JP2020033329A - Organic compound, organic light emitting element, display device, imaging device, electronic apparatus, illumination device and mobile body - Google Patents

Abstract

To provide an organic compound that allows red emission with high color purity in a long wavelength region by a basic skeleton itself.SOLUTION: The present invention provides an organic compound illustrated by general formula [1]. In general formula [1], Rto Rare independently selected from a hydrogen atom, a halogen atom or a substituent. At least two of Rto Rbind to each other to form a ring structure. Of Rto R, one not forming the ring structure is selected from a hydrogen atom or the substituent.SELECTED DRAWING: Figure 1

Description

  The present invention relates to an organic compound and an organic compound having the same, an organic light-emitting element, a display device, an imaging device, an electronic device, a lighting device, and a moving object.

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

  Recent advances in organic light-emitting devices have been remarkable, and include low drive voltage, various emission wavelengths, high-speed response, and the ability to make light-emitting devices thinner and lighter.

  By the way, compounds having excellent light-emitting properties have been actively created to date. Patent Literature 1 describes a compound 1-A represented by the following structural formula as a compound having excellent light-emitting characteristics, and Patent Literature 2 describes the following compound 1-B.

  This compound 1-A emits yellow light as described later when examined by the present inventors. The compound 1-B emits red light as described later when examined by the present inventors, but has a slightly shorter wavelength.

JP 2009-302470 A JP 2013-139426 A

  As described above, the basic skeleton of the compounds described in Patent Documents 1 and 2 does not have emission characteristics in a long-wavelength region, and thus an organic light-emitting device using the same has a narrow color reproduction range. Specifically, it may be difficult to reproduce the red chromaticity coordinates (0.640, 0.330) in the sRGB color reproduction range.

  The present invention has been made in order to solve the above-mentioned problems, and an object of the present invention is to provide an organic compound in which emission of a basic skeleton is red with a longer wavelength.

  The organic compound of the present invention is represented by the following general formula [1].

In the formula [1], R _{1 to} R ₂₂ are each independently selected from a hydrogen atom or a substituent. The substituent includes a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, substituted or unsubstituted heterocyclic group. It is any of a substituted aryloxy group, silyl group and cyano group.

At least two of R _{12 to} R ₁₄ are bonded to each other to form a ring structure. Among R _{12 to} R ₁₄ , those that do not form the ring structure are selected from a hydrogen atom and the substituents.

  According to the present invention, it is possible to provide an organic compound capable of emitting red light with high color purity in a long wavelength region by the basic skeleton itself.

FIG. 2 is a schematic cross-sectional view illustrating an example of a display device including the organic light emitting device according to the embodiment and a transistor electrically connected to the organic light emitting device. FIG. 1 is a schematic diagram illustrating an example of a display device according to an embodiment. FIG. 1A is a schematic diagram illustrating an example of an imaging device according to an embodiment. FIG. 2B is a schematic diagram illustrating an example of the mobile device according to the embodiment. FIG. 1A is a schematic diagram illustrating an example of a display device according to an embodiment. (B) It is a schematic diagram showing an example of a bendable display device. (A) It is a schematic diagram which shows an example of the illumination device which concerns on this embodiment. (B) It is a schematic diagram which shows the motor vehicle which is an example of the moving body which concerns on this embodiment.

  The organic compound according to the present embodiment will be described. The novel organic compound according to the present embodiment is an organic compound represented by the following general formula [1]. In this specification, for example, the basic skeleton refers to a structure of an organic compound in which all of the positions that may be hydrogen atoms in the structure represented by the formula [1] are hydrogen atoms.

In this embodiment, in the formula [1], R _{1 to} R ₂₂ are each independently selected from a hydrogen atom, a halogen atom and a substituent. The substituent includes a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, substituted or unsubstituted heterocyclic group. It is any of a substituted aryloxy group, silyl group and cyano group.

At least two of R _{12 to} R ₁₄ are bonded to each other to form a ring structure. Among R _{12 to} R ₁₄ , those that do not form the ring structure are selected from a hydrogen atom and the substituents.

  The ring structure formed is particularly preferably an aromatic ring.

More specifically, any of the following ring structures is preferable. A ring structure formed by R ₁₂ and R ₁₃ bonded together, a ring structure formed by R ₁₃ and R ₁₄ bonded together, or a ring structure formed by R ₁₂ and R ₁₃ and R ₁₄ bonded together; Preferably, the ring structure is formed.

  Examples of the halogen atom according to this embodiment include fluorine, chlorine, bromine, iodine, and the like, but are not limited thereto. Particularly, it is preferably a fluorine atom.

  The alkyl group according to the present embodiment may be an alkyl group having 1 to 10 carbon atoms. More specifically, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, octyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group And the like, but are not limited thereto.

  The alkoxy group according to this embodiment may be an alkoxy group having 1 to 10 carbon atoms. Further, it may be an alkoxy group having 1 to 6 carbon atoms. More specifically, examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a benzyloxy group, and the like.

  The amino group according to the present embodiment may be an amino group having an alkyl group, an aryl group, or an aralkyl group as a substituent. More specifically, N-methylamino group, N-ethylamino group, N, N-dimethylamino group, N, N-diethylamino group, N-methyl-N-ethylamino group, N-benzylamino group, -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-dianisolylamino 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 and the like. But it is not limited thereto. Further, it may be an amino group having no substituent.

  The aryl group according to the present embodiment may be an aryl group having 6 to 18 carbon atoms. More specifically, examples include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, and triphenylenyl groups.

  The heterocyclic group according to this embodiment may be a heterocyclic group having 3 to 15 carbon atoms. The hetero atom of the heterocyclic group may be a nitrogen atom, an oxygen atom, or a sulfur atom. More specifically, examples include, but are not limited to, a pyridyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, a phenanthrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group. Not something.

  Examples of the aryloxy group according to the present embodiment include a phenoxy group and a thienyloxy group, but are not limited thereto.

  Examples of the silyl group according to the embodiment include a trimethylsilyl group and a triphenylsilyl group, but are not limited thereto.

  The above-mentioned alkyl group, alkoxy group, amino group, aryl group, heterocyclic group, and a substituent which the aryloxy group may further have include an alkyl group, an alkoxy group, an aryl group, an aralkyl group, an aryloxy group, and a heterocyclic group. , A substituted amino group or a halogen atom. Specific examples are as described above. Among them, an alkyl group, an aryl group, and a halogen atom may be used. When it is a halogen atom, it is preferably a fluorine atom.

In this embodiment, when R _{1 to} R ₂₂ in the general formula [1] are a substituent, it is preferable that the substituent is a substituted or unsubstituted aryl group.

In the general formula [1], the ring structure formed by R _{12 to} R ₁₄ is preferably an aromatic ring, and more preferably a benzene ring or a 5-membered ring. The benzene ring or the 5-membered ring may be plural. When a plurality of benzene rings or five-membered rings are formed, the formed ring structure may be a naphthalene ring or an indene ring. These rings are formed as fused to the basic skeleton.

In the general formula [1], at least one of a set of R ₉ and R _{18 and} a set of R ₁₀ and R ₁₇ is preferably an aryl group.

  The organic compound represented by the general formula [1] according to the present embodiment may be specifically an organic compound represented by the following general formula [2] or general formula [3].

In the formula [2], R _{1 to} R ₂₄ represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group And independently selected from a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a silyl group and a cyano group.

In the formula [3], R _{1 to} R ₂₄ represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group And independently selected from a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a silyl group and a cyano group.

  Specific examples of the substituent in the general formulas [2] and [3] are the same as the specific examples of the substituent in the formula [1].

In the general formulas [2] and [3], it is preferable that at least one of the pair of R ₉ and R ₂₀ or the pair of R ₁₀ and R ₁₉ is an aryl group.

  Next, a synthesis method of an example of the organic compound according to the present embodiment will be described. The organic compound represented by the general formula [2] is synthesized, for example, according to the following reaction scheme.

  On the other hand, the organic compound represented by the general formula [3] is synthesized, for example, according to the following reaction scheme.

As shown in the above synthesis scheme, the organic compound according to the present embodiment is synthesized using the compounds shown in the following (a) to (d) as raw materials.
(A) Acenaphthenequinone derivative (D1)
(B) Dibenzyl ketone derivative (D2)
(C) Fluoranthene derivative (D3)
(D) pyrene derivative or fluoranthene derivative (D4)

  Further, by changing the pyrene moiety and the fluoranthene moiety in the compound of D4 to phenanthrene, other organic compounds, specifically, exemplified compounds of Group E can be obtained.

Here, by appropriately introducing a substituent into the compounds shown in the above (a) to (d), any _one of R _{1 to} R _{24 in} the general formulas [1] to [3] is substituted with a predetermined substituent from a hydrogen atom. Group.

Next, since the organic compound according to the present embodiment has the following characteristics, it becomes a stable compound exhibiting red emission with high color purity, and further, by using this organic compound, the luminous efficiency is high and the device durability is high. An excellent organic light emitting device can be provided.
(1) It is a red region where the emission wavelength of the basic skeleton itself is deep (2) The oxidation potential is low and the chemical stability of the compound itself is high (3) The crystallinity is low due to the asymmetric structure

Here, the basic skeleton refers to a structure in which R _{1 to} R ₂₄ are all hydrogen atoms in the general formula [2] or [3]. The basic skeleton of the organic compound represented by the general formula [1] is an unsubstituted structure in which R _{12 to} R ₁₄ form a ring structure, in which all the substituents are hydrogen atoms.

  Hereinafter, these features will be described.

(1) The emission wavelength of the basic skeleton itself is in a deep red region The present inventors paid attention to the basic skeleton itself in creating the organic compound represented by the formula [1]. Specifically, an attempt was made to provide one in which the emission wavelength of a molecule having only the basic skeleton falls within a desired wavelength region.

  In the present embodiment, the desired wavelength region is a red region, and specifically, the maximum emission wavelength is in a band of 590 nm to 620 nm in a dilute solution.

  The emission wavelength region of the organic compound according to the present embodiment will be described while comparing a comparative compound having a structure similar to the organic compound according to the present embodiment. The exemplary compounds A1, C2, and D1 according to the present embodiment are compared with the comparative compound 1 and the comparative compound 2. The comparative compound 1 is a compound having the same basic skeleton as the compound 1-A described in Patent Document 1, and the comparative compound 2 is a compound described in Patent Document 2.

  As shown in Table 1, the emission wavelength of each organic compound was compared. The emission wavelength was measured by photoluminescence measurement of a diluted chloroform solution at an excitation wavelength of 350 nm at room temperature using Hitachi F-4500.

  From Table 1, the emission color of Comparative Compound 1 is yellow and not red. The emission color of Comparative Compound 2 is red, but not within the desired band. On the other hand, since the exemplified compounds A1, C2, and E1 have a maximum emission wavelength in a desired band, they exhibit a light emission color suitable for a display standard of red. Although E1 has a slightly shorter peak wavelength, the chromaticity indicates an emission color suitable for red of the display. Therefore, the basic skeleton of the organic compound according to this embodiment can emit deep red light. The red chromaticity coordinates will be described in detail in Examples.

(2) Low oxidation potential and high chemical stability of the compound itself When creating a material having a desired emission wavelength region, attention was paid to the HOMO energy of molecules. A long emission wavelength region means that the band gap is narrow. Therefore, it is necessary to increase the HOMO energy and to lower the LUMO energy. Here, high HOMO energy means close to the vacuum level, and low HOMO energy means far from the vacuum level. The HOMO energy is the energy of the highest occupied molecular orbital, and the LUMO energy is the energy of the lowest unoccupied molecular orbital. An organic compound having a low HOMO energy is an organic compound having a low oxidation potential.

  For example, as in Comparative Compound 3 shown in Table 2 below, a compound in which diphenylamine is bonded to a basic skeleton (benzoindenoperylene skeleton) having a condensed ring structure has an emission wavelength region of a long wavelength region (a maximum emission wavelength of 599 nm). To have. However, this organic compound is unstable to oxidation due to high HOMO energy.

  On the other hand, the organic compound according to the present embodiment is designed to have a low HOMO and LUMO energy level, and is stable against oxidation. Specifically, molecular design was performed to increase the conjugation length so that three or four electron-withdrawing 5-membered rings were present in the basic skeleton. Therefore, the HOMO and LUMO energy levels are low, that is, the oxidation potential of the organic compound is low. Therefore, the organic compound according to the present embodiment is stable against oxidation.

Here, the oxidation-reduction potentials of Exemplified Compound A2, Exemplified Compound C2, and Comparative Compound 3 were compared by CV (cyclic voltammetry) measurement. Table 2 shows the results. The CV measurement was performed under the following conditions.
Solution: DMF solution of 0.1 M tetrabutylammonium perchlorate (reduction potential measurement),
Dichloromethane solution (oxidation potential measurement)
Reference electrode: Ag / Ag ⁺
Counter electrode: Pt
Working electrode: Glassy carbon voltage insertion speed: 1.0 V / s
Measuring device: ALS model 660C, electrochemical analyzer

  Table 2 shows that the oxidation potential of Comparative Compound 3 is as low as 0.46 V, whereas the oxidation potentials of Exemplified Compounds A1 and C2 according to this embodiment are as high as 0.68 V and 0.69 V, respectively. That is, it means that the compound has a low HOMO energy, and thus is a compound that is hardly oxidized.

  The organic compound according to the present embodiment has a basic skeleton composed of only carbon and does not have a hetero atom such as a nitrogen atom. This also contributes to the low oxidation potential of the compound itself, which is one of the reasons that the organic compound according to this embodiment is stable against oxidation. Therefore, an organic light-emitting device using this compound has high stability and exhibits excellent device durability.

(3) Low crystallinity due to an asymmetric structure The organic compound according to the present embodiment has an increased conjugate length such that the emission wavelength region of the basic skeleton itself is red. In general, a molecule having a long conjugate length has a high molecular planarity, so that the molecular packing becomes strong. Molecular packing is not preferred because it increases crystallinity, lowers sublimability and causes concentration quenching. Molecular packing refers to relatively strong intermolecular interactions. In the present embodiment, this may be referred to as an intermolecular interaction.

  In order to suppress the intermolecular interaction, we focused on the symmetry of the molecular structure. Molecules with low symmetry are more likely to have a disordered molecular arrangement when solidified than molecules with high symmetry, so that molecular packing in which molecules overlap regularly is suppressed.

  In the present embodiment, the symmetry of the molecular structure of the basic skeleton was compared between the exemplified compound A2 according to the present embodiment, the comparative compound 4 and the comparative compound 5 using group theory. Note that Comparative Compound 4 was used for comparison as an example of an organic compound exhibiting highly symmetric red emission. Comparative compound 5 is a compound described in Patent Document 2.

The basic skeleton of Comparative Compound 4 has a twice-rotation axis (C2) perpendicular to the molecular plane, and has a two-fold rotation axis (C2) orthogonal to the two-fold rotation axis and a symmetry plane (σ _h ). because it has, the point group is classified as _{D 2h.}

Basic skeleton of Comparative Compound 5 has a 2-fold axis in the long axis direction of the molecule plane (C2), since it has a plane of symmetry (sigma _v) containing the Dyad, point cloud classified into C _2v Is done.

  On the other hand, the basic skeleton of Exemplified Compound A2 according to the present embodiment does not have a rotation axis and has a symmetry plane (σ) including a molecular plane, and thus the point group is classified as Cs.

  Therefore, the symmetry of the molecule is lower in the order of Comparative compound 4, Comparative compound 5, and Exemplified compound A2.

  Molecules with low symmetry have high sublimability because molecular packing is suppressed and crystallinity is reduced. The sublimability indicates the ease of sublimation of the organic compound, and is defined here as the difference between the thermal decomposition temperature and the sublimation temperature. That is, a high sublimation property means that the sublimation temperature is sufficiently lower than the thermal decomposition temperature, so that even when sublimation purification or the like is performed, the organic compound is not decomposed.

  Exemplified compound A2 is considered to be an organic compound having low sublimation property because Exemplified compound A2 has an increased molecular weight and increased molecular planarity as compared with Comparative compound 4 and Comparative compound 5, but is decomposed even after sublimation. Has not been confirmed. On the other hand, the comparative compound (4) had a low molecular weight itself, but had high symmetry, so that the intermolecular interaction was promoted and the sublimation temperature was raised to near the thermal decomposition temperature of the compound. Therefore, it is considered that decomposition after sublimation was confirmed. Here, the presence or absence of decomposition before and after sublimation is determined by the presence or absence of a decrease in purity after sublimation. The purity was measured using high performance liquid chromatography manufactured by JASCO Corporation.

  As described above, since the organic compound according to the present invention is a molecule having low symmetry, it is possible to suppress molecular packing and maintain sublimability while using a conjugate length having a light emitting region in a long wavelength region as a basic skeleton. It is a compound that can be made.

Further, an organic compound satisfying the following conditions (4) to (6) is preferable as a compound used for an organic light emitting device. This is because, when the conditions (4) to (6) are satisfied, the effect of suppressing the intermolecular interaction is enhanced, and the improvement in sublimability and the concentration quenching can be suppressed. The improvement in sublimability enables the purification of materials by sublimation purification and the production of organic light-emitting devices by vapor deposition. Thus, impurities contained in the organic light emitting element can be reduced, and it is possible to prevent a decrease in luminous efficiency and a decrease in driving durability due to the impurities. Further, suppression of concentration quenching is preferable from the viewpoint of improving the luminous efficiency of the organic light emitting device.
(4) a compound having a bulky substituent at any of R ₉ , R ₁₀ , R ₁₉ and R ₂₀ , (5) having a substituent covering a molecular plane, and (6) a compound having an SP2 hybrid orbital.

  Hereinafter, these will be described.

(4) R ₉ , R ₁₀ , R ₁₉ , and R ₂₀ have a bulky substituent in any one of the organic compounds according to the present embodiment. It is possible to suppress. Suppressing crystallinity leads to suppression of concentration quenching between molecules and improvement in sublimability.

  When a substituent is provided, it is preferable to provide the substituent at a substitution position where the effect of suppressing the interaction between molecules is high.

  Specifically, in the case of an alkyl group, a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, an octyl group, and the like are preferable, and a sterically large isopropyl group and a tertiary butyl group are particularly preferable. In the case of an aryl group, an aryl group such as a phenyl group having a substituent such as a methyl group, a xylyl group, a mesityl group, an isopropyl group, and a tert-butylphenyl group is preferable. Fluorine is also preferred in this regard. In addition, when used in a method of removing the solvent by disposing (applying) it in a liquid at a predetermined position and thereafter removing the solvent, it is preferable to provide a substituent because it leads to improvement in film properties.

  The organic compound according to the present embodiment has high planarity, and when not substituted, excimer is easily generated by molecular packing. Therefore, it is necessary to suppress the generation of excimers, and the position of the substituent that can be effectively suppressed will be described.

Molecular packing, that is, π-π interaction between molecules, increases as the π plane expands. We focused on π electrons, which generate π-π interaction, especially their electron density. Here, the electron density of the basic skeleton was estimated using molecular orbital calculation. As a calculation method of the molecular orbital calculation method, a density functional theory (DFT) widely used at present is used. The functional was B3LYP and the basis function was 6-31G ^* . The molecular orbital calculation method is described in Gaussian 09 (Gaussian 09, Revision C.01, MJ. Frisch, GW Trucks, HB Schlegel, GE Scuseria, MA) which is currently widely used. Robb, JR Cheeseman, G. Scalmani, V. Barone, B. Mennucci, GA A. Petersson, H. Nakatsuji, M. Caricato, X. Li, HP 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, JA Montgomery, Jr., JE Peralta, F. Ogliaro, M. Bearpark, JJ Heyd, E. Brothers, KN Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, JC Burant, SS Iyengar, J. Tomasi, M. Regis, N. Regis. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomberts, R. E. Stratmann, O. Yazyev, A. J. Austi , R. Cami, C. Pomerli, JW Ochterski, RL Martin, K. Morokuma, VG Zakrzewski, GA Voth, P. Salvador, J. J. Dannenberg, S. Dapprich. , AD Daniels, O. Farkas, JB Foresman, JV Ortiz, J. Cioslowski, and DJ J. Fox, Gaussian, Inc., Wallingford CT, 2010.).

The following shows partial charges of carbon atoms in the basic skeleton of the organic compound represented by the general formula [2]. The portion having a high electron density is a carbon atom located at R ₉ , R ₁₀ , R ₁₉ , and R ₂₀ in the general formula [2]. That is, this carbon atom has a high density of π electrons interacting between molecules. As described above, at least one of R ₉ , R ₁₀ , R ₁₉ , and R ₂₀ , which is orthogonal to the basic skeleton and has a high electron density, such as an aryl group or an alkyl group, in order to suppress intramolecular interaction. It is preferable to provide a substituent.

The following shows partial charges of carbon atoms in the basic skeleton of the organic compound represented by the general formula [3]. It can be seen that the portion corresponding to the organic compound represented by the general formula [2] has a high partial charge. Therefore, also in the general formula [3], it is preferable to provide a substituent such as an aryl group or an alkyl group in at least one of R ₉ , R ₁₀ , R ₁₉ , and R ₂₀ .

In the general formula [1], the same partial charge is obtained. Therefore, in the general formula [1], at least one of R ₉ , R ₁₀ , R ₁₉ , and R ₂₀ is a substituent such as an aryl group or an alkyl group. It is preferable to provide a substituent.

  The following is a comparison result of sublimability related to the position where the substituent is provided. Exemplified compound A17 is an organic compound having a smaller molecular weight than Exemplified compound A2. It is estimated that an organic compound having a small molecular weight has a high sublimability. However, since the purity of Exemplified Compound A17 is reduced after sublimation purification, it can be seen that Exemplified Compound A2 is more excellent in sublimability. This is because, as described above, the compound has a bulky substituent at the substitution position that effectively suppresses the intermolecular interaction. On the other hand, Exemplified Compound A17 can be suitably used as a high mobility material for an organic thin film transistor or the like since the center conjugate plane of the basic skeleton is exposed, so that molecules are likely to overlap with each other.

  The same comparison was performed for the exemplified compounds C18 and C3, and the same effect was confirmed.

(5) The organic compound according to the present embodiment having a substituent covering the molecular plane can suppress intermolecular interaction by appropriately selecting the type of the substituent provided in the basic skeleton. Specifically, by introducing a substituent that covers the central conjugate plane of the basic skeleton, the intermolecular interaction can be suppressed. In the organic compound according to the present embodiment, the intermolecular interaction is considered to be promoted by the overlapping of the π-conjugated planes of the basic skeleton. Therefore, an attempt was made to provide a substituent that shields the π-conjugate plane. Specifically, as in the case of Exemplified Compound A2, an attempt was made to cover the π-conjugated plane by providing a methyl group at the ortho position of the phenyl group as a substituent to suppress intermolecular interaction.

  Here, the effects of the substituents are compared using the exemplified compounds A1, A2, and A10. The molecular weight of Exemplified Compound A2 is larger than that of Exemplified Compound A2, but the difference between the thermal decomposition temperature and the sublimation temperature is larger in Exemplified Compound A2. Although A10 has a larger molecular weight, the difference between the thermal decomposition temperature and the sublimation temperature is further larger because the intermolecular interaction is appropriately suppressed.

The greater the temperature difference between the thermal decomposition temperature and the sublimation temperature, the greater the temperature margin in sublimation purification, and thus the more excellent the sublimability. The sublimation temperature was a temperature at which a sufficient sublimation rate was reached at a degree of vacuum of 1 × 10 ^-1 Pa while Ar flow was performed and the temperature was slowly raised to start sublimation purification. The decomposition temperature was measured at the time when TG / DTA measurement was performed and the weight loss reached 5%. Similar comparisons were made for the exemplified compounds C2, C3, and C10, and the same results were obtained.

  Table 5 shows the structural formula, molecular weight, and schematic diagram of the molecule observed from the vertical direction, and the schematic diagram of the molecule observed from the planar direction of each exemplified compound.

  As described above, when the condition (5) is satisfied, the organic compound according to the present embodiment has a wide difference between the sublimation temperature and the thermal decomposition temperature, and is excellent in sublimability.

(6) A compound having an SP2 hybrid orbital The organic compound according to the present embodiment has a basic skeleton having a large conjugate length. For this reason, molecular packing is strong and the sublimation temperature reaches a high temperature. Therefore, it is preferable that the compound be stable even at high temperatures. That is, it is preferable that the thermal stability is high.

  In addition to the fact that the basic skeleton is composed only of carbon atoms of the SP2 hybrid orbital and that the substituent is composed of SP2 hybrid carbon, the stability of the compound is improved.

  Therefore, it is preferable that the whole molecule is composed of SP2 hybrid carbon.

  As described above, since the organic compound according to the present embodiment is a compound having the properties described in (1) to (3) above, the emission wavelength of the basic skeleton itself is red as compared with Comparative Compounds 1 and 2, And it becomes an organic compound maintaining sublimability. Furthermore, by becoming a compound having the properties of (4) to (6), it becomes a compound that suppresses molecular packing and has excellent sublimability. By using this, it is possible to obtain an organic light-emitting element that emits deep red light with high efficiency and high element durability.

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

  Among the above exemplified compounds, Group A is an organic compound represented by the general formula [2], in which the whole molecule is composed of only hydrocarbons. Here, compounds composed of only hydrocarbons generally have a low HOMO energy level, that is, a high oxidation potential. Therefore, it is an organic compound that is stable against oxidation.

  From the above properties, the organic compounds of Group A can be used for the light emitting layer host, the transport layer, and the injection layer.

  Among the above exemplified compounds, Group B is an organic compound having a substituent containing a hetero atom among the organic compounds represented by the general formula [2]. In this case, the oxidation potential of the molecule itself changes significantly. Or the intermolecular interaction changes. The organic compounds of Group B are useful as an electron-transport property, a hole-transport property, and a hole-trapping light-emitting material. In particular, those substituted with fluorine have improved sublimability since the intermolecular interaction is suppressed.

  Among the above exemplified compounds, Group C is an organic compound represented by the general formula [3], the entire molecule of which is composed of only hydrocarbons. Here, compounds composed of only hydrocarbons generally have a low HOMO energy level, that is, a high oxidation potential. Therefore, it is an organic compound that is stable against oxidation.

  From the above properties, the organic compounds of Group A can be used for the light emitting layer host, the transport layer, and the injection layer.

  Among the above exemplified compounds, Group D is an organic compound having a substituent containing a hetero atom among the organic compounds represented by the general formula [3]. In this case, the oxidation potential of the molecule itself changes significantly. Or the intermolecular interaction changes. The organic compounds of Group B are useful as an electron-transport property, a hole-transport property, and a hole-trapping light-emitting material. In particular, those substituted with fluorine have improved sublimability since the intermolecular interaction is suppressed.

Among the above exemplified compounds, Group E is a compound in which R ₁₂ and R ₁₃ form a benzene ring among the organic compounds represented by the general formula [1]. In this case, since the molecular weight of the basic skeleton itself is small and the symmetry of the basic skeleton is low, the compound is excellent in sublimability.

  Next, the organic light emitting device of the present embodiment will be described.

  The organic light-emitting device of the present embodiment has at least an anode and a cathode, which are a pair of electrodes, and an organic compound layer disposed between these electrodes. In the organic light-emitting device of the present embodiment, the organic compound layer may be a single layer as long as it has a light-emitting layer, or may be a laminate including a plurality of layers.

  Here, when the organic compound layer is a laminate composed of a plurality of layers, the organic compound layer, in addition to the light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a charge generation layer, a hole / exciton blocking layer, an electron It may have a transport layer, an electron injection layer, and the like. The light-emitting layer may be a single layer or a stacked body including a plurality of layers.

  In the organic light emitting device of the present embodiment, at least one of the organic compound layers contains the organic compound according to the present embodiment. Specifically, the organic compound according to the present embodiment may be any of the above-described light emitting layer, hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole / exciton blocking layer, electron transport layer, electron injection layer, etc. Crab included. The organic compound according to the present embodiment is preferably contained in the light emitting layer.

  In the organic light emitting device of the present embodiment, when the organic compound according to the present embodiment is included in the light emitting layer, the light emitting layer may be a layer composed of only the organic compound according to the present embodiment, A layer composed of such an organic compound and another compound may be used. Here, when the light emitting layer is a layer composed of the organic compound according to the present embodiment and another compound, the organic compound according to the present embodiment may be used as a host of the light emitting layer or used as a guest. You may. Further, it may be used as an assist material that can be included in the light emitting layer.

  Here, the host is a compound having the largest weight ratio among the compounds constituting the light emitting layer. The guest is a compound having a smaller weight ratio than that of the host among the compounds constituting the light-emitting layer, and is a compound that mainly emits light. The assist material is a compound that has a weight ratio smaller than that of the host among the compounds constituting the light emitting layer and assists the light emission of the guest. Note that the assist material is also called a second host. When the composition of the light emitting layer of the organic light emitting element is considered to be uniform, it can be regarded as the composition of the entire light emitting layer by analyzing a part of the light emitting layer.

  Here, when the organic compound according to the present embodiment is used as a guest of the light emitting layer, the concentration of the guest is preferably 0.01% by weight or more and 20% by weight or less based on the whole light emitting layer, and 0.1% by weight. % Or more and 5.0% by weight or less.

  When the organic compound according to this embodiment is used as a guest of a light-emitting layer, a material having a higher LUMO than the organic compound according to this embodiment (a material whose LUMO is closer to a vacuum level) is preferably used as a host. This is because the organic compound according to the present embodiment has a low LUMO. By using a material having a higher LUMO than the organic compound according to the present embodiment as a host, electrons supplied to the host of the light-emitting layer can be used in the present embodiment. This is because such an organic compound can be more received.

  The present inventors have conducted various studies, the organic compound according to the present embodiment as a host or guest of the light-emitting layer, especially when used as a guest of the light-emitting layer, exhibits a high-efficiency and high-luminance light output, and It has been found that an element having extremely high durability can be obtained. The light-emitting layer may be a single layer or a multi-layer, or can include a light-emitting material having another light-emitting color to be mixed with red light, which is the light-emitting color of this embodiment. The multilayer means a state in which a light emitting layer and another light emitting layer are stacked. In this case, the emission color of the organic light emitting element is not limited to red. More specifically, the color may be white or an intermediate color. In the case of white, another light emitting layer emits a color other than red, that is, blue or green. In addition, a film is formed by vapor deposition or coating. This will be described in detail in an embodiment described later.

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

  Here, in addition to the organic compound according to the present embodiment, if necessary, conventionally known low-molecular and high-molecular hole-injecting compounds or hole-transporting compounds, compounds serving as hosts, luminescent compounds, and electron-injecting compounds Compounds or electron transporting compounds can be used together.

  Examples of these compounds will be described below. As the hole injecting / transporting material, a material having high hole mobility is preferable so that holes can be easily injected from the anode and the injected holes can be transported to the light emitting layer. Further, in order to suppress deterioration of film quality such as crystallization in the organic light emitting device, a material having a high glass transition temperature is preferable. Examples of low-molecular and high-molecular materials having hole injecting and transporting performance include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly (vinylcarbazole), poly (thiophene), and others. Conductive polymers can be used. Further, the above-described hole injecting and transporting material is also suitably used for an electron blocking layer.

  Hereinafter, specific examples of the compound used as the hole injecting and transporting material are shown, but are not limited thereto.

  As a light-emitting material mainly relating to a light-emitting function, in addition to the organic compound represented by the general formula [1], a condensed ring compound (for example, a fluorene derivative, a naphthalene derivative, a pyrene derivative, a perylene derivative, a tetracene derivative, an anthracene derivative, or 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 poly (phenylenevinylene) derivatives And high molecular derivatives such as poly (fluorene) derivatives and poly (phenylene) derivatives.

  The organic compound according to the present embodiment is a compound having a narrow band gap and low HOMO energy and LUMO energy. Therefore, when a mixed layer with another light-emitting material is formed or when a light-emitting layer is stacked, it is preferable that the other light-emitting materials also have low HOMO energy and LUMO energy. This is because when the HOMO / LUMO energy is high, there is a possibility that a quench component or a trap level, such as formation of an exciplex with the organic compound of the present invention, may be formed.

  Hereinafter, specific examples of the compound used as the light emitting material are shown, but are not limited thereto.

  Examples of the light emitting layer host or light emitting assisting material contained in the light emitting layer include aromatic hydrocarbon compounds or derivatives thereof, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organic aluminum complexes such as tris (8-quinolinolate) aluminum, organic Beryllium complex and the like.

  Since the organic compound according to this embodiment has a narrow band gap and a low HOMO / LUMO energy, it is preferable that the host material is also formed of a hydrocarbon and the HOMO / LUMO energy is low. This is because, when the host material contains a hetero atom such as a nitrogen atom, the HOMO / LUMO energy becomes high, and there is a possibility that a quench component or a trap level, such as the formation of an exciplex with the organic compound according to the present embodiment, may be formed. Because there is.

  Particularly preferably, the host material preferably has an anthracene, tetracene, perylene, or pyrene skeleton in a molecular skeleton. This is because, in addition to being composed of hydrocarbon as described above, the organic compound of the present invention has S1 energy capable of causing sufficient energy transfer.

  Hereinafter, specific examples of the compound used as the light emitting layer host or the light emitting assisting material included in the light emitting layer are shown, but are not limited thereto.

  The electron transporting material can be arbitrarily selected from those capable of transporting 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 transporting material and the like. . Examples of the material having an electron transporting property include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organic aluminum complexes, and fused compounds (for example, fluorene derivatives, naphthalene derivatives, Chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above-mentioned electron transporting material is also suitably used for a hole blocking layer.

  Hereinafter, specific examples of the compound used as the electron-transporting material are shown, but are not limited thereto.

[Configuration of organic light emitting device]
The organic light-emitting element is provided by forming an anode, an organic compound layer, and a cathode on a substrate. A protective layer, a color filter, and the like may be provided on the cathode. When a color filter is provided, a flattening layer is preferably provided.

  Examples of the substrate include quartz, glass, silicon wafer, resin, and metal. Further, a switching element such as a transistor and a wiring may be provided over the substrate, and an insulating layer may be provided thereover. As the insulating layer, any material can be used as long as a contact hole can be formed in order to secure conduction between the anode 2 and the wiring, and if insulation with an unconnected wiring can be ensured. For example, a resin such as polyimide, silicon oxide, silicon nitride, or the like can be used.

  As a constituent material of the anode, a material having a work function as large as possible is preferable. For example, simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, and mixtures containing these, or alloys thereof, tin oxide, zinc oxide, indium oxide, and tin oxide Metal oxides such as indium (ITO) and indium zinc oxide can be used. Also, conductive polymers such as polyaniline, polypyrrole, and polythiophene can be used.

  One of these electrode substances may be used alone, or two or more thereof may be used in combination. Further, the anode may be composed of one layer, or may be composed of a plurality of layers.

  When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, an alloy thereof, a layered material thereof, or the like can be used. When used as a transparent electrode, an oxide transparent conductive layer of indium tin oxide (ITO), indium zinc oxide, or the like can be used, but it is not limited thereto. Photolithography technology can be used to form the poles.

  On the other hand, the constituent material of the cathode preferably has a small work function. For example, an alkali metal such as lithium, an alkaline earth metal such as calcium, a simple metal such as aluminum, titanium, manganese, silver, lead, and chromium, or a mixture containing these can be used. Alternatively, an alloy obtained by combining these metals alone can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver and the like can be used. It is also possible to use a metal oxide such as indium tin oxide (ITO). One of these electrode substances may be used alone, or two or more thereof may be used in combination. The cathode may have a single-layer structure or a multilayer structure.

  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. Although there is no particular limitation on the method for forming the cathode, it is more preferable to use a direct current or alternating current sputtering method because the film has good coverage and resistance can be easily reduced.

  After forming the cathode, a sealing member (not shown) may be provided. For example, by adhering a glass provided with a moisture absorbent on the cathode, it is possible to suppress entry of water or the like into the organic EL layer, and to suppress occurrence of display defects. Further, as another embodiment, a passivation film such as silicon nitride may be provided on the cathode to suppress entry of water or the like into the organic EL layer. For example, after the cathode 7 is formed, the protective layer may be transferred to another chamber without breaking the vacuum and a 2 μm-thick silicon nitride film is formed by a CVD method.

  Further, a color filter may be provided for each pixel. For example, a color filter corresponding to the size of a pixel may be provided on another substrate, and the color filter may be attached to a substrate provided with an organic EL element. The color filters may be patterned.

  The organic compound layers (the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer, the electron injection layer, etc.) constituting the organic light emitting device according to the present embodiment are as follows. It is formed by the method shown.

  The organic compound layer constituting the organic light emitting device according to the present embodiment can use a dry process such as a vacuum evaporation method, an ionization evaporation method, sputtering, and plasma. Instead of the dry process, a wet process of forming a layer by a known coating method (for example, spin coating, dipping, casting, LB method, inkjet method, etc.) by dissolving in a suitable solvent can also be used.

  Here, when a layer is formed by a vacuum evaporation method, a solution coating method, or the like, crystallization or the like hardly occurs, and the stability with time is excellent. When the film is formed by a coating method, the film can be formed in combination with an appropriate binder resin.

  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, and the like. .

  These binder resins may be used alone as a homopolymer or a copolymer, or may be used as a mixture of two or more. If necessary, known additives such as a plasticizer, an antioxidant, and an ultraviolet absorber may be used in combination.

(Use 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 constituent member of a display device or a lighting device. There are also other uses such as an exposure light source for an electrophotographic image forming apparatus, a backlight for a liquid crystal display, and a light emitting device having a white light source with a color filter.

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

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

  Next, the display device according to the present embodiment will be described with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing an example of a display device having an organic light emitting element and a TFT element connected to the organic light emitting element. A TFT element is an example of an active element.

  The display device 10 shown in FIG. 1 includes a substrate 11 made of glass or the like, and a moisture-proof film 12 for protecting a TFT element or an organic compound layer on the substrate 11. Reference numeral 13 denotes a metal gate electrode 13. Reference numeral 14 denotes a gate insulating film 14, and 15 denotes a semiconductor layer.

  The TFT element 18 has a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on the TFT element 18. The anode 21 and the source electrode 17 constituting the organic light emitting device are connected via the contact hole 20.

  Note that the method of electrical connection between the electrodes (anode and cathode) included in the organic light emitting element and the electrodes (source and drain electrodes) included in the TFT is not limited to the mode illustrated in FIG. That is, any one of the anode and the cathode may be electrically connected to either the source electrode or the drain electrode of the TFT element.

  Although the organic compound layer is illustrated as one layer in the display device 10 of FIG. 1, the organic compound layer 22 may be a plurality of layers. On the cathode 23, a first protective layer 24 and a second protective layer 25 for suppressing the deterioration of the organic light emitting element are provided.

  Although the display device 10 of FIG. 1 uses a transistor as a switching element, an MIM element may be used as a switching element instead.

  The transistor used in the display device 10 of FIG. 1 is not limited to a transistor using a single crystal silicon wafer, but 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-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon; and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Note that the thin film transistor is also called a TFT element.

  The transistor included in the display device 10 of FIG. 1 may be formed in a substrate such as a Si substrate. Here, being formed in a substrate means that a transistor is manufactured by processing a substrate itself such as a Si substrate. That is, having a transistor in a substrate can be regarded as a case where the substrate and the transistor are formed integrally.

  Whether a transistor is provided in a substrate is selected depending on definition. For example, in the case of 1 inch and a definition of about QV green A, it is preferable to provide a transistor in a Si substrate.

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

  The display device according to the present embodiment may be used for a display unit of an imaging device that includes an optical unit having a plurality of lenses and an image sensor that receives light passing through the optical unit. The imaging device may include a display unit that displays information acquired by the imaging device. Further, the display unit may be a display unit exposed to the outside of the imaging device or a display unit arranged in a viewfinder. The imaging device may be a digital camera or a digital video camera.

  FIG. 3A is a schematic diagram illustrating an example of the imaging device according to the present embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may include the display device according to the present embodiment. In that case, the display device may display not only the image to be captured but also environment information, an imaging instruction, and the like. The environmental information may include the intensity of the external light, the direction of the external light, the moving speed of the subject, the possibility that the subject is blocked by a blocking object, and the like.

  Since the timing suitable for imaging is a short time, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light emitting device of the present invention. This is because the organic light emitting device has a high response speed. A display device using an organic light emitting element can be used more favorably than these devices and liquid crystal display devices that require a display speed.

  The imaging device 1100 has an optical unit (not shown). The optical unit has a plurality of lenses, and forms an image on an imaging element housed in the housing 1104. The focus of the plurality of lenses can be adjusted by adjusting their relative positions. This operation can be performed automatically.

  The display device according to the present embodiment may include a color filter having red, green, and blue colors. In the color filters, the red, green, and blue colors may be arranged in a delta arrangement.

  The display device according to the present embodiment may be used for a display unit of a mobile terminal. In that case, both the display function and the operation function may be provided. Examples of the mobile terminal include a mobile phone such as a smartphone, a tablet, and a head-mounted display.

  FIG. 3B is a schematic diagram illustrating an example of the electronic device according to the embodiment. The electronic device 1200 includes a display portion 1201, an operation portion 1202, and a housing 1203. The housing 1203 may include a circuit, a printed circuit board including the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit may be a biometric recognition unit that recognizes a fingerprint and unlocks the lock. An electronic device having a communication unit can also be referred to as a communication device.

  FIG. 4 is a schematic diagram illustrating an example of the display device according to the present embodiment. FIG. 10A shows a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301 and a display portion 1302. The light emitting device according to this embodiment may be used for the display unit 1302.

  It has a frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. The lower side of the frame 1301 may also serve as a base.

  Further, the frame 1301 and the display portion 1302 may be bent. The radius of curvature may be 5000 mm or more and 6000 mm or less.

  FIG. 4B is a schematic diagram illustrating another example of the display device according to the present embodiment. The display device 1310 in FIG. 4B is configured to be bendable, and is a so-called folderable display device. The display device 1310 includes a first display portion 1311, a second display portion 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include the light emitting device according to the embodiment. The first display unit 1311 and the second display unit 1312 may be one seamless display device. The first display unit 1311 and the second display unit 1312 can be separated by a bending point. The first display unit 1311 and the second display unit 1312 may display different images, respectively, or may display one image with the first and second display units.

  FIG. 5A is a schematic diagram illustrating an example of a lighting device according to the present embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, an optical film 1404, and a light diffusion unit 1405. The light source may include the organic light emitting device according to the embodiment. The optical filter may be a filter that improves the color rendering of the light source. The light diffusing unit can effectively diffuse light from a light source such as light-up and deliver light to a wide range. The optical filter and the light diffusion unit may be provided on the light emission side of the illumination. If necessary, a cover may be provided on the outermost side.

  The lighting device is, for example, a device that illuminates a room. The lighting device may emit white, neutral white, or any other color from blue to red. It may have a dimming circuit for dimming them. The lighting device may include the organic light emitting device of the present invention and a power supply circuit connected thereto. The power supply circuit is a circuit that converts an AC voltage into a DC voltage. White has a color temperature of 4200K and neutral white has a color temperature of 5000K. The lighting device may have a color filter.

  In addition, the lighting device according to the present embodiment may include a heat radiating unit. The heat radiating section is for radiating heat inside the apparatus to the outside of the apparatus, and examples thereof include a metal having a high specific heat and liquid silicon.

  FIG. 5B is a schematic diagram of an automobile as an example of the moving object according to the present embodiment. The vehicle has a tail lamp which is an example of a lamp. The automobile 1500 may have a tail lamp 1501 and turn on the tail lamp when a brake operation or the like is performed.

  The tail lamp 1501 may include the organic light emitting device according to the embodiment. The tail lamp may have a protection member for protecting the organic EL element. The material of the protective member is not limited as long as it has a certain high strength and is transparent, but is preferably made of polycarbonate or the like. A polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

  Automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window may be a transparent display as long as it is not a window for confirming the front and rear of the vehicle. The transparent display may include the organic light emitting device according to the embodiment. In this case, a constituent material such as an electrode of the organic light emitting element is formed of a transparent member.

  The moving object according to the present embodiment may be a ship, an aircraft, a drone, or the like. The moving body may include a body and a lamp provided on the body. The lamp may emit light for indicating the position of the aircraft. The lamp has the organic light emitting device according to the present embodiment.

  In the organic light emitting element according to the present embodiment, the light emission luminance is controlled by a TFT which is an example of a switching element, and an image can be displayed with each light emission luminance by providing the organic light emitting element on a plurality of surfaces. The switching element according to the present embodiment is not limited to a TFT, and may be a transistor formed of low-temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. On the substrate can also be referred to as within the substrate. This is selected depending on the definition. For example, in the case of a definition of about 1 inch and QVGA, it is preferable to provide an organic light emitting element on a Si substrate. By driving the display device using the organic light emitting device according to the present embodiment, stable display can be performed with good image quality and long-time display.

  Hereinafter, the present invention will be described with reference to examples. However, the present invention is not limited to these.

  Example 1 Synthesis of Exemplified Compound A2

(1) Synthesis of Compound F3 The following reagents and solvent were placed in a 200 ml eggplant flask.
Compound E1: 4.35 g (10 mmol)
Compound E2: 3.28 g (10 mmol)
Pd (PPh ₃ ) ₄ : 0.2 g
Toluene: 50ml
Ethanol: 20ml
2M-sodium carbonate aqueous solution: 50 ml

  Next, the reaction solution was heated to 80 ° C. under a nitrogen stream and stirred at this temperature (80 ° C.) for 6 hours. After completion of the reaction, water was added to carry out liquid separation, dissolved in chloroform, purified by column chromatography (chloroform), and then recrystallized from chloroform / methanol to obtain a dark green compound E3. Was obtained in an amount of 4.17 g (yield: 75%).

(2) Synthesis of Compound F5 The following reagents and solvent were charged into a 100-ml eggplant flask.
Compound E3: 3.90 g (7 mmol)
Compound E4: 2.25 g (9 mmol)
Isoamyl nitrite: 1.05 g (9 mmol)
Toluene: 40 ml

  Next, the reaction solution was heated to 110 ° C. under a nitrogen stream and stirred at this temperature (80 ° C.) for 3 hours. After the completion of the reaction, the resultant was washed twice with 40 ml of water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give a brown liquid. This was purified by column chromatography (chloroform / heptane = 1: 4) and then recrystallized from chloroform / methanol to obtain 4.27 g (yield: 85%) of yellow crystal E5.

(3) Synthesis of Compound F6 The following reagents and solvent were charged into a 500 ml reaction vessel.
Compound E5: 3.59 g (5 mmol)
Trifluoroacetic acid: 30 ml
Methylene chloride: 300ml

Next, the following reagents were placed in a reaction vessel under a water bath.
BF ₃ · OEt: 9ml

  Next, after stirring the reaction solution for about 10 minutes, 2.5 g of DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone, 11 mmol) was added. Next, after stirring the reaction solution for 10 minutes, 2.1 g (11 mmol) of ferrocene was added in a water bath at 20 degrees. After stirring for about 5 minutes, 300 ml of methanol was added. The red precipitate generated at this time was filtered to obtain a red solid. Next, this solid was dissolved in chlorobenzene and recrystallized from heptane to obtain 3.2 g (yield: 90%) of red crystal F6.

(4) Synthesis of Compound F8 The following reagents and solvents were charged into a 200 ml eggplant flask.
Compound E6: 2.15 g (3 mmol)
Compound E7: 0.57 g (3.3 mmol)
Pd (PPh ₃ ) ₄ : 0.6 g
Toluene: 100ml
Ethanol: 10ml
2M-sodium carbonate aqueous solution: 30 ml

  Next, the reaction solution was heated to 80 ° C. under a nitrogen stream, and stirred at this temperature (80 ° C.) for 8 hours. After completion of the reaction, ethanol was added to precipitate crystals, and the crystals were separated by filtration and dispersed and washed sequentially with water, ethanol and heptane. Next, the obtained crystals were dissolved by heating in chlorobenzene, filtered after heating, and then recrystallized to obtain 1.76 g (yield: 77%) of a red compound F8.

(5) Synthesis of Exemplified Compound A2 The following reagents and solvents were charged into a 20 ml eggplant flask.
Compound F8: 763 mg (1 mmol)
Pd (dba) ₂ : 238 mg
P (Cy) ₃ (tricyclohexylphosphine): 280 mg
DBU (diazabicycloundecene): 0.15 ml
DMF: 5ml

  Next, the reaction solution was heated to 145 ° C. under a nitrogen stream and stirred at this temperature (145 ° C.) for 6 hours. After completion of the reaction, ethanol was added to precipitate crystals, and the crystals were separated by filtration and dispersed and washed sequentially with water, ethanol and heptane. Next, the obtained purple crystals were dissolved in toluene by heating, and then filtered while hot and recrystallized with toluene / methanol to obtain 0.57 g (yield: 78%) of dark red exemplary compound A2. .

  The purity of this compound was confirmed to be 99% or more using HPLC.

  The exemplary compound A2 was subjected to mass spectrometry using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained value: m / z = 828.85 Calculated value: C ₅₈ H ₃₀ = 828.99

Example 2 Synthesis of Exemplified Compound A7 A method similar to that of Example 1 except that the compound F9 shown below was used instead of the compound F1 and the compound F10 shown below was used instead of the compound F2 in Example 1. As a result, Exemplified Compound A7 was obtained.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 1081.43 _Calculated: C ₈₄ H 73 = 1081.47

Example 3 Synthesis of Exemplified Compound A8 In Example 1, the following compound F11 was used instead of compound F1, compound F12 shown below was used instead of compound F2, and compound F13 shown below was used instead of compound F7. Except for using it, Exemplified compound A8 was obtained in the same manner as in Example 1.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 1194.02 _Calculated: C ₉₂ H 88 = 1193.68

Example 4 Synthesis of Exemplified Compound A10 A method similar to that of Example 1 except that the compound F14 shown below was used instead of the compound F1 and the compound F15 shown below was used instead of the compound F2 in Example 1. As a result, Exemplified Compound A10 was obtained.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 97% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained value: m / z = 877.32 Calculated value: C ₇₀ H ₃₆ = 877.03

Example 5 Synthesis of Exemplified Compound A31 In Example 1, compound F16 shown below was used instead of compound F1, compound F17 shown below was used instead of compound F2, and compound F18 shown below was used instead of compound F7. Except for using it, Exemplified compound A31 was obtained in the same manner as in Example 1.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained: m / z = 953.52 Calculated: C ₇₆ H ₄₀ = 953.13

Example 6 Synthesis of Exemplified Compound A38 A method similar to that of Example 1 except that the compound F16 shown below was used instead of the compound F1 and the compound F17 shown below was used instead of the compound F2 in Example 1. As a result, Exemplified Compound A38 was obtained.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 1029.39 _Calculated: C ₈₂ H 44 = 1029.23

Example 7 Synthesis of Exemplified Compound A45 A method similar to that of Example 1 except that the following compound F18 was used instead of compound F2 and the following compound F19 was used instead of compound F7 in Example 1. As a result, Exemplified Compound A45 was obtained.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 1209.05 _Calculated: C ₉₆ H 56 = 1209.47

Example 8 Synthesis of Exemplified Compound B2 Exemplified compound B2 was obtained in the same manner as in Example 1, except that Compound F20 shown below was used instead of Compound F1.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 97% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained: m / z = 836.08 Calculated: C ₆₄ H ₃₀ F ₂ = 836.92

Example 9 Synthesis of Exemplified Compound B7 A method similar to that of Example 1 except that the compound F21 shown below was used instead of the compound F1 and the compound F22 shown below was used instead of the compound F7 in Example 1. Afforded Exemplified Compound B7.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained: m / z = 968.34 Calculated: C ₇₆ H ₄₁ N = 968.15

Example 10 Synthesis of Exemplified Compound A52 A method similar to that of Example 1 except that the following compound F23 was used instead of compound F3 and the following compound F24 was used instead of compound F7 in Example 1. Afforded Exemplified Compound B7.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 877.34 _Calculated: C ₇₀ H 36 = 877.03

  Example 11 Synthesis of Exemplified Compound C2

(1) Synthesis of Compound G3 The following reagents and solvent were placed in a 200 ml eggplant flask.
Compound G1: 4.35 g (10 mmol)
Compound G2: 3.28 g (10 mmol)
Pd (PPh ₃ ) ₄ : 0.2 g
Toluene: 50ml
Ethanol: 20ml
2M-sodium carbonate aqueous solution: 50 ml

  Next, the reaction solution was heated to 80 ° C. under a nitrogen stream and stirred at this temperature (80 ° C.) for 6 hours. After completion of the reaction, water was added to carry out liquid separation, dissolved in chloroform, purified by column chromatography (chloroform), and then recrystallized from chloroform / methanol to obtain a dark green compound G3. 4.17 g (yield: 75%) was obtained.

(2) Synthesis of Compound G5 The following reagents and solvent were charged into a 100-ml eggplant flask.
Compound G3: 3.90 g (7 mmol)
Compound G4: 2.25 g (9 mmol)
Isoamyl nitrite: 1.05 g (9 mmol)
Toluene: 40 ml

  Next, the reaction solution was heated to 110 ° C. under a nitrogen stream and stirred at this temperature (80 ° C.) for 3 hours. After the completion of the reaction, the resultant was washed twice with 40 ml of water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give a brown liquid. This was purified by column chromatography (chloroform / heptane = 1: 4) and then recrystallized from chloroform / methanol to obtain 4.27 g (yield: 85%) of yellow crystal G5.

(3) Synthesis of Compound G6 The following reagents and solvent were charged into a 500 ml reaction vessel.
Compound G5: 3.59 g (5 mmol)
Trifluoroacetic acid: 30 ml
Methylene chloride: 300ml

Next, the following reagents were placed in a reaction vessel under a water bath.
BF ₃ · OEt: 9ml

  Next, after stirring the reaction solution for about 10 minutes, 2.5 g of DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone, 11 mmol) was added. Next, after stirring the reaction solution for 10 minutes, 2.1 g (11 mmol) of ferrocene was added in a water bath at 20 degrees. After stirring for about 5 minutes, 300 ml of methanol was added. The red precipitate generated at this time was filtered to obtain a red solid. Next, this solid was dissolved in chlorobenzene and recrystallized from heptane to obtain 3.2 g (yield: 90%) of red crystal G6.

(4) Synthesis of Compound G8 The following reagents and solvent were charged into a 200-ml eggplant flask.
Compound G6: 2.15 g (3 mmol)
Compound G7: 1.08 g (3.3 mmol)
Pd (PPh ₃ ) ₄ : 0.6 g
Toluene: 100ml
Ethanol: 10ml
2M-sodium carbonate aqueous solution: 30 ml

  Next, the reaction solution was heated to 80 ° C. under a nitrogen stream, and stirred at this temperature (80 ° C.) for 8 hours. After completion of the reaction, ethanol was added to precipitate crystals, and the crystals were separated by filtration and dispersed and washed sequentially with water, ethanol and heptane. Next, the obtained crystals were dissolved in chlorobenzene by heating, filtered under hot conditions and then recrystallized to obtain 1.88 g (yield: 75%) of a red compound G8.

(5) Synthesis of Exemplified Compound C2 The following reagents and solvents were charged into a 20 ml eggplant flask.
Compound G8: 837 mg (1 mmol)
Pd (dba) ₂ : 238 mg
P (Cy) ₃ (tricyclohexylphosphine): 280 mg
DBU (diazabicycloundecene): 0.15 ml
DMF: 5ml

  Next, the reaction solution was heated to 145 ° C. under a nitrogen stream and stirred at this temperature (145 ° C.) for 6 hours. After completion of the reaction, ethanol was added to precipitate crystals, and the crystals were separated by filtration and dispersed and washed sequentially with water, ethanol and heptane. Next, the obtained purple crystal was heated and dissolved in toluene, and then filtered while hot and recrystallized with toluene / methanol to obtain 0.61 g (yield: 76%) of dark red exemplary compound A2. .

  The purity of this compound was confirmed to be 99% or more using HPLC.

  The exemplified compound C2 was subjected to mass spectrometry using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained value: m / z = 800 Calculated value: C ₅₈ H ₃₀ = 801

Example 12 Synthesis of Exemplified Compound C3 Exemplified compound C3 was obtained in the same manner as in Example 11, except that Compound G9 shown below was used instead of Compound G1.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 828 _Calculated: C ₇₈ H 70 = 829

Example 13 Synthesis of Exemplified Compound C4 Exemplified Compound C4 was obtained in the same manner as in Example 11, except that Compound G10 shown below was used instead of Compound G1.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 828 _Calculated: C ₇₈ H 70 = 829

Example 14 Synthesis of Exemplified Compound C6 A method similar to that of Example 11 except that the compound G1 shown below was used instead of the compound G1 and the compound G10 shown below was used instead of the compound G2 in Example 11. Afforded exemplary compound C6.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 1081 _Calculated: C ₇₈ H 70 = 1081

Example 15 Synthesis of Exemplified Compound C7 Exemplified compound C7 was obtained in the same manner as in Example 11, except that Compound G13 shown below was used instead of Compound G2.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 97% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained value: m / z = 876 Calculated value: C ₆₄ H ₄₂ = 877

Example 16 Synthesis of Exemplified Compound C8 The procedure of Example 11 was repeated, except that the compound F14 shown below was used instead of the compound G2, and the compound F14 shown below was used instead of the compound G7. Exemplary compound C8 was obtained by the method.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 97% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained value: m / z = 952 Calculated value: C ₆₄ H ₄₂ = 953

Example 17 Synthesis of Exemplified Compound C9 Exemplified compound C9 was obtained in the same manner as in Example 11, except that Compound G15 shown below was used instead of Compound G2.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 97% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained value: m / z = 952 Calculated value: C ₆₄ H ₄₂ = 953

Example 18 Synthesis of Exemplified Compound C10 Exemplified compound A10 was obtained in the same manner as in Example 11, except that Compound G16 shown below was used instead of Compound G1.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 97% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained value: m / z = 876 Calculated value: C ₆₄ H ₄₂ = 877

Example 19 Synthesis of Exemplified Compound C11 A method similar to that of Example 11 except that the following compound F17 was used instead of compound F1 and the following compound F18 was used instead of compound F2 in Example 11: Afforded exemplary compound C11.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 97% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Obtained value: m / z = 952 Calculated value: C ₆₄ H ₄₂ = 953

Example 20 Synthesis of Exemplified Compound C13 A method similar to that of Example 11 except that the compound G1 shown below was used instead of the compound G1 and the compound G20 shown below was used instead of the compound G2 in Example 11. Afforded exemplary compound C13.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 97% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 932 _Calculated: C ₆₄ H 42 = 933

Example 21 Synthesis of Exemplified Compound C26 A method similar to that of Example 11 except that the following compound G21 was used in place of compound G1 and compound G22 shown below was used instead of compound G2 in Example 11. As a result, Exemplified Compound C26 was obtained.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 988 _Calculated: C ₇₂ H 50 = 989

Example 22 Synthesis of Exemplified Compound C31 A method similar to that of Example 11 except that, in Example 11, the following compound G23 was used instead of the compound G2 and the following compound G24 was used instead of the compound G7. Afforded exemplary compound C31.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 1181 _Calculated: C ₈₈ H 50 = 1181

Example 23 Synthesis of Exemplified Compound D2 Exemplified compound D2 was obtained in the same manner as in Example 11, except that Compound G25 shown below was used instead of Compound G1.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 97% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 836 _{Calculated: C 58 H 26 F 4 =} 837

Example 24 Synthesis of Exemplified Compound D7 A method similar to that of Example 11 except that, in Example 11, the following compound G26 was used instead of the compound G1, and the following compound G27 was used instead of the compound G7. Afforded exemplary compound D7.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 995 _Calculated: C ₇₂ H 43 N = 996

Example 25 Synthesis of Exemplified Compound G1 Exemplified compound G1 was obtained in the same manner as in Example 11, except that Compound G28 shown below was used instead of Compound G7.

  When the purity of the obtained compound was evaluated using HPLC, it was confirmed that the purity was 98% or more.

  Further, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[MALDI-TOF-MS]
Found: m / z = 995 _Calculated: C ₇₂ H 43 N = 996

[Example 26]
In this example, an organic light emitting device having a configuration shown in Table 6 was manufactured. On a substrate, an anode, a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a light emitting layer (EML), a hole blocking layer (HBL), an electron transport layer (ETL), An organic light emitting device having a bottom emission structure in which an electron injection layer (EIL) and a cathode were sequentially formed was manufactured.

The light emitting layer includes a host and a guest. The weight ratio of each is
Host: Guest = 99.5: 0.5
It is.

An ITO electrode (anode) was formed by forming an ITO film on a glass substrate and performing a desired patterning process. At this time, the thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed as described above was used as an ITO substrate in the following steps. Next, vacuum evaporation was performed by resistance heating in a vacuum chamber of 1.33 × 10 ⁻⁴ Pa to continuously form an organic light emitting layer and an electrode layer shown in Table 6 below on the ITO substrate. At this time, the electrode area of the facing electrode (metal electrode layer, cathode) was set to 3 mm ² .

The characteristics of the obtained device were measured and evaluated. The maximum emission wavelength of the light-emitting element was 615 nm, and red light emission of (X, Y) = (0.66, 0.33) was obtained. Specifically, the measurement device measured the current-voltage characteristics with a microammeter 4140B manufactured by Hewlett-Packard Company, and the emission luminance was measured with BM7 manufactured by Topcon Corporation. Further, a continuous driving test was performed at a current density of 100 mA / cm ² , and the time when the luminance deterioration rate reached 5% was measured. Table 7 shows the results of the measurement together with the results of the other examples.

[Examples 27 to 39, Comparative Example 1]
An organic light-emitting device was produced in the same manner as in Example 11, except that the organic compound in Example 26 was appropriately changed to the compounds shown in Table 7. However, in Examples 34 to 39, the thickness of the hole injection layer was changed to 5 nm, and the thickness of the hole transport layer was changed to 25 nm. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 11. Table 7 shows the measurement results.

  From Table 7, the emission color of the organic light-emitting device using Comparative Compound 1 was yellow. This is due to the fact that the guest is Comparative Compound 1 having emission characteristics in the yellow region. On the other hand, the device using the organic compound according to the present invention exhibited good red light emission characteristics.

  Table 8 shows the 5% deterioration life of Examples 26 to 33. The other examples also exhibited the same life. The 5% deterioration life of Comparative Example 1 was 450 hours.

  Table 9 shows chromaticity coordinates of Examples 34 to 39. The organic light-emitting device using Comparative Compound 2 and the organic light-emitting device using Comparative Compound 3 had lower color purity than the values shown in Table 9 below. Comparing the device of the example using the organic compound according to the present embodiment in the red light emitting layer with the device of the comparative example using the comparative compound in the red light emitting layer, the device of the example has a color reproduction range of BT-2020. It can be seen that this is the direction in which the color reproduction range is further expanded. These differences result from using the organic compound according to the present embodiment.

[Example 40]
In this embodiment, an anode, a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a first light emitting layer (1st EML), a second light emitting layer (2nd EML), An organic EL device having a top emission structure in which a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL) and a cathode were sequentially formed.

The first light emitting layer includes a first host, a first guest, and a third guest. The first guest is a red light emitting material and the third guest is a green light emitting material. The weight ratio in the first light emitting layer is
First host: First guest: Third guest = 96.5: 0.5: 3.0
It is.

The second light emitting layer contains a second host and a second guest. The second guest is a blue light emitting material. The weight ratio in the second light emitting layer is
Second host: second guest = 99.4: 0.6
It is.

The cathode contains Ag and Mg. The weight ratio of the components constituting the cathode is
Ag: Mg = 1: 1
It is.

A 40 nm Ti film was formed on a glass substrate by a sputtering method, and was patterned using a photolithography technique to form an anode. At this time, the electrode area of the facing electrode (metal electrode layer, cathode) was set to 3 mm ² .

Subsequently, the substrate and the material on which the electrodes having been cleaned were formed were attached to a vacuum evaporation apparatus (manufactured by ULVAC, Inc.), and after evacuation to 1.33 × 10 ⁻⁴ Pa (1 × 10 ⁻⁶ Torr), UV / ozone was applied. Washing was performed. Thereafter, each layer was formed with the layer configuration shown in Table 10 below, and finally, sealing was performed in a nitrogen atmosphere.

The characteristics of the obtained device were measured and evaluated. All of the obtained devices exhibited good white light emission. Further, a continuous driving test was performed at an initial luminance of 2000 cd / m ² , and the luminance deterioration rate after 100 hours had elapsed was measured. From the obtained white emission spectrum, the chromaticity coordinates of red after passing through the RGB color filter were estimated, and compared with the chromaticity coordinates of red in sRGB (0.64, 0.33). The results are shown in Table 11 together with other examples.

[Examples 41 to 52, Comparative Examples 2 and 3]
An organic light-emitting device was produced in the same manner as in Example 40, except that the organic compound layer in Example 40 was appropriately changed to the compounds shown in Table 11. However, in Examples 47 to 52, the thickness of the first light emitting layer was 10 nm. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 40. Table 11 shows the measurement results.

  From Table 11, since the red chromaticity coordinates of Comparative Examples 2 and 3 are (0.63, 0.35) and (0.62, 0.35), respectively, the chromaticity coordinates of red are shallower than the red coordinates of sRGB. is there. Therefore, the color reproduction range of sRGB cannot be satisfied. This is because the maximum emission wavelength of Comparative Compound 2 is less than 590 nm, and the maximum emission wavelength of Comparative Compound 3 is 590 nm or more, but the half width is as wide as 80 nm.

  On the other hand, when the organic compound according to the present embodiment is applied to a white light emitting device, the chromaticity (0.65, .0, .5,... 33) to (0.69, 0.31), indicating that the color reproduction range in sRGB is satisfied. This is because the organic compound according to the present embodiment not only has a longer emission wavelength λmax but also has an emission waveform with a narrow half-value width.

  The organic compound according to the present invention is a compound that emits light suitable for emitting red light. Therefore, by using the organic compound according to the present invention as a constituent material of an organic light emitting device, an organic light emitting device having good light emitting characteristics and excellent durability characteristics can be obtained.

DESCRIPTION OF SYMBOLS 10 Display device 11 Substrate 12 Moisture-proof film 13 Gate electrode 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrode 18 TFT
DESCRIPTION OF SYMBOLS 19 Insulating film 20 Contact hole 21 Anode 22 Organic compound layer 23 Cathode 24 First protective layer 25 Second protective layer 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 View finder 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 First display Two display unit 1313 Housing 1314 Bending point 1500 Car 1501 Tail lamp 1502 Window 1503 Body

Claims (20)

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

In the general formula [1], R _{1 to} R ₂₂ are each independently selected from a hydrogen atom, a halogen atom and a substituent. The substituent includes a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, substituted or unsubstituted heterocyclic group. It is any of a substituted aryloxy group, silyl group and cyano group.
At least two of R _{12 to} R ₁₄ are bonded to each other to form a ring structure. Among R _{12 to} R ₁₄ , those that do not form the ring structure are selected from a hydrogen atom, a halogen atom, and the substituent. 2. The organic compound according to claim 1, wherein in the general formula [1], at least one of a set of R ₉ and R _{18 and} a set of R ₁₀ and R ₁₇ is the aryl group.   The organic compound according to claim 2, wherein the aryl group is a phenyl group, and the phenyl group has a substituent at an ortho position.   The organic compound according to claim 3, wherein the substituent is a phenyl group. Wherein to form a ring _{structure, R 12} and _{R 13, R 13} and _{R 14,} R _{12, R 13} and any one of claims 1 to 4, characterized in that either a set of _{R 14} The organic compound according to item. The organic compound according to claim 1, which is represented by the following general formula [2].

In the general formula [2], R _{1 to} R ₂₄ represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl Group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a silyl group and a cyano group. The organic compound according to claim 1, which is represented by the following general formula [3].

In the general formula [3], R _{1 to} R ₂₄ represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group Group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a silyl group and a cyano group. The organic compound according to claim 6, wherein at least one of a set of R ₉ and R ₂₀ or a set of R ₁₀ and R ₁₉ is the aryl group.   The organic compound according to claim 8, wherein the aryl group is a phenyl group, and the phenyl group has a substituent at an ortho position.   The organic compound according to claim 9, wherein the substituent is a phenyl group. An anode, a cathode, and an organic compound layer disposed between the anode and the cathode, comprising:
An organic light-emitting device, wherein the organic compound layer includes the organic compound according to claim 1.   The organic light emitting device according to claim 11, wherein the organic compound layer is a light emitting layer.   The organic light emitting device according to claim 12, wherein the light emitting layer has a host and a guest, and the guest is the organic compound layer.   The said organic compound layer has the said light emitting layer and another light emitting layer different from the said light emitting layer, The another said light emitting layer emits a different color from the said light emitting layer, The characterized by the above-mentioned. 3. The organic light emitting device according to claim 1.   The organic light emitting device according to any one of claims 11 to 14, wherein the organic light emitting device emits white light.   A display comprising a plurality of pixels, the plurality of pixels comprising: the organic light-emitting device according to any one of claims 11 to 15; and a transistor connected to the organic light-emitting device. apparatus. An optical unit having a plurality of lenses, an image sensor that receives light passing through the optical unit, and a display unit that displays an image,
An imaging device, wherein the display unit is a display unit that displays an image captured by the imaging device, and the display unit includes the organic light emitting device according to any one of claims 11 to 15. A housing, a communication unit that communicates with the outside, and a display unit,
An electronic device, wherein the display unit includes the organic light emitting device according to claim 11. A lighting device having a light source and a light diffusion unit or an optical film,
A lighting device, comprising: the organic light emitting device according to claim 11. Having a body and a lamp provided on the body,
A moving body comprising the organic light emitting device according to any one of claims 11 to 15.

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