Organic compound and organic light emitting element using the same

Abstract

To provide an organic compound having a high oscillator strength.SOLUTION: The present invention provides an organic compound represented by general formulae (1) to (3). In general formulae (1) to (3), A1, A2, X1, and X2 are each independently selected from the group consisting of a chalcogen atom, NR10, and CR11R12. R10 to R12 are a hydrogen atom or a substituent. Z is a direct bond or a divalent linking group. a to d are each an integer of 0 to 4 inclusive. However, organic compounds in which A1, A2, X1, and X2 in general formula (3) are sulfur atoms are excluded.SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] An organic light-emitting device (hereinafter sometimes referred to as an "organic electroluminescence device" or an "organic EL device") is an electronic device having a pair of electrodes and an organic compound layer disposed between these electrodes. By injecting electrons and holes (holes) from these pair of electrodes into the organic compound layer, excitons of a light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting device emits light.

[0003] By the way, the creation of compounds suitable for organic light-emitting devices has been actively carried out until now. Compound 1-a is described in Patent Document 1, and compound 1-b is described in Patent Document 2.

[0004]

Chemical Formula

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0006] However, the organic compound described in Patent Document 1 has a low oscillator strength as a light-emitting material, and an organic compound having a higher oscillator strength has been desired.

[0007] The present invention has been made in view of the above problems, and an object thereof is to provide an organic compound exhibiting high oscillator strength.

Means for Solving the Problems

[0008] The organic compound according to the present invention is characterized by being represented by general formulas (1) to (3).

[0009]

Chemical formula

[0010] In general formulas (1) to (3), R 1 to R 4 are each independently selected from the group consisting of 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. R 5 is 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, or a cyano group. A 1 , A 2 、 X 1 、 and X 2 are each independently selected from the group consisting of a chalcogen atom, NR 10 , and CR 11 R 12 . R 10 to R 12is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted 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. Z is a direct bond, a chalcogen atom, a substituted or unsubstituted methylene group, a substituted or unsubstituted silylene group, an imino group substituted with an aryl group, or a substituted or unsubstituted aryl group. a to d are each an integer of 0 or more and 4 or less. However, in General Formula (2), a and b are each an integer of 0 or more and 3 or less. A plurality of R 1 may be the same as or different from each other. A plurality of R 2 may be the same as or different from each other. A plurality of R 3 may be the same as or different from each other. A plurality of R 4 may be the same as or different from each other. [[Effect of the Invention]]

[0011] According to the present invention, an organic compound having a high oscillator strength can be provided. [[Brief Description of the Drawings]]

[0012]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Embodiments for Carrying Out the Invention

[0013] In the present specification, examples of the halogen atom include, but are not limited to, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.

[0014] Examples of the chalcogen atom include, but are not limited to, an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, etc.

[0015] The alkyl group may have 1 to 40 carbon atoms, may have 1 to 20 carbon atoms, or may have 1 to 10 carbon atoms. Specifically, examples include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a tertiary pentyl group, a 3-methylpentan-3-yl group, a 1-adamantyl group, a 2-adamantyl group, etc.

[0016] The aryl group may have 6 to 20 carbon atoms, may have 6 to 18 carbon atoms, or may have 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, phenyl group, naphthyl group, indenyl group, biphenyl group, terphenyl group, fluorenyl group, phenanthryl group, triphenylenyl group, pyrenyl group, anthranyl group, perylenyl group, chrysenyl group, fluoranthenyl group, etc.

[0017] The heterocyclic group may have 3 to 24 carbon atoms, may have 3 to 18 carbon atoms, or may have 3 to 12 carbon atoms. Specifically, examples include, but are not limited to, pyridyl group, pyrimidyl group, pyrazyl group, triazyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, carbazolyl group, acridinyl group, phenanthrolyl group, etc.

[0018] 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 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, N-methylamino group, N-ethylamino group, N,N-dimethylamino group, N,N-diethylamino group, N-methyl-N-ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N,N-dibenzylamino group, anilino group, N,N-diphenylamino group, N,N-dinaphthylamino group, N,N-difluorenylamino group, N-phenyl-N-tolylamino group, N,N-ditolylamino group, N-methyl-N-phenylamino group, N,N-dianisolyamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tert-butylphenyl)amino group, N-phenyl-N-(4-trifluoromethylphenyl)amino group, N-piperidyl group, etc.

[0019] The alkoxy group may have 1 to 40 carbon atoms, may have 1 to 20 carbon atoms, or may have 1 to 10 carbon atoms. Specifically, examples include, but are not limited to, methoxy group, ethoxy group, propoxy group, 2-ethyl-octyloxy group, benzyloxy group, etc.

[0020] Specific examples of the aryloxy group include, but are not limited to, phenoxy group, etc.

[0021] Specific examples of the heteroaryloxy group include, but are not limited to, thienyloxy group, etc.

[0022] Specific examples of the silyl group include, but are not limited to, trimethylsilyl group, triphenylsilyl group, etc.

[0023] Substituents that the above alkyl group, alkoxy group, amino group, aryloxy group, silyl group, aryl group, and heterocyclic group may further have include 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, cyano group, etc., but are not limited to these.

[0024] In addition, in this specification, the basic skeleton refers to the skeleton in which a to d are 0, R 5 is a hydrogen atom, and A 1 and A 2 are NR 10 or CR 11 R 12 and R 10 to R 12 are hydrogen atoms.

[0025] (1) Organic compound First, the organic compound according to the present invention will be described.

[0026] The organic compound according to the present invention is characterized by being represented by general formulas (1) to (3).

[0027]

Chemical formula

[0028] In general formulas (1) to (3), R 1 to R 4 are each independently selected from the group consisting of 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. R 5 is 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, or a cyano group.

[0029] In general formulas (1) to (3), R 1 to R 4may each independently be an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, an amino group having an aryl group having 6 to 12 carbon atoms, or a cyano group, may be an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, or a cyano group, may be an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, or a cyano group, may be a hydrogen atom, a methyl group, an iso-propyl group, a tert-butyl group, a diarylamine group, a phenyl group, a phenyl group having an alkyl group as a substituent, a biphenyl group, or a carbazolyl group, and may be a methyl group or a tert-butyl group.

[0030] In General Formulas (1) to (3), R 5 may be a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, an amino group having an aryl group having 6 to 12 carbon atoms, or a cyano group, may be a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, or a cyano group, may be a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a cyano group, may be a hydrogen atom, a methyl group, an iso-propyl group, a tert-butyl group, a diarylamine group, a phenyl group, a phenyl group having an alkyl group as a substituent, or a biphenyl group, and may be a methyl group or a tert-butyl group.

[0031] A 1 and A 2 are each independently selected from the group consisting of a chalcogen atom, NR 10 , and CR 11 R 12 wherein R 10 to R 12is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted 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.

[0032] A 1 and A 2 is preferably an oxygen atom, a sulfur atom, a selenium atom, or NR 10 from the viewpoint of durability. A 1 and A 2 is preferably an oxygen atom, a sulfur atom, a selenium atom, or CR 11 R 12 from the viewpoint of oscillator strength. A 1 and A 2 is preferably an oxygen atom or a sulfur atom from the viewpoint of ease of synthesis.

[0033] X 1 and X 2 are each independently selected from the group consisting of a chalcogen atom, NR 10 , and CR 11 R 12 R 10 to R 12 is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted 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.

[0034] X 1 and X 2 is preferably a chalcogen atom or CR 11 R 12 and is preferably an oxygen atom or a sulfur atom from the viewpoint of ease of synthesis.

[0035] In general formula (2), Z is a direct bond, a chalcogen atom, a substituted or unsubstituted methylene group, a substituted or unsubstituted silylene group, an imino group substituted with an aryl group, or a substituted or unsubstituted aryl group. Specifically, Z is a direct bond, an oxygen atom, a sulfur atom, a selenium atom, a methylene group substituted with a methyl group, a silylene group substituted with a methyl group, an imino group substituted with a phenyl group, or a phenyl group.

[0036] a to d are each an integer of 0 or more and 4 or less. However, in general formula (2), a and b are each an integer of 0 or more and 3 or less.

[0037] A plurality of Rs 1 may be the same as or different from each other. A plurality of Rs 2 may be the same as or different from each other. A plurality of Rs 3 may be the same as or different from each other. A plurality of Rs 4 may be the same as or different from each other.

[0038] However, the organic compound according to the present invention may exclude an organic compound in which A 1 , A 2 , X 1 , and X 2 are sulfur atoms. On the other hand, when the heterocyclic group, which is one of the substituents of general formula (3), has 29 or fewer carbon atoms, A 1 , A 2 , X 1 , and X 2 in general formula (3) may be sulfur atoms. Specifically, it is as follows.

[0039] The organic compound according to the present embodiment is characterized by being represented by general formulas (1) to (3).

[0040]

Chemical formula

[0041] In general formulas (1) to (3), R 1 to R 4 are each independently selected from the group consisting of a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group having 29 or fewer carbon atoms, 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. R 5 is 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 having 29 or fewer carbon atoms, 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, or a cyano group. A 1 , A 2 、 X 1 、 and X 2 are each independently selected from the group consisting of a chalcogen atom, NR 10 , and CR 11 R 12 . R 10 to R 12 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted 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. a to d are each an integer of 0 or more and 4 or less. However, in general formula (2), a and b are each an integer of 0 or more and 3 or less. A plurality of R 1 may be the same as or different from each other. A plurality of R 2 may be the same as or different from each other. A plurality of R 3 may be the same as or different from each other. A plurality of R 4They may be the same as or different from each other.

[0042] Hereinafter, the present invention will be described in detail.

[0043] Since the organic compound according to the present invention has a structure represented by general formulas (1) to (3), it exhibits a high oscillator strength.

[0044] As described in paragraph

[0262] of JP-A-2020-47930 and paragraph

[0035] of JP-A-2022-46999, it is known that a compound having a high oscillator strength tends to exhibit a high quantum yield (luminescence efficiency). Therefore, it is preferable that the oscillator strength of the organic compound shows a high value.

[0045] Table 1 shows the values of the oscillator strength of the organic compound according to the present invention and the organic compound described in Patent Document 1 which is a comparative example. The oscillator strength was calculated using Gaussian 16 (Gaussian 16, Revision C.01, M. J. Frisch, et al, Gaussian, Inc., Wallingford CT, 2019.), which is software for molecular orbital calculations manufactured by Gaussian, USA. B3LYP / 6-31G* was used as the basis function.

[0046] [Table 1]

[0047] From Table 1, Inventions A to C according to the present invention, which are organic compounds according to the present invention, showed a higher oscillator strength than Comparative Example A, which is an organic compound described in Patent Document 1. Therefore, the organic compound according to the present invention is an organic compound showing a high oscillator strength.

[0048] Hereinafter, a more preferable form of the organic compound according to the present invention will be described. The organic compound according to the present embodiment preferably has at least one of the following characteristics (A), (B), (C), and (D). (A) The organic compound exhibits a large molar extinction coefficient (B) The organic compound is represented by the general formula (1) or (3). (C) The organic compound has a bulky substituent. (D) When the organic compound has a heterocyclic group as a substituent, the number of carbon atoms in the heterocyclic group is 29 or less.

[0049] Hereinafter, these features will be described.

[0050] (A) The organic compound exhibits a large molar extinction coefficient. The organic compound according to the present invention preferably exhibits a large value of the molar extinction coefficient.

[0051] Since the oscillator strength of the organic compound is proportional to the magnitude of the molar extinction coefficient of the organic compound, an organic compound having a large molar extinction coefficient exhibits a high oscillator strength.

[0052] In addition, by using an organic compound having a high molar extinction coefficient as a light-emitting material, the energy transfer efficiency of excitons is improved, so that an improvement in the light-emitting efficiency of an organic light-emitting device using the organic compound according to the present embodiment can be expected. For the above reasons, the organic compound according to the present invention preferably exhibits a large value of the molar extinction coefficient.

[0053] The organic compound according to the present embodiment may have a molar extinction coefficient greater than 23000 L mol -1 cm -1 and preferably 30000 L mol -1 cm -1 or more, more preferably 40000 L mol -1 cm -1 or more, and particularly preferably 47000 L mol -1 cm -1 or more.

[0054] The molar extinction coefficient can be calculated from the absorption intensity at the peak top of the spectral peak on the long wavelength side of the absorption spectrum by performing visible / ultraviolet absorption measurement on a solution adjusted so that the concentration of the compound is 10 ―5 mol / L.

[0055] (B) The organic compound is represented by the general formula (1) or (3). The organic compound according to the present invention is preferably represented by the general formula (1) or (3).

[0056] Generally, by increasing the dipole moment (transition dipole moment) in the transition process in the excitation process from the singlet ground state to the lowest excited singlet state, the oscillator strength in the excitation process can be increased.

[0057] Among the organic compounds according to the present invention, in the excitation process from the singlet ground state to the lowest excited singlet state, the change in electron distribution in the long axis direction of the basic skeleton (the arrow direction of Invention A and Invention C in FIG. 8) is larger than that of the organic compound represented by the general formula (2). Therefore, it has a larger transition dipole moment. As a result, the organic compounds represented by the general formula (1) and (3) exhibit a larger oscillator strength.

[0058] For the above reasons, it is preferable that the organic compound according to the present invention is represented by the general formula (1) or (3) because it exhibits a larger oscillator strength.

[0059] (C) The organic compound has a bulky substituent. The organic compound according to the present invention preferably has a bulky substituent because its sublimability is improved. In addition, it is preferable because an improvement in solubility and a narrowing of the half-value width of the emission spectrum can also be expected.

[0060] Here, the bulky substituent is a substituent that can cover the basic skeleton. Specifically, it is a branched alkyl group, an aryl group having a substituent, a diarylamine group, an iso-propyl group, an iso-butyl group, a tert-butyl group, a ter-phenyl group, a phenyl group having a substituent at the ortho position, a trimethylphenyl group, a biphenyl group, a biphenylamino group, etc. Examples of the substituent that the phenyl group has at the ortho position include a methyl group and a phenyl group.

[0061] Among the compounds according to the present invention, R 5 preferably has a bulky substituent. By providing a bulky substituent to R 5 , intermolecular interaction can be more effectively suppressed, so intermolecular stacking can be more suppressed. Therefore, the organic compound according to the present invention preferably has a bulky substituent, and it is more preferable that R 5 has a bulky structure.

[0062] (D) When the organic compound has a heterocyclic group as a substituent, the heterocyclic group has 29 or less carbon atoms When the organic compound according to the present invention has a heterocyclic group as a substituent, it is preferable that the heterocyclic group has 29 or less carbon atoms. At this time, the organic compound according to the present embodiment is an organic compound having more excellent oscillator strength.

[0063] Table 2 shows the oscillator strengths of Invention D, which is an organic compound according to the present embodiment, and Comparative Example B, which is an organic compound described in Patent Document 2.

[0064]

Table 2

[0065] The oscillator strength of Invention D was 0.185, while the oscillator strength of Comparative Example B was 0.041. This is presumably because, as in Comparative Example B, having a heterocyclic group with 30 or more carbon atoms as a substituent makes the HOMO orbital distribution tend to be uneven on the substituent, and the direction of the transition dipole moment is deviated from the long axis direction.

[0066] Therefore, when the organic compound according to the present invention has a heterocyclic group as a substituent, it is preferable that the heterocyclic group has 29 or less carbon atoms, and more preferably 4 or more and 12 or less carbon atoms. Specifically, it is a furan skeleton, a benzofuran skeleton, a dibenzofuran skeleton, a thiophene skeleton, a benzothiophene skeleton, a dibenzothiophene skeleton, or a carbazole skeleton, and particularly preferably a carbazole skeleton.

[0067] Specific examples of the organic compound according to the present invention are shown below. However, the present invention is not limited thereto.

[0068]

Chemical formula

[0069]

Chemical formula

[0070]

Chemical formula

[0071]

Chemical formula

[0072]

Chemical formula

[0073]

Chemical formula

[0074]

Chemical formula

[0075]

Chemical formula

[0076]

Chemical formula

[0077]

Chemical formula

[0078]

Chem.

[0079]

Chem.

[0080]

Chem.

[0081]

Chem.

[0082]

Chem.

[0083]

Chem.

[0084]

Chem.

[0085]

Chem.

[0086]

Chem.

[0087]

Chem.

[0088] [Chemistry]

[0089] [Chemistry]

[0090] [Chemistry]

[0091] [Chemistry]

[0092] [Chemistry]

[0093] [Chemistry]

[0094] [Chemistry]

[0095] [Chemistry]

[0096] [Chemistry]

[0097] [Chemistry]

[0098] [Chemistry]

[0099]

Chem.

[0100]

Chem.

[0101]

Chem.

[0102]

Chem.

[0103]

Chem.

[0104]

Chem.

[0105]

Chem.

[0106]

Chem.

[0107]

Chem.

[0108]

Chem.

[0109]

Chem.

[0110]

Chem.

[0111]

Chem.

[0112]

Chem.

[0113]

Chem.

[0114]

Chem.

[0115]

Chem.

[0116]

Chem.

[0117]

Chem.

[0118]

Chem.

[0119]

Chem.

[0120]

Chem.

[0121]

Chem.

[0122]

Chem.

[0123]

Chem.

[0124]

Chem.

[0125]

Chem.

[0126]

Chem.

[0127]

Chem.

[0128]

Chem.

[0129]

Chem.

[0130]

Chem.

[0131]

Chem.

[0132]

Chem.

[0133]

Chem.

[0134]

Chem.

[0135] (2) Organic light-emitting device Next, the organic light-emitting device according to this embodiment will be described. The organic light-emitting device according to this embodiment has a first electrode and a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is an anode and the other is a cathode. In the organic light-emitting device according to this embodiment, the organic compound layer may be a single layer or a laminate composed of a plurality of layers as long as it has a light-emitting layer. The organic compound according to the present invention may be included in the organic compound layer, and is preferably included in the light-emitting layer. Here, when the organic compound layer is a laminate composed of a plurality of layers, in addition to the light-emitting layer, the organic compound layer may have a hole injection layer, a hole transport layer, an electron blocking layer, a hole-exciton blocking layer, an electron transport layer, an electron injection layer, and the like. Also, the light-emitting layer may be a single layer or a laminate composed of a plurality of layers. When the light-emitting layer is a plurality of layers, a charge generation layer may be provided between the light-emitting layers. The charge generation layer may be composed of a compound whose LUMO energy level is lower than the LUMO energy level of the hole transport layer, and the LUMO energy level of the charge generation layer may be lower than the HOMO energy level of the hole transport layer. Here, the HOMO energy level and the LUMO energy level of the organic compound layer may be the HOMO energy level and the LUMO energy level of the organic compound having the largest weight ratio in the organic compound layer.

[0136] Here, the HOMO energy level and the LUMO energy level are described as "higher" the closer they are to the vacuum level. That the LUMO energy level of the charge generation layer is lower than the HOMO energy level of the hole transport layer means that the LUMO energy level of the charge generation layer is farther from the vacuum level than the HOMO energy level of the hole transport layer.

[0137] In this specification, the HOMO energy level and the LUMO energy level can be calculated using molecular orbital calculations. The molecular orbital calculations may be performed by the density functional theory (DFT) or the like, and the functional may be B3LYP and the basis function may be 6-31G* or the like.The molecular orbital calculations can be carried out using, for example, Gaussian09 (Gaussian09, Revision C.01, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox, Gaussian, Inc., Wallingford CT, 2010.) or Gaussian 16 (Gaussian 16, Revision C.01, M. J. Frisch, et al, Gaussian, Inc., Wallingford CT, 2019.).

[0138] The HOMO energy level and LUMO energy level in this specification can be calculated using the ionization potential and the band gap. The HOMO energy level can be estimated by measuring the ionization potential. The ionization potential can be measured with a measuring device such as AC-3 after dissolving the compound to be measured in a solvent such as toluene or after forming a vapor deposition film of the compound to be measured on a substrate such as glass. The band gap can be measured by a measurement in which the compound to be measured is dissolved in a solvent such as toluene and irradiated with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum of the excitation light. Alternatively, it can be measured by depositing the compound to be measured on a substrate such as glass and irradiating the vapor deposition film with excitation light. The measurement can measure the band gap by measuring the absorption edge of the absorption spectrum absorbed by the vapor deposition film with the excitation light.

[0139] The LUMO energy level can be calculated using the values of the band gap and the ionization potential. Subtracting the value of the ionization potential from the band gap allows the LUMO energy level to be estimated.

[0140] The LUMO energy level can also be estimated from the reduction potential. For example, the one-electron reduction potential is estimated using cyclic voltammetry (CV) measurement. The CV measurement is performed, for example, in a DMF solution of 0.1 M tetrabutylammonium perchlorate, and the reference electrode is Ag / Ag + , the counter electrode is Pt, and the working electrode can be measured using glassy carbon. The LUMO energy level can be estimated by adding the difference between the reduction potential of the obtained compound and the reduction potential of ferrocene to -4.8 eV.

[0141] In an organic light-emitting device according to an embodiment of the present invention, when the organic compound according to the present invention is included in the light-emitting layer, the light-emitting layer may be a layer composed only of the organic compound according to the present invention, or may be a layer composed of the organic compound according to the present invention and other compounds. Here, when the light-emitting layer is a layer composed of the organic compound according to the present invention and other compounds, the organic compound according to the present invention may be used as a host material of the light-emitting layer, or may be used as a guest material. It may also be used as an assist material that can be included in the light-emitting layer. Here, the host material, also referred to as "host" or "first compound", is the compound having the largest mass ratio among the compounds constituting the light-emitting layer. The guest material, also referred to as "guest", "dopant material", "dopant", or "third compound", is a compound having a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer and is a compound responsible for main emission. Therefore, the guest material may sometimes be referred to as a light-emitting material. The assist material, also referred to as "assist" or "second compound", is a compound having a mass ratio smaller than that of the host material among the compounds constituting the light-emitting layer and assists the emission of the guest material. Incidentally, the assist material is also called a second host.

[0142] Here, let the lowest excited singlet energy of the host material be S1(H), the lowest excited singlet energy of the guest material be S1(D), and the lowest excited singlet energy of the assist material be S1(A). The organic compound according to the present invention may be any of the guest material, the assist material, and the host material. At this time, it is preferable that the organic light-emitting device according to the present embodiment satisfies S1(H)>S1(D) or S1(H)>S1(A)>S1(D). By satisfying the above relationship for the lowest excited singlet energy of the compounds included in the organic light-emitting device according to the present embodiment, excitons can be efficiently transferred to the guest material, resulting in an organic light-emitting device with more excellent luminous efficiency.

[0143] When the organic compound according to the present invention is used in the light-emitting layer, the concentration of the organic compound according to the present invention may be 0.01% by mass or more and 99% by mass or less with respect to the entire light-emitting layer. When the light-emitting layer is composed of the first compound and the organic compound according to the present invention, the concentration of the organic compound according to the present invention is preferably 0.01% by mass or more and 50% by mass or less, and more preferably 10% by mass or more and 50% by mass or less with respect to the entire light-emitting layer. When the light-emitting layer is composed of the first compound, the second compound, and the organic compound according to the present invention, the concentration of the organic compound according to the present invention is preferably 1% by mass or more and 50% by mass or less, and more preferably 10% by mass or more and 50% by mass or less.

[0144] The present inventors have conducted various studies and found that by using the organic compound according to the present invention in the light-emitting layer, an element that exhibits a highly efficient and high-brightness light output and has extremely high durability can be obtained. This light-emitting layer may be a single layer or a multilayer, and it is also possible to mix colors by including a light-emitting material having another emission color. The multilayer means a state in which a light-emitting layer and another light-emitting layer are laminated. In this case, the emission color of the organic light-emitting device is not limited to a single color. More specifically, it may be white or an intermediate color. In the case of white, when the light-emitting layer emits blue light, another light-emitting layer emits a color other than blue, that is, red or green. Also, the film formation method is film formation by evaporation or coating film formation.

[0145] The organic compound according to the present invention can be used as a constituent material of an organic compound layer other than the light-emitting layer constituting the organic light-emitting device according to the present embodiment. Specifically, it may be used as a constituent material for an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, and the like. In this case, the emission color of the organic light-emitting device is not limited to a single color. More specifically, it may be white light emission or an intermediate color.

[0146] (3) Other Compounds Here, in addition to the organic compound according to the present invention, conventionally known low-molecular and high-molecular hole injection compounds or hole transport compounds, host materials, light-emitting compounds, electron injection compounds or electron transport compounds, etc. can be used together as needed. Examples of these compounds are given below.

[0147] As the hole injection and transport material, a material with a high hole mobility is preferred so as to facilitate the injection of holes from the anode and transport the injected holes to the light-emitting layer. Also, in order to suppress the crystallization of organic compounds in the organic light-emitting device, a material with a high glass transition temperature is preferred. Examples of low-molecular and high-molecular materials having hole injection and transport performance include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above hole injection and transport materials are also preferably used for the electron blocking layer. Also, when the hole injection layer is formed by a coating method, a mixture of polyethylene dioxythiophene and polystyrene sulfonic acid (PEDOT:PSS), which is generally used as the hole injection material, may be used. Specific examples of the compounds used as the hole injection and transport materials are shown below, but of course, the present invention is not limited thereto.

[0148] [Chemical formula]

[0149] Among the hole injection and transport materials mentioned, HT16 to HT18 can reduce the driving voltage when used in the layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2 to HT7, HT10, HT12, and HT22 to 28 may be used in the organic compound layer adjacent to HT16. Polymer compounds such as hole-transporting polyphenylene vinylene (PPV), polyfluorene (PF), polyvinyl carbazole (PVK), and their derivatives may also be used. In addition, for example, inorganic insulating layers such as SiO2 and SiN or organosilicon polymers such as siloxane can also be used. Also, a plurality of materials may be used in one organic compound layer.

[0150] Guest materials mainly related to the light-emitting function include donor-acceptor type organic compounds, boron-containing complexes, indolocarbazole fused-ring compounds, fused-ring compounds (such as 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(phenylene vinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Also, when the light-emitting layer is fabricated by a coating method, a polymer compound mainly having light-emitting properties is used. This is because polymer compounds tend to exhibit a high glass transition temperature, so crystallization is less likely to occur compared to low-molecular-weight systems. Specific materials used include polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinyl carbazole (PVK), and their derivatives.

[0151] Specific examples of the compounds used as the light-emitting material are shown below, but of course, they are not limited to these.

[0152]

Chemical formula

[0153]

Chem.

[0154] Specific examples of the compounds used as the host material or assist material contained in the light-emitting layer are shown below, but of course, they are not limited thereto.

[0155]

Chem.

[0156] As the electron transport material, it can be arbitrarily selected from those capable of transporting the electrons injected from the cathode to the light-emitting layer, and is selected in consideration of the balance with the hole mobility of the hole transport material, etc. Examples of the material having electron transport performance include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, condensed ring compounds (for example, fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transport materials are also preferably used for the hole blocking layer.

[0157] Specific examples of the compounds used as the electron transport material are shown below, but of course, they are not limited thereto.

[0158]

Chem.

[0159] As the electron injection material, it can be arbitrarily selected from those that enable easy electron injection from the cathode, and is selected in consideration of the balance with hole injection properties and the like. Organic compounds also include n-type dopants and reducing dopants. For example, compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives can be mentioned.

[0160] Also, it can be used in combination with the above electron transport material.

[0161] In addition, the organic compound according to the present invention can also be used as an ink composition.

[0162] The ink composition according to this embodiment contains at least one compound represented by general formulas (1) to (3). By using the ink composition according to this embodiment, it becomes possible to produce a layer made of an organic compound constituting an organic light-emitting element, particularly a light-emitting layer, by a coating method, and a relatively inexpensive and large-area element can be easily produced. Examples of the solvent for dissolving the compounds represented by general formulas (1) to (3) include toluene, xylene, mesitylene, dioxane, methylnaphthalene, tetrahydrofuran, diglyme, 1,2-dichlorobenzene, 1,2-dichloropropane, and the like. These solvents can be used alone or in combination of two or more. Among these, in terms of easily obtaining a thin film having a uniform thickness, it is preferable to use a solvent having an appropriate evaporation rate, specifically, a solvent having a boiling point of about 70 to 200°C. Further, the ink composition according to this embodiment may contain other compounds as additives. Examples of the compounds as additives include the above-mentioned known light-emitting layer hosts or light-emitting assist materials, hole transport materials, light-emitting materials, electron transport materials, and the like.

[0163] The concentration of the compound represented by general formulas (1) to (3) in the ink composition according to this embodiment is preferably 0.05% by weight or more and 20% by weight or less, more preferably 0.1% by weight or more and 5% by weight or less, based on the whole composition.

[0164] The ink composition according to this embodiment can form the organic layer of the organic light-emitting device described below by forming 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, or the like.

[0165] (4) Structure of the organic light-emitting device Hereinafter, the constituent members of the organic light-emitting device of this embodiment will be described.

[0166] The organic light-emitting device 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 providing a color filter, a planarization layer may be provided between the protective layer. The planarization layer can be composed of an acrylic resin or the like. The same applies when providing a planarization layer to between the color filter and the microlens.

[0167] [Substrate] Examples of the substrate include quartz, glass, silicon wafers, resins, metals, and the like. Further, a switching element such as a transistor or wiring may be provided on the substrate, and an insulating layer may be provided thereon. As the insulating layer, any material may be used as long as a contact hole can be formed so that wiring can be formed between the insulating layer and the first electrode, and insulation from non-connected wiring can be ensured. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0168] [Electrode] A pair of electrodes can be used for the electrodes. The pair of electrodes are the first electrode and the second electrode. Specifically, 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 device emits light, the electrode with the 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.

[0169] As the constituent material of the anode, it is preferable to use a material with as large a work function as possible. For example, simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, etc., mixtures containing these, alloys combined with these, metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide, etc. can be used. Also, conductive polymers such as polyaniline, polypyrrole, polythiophene, etc. can be used.

[0170] These electrode materials may be used alone or in combination of two or more. Also, the anode may be composed of a single layer or multiple layers.

[0171] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys thereof, laminated materials, etc. can be used. The above materials can also function as a reflective film without having the role of an electrode. Also, when used as a transparent electrode, oxide transparent conductive layers such as indium tin oxide (ITO), indium zinc oxide, etc. can be used, but it is not limited to these. For the formation of the electrode, photolithography technology can be used.

[0172] As the constituent material of the cathode, those with a small work function are preferable. For example, alkali metals such as lithium, alkaline earth metals such as calcium, simple metals such as aluminum, titanium, manganese, silver, lead, chromium, or mixtures containing these can be mentioned. Alternatively, alloys combining these simple metals can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver, etc. can be used. The use of metal oxides such as indium tin oxide (ITO) is also possible. These electrode materials may be used alone or in combination of two or more. Also, the cathode may have a single-layer structure or a multi-layer structure. Among them, it is preferable to use silver, and in order to reduce the aggregation of silver, it is more preferable to use a silver alloy. As long as the aggregation of silver can be reduced, the ratio of the alloy does not matter. For example, silver: other metals may be 1:1, 3:1, etc.

[0173] 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. As a method for forming the cathode, although not particularly limited, the use of direct current and alternating current sputtering methods, etc., is more preferable because the film coverage is good and the resistance is easily reduced.

[0174] [Organic compound layer] The organic compound layer may be formed as a single layer or as a plurality of layers. When having a plurality of layers, depending on its function, it may be called a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer. The organic compound layer is mainly composed of an organic compound, but may contain inorganic atoms or inorganic compounds. For example, it may have copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be disposed between the first electrode and the second electrode, and may be arranged in contact with the first electrode and the second electrode.

[0175] The organic compound layers (such as 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 this embodiment are formed by the methods shown below.

[0176] For the organic compound layers constituting the organic light-emitting device according to this embodiment, dry processes such as vacuum evaporation method, ionization evaporation method, sputtering, and plasma can be used. Also, instead of the dry process, a wet process of dissolving in an appropriate solvent and forming a layer by a known coating method (for example, spin coating, dipping, casting method, LB method, inkjet method, etc.) can be used.

[0177] Here, by forming a layer by a vacuum evaporation method, a solution coating method, etc., crystallization and the like are less likely to occur and the stability over time is excellent. Also, when forming a film by a coating method, a film can be formed in combination with an appropriate binder resin.

[0178] Examples of the binder resin include, but are not limited to, polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, urea resin, etc.

[0179] These binder resins may be used alone as a homopolymer or copolymer, or two or more kinds may be mixed and used. Furthermore, additives such as known plasticizers, antioxidants, and ultraviolet absorbers may be used in combination as needed.

[0180] [Protective layer] A protective layer may be provided on the cathode. For example, by adhering a glass provided with a moisture absorbent on the cathode, the intrusion of water or the like into the organic compound layer can be reduced, and the occurrence of display defects can be reduced. Further, as another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the intrusion of water or the like into the organic compound layer. For example, after forming the cathode, it may be transported to another chamber without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm may be formed by CVD method, which may also serve as a protective layer. A protective layer using atomic layer deposition (ALD) method may be provided after the film formation by CVD method. The material of the film by ALD method is not limited, but it may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed by CVD method on the film formed by ALD method. The film formed by ALD method may have a smaller film thickness than the film formed by CVD method. Specifically, the film thickness of the film formed by ALD method may be 50% or less, and further 10% or less of the film thickness of the film formed by CVD method.

[0181] [Color filter] A color filter may be provided on the protective layer. For example, a color filter considering the size of the organic light-emitting element may be provided on another substrate and bonded to the substrate provided with the organic light-emitting element, or the color filter may be patterned on the above-described protective layer using photolithography technology. The color filter may be composed of a polymer.

[0182] [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. Without limiting the purpose, it may sometimes be called a material resin layer. The planarization layer may be composed of an organic compound, and may be a low molecule or a polymer, but a polymer is preferred.

[0183] The planarization layer may be provided above and below the color filter, and the constituent materials thereof may be the same or different. Specifically, examples include polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicon resin, urea resin, and the like.

[0184] [Micro lens] The organic light-emitting element according to this embodiment may have an optical member such as a micro lens on the light-emitting side. The micro lens may be made of acrylic resin, epoxy resin, or the like. The micro lens may be for the purpose of increasing the amount of light extracted from the organic light-emitting element and controlling the direction of the extracted light. The micro lens may have a hemispherical shape. When having a hemispherical shape, among the tangents in contact with the hemisphere, there is a tangent parallel to the insulating layer, and the contact point between the tangent and the hemisphere is the vertex of the micro lens. The vertex of the micro lens can be determined similarly in any cross-sectional view. That is, among the tangents in contact with the semi-circle of the micro lens in the cross-sectional view, there is a tangent parallel to the insulating layer, and the contact point between the tangent and the semi-circle is the vertex of the micro lens.

[0185] Also, the midpoint of the micro lens can be defined. In the cross-section of the micro lens, a line segment from the point where the arc shape starts to the point where another arc shape starts is imagined, and the midpoint of the line segment can be called the midpoint of the micro lens. The cross-section for discriminating the vertex and the midpoint may be a cross-section perpendicular to the insulating layer.

[0186] [Counter substrate] A counter substrate may be provided on the planarization layer. Since the counter substrate is provided at a position corresponding to the aforementioned substrate, it is called a counter substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is the first substrate, the counter substrate may be the second substrate.

[0187] [Pixel circuit] The light-emitting device may have a pixel circuit connected to a light-emitting element. The pixel circuit may be an active matrix type that independently controls the light emission of a first light-emitting element and a second light-emitting element. The active matrix type circuit may be voltage programming or current programming. The driving circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission luminance of the light-emitting element, a transistor that controls the emission timing, a capacitor that holds the gate voltage of the transistor that controls the emission luminance, and a transistor for connecting to GND without passing through the light-emitting element.

[0188] The light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of the transistors constituting the pixel circuit may be smaller than the mobility of the transistors constituting the display control circuit.

[0189] The slope of the current-voltage characteristics of the transistors constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistors constituting the display control circuit. The slope of the current-voltage characteristics can be measured by so-called Vg-Ig characteristics.

[0190] The transistors constituting the pixel circuit are transistors connected to a light-emitting element such as a first light-emitting element.

[0191] [Pixel] The organic light-emitting device has a plurality of pixels. The pixels have sub-pixels that emit different colors from each other. The sub-pixels may have, for example, emission colors of RGB respectively.

[0192] In the pixel, a region also called a pixel aperture emits light. This region is the same as the first region. The pixel aperture may be 15 μm or less and may be 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc.

[0193] The distance between the sub-pixels may be 10 μm or less, and specifically may be 8 μm, 7.4 μm, 6.4 μm.

[0194] In a plan view, the pixels can take a known arrangement form. For example, it may be a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the sub-pixels in the plan view may take any known shape. For example, it may be a quadrilateral such as a rectangle or a rhombus, a hexagon, etc. Of course, even if it is not an exact figure but has a shape close to a rectangle, it is included in the rectangle. The shape of the sub-pixels and the pixel arrangement can be used in combination.

[0195] (5) Applications of the organic light-emitting device according to the present embodiment The organic light-emitting device according to the present embodiment can be used as a component of a display device or a lighting device. In addition, there are applications such as an exposure light source of an electrophotographic image forming device, a backlight of a liquid crystal display device, and a light-emitting device having a color filter for a white light source.

[0196] 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 a display unit that displays the input image.

[0197] In addition, the display unit of an imaging device or an 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. Also, the display device may be used for the display unit of a multifunction printer.

[0198] Next, the display device according to the present embodiment will be described with reference to the drawings.

[0199] FIG. 1 is a cross-sectional schematic view showing an example of a display device having an organic light-emitting device and a transistor connected to the organic light-emitting device. The transistor is an example of an active element. The transistor may be a thin film transistor (TFT).

[0200] FIG. 1(a) shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B according to their light emission. The emission color may be distinguished by the wavelength emitted from the light-emitting layer, or the light emitted from the sub-pixels may be selectively transmitted or color-converted by a color filter or the like. Each sub-pixel has a reflective electrode 2, which is a first electrode, on an interlayer insulating layer 1, an insulating layer 3 covering the edge of the reflective electrode 2, an organic compound layer 4 covering the first electrode and the insulating layer, a transparent electrode 5, a protective layer 6, and a color filter 7.

[0201] A transistor and a capacitor element may be arranged in or under the interlayer insulating layer 1. The transistor and the first electrode may be electrically connected through a contact hole or the like (not shown).

[0202] The insulating layer 3 is also called a bank or a pixel isolation film. It covers the edge of the first electrode and is arranged surrounding the first electrode. The portion where the insulating layer is not arranged is in contact with the organic compound layer 4 and becomes a light-emitting region.

[0203] The organic compound layer 4 has a hole injection layer 41, a hole transport layer 42, a first light-emitting layer 43, a second light-emitting layer 44, and an electron transport layer 45.

[0204] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transmissive electrode.

[0205] The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is shown as a single layer, it may be a plurality of layers. Each layer may have an inorganic compound layer and an organic compound layer.

[0206] The color filter 7 is divided into 7R, 7G, and 7B according to its color. The color filter may be formed on a planarization film (not shown). Also, it may have a resin protective layer (not shown) on the color filter. Further, the color filter may be formed on the protective layer 6. Or it may be bonded after being provided on a counter substrate such as a glass substrate.

[0207] The display device 100 in Fig. 1(b) describes an organic light-emitting element 26 and a TFT 18 as an example of a transistor. A substrate 11 such as glass or silicon has an insulating layer 12 provided thereon. On the insulating layer, active elements 18 such as TFTs are arranged, and a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element are arranged. The active element 18 is also composed of a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on the active element 18. The anode 21 constituting the organic light-emitting element 26 is connected to the source electrode 17 through a contact hole 20 provided in the insulating film.

[0208] Note that the method of electrical connection between the electrodes (anode, cathode) included in the organic light-emitting element 26 and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the mode shown in Fig. 1(b). That is, it is sufficient that either one of the anode or the cathode is electrically connected to either one of the TFT source electrode or the drain electrode. TFT refers to a thin-film transistor.

[0209] In the display device 100 of Fig. 1(b), the organic compound layer is illustrated as one layer, but the organic compound layer 22 may be a plurality of layers. A first protective layer 24 and a second protective layer 25 for reducing the deterioration of the organic light-emitting element are provided on the cathode 23.

[0210] In the display device 100 of Fig. 1(b), a transistor is used as a switching element, but other switching elements may be used instead.

[0211] Also, the transistor used in the display device 100 of Fig. 1(b) is not limited to a transistor using a single-crystalline silicon wafer, and may be a thin-film transistor having an active layer on an insulating surface of a substrate. Examples of the active layer include non-single-crystalline silicon such as single-crystalline silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystalline oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Note that the thin-film transistor is also called a TFT element.

[0212] The transistor included in the display device 100 in FIG. 1(b) may be formed within a substrate such as an Si substrate. Here, forming within the substrate means fabricating the transistor by processing the substrate itself such as an Si substrate. That is, having a transistor within the substrate can also be regarded as the substrate and the transistor being integrally formed.

[0213] The organic light-emitting element according to the present embodiment has its emission luminance controlled by a TFT which is an example of a switching element, and an image can be displayed by the respective emission luminances by providing the organic light-emitting elements in a plurality of planes. 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 an Si substrate. "On the substrate" can also mean within the substrate. Whether to provide a transistor within 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 the organic light-emitting element on the Si substrate.

[0214] FIG. 2 is a schematic diagram showing an example of the display device according to the present embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The display panel 1005 may have the organic light-emitting element according to the present embodiment. The touch panel 1003 and the display panel 1005 are respectively connected to flexible printed circuits FPC 1002 and 1004. A transistor is printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, or may be provided at another position even if it is a portable device.

[0215] The display device according to the present embodiment may have a color filter having red, green, and blue. The red, green, and blue of the color filter may be arranged in a delta array.

[0216] The display device according to this embodiment may be used for the display unit of a mobile terminal. In that case, it may have both a display function and an operation function. Examples of the mobile terminal include mobile phones such as smartphones, tablets, head-mounted displays, and the like.

[0217] The display device according to this embodiment may be used for the display unit of an imaging device having an imaging element that receives light. The imaging device may have a display unit that displays information acquired by the imaging element. Further, the display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed in the viewfinder. The imaging device may be a digital camera or a digital video camera.

[0218] FIG. 3(a) is a schematic diagram showing an example of the 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 and the rear display 1102 may include the organic light-emitting element according to this embodiment. In that case, the viewfinder 1101 and the rear display 1102 may display not only the 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 moves, the possibility that the subject is shielded by an obstacle, and the like.

[0219] Since the timing suitable for imaging is a very short time, it is better to display information as soon as possible. Therefore, it is preferable to use the display device using the organic light-emitting element according to this embodiment. This is because the organic light-emitting element has a high response speed.

[0220] The imaging device 1100 may further include an optical unit (not shown). The lens(es) included in the optical unit may be single or plural, and forms an image on the imaging element housed in the housing 1104. By adjusting the relative positions of the plurality of lenses, the focus can be adjusted. This operation can also be performed automatically. The imaging device may be referred to as a photoelectric conversion device. The photoelectric conversion device may include, as imaging methods, methods such as detecting the difference from a previous image instead of sequentially imaging, and cutting out from an image that is always recorded.

[0221] FIG. 3(b) is a schematic diagram showing an example of the electronic device according to the present embodiment. The electronic device 1200 includes a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may include 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 reaction unit of a touch panel method. The operation unit may be a biometric recognition unit that recognizes a fingerprint to unlock etc. An electronic device having a communication unit can also be called a communication device. The electronic device may further have a camera function by including a lens and an imaging element. An image captured by the camera function is displayed on the display unit. Examples of the electronic device include a smartphone, a notebook personal computer, etc.

[0222] FIG. 4 is a schematic diagram showing an example of the display device according to the present embodiment. FIG. 4(a) shows a display device such as a TV monitor or a PC monitor. The display device 1300 includes a housing 1301 and a display unit 1302. An organic light-emitting element according to the present embodiment may be used for the display unit 1302.

[0223] The display device 1300 may include a housing 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form of FIG. 4(a). The lower side of the housing 1301 may also serve as the base.

[0224] Further, the housing 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0225] Figure 4(b) is a schematic diagram showing another example of the display device according to the present embodiment. The display device 1310 in Figure 4(b) is configured to be foldable and is a so-called foldable display device. The display device 1310 includes 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 the organic light-emitting elements 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 at the bending point. The first display unit 1311 and the second display unit 1312 may display different images respectively, or may display one image together with the first and second display units.

[0226] Figure 5(a) is a schematic diagram showing an example of the lighting device according to the present embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may include the organic light-emitting elements according to the present embodiment. The lighting device 1400 may include an optical film 1404 in order to improve the color rendering property of the light source. Further, the lighting device 1400 may include a light diffusing unit 1405 in order to effectively diffuse the light of the light source. By having the light diffusing unit 1405, the lighting device 1400 can deliver light over a wide range. The optical film 1404 and the light diffusing unit 1405 may be provided on the light emitting side of the lighting. A cover may be provided on the outermost part if necessary.

[0227] The lighting device is, for example, a device for lighting an interior. The lighting device may emit any color from white, day white, or other colors from blue to red. The lighting device according to the present embodiment may include a dimming circuit for dimming these. Further, the lighting device according to the present embodiment may include a power supply circuit connected to the organic light-emitting elements according to the present embodiment. The power supply circuit may be a circuit for converting an AC voltage into a DC voltage. Also, white means a color temperature of 4200K, and day white means a color temperature of 5000K. The lighting device according to the present embodiment may further include a color filter.

[0228] In addition, the lighting device according to the present embodiment may have a heat dissipation part. The heat dissipation part releases the heat inside the device to the outside of the device, and examples thereof include metals and ceramics having a high thermal conductivity.

[0229] FIG. 5(b) is a schematic diagram of an automobile which is an example of a moving body according to the present embodiment. The automobile has a tail lamp which is an example of a lighting fixture. The automobile 1500 may have a configuration in which the tail lamp 1501 lights up when a braking operation or the like is performed, and has a tail lamp 1501 and a vehicle body 1503. The vehicle body 1503 can also be referred to as an airframe. The automobile 1500 may have a window 1502 attached to the vehicle body 1503.

[0230] The tail lamp 1501 may have an organic light emitting element according to the present embodiment. The tail lamp may have a protection member for protecting the light source. The protection member has a certain degree of strength and may be made of any material as long as it is transparent, but is preferably made of polycarbonate or the like. A phthalic acid derivative, an acrylonitrile derivative, or the like may be mixed into the polycarbonate.

[0231] 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 the present embodiment. In this case, constituent materials such as electrodes of the organic light emitting element according to the present invention are made of transparent members.

[0232] The moving body according to the present embodiment includes a driving force generation part that mainly generates a driving force used for moving the moving body, and one or both of rotators mainly used for moving the moving body. The driving force generation part can be an engine, a motor, or the like. The rotator can be a tire, a wheel, a screw of a ship, a propeller of an aircraft, or the like. Specifically, it may be a bicycle, an automobile, a train, a ship, an aircraft, a drone, or the like. The moving body may have an airframe and a lighting fixture provided on the airframe. The lighting fixture may emit light in order to be known of the position of the airframe.

[0233] Referring to FIG. 6, an application example of the display device according to each of the above embodiments will be described. The display device can be applied to a system that can be worn as a wearable device such as, for example, smart glasses, a head-mounted display, or smart contact lenses. The display device that can be used in a wearable device may include an imaging device capable of photoelectrically converting visible light and a display device capable of emitting visible light.

[0234] FIG. 6 is a schematic diagram showing an example of glasses (smart glasses) according to the present embodiment. Glasses 1600 (smart glasses) will be described with reference to FIG. 6(a). Glasses 1600 have a display unit on the back surface side of lens 1601. The display unit may include an organic light-emitting element according to the present invention. Further, an imaging device 1602 such as a CMOS sensor or a SPAD may be provided on the front surface side of lens 1601.

[0235] Glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the imaging device 1602 and the display unit. Further, the control device 1603 controls the operations of the imaging device 1602 and the display unit. An optical system for condensing the light of the imaging device 1602 and the display unit is formed in lens 1601.

[0236] Using FIG. 6(b), glasses 1610 (smart glasses) will be described. The glasses 1610 have a control device 1612, and a display device having an organic light-emitting element according to the present invention is provided in the control device 1612. The control device 1612 may further have an imaging device corresponding to the imaging device 1602. An optical system for projecting light emitted from the control device 1612 is formed in the lens 1611, and an image is projected onto the lens 1611. The control device 1612 functions as a power supply for supplying power to the imaging device and the display device, and controls the operations of the imaging device and the display device. The control device may have a line-of-sight detection unit that detects the wearer's line of sight. Detection of the line of sight may use infrared rays. The infrared light-emitting unit emits infrared rays toward the eyes of the user who is gazing at the display image. Among the emitted infrared light, an imaging image of the eyes is obtained by an imaging unit having a light-receiving element detecting the reflected light from the eyes. By having a reducing means for reducing the light from the infrared light-emitting unit to the display unit in a plan view, a decrease in image quality is reduced.

[0237] From the imaging image of the eyes obtained by imaging infrared light, the control device 1612 detects the user's line of sight with respect to the display image. Any known method can be applied to the line-of-sight detection using the imaging image of the eyes. As an example, a line-of-sight detection method based on the Purkinje image by reflection of the irradiation light on the cornea can be used.

[0238] More specifically, a line-of-sight detection process based on the pupil corneal reflex method is performed. Using the pupil corneal reflex method, a line-of-sight vector representing the orientation (rotation angle) of the eyes is produced based on the image of the pupil and the Purkinje image included in the imaging image of the eyes, whereby the user's line of sight is detected.

[0239] The display device according to the present embodiment has an imaging device having a light-receiving element, and may control the display image of the display device based on the user's line-of-sight information from the imaging device.

[0240] Specifically, the display device determines, based on the line-of-sight information, a first field of view area that the user gazes at and a second field of view area outside the first field of view area. The first field of view area and the second field of view area may be determined by the control device of the display device, or the display device may receive those determined by an external control device. In the display area of the display device, the display resolution of the first field of view area may be controlled to be higher than that of the second field of view area. That is, the resolution of the second field of view area may be made lower than that of the first field of view area.

[0241] Also, the display area has a first field of view area and a second field of view area different from the first field of view area, and based on the line-of-sight information, an area with a higher priority is determined from the first field of view area and the second field of view area. The first field of view area and the second field of view area may be determined by the control device of the display device, or the display device may receive those determined by an external control device. The resolution of the area with a higher priority may be controlled to be higher than that of the area other than the area with a higher priority. That is, the resolution of the area with a relatively lower priority may be made lower.

[0242] Note that AI may be used to determine the first field of view area or the field of view area with a higher priority. AI may be a model configured to estimate the angle of the line of sight and the distance to the target at the tip of the line of sight from the eye image, using the eye image and the direction in which the eye in the image is actually looking as teacher data. AI may be possessed by the display device, the imaging device, or an external device. When the external device has AI, it can be preferably applied to smart glasses that further have an imaging device for imaging the outside. The smart glasses can display the imaged external information in real time.

[0243] FIG. 7(a) is a schematic diagram showing an example of an image forming apparatus according to the present embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus, and includes a photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transferrer 32, a conveyance 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 photoreceptor 27. This exposure light source 28 may have an organic light emitting element according to the present embodiment. The developing unit 31 has toner or the like. The charging unit 30 charges the photoreceptor 27. The transferrer 32 transfers the developed image to a storage medium 34. The conveyance roller 33 conveys 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.

[0244] FIGS. 7(b) and 7(c) are diagrams showing the exposure light source 28, and are schematic diagrams showing a state in which a plurality of light emitting portions 36 are arranged on a long substrate. Arrow 37 represents the column direction in which the organic light emitting elements are arranged. This column direction is the same as the direction of the axis around which the photoreceptor 27 rotates. This direction can also be called the major axis direction of the photoreceptor 27. FIG. 7(b) shows a form in which the light emitting portions 36 are arranged along the major axis direction of the photoreceptor 27. FIG. 7(c) shows a form different from that of FIG. 7(b), and is a form in which the light emitting portions 36 are alternately arranged in the column direction in each of the first column and the second column. The first column and the second column are arranged at different positions in the row direction. In the first column, a plurality of light emitting portions 36 are arranged at intervals. The second column has light emitting portions 36 at positions corresponding to the intervals between the light emitting portions 36 in the first column. That is, also in the row direction, a plurality of light emitting portions 36 are arranged at intervals. The arrangement in FIG. 7(c) can also be described as, for example, a state of being arranged in a grid pattern, a state of being arranged in a staggered grid, or a checkerboard pattern.

[0245] As described above, by using the apparatus using the organic light emitting element according to the present embodiment, it is possible to obtain a good image quality and a stable display even for a long-time display.

Example

[0246] Hereinafter, the present invention will be described by way of examples. However, the present invention is not limited to these.

[0247] [Example 1 (Synthesis of Compound)] (1) Synthesis of Exemplary Compound 1 Exemplary Compound 1 was synthesized according to the following procedure.

[0248] (1-1) Synthesis of Intermediate 1

[0249] [Chemical Formula]

[0250] Under a nitrogen atmosphere, 5-bromo-1,3-dimethoxy-2-methylbenzene (1.99 g), bis(4tert-butylphenyl)amine (3.60 g), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 93 mg), tri-tert-butylphosphonium tetrafluoroborate (90 mg), potassium tert-butoxide (2.82 g), and toluene (60 mL) were placed in a 100 mL eggplant flask and stirred at 120 °C for 11 hours. After returning to room temperature, ethyl acetate and distilled water were poured into the reaction solution. After extraction with ethyl acetate, it was dried over magnesium sulfate, and the filtrate was recovered by filtration. After concentrating the filtrate to dryness, it was separated by column chromatography (SiO2, ethyl acetate / heptane = 1 / 50) to obtain a white powder (2.61 g).

[0251] (1-2) Synthesis of Intermediate 2

[0252] [Chemical Formula]

[0253] Under a nitrogen atmosphere, intermediate 1 (2.48 g) and dichloromethane were placed in a 100 mL eggplant flask and cooled in an ice bath. A dichloromethane solution of boron tribromide (1 mol / L, 25 mL) was added dropwise thereto, and the mixture was stirred at room temperature for 2 hours. The reaction solution was added dropwise to an ice bath and extracted with ethyl acetate. After the extract was concentrated to dryness, it was separated by column chromatography (SiO2, ethyl acetate / heptane = 1 / 7) to obtain a white powder (1.91 g).

[0254] (1-3) Synthesis of intermediate 3

[0255]

Chemical formula

[0256] Under a nitrogen atmosphere, intermediate 2 (1.00 g), 3-Bromobenzothiophene sulfoxide (1.40 g), potassium carbonate (1.70 g), and dimethylformamide (40 mL) were placed in a 100 mL eggplant flask and stirred at 70 °C for 11 hours. After returning to room temperature, the reaction solution was filtered, and the filtrate was concentrated to dryness and then separated by column chromatography (SiO2, ethyl acetate / heptane = 1 / 1) to obtain a white powder (0.82 g).

[0257] (1-4) Synthesis of intermediate 4

[0258]

Chemical formula

[0259] Under a nitrogen atmosphere, intermediate 3 (795 mg) and toluene (20 mL) were placed in an eggplant flask and cooled in an ice bath. A solution of diisobutylaluminum hydride in hexane (1.0 mol / L, 7.5 mL) was added dropwise thereto, and the mixture was stirred at 65 °C for 2 hours. After returning to room temperature, it was neutralized with sodium hydroxide and extracted with dichloromethane. The extract was washed with distilled water and dried over anhydrous magnesium sulfate. After filtration, it was concentrated and added dropwise to methanol to obtain a white powder (680 mg).

[0260] (1 - 5) Synthesis of Exemplary Compound 1

[0261] [Chemical Structure Diagram]

[0262] Under a nitrogen atmosphere, intermediate 4 (202 mg), boron triiodide (496 mg), and ortho - dichlorobenzene (10 mL) were placed in a eggplant - shaped flask and stirred at 70 °C for 11 hours. After returning to room temperature, N,N - diisopropylethylamine (2 mL) was added and stirred, and then it was dropped into 20 mL of acetonitrile. The precipitate was collected by filtration, and the obtained crude product was separated by column chromatography (SiO2, hexane / dichloromethane = 20 / 1) to obtain a yellow solid. The obtained yellow solid was purified by sublimation (280 °C, 5.0×10 -1 Pa) to obtain a yellow powder (50 mg). The 1 results of 1H NMR measurement of the obtained yellow powder are shown below. 1 1H NMR (500 MHz, CD2Cl2): δ 8.60 (d, J = 2.5 Hz, 2H), 8.32 (q, J = 3.1 Hz, 2H), 8.22 (d, J = 8.9 Hz, 2H), 8.00 (q, J = 3.0 Hz, 2H), 7.67 (dd, J = 6.4, 2.5 Hz, 2H), 7.54 (q, J = 3.1 Hz, 4H), 2.93 (s, 3H), 1.54 (s, 18H).

[0263] [Example 2 (Measurement of Molar Absorption Coefficient)] A 10 -5 mol / L toluene solution of exemplary compound 1 was prepared and visible - ultraviolet absorption measurement was carried out. The prepared toluene solution was filled into a standard quartz cell (10 mm square) and measured using a UV - 3600 manufactured by Shimadzu Corporation. The results are shown in Table 2. The absorption wavelength was the wavelength at the peak top of the spectral peak on the long - wavelength side of the observed absorption spectrum, and the molar absorption coefficient was calculated from the absorption intensity at that time.

[0264] [Table 3]

[0265] From Table 3, Exemplary Compound 1, which is an organic compound according to the present invention, showed a high molar extinction coefficient. As described above, since the oscillator strength of an organic compound is proportional to the magnitude of the molar extinction coefficient of the organic compound, the organic compounds according to the present invention are organic compounds with a high oscillator strength.

[0266] From the above, the organic compounds according to the present invention are organic compounds with a high oscillator strength. Further, the organic compounds according to one embodiment of the present invention have a molar extinction coefficient of 23000 L mol -1 ·cm -1 or greater. Therefore, an organic light-emitting device using the organic compounds according to the present invention can be expected to have excellent luminous efficiency.

[0267] Further, the present invention can also adopt the following configuration.

[0268] (Configuration 1) An organic compound characterized by being represented by General Formulas (1) to (3).

[0269]

Chemical Formula

[0270] In General Formulas (1) to (3), R 1 to R 4 are each independently selected from the group consisting of 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. R 5is a hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, or cyano group. A 1 , A 2 、 X 1 、 and X 2 are each independently selected from the group consisting of a chalcogen atom, NR 10 , and CR 11 R 12 . R 10 to R 12 are each independently selected from the group consisting of a hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, and cyano group. Z is a direct bond, a chalcogen atom, a substituted or unsubstituted methylene group, a substituted or unsubstituted silylene group, an imino group substituted with an aryl group, or a substituted or unsubstituted aryl group. a to d are each an integer of 0 or more and 4 or less. However, in General Formula (2), a and b are each an integer of 0 or more and 3 or less. A plurality of R 1 may be the same as or different from each other. A plurality of R 2 may be the same as or different from each other. A plurality of R 3 may be the same as or different from each other. A plurality of R 4 may be the same as or different from each other. However, in General Formula (3), A 1 , A 2 , X 1 , and X 2 exclude organic compounds in which they are sulfur atoms.

[0271] (Constitution 2) The organic compound according to Configuration 1, wherein the organic compound is represented by General Formula (1) or (3).

[0272] (Configuration 3) The organic compound according to Configuration 1 or 2, wherein the organic compound is represented by General Formula (1).

[0273] (Configuration 4) In General Formulas (1) to (3), X 1 and X 2 are each an oxygen atom or a sulfur atom, respectively. The organic compound according to any one of Configurations 1 to 3.

[0274] (Configuration 5) In General Formulas (1) to (3), A 1 and A 2 are each independently selected from an oxygen atom, a sulfur atom, and CR 11 R 12 respectively. The organic compound according to any one of Configurations 1 to 4.

[0275] (Configuration 6) In General Formulas (1) to (3), A 1 and A 2 are each an oxygen atom or a sulfur atom, respectively. The organic compound according to any one of Configurations 1 to 5.

[0276] (Configuration 7) In General Formula (1) or (3), X 1 and X 2 are oxygen atoms, and A 1 and A 2 are sulfur atoms, respectively. The organic compound according to any one of Configurations 1 to 6.

[0277] (Configuration 8) In General Formulas (1) to (3), R 1 to R 4is independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, an amino group having an aryl group having 6 to 12 carbon atoms, and a cyano group, R 5 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, an amino group having an aryl group having 6 to 12 carbon atoms, or a cyano group, and is the organic compound according to any one of Constitutions 1 to 7.

[0278] (Constitution 9) In General Formulas (1) to (3), R 1 to R 4 is independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, and a cyano group, and R 5 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, or a cyano group, and is the organic compound according to any one of Constitutions 1 to 8.

[0279] (Constitution 10) The molar extinction coefficient of the organic compound is 47000 L mol -1 cm -1 or more, and is the organic compound according to any one of Constitutions 1 to 9.

[0280] (Constitution 11) A first electrode and a second electrode, In an organic light-emitting device having an organic compound layer disposed between the first electrode and the second electrode, The organic compound layer has the organic compound according to any one of Constitutions 1 to 10, and is an organic light-emitting device.

[0281] (Constitution 12) The organic compound has a light-emitting layer, The organic light-emitting device according to Configuration 11, wherein the light-emitting layer contains the organic compound.

[0282] (Configuration 13) The light-emitting layer further contains a first compound, and the lowest excited singlet energy of the first compound is higher than that of the organic compound. The organic light-emitting device according to Configuration 12.

[0283] (Configuration 14) The light-emitting layer further contains a second compound, and the lowest excited singlet energy of the second compound is higher than that of the organic compound and lower than that of the first compound. The organic light-emitting device according to Configuration 13.

[0284] (Configuration 15) A display device having a plurality of pixels, wherein at least one of the plurality of pixels includes the organic light-emitting device according to any one of Configurations 11 to 14 and a transistor connected to the organic light-emitting device.

[0285] (Configuration 16) An optoelectronic conversion device having an image sensor that receives light and a display unit that displays an image captured by the image sensor, wherein the display unit includes the organic light-emitting device according to any one of Configurations 11 to 14.

[0286] (Configuration 17) An image display device having a display unit that includes the organic light-emitting device according to any one of Configurations 11 to 14 and a housing in which the display unit is provided.

[0287] (Configuration 18) An electronic device having a display unit that includes the organic light-emitting device according to any one of Configurations 11 to 14, a housing in which the display unit is provided, and a communication unit provided in the housing for communicating with the outside.

[0288] (Configuration 19) A wearable device, comprising: a display unit having an organic light-emitting element according to any one of Configurations 11 to 14; an optical system that condenses the light of the display unit; and a control device that controls the display of the display unit.

[0289] (Configuration 20) An illumination device, comprising: a light source having an organic light-emitting element according to any one of Configurations 11 to 14; and a housing in which the light source is provided.

[0290] (Configuration 21) A moving body, comprising: a lighting fixture having an organic light-emitting element according to any one of Configurations 11 to 14; and a body in which the lighting fixture is provided.

[0291] (Configuration 22) An image forming apparatus, comprising: a photoreceptor; and an exposure light source that exposes the photoreceptor, wherein the exposure light source has an organic light-emitting element according to any one of Configurations 11 to 14.

[0292] (Configuration 23) An ink composition, comprising an organic compound according to any one of Configurations 1 to 10.

Explanation of Reference Numerals

[0293] 1 Interlayer insulation layer 2 Reflective electrode 3 Insulation layer 4 Organic compound layer 5 Transparent electrode 6 Protective layer 7 Color filter 10 Sub-pixel 11 Substrate 12 Insulation layer 13 Gate electrode 14 Gate insulation film 15 Semiconductor layer 16 Drain electrode 17 Source electrode 18 Thin film transistor 19 Insulation film 20 Contact hole 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting element 27 Photoconductor 28 Exposure light source 29 Light 30 Charging unit 31 Developing unit 32 Transfer unit 33 Conveying unit 34 Recording medium 35 Fixing unit 36 Light-emitting unit 37 First direction parallel to the major axis of the photoconductor 40 Image forming apparatus 100 Display device 1000 Display device 1001 Upper cover 1002 Flexible printed circuit 1003 Touch panel 1004 Flexible printed circuit 1005 Display panel 1006 Frame 1007 Circuit board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation unit 1104 Housing 1200 Electronic device 1201 Display unit 1202 Operation unit 1203 Housing 1300 Display device 1301 Frame 1302 Display unit 1303 Base 1310 Display device 1311 First display unit 1312 Second display unit 1313 Housing 1314 Bending point 1400 Lighting device 1401 Housing 1402 Light source 1403 Circuit board 1404 Optical film 1405 Light diffusing part 1500 Automobile 1501 Tail lamp 1502 Window 1503 Vehicle body 1600 Smart glasses 1601 Lens 1602 Imaging device 1603 Control device 1610 Smart glasses 1611 Lens 1612 Control device

Claims

1. An organic compound characterized by being represented by general formula (1) to (3). 【Chemical 1】 In the general formulas (1) to (3), R １ ~R ４ are each independently selected from the group consisting of 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. ５ is 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, or a cyano group. １ , A ２ 、 X １ 、 and X ２ is a chalcogen atom, NR １０ , and C.R. １１ R １２ R is independently selected from the group consisting of １０ ~R １２ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted 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. Z is a direct bond, a chalcogen atom, a substituted or unsubstituted methylene group, a substituted or unsubstituted silylene group, an imino group substituted with an aryl group, or a substituted or unsubstituted aryl group. a to d are each an integer of 0 to 4. However, in general formula (2), a and b are each an integer of 0 to 3. A plurality of R １ may be the same or different. ２ may be the same or different. ３ The Rs may be the same as or different from each other. A plurality of Rs ４ may be the same as or different from each other. However, in general formula (3), A １ , A ２ , X １ , and X ２ exclude organic compounds in which they are sulfur atoms.

2. The organic compound according to claim 1, wherein the organic compound is represented by general formula (1) or (3).

3. The organic compound according to claim 1, wherein the organic compound is represented by general formula (1).

4. In general formulas (1) to (3), X １ and X ２ are each an oxygen atom or a sulfur atom, respectively, and the organic compound according to claim 1, characterized in that.

5. In general formulas (1) to (3), A １ and A ２ are each independently selected from an oxygen atom, a sulfur atom, and NR １０ The organic compound according to claim 1, characterized in that

6. In general formulas (1) to (3), A １ and A ２ are each an oxygen atom or a sulfur atom, respectively. The organic compound according to claim 1, characterized in that

7. In the general formula (1) or (3), X １ and X ２ are oxygen atoms, and A １ and A ２ are sulfur atoms, and the organic compound according to claim 1, characterized in that.

8. In general formulas (1) to (3), R １ to R ４ is each independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, an amino group having an aryl group having 6 to 12 carbon atoms, and a cyano group, and R ５ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, an amino group having an aryl group having 6 to 12 carbon atoms, or a cyano group, The organic compound according to claim 1, characterized in that.

9. In general formulas (1) to (3), R １ to R ４ is each independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, and a cyano group, and R ５ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, or a cyano group, The organic compound according to claim 1, characterized in that.

10. A first electrode and a second electrode, In an organic light-emitting device having an organic compound layer disposed between the first electrode and the second electrode, The organic light-emitting device, wherein the organic compound layer contains the organic compound according to claim 1.

11. The organic compound has a light-emitting layer, The organic light-emitting device according to claim 10, wherein the light-emitting layer contains the organic compound.

12. The light-emitting layer further contains a first compound, The organic light-emitting device according to claim 11, wherein the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the organic compound.

13. The light-emitting layer further contains a second compound, The organic light-emitting device according to claim 12, wherein the lowest excited singlet energy of the second compound is higher than the lowest excited singlet energy of the organic compound and lower than the lowest excited singlet energy of the first compound.

14. A display device having a plurality of pixels, wherein at least one of the plurality of pixels has the organic light-emitting device according to any one of claims 10 to 13 and a transistor connected to the organic light-emitting device.

15. An imaging device that receives light, and a display unit that displays an image captured by the imaging device, The photoelectric conversion device, wherein the display unit has the organic light-emitting device according to any one of claims 10 to 13.

16. An image display device having a display unit having the organic light-emitting device according to any one of claims 10 to 13 and a housing provided with the display unit.

17. An electronic device having a display unit having the organic light-emitting device according to any one of claims 10 to 13, a housing provided with the display unit, and a communication unit provided in the housing for communicating with the outside.

18. A wearable device, comprising: a display unit having the organic light-emitting element according to any one of claims 10 to 13; an optical system that condenses light from the display unit; and a control device that controls the display of the display unit.

19. An illumination device, comprising: a light source having the organic light-emitting element according to any one of claims 10 to 13; and a housing provided with the light source.

20. A moving body, comprising: a lighting fixture having the organic light-emitting element according to any one of claims 10 to 13; and a body provided with the lighting fixture.

Images