound according to structure 5, wherein any of the substituents which may be possessed by is selected from Group A.

[0208] (Configuration 7) 7. The organic compound according to any one of structures 1 to 6, wherein X is a sulfur atom. (Configuration 8) The R8 to R 11 8. The organic compound according to any one of structures 1 to 7, wherein adjacent two of the groups may be bonded to the group represented by general formula (3). (Configuration 9) 9. The organic compound according to claim 8, wherein R8 and R9 may be bonded to the group represented by general formula (3). (Configuration 10) 10. The organic compound according to any one of structures 1 to 9, wherein R1 to R3 are each independently selected from a hydrogen atom and a substituted or unsubstituted aryl group. (Configuration 11) The R4 to R 11 , the R 12 ~R 15 and are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. (Configuration 12) 12. The organic compound according to any one of structures 1 to 11, wherein Y is selected from the group consisting of an oxygen atom and a nitrogen atom substituted with an aryl group. (Configuration 13) R 16 ~R 26 4. The organic compound according to claim 2 or 3, wherein x and x are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group.

[0209] (Configuration 14) An organic light-emitting device having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, 14. 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 13. (Configuration 15) 15. The organic light-emitting device according to configuration 14, wherein the layer containing the organic compound is a light-emitting layer. (Configuration 16) 16. The organic light-emitting device according to claim 15, wherein the light-emitting layer contains a second organic compound different from the organic compound. (Configuration 17) 17. The organic light-emitting device according to claim 16, wherein the concentration of the organic compound is 0.01% by mass or more and 50% by mass or less with respect to the entire light-emitting layer. (Configuration 18) 18. The organic light-emitting device according to claim 17, wherein the concentration of the organic compound is 10% by mass or more and 50% by mass or less with respect to the entire light-emitting layer. (Configuration 19) 19. The organic light-emitting device according to any one of Structures 16 to 18, wherein the light-emitting layer contains a third organic compound different from both the organic compound and the second organic compound. (Configuration 20) 20. The organic light-emitting device according to claim 19, wherein the concentration of the organic compound is 1% by mass or more and 50% by mass or less with respect to the entire light-emitting layer. (Configuration 21) 21. The organic light-emitting device according to Configuration 20, wherein the concentration of the organic compound is 10% by mass or more and 50% by mass or less with respect to the entire light-emitting layer.

[0210] (Configuration 22) 14. An ink composition comprising the organic compound according to any one of claims 1 to 13.

[0211] (Configuration 23) 22. A display device comprising a plurality of pixels, at least one of which comprises an organic light-emitting element according to any one of structures 14 to 21 and a transistor connected to the organic light-emitting element. (Configuration 24) 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; 22. A photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to any one of the fourteenth to twenty-first aspects. (Configuration 25) 22. An electronic device comprising: a display unit having the organic light-emitting element according to any one of configurations 14 to 21; a housing in which the display unit is provided; and a communication unit provided in the housing for communicating with the outside. (Configuration 26) 22. A lighting device comprising: a light source having the organic light-emitting element according to any one of Structures 14 to 21; and a light diffusion section or an optical filter that transmits light emitted by the light source. (Configuration 27) A moving body comprising: a lighting fixture having the organic light-emitting element according to any one of configurations 14 to 21; and a vehicle on which the lighting fixture is provided. (Configuration 28) 22. An exposure light source for an electrophotographic image forming apparatus, comprising the organic light-emitting element according to any one of Structures 14 to 21. [Explanation of symbols]

[0212] 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< / y> < / x>

Claims

1. An organic compound represented by the following general formula (1): 【Chemistry 1】 In general formula (1), rings a to c are each independently selected from substituted or unsubstituted aryl rings and substituted or unsubstituted heteroaryl rings. X is a sulfur atom or a selenium atom. R 1 ~R 3 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. 1 ~R 3 At least two of the above are independently selected from groups represented by the following general formula (2): 【Chemistry 2】 In general formula (2), R 4 ~R 11 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. 4 ~R 11 Any two adjacent ones of these may be bonded to a group represented by the following general formula (3). 【Transformation 3】 In general formula (3), R 12 ~R 15 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group. Y is selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, and a nitrogen atom substituted with an alkyl group or an aryl group. In general formula (2), * represents the bonding position with general formula (1). In general formula (3), * represents the bonding position with general formula (2).

2. 2. The organic compound according to claim 1, represented by the following general formula (4): 【Chemistry 4】 In the general formula (4), Y 1 or Y 7 are each independently selected from a carbon atom and a nitrogen atom. 1 or Y 7 is R when it is a carbon atom 16 ~R 22 and combine. R 16 ~R 26 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, and a cyano group.

3. The Y 1 or Y 7 The organic compound according to claim 2, wherein all of are carbon atoms.

4. The substituents that the rings a to c may have, the R 1 ~R 15 , the R 1 ~R 15 4. The organic compound according to claim 1, wherein at least one of the substituents that may be possessed by the group consisting of a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, a substituted or unsubstituted heterocyclic group having from 6 to 18 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, and a cyano group.

5. The substituents that the rings a to c may have, the R 1 ~R 15 , the R 1 ~R 15 5. The organic compound according to claim 4, wherein at least one of the substituents which may be possessed by the group is selected from the following Group A: 【Transformation 5】

6. The substituents that the rings a to c may have, the R 1 ~R 15 , the R 1 ~R 15 6. The organic compound according to claim 5, wherein any of the substituents which may be possessed by is selected from Group A.

7. 4. The organic compound according to claim 1, wherein X is a sulfur atom.

8. The R 8 ~R 11 4. The organic compound according to claim 1, wherein adjacent two of the groups may be bonded to the group represented by general formula (3).

9. The R 8 and R 9 may be bonded to the group represented by the general formula (3).

10. The R 1 ~R 3 and are each independently selected from the group consisting of a hydrogen atom and a substituted or unsubstituted aryl group.

11. The R 4 ~R 11 , the R 12 ~R 15 4. The organic compound according to claim 1, wherein each of the groups is independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group.

12. 4. The organic compound according to claim 1, wherein Y is selected from the group consisting of an oxygen atom and a nitrogen atom substituted with an aryl group.

13. The R 16 ~R 26 4. The organic compound according to claim 2, wherein each of and is independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group.

14. An organic light-emitting device having a first electrode, a second electrode, and 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 .

15. The organic light-emitting device according to claim 14, wherein the layer containing the organic compound is a light-emitting layer.

16. The organic light-emitting device according to claim 15 , wherein the light-emitting layer comprises a second organic compound different from the organic compound.

17. 17. The organic light-emitting element according to claim 16, wherein the concentration of the organic compound is 0.01% by mass or more and 50% by mass or less with respect to the entire light-emitting layer.

18. 18. The organic light-emitting element according to claim 17, wherein the concentration of the organic compound is 10% by mass or more and 50% by mass or less with respect to the entire light-emitting layer.

19. The organic light-emitting device according to claim 16 , wherein the light-emitting layer comprises a third organic compound different from both the organic compound and the second organic compound.

20. 20. The organic light-emitting element according to claim 19, wherein the concentration of the organic compound is 1% by mass or more and 50% by mass or less with respect to the entire light-emitting layer.

21. 21. The organic light-emitting element according to claim 20, wherein the concentration of the organic compound is 10% by mass or more and 50% by mass or less with respect to the entire light-emitting layer.

22. An ink composition comprising the organic compound according to claim 1 .

23. 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 14 and a transistor connected to the organic light-emitting element.

24. 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 14, wherein the display section comprises the organic light-emitting element according to claim 14.

25. 15. An electronic device comprising: a display unit having the organic light-emitting element according to claim 14; a housing in which the display unit is provided; and a communication unit provided in the housing for communicating with an external device.

26. 15. A lighting device comprising: a light source having the organic light-emitting element according to claim 14; and a light diffusion section or an optical filter that transmits light emitted by the light source.

27. A moving body comprising: a lighting fixture having the organic light-emitting element according to claim 14; and a body on which the lighting fixture is provided.

28. An exposure light source for an electrophotographic image forming apparatus, comprising the organic light emitting device according to claim 14.

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