Organic compound and organic light-emitting device

Abstract

To provide an organic compound having excellent light emission properties.SOLUTION: The present invention discloses a specific acenaphtho [1,2-b] acephenanthryleno [5,4-k] chrysene or acenaphtho [1,2-b] acephenanthryleno [4,5-k] chrysene derivative.SELECTED DRAWING: None

Description

[Technical field]

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

[0002] An organic light-emitting element (hereinafter sometimes referred to as an "organic electroluminescence element" or an "organic EL element") is an electronic element having a pair of electrodes and an organic compound layer disposed between the electrodes. By injecting electrons and holes from the pair of electrodes, excitons of a light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting element emits light. Recent progress in organic light-emitting devices has been remarkable, including low driving voltage, diverse emission wavelengths, high-speed response, and the possibility of making light-emitting devices thinner and lighter. Incidentally, light-emitting organic compounds have been actively developed up to now. This is because the creation of compounds with excellent light-emitting properties is important for providing high-performance organic light-emitting devices. As a compound that has been created so far, the following compound 1-A is described in Patent Document 1.

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

[0004] [Patent Document 1] JP 2010-143879 A Summary of the Invention [Problem to be solved by the invention]

[0005] There is room for further improvement in the luminescence properties of the compound described in Patent Document 1. By improving the luminescence properties of the compound, it is possible to provide an organic light-emitting device with even higher luminous efficiency. That is, an object of the present invention is to provide an organic compound having excellent light-emitting properties, and another object of the present invention is to provide an organic light-emitting device having excellent light-emitting properties. [Means for solving the problem]

[0006] The organic compound of the present invention is characterized by being represented by the following general formula [1] or [2].

[0007] [ka] (In formulas [1] and [2], R1 to R 22 are each a substituent selected from 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 aryloxy group, a substituted or unsubstituted silyl group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group. R5 and R6, and R7 and R8, may be bonded to each other to form a ring structure. Effect of the Invention

[0008] The organic compound according to the present invention has a high quantum yield and is suitable for organic light-emitting devices. 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 properties can be obtained. [Brief description of the drawings]

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

[0010] ≪Organic compounds≫ First, the organic compound according to the present embodiment will be described. The organic compound according to the present embodiment is represented by the following general formula [1] or [2].

[0011] [ka]

[0012] In formulas [1] and [2], R1 to R 22 each represents a substituent selected from 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 aryloxy group, a substituted or unsubstituted silyl group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

[0013] R1 to R 22 Examples of the halogen atom represented by the formula (I) include, but are not limited to, fluorine, chlorine, bromine, and iodine.

[0014] R1 to R 22Examples of the alkyl group represented by the formula (1) include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, etc. Among these, an alkyl group having 1 to 10 carbon atoms is preferred.

[0015] R1 to R 22 Examples of the alkoxy group represented by the formula (1) include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a benzyloxy group, etc. Among these, an alkoxy group having 1 to 10 carbon atoms is preferred.

[0016] R1 to R 22 Examples of the amino group represented by the formula (1) include, but are not limited to, an N-methylamino group, an N-ethylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-methyl-N-ethylamino group, an N-benzylamino group, an N-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilino group, an N,N-diphenylamino group, an N,N-dinaphthylamino group, an N,N-difluorenylamino group, an N-phenyl-N-tolylamino group, an N,N-ditolylamino group, an N-methyl-N-phenylamino group, an N,N-dianisolylamino group, an N-mesityl-N-phenylamino group, an N,N-dimesitylamino group, an N-phenyl-N-(4-tertiary butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, and an N-piperidyl group. Among these, an amino group having 1 to 6 carbon atoms is preferred.

[0017] R1 to R 22 Examples of the aryloxy group represented by the formula (I) include, but are not limited to, a phenoxy group and a thienyloxy group.

[0018] R1 to R 22Examples of the silyl group represented by the formula (I) include, but are not limited to, a trimethylsilyl group, a triphenylsilyl group, and the like.

[0019] R1 to R 22 Examples of the aromatic hydrocarbon group represented by the formula (1) include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a fluoranthenyl group, a triphenylenyl group, etc. Among these, aromatic hydrocarbon groups having 6 to 30 carbon atoms are preferred.

[0020] R1 to R 22 Examples of the heterocyclic group represented by the formula (1) 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, etc. Among these, a heterocyclic group having 3 to 27 carbon atoms is preferred.

[0021] R1 to R 22 Examples of the substituent that may be further possessed by the alkyl group, alkoxy group, amino group, aryloxy group, silyl group, aromatic hydrocarbon group, and heterocyclic group represented by the formula (I) include, but are not limited to, halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, and tertiary butyl group; alkoxy groups such as methoxy group, ethoxy group, and propoxy group; amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, and ditolylamino group; aryloxy groups such as phenoxy group; aromatic hydrocarbon groups such as phenyl group and biphenyl group; heterocyclic groups such as pyridyl group and pyrrolyl group; and cyano group.

[0022] In the organic compound according to this embodiment, R5 and R6, and R7 and R8 may be bonded to each other to form a ring structure.

[0023] In the organic compound according to the first embodiment, R5 and R6, and R7 and R8 are not bonded to each other to form a ring structure.

[0024] The organic compound according to the second embodiment is represented by the following general formulas [3] to [5].

[0025] [ka]

[0026] In formulas [3] to [5], R 23 ~R 26 each represents a substituent selected from 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 aryloxy group, a substituted or unsubstituted silyl group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

[0027] R 23 ~R 26 The halogen atom, alkyl group, alkoxy group, amino group, aryloxy group, silyl group, cyano group, trifluoromethyl group, aromatic hydrocarbon group, and heterocyclic group represented by the formula: 22 The same as those explained in . Also, R 23 ~R 26 The alkyl group, alkoxy group, amino group, aryloxy group, silyl group, aromatic hydrocarbon group, and heterocyclic group represented by the formula (I) may further have a substituent, and R1 to R2 may further have a substituent. 22 Examples of the above-mentioned methods are the same as those described above.

[0028] The organic compound according to this embodiment includes R1 to R3, R 10 ~R 13 , and R 22 At least one of R2 to R3 and R4 may be a substituent selected from a substituted or unsubstituted aromatic hydrocarbon group and a substituted or unsubstituted heterocyclic group. 10 , R 12 ~R13 , and R 22 At least one of R2 to R3 and R4 may be a substituent selected from a substituted or unsubstituted aromatic hydrocarbon group and a substituted or unsubstituted heterocyclic group. 10 , R 12 ~R 13 , and R 22 At least one of R2 to R3 and R4 may be substituted or unsubstituted benzene or substituted or unsubstituted naphthalene. 10 , R 12 ~R 13 , and R 22 At least one of them may be benzene having a cyano group or naphthalene having a cyano group.

[0029] Next, a method for synthesizing the organic compound according to the present embodiment will be described. The organic compound according to the present embodiment can be synthesized, for example, according to the reaction scheme shown below.

[0030] [ka]

[0031] [ka]

[0032] Various compounds can be obtained by appropriately changing the compounds shown in (a) to (c) and (a') to (c') above. In the above synthesis route, an isomer is generated in the second step, and the target product is obtained as a mixture with the isomer. Since there is almost no difference in the properties of the obtained isomers, the performance of the organic light-emitting device is not affected even if the mixture is used. Of course, it may be isolated by using recrystallization or column chromatography. By forming a mixture containing isomers, the solubility and sublimation of the material can be improved. In addition, when used in an organic light-emitting device, the amorphous nature of the organic thin film is increased, resulting in good film properties. The improvement in film properties can be expected to have an effect of further improving the luminous efficiency and driving durability of the organic light-emitting device. The synthesis method will be described in detail in the examples.

[0033] Next, since the organic compound according to the first embodiment has the following characteristics, it is a compound having a high quantum yield and excellent sublimability and solubility. Furthermore, by using this organic compound, it is possible to provide an organic light-emitting device having excellent luminous efficiency and element durability. (1) The oscillator strength of the basic structure itself is high (2) The basic structure itself has low symmetry The basic skeleton here refers to acenaphtho[1,2-b]acephenanthryleneno[5,4-k]chrysene or acenaphtho[1,2-b]acephenanthryleneno[4,5-k]chrysene, and the substituents refer to R1 to R2 in the general formula [1] [2]. 22 These features will be explained below.

[0034] (1) The oscillator strength of the basic structure itself is high In creating the organic compound of the first embodiment, the inventors focused on the oscillator strength of the basic skeleton itself. Specifically, they found that the oscillator strength increases when the basic skeleton is extended in the direction of the molecular long axis. Here, the oscillator strength is an index that indicates the ease with which an electronic transition occurs, and the following relationship holds between the oscillator strength f and the quantum yield Φp.

[0035]

number

[0036] Here, Table 1 shows the results of a comparison of the oscillator strength between the basic skeleton of the first embodiment and diacenaphtho[1,2-b:1′,2′-k]chrysene, which is the basic skeleton of the compound described in Patent Document 1.

[0037] [Table 1]

[0038] The oscillator strength was calculated using the following molecular orbital calculation. The molecular orbital calculation method used was density functional theory (DFT). The functional was B3LYP, and the basis set was 6-31G. *For example, the dynamic range of the graph is Gaussian09(Gaussian09,R evisionC.01,MJFrisch,GWTrucks,HBSchlegel,GEScuser ia, MARobb, JRCheeseman, G. Scalmani, V. Barone, B. Mennucci, G. Petersson, H. Nakatsuji, M. Caricato, X. Li, HPHra tchian, AFIzmaylov, J. Bloino, G. Zheng, JLSonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishi da,T.Nakajima,Y.Honda,O.Kitao,H.Nakai,T.Vreven,JAMontgomery,Jr.,JEPeralta,F.Ogliaro,M.Bearpark,JJHe yd, E. Brothers, KNKudin, VNS Taroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, JCBurant ,SSIyengar,J.Tomasi,M.Cossi,N.Rega,JMMillam,M.Klene,JEKnox,JBCross,V.Bakken,C.Adamo,J.Jaramillo,R.G omperts,REStratmann,O.Yazyev,AJAustin,R.Cammi,C.Pomelli,JWOchterski,RLMartin,K.Morokuma,VGZakrzews ki,GAVoth,P.Salvador,JJDannenberg,S.Dapprich,ADDaniels,O.Farkas,JBForesman,JVOrtiz,JCioslowski,and DJFox,Gaussian,Inc.,Wallingford CT,2010.). The snow-white snowflakes of the snowflakes are smooth.

[0039] It can be seen from Table 1 that the basic skeleton of the first embodiment has a larger oscillator strength than the basic skeleton of the prior art. This is considered to be because the direction of the transition dipole moment coincides with the direction of the molecular long axis, resulting in a higher oscillator strength.

[0040] Next, the quantum yield of the organic compound according to the first embodiment will be described while comparing and contrasting comparative compounds having a structure similar to that of the organic compound according to the first embodiment. Here, the comparative compound is comparative compound (1) shown in Table 2, and this comparative compound (1) is a compound having a basic skeleton (diacenaphtho[1,2-b:1',2'-k]chrysene skeleton) similar to that of compound 1-A described in Prior Art Document 1. One of the organic compounds according to the first embodiment is a compound shown in Exemplary Compound A17. Exemplary Compound A17 is a compound having a structure in which R2 and R 12 is a benzene ring, and R, R to R 11 , R 13 ~R 22 is a hydrogen atom.

[0041] 1 x 10 of each compound -5 The emission spectrum of the toluene solution in mol / l was measured, and the results are shown in Table 2. The measurement was performed by measuring photoluminescence at room temperature at an excitation wavelength of 350 nm using a Hitachi F-4500. The absolute quantum yield of each compound in solution at room temperature was measured using an absolute PL quantum yield measurement device (C9920-02) manufactured by Hamamatsu Photonics KK, and the results are shown in Table 2. The quantum yield values ​​are expressed as relative values, with the quantum yield of the solution of the exemplary compound A17 set to 1.00.

[0042] [Table 2]

[0043] From Table 2, the quantum yield of the comparative compound (1) is 0.95, whereas the quantum yield of the exemplary compound A1 is 1.00, which is large. This is considered to be because the compound of the first embodiment has a molecular structure longer in the molecular long axis direction and a higher oscillator strength than the comparative compound (1). In other words, it can be seen that the exemplary compound of the first embodiment is a compound with more excellent luminescence properties.

[0044] As described above, the compound of the first embodiment has a high quantum yield because the oscillator strength of the basic skeleton itself is large. Furthermore, an organic light-emitting device using this compound has high luminous efficiency and exhibits excellent luminous characteristics.

[0045] In addition, the maximum emission wavelength (λmax) was the same for example compound A17 and comparative compound (1). In general, in condensed polycyclic aromatics, when the condensation site is expanded, the emission wavelength becomes longer. Although example compound A17 has a condensed ring structure that is more expanded than comparative compound (1), the emission wavelength was about the same. This result will be described later.

[0046] (2) The basic structure itself has low symmetry Generally, polycyclic aromatic hydrocarbons have high molecular planarity, so molecular packing is strong. Molecular packing is undesirable because it increases crystallinity and leads to reduced sublimability and solubility and concentration quenching. In other words, by suppressing molecular packing, it is possible to improve sublimability and solubility and suppress concentration quenching. Improving sublimability enables the high purification of materials by sublimation purification and the preparation of organic light-emitting devices by vapor deposition. In addition, improving solubility enables the high purification of materials by recrystallization or column purification. In other words, improving sublimability and solubility can increase the purity of materials and reduce impurities contained in organic light-emitting devices. This can prevent the organic light-emitting device from suffering from a decrease in luminous efficiency and a decrease in driving durability due to impurities. In addition, suppressing concentration quenching is also preferable in terms of improving the luminous efficiency of organic light-emitting devices.

[0047] Therefore, the present inventors focused on the molecular structure of the basic skeleton. By reducing the symmetry of the basic skeleton itself, molecular packing can be suppressed.

[0048] The basic skeleton of the compound of the first embodiment is an acenaphtho[1,2-b]acephenanthryleno[5,4-k]chrysene skeleton or an acenaphtho[1,2-b]acephenanthryleno[4,5-k]chrysene skeleton. These skeletons have no rotation axis and have a symmetry plane (σ) including the molecular plane, so the point group is classified as Cs. As an example, the acenaphtho[1,2-b]acephenanthryleno[4,5-k]chrysene skeleton is shown below. On the other hand, the diacenaphtho[1,2-b:1',2'-k]chrysene skeleton described in Patent Document 1 has a two-fold rotation axis (C2) in the diagonal direction of the molecular plane and has a symmetry plane (σv) including this two-fold rotation axis, so the point group is classified as C2v.

[0049] [ka]

[0050] Therefore, the symmetry of the molecule is in the order of decreasing from the diacenaphtho[1,2-b:1',2'-k]chrysene skeleton described in Patent Document 1 to the acenaphtho[1,2-b]acephenanthrileno[4,5-k]chrysene skeleton of the first embodiment. From the above, since the basic skeleton of the first embodiment itself is a skeleton with low symmetry, it can be said that the organic compound of the first embodiment is a molecule with low symmetry.

[0051] Molecules with low symmetry are more likely to have disordered molecular arrangements in solids than molecules with high symmetry, and molecular packing, in which molecules regularly overlap, is suppressed. Compounds with suppressed molecular packing have improved sublimation and solubility. In addition, concentration quenching can be suppressed by preventing association between molecules.

[0052] Here, the effect of the asymmetry of the basic skeleton is compared between the comparative compound (2) and the exemplary compound A1. The comparative compound (2) has the same basic skeleton (diacenaphtho[1,2-b:1',2'-k]chrysene skeleton) as the compound 1-A described in the prior art document 1.

[0053] The results of comparing the temperature difference between the decomposition temperature and the sublimation temperature of each compound are shown in Table 3. The sublimation temperature is 1×10 -1 The temperature was slowly raised under a vacuum of 10 Pa while Ar was flowing, and sublimation purification was started, and the temperature was determined as the temperature at which a sufficient sublimation rate was reached. The decomposition temperature was determined as the temperature at which the weight loss reached 5% by TG / DTA measurement. Table 3 also shows the results of a toluene solubility test comparing the amount of toluene required to dissolve 100 mg of each compound. In the toluene solubility test, the mixture was refluxed under heating and stirring in a nitrogen atmosphere, and dissolution was confirmed visually, and the results were expressed as a relative value when the amount of toluene used to completely dissolve the exemplary compound A1 was set to 1.0.

[0054] [Table 3]

[0055] From Table 3, the exemplary compound A1 has a larger temperature difference between the decomposition temperature and the sublimation temperature than the comparative compound (2). The larger the temperature difference between the decomposition temperature and the sublimation temperature, the larger the temperature margin in the sublimation purification, and therefore the better the sublimation property. In addition, the exemplary compound A1 can be dissolved in a smaller amount of solvent than the comparative compound (2), and is therefore superior in solubility.

[0056] Generally, the larger the molecular weight, the lower the sublimability and the lower the solubility, but the example compound A1 has a higher molecular weight than the comparative compound (2), yet it has excellent sublimability and solubility. This is thought to be because the molecular packing is suppressed due to the low symmetry of the basic skeleton itself.

[0057] That is, the compound of the first embodiment has high sublimability and can be purified by sublimation without decomposition by suppressing molecular packing. In addition, since the compound has high solubility, it is a material that can be easily purified by using a purification method such as column purification, in which high solubility is preferable. Therefore, an organic light-emitting element using this material has excellent driving durability.

[0058] As described above, the organic compound according to the first embodiment has the characteristics of the above conditions (1) and (2), and is therefore a compound excellent in quantum yield, sublimability, and solubility.

[0059] In addition, as a structure in which one side of the benzene ring of the diacenaphtho[1,2-b:1',2'-k]chrysene skeleton described in the prior art document 1 is condensed to reduce symmetry, structural isomers other than the acenaphtho[1,2-b]acephenanthryleneno[5,4-k]chrysene skeleton, which is the basic skeleton of the first embodiment, and the acenaphtho[1,2-b]acephenanthryleneno[4,5-k]chrysene skeleton are also considered. Therefore, molecular orbital calculations were performed on the structural isomers. The results are shown in Table 4.

[0060] [Table 4]

[0061] The basic structure of the general formula [1] is a structure in which benzene rings are condensed at the 2 and 3 positions of diacenaphtho[1,2-b:1',2'-k]chrysene. In contrast, the comparative compound (3) is a structure in which benzene rings are condensed at the 1 and 2 positions of diacenaphtho[1,2-b:1',2'-k]chrysene.

[0062] As shown in Table 4, it can be seen that the S1 (singlet excited state) of the comparative compound (3) is larger than that of diacenaphtho[1,2-b:1',2'-k]chrysene. In other words, the emission wavelength becomes longer. For this reason, the comparative compound (3) does not have an emission wavelength in the blue emission region (420 nm to 480 nm), and cannot be used as a blue light-emitting material. In addition, as a blue light-emitting material, it is preferable that the chromaticity of the blue light is deeper, that is, the emission wavelength is shorter, in terms of expanding the color reproduction range.

[0063] On the other hand, the compound of the first embodiment has the same basic skeleton as diacenaphtho[1,2-b:1',2'-k]chrysene and S1, even though the condensed ring is expanded. In addition, since the basic skeleton itself has an emission wavelength in the blue emission region, it can be used as a blue light-emitting material. Of course, it can also be used as a green to red light-emitting material by providing an appropriate substituent.

[0064] Therefore, the organic compound of the first embodiment has a high quantum yield and excellent sublimation and solubility. In addition, the organic compound can be used as a light-emitting material in a wide range from blue to red. In particular, the organic compound can be used as a light-emitting material that emits light in a deep blue range.

[0065] Furthermore, it is preferable that the organic compound satisfies the following condition (3). (3) Having bulky substituents at substitution positions that increase the dihedral angle between the basic structure and the substituents This is because, when condition (3) is satisfied, the dihedral angle between the basic skeleton and the substituent becomes large, and molecular packing can be further suppressed. Furthermore, when at least one of the substituents is a group other than a hydrogen atom, preferably a bulky group, molecular packing in which the basic skeletons overlap each other is suppressed, which is preferable. Here, the dihedral angle was estimated using molecular orbital calculations, using general formula [1] as an example. The results are shown in Table 5.

[0066] [Table 5]

[0067] From Table 5, R1 to R3, R 10 ~R 15 , R 18 ~R 19 , and R 22 In the above formula, the dihedral angle is 58° or more. Since the dihedral angle is sufficiently large, the π-π interaction between the basic skeletons can be suppressed by the substituent (benzene). Therefore, it is preferable because it is a material with high solubility and sublimability. In addition, it is preferable because it can reduce concentration quenching and the shift of the emission wavelength to longer wavelengths when used as a light-emitting material for an organic light-emitting element.

[0068] More preferred substitution positions are R1 to R3, R 10 ~R 13 , and R 22 More preferably, R2 to R3, R 10 , R 12 ~R 13 , and R 22 This is because these substitution positions are the substitution positions of the chrysene moiety in the center of the basic skeleton molecule, and can more effectively suppress molecular packing.

[0069] Next, since the organic compound according to the second embodiment has the following characteristics, it has a high quantum yield, and further, by using this organic compound, it is possible to provide an organic light-emitting device having excellent luminous efficiency. (4) The oscillator strength of the basic structure itself is high The basic skeleton here means diacephenanthryleneno[5,4-b:5',4'-k]chrysene in the general formula [3], diacephenanthryleneno[4,5-b:5',4'-k]chrysene in the general formula [4], and diacephenanthryleneno[4,5-b:4',5'-k]chrysene in the general formula [5], and the substituent means R1 to R2 in the general formulas [3] to [5]. 26 This feature will be explained below.

[0070] (4) The oscillator strength of the basic structure itself is high In creating the organic compound of the second embodiment, the inventors focused on the oscillator strength of the basic skeleton itself. Specifically, they found that the oscillator strength can be increased by expanding the basic skeleton in the direction of the molecular long axis. Here, the oscillator strength is as explained in the section "(1) The oscillator strength of the basic skeleton itself is high."

[0071] Table 6 shows a comparison result of the oscillator strength between the basic skeleton of the second embodiment and diacenaphtho[1,2-b:1',2'-k]chrysene, which is the basic skeleton of the compound described in Patent Document 1. The calculation of the oscillator strength is as explained in the section "(1) The basic skeleton itself has high oscillator strength."

[0072] [Table 6]

[0073] From Table 6, it can be seen that the basic skeleton of the second embodiment has a larger oscillator strength than the basic skeleton of the prior art. This is considered to be because the direction of the transition dipole moment coincides with the direction of the molecular long axis, resulting in a higher oscillator strength.

[0074] Next, the quantum yield of the organic compound according to the second embodiment will be described while comparing and contrasting comparative compounds having a structure similar to that of the organic compound according to the second embodiment. Here, the comparative compound is comparative compound (1) shown in Table 7, which is a compound having a basic skeleton (diacenaphtho[1,2-b:1',2'-k]chrysene skeleton) similar to that of compound 1-A described in Prior Art Document 1. One of the organic compounds according to the second embodiment is a compound shown in Exemplary Compound D2. Exemplary Compound D2 is a compound having a structure in which R2 and R 12 is a benzene ring having a methyl group as a substituent, and R, R to R, R to R 11 , R 13 ~R 26 is a hydrogen atom.

[0075] 1 x 10 of each compound -5The emission spectrum of the toluene solution in mol / l at room temperature was measured by photoluminescence at an excitation wavelength of 350 nm using a Hitachi F-4500, and the results are shown in Table 7. The absolute quantum yield of each compound in solution at room temperature was measured using an absolute PL quantum yield measurement device (C9920-02) manufactured by Hamamatsu Photonics KK, and the results are shown in Table 7. The quantum yield values ​​are expressed as relative values, with the quantum yield of the solution of the example compound D2 set at 1.00.

[0076] [Table 7]

[0077] From Table 7, the quantum yield of the comparative compound (1) is 0.95, whereas the quantum yield of the exemplary compound D2 is 1.00, which is large. This is considered to be because the compound of the second embodiment has a molecular structure longer in the molecular long axis direction and a higher oscillator strength than the comparative compound (1). In other words, it can be seen that the exemplary compound of the second embodiment is a compound with superior luminescence properties.

[0078] As described above, the compound of the second embodiment has a high quantum yield because the oscillator strength of the basic skeleton itself is large. Furthermore, an organic light-emitting device using this compound has high luminous efficiency and exhibits excellent luminous characteristics.

[0079] In addition, the maximum emission wavelength (λmax) was similar for example compound D2 and comparative compound (1). In general, in condensed polycyclic aromatic compounds, as the condensation site expands, the emission wavelength becomes longer. Although example compound D2 has a condensed ring structure that is more expanded than comparative compound (1), the emission wavelength was similar. The results are described below.

[0080] As the structure in which one side of the benzene ring of the diacenaphtho[1,2-b:1',2'-k]chrysene skeleton described in the prior art document 1 is condensed, structural isomers other than the diacephenanthryleneno[5,4-b:5',4'-k]chrysene skeleton, diacephenanthryleneno[4,5-b:5',4'-k]chrysene skeleton, and diacephenanthryleneno[4,5-b:4',5'-k]chrysene, which are the basic skeletons of the second embodiment, are considered. Therefore, molecular orbital calculations were performed on the structural isomers. The results are shown in Table 8.

[0081] [Table 8]

[0082] The basic structure of the general formula [3] is a structure in which benzene rings are condensed at the 2- and 3-positions and the 12- and 13-positions of diacenaphtho[1,2-b:1',2'-k]chrysene. The basic structure of the general formula [4] is a structure in which benzene rings are condensed at the 2- and 3-positions and the 14- and 15-positions of diacenaphtho[1,2-b:1',2'-k]chrysene. The basic structure of the general formula [5] is a structure in which benzene rings are condensed at the 12- and 13-positions and the 14- and 15-positions of diacenaphtho[1,2-b:1',2'-k]chrysene. In contrast, the comparative compound (4) is a structure in which benzene rings are condensed at the 1- and 2-positions and the 11- and 12-positions of diacenaphtho[1,2-b:1',2'-k]chrysene.

[0083] As shown in Table 8, it can be seen that the S1 (singlet excited state) of the comparative compound (4) is larger than that of diacenaphtho[1,2-b:1',2'-k]chrysene. In other words, the emission wavelength becomes longer. For this reason, the comparative compound (4) does not have an emission wavelength in the blue emission region (420 nm to 480 nm), and cannot be used as a blue light-emitting material. In addition, as a blue light-emitting material, it is preferable that the chromaticity of the blue light is deeper, that is, the emission wavelength is shorter, in terms of expanding the color reproduction range.

[0084] On the other hand, the basic skeleton of the compound of the second embodiment has an S1 equal to or less than that of diacenaphtho[1,2-b:1',2'-k]chrysene, even though the condensed ring is expanded. In addition, since the basic skeleton itself has an emission wavelength in the blue emission region, it can be used as a blue light-emitting material. Of course, it can also be used as a green to red light-emitting material by providing an appropriate substituent.

[0085] Therefore, the organic compound of the second embodiment has a high quantum yield. In addition, the organic compound can be used as a light-emitting material in a wide range from blue to red. In particular, the organic compound can be used as a light-emitting material that emits light in the deep blue range.

[0086] Furthermore, it is preferable that the organic compound satisfies the following condition (5). (5) Having bulky substituents at substitution positions that increase the dihedral angle between the basic skeleton and the substituents This is because, when condition (5) is satisfied, the dihedral angle between the basic skeleton and the substituent becomes large, and molecular packing can be further suppressed. Furthermore, when at least one of the substituents is a group other than a hydrogen atom, preferably a bulky group, it is preferable because molecular packing in which the basic skeletons overlap each other is suppressed. Here, the dihedral angle was estimated using molecular orbital calculations. The calculation results for general formula [3] are shown in Table 9.

[0087] [Table 9]

[0088] From Table 9, R1 to R4, R7, and R 10 ~R 14 , R 18 ~R 19 , R 22 and R 26 In the above formula, the dihedral angle is 58° or more. Since the dihedral angle is large enough, the π-π interaction between the basic skeletons can be suppressed by the substituent (benzene). This makes the material highly soluble and sublimable, which is preferable.

[0089] More preferred substitution positions are R1 to R3, R 10 ~R 13 , and R 22 More preferably, R2 to R3, R 10 , R 12 ~R 13 , and R 22 This is because these substitution positions are the substitution positions of the chrysene moiety in the center of the basic skeleton molecule, and can more effectively suppress molecular packing.

[0090] Of course, similar results can be obtained using general formulas [4] and [5].

[0091] Specific examples of the organic compound according to the present invention are shown below, but the present invention is not limited to these.

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] Exemplary compounds belonging to group A are R1 to R 22 is a hydrogen atom, an alkyl group, or an aromatic hydrocarbon group. Therefore, the compound has excellent chemical stability. Therefore, by using these compounds, a light-emitting element having excellent durability can be provided.

[0096] Exemplary compounds belonging to group B are R1 to R 22Or a compound having a heterocyclic group or a group having a heteroatom as a substituent thereof. The HOMO level or LUMO level of the compound can be adjusted by the heterocyclic group or the group having a heteroatom, and therefore the compound can be suitably used for adjusting the carrier balance of a light-emitting element.

[0097] Exemplary compounds belonging to group C include R1 to R 22 Or a compound having an electron-deficient heterocyclic group or an electron-withdrawing group as a substituent. Therefore, the HOMO level is deep (far from the vacuum level), and the compound has excellent oxidation stability. In addition, since the LUMO level is also deep, when used as a light-emitting material for a light-emitting layer, a light-emitting device having an electron-trapping light-emitting layer can be provided. In addition, it can also be used as a material constituting an electron injection layer adjacent to a cathode electrode or an electron acceptance layer in a charge generation layer. In particular, a cyano group is particularly preferable as an electron-withdrawing substituent in order to enhance the above-mentioned effect.

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] Exemplary compounds belonging to group D include R1 to R 26 is a hydrogen atom, an alkyl group, or an aromatic hydrocarbon group. Therefore, the compound has excellent chemical stability. Therefore, by using these compounds, a light-emitting element having excellent durability can be provided.

[0102] Exemplary compounds belonging to group E include R1 to R 26Or a compound having a heterocyclic group or a group having a heteroatom as a substituent thereof. The HOMO level or LUMO level of the compound can be adjusted by the heterocyclic group or the group having a heteroatom, and therefore the compound can be suitably used for adjusting the carrier balance of a light-emitting element.

[0103] Exemplary compounds belonging to group F are R1 to R 26 Or it is a compound having an electron-deficient heterocyclic group or an electron-withdrawing group as a substituent. Therefore, it is a compound with a deep HOMO level (far from the vacuum level) and excellent oxidation stability. In addition, since it has a deep LUMO level, when it is used as a light-emitting material in a light-emitting layer, it can provide a light-emitting device having an electron-trapping light-emitting layer. It can also be used as a material constituting an electron injection layer adjacent to a cathode electrode or an electron acceptance layer in a charge generation layer.

[0104] <Organic light-emitting element> The organic light-emitting element of the present embodiment has at least a pair of electrodes, an anode and a cathode, and an organic compound layer disposed between the electrodes. In the organic light-emitting element of the present embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has a light-emitting layer.

[0105] When the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole-exciton blocking layer, an electron transport layer, an electron injection layer, etc. The light-emitting layer may be a single layer or a laminate consisting of multiple layers.

[0106] In the organic light-emitting device of the present embodiment, the organic compound according to the present embodiment is contained in at least one of the organic compound layers. Specifically, the organic compound according to the present embodiment is contained in any of the hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole / exciton blocking layer, electron transport layer, electron injection layer, etc. The organic compound according to the present embodiment is preferably contained in the light-emitting layer.

[0107] In the organic light-emitting device of this embodiment, when the organic compound according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer consisting of only the organic compound according to this embodiment, or may be a layer consisting of the organic compound according to this embodiment and other compounds. Here, when the light-emitting layer is a layer consisting of the organic compound according to this embodiment and other compounds, the organic compound according to this embodiment may be used as a host of the light-emitting layer or as a guest. It may also be used as an assist material that can be contained in the light-emitting layer. Here, the host is a compound having the largest weight ratio among the compounds constituting the light-emitting layer. Also, the guest is a compound having a smaller weight ratio than the host among the compounds constituting the light-emitting layer, and is a compound that is responsible for the main emission. Also, the assist material is a compound having a smaller weight ratio than the host among the compounds constituting the light-emitting layer, and assists the emission of the guest. The assist material is also called a second host.

[0108] When the organic compound according to this embodiment is used as a guest in the light-emitting layer, the concentration of the guest is preferably from 0.01% by mass to 20% by mass, and more preferably from 0.1% by mass to 5% by mass, based on the total mass of the light-emitting layer.

[0109] In addition, when the organic compound according to this embodiment is used as a guest in the light-emitting layer, it is preferable to use a material made of aromatic hydrocarbon as a host, because the organic compound according to this embodiment is a material whose basic skeleton is made of condensed polycyclic aromatic hydrocarbon, and by using a material made of similar aromatic hydrocarbon as a host, a light-emitting layer having excellent compatibility between the host and the guest is obtained.

[0110] The present inventors have conducted various studies and found that when the organic compound according to this embodiment is used as a host or guest of the light-emitting layer, particularly as a guest of the light-emitting layer, an element that exhibits high efficiency and high luminance light output and is extremely durable can be obtained. The light-emitting layer may be a single layer or multiple layers, and the light-emitting color of this embodiment is blue light emission, and it is also possible to mix colors by including a light-emitting material having another light-emitting color. Multiple layers means a state in which a light-emitting layer and another light-emitting layer are laminated. In this case, the light-emitting color of the organic light-emitting element is not limited to blue. More specifically, it may be white or an intermediate color. In the case of white, the other light-emitting layer emits a color other than blue, that is, green or red. In addition, the film is formed by deposition or coating film formation. Details of this will be explained in detail in the examples described below.

[0111] The organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer constituting the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not limited to blue. More specifically, it may be white or a neutral color.

[0112] In addition to the organic compound according to the present embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. may be used together as necessary. Examples of these compounds are given below.

[0113] As the hole injection transport material, a material having high hole mobility is preferable so that the injection of holes from the anode can be easily performed and the injected holes can be transported to the light emitting layer. In addition, a material having a high glass transition temperature is preferable so as to suppress deterioration of the film quality such as crystallization in the organic light emitting device. Examples of low molecular weight and high molecular weight materials having hole injection transport performance include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above hole injection transport material is also preferably used in the electron blocking layer. Specific examples of compounds used as the hole injection transport material are shown below, but of course, the present invention is not limited to these.

[0114] [ka]

[0115] Examples of light-emitting materials mainly involved in the light-emitting function include, in addition to the organic compound according to this embodiment, fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives.

[0116] The organic compound of the present embodiment is a compound having two electron-deficient five-membered rings in the basic skeleton, and therefore has a low HOMO / LUMO energy. Therefore, when forming a mixed layer with other light-emitting materials or laminating light-emitting layers, it is preferable that the other light-emitting materials also have low HOMO / LUMO energy. This is because, if the HOMO / LUMO energy is high, there is a risk of forming a quenching component or a trap level, such as forming an exciplex with the organic compound of the present embodiment.

[0117] Specific examples of compounds that can be used as the light-emitting material are shown below, but the present invention is not limited to these.

[0118] [ka]

[0119] Examples of the light-emitting layer host or light-emitting assist material contained in the light-emitting layer include aromatic hydrocarbon compounds or derivatives thereof, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, and organoberyllium complexes.

[0120] Since the organic compound of this embodiment is a compound with low HOMO / LUMO energy, it is preferable that the host material is also formed from a hydrocarbon and has low HOMO / LUMO energy, because if the host material contains a heteroatom such as a nitrogen atom, the HOMO / LUMO energy becomes high and there is a risk of forming a quenching component or a trap level, such as forming an exciplex with the organic compound of this embodiment.

[0121] It is particularly preferable that the host material has an anthracene, triphenylene, chrysene, fluoranthene, or pyrene skeleton in the molecular skeleton, because, in addition to being composed of a hydrocarbon as described above, it has S1 energy that can cause sufficient energy transfer to the organic compound of this embodiment.

[0122] Specific examples of compounds used as the light-emitting layer host or light-emitting assist material contained in the light-emitting layer are shown below, but the present invention is not limited to these.

[0123] [ka]

[0124] 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. Examples of materials having electron transporting properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organic aluminum complexes, and condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transporting materials are also preferably used in the hole blocking layer. Specific examples of compounds used as electron transporting materials are shown below, but are of course not limited to these.

[0125] [ka]

[0126] <Configuration of organic light-emitting element> 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 planarizing layer may be provided between the protective layer and the color filter. The planarizing layer may be made of acrylic resin or the like.

[0127] [substrate] Examples of the substrate include quartz, glass, silicon wafer, resin, and metal. In addition, a switching element such as a transistor and wiring may be provided on the substrate, and an insulating layer may be provided thereon. As the insulating layer, any material can be used as long as it can form a contact hole to ensure electrical continuity between the anode and the wiring and can ensure insulation from wiring that is not connected. For example, resin such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0128] [electrode] A pair of electrodes can be used. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. It can also be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0129] The material constituting the anode should have as large a work function as possible. For example, metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, etc., mixtures containing these metals, alloys combining these metals, metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0130] These electrode materials may be used alone or in combination of two or more kinds. The anode may be composed of a single layer or a plurality of layers.

[0131] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or an alloy or laminate of these can be used. When used as a transparent electrode, a transparent conductive layer of oxide such as indium tin oxide (ITO) or indium zinc oxide can be used, but is not limited to these. Photolithography technology can be used to form the electrode.

[0132] On the other hand, the material for the cathode should have a small work function. Examples of the material include alkali metals such as lithium, alkaline earth metals such as calcium, aluminum, titanium, manganese, silver, lead, chromium, and other metals or mixtures containing these metals. Alternatively, alloys combining these metals can be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver, and the like can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials may be used alone or in combination of two or more types. The cathode may have a single layer structure or a multi-layer structure. Among these, it is preferable to use silver, and it is even more preferable to use a silver alloy to reduce the aggregation of silver. As long as the aggregation of silver can be reduced, the ratio of the alloy is not important. For example, it may be 1:1.

[0133] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but it is more preferable to use a direct current or alternating current sputtering method, etc., since the film coverage is good and the resistance can be easily reduced.

[0134] [Protective layer] A protective layer may be provided on the cathode. For example, by bonding glass provided with a moisture absorbent on the cathode, it is possible to suppress the intrusion of water and the like into the organic compound layer and suppress the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to suppress the intrusion of water and the like into the organic compound layer. For example, after the cathode is formed, the device may be transported to another chamber without breaking the vacuum, and a silicon nitride film having a thickness of 2 μm may be formed by the CVD method to serve as a protective layer. A protective layer may be provided using the atomic deposition method (ALD method) after the film formation by the CVD method.

[0135] [Color Filter] A color filter may be provided on the protective layer. For example, a color filter taking into consideration the size of the organic light-emitting element may be provided on another substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using a photolithography technique. The color filter may be made of a polymer.

[0136] [Planarization layer] A planarizing layer may be provided between the color filter and the protective layer. The planarizing layer may be made of an organic compound, and may be a low molecular weight or a high molecular weight compound, but is preferably a high molecular weight compound.

[0137] The planarization layer may be provided above and below the color filter, and may be made of the same or different materials.Specific examples of the materials include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0138] [Opposite substrate] The flattening layer may have a counter substrate on it. The counter substrate is called a counter substrate because it is provided at a position corresponding to the aforementioned substrate. The material of the counter substrate may be the same as that of the aforementioned substrate.

[0139] [Organic layer] The organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light emitting device according to one embodiment of the present invention are formed by the method described below.

[0140] The organic compound layer constituting the organic light-emitting device according to one embodiment of the present invention can be formed by dry processes such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively, instead of the dry process, a wet process can be used in which a layer is formed by dissolving the compound in an appropriate solvent and applying a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

[0141] Here, when the layer is formed by a vacuum deposition method or a solution coating method, crystallization is unlikely to occur and the layer has excellent stability over time. When the layer is formed by a coating method, the layer can be formed by combining with a suitable binder resin.

[0142] Examples of the binder resin include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0143] These binder resins may be used alone as homopolymers or copolymers, or in combination of two or more kinds. If necessary, known additives such as plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.

[0144] <Applications of the organic light-emitting device according to this embodiment> The organic light-emitting device according to an embodiment of the present invention can be used as a component of a display device or a lighting device, and can also be used as an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, a light-emitting device having a white light source and a color filter, etc.

[0145] The display device may be an image information processing device having an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., an information processing unit that processes the input information, and displays the input image on a display unit. The display device may have a plurality of pixels, and at least one of the plurality of pixels may have the organic light-emitting element of this embodiment and a transistor connected to the organic light-emitting element.

[0146] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of the touch panel function may be an infrared type, a capacitance type, a resistive film type, or an electromagnetic induction type, and is not particularly limited. The display device may be used in the display unit of a multifunction printer.

[0147] 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. The TFT element is an example of an active element.

[0148] 1 includes a substrate 11 such as glass and a moisture-proof film 12 for protecting a TFT element or an organic compound layer provided thereon. Reference numeral 13 denotes a metal gate electrode. Reference numeral 14 denotes a gate insulating film, and reference numeral 15 denotes a semiconductor layer.

[0149] 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 upper part of the TFT element 18. An anode 21 constituting an organic light emitting element 26 and the source electrode 17 are connected via a contact hole 20.

[0150] The method of electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT element 18 is not limited to the embodiment shown in Fig. 1. In other words, it is sufficient that either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT element 18.

[0151] 1, the organic compound layer 22 is illustrated as a single layer, but the organic compound layer 22 may be a multi-layer structure. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26.

[0152] In the display device 10 of FIG. 1, transistors are used as switching elements, but MIM elements may be used instead as switching elements.

[0153] The transistors used in the display device 10 of Fig. 1 are not limited to transistors using single crystal silicon wafers, but may be thin film transistors having an active layer on an insulating surface of a substrate. Examples of the active layer include single crystal silicon, amorphous silicon, non-single crystal silicon such as microcrystalline silicon, and non-single crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin film transistors are also called TFT elements.

[0154] The transistors included in the display device 10 of Fig. 1 may be formed in a substrate such as a Si substrate. Here, "formed in a substrate" means that the substrate itself such as a Si substrate is processed to produce the transistors. In other words, having a transistor in a substrate can be seen as the substrate and the transistor being integrally formed.

[0155] The organic light-emitting element according to this embodiment has its emission brightness controlled by a TFT, which is an example of a switching element, and by providing the organic light-emitting element on a plurality of surfaces, an image can be displayed based on the emission brightness of each element. The switching element according to this 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 may also be within the substrate. Whether to provide a transistor within the substrate or to use a TFT is selected according to the size of the display unit. For example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0156] 2 is a schematic diagram showing an example of a display device according to the present embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. Flexible printed circuits FPC1002 and 1004 are connected to the touch panel 1003 and the display panel 1005. A transistor is printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position if the display device is a portable device.

[0157] The display device according to the present embodiment may be used as a display unit of a photoelectric conversion device such as an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0158] 3(a) is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may have a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may have a display device according to this embodiment. In this case, the display device may display not only an image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the moving speed of the subject, the possibility that the subject will be blocked by an obstruction, and the like.

[0159] Since the timing suitable for imaging is short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment. This is because the organic light-emitting element has a fast response speed. A display device using an organic light-emitting element can be used more preferably than a liquid crystal display device, which requires a high display speed.

[0160] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses, and forms an image on an imaging element housed in a housing 1104. The focal points of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically.

[0161] The display device according to this embodiment may have color filters having red, green, and blue colors, the red, green, and blue colors being arranged in a delta arrangement.

[0162] The display device according to the present embodiment may be used as a display unit of an electronic device such as a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include a mobile phone such as a smartphone, a tablet, and a head-mounted display.

[0163] 3(b) is a schematic diagram showing an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit may be a biometric recognition unit that recognizes a fingerprint to perform unlocking or the like. An electronic device having a communication unit may be called a communication device.

[0164] FIG. 4 is a schematic diagram showing an example of a display device according to the present embodiment. FIG. 4(a) shows a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The light-emitting device according to the present embodiment may be used for the display unit 1302. The display device 1300 has the frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. 4(a). The lower side of the frame 1301 may also serve as the base. The frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0165] FIG. 4(b) is a schematic diagram showing another example of the display device according to the present embodiment. The display device 1310 in FIG. 4(b) is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have the light-emitting device according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be one display unit without a joint. The first display unit 1311 and the second display unit 1312 can be separated at the bending point. The first display unit 1311 and the second display unit 1312 may display different images, or the first and second display units may display one image.

[0166] FIG. 5(a) is a schematic diagram showing an example of a lighting device according to the present embodiment. The lighting device 1400 may have a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusion unit 1405. The light source 1402 may have an organic light-emitting element according to the present embodiment. The optical filter 1404 may be a filter that improves the color rendering of the light source. The light diffusion unit 1405 can effectively diffuse the light of the light source, such as for lighting up, and deliver the light over a wide range. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the lighting. If necessary, a cover may be provided on the outermost part.

[0167] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white light, natural white light, or any other color from blue to red. It may have a dimming circuit that adjusts the light intensity. The lighting device may have the organic light-emitting element of this embodiment and a power supply circuit connected thereto. The power supply circuit is a circuit that converts AC voltage into DC voltage. Moreover, white has a color temperature of 4200K, and natural white has a color temperature of 5000K. The lighting device may have a color filter.

[0168] The lighting device according to the present embodiment may also include a heat dissipation section that dissipates heat from within the device to the outside, and examples of the heat dissipation section include metals with high specific heat, liquid silicon, and the like.

[0169] 5B is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has tail lamps, which are an example of a lamp. The automobile 1500 has tail lamps 1501, and may be configured to turn on the tail lamps when braking or the like is performed.

[0170] The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp 1501 may have a protective member for protecting the organic light-emitting element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0171] The automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display unless it is a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials of the electrodes and the like of the organic light-emitting element are made of transparent members.

[0172] The moving body according to the present embodiment may be a ship, an aircraft, a drone, or the like. The moving body may have a body and a lamp provided on the body. The lamp may emit light to indicate the position of the body. The lamp has the organic light-emitting element according to the present embodiment.

[0173] FIG. 6 is a schematic diagram showing an example of an image forming apparatus according to the present embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus, and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is emitted from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 includes an organic light-emitting element according to the present embodiment. The developing unit 31 includes a toner and the like. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0174] 7(a) and 7(b) are diagrams showing the exposure light source 28, and are schematic diagrams showing a state in which a plurality of light-emitting sections 36 are arranged on a long substrate. Arrow 37 indicates the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis about which the photoconductor 27 rotates. This direction can also be called the long axis direction of the photoconductor 27. FIG. 7(a) shows a form in which the light-emitting sections 36 are arranged along the long axis direction of the photoconductor 27. FIG. 7(b) shows a form different from FIG. 7(a), in which the light-emitting sections 36 are alternately arranged in the column direction in each of the first column and the second column. The first column and the second column are arranged at different positions in the row direction. In the first column, a plurality of light-emitting sections 36 are arranged at intervals. In the second column, the light-emitting sections 36 are located at positions corresponding to the intervals between the light-emitting sections 36 in the first column. That is, a plurality of light-emitting sections 36 are also arranged at intervals in the row direction. The arrangement in FIG. 7(b) can also be described as a grid-like arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0175] As described above, by using a device using the organic light-emitting element according to this embodiment, it is possible to achieve a display with good image quality and stability even over a long period of time. EXAMPLES

[0176] The present invention will be described below with reference to examples, but the present invention is not limited to these. Example 1 (Synthesis of Exemplary Compounds A1 and A2)

[0177] [ka]

[0178] (1) Synthesis of compound G3 The following reagents and solvents were placed in a 200 ml recovery flask. Compound G1: 2.32g (10mmol) Compound G2: 2.10g (10mmol) Ethanol: 100ml Next, the reaction solution was heated to 70°C under a nitrogen stream, and the KOH ethanol solution was added dropwise. The mixture was further stirred at this temperature (70°C) for 6 hours. After the reaction was completed, water was added and the precipitate was filtered. The filtrate was dispersed and washed with methanol to obtain 3.04 g (yield: 75%) of a gray compound G3.

[0179] (2) Synthesis of compound G5 The following reagents and solvents were placed in a 100 ml recovery flask. Compound G3: 2.84g (7mmol) Compound G4: 2.37g (9mmol) Isoamyl nitrite: 1.05g (9mmol) Toluene: 40 ml Next, the reaction solution was heated to 110°C under a nitrogen stream and stirred at this temperature (110°C) for 3 hours. After the reaction was completed, the solution was washed twice with 40 ml of water. The organic layer was washed with saturated saline and dried over magnesium sulfate, after which the solution was filtered and the filtrate was concentrated to obtain a brown liquid. This was purified by column chromatography (chloroform / heptane = 1:4) and then recrystallized from chloroform / methanol to obtain 3.45 g (yield: 85%) of compound G5 as yellow crystals.

[0180] (3) Synthesis of compound G7 The following reagents and solvents were placed in a 200 ml recovery flask. Compound G5: 1.74g (3mmol) Compound G6: 0.79g (3mmol) Pd(PPh3)4: 0.03g Toluene: 50 ml Ethanol: 20ml 2M sodium carbonate solution: 50ml Next, the reaction solution was heated to 80° C. under a nitrogen stream and stirred at this temperature (80° C.) for 6 hours. After the reaction was completed, water was added to separate the solution, and the solution was dissolved in chloroform. The solution was purified by column chromatography (chloroform) and then recrystallized from chloroform / methanol to obtain 1.51 g (yield: 75%) of compound G7 as a yellow crystal.

[0181] (4) Synthesis of compound G8 The following reagents and solvents were placed in a 100 ml recovery flask and stirred at room temperature for 30 minutes under a nitrogen stream. (Methoxymethyl)triphenylphosphonium chloride: 1.03g (3mmol) THF: 10ml Next, the following reagents were added in this order, and the mixture was stirred at room temperature for 2 hours under a nitrogen stream. 12% potassium tert-butoxide in tetrahydrofuran: 3 ml Compound G7: 1.01g (1.5mmol) After the reaction was completed, water and ethyl acetate were added to the reaction solution. Next, the organic layer was collected by solvent extraction, and then the collected organic layer was dried using sodium sulfate. Next, the solvent contained in the organic layer was distilled off under reduced pressure to obtain a residue, which was purified by silica gel column chromatography (mobile phase; toluene:heptane=1:1) to obtain 0.94 g (yield 90%) of compound G8 as a pale yellow oil.

[0182] (5) Synthesis of compound G9 The following reagents and solvents were placed in a 200 ml recovery flask and stirred at room temperature for 30 minutes under a nitrogen stream. Compound G8: 0.84g (1.20mmol) Dichloromethane: 25 ml Next, the following reagents were added, and the mixture was stirred at room temperature for 1 hour under a nitrogen stream. Methanesulfonic acid: 0.17 g (1.80 mmol) After the reaction was completed, methanol was added to the reaction solution, and the precipitate was collected. The precipitate was purified by dispersion washing (solvent: methanol) to obtain 0.40 g (yield 50%) of compound G9 as a pale yellow solid.

[0183] (6) Synthesis of compound G11 The following reagents and solvents were placed in a 200 ml eggplant flask. Compound G9: 0.30g (0.45mmol) Compound G10: 0.09g (0.54mmol) Pd(PPh3)4: 0.005g Toluene: 50 ml Ethanol: 20ml 2M sodium carbonate solution: 50ml Next, the reaction solution was heated to 80° C. under a nitrogen stream and stirred at this temperature (80° C.) for 6 hours. After the reaction was completed, water was added to separate the solution, and the solution was dissolved in chloroform. The solution was purified by column chromatography (chloroform) and then recrystallized from chloroform / methanol to obtain 0.24 g (yield: 75%) of compound G11 as a yellow crystal.

[0184] (7) Synthesis of Example Compounds A1 and A2 The following reagents and solvents were placed in a 50 ml recovery flask. Compound G11: 214mg (0.3mmol) Pd(dba)2: 51 mg P(Cy)3 (tricyclohexylphosphine): 50mg DBU (diazabicycloundecene): 114mg 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 the reaction was completed, ethanol was added to precipitate crystals, which were then filtered and dispersed and washed in water, ethanol, and heptane, respectively. Next, the obtained yellowish brown crystals were dissolved in toluene by heating, filtered while hot, and recrystallized from toluene / methanol to obtain 122 mg of a yellow solid (yield: 60%).

[0185] The obtained compound was a mixture of Exemplary Compounds A1 and A2, and the purity of the mixture was confirmed to be 99% or more by HPLC.

[0186] The obtained compounds were subjected to mass spectrometry using MALDI-TOF-MS (Autoflex LRF, manufactured by Bruker). [MALDI-TOF-MS] Measured value: m / z=678.75 Calculated value: C 54 H 30 =678.83

[0187] Example 2 (Synthesis of Exemplary Compounds A3 and A4) A mixture of exemplified compounds A3 and A4 was obtained in the same manner as in Example 1, except that compound G12 was used instead of compound G2.

[0188] [ka]

[0189] The purity of the mixture obtained was evaluated using HPLC, and was confirmed to be 98% or more. Furthermore, mass spectrometry was performed using the MALDI-TOF-MS used in Example 1. [MALDI-TOF-MS] Measured value: m / z=903.43 Calculated value: C 70 H 32 =903.27

[0190] Example 3 (Synthesis of Exemplary Compounds C16 and C17) A mixture of exemplified compounds C16 and C17 was obtained in the same manner as in Example 1, except that compound G13 was used instead of compound G2, and compound G14 was used instead of compound G10.

[0191] [ka]

[0192] The purity of the mixture obtained was evaluated using HPLC, and was confirmed to be 98% or more. Furthermore, mass spectrometry was performed using the MALDI-TOF-MS used in Example 1. [MALDI-TOF-MS] Measured value: m / z=742.42 Calculated value: C 56 H 32 F2=742.87

[0193] <Comparative Example 1 (Synthesis of Comparative Compound (2))> Comparative compound (2) was obtained in the same manner as in Example 1, except that compound G15 was used instead of compound G1.

[0194] [ka]

[0195] The purity of the compound obtained was evaluated using HPLC, and was confirmed to be 98% or more. Furthermore, mass spectrometry was performed using the MALDI-TOF-MS used in Example 1. [MALDI-TOF-MS] Measured value: m / z=628.85 Calculated value: C 50 H 28 =628.77

[0196] Example 4 (Synthesis of Exemplary Compound A19)

[0197] [ka]

[0198] (1) Synthesis of compound G18 The following reagents and solvents were placed in a 500 ml recovery flask. Compound G16: 4.54g (10mmol) Compound G17: 5.15g (22mmol) Pd(PPh3)4: 0.2g Toluene: 200 ml Ethanol: 100ml 2M sodium carbonate solution: 100ml Next, the reaction solution was heated to 80°C under a nitrogen stream and stirred at this temperature (80°C) for 6 hours. After the reaction was completed, water was added to separate the solution, and the solution was dissolved in chloroform. The solution was purified by column chromatography (chloroform) and then recrystallized from chloroform / methanol to obtain 5.26 g (yield: 78%) of compound G18 as a yellow crystal.

[0199] (2) Synthesis of compound G19 The following reagents and solvents were placed in a 500 ml recovery flask. Compound G18: 5.00g (7.4mmol) Bispinacolborane: 11.3g (44.5mmol) Pd(dba)2: 854 mg P(Cy)3 (tricyclohexylphosphine): 1247mg Toluene: 300 ml Next, the reaction solution was heated to 110°C under a nitrogen stream and stirred at this temperature (110°C) for 3 hours. After the reaction was completed, the solution was washed twice with 40 ml of water. The organic layer was washed with saturated saline and dried over magnesium sulfate, after which the solution was filtered and the filtrate was concentrated to obtain a brown liquid. This was purified by column chromatography (chloroform / heptane = 1:4) and then recrystallized from chloroform / methanol to obtain 5.41 g (yield: 85%) of compound G19 as a gray crystal.

[0200] (3) Synthesis of compound G21 The following reagents and solvents were placed in a 500 ml recovery flask. Compound G19: 5.00 g (5.8 mmol) Compound G20: 1.67g (5.8mmol) Pd(PPh3)2Cl2: 0.41g DMSO: 200ml Sodium carbonate: 1.24g Next, the reaction solution was heated to 80°C under a nitrogen stream and stirred at this temperature (80°C) for 6 hours. After the reaction was completed, water was added to separate the solution, and the solution was dissolved in chloroform. The solution was purified by column chromatography (chloroform) and then recrystallized from chloroform / methanol to obtain 3.82 g (yield: 70%) of compound G21 as a white crystal.

[0201] (4) Synthesis of compound G23 The following reagents and solvents were placed in a 500 ml recovery flask. Compound G21: 3.82 g (4 mmol) Compound G22: 1.36g (4mmol) Pd(PPh3)2Cl2: 0.3g DMSO: 150ml Sodium carbonate: 0.86g Next, the reaction solution was heated to 80°C under a nitrogen stream and stirred at this temperature (80°C) for 6 hours. After the reaction was completed, water was added to separate the solution, and the solution was dissolved in chloroform. The solution was purified by column chromatography (chloroform) and then recrystallized from chloroform / methanol to obtain 0.64 g (yield: 15%) of compound G23 as a white crystal.

[0202] (5) Synthesis of Example Compound A19 The following reagents and solvents were placed in a 20 ml recovery flask. Compound G23: 500mg (5mmol) Pd(dba)2: 81 mg P(Cy)3 (tricyclohexylphosphine): 79mg DBU (diazabicycloundecene): 180mg DMF: 20ml Next, the reaction solution was heated to 145°C under a nitrogen stream and stirred at this temperature (145°C) for 6 hours. After the reaction was completed, ethanol was added to precipitate crystals, which were then filtered and dispersed and washed in water, ethanol, and heptane in that order. Next, the obtained yellowish brown crystals were dissolved in toluene by heating, filtered while hot, and recrystallized from toluene / methanol to obtain 106 mg of yellow exemplary compound A19 (yield: 25%).

[0203] The purity of this compound was confirmed to be 99% or more by HPLC. The exemplary compound A19 was subjected to mass spectrometry by the MALDI-TOF-MS used in Example 1. [MALDI-TOF-MS] Measured value: m / z=903.55 Calculated value: C 70 H 62 =903.27

[0204] Example 5 (Synthesis of Exemplary Compound B17) Exemplary compound B17 was obtained in the same manner as in Example 4, except that compound G24 was used instead of compound G17.

[0205] [ka]

[0206] The purity of this compound was confirmed to be 99% or more by HPLC. Incidentally, Exemplary Compound B17 was subjected to mass spectrometry by the MALDI-TOF-MS used in Example 1. [MALDI-TOF-MS] Measured value: m / z=891.26 Calculated value: C 66 H 34 S2=891.12

[0207] Example 6 (Synthesis of Exemplary Compound A21) Exemplary Compound A21 was obtained in the same manner as in Example 4, except that Compound G25 shown below was used instead of Compound G16, and Compound G26 shown below was used instead of Compound G17.

[0208] [ka]

[0209] The purity of the compound obtained was evaluated using HPLC, and was confirmed to be 99% or more. Furthermore, mass spectrometry was performed using the MALDI-TOF-MS used in Example 1. [MALDI-TOF-MS] Measured value: m / z=678.14 Calculated value: C 54 H 30 =678.83

[0210] Example 7 (Synthesis of Exemplary Compound A22) Exemplary Compound A22 was obtained in the same manner as in Example 4, except that Compound G27 shown below was used instead of Compound G16, and Compound G28 shown below was used instead of Compound G17.

[0211] [ka]

[0212] The purity of the compound obtained was evaluated using HPLC, and was confirmed to be 99% or more. Furthermore, mass spectrometry was performed using the MALDI-TOF-MS used in Example 1. [MALDI-TOF-MS] Measured value: m / z=678.14 Calculated value: C 54 H 30 =678.83

[0213] <Comparative Example 2 (Synthesis of Comparative Compound (1))> Comparative compound (1) was obtained in the same manner as in Example 4, except that compound G29 was used instead of compound G17, and compound G30 was used instead of compound G22.

[0214] [ka]

[0215] The purity of the compound obtained was evaluated using HPLC, and was confirmed to be 98% or more. Furthermore, mass spectrometry was performed using the MALDI-TOF-MS used in Example 1. [MALDI-TOF-MS] Measured value: m / z=628.82 Calculated value: C 50 H 28 =628.77

[0216] <Example 8 (Synthesis of Exemplary Compounds D1 and D2)>

[0217] [ka]

[0218] (1) Synthesis of compound H3 The following reagents and solvents were placed in a 200 ml recovery flask. Compound H1: 2.32g (10mmol) Compound H2: 2.10g (10mmol) Ethanol: 100ml Next, the reaction solution was heated to 70°C under a nitrogen stream, and the KOH ethanol solution was added dropwise. The mixture was further stirred at this temperature (70°C) for 6 hours. After the reaction was completed, water was added and the precipitate was filtered. The filtrate was dispersed and washed with methanol to obtain 3.04 g (yield: 75%) of gray compound H3.

[0219] (2) Synthesis of compound H5 The following reagents and solvents were placed in a 100 ml recovery flask. Compound H3: 2.84g (7mmol) Compound H4: 2.37 g (9 mmol) Isoamyl nitrite: 1.05g (9mmol) 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 reaction was completed, the solution was washed twice with 40 ml of water. The organic layer was washed with saturated saline and dried over magnesium sulfate, after which the solution was filtered and the filtrate was concentrated to obtain a brown liquid. This was purified by column chromatography (chloroform / heptane = 1:4) and then recrystallized from chloroform / methanol to obtain 3.45 g (yield: 85%) of compound H5 as yellow crystals.

[0220] (3) Synthesis of compound H7 The following reagents and solvents were placed in a 200 ml recovery flask. Compound H5: 1.74g (3mmol) Compound H6: 0.79g (3mmol) Pd(PPh3)4: 0.03g Toluene: 50 ml Ethanol: 20ml 2M sodium carbonate solution: 50ml Next, the reaction solution was heated to 80°C under a nitrogen stream and stirred at this temperature (80°C) for 6 hours. After the reaction was completed, water was added to separate the solution, and the solution was dissolved in chloroform. The solution was purified by column chromatography (chloroform) and then recrystallized from chloroform / methanol to obtain 1.51 g (yield: 75%) of compound H7 as yellow crystals.

[0221] (4) Synthesis of compound H8 The following reagents and solvents were placed in a 100 ml recovery flask and stirred at room temperature for 30 minutes under a nitrogen stream. (Methoxymethyl)triphenylphosphonium chloride: 1.03g (3mmol) THF: 10ml Next, the following reagents were added in this order, and the mixture was stirred at room temperature for 2 hours under a nitrogen stream. 12% potassium tert-butoxide in tetrahydrofuran: 3 ml Compound H7: 1.01g (1.5mmol) After the reaction was completed, water and ethyl acetate were added to the reaction solution. Next, the organic layer was collected by a solvent extraction operation, and then the collected organic layer was dried using sodium sulfate. Next, the solvent contained in the organic layer was distilled off under reduced pressure to obtain a residue, which was purified by silica gel column chromatography (mobile phase; toluene:heptane=1:1) to obtain 0.94 g (yield 90%) of compound H8 as a pale yellow oil.

[0222] (5) Synthesis of compound H9 The following reagents and solvents were placed in a 200 ml recovery flask and stirred at room temperature for 30 minutes under a nitrogen stream. Compound H8: 0.84g (1.20mmol) Dichloromethane: 25ml, Next, the following reagents were added, and the mixture was stirred at room temperature for 1 hour under a nitrogen stream. Methanesulfonic acid: 0.17 g (1.80 mmol) After the reaction was completed, methanol was added to the reaction solution, and the precipitate was collected. The precipitate was purified by dispersion washing (solvent: methanol) to obtain 0.40 g (yield 50%) of compound H9 as a pale yellow solid.

[0223] (6) Synthesis of compound H11 The following reagents and solvents were placed in a 200 ml recovery flask. Compound H9: 0.30g (0.45mmol) Compound H10: 0.12g (0.54mmol) Pd(PPh3)4: 0.005g Toluene: 50 ml Ethanol: 20ml 2M sodium carbonate solution: 50ml Next, the reaction solution was heated to 80° C. under a nitrogen stream and stirred at this temperature (80° C.) for 6 hours. After the reaction was completed, water was added to separate the solution, which was then dissolved in chloroform. The solution was purified by column chromatography (chloroform) and recrystallized from chloroform / methanol to obtain 0.27 g (yield: 78%) of compound H11 as yellow crystals.

[0224] (7) Synthesis of Example Compounds D1 and D2 The following reagents and solvents were placed in a 50 ml recovery flask. Compound H11: 200mg (0.3mmol) Pd(dba)2: 45mg P(Cy)3 (tricyclohexylphosphine): 44mg DBU (diazabicycloundecene): 99mg DMF: 8ml Next, the reaction solution was heated to 145°C under a nitrogen stream and stirred at this temperature (145°C) for 6 hours. After the reaction was completed, ethanol was added to precipitate crystals, which were then filtered and dispersed and washed in water, ethanol, and heptane in that order. Next, the obtained yellowish brown crystals were dissolved in toluene by heating, filtered while hot, and recrystallized from toluene / methanol to obtain 95 mg of a yellow solid (yield: 50%).

[0225] The obtained compound was a mixture of exemplary compounds D1 and D2, and the purity of the mixture was confirmed to be 99% or more by HPLC.

[0226] The compound thus obtained was subjected to mass spectrometry by the MALDI-TOF-MS used in Example 1.

[0227] [MALDI-TOF-MS] Measured value: m / z=728.84 Calculated value: C 58 H 32 =728.89

[0228] Example 9 (Synthesis of Exemplary Compounds D3 and D4) A mixture of exemplified compounds D3 and D4 was obtained in the same manner as in Example 8, except that compound H12 was used instead of compound H2.

[0229] [ka]

[0230] The purity of the mixture obtained was evaluated using HPLC, and was confirmed to be 98% or more. Furthermore, mass spectrometry was performed using the MALDI-TOF-MS used in Example 1.

[0231] [MALDI-TOF-MS] Measured value: m / z=841.34 Calculated value: C 66 H 48 =841.11

[0232] Example 10 (Synthesis of Exemplary Compounds F16 and F17) A mixture of exemplified compounds F16 and F17 was obtained in the same manner as in Example 8, except that compound H13 below was used instead of compound H2, and compound H14 below was used instead of compound H10.

[0233] [ka]

[0234] The purity of the mixture obtained was evaluated using HPLC, and was confirmed to be 98% or more. Furthermore, mass spectrometry was performed using the MALDI-TOF-MS used in Example 1.

[0235] [MALDI-TOF-MS] Measured value: m / z=768.82 Calculated value: C 58 H 34 F2=768.91

[0236] <Examples 11 to 13> Except for using the compounds shown in Table 10, a mixture of exemplary compounds D5 and D6, a mixture of exemplary compounds D9 and D10, and a mixture of exemplary compounds F13 and F14 were synthesized in the same manner as in Example 8, and the compounds were identified by HPLC and MALDI-TOF-MS.

[0237] [Table 10]

[0238] Example 14 (Synthesis of Exemplary Compound D19)

[0239] [ka]

[0240] (1) Synthesis of compound H17 The following reagents and solvents were placed in a 500 ml recovery flask. Compound H15: 4.54g (10mmol) Compound H16: 5.15g (22mmol) Pd(PPh3)4: 0.2g Toluene: 200 ml Ethanol: 100ml 2M sodium carbonate solution: 100ml Next, the reaction solution was heated to 80°C under a nitrogen stream and stirred at this temperature (80°C) for 6 hours. After the reaction was completed, water was added to separate the solution, which was then dissolved in chloroform. The solution was purified by column chromatography (chloroform) and recrystallized from chloroform / methanol to obtain 5.26 g (yield: 78%) of compound H17 as yellow crystals.

[0241] (2) Synthesis of compound H18 The following reagents and solvents were placed in a 500 ml recovery flask. Compound H17: 5.00g (7.4mmol) Bispinacolborane: 11.3g (44.5mmol) Pd(dba)2: 854 mg P(Cy)3 (tricyclohexylphosphine): 1247mg Toluene: 300 ml Next, the reaction solution was heated to 110°C under a nitrogen stream and stirred at this temperature (110°C) for 3 hours. After the reaction was completed, the solution was washed twice with 40 ml of water. The organic layer was washed with saturated saline and dried over magnesium sulfate, after which the solution was filtered and the filtrate was concentrated to obtain a brown liquid. This was purified by column chromatography (chloroform / heptane = 1:4) and then recrystallized from chloroform / methanol to obtain 5.41 g (yield: 85%) of compound H18 as yellow crystals.

[0242] (3) Synthesis of compound H20 The following reagents and solvents were placed in a 500 ml recovery flask. Compound H18: 1.00g (1.2mmol) Compound H19: 0.86g (2.6mmol) Pd(PPh3)2Cl2: 0.08g DMSO: 40ml Sodium carbonate: 0.49g Next, the reaction solution was heated to 80°C under a nitrogen stream and stirred at this temperature (80°C) for 6 hours. After the reaction was completed, water was added to separate the solution, and the solution was dissolved in chloroform. The solution was purified by column chromatography (chloroform) and then recrystallized from chloroform / methanol to obtain 0.58g (yield: 45%) of compound H20 as yellow crystals.

[0243] (4) Synthesis of Example Compound D19 The following reagents and solvents were placed in a 20 ml recovery flask. Compound H20: 500mg (5mmol) Pd(dba)2: 77mg P(Cy)3 (tricyclohexylphosphine): 75mg DBU (diazabicycloundecene): 170mg DMF: 20ml Next, the reaction solution was heated to 145°C under a nitrogen stream and stirred at this temperature (145°C) for 6 hours. After the reaction was completed, ethanol was added to precipitate crystals, which were then filtered and dispersed and washed in water, ethanol, and heptane in that order. Next, the obtained yellowish brown crystals were dissolved in toluene by heating, filtered while hot, and recrystallized from toluene / methanol to obtain 171 mg of yellow exemplary compound D19 (yield: 40%).

[0244] The purity of this compound was confirmed to be 99% or more by HPLC. The exemplary compound D19 was subjected to mass spectrometry by the MALDI-TOF-MS used in Example 1.

[0245] [MALDI-TOF-MS] Measured value: m / z=953.42 Calculated value: C 74 H 64 =953.33

[0246] Example 15 (Synthesis of Exemplary Compound E17) Exemplary compound E17 was obtained in the same manner as in Example 14, except that compound H21 was used instead of compound H16.

[0247] [ka]

[0248] The purity of this compound was confirmed to be 99% or more by HPLC. Incidentally, Exemplary Compound B17 was subjected to mass spectrometry by the MALDI-TOF-MS used in Example 1.

[0249] [MALDI-TOF-MS] Measured value: m / z=941.66 Calculated value: C 70 H 36 S2=941.18

[0250] <Example 16 (Synthesis of Exemplary Compound D21)> Exemplary compound D21 was obtained in the same manner as in Example 14, except that compound H22 below was used instead of compound H15, and compound H23 below was used instead of compound H16.

[0251] [ka]

[0252] The purity of the compound obtained was evaluated using HPLC, and was confirmed to be 99% or more. Furthermore, mass spectrometry was performed using the MALDI-TOF-MS used in Example 1.

[0253] [MALDI-TOF-MS] Measured value: m / z=728.32 Calculated value: C 58 H 32 =728.89

[0254] <Example 17> In this example, an organic EL element having a bottom emission structure was fabricated in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were successively formed on a substrate.

[0255] First, an ITO film was formed on a glass substrate, and the desired patterning process was performed to form an ITO electrode (anode). At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed was used as an ITO substrate in the following process. Next, a 1.33×10 -4 The organic EL layer and the electrode layer shown in Table 11 were successively formed on the ITO substrate by vacuum deposition using resistance heating in a vacuum chamber at 1000 Pa. Note that at this time, the electrode area of ​​the opposing electrodes (metal electrode layer, cathode) was 3 mm 2 The guest of the light-emitting layer was a mixture of the exemplary compounds A1 and A2, which was deposited by vapor deposition to form the light-emitting layer.

[0256] [Table 11]

[0257] The characteristics of the obtained element were measured and evaluated. The maximum emission wavelength of the light-emitting element was 455 nm, and blue light was emitted. Specifically, the current-voltage characteristics were measured using a microammeter 4140B manufactured by Hewlett-Packard, and the luminance was measured using a BM7 manufactured by Topcon. Furthermore, the current density was 100 mA / cm 2 The time when the luminance degradation rate reached 20% (LT80) was measured, and it exceeded 100 hours. The measurement results are shown in Table 12.

[0258] <Examples 18 to 25, Comparative Example 3> An organic light-emitting device was produced in the same manner as in Example 17, except that the compounds were appropriately changed to those shown in Table 12. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 17. The measurement results are shown in Table 12.

[0259] [Table 12]

[0260] From Table 12, the organic light-emitting device using the comparative compound (1) had an EQE of 5.2%, and the time (LT80) to reach a luminance degradation rate of 20% was 95 hours. On the other hand, the device of the example showed more efficient light-emitting characteristics and durability. This is because the guest is a compound with a higher quantum yield and higher sublimability. In Example 23, the example compounds C18 and C19 were synthesized, respectively, and the mixture adjusted to a mass ratio of 1:1 was evaporated to form an emitting layer.

[0261] <Examples 26 to 34, Comparative Example 4> An organic light-emitting device was produced in the same manner as in Example 17, except that the compounds shown in Table 13 were appropriately changed. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 17. The measurement results are shown in Table 13. The maximum emission wavelength of Example 26 was 456 nm, and blue light was emitted. Furthermore, the time when the luminance degradation rate of Example 26 reached 20% (LT80) exceeded 100 hours.

[0262] [Table 13]

[0263] From Table 13, the EQE of the organic light-emitting device using the comparative compound (1) was a low result of 5.2%. This is because the guest is the comparative compound (1) with a low quantum yield. On the other hand, the device of the example showed a highly efficient light-emitting characteristic. In Example 33, the exemplary compounds F19 and F20 were synthesized, respectively, and the mixture adjusted to a mass ratio of 1:1 was evaporated to form a light-emitting layer.

[0264] <Example 35> In this example, an organic EL element having a top-emission structure was produced in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a first emitting layer, a second emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were successively formed on a substrate.

[0265] A 40 nm thick Ti film was formed on a glass substrate by sputtering, and then patterned using photolithography to form an anode. Note that the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was 3 mm2. 2 It was made so that:

[0266] Next, the substrate with the cleaned electrodes and the material were placed in a vacuum deposition device (ULVAC), and 1.33 × 10 -4 Pa(1×10 -6 After evacuating to a pressure of 1000 psi (1000 mPa), the device was cleaned with UV / ozone. After that, each layer was formed in the layer configuration shown in Table 14, and finally, the device was sealed in a nitrogen atmosphere.

[0267] [Table 14]

[0268] The characteristics of the obtained element were measured and evaluated. The obtained element exhibited good white light emission. Furthermore, the initial luminance was 2000 cd / m 2 The degradation rate of luminance after 100 hours was measured. The results are shown in Table 15.

[0269] <Examples 36 to 43 and Comparative Example 5> An organic light-emitting device was produced in the same manner as in Example 35, except that the compounds were appropriately changed to those shown in Table 15. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 35. The measurement results are shown in Table 15.

[0270] [Table 15]

[0271] From Table 15, the organic light-emitting device using the comparative compound (2) had a luminance degradation rate of 25%. On the other hand, the device of the example had improved durability. This is because the guest is a compound that is easier to purify.

[0272] <Examples 44 to 52, Comparative Example 6> An organic light-emitting device was produced in the same manner as in Example 35, except that the compounds shown in Table 16 were appropriately changed. The luminous efficiency of the obtained device was measured and evaluated. The measurement results are shown in Table 16. The device of Example 44 exhibited good white light emission.

[0273] [Table 16]

[0274] As can be seen from Table 16, the organic light-emitting device using the comparative compound (2) had a low luminous efficiency of 3 cd / A. This is because the guest was the comparative compound (2) which had a low quantum yield. [Explanation of symbols]

[0275] 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 element, 19: insulating film, 20: contact hole, 21: anode, 22: organic compound layer, 23: cathode, 24: first protective layer, 25: second protective layer, 26: organic light-emitting element

Claims

1. An organic compound represented by the following general formula [1] or [2]: 【Chemistry 1】 (In formulas [1] and [2], R 1 ~R 22 R is a substituent selected from 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 aryloxy group, a substituted or unsubstituted silyl group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group. 5 and R 6 , and R 7 and R 8 may be bonded to each other to form a ring structure.

2. R 5 and R 6 , and R 7 and R 8 2. The organic compound according to claim 1, wherein, are not bonded to each other to form a ring structure.

3. 2. The organic compound according to claim 1, characterized in that it is represented by the following general formulas [3] to [5]. 【Chemistry 2】 (In formulas [3] to [5], R 23 ~R 26 are each a substituent selected from 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 aryloxy group, a substituted or unsubstituted silyl group, a cyano group, a trifluoromethyl group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

4. The R 1 ~R 3 , R 10 ~R 13 , and R 22 4. The organic compound according to claim 1, wherein at least one of the substituents is selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group and a substituted or unsubstituted heterocyclic group.

5. The R 2 ~R 3 , R 10 , R 12 ~R 13 , and R 22 5. The organic compound according to claim 1, wherein at least one of the substituents is selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group and a substituted or unsubstituted heterocyclic group.

6. The R 2 ~R 3 , R 10 , R 12 ~R 13 , and R 22 6. The organic compound according to claim 1, wherein at least one of the above is substituted or unsubstituted benzene or substituted or unsubstituted naphthalene.

7. The R 2 ~R 3 , R 10 , R 12 ~R 13 , and R 22 7. The organic compound according to claim 1, wherein at least one of the above is benzene having a cyano group or naphthalene having a cyano group.

8. 8. A mixture of organic compounds according to claim 1 , wherein one of the organic compounds is an organic compound represented by the general formula [1], and the other of the organic compounds is an organic compound represented by the general formula [2].

9. The mixture according to claim 8, wherein R 1 to R 22 of said one organic compound and R 1 to R 22 of said other organic compound are the same.

10. An anode and a cathode, an organic compound layer disposed between the anode and the cathode, An organic light-emitting device, wherein at least one of the organic compound layers comprises the organic compound according to claim 1 .

11. The organic light-emitting element according to claim 10, wherein the layer having the organic compound is a light-emitting layer.

12. The organic light-emitting device according to claim 11, wherein the light-emitting layer comprises a host and a guest, the host being an aromatic hydrocarbon, and the guest being the organic compound.

13. 13. The organic light-emitting element according to claim 11, further comprising another light-emitting layer disposed in a stacked state with the light-emitting layer, the another light-emitting layer emitting light of a color different from the color of light emitted by the light-emitting layer.

14. The organic light-emitting device according to claim 13, which emits white light.

15. A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to claim 10 and a transistor connected to the organic light-emitting element.

16. an optical unit having a plurality of lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays an image captured by the image sensor; The photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to claim 10 .

17. 15. An electronic device comprising: a display unit having the organic light-emitting element according to claim 10; a housing in which the display unit is provided; and a communication unit provided in the housing and configured to communicate with an external device.

18. 15. An illumination device comprising: a light source having the organic light-emitting element according to claim 10; and a light diffusion section or an optical filter that transmits light emitted by the light source.

19. A moving body comprising: a lamp having the organic light-emitting element according to claim 10; and a body on which the lamp is provided.

20. An exposure light source for an electrophotographic image forming apparatus, comprising the organic light emitting device according to claim 10 .

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