Organic compound and organic light-emitting element

Abstract

This organic compound is represented by formula (1). In formula (1), R1 and R2 are each independently selected from hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, and the like. However, at least one of R1 and R2 is a substituent. R3 and R4 are each independently selected from substituted or unsubstituted aryl groups and the like. D1 and D2 are each independently selected from groups represented by formula (2). In formula (2), R5 to R12 are each independently selected from hydrogen atoms, substituted or unsubstituted alkyl groups, and the like. Two adjacent ones of R9 to R12 may be substituted with a group represented by formula (3). In formula (3), R13 to R16 are each independently selected from hydrogen atoms, substituted or unsubstituted alkyl groups, and the like. X is selected from oxygen atoms, sulfur atoms, and the like. In formula (2), symbol a represents a bonding position to formula (1). In formula (3), symbol * represents a bonding position to formula (2).

Description

Organic compound and organic light-emitting device

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

[0002] An organic light-emitting device (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 a 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.

[0003] Delayed fluorescent materials (TADF materials) generally have a structure in which a donor moiety and an acceptor moiety are bonded (hereinafter referred to as "DA type"). DA-type TADF materials are materials that, in an excited state, undergo reverse intersystem crossing (RISC) from an excited triplet state to an excited singlet 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 route via reverse intersystem crossing, thereby achieving higher luminous efficiency than ordinary fluorescent materials.

[0004] Since this principle was clarified, various TADF materials have been discovered through extensive research. As DA-type TADFs incorporating triazine and carbazole, Compound A is disclosed in Patent Document 1, and Compound B is disclosed in Patent Document 2.

[0005]

[0006] International Publication No. WO 2016 / 181846 International Publication No. WO 2016 / 158540

[0007] Compound A described in Patent Document 1 has low stability because the phenyl group bonded to triazine has two carbazolyl groups at the ortho position. Compound B described in Patent Document 2 has a reverse intersystem crossing rate constant (k ＲＩＳＣ ) is low.

[0008] The present invention has been made in view of the above problems, and provides a method for producing a compound having high stability and a low reverse intersystem crossing rate constant (kＲＩＳＣ The object of the present invention is to provide an organic compound having a large molecular weight.

[0009] An organic compound represented by the following general formula (1):

[0010]

[0011] In general formula (1), R １ and R ２ are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group not containing a nitrogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group. １ and R ２ At least one of is a substituent.

[0012] R ３ and R ４ are each independently selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, and a cyano group.

[0013] D １ and D ２ are each independently selected from groups represented by the following general formula (2):

[0014]

[0015] In general formula (2), R ５ ~R １２ 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 silyl group, and a cyano group. ９ ~R １２ Any two adjacent ones of these may be substituted with a group represented by the following general formula (3).

[0016]

[0017] In general formula (3), R １３ ~R １６ 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 silyl group, and a cyano group.

[0018] X 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.

[0019] In general formula (2), a indicates the bonding position with general formula (1). In general formula (3), * indicates the bonding position with general formula (2).

[0020] According to the present invention, a method for producing a hydroxybenzoate having excellent stability and a low reverse intersystem crossing rate constant (k ＲＩＳＣ ) can provide an organic compound with a large molecular weight.

[0021] 1 is a diagram showing a HOMO orbital distribution of Compound 1. FIG. 2 is a diagram showing a LUMO orbital distribution of Compound 1. FIG. 3 is a diagram showing a HOMO orbital distribution of Comparative Compound 4. FIG. 4 is a diagram showing a LUMO orbital distribution of Comparative Compound 4. FIG. 5 is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention. FIG. 6 is a schematic cross-sectional view of an example of a display device using an organic light-emitting device according to one embodiment of the present invention. FIG. 7 is a schematic view showing an example of a display device according to one embodiment of the present invention. FIG. 8 is a schematic view showing an example of an imaging device according to one embodiment of the present invention. FIG. 9 is a schematic view showing an example of an electronic device according to one embodiment of the present invention. FIG. 10 is a schematic view showing an example of a display device according to one embodiment of the present invention. FIG. 11 is a schematic view showing an example of a bendable display device. FIG. 12 is a schematic view showing an example of a lighting device according to one embodiment of the present invention. FIG. 13 is a schematic view showing an example of a moving object having a vehicle lamp according to one embodiment of the present invention. FIG. 14 is a schematic view showing an example of a wearable device according to one embodiment of the present invention. FIG. 15 is a schematic view showing another example of a wearable device according to one embodiment of the present invention. FIG. 16 is a schematic view of a head-mounted display as a display device according to one embodiment of the present invention. FIG. 17 is a schematic view of a head-mounted display as a display device according to one embodiment of the present invention. FIG. 18 is a schematic view showing an example of an image forming device according to one embodiment of the present invention. FIG. 19 is a schematic view showing an example of an exposure light source of an image forming device according to one embodiment of the present invention. FIG. 19 is a schematic view showing an example of an exposure light source of an image forming device according to one

[0022] In this specification, examples of halogen atoms include, but are not limited to, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0023] Examples of chalcogen atoms include, but are not limited to, oxygen atoms, sulfur atoms, selenium atoms, and tellurium atoms.

[0024] The alkyl group may have from 1 to 40 carbon atoms, from 1 to 20 carbon atoms, from 1 to 10 carbon atoms, from 1 to 6 carbon atoms, or from 1 to 4 carbon atoms. Specific examples include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, a pentyl group, a hexyl group, an octyl group, a cyclohexyl group, a tertiary pentyl group, and a 3-methylpentan-3-yl group.

[0025] The aryl group may have from 6 to 20 carbon atoms, from 6 to 18 carbon atoms, from 6 to 15 carbon atoms, or from 6 to 12 carbon atoms. Specific examples include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, an anthranyl group, a perylenyl group, a chrysenyl group, and a fluoranthenyl group.

[0026] The heterocyclic group may be a heterocyclic group having 3 to 24 carbon atoms, 3 to 18 carbon atoms, 3 to 12 carbon atoms, or 5 to 12 carbon atoms. The heterocyclic group may also be a heteroaryl group. Specific examples include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, and a phenanthrolyl group.

[0027] The amino group may be a substituted amino group substituted with an alkyl group or an aryl group, and may be a substituted amino group substituted with an alkyl group having from 1 to 4 carbon atoms or an aryl group having from 6 to 12 carbon atoms. Specific examples include, but are not limited to, an N-methylamino group, an N-ethylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-methyl-N-ethylamino group, an N-benzylamino group, an N-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilino group, an N,N-diphenylamino group, an N,N-dinaphthylamino group, an N,N-difluorenylamino group, an N-phenyl-N-tolylamino group, an N,N-ditolylamino group, an N-methyl-N-phenylamino group, an N,N-dianisolylamino group, an N-mesityl-N-phenylamino group, an N,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, and an N-piperidyl group.

[0028] The alkoxy group may have from 1 to 40 carbon atoms, from 1 to 20 carbon atoms, or from 1 to 10 carbon atoms. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, and a benzyloxy group.

[0029] Specific examples of the aryloxy group include, but are not limited to, a phenoxy group.

[0030] Specific examples of heteroaryloxy groups include, but are not limited to, thienyloxy groups.

[0031] A silyl group is a group in which the silicon atom has a hydrogen atom or a substituent. The substituent may be a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. The substituted or unsubstituted alkyl group carried by the silicon atom may be a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. The substituted or unsubstituted aryl group carried by the silicon atom may be a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. The silyl group may be a trialkylsilyl group or a triarylsilyl group. Specific examples include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0032] Examples of substituents that the alkyl group, aryl group, heterocyclic group, amino group, alkoxy group, aryloxy group, heteroaryloxy group, and silyl group may further have include, but are not limited to, halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, and tertiary butyl group; alkoxy groups such as methoxy group, ethoxy group, and propoxy group; amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, and ditolylamino group; aryloxy groups such as phenoxy group; aryl groups such as phenyl group and biphenyl group; heterocyclic groups such as pyridyl group and pyrrolyl group; and cyano group.

[0033] (1) Organic Compound First, the organic compound according to this embodiment will be described. The organic compound according to this embodiment is an organic compound represented by the following general formula (1). The isotope species of hydrogen atoms present in the molecule of the organic compound according to this embodiment is not particularly limited. For example, １ H, or part or all of ２ The organic compound according to this embodiment may be a compound that exhibits delayed fluorescence, or may be a compound that exhibits thermally activated delayed fluorescence (TADF).

[0034]

[0035] <R １ , R ２In general formula (1), R １ and R ２ are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group not containing a nitrogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group. １ and R ２ At least one of R is a substituent. The substituent is a group other than a hydrogen atom or a deuterium atom. That is, R １ and R ２ At least one of the groups may be a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group not containing a nitrogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted silyl group.

[0036] Here, the heterocyclic group not containing a nitrogen atom refers to a heterocyclic group other than a heterocyclic group containing a nitrogen atom. The heterocyclic group containing a nitrogen atom refers to a group containing a nitrogen atom in the skeleton other than the substituents further possessed by the heterocyclic group. Specific examples include a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, and a phenanthrolyl group.

[0037] R １ and R ２ are preferably a hydrogen atom, a deuterium atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, an unsubstituted dibenzochalcogenyl group, or an unsubstituted triphenylsilyl group. １ and R ２ More preferably, each of the groups represents an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, an unsubstituted dibenzochalcogenyl group, or an unsubstituted triphenylsilyl group.

[0038] In addition, from the viewpoint of the stability of the compound, R １ , R ２It is preferable that at least one of the groups is a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, or a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms and not containing a nitrogen atom.

[0039] <R ３ , R ４ In general formula (1), R ３ and R ４ are each independently selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, and a cyano group. ３ and R ４ are preferably each independently selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group, are more preferably a substituted or unsubstituted aryl group having from 6 to 12 carbon atoms and a substituted or unsubstituted heterocyclic group having from 5 to 12 carbon atoms, and are even more preferably a substituted or unsubstituted phenyl group.

[0040] <D １ , D ２ In the general formula (1), D １ and D ２ are each independently selected from groups represented by the following general formula (2):

[0041]

[0042] [R ５ ~R １２ In general formula (2), R ５ ~R １２ 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 silyl group, and a cyano group.

[0043] R ５ ~R １２is preferably a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms, or a cyano group.

[0044] In addition, from the viewpoint of the stability of the compound, R ７ , R １０ At least one of these is preferably a substituent, more preferably a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms, or a cyano group, and even more preferably a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, or a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms. The substituent is a group other than a hydrogen atom or a deuterium atom.

[0045] R ９ ~R １２ Two adjacent groups among R may be substituted with a group represented by the following general formula (3): ９ ~R １２ Specifically, the two adjacent ones are R ９ and R １０ , R １０ and R １１ , or R １１ and R １２ Among these, R ９ and R １０ is preferably substituted with a group represented by the following general formula (3) from the viewpoint of device life.

[0046] For example, the general formula (3) is R １１ and R １２ The substitution by means that one of the * in the general formula (3) is R １１ and the other * is R １２ This refers to substituting a carbon atom having

[0047]

[0048] [R １３ ~R １６In the general formula (3), R １３ ~R １６ 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 silyl group, and a cyano group. １３ ~R １６ may each independently be selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 12 carbon atoms, and a substituted or unsubstituted heterocyclic group having from 5 to 12 carbon atoms; may each independently be selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, and a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, or may be a hydrogen atom.

[0049] [X] In the general formula (3), X 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. X may be an oxygen atom, a sulfur atom, or a nitrogen atom substituted with a phenyl group.

[0050] [a, *] In formula (2), a represents the bonding position with formula (1). In formula (3), * represents the bonding position with formula (2).

[0051] D １ and D ２ From the viewpoint of the life of the organic EL device, it is preferable that D is a carbazolyl group represented by the general formula (2) or a benzochalcogenylcarbazolyl group which is a group in which the general formula (3) is bonded to the general formula (2). １ and D ２ is more preferably any one of the following groups, and is even more preferably a group that does not incorporate triazine or cyano.

[0052]

[0053] From another perspective, D１ and D ２ That is, the group represented by general formula (2) may have a structure in which the σ value of Hammett's law is negative. The σ value of Hammett's law is a constant that indicates that the relationship between the structure of a benzene derivative and its influence on reactivity and equilibrium is linear, and can be calculated by formula (A). Log(K Ｒ / K Ｈ ) = σ (A)

[0054] In formula (A), K Ｒ is the equilibrium constant of the substituted benzene, K Ｈ is the equilibrium constant of unsubstituted benzene (Chem. Rev. 1991, 91, 165). In the group represented by formula (2), the σ value is preferably −0.1 or less, and more preferably −0.5 or more and −0.1 or less.

[0055] R １ ~R ２ , or R １ ~R ２ In terms of sublimability, the substituent that may be possessed by the group is preferably a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, and more preferably any of the following groups: In the following formulae, * indicates a bonding position.

[0056]

[0057] R ３ ~R １６ , or R ３ ~R １６ In terms of sublimability, the substituent that may be possessed by the group is preferably a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, or a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms, and more preferably any of the following groups: In the following formulae, * indicates a bonding position.

[0058]

[0059] <Structural Features of the Compound> The organic compound of this embodiment has the following two features: (1) One of the ortho positions of the phenyl group relative to the bonding position with triazine is a hydrogen atom, which makes the compound highly stable. (2) The donor (e.g., D １ The bond angle between the carbazole and the acceptor (triazine) is twisted, resulting in a reverse intersystem crossing rate constant (k ＲＩＳＣ ) indicates a large value.

[0060] These features will be explained below.

[0061] (1) When one of the ortho positions of the phenyl group relative to the bonding position with triazine is a hydrogen atom, the stability of the compound is excellent. As a result of extensive research, the present inventors have found that when one of the ortho positions of the phenyl group relative to the bonding position with triazine is a hydrogen atom, the stability of the compound is excellent.

[0062] The stability of a compound can be determined by the neutral bond dissociation energy (BDE). The smaller the BDE (the larger the absolute value of BDE), the higher the stability of the compound. １ , D ２ , R １ , R ２ The following compounds 1 to 15 and comparative compounds 1 to 17, into which the following groups (where * indicates the bonding position) have been introduced, are used as examples.

[0063]

[0064]

[0065]

[0066] The BDE of the C-C bond represented by (a) in general formula (4) was calculated for Compounds 1 to 15 and Comparative Compounds 1 to 17, and the results are shown in Table 1. In addition, Table 1 also shows that compounds with particularly large separation between HOMO and LUMO are rated as L (large), compounds with large separation as M (medium), and compounds with small separation as S (small).

[0067]

[0068] Comparative compound 1 (compound A) has two ortho positions (Y, D) of benzene. １ ) is a bulky group (D ａ ), which causes distortion of the bond. As a result, as shown in Table 1, the absolute value of the BDE of the C-C bond is small at 4.58, and the stability of the compound is low.

[0069] On the other hand, Compound 1, which is the same as Comparative Compound 1 except that Y in General Formula (4) is a hydrogen atom, has a large absolute value of BDE of the C-C bond of 4.75, as shown in Table 1, and is a highly stable compound.

[0070] As shown in Table 1, it was found that the BDE of the organic compounds according to this embodiment (compounds 1 to 15) is smaller (greater absolute value) than that of the comparative compounds 1 to 3. This is thought to be because the organic compounds according to this embodiment have a hydrogen atom at one of the two ortho positions of benzene relative to the bonding position with triazine, which reduces the distortion of the bond. Furthermore, the BDE of the organic compounds according to this embodiment is smaller (greater absolute value) than that of the comparative compounds 13 to 14. The comparative compounds 13 to 14 have a hydrogen atom at one of the two ortho positions of benzene (Y, D). １ ) are both carbazolyl groups (D ａ ) and D ２ or R １ The above results show that the BDE can be reduced by introducing hydrogen into one of the ortho positions of the benzene relative to the bonding position with triazine.

[0071] In addition, as in the comparative compounds 15 and 17, R １ It was found that the introduction of a carbazolyl group (Da) into the phenyl group increased the BDE. This is thought to be because the carbazolyl group bonded to the phenyl group has a bulky structure, which makes the phenyl-triazine bond more likely to be distorted.

[0072] The neutral bond dissociation energy (BDE) of the C—C bond shown in (a) of general formula (4), which is an index of the stability of the compound, is preferably −4.7 eV or less.

[0073] (2) Donor (e.g., D １The bond angle between the carbazole and the acceptor (triazine) is twisted, resulting in a reverse intersystem crossing rate constant (k ＲＩＳＣ ) shows a large value. １ By increasing the bond angle between the carbazole and the acceptor (triazine), the HOMO-LUMO separation improves, and ΔE ＳＴ The reverse intersystem crossing rate constant (k ＲＩＳＣ ) is 6 × 10 at room temperature (25 °C). ５ s －１ The above is preferable.

[0074] In an excited state, the TADF material undergoes reverse intersystem crossing from the excited triplet state to the excited singlet state, and then emits 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 represented by the following formula (B):

[0075]

[0076] Here, A is the prefactor (≒SOC / ΔE ＳＴ ) and k Ｂ is the Boltzmann constant, T is the temperature, and ΔE ＳＴ is the formula (C). ＳＴ = 2J (C)

[0077] Here, J is the HOMO-LUMO overlap integral, where HOMO is the highest occupied molecular orbital and LUMO is the lowest unoccupied molecular orbital.

[0078] That is, ΔE ＳＴ The smaller is, the ＲＩＳＣ becomes larger. ΔE ＳＴ In order to reduce the HOMO-LUMO separation, it is necessary to increase the HOMO-LUMO separation. In order to increase the HOMO-LUMO separation, it is sufficient to increase the bond angle between the donor and the acceptor. Table 1 shows the magnitude of the HOMO-LUMO separation for Compounds 1 to 15 and Comparative Compounds 1 to 17. From Table 1, it can be seen that the organic compound according to this embodiment has a R １ , R ２ Since at least one of these is a substituent, R １ , R ２In general formula (1), R １ , R ２ This is thought to be because the bond angle between the donor and the acceptor becomes larger when at least one of the groups is a group other than a hydrogen atom or a deuterium atom.

[0079] 1A shows the HOMO orbital distribution of compound 1, and FIG. 1B shows the LUMO orbital distribution of compound 1. FIG. 2A shows the HOMO orbital distribution of comparative compound 4, and FIG. 2B shows the LUMO orbital distribution of comparative compound 4. With reference to FIGS. 1A, 1B, 2A, and 2B, it can be seen that the overlapping portion between the HOMO orbital distribution and the LUMO orbital distribution is larger in FIGS. 2A and 2B than in FIGS. 1A and 1B (arrows in FIG. 2A). In this way, the organic compound according to this embodiment has a LUMO orbital distribution similar to that of R １ or R ２ It is believed that the separation between the HOMO and the LUMO becomes large when at least one of the groups is a group other than a hydrogen atom or a deuterium atom.

[0080] In this embodiment, an organic compound represented by the general formula (1) is proposed as a material having both (1) and (2).

[0081] As a more preferred embodiment of this embodiment, the organic compound according to this embodiment preferably has the following characteristics.

[0082] (3) The TADF material has an organic compound with an SOC of 0.72 or more. In the excited state, the TADF material undergoes reverse intersystem crossing from the excited triplet state to the excited singlet state, and then emits 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 represented by the following formula (D).

[0083]

[0084] Here, H bar, k Ｂ is a constant, λ (Marcus reorganization energy) does not vary significantly among compounds, and the temperature T is constant. ＲＩＳＣ is proportional to the square of the SOC.

[0085] Here, the SOCs of compounds 1, 2, 3 and comparative compound 4 are calculated to be 1.05, 0.90, 1.05 and 0.71, respectively, and are preferably 0.72 or more, more preferably 0.80 or more, and even more preferably 0.90 or more.

[0086] <Specific Examples> Specific examples of the organic compound represented by general formula (1) are shown below, but the present invention is not limited to these.

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] (2) Organic Light-Emitting Element Next, the organic light-emitting element of this embodiment will be described. The organic light-emitting element of this embodiment has at least a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is an anode and the other is a cathode. In the organic light-emitting element of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has a light-emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, etc. Furthermore, the light-emitting layer may be a single layer or a laminate consisting of multiple layers.

[0095] In the organic light-emitting device of this embodiment, at least one of the organic compound layers contains the organic compound according to this embodiment. Specifically, the organic compound according to this embodiment is contained in any of the above-mentioned light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, hole / exciton blocking layer, electron transport layer, electron injection layer, etc. The organic compound according to this embodiment is preferably contained in the light-emitting layer.

[0096] 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).

[0097] 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.

[0098] 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, relative to 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, relative to 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, relative to the entire light-emitting layer.

[0099] 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, a device 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 emitting 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 device 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 emits green or red. Furthermore, the film formation method is performed by vapor deposition or coating film formation.

[0100] 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.

[0101] <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 be used together as needed. Examples of these compounds are listed below.

[0102] As the hole injection / transport material, a material with high hole mobility is preferred so that it can easily inject holes from the anode and transport the injected holes to the light-emitting layer. Furthermore, a material with a high glass transition temperature is preferred to suppress deterioration of film quality, such as crystallization, in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole injection / 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 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 of course, the present invention is not limited to these.

[0103]

[0104]

[0105] Among the hole transport materials listed above, HT16-HT18 can reduce the driving voltage when used in a 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 an 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 to these, for example, SiO ２ It is also possible to use an inorganic insulating layer such as silicon nitride (SiN) or an organic silicon polymer such as siloxane. A plurality of materials may be used in one organic compound layer.

[0106] Examples of light-emitting materials primarily involved in 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 preparing a light-emitting layer by a coating method, polymer compounds with luminescent properties are primarily used. This is because polymer compounds are highly amorphous and therefore less likely to crystallize than low-molecular-weight compounds. 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 the light-emitting material are shown below, but the light-emitting material is not limited to these.

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] 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.

[0114]

[0115]

[0116] 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, EM29-EM35 and EM40-EM43.

[0117] 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 usable as electron transport materials are listed below, but of course, are not limited to these.

[0118]

[0119]

[0120] The electron injection material can be arbitrarily selected from those that allow easy electron injection from the cathode, and is selected taking into consideration the balance with hole injection properties, etc. Organic compounds include n-type dopants and reducing dopants. Examples include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives. They can also be used in combination with the above-mentioned electron transport materials.

[0121] <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. The planarizing layer may be made of an acrylic resin, etc. The same applies when a planarizing layer is provided between the color filter and the microlens. Either the first electrode or the second electrode may be an anode, and the other may be a cathode.

[0122] [Substrate] Examples of the substrate include quartz, glass, silicon wafer, resin, and metal. Furthermore, the substrate may be provided with a switching element such as a transistor and wiring, and an insulating layer thereon. The insulating layer may be made of any material as long as it can form a contact hole so that wiring can be formed between the first electrode and the insulating layer, and can ensure insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0123] [Electrodes] A pair of electrodes can be used. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. It can also be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0124] The anode material should preferably have as large a work function as possible. Examples of such materials include simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, mixtures containing these metals, alloys of these metals, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and zinc indium oxide. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0125] 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.

[0126] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. The above materials can also function as a reflective film without functioning as an electrode. When used as a transparent electrode, transparent conductive oxide layers such as indium tin oxide (ITO) and indium zinc oxide can be used, but are not limited to these. Photolithography technology can be used to form the electrode.

[0127] 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.

[0128] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but DC and AC sputtering methods are more preferable because they provide good film coverage and make it easier to reduce resistance.

[0129] [Organic Compound Layer] The organic compound layer may be formed as a single layer or as multiple layers. When multiple layers are present, they may be called hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, or electron injection layer depending on their functions. The organic compound layer is mainly composed of organic compounds but may also contain inorganic atoms or inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be disposed between the first electrode and the second electrode, or may be disposed in contact with the first electrode and the second electrode.

[0130] 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.

[0131] 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 suitable for producing a large-area organic light-emitting device.

[0132] 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.

[0133] 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.

[0134] 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.

[0135] 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.

[0136] The thickness of each layer in the organic light-emitting device is preferably 1 nm to 10 μm in general, and in particular, the thickness of the light-emitting layer of the organic compound layer is preferably 10 nm to 100 nm in order to obtain effective light-emitting characteristics.

[0137] [Protective Layer] A protective layer may be provided on the second electrode. For example, by adhering glass with a moisture absorbent to the second electrode, the intrusion of water and other contaminants into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the second electrode to reduce the intrusion of water and other contaminants into the organic compound layer. For example, after forming the second electrode, the second electrode may be transferred to another chamber without breaking the vacuum, and a 2 μm-thick silicon nitride film may be formed by CVD to serve as a protective layer. A protective layer may be provided using atomic layer deposition (ALD) after the CVD film formation. The material of the film formed by ALD is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed on the film formed by ALD by CVD. The film formed by ALD may have a thickness smaller than that of the film formed by CVD. Specifically, the thickness may be 50% or less, or even 10% or less.

[0138] [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.

[0139] [Planarization Layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing the unevenness of the underlying layer. It may also be called a material resin layer without limiting its purpose. The planarization layer may be composed of an organic compound, and may be either a low molecular weight or a high molecular weight, but is preferably a high molecular weight.

[0140] 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.

[0141] [Microlens] The organic light-emitting element may have an optical component such as a microlens on its light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be used to increase the amount of light extracted from the organic light-emitting element and to control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be determined in the same way in any cross-sectional view. In other words, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the semicircle is the vertex of the microlens.

[0142] 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.

[0143] [Counter Substrate] An counter substrate may be provided on the planarization layer. The counter substrate is called a counter substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is defined as a first substrate, the counter substrate may be a second substrate.

[0144] [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.

[0145] The light-emitting device has a display region and a peripheral region arranged around the display region. The display region has a pixel circuit, and the peripheral region has a display control circuit. The mobility of a transistor constituting the pixel circuit may be smaller than the mobility of a transistor constituting the display control circuit. The slope of the current-voltage characteristics of the transistor constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistor constituting the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics. The transistor constituting the pixel circuit is a transistor connected to a light-emitting element, such as a first light-emitting element.

[0146] [Pixel] An organic light-emitting device having an organic light-emitting element may have a plurality of pixels. Each pixel has sub-pixels that emit different colors. The sub-pixels may each emit RGB light, for example.

[0147] 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.

[0148] 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.

[0149] The organic light-emitting device according to this embodiment can be used as a component of a display device or a lighting device. Other applications include an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, and a light-emitting device having a white light source and a color filter.

[0150] The display device may be an image information processing device having an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., an information processing unit that processes the input information, and displays the input image on a display unit. The display device has a plurality of pixels, and at least one of the plurality of pixels may have the organic light-emitting element of this embodiment and an active element such as a transistor connected to the organic light-emitting element. In this case, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate. The image display device has an input unit for inputting image information and a display unit for outputting an image, and the display unit has the display device of this embodiment.

[0151] 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.

[0152] Next, the display device according to this embodiment will be described with reference to the drawings. Figures 3A and 3B are cross-sectional schematic diagrams showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin film transistor (TFT).

[0153] 3A 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 edge of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode serving as a second electrode 5, a protective layer 6, and a color filter 7.

[0154] 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).

[0155] The insulating layer 3 is also called a bank or a pixel separation film. It covers the edges of the first electrode 2 and is disposed to surround the first electrode 2. The portion where the insulating layer 3 is not disposed is in contact with the organic compound layer 4 and becomes a light-emitting region.

[0156] 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 .

[0157] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0158] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 is illustrated as being one layer, it may be a multi-layer structure, with each layer being an inorganic compound layer and an organic compound layer.

[0159] 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.

[0160] The display device 100 in Fig. 3B 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.

[0161] The electrical connection method 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 mode shown in Fig. 3B . 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.

[0162] 3B, 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.

[0163] In the display device 100 of FIG. 3B, transistors are used as switching elements, but other switching elements such as MIM elements may be used instead.

[0164] Further, the transistor used in the display device 100 of FIG. 3B is not limited to a thin film transistor having an active layer on the insulating surface of the substrate, and a transistor using a single crystal silicon wafer may also be used. Examples of the active layer include non-single crystal silicon such as single crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Note that the thin film transistor is also called a TFT element.

[0165] The transistor included in the display device 100 of FIG. 3B may be formed in a substrate such as a Si substrate. Here, forming in the substrate means manufacturing a transistor by processing the substrate itself such as a Si substrate. That is, having a transistor in the substrate can also be regarded as the substrate and the transistor being integrally formed.

[0166] The organic light emitting element according to the present embodiment is controlled in light emission luminance by a TFT which is an example of a switching element, and an image can be displayed by the respective light emission luminances by providing a plurality of organic light emitting elements in a plane. Note that the switching element according to the present embodiment is not limited to a TFT, and may be a transistor formed of low temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also mean "in the substrate". Whether to provide a transistor in the substrate or use a TFT is selected according to the size of the display portion. For example, if the size is about 0.5 inches, it is preferable to provide an organic light emitting element on a Si substrate.

[0167] 4 is a schematic diagram showing an example of a display device according to this embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The 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.

[0168] 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.

[0169] 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.

[0170] 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.

[0171] 5A is a schematic diagram illustrating an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may include a display device according to this embodiment. In this case, the display device may display not only an image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject is moving, the possibility that the subject will be blocked by an obstruction, and the like.

[0172] 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.

[0173] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses, which form an image on an imaging element housed in a housing 1104. The focus of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may also be called a photoelectric conversion device. Instead of sequentially capturing images, the photoelectric conversion device may include an imaging method that detects the difference from the previous image, or a method of cutting out an image that is constantly being recorded.

[0174] FIG. 5B 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.

[0175] 6A and 6B are schematic diagrams illustrating an example of a display device according to this embodiment. FIG. 6A 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. 6A . 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.

[0176] FIG. 6B is a schematic diagram illustrating another example of a display device according to the present embodiment. The display device 1310 in FIG. 6B is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include a light-emitting element according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be a single, seamless display device. The first display unit 1311 and the second display unit 1312 can be separated by the bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may display a single image.

[0177] 7A is a schematic diagram illustrating an example of an illumination device according to this embodiment. The illumination device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusion unit 1405. The light source 1402 may include an organic light-emitting element according to this embodiment. The optical filter 1404 may be a filter that improves the color rendering of the light source. The light diffusion unit 1405 can effectively diffuse light from the light source, such as for illumination, and deliver the light over a wide area. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the illumination device. If necessary, a cover may be provided on the outermost surface.

[0178] The lighting device is, for example, a device for illuminating a room. The lighting device may emit white, daylight white, or any other color from blue to red. It may have a dimming circuit for dimming them or a color tuning circuit for tuning the emitted color. The lighting device may have the organic light-emitting element of this embodiment and a power supply circuit connected thereto. The power supply circuit is a circuit for converting AC voltage to DC voltage. The lighting device may have an inverter circuit. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device may have a color filter.

[0179] 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.

[0180] 7B 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.

[0181] The tail lamp 1501 may include the organic light-emitting element according to this embodiment. The tail lamp 1501 may include a protective member for protecting the organic light-emitting element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0182] The automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display as long as it is not a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, constituent materials of the electrodes and the like of the organic light-emitting element are made of transparent materials.

[0183] 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.

[0184] 8A and 8B , application examples of the display devices according to the above-described embodiments will be described. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, HMDs, and smart contact lenses. The image capturing and display device used in such application examples includes an image capturing device capable of photoelectrically converting visible light and a display device capable of emitting visible light.

[0185] Fig. 8A is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using Fig. 8A, eyeglasses 1600 (smart glasses) according to one application example will be described. An imaging device 1602 such as a CMOS sensor or SPAD is provided on the front side of lenses 1601 of the eyeglasses 1600. Furthermore, a display device according to any of the above-described embodiments is provided on the back side of the lenses 1601.

[0186] 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.

[0187] FIG. 8B is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 8B , 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. 8A 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.

[0188] The control device 1612 may include a gaze detection unit that detects the wearer's gaze. The gaze detection may use infrared light. The infrared light emitter emits infrared light toward the eyeball of the user gazing at the display image. An imaging unit with a light-receiving element detects the reflected infrared light from the eyeball, thereby obtaining a captured image of the eyeball. By including a reduction unit that reduces light from the infrared light emitter to the display unit in a planar view, degradation of image quality is reduced. The user's gaze toward the displayed image is detected from the captured image of the eyeball obtained by capturing infrared light. Any known method can be applied to gaze detection using the captured image of the eyeball. As an example, a gaze detection method based on a Purkinje image formed by reflection of irradiated light on the cornea can be used. More specifically, gaze detection processing based on the pupil-corneal reflex method is performed. Using the pupil-corneal reflex method, a gaze vector representing the orientation (rotation angle) of the eyeball is calculated based on the image of the pupil and the Purkinje image included in the captured image of the eyeball, thereby detecting the user's gaze.

[0189] 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.

[0190] 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.

[0191] Note that AI may be used to determine the first field of view area and the area with high priority. The AI ​​may be a model configured to estimate the angle of gaze and the distance to an object in the line of sight from the image of the eyeball, using as training data an image of the eyeball and the direction in which the eyeball in the image was actually looking. The AI ​​program may be included in the display device, the imaging device, or an external device. If included in the external device, it is transmitted to the display device via communication.

[0192] 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.

[0193] 9A and 9B are schematic diagrams of an HMD (head-mounted display) 2301 as a display device according to one embodiment of the present invention. FIG. 9A is a schematic diagram showing a head-mounted display and an observer wearing the display. The HMD 2301 is worn on the observer's head. Reference numeral 2302 denotes the observer's right eye, and reference numeral 2303 denotes the observer's left eye. Display lenses 2304 and 2305 constitute the right-eye eyepiece optical system OR1, and display lenses 2306 and 2307 constitute the left-eye eyepiece optical system OL1. Each eyepiece optical system is a coaxial optical system composed of multiple (two) display lenses. The observer's right eye 2302 is positioned at the exit pupil ER1 of the right-eye eyepiece optical system OR1, and the observer's left eye 2303 is positioned at the exit pupil EL1 of the left-eye eyepiece optical system OL1. The exit pupil ER1 is located a distance E1 away from the right-eye eyepiece optical system OR1. Similarly, the exit pupil EL1 is located at a distance E1 from the eyepiece optical system OL1 for the left eye. Optical films 2314 for lens protection, light collection, etc. are provided on the surfaces of the eyepiece optical system OR1 for the right eye (the surface facing the right eye 2302) and the eyepiece optical system OL1 for the left eye (the surface facing the left eye 2303).

[0194] Reference numerals 2308 and 2309 denote display devices for the right and left eyes, respectively. These display devices may be the display devices according to embodiment 1. FIG. 9B is a schematic diagram showing an example in which a display device according to an embodiment of the present invention is connected to an external device, showing the appearance of an HMD 2301 and a personal computer 2350 connected thereto. Each display device displays a display image (original image) corresponding to an image signal output from the personal computer 2350. In this embodiment, the display devices are connected by wire, but may also be connected wirelessly. Furthermore, the HMD 2301 may be a device that has an image processing device built in and operates as a standalone device.

[0195] The eyepiece optical systems OR1 and OL1 guide light from the display devices 2308 and 2309 to the exit pupils ER1 and EL1, respectively, to project enlarged virtual images of the displayed images onto the observer's right eye 2302 and left eye 2303. This allows the observer to observe the display images (virtual images of the images) displayed on the display devices 2308 and 2309 through the eyepiece optical systems OR1 and OL1.

[0196] Although not shown, the HMD 2301 may have a control device. The control device functions as a power source that supplies power to the display devices 2308 and 2309, and also controls the operations of the display devices 2308 and 2309.

[0197] 10A is a schematic diagram showing an example of an image forming apparatus according to an embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 includes 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.

[0198] 10B and 10C 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, representing the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis about which the photoconductor 27 rotates. This direction can also be referred to as the long axis direction of the photoconductor 27. FIG. 10B shows a configuration in which the light-emitting units 36 are arranged along the long axis of the photoconductor 27. FIG. 10C shows a configuration different from that shown in FIG. 10B, in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are arranged at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged at intervals. In the second column, the light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. In other words, multiple light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in FIG. 10C can also be described as a grid arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0199] 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.

[0200] (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.

[0201] 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.

[0202] 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 an appropriate 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.

[0203] 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.

[0204] The concentration of the organic compound of this embodiment in the ink composition is from 0.05% by mass to 50% by mass, preferably from 0.05% by mass to 30% by mass, more preferably from 0.05% by mass to 20% by mass, and even more preferably from 0.1% by mass to 5% by mass, based on the total mass of the composition.

[0205] 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.

[0206] Examples will be described below, but the present invention is not limited to these examples.

[0207] Example 1 (Synthesis of Example Compounds and Comparative Example Compounds) (1) Synthesis of Example Compounds 1, 3, 4, and 6 (Compounds 1, 2, 4, and 5 of Chemical Formula 13)

[0208]

[0209] <Synthesis of Intermediate 1> Under a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (2.00 g), phenylboronic acid (1.03 g), 2M aqueous sodium carbonate solution (11.0 mL), tetrakis(triphenylphosphine)palladium(0) (553 mg) and toluene (37 mL) were added, and the mixture was stirred at 80°C for 11 hours. Ethyl acetate was added to the reaction mixture, and the mixture was extracted with ethyl acetate and then dried over sodium sulfate. The solvent was removed, and the residue was purified by column chromatography (hexane) to obtain Intermediate 1 (1.00 g). GC-MS [267.9, M ＋ , calcd. 268.0]

[0210] <Synthesis of Intermediate 3> Intermediate 1 (1.60 g), potassium acetate (KOAc, 1.75 g), Bis(pinacolato)diboron (1.81 g), [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride (Pd(dppf)Cl ２ To the resulting mixture (158 mg) was added 1,4-dioxane (12 mL) under a nitrogen atmosphere, and the mixture was stirred at 110° C. for 4 hours to obtain a reaction mixture containing Intermediate 2.

[0211] After cooling to room temperature, the reaction mixture was added with 2-chloro-4,6-diphenyl-1,3,5-triazine (3.18 g), 2 M aqueous sodium carbonate solution (11.0 mL), Bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh ３ ) ２ Cl ２ , 209 mg) and toluene (15 mL) were added, and the mixture was stirred at 80°C for 11 hours. Ethyl acetate was added to the reaction mixture, and the mixture was extracted with ethyl acetate and then dried over sodium sulfate. The solvent was removed, and the residue was purified by column chromatography (hexane / chloroform) to obtain Intermediate 3 (1.21 g). GC-MS [421.1, M ＋ , calcd. 421.1]

[0212] <Synthesis of Intermediate 4> Palladium(II) acetate (16 mg), Intermediate 3 (0.33 g), bromobenzene (0.62 g), cesium carbonate (0.89 g), 2-ethylhexanoic acid (1.56 mmol, 0.23 g), and tricyclohexylphosphine (0.06 g) were added to xylene (16 mL) under a nitrogen atmosphere, and the mixture was stirred at 130°C for 11 hours. Chloroform was added to the reaction mixture, and the mixture was extracted with chloroform, dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by recycled preparative GPC (JAI-GEL, chloroform) to obtain Intermediate 4 (0.10 g). GC-MS [497.1, M ＋ , calcd. 497.2]

[0213] <Synthesis of Example Compound 1 (Compound 1 of Chemical Formula 13)> DMF (1.6 mL) was added to Intermediate 4 (100 mg), 9H-carbazole (218 mg), and cesium carbonate (464 mg) under a nitrogen atmosphere, and the mixture was stirred at 150°C for 11 hours. After returning to room temperature, water and methanol were added to the reaction solution, and the suspension was filtered. The residue was purified by recycled preparative GPC (JAI-GEL, chloroform) to obtain Example Compound 1 (120 mg) as a pale yellow solid. GC-MS [792.1, M ＋ H ＋ , calcd. 792.3]

[0214] <Synthesis of Example Compound 3 (Compound 2 of Chemical Formula 13)> DMF (3.2 mL) was added to Intermediate 3 (200 mg), 9H-carbazole (254 mg), and cesium carbonate (774 mg) under a nitrogen atmosphere, and the mixture was stirred at 110°C for 11 hours. After returning to room temperature, water and methanol were added to the reaction solution, and the suspension was filtered. The residue was purified by silica gel column chromatography (hexane / dichloromethane), and Example Compound 3 (101 mg) was obtained as a pale yellow solid. GC-MS [716.7, M ＋ H ＋ , calcd. 716.5]

[0215] <Synthesis of Example Compounds 4 and 6 (Compounds 4 and 5 of Chemical Formula 13)> Example Compounds 4 and 6 were obtained from Intermediate 4 and Intermediate 3, respectively, using 9H-carbazole-3-carbonitrile in the same manner as Example Compounds 1 and 3.

[0216] (2) Synthesis of Example Compounds 2 and 5 (Compounds 3 and 6 of Chemical Formula 13) and Comparative Compounds 1 and 2 (Comparative Compounds 4 and 6 of Chemical Formula 13)

[0217]

[0218] <Synthesis of Intermediates 6 and 7> Intermediates 6 and 7 were obtained in the same manner as in the synthesis of Intermediates 3 and 4, using 1-bromo-2,4-difluorobenzene.

[0219] <Synthesis of Example Compounds 2 and 5 (Compounds 3 and 6 of Chemical Formula 13)> Example Compounds 2 and 5 were obtained from Intermediate 7 in the same manner as in the synthesis of Example Compounds 1 and 4, respectively.

[0220] <Synthesis of Comparative Compounds 1 and 2 (Comparative Compounds 4 and 6 of Chemical Formula 13)> Comparative Compounds 1 and 2 were obtained from Intermediate 6 in the same manner as in Example Compounds 3 and 6, respectively.

[0221] (3) Synthesis of Example Compounds 7 and 8

[0222]

[0223] <Synthesis of Intermediate 8> Under a nitrogen atmosphere, 1,5-Dibromo-2,4-difluoro-3-methylbenzene (4.09 g), phenylboronic acid (1.69 g), 2M aqueous sodium carbonate solution (36.0 mL), tetrakis(triphenylphosphine)palladium(0) (221 mg) and toluene (75 mL) were added, and the mixture was stirred at 80°C for 11 hours. Chloroform was added to the reaction mixture, and the mixture was extracted with chloroform and then dried over magnesium sulfate. The solvent was removed, and the residue was purified by column chromatography (hexane) to obtain Intermediate 8 (1.81 g). GC-MS [281.9, M ＋ , calcd. 281.9]

[0224] <Synthesis of Intermediate 10> Intermediate 8 (1.80 g), potassium acetate (KOAc, 1.92 g), Bis(pinacolato)diboron (0.96 g), [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride (Pd(dppf)Cl ２ 1,4-Dioxane (40 mL) was added to the resulting mixture (101 mg) under a nitrogen atmosphere, and the mixture was stirred at 110° C. for 11 hours to obtain a reaction mixture containing Intermediate 9.

[0225] After cooling to room temperature, 2-chloro-4,6-diphenyl-1,3,5-triazine (2.65 g), 2M aqueous sodium carbonate solution (11.0 mL), and tetrakis(triphenylphosphine)palladium(0) (113 mg) were added to the reaction mixture, and the mixture was stirred at 85°C for 11 hours. Toluene was added to the reaction mixture, and the mixture was extracted with toluene and then dried over sodium sulfate. The solvent was removed, and the residue was purified by column chromatography (hexane / chloroform) to obtain intermediate 10 (0.70 g). GC-MS [435.1, M ＋ , calcd. 435.1]

[0226] <Synthesis of Example Compound 7> DMF (6.0 mL) was added to Intermediate 10 (328 mg), 9H-carbazole (312 mg), and cesium carbonate (793 mg) under a nitrogen atmosphere, and the mixture was stirred at 140°C for 11 hours. After returning to room temperature, water and methanol were added to the reaction solution, and the suspension was filtered. The residue was purified by silica gel column chromatography (hexane / dichloromethane), and Example Compound 7 (301 mg) was obtained as a pale yellow solid. GC-MS [730.2, M+H ＋ , calcd. 730.2]

[0227] <Synthesis of Example Compound 8> DMF (2.0 mL) was added to intermediate 10 (151 mg), 5H-benzofuro[3,2-c]carbazole (190 mg), and cesium carbonate (230 mg) under a nitrogen atmosphere, and the mixture was stirred at 140°C for 11 hours. After returning to room temperature, water and methanol were added to the reaction solution, and the suspension was filtered. The residue was purified by silica gel column chromatography (hexane / dichloromethane), and Example Compound 8 (210 mg) was obtained as a pale yellow solid. MALDI-MS [909.3, M+H ＋ , calcd. 909.3]

[0228] Example 2 (Optical Property Spectra in Solution) Example Compounds 1 to 8 and Comparative Compounds 1 and 2 were mixed for 10 minutes. －５ The PL spectrum of the adjusted solution, fluorescence lifetime measurement, and fluorescence quantum yield measurement revealed that k ＲＩＳＣ [10 ５ s －１ ] was measured. ＲＩＳＣ The values ​​are those at room temperature (25° C.). The results are shown in Table 2.

[0229]

[0230] From Table 2, it was found that Example Compounds 1 to 6 have better HOMO-LUMO separation than the Comparative Example Compounds (see Table 1), and therefore have faster RISC.

[0231] <<Configurations Included>> The disclosure of this embodiment includes the following configurations.

[0232] (Configuration 1) An organic compound represented by general formula (1): １ and R ２ are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group not containing a nitrogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group. １ and R ２ At least one of R is a substituent. ３ and R ４are each independently selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, and a cyano group. １ and D ２ are each independently selected from the group represented by general formula (2). ５ ~R １２ 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 silyl group, and a cyano group. ９ ~R １２ In general formula (3), two adjacent groups may be substituted with a group represented by general formula (3). １３ ~R １６ 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 silyl group, and a cyano group. X is selected from 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), a indicates the bonding position with general formula (1). In general formula (3), * indicates the bonding position with general formula (2).

[0233] (Configuration 2) The organic compound according to configuration 1, wherein the group represented by the general formula (2) has a negative σ value according to Hammett's rule.

[0234] (Configuration 3) The organic compound according to Configuration 2, wherein the σ value of the Hammett rule is −0.1 or less.

[0235] (Configuration 4) The organic compound according to Configuration 3, wherein the σ value of the Hammett rule is −0.5 or more and −0.1 or less.

[0236] (Configuration 5) R ５ ~R １２ are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms, and a cyano group.

[0237] (Configuration 6) The above D １ and D ２ is any one of the groups shown in Chemical Formula 8.

[0238] (Configuration 7) The R ３ ~R １６ , or the R ３ ~R １６ 7. The organic compound according to any one of structures 1 to 6, wherein the substituent which may be possessed by is any one of the groups shown in Chemical Formula 10.

[0239] (Configuration 8) R １ and R ２ are each independently selected from a hydrogen atom, a deuterium atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, an unsubstituted dibenzochalcogenyl group, and an unsubstituted triphenylsilyl group.

[0240] (Configuration 9) R １ , R ２ and at least one of the above is a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, or a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms and not containing a nitrogen atom.

[0241] (Configuration 10) R ７ , R １０ 10. The organic compound according to any one of structures 1 to 9, wherein at least one of the following is a substituent.

[0242] (Configuration 11) R ７ , R１０ 11. The organic compound according to claim 10, wherein at least one of the above is a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms, or a cyano group.

[0243] (Configuration 12) R ９ and R １０ 12. The organic compound according to any one of structures 1 to 11, wherein the group represented by general formula (3) is substituted with

[0244] (Structure 13) 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, wherein at least one layer of the organic compound layer contains the organic compound according to any one of Structures 1 to 12.

[0245] (Configuration 14) The organic light-emitting device according to Configuration 13, wherein the layer containing the organic compound is a light-emitting layer.

[0246] (Configuration 15) The organic light-emitting device according to Configuration 14, wherein the light-emitting layer contains a second organic compound different from the organic compound.

[0247] (Configuration 16) The organic light-emitting device according to Configuration 15, 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.

[0248] (Configuration 17) The organic light-emitting device according to Configuration 16, 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.

[0249] (Configuration 18) The organic light-emitting device according to any one of Configurations 15 to 17, wherein the light-emitting layer contains a third organic compound different from both the organic compound and the second organic compound.

[0250] (Configuration 19) The organic light-emitting device according to Configuration 18, 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.

[0251] (Configuration 20) The organic light-emitting device according to Configuration 19, 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.

[0252] (Configuration 21) An ink composition comprising the organic compound according to any one of Configurations 1 to 12.

[0253] (Configuration 22) A display device having a plurality of pixels, at least one of the plurality of pixels having the organic light-emitting element according to any one of Configurations 13 to 20 and a transistor connected to the organic light-emitting element.

[0254] (Configuration 23) A photoelectric conversion device comprising: an optical unit having a plurality of lenses; an image sensor that receives light that has passed through the optical unit; and a display unit that displays an image captured by the image sensor, wherein the display unit has the organic light-emitting element according to any one of Configurations 13 to 20.

[0255] (Configuration 24) An electronic device comprising: a display unit having the organic light-emitting element according to any one of Configurations 13 to 20; a housing in which the display unit is provided; and a communication unit provided in the housing and communicating with an external device.

[0256] (Configuration 25) A lighting device comprising: a light source having the organic light-emitting element according to any one of Configurations 13 to 20; and a light diffusion section or an optical filter that transmits light emitted by the light source.

[0257] (Configuration 26) A moving body comprising: a lighting fixture having the organic light-emitting element according to any one of Configurations 13 to 20; and a vehicle on which the lighting fixture is provided.

[0258] (Configuration 27) An exposure light source for an electrophotographic image forming apparatus, comprising the organic light-emitting device according to any one of Configurations 13 to 20.

[0259] The present invention is not limited to the above-described embodiments, and various modifications and variations can be made without departing from the spirit and scope of the present invention. Therefore, the following claims are appended to apprise the public of the scope of the present invention.

[0260] This application claims priority based on Japanese Patent Application No. 2024-104865 filed on June 28, 2024 and Japanese Patent Application No. 2025-088924 filed on May 28, 2025, the entire contents of which are incorporated herein by reference.

[0261] REFERENCE SIGNS LIST 1 Interlayer insulating layer 2 First electrode 3 Insulating layer 4 Organic compound layer 5 Second electrode 6 Protective layer 7 Color filter 10 Subpixel 11 Substrate 12 Insulating layer 13 Gate electrode 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrode 18 TFT 19 Insulating film 20 Contact hole 21 Anode 22 Organic compound layer 23 Cathode 24 First protective layer 25 Second protective layer 26 Organic light-emitting element 100 Display device

Claims

1. An organic compound represented by the following general formula (1): In general formula (1), R １ and R ２ are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group not containing a nitrogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted silyl group. １ and R ２ At least one of R is a substituent. ３ and R ４ are each independently selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, and a cyano group. １ and D ２ are each independently selected from groups represented by the following general formula (2): In general formula (2), R ５ ~R １２ 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 silyl group, and a cyano group. ９ ~R １２ Any two adjacent ones of these may be substituted with a group represented by the following general formula (3). In general formula (3), R １３ ~R １６ 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 silyl group, and a cyano group. X is selected from 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), a indicates the bonding position with general formula (1). In general formula (3), * indicates the bonding position with general formula (2).

2. The organic compound according to claim 1, wherein the σ value of the group represented by the general formula (2) in Hammett's law is negative.

3. The organic compound according to claim 2, wherein the σ value of the Hammett's rule is −0.1 or less.

4. The organic compound according to claim 3, wherein the σ value of the Hammett's rule is −0.5 or more and −0.1 or less.

5. R ５ ~R １２ are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms, and a cyano group.

6. The above D １ and D ２ The organic compound according to claim 5, characterized in that:

7. The above R ３ ~R １６ , or the R ３ ~R １６ 5. The organic compound according to claim 1, wherein the substituent which may be present is any one of the following groups: In the above formula, * indicates the bond position.

8. R １ and R ２ are each independently selected from a hydrogen atom, a deuterium atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, an unsubstituted dibenzochalcogenyl group, and an unsubstituted triphenylsilyl group.

9. R １ , R ２ 5. The organic compound according to claim 1 , wherein at least one of the above is a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, or a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms and not containing a nitrogen atom.

10. R ７ , R １０ 5. The organic compound according to claim 1, wherein at least one of the groups is a substituent.

11. R ７ , R １０ 11. The organic compound according to claim 10, wherein at least one of the above is a substituted or unsubstituted alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms, a substituted or unsubstituted heterocyclic group having from 6 to 12 carbon atoms, or a cyano group.

12. R ９ and R １０ 5. The organic compound according to claim 1, wherein the group represented by the general formula (3) is substituted with 13. 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, wherein at least one of the organic compound layers contains an organic compound according to any one of claims 1 to 4.

14. The organic light-emitting device according to claim 13, wherein the layer containing the organic compound is a light-emitting layer.

15. The organic light-emitting device according to claim 14, wherein the light-emitting layer contains a second organic compound different from the organic compound.

16. The organic light-emitting device according to claim 15, 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.

17. The organic light-emitting device according to claim 16, 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.

18. The organic light-emitting device according to claim 15, wherein the light-emitting layer contains a third organic compound different from both the organic compound and the second organic compound.

19. The organic light-emitting device according to claim 18, 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.

20. The organic light-emitting element according to claim 19, characterized in that 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.

21. An ink composition comprising the organic compound according to any one of claims 1 to 4.

22. A display device having a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to claim 13 and a transistor connected to the organic light-emitting element.

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

24. An electronic device comprising: a display unit having the organic light-emitting element according to claim 13; a housing in which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

25. A lighting device comprising a light source having the organic light-emitting element according to claim 13, and a light diffusion section or optical filter that transmits light emitted by the light source.

26. A moving object comprising a lighting fixture having the organic light-emitting element according to claim 13 and a vehicle on which the lighting fixture is mounted.

27. An exposure light source for an electrophotographic image forming apparatus, comprising the organic light emitting element according to claim 13.

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